How I Invest with David Weisburd

What happens when you get fired from one of the most prestigious media companies in the world at age 36? For Michael Loeb, it meant inventing a new category in subscription services, launching one of the earliest venture studios, and incubating Priceline—one of the internet’s first great successes. In this episode, I speak with Michael Loeb, founder of Loeb.nyc, about how getting fired from Time Inc. led to the $800M sale of Synapse back to Time, his early partnership with Jay Walker to incubate Priceline, and what makes a great entrepreneur. We also dive into how Loeb.nyc works, the role of trust and pivots in building companies, and why pattern-matching VCs often get it wrong. Michael doesn’t hold back. He’s honest, funny, and full of war stories from decades of building companies—and backing founders through multiple lives.

Highlights:

• How getting fired from Time Inc. pushed Michael into entrepreneurship
• Reinventing subscriptions with continuous service and beating inertia
• The origins of Priceline and early internet innovation
• Why successful entrepreneurs are often “unemployable”
• The venture studio model behind Loeb.nyc and its high hit rate
• How to know when an old idea is worth reviving
• Why safety and trust are essential for early-stage teams
• Navigating pivots and replacing founding teams
• The evolving role of small teams in the AI era

-- Guest Bio: Michael Loeb is the founder and CEO of Loeb.nyc, a venture collective that builds, funds, and operates startups. Through Loeb.nyc, he has helped launch and scale dozens of companies by combining capital, talent, and shared services in a single ecosystem designed to dramatically improve the odds of success.

Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com.

#VentureCapital #VC #Startups #OpenLP #AssetManagement

-- Stay Connected: X / Twitter: David Weisburd: @dweisburd

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Michael Loeb: https://www.linkedin.com/in/michaelloeb1/

Links: Loeb.nyc: https://www.loeb.nyc/

-- Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

(0:00) Episode preview (0:09) Michael Loeb's journey from Time Warner to entrepreneurship (2:17) The birth of subscription services and Time Warner acquisition insights (4:07) The essence of entrepreneurial disagreeableness and innovation (7:40) The story behind Priceline's creation with Jay Walker (20:06) Recognizing the right timing for business ideas (23:16) Key factors for a company's sudden growth (27:00) The importance of adaptability and pivoting in business (32:00) Leadership strategies in emerging companies (34:47) Embracing reinvention for achieving product-market fit (35:41) The role of small teams in company scaling (38:13) Debunking the starving entrepreneur myth (40:03) Understanding the entrepreneurial drive to succeed (43:22) The American entrepreneurial ecosystem (46:03) Work-life balance for entrepreneurs (48:36) The impact of success on perception (50:43) Michael Loeb's parting wisdom and call for ideas (52:16) Analyzing success rates and VC partnerships (53:53) Impact of the NYC mayoral race on the entrepreneurial scene (56:53) Lessons from founding billion-dollar companies (57:16) Closing remarks

Sasha Pieterse might be best known for her acting career — but behind the scenes, she’s been building a beverage empire. In this episode, we dive deep into how Sasha's personal health journey led her to launch Hippie Water, a hemp-derived THC beverage brand that’s now in 140+ stores across 9 states. We talk about what it takes to transition from Hollywood to the CPG world, why Gen Z is drinking less alcohol, and how Sasha is redefining what it means to be a “celebrity founder.” This conversation goes beyond cannabis — it’s about leadership, authenticity, and building brands with staying power.

Highlights:

• Why Sasha stopped drinking alcohol — and how cannabis changed her life
• The inspiration behind Hippie Water and how it fills a social gap
• How she scaled to 140 stores in under 9 months
• The science vs. stigma behind cannabis and hemp-derived THC
• Gen Z’s changing relationship with alcohol
• What it’s really like to fundraise as a first-time, celebrity CEO
• Why Sasha believes your team is your real moat
• How she balances acting, entrepreneurship, motherhood, and hosting her podcast Women in the Nude

-- Guest Bio: Sasha Pieterse is an actress, entrepreneur, and co-founder of Hippie Water, a hemp-derived THC beverage brand. She rose to fame on the hit TV show Pretty Little Liars and now splits her time between entertainment and building her consumer goods startup. She’s also the host of the Women in the Nude podcast, where she tackles taboo topics in women’s health, business, and identity. With 21 million followers across platforms, Sasha brings a unique voice to the cannabis space — combining influence with authenticity and mission-driven leadership.

Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com.

#VentureCapital #VC #Startups #OpenLP #assetmanagement

-- Stay Connected: Twitter: David Weisburd: @dweisburd

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Sasha Pieterse-Sheaffer: https://www.linkedin.com/in/sashapieterse/

Links Hippie Water: https://www.hippiewater.com/

-- Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

(0:00) Episode preview (2:31) The science, politics, and decline in alcohol consumption among younger generations (7:49) Hippie Water's journey from prelaunch to commercial success (9:54) Insights into the day-to-day life and challenges of a CEO (15:46) Understanding the target demographic and celebrity founder dynamics (21:04) Authenticity, competitive advantage, and the industry potential of Hippie Water (23:24) Navigating the regulatory landscape for hemp beverages (26:30) Key lessons and best practices for new CEOs (30:22) Merging corporate experience with cannabis entrepreneurship (35:22) The transition from acting to podcasting and entrepreneurship (39:43) Closing remarks

This episode is a masterclass on one of the most powerful — and under-the-radar — capital structures in private markets: Small Business Investment Companies (SBICs). I’m joined by Brett Palmer, President of the Small Business Investor Alliance, and David Demeter, who helps manage Davidson College’s endowment. We dive deep into the SBIC program — a unique public-private partnership that lets private equity and credit funds access 2:1 fixed-rate, non-recourse leverage from the U.S. government. The result? LPs can access equity-like returns for credit-like risk, and fund managers gain scale without sacrificing strategy. Most people haven’t heard of it. That’s exactly why we did this episode.

Highlights:

• SBIC funds outperformed benchmarks by ~4% net IRR, per UNC-Chapel Hill study
• SBICs access 10-year fixed-rate leverage at ~50–80 bps over Treasuries
• Funds can borrow up to $175M with no refinancing risk
• Net-of-fee returns can exceed gross-of-fee returns — due to leverage
• Lower middle market is still inefficient, underprofessionalized, and rich with alpha
• Davidson College uses SBICs to target 3x net MOIC — with less risk Program has grown from $2B to $50B+ in AUM since 2008
• LPs include family offices, endowments, and banks — but few large institutions

-- Guest Bio: David Demeter helps manage Davidson College’s endowment, where he leads investments across hedge funds, venture capital, and private equity. Davidson is known for its barbell strategy — combining high-performing venture and niche private strategies like SBICs.

Brett Palmer is the President of the Small Business Investor Alliance (SBIA), the leading advocacy group for SBIC fund managers and investors. He’s been at the helm since 2008, helping modernize and grow the SBIC program.

Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com.

#VentureCapital #VC #Startups #OpenLP #assetmanagement

-- Stay Connected: X / Twitter: David Weisburd: @dweisburd

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ David Demeter: https://www.linkedin.com/in/david-d-demeter-117aa913/ Brett Palmer: https://www.linkedin.com/in/brett-palmer-2160b95/

Links: Davidson College: https://www.davidson.edu/ Small Business Investor Alliance: https://sbia.org/

-- Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

(0:00) Episode preview (1:20) SBIC performance metrics and leverage explanation (4:20) Benefits and growth of SBICs (7:41) SBIC funds' role in private credit, equity, and structural alpha (11:10) Lower middle market investments and economic impact (16:04) Backing and special features of SBIC leverage (18:33) SBIC program awareness and emerging managers (23:24) Challenges and eligibility for SBIC licensing (27:28) Davidson endowment's investment strategy (29:20) Hedge fund and venture capital investments in Davidson portfolio (31:12) Quant strategies and hedge fund allocation challenges (33:18) Resources for SBA funding and parting words (34:27) Closing remarks

What if your venture partner could talk to a thousand founders a day — and actually listen? In this episode, I speak with Andrew D’Souza, the Founder/CEO (aka Creator) of Boardy and previously the founder and CEO of Clearco (formerly ClearBank). Andrew is building something entirely new: Boardy, an AI super-connector that lives across voice, chat, and email — and introduces people to each other. He describes Boardy as a principal, not an agent — a character with its own goals, who is building goodwill and helping founders, fund managers, LPs, and executives find each other in real time. And here’s the wild part: Boardy is already responsible for over ten multimillion-dollar deals, including helping HF0 select 3 of its 10 portfolio companies, and facilitating LP meetings for emerging fund managers.

Highlights:

• 3 of HF0’s 10 most recent investments came from founders surfaced by Boardy
• Boardy has facilitated over 10 multimillion-dollar deals — including founder-investor and LP-GP introductions
• VCs are using Boardy to filter inbound, diligence deals, and ideate thesis
• Boardy works like a McKinsey partner: asking questions, forming opinions, connecting people
• Designed as a “principal,” not a “tool” — Boardy has its own goals and judgment -Trained through over 50,000 conversations, Boardy’s match rate is compounding fast
• Andrew’s team uses Boardy daily — including for hiring and internal decision-making
• Boardy speaks over voice, chat, and WhatsApp — and conversations feel more like peers than prompts

-- Guest Bio: Andrew D’Souza is the founder of Borty.ai, a voice-powered AI platform that connects people based on real-time, high-fidelity conversations. Previously, he co-founded Clearco (formerly ClearBank), where he helped pioneer revenue-based financing for e-commerce startups. Andrew is also a seasoned startup investor and advisor, and began his career at McKinsey & Co.

Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com.

#VentureCapital #VC #Startups #OpenLP #AssetManagement

Stay Connected: X / Twitter: David Weisburd: @dweisburd

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Andrew D'Souza : https://www.linkedin.com/in/andrewdsouza/

Links: Boardy: https://www.boardy.ai/

-- Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

(0:00) Episode preview (1:21) Bordy's role and application in venture space and team hiring (3:45) Bordy's experience with HF Zero accelerator and deal facilitation (8:00) Confidence in Bordy's model and matchmaking judgment (15:27) Improving fund performance and early use cases (19:12) Boardy's intelligence growth and internal company use (23:26) AI's impact on business operations and data analysis (25:02) Boardy's scalability and role in asset management (28:25) Boardy's creation, use cases, and product road map (33:39) Future integration of AI and humans in society (37:33) Boardy's market focus and compounding skills (41:28) Hiring at Boardy Inc. using Bordie (44:44) Closing remarks and contact information (46:35) Closing remarks

Alex Robinson is the Co-Founder and CEO of Juniper Square, a company transforming the private markets through technology and service. In this episode, we go deep into how he and his co-founders saw the opportunity to modernize fund administration, why the private markets are decades behind the public markets, and how Juniper Square is building for the future with AI agents. We also discuss how the best GPs scale trust with LPs, why the retail channel still hasn’t arrived in full force, and the challenges of building a system of record in a fragmented industry.

Highlights:

• How a FedEx delivery inspired Juniper Square
• Why crowdfunding was a “dumb idea” and investor relations software was the wedge
• Building trust with GPs in the early days
• Why Juniper Square is both a tech and services company
• The Pareto principle in fund admin automation
• Why LP experience matters—especially for back-office users
• Lessons from institutional LP demands and side letters
• The power law of retail fundraising in private markets
• What top GPs do to reinforce trust at every touch point
• How Juniper Square is using AI agents to transform investor relations, fund admin, and portfolio decision-making

-- Guest Bio: Alex Robinson is the Co-Founder and CEO of Juniper Square, a leading provider of investment management software for the private markets. Before Juniper Square, Alex was a serial entrepreneur in the clean tech space. He holds degrees from Harvard and Stanford, and today leads Juniper Square’s vision to bring the private markets into the digital age.

Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com.

#VentureCapital #VC #Startups #OpenLP #assetmanagement

-- Stay Connected: Twitter: David Weisburd: @dweisburd

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Alex Robinson: https://www.linkedin.com/in/alexrob22/

Links Juniper Square: https://www.linkedin.com/company/juniper-square/

-- Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

(0:00) Episode preview (1:05) Genesis and expansion of Juniper Square (3:12) Growth trajectory of private markets and the impact of the Jobs Act (5:14) Juniper Square’s contrarian view on crowdfunding and strategic focus (7:27) Evolution of Juniper Square’s target customers (10:45) Building a great product and intersection of technology in fund administration (14:45) Organizational design and customer service at Juniper Square (20:56) Juniper Square’s software tools and network effects (25:23) Diverse GP reporting methodologies and back-office experience (27:47) Retail investors' impact and shift in investor data expectations (33:53) Managing side letters and Juniper Square's business model (36:22) LP preferences and fee sensitivity in venture returns (41:17) Juniper Square's customer base and AUM privacy (45:39) Marketing strategies and growth of retail investment in alternative assets (51:28) Reinforcing trust with LPs and best practices for scaling relationships (57:12) Typical growth patterns and expansion strategies of GPs (1:02:57) Juniper Square's investment in AI and upcoming features (1:07:45) Closing remarks

Alexis John d'Amecourt is the coach behind some of the most iconic CEOs in tech today—including the founders of Substack, Eigenlayer, and Booksy. In this episode of How I Invest, I sat down with Alexis to explore what really makes great CEOs tick—and what causes them to fall apart. We talked about how founders can build trust, navigate emotional turbulence, lead organizations as they scale, and get unstuck when things feel overwhelming. Alexis also opened up about his own story—from being raised by his grandmother in D.C. after a turbulent childhood to becoming a three-time founder turned executive coach. This conversation is packed with tactical frameworks, powerful analogies, and a ton of heart.

Highlights:

• Why even the best CEOs need coaching—and what coaching actually looks like
• The most common problems CEOs face at every stage of company growth
• What to do when you’re stuck, overwhelmed, or panicked as a founder
• The difference between managing and leading—and how to do both effectively
• The one skill that top 10% employees all have in common
• A powerful tactic for giving and receiving feedback that builds trust
• What ego looks like when it helps vs. when it hurts
• How childhood experiences shape founders—and how to turn that into fuel

-- Guest Bio: Alexis John d'Amecourt is the founder of Mishory Method, an executive coaching firm that works with top CEOs and venture-backed founders around the world. His clients include the CEOs of Substack, Eigenlayer, and Booksy, among many others. A three-time founder himself, Alexis brings deep empathy and real operating experience to every conversation. I’ve seen firsthand how effective he is—and I’m excited to share this episode with you.

Alexis was born into a lineage of remarkable minds and bold innovators. His great-uncle was Stanislaw Ulam, the renowned mathematician who made foundational contributions to nuclear physics—including a vital role in the development of the hydrogen bomb—and who pioneered the use of Monte Carlo methods.

On his maternal side, Alexis was the great-great-great-grandson of Gustave de Ponton d’Amécourt, the French inventor and engineer who advanced early helicopter technology and coined the very term “helicopter.” Alexis was also the son of Joanna Harcourt-Smith, who was married to Timothy Leary—a relationship captured in Errol Morris’s documentary My Psychedelic Love Story. But his mother left when he was just two years old. Alexis was raised instead in Washington, D.C., by his Austrian grandmother, a sharp and self-made entrepreneur who became his greatest influence.

Raised between two continents—with one foot in European tradition and the other in American dynamism—Alexis was shaped by the paradox of abandonment and deep mentorship. That duality has become central to his work with CEOs today, offering a perspective grounded in resilience, heritage, and the power of reinvention.

Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com.

#VentureCapital #VC #Startups #OpenLP #AssetManagement

-- Stay Connected: X / Twitter: David Weisburd: @dweisburd

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Alexis John d'Amecourt: https://www.linkedin.com/in/alexisdamecourt/

Links: Mochary Method: https://www.mocharymethod.com/

-- Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

(0:00) Episode preview (1:39) The role and need for CEO coaching (5:08) Coaching vs. therapy for CEOs (8:08) Overcoming scaling challenges (11:57) Strategies for getting CEOs unstuck (16:11) Coaching dynamics with young CEOs (19:40) CEO misconceptions and role balance (22:33) Hiring challenges and skills of founders vs. traditional CEOs (25:02) Leadership styles: carrot vs. stick and anti selling (29:04) Managing and motivating top performers (31:20) CEO's organizational influence (33:31) Common mistakes and leadership styles of experienced CEOs (37:31) Encouraging employee peak performance (39:18) Feedback dynamics in personal and professional spheres (45:02) The role of psychopathy in scaling businesses (47:02) Ego balance for effective CEO leadership (54:32) Alexis John d'Amecourt's backstory and the power of vulnerability (59:34) Childhood trauma and its influence on founders (1:02:24) Transitioning from insecurity to vision-driven leadership (1:04:22) First principles thinking and immediate CEO improvements (1:08:17) Client profiles and contacting Alexis John d'Amecourt (1:09:19) Closing remarks

Hunter Somerville helps allocate billions of dollars across venture capital at StepStone—and he’s one of the most thoughtful LPs I’ve ever met. In this episode of How I Invest, Hunter gives us a rare look into how top institutional investors evaluate funds, pick managers, and underwrite spinouts before they even happen. We go deep on what separates the best emerging managers from the rest, how LPs think about performance before DPI, and why some GPs win repeatedly while others fade. Hunter also shares his own personal playbook—from how he manages his time to the biggest lessons he’s learned over two decades in venture. If you're raising a fund, building a firm, or just curious about how top LPs think, this one is a must-listen.

Highlights:

• The biggest myths about emerging managers—and what actually gets them funded
• Why DPI and TVPI can be misleading, and how great LPs evaluate funds pre-liquidity
• What LPs really think about spinouts—and how they prepare for them in advance
• How to stand out as a fund manager (hint: it’s not just about performance)
• Hunter’s framework for attribution, sourcing, and “right to win”
• What makes an LP want to be your first check—and why StepStone often plays that role
• Behind the scenes of StepStone’s secondaries, direct investing, and micro growth strategy
• How Hunter structures his calendar for maximum leverage—and why he believes in being “obsessively systematized”

-- Guest Bio: Hunter Somerville is a Partner at StepStone Group, one of the largest institutional investors in venture and growth equity. He leads investments across hundreds of funds, directs, and secondaries, and helps back many of the best emerging and established managers in the world. Hunter is known for his deep pattern recognition, clarity of thought, and a relentless work ethic that shows in everything he does.

Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com.

#VentureCapital #VC #Startups #OpenLP #AssetManagement

-- Stay Connected: X / Twitter: David Weisburd: @dweisburd

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Hunter Somerville:https://www.linkedin.com/in/hunter-somerville-2a24117/

Links StepStone Group: https://www.linkedin.com/company/stepstone-group/

-- Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

(0:00) Episode preview (0:42) Fundraising market and LP exposure for emerging managers (2:33) Challenges and indexing venture for mid-level emerging managers (5:08) Tracking attribution, performance, and manager skill indicators (9:41) Valuation policies, game theory, and impacts on investments (12:24) Building successful investment firms and reserve strategies (18:18) Deal attribution and components of sourcing in firms (23:32) The impact of brand and right to win at various fund stages (28:42) Differentiation strategies for venture funds (32:32) Current state and evolution of StepStone's venture practice (38:11) Incorporating AI and technology in investment management (42:23) Building and evolving relationships with investment funds (44:20) Strategies for managing a busy calendar and prioritizing tasks (47:11) Mentorship, personal growth, and career reflections (51:01) Trust and reverse references in large investment transactions (54:21) Ego, selling yourself, and StepStone's ecosystem approach (55:59) Aligning incentives and culture in organizational growth (57:07) Closing remarks

Brad Conger has a rare view into the evolving dynamics of institutional portfolios—and how allocators can adapt. As Chief Investment Officer of Hirtle Callaghan, a $20B OCIO, Brad is responsible for investment decisions across public and private markets, and he's developed a highly nuanced view of what's working, what's broken, and where alpha really comes from. In this episode, we cover the structural decline of the small-cap index, how private markets have siphoned off the highest-quality growth companies, and why illiquidity can actually be a feature—not a bug. Brad also shares how he builds conviction in contrarian positions, what makes a great spinout manager, and why bigger private equity funds may still outperform. If you're building or managing portfolios across public and private markets, this episode is full of actionable insights.

Highlights:

• Why the small-cap index is now “adversely selected”
• How private equity and venture capital have changed public markets
• The alpha case for private markets (even at today’s prices)
• The emotional benefit of illiquidity for investors
• Why “alpha fetishism” leads to poor portfolio construction
• A contrarian bet on Europe—and why it paid off
• Why good process beats good predictions
• Lessons from writing puts during a market selloff
• The underrated strengths of large PE firms
• How to underwrite spinouts—and what can go wrong
• Brad’s “crazy trade” for his 90-year-old mother

-- Guest Bio: Brad Conger is the Deputy Chief Investment Officer at Hirtle Callaghan, one of the largest outsourced CIO firms in the U.S., overseeing over $20 billion in assets. He is responsible for investment strategy across asset classes and geographies, leading the firm’s efforts in portfolio construction, manager selection, and tactical asset allocation. Brad previously worked at Goldman Sachs and holds degrees from Harvard and the Wharton School at the University of Pennsylvania.

Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com.

We’d like to thank @JuniperSquare for sponsoring this episode!

#VentureCapital #VC #Startups #OpenLP #assetmanagement

-- Sponsor: Juniper Square is dedicated to transforming the private markets investing experience. The company provides a full range of modern, connected fund technologies and services for over 2,100 private markets GPs across fundraising, reporting, fund administration, treasury, compliance, and business intelligence. Today, over $1 trillion of assets and 600,000+ LP accounts are managed through Juniper Square software and fund administration services. Learn more at www.junipersquare.com/vc.

-- Stay Connected: X / Twitter: David Weisburd: @dweisburd

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Brad Conger: https://www.linkedin.com/in/brad-conger-2990884/

-- Links: Hirtle, Callaghan & Co.: https://www.hirtlecallaghan.com/who-we-are/

-- Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

(0:00) Episode preview (0:45) Changes in the small cap index and implications for private equity (3:07) Quality and balance of public small cap companies in the new economic environment (7:15) The virtue of illiquidity in investments and issues with LP consultants (9:20) Asset allocation and finding quality in the small cap space (16:32) Thesis on investing in Europe and executing contrarian bets (20:26) Building conviction and the benefits of discretionary investment management (22:54) Role of corporate governance and client-manager relationships (25:45) Leeway for general partners and the European investment landscape (28:00) Navigating tariffs, strategic communication, and risk management (34:43) Bullish perspective on big private equity funds and talent retention challenges (41:06) Effective generational planning and diversifying a private equity portfolio (44:24) Preference for spinouts, their advantages, and fund scalability (52:09) Personal vs. client investment strategies and received wisdom in asset allocation (57:26) Evolutionary psychology and herd behavior in finance (58:33) Closing remarks

Alexander Ludwig is best known for his breakout roles in The Hunger Games and Vikings, but behind the scenes, he’s a multi-hyphenate: a passionate actor, a devoted entrepreneur, and the co-founder of Their Jewelry—a sustainable, recycled gold and silver brand he runs with his wife. In this episode, Alexander opens up about the brutal realities of Hollywood, the myth of overnight success, and how ego and humility have shaped his 20-year career. We also dive deep into how he's channeling his platform and resources to build a purpose-driven business that could help tackle the e-waste crisis. This conversation covers everything from surviving the actor’s feast-or-famine cycle to the importance of storytelling, Stoic philosophy, and finding peace in a hyper-competitive world.

Highlights:

• From Child Actor to Leading Man – Alexander reflects on the slow and painful journey from early Disney movies to The Hunger Games and Vikings
• Hollywood as a Casino – Why acting success is like rolling dice and how persistence creates your own luck
• The Myth of "Making It" – Even after Hunger Games, he still had to audition for everything
• Launching Their Jewelry – The real story behind his sustainable jewelry brand with his wife Lauren
• How E-Waste Could Power the Jewelry of the Future – Their’s plan to recycle gold from old phones to create luxury pieces
• Compounding in the Arts – How Alexander thinks about long-term career building like an investor
• Lessons from Stoicism – Why Ego Is the Enemy changed his life and every actor should read it
• Child Stardom and Money – How losing money early gave him the financial discipline he relies on today
• The Power of Entertainment – Why bringing joy to millions is no small feat Risk, Peace, and Purpose – What tech billionaires, actors, and founders all share

-- Guest Bio: Alexander Ludwig is an award-winning actor and musician best known for his roles in The Hunger Games, Vikings, and The Covenant. He began acting at age nine and has worked in the industry for over two decades. In 2020, he co-founded Their Jewelry, a sustainable jewelry brand using 100% recycled gold and sterling silver, which he runs with his wife, Lauren Ludwig. He’s also an avid country music songwriter, extreme sports enthusiast, and passionate advocate for mission-driven entrepreneurship.

Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com.

We’d like to thank @JuniperSquare for sponsoring this episode!

#VentureCapital #VC #Startups #OpenLP #assetmanagement

-- Sponsor: Juniper Square is dedicated to transforming the private markets investing experience. The company provides a full range of modern, connected fund technologies and services for over 2,100 private markets GPs across fundraising, reporting, fund administration, treasury, compliance, and business intelligence. Today, over $1 trillion of assets and 600,000+ LP accounts are managed through Juniper Square software and fund administration services. Learn more at www.junipersquare.com/vc.

-- Stay Connected: Twitter: David Weisburd: @dweisburd Alexander Ludwig: @alexanderludwig

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Alexander Ludwig: https://www.linkedin.com/in/alexander-ludwig1/

-- Links Their Jewelry: https://theirisours.com/pages/about

-- Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

(0:00) Episode preview (1:28) The role of luck and timing in an acting career (3:02) Keys to success and misconceptions in Hollywood (5:20) Ludwig's journey and persistence to his first big break (9:30) Career trajectories and the intrinsic love for acting (12:20) The impact of entertainment and audience connection (15:04) Maintaining humility and gratitude in the industry (18:50) Staying in the game through longevity, passion, and dealing with ego (22:04) The interplay of hard work, smart work, luck, and humility in success (24:46) Financial prudence, living within means, and the reality of success (31:00) Long feedback loops, compounding, and contrarian bets in careers (33:16) Passion as a driver for long-term success and career focus (39:36) Achieving success through focus vs. diversification (42:01) Synergies between podcasting and fund management (43:22) Staying within your circle of competence and balancing interests (45:38) Evaluating new opportunities and Alexander Ludwig's startup, There (48:23) Differentiating in a saturated market and sustainability initiatives (54:29) Billionaires' motivations and the drive for innovation (1:01:56) Lessons from starting as a child actor and the importance of passion (1:03:29) Balancing vision with focus and Kobe Bryant's philosophy (1:05:13) Closing remarks

Howard Lerman has founded six companies and taken one public—he's a relentless builder with an obsession for speed, innovation, and execution. Currently the Founder and CEO of Roam, Howard is reimagining what the modern workplace looks like by building the “Office of the Future,” where AI agents work alongside humans to accelerate output. In this episode, Howard joined me in How I Invest Podcast to share the frameworks and mental models behind how he leads teams, scales product-market fit, recruits S-tier engineers, and instills an almost maniacal level of urgency and creativity across the organization. We talk about what it means to enter "founder mode," why professional managers may soon be obsolete, and how cultural memes shape everything from product design to company mission. If you’re building, investing in, or simply curious about the future of work and AI-native companies—this episode is a must-listen.

Highlights:

• Why being a "cockroach" founder is a superpower in company survival
• How Roam is using AI agents to automate workflows and enable 24/7 productivity
• The "Office of the Future" and why presence matters—even virtually
• How to spot S-tier talent (and why they might be a pain to manage)
• Why product-market fit should be the last thing a founder gives up
• Howard’s nightly “founder mode” ritual and obsession with speed
• The evolution of memes and how they shape product adoption
• The dirty secret about obsession: it’s more about the people than the mission

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Guest Bio: Howard Lerman is a serial entrepreneur and currently the Founder and CEO of Roam, a startup building the "Office of the Future" by integrating AI deeply into the work experience. Previously, he was the Founder and CEO of Yext (NYSE: YEXT), which he led from startup to IPO. He is known for his strong views on founder-led companies, speed as strategy, and hiring only the best—what he calls "S-tier" talent. Howard is also an early adopter and evangelist of AI agents in the workplace.

Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com.

We’d like to thank @JuniperSquare for sponsoring this episode!

#VentureCapital #VC #Startups #OpenLP #assetmanagement

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Sponsor: Juniper Square is dedicated to transforming the private markets investing experience. The company provides a full range of modern, connected fund technologies and services for over 2,100 private markets GPs across fundraising, reporting, fund administration, treasury, compliance, and business intelligence. Today, over $1 trillion of assets and 600,000+ LP accounts are managed through Juniper Square software and fund administration services. Learn more at www.junipersquare.com/vc.

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Stay Connected: X / Twitter: David Weisburd: @dweisburd Howard Lerman: @howard

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Howard Lermar: https://www.linkedin.com/in/howardlerman/

Links: Roam: https://www.linkedin.com/company/roam-hq-inc/

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Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

(0:00) Episode preview (1:55) Applying cockroach principles and pivoting at Yext (3:38) Company structures, founder authority, and employee empowerment (6:16) Instilling speed and operating at warp speed in a company (10:01) Delegating and recruiting top talent (17:10) Building urgency and an obsession for success in teams (21:11) Howard Lerman's formative experiences and co-founder relationships (24:12) The role of memetics and memes in business (28:31) Closing remarks

Zaid Rahman is the founder and CEO of Flex, a breakout fintech startup that’s reinventing credit and payments for the middle market. Backed by the Thiel Fellowship and known for his “Delta 4” product philosophy, Zaid is building a multi-product platform that’s helping profitable, owner-operated businesses unlock capital and scale faster. In this conversation, Zaid breaks down how Flex is using AI to radically reduce underwriting time, why he’s obsessed with hiring 10x talent, and how “taste” and first principles thinking guide everything from product design to risk management. If you’re building in fintech, hiring in tech, or just obsessed with the craft of company-building, this episode is full of tactical insight.

Highlights:

• The Delta 4 framework: how to build products people rave about
• Flex’s competitive edge vs. Brex, Ramp, and legacy banks
• How Flex slashed credit underwriting time from 25 days to 48 hours using LLMs
• Why Zaid believes fintech is “still day one” in 2025
• How to spot first-principles thinkers in interviews (and why “best practices” is a red flag)
• Why Flex targets the “jumbo shrimp” of the middle market
• How Zaid built a 250+ member Thiel Fellow community from scratch
• The real cause of burnout—and how to build a sustainable high-performance culture

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Guest Bio: Zaid Rahman is the founder and CEO of Flex, a fintech platform serving mid-market businesses with credit, payments, and financial tools. A recipient of the prestigious Thiel Fellowship, Zaid previously founded multiple startups and is known for his rigorous hiring philosophy, taste-driven leadership, and commitment to building “Delta 4” experiences.

Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com.

We’d like to thank @JuniperSquare for sponsoring this episode!

#VentureCapital #VC #Startups #OpenLP #assetmanagement

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Sponsor: Juniper Square is dedicated to transforming the private markets investing experience. The company provides a full range of modern, connected fund technologies and services for over 2,100 private markets GPs across fundraising, reporting, fund administration, treasury, compliance, and business intelligence. Today, over $1 trillion of assets and 600,000+ LP accounts are managed through Juniper Square software and fund administration services. Learn more at www.junipersquare.com/vc.

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Stay Connected: X / Twitter: David Weisburd: @dweisburd Zaid Rahman: @zaidrmn

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Zaid Rahman: ​​ https://www.linkedin.com/in/zaidrahman/

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Links: Flex: https://www.linkedin.com/company/flex-super-app/

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Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

(0:00) Episode preview (2:14) David Weisburd: Benefits of the Teal fellowship and creating a WhatsApp group for fellows (4:44) David Weisburd: Using AI for credit underwriting at Flex (8:14) David Weisburd: AI's impact on efficiency and differentiating Flex from competitors (11:36) David Weisburd: Recruitment strategy and identifying team members with good taste (20:59) David Weisburd: Evaluating candidate contributions and defining unique positions (24:44) Understanding customer priorities and the importance of first principles thinking (27:09) Learning through interviews and the challenge of finding the right hire (31:06) Balancing expertise and culture fit in hiring and the role of non-10x employees (38:23) Addressing burnout in a high-intensity work environment (40:54) The future of FinTech and Flex's vision (46:27) Closing remarks

Cliff Asness is one of the most influential minds in quantitative investing and the Founder, Managing Principal and Chief Investment Officer at AQR Capital Management, which oversees over $100 billion in assets. In this wide-ranging conversation, we go deep into what makes a successful long-term strategy, how Cliff thinks about building portfolios, and why most investors misjudge both volatility and leverage. He also shares what it was like launching AQR after his early work on momentum strategies at Goldman Sachs, and what he’s learned about investor behavior across cycles. This is one of the most insightful and entertaining conversations we’ve had on the podcast—and Cliff brings both humor and hard-earned wisdom to the table.

Highlights:

• Why most investors are under-levered—and how Cliff thinks about smart leverage
• The origins of AQR’s first strategies and his early momentum research
• The problem with how investors benchmark hedge funds
• Why high volatility strategies can actually reduce risk
• The truth about hedge fund alpha—and why most funds are just “half-hedged”
• The “pull the goalie” metaphor and taking rational risks under pressure
• What AQR does (and doesn’t) believe in when it comes to machine learning
• Cliff’s view on how to build portfolios that survive 3-year drawdowns Why he thinks the best portfolios often don’t look great in the short run

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Guest Bio: Cliff Asness is the founder, Managing Principal, and Chief Investment Officer at AQR Capital Management. He holds a PhD from the University of Chicago, where he studied under Eugene Fama and Kenneth French. Cliff is widely recognized for his groundbreaking work on momentum investing and factor-based strategies, and he’s one of the most cited voices in modern quantitative finance. He has published extensively in academic journals and is known for his bold, sometimes contrarian takes on investing and market behavior.

Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com.

We’d like to thank @JuniperSquare for sponsoring this episode!

#VentureCapital #VC #Startups #OpenLP #AssetManagement

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Sponsor: Juniper Square is dedicated to transforming the private markets investing experience. The company provides a full range of modern, connected fund technologies and services for over 2,100 private markets GPs across fundraising, reporting, fund administration, treasury, compliance, and business intelligence. Today, over $1 trillion of assets and 600,000+ LP accounts are managed through Juniper Square software and fund administration services. Learn more at www.junipersquare.com/vc.

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Stay Connected: Twitter: David Weisburd: @dweisburd

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Cliff Asness: https://www.linkedin.com/in/cliff-asness/

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Links AQR: https://www.aqr.com/About-Us/OurFirm#firmfacts

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Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

(0:00) Episode preview (0:49) Managing institutional portfolios and the "pulling the goalie" metaphor (3:02) Challenges and psychology in maintaining investment strategies (8:25) Portfolio strategy combination and client preeducation (11:36) Continuous strategy improvement and balancing conviction (18:20) Handling drawdowns and hypothesis testing (21:05) Stress management and communication in fund management (29:09) Hedge fund transparency and strategy development (31:01) Hedge fund performance analysis and misconceptions (39:43) Applying valuation and momentum across markets (43:21) Risks and evolution of arbitrage and quant strategies (47:27) Machine learning and NLP in investment strategies (50:19) Data mining, alternative data, and future-oriented strategies (56:13) Integrating different investment strategies into products (1:03:11) Leverage importance and risks in investing (1:10:30) Managing high volatility strategies in portfolios (1:17:17) Complexity as a virtue and market efficiency catalysts (1:24:42) Long-term strategy mindset and AQR's future (1:28:01) AQR's competitive advantage and recruitment (1:30:03) Closing remarks

John Bowman, CEO of the CAIA Association, joins How I Invest to discuss the most important shift in institutional investing: the move from the traditional bucketed approach to the Total Portfolio Approach (TPA). In this episode, we go deep on how allocators are modernizing portfolio construction, why liquidity might be a hidden danger, and what the future of alternatives will look like as trillions of dollars flow from public to private markets.

Highlights:

• TPA vs. SAA: Why institutions are moving beyond traditional asset allocation.
• Liquidity Trap: How too much flexibility can hurt returns.
• Diversification Myth: Buckets don’t work in a world of blurred asset classes.
• Family Office Pitfalls: Why starting with direct deals is a mistake.
• Private Markets Boom: Alternatives now make up over 20% of institutional AUM.
• Access for Individuals: Platforms like iCapital and Alto are changing the game.
• Education Gap: Why advisors need to catch up as products evolve.
• The Future: Alternatives won’t be “alternative” for much longer.

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Guest Bio: John Bowman is the CEO of the CAIA Association, a global organization focused on education and professionalism in the alternatives industry. With over 14,000 charterholders worldwide, CAIA is the standard for private equity, hedge funds, private credit, and real assets. John previously held senior leadership roles at the CFA Institute and has spent decades helping institutions, advisors, and allocators navigate the evolution of the investment landscape.

Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com.

We’d like to thank @JuniperSquare for sponsoring this episode!

#VentureCapital #VC #Startups #OpenLP #assetmanagement

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Sponsor: Juniper Square is dedicated to transforming the private markets investing experience. The company provides a full range of modern, connected fund technologies and services for over 2,100 private markets GPs across fundraising, reporting, fund administration, treasury, compliance, and business intelligence. Today, over $1 trillion of assets and 600,000+ LP accounts are managed through Juniper Square software and fund administration services. Learn more at www.junipersquare.com/vc.

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Stay Connected: Twitter: David Weisburd: @dweisburd

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ John Bowman: https://www.linkedin.com/in/johnlbowmancfa/

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Links CAIA Association: https://caia.org/

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Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

(0:00) Episode preview (1:45) Evolution and comparison of investment approaches (6:03) Equity risk premia and behavioral studies on portfolio management (9:55) Sponsor: Juniper Square (10:21) The changing landscape of the sixty-forty portfolio (13:55) Institutionalization and investment strategies of family offices (22:22) Behavioral psychology's role in investment and managing ignorance debt (28:15) The impact of modern education on institutional investing (31:17) Trends in allocator portfolios and the democratization of alternatives (39:29) Regulatory impacts on private capital and liquidity constraints (46:15) Predictions for the future of the alternatives industry (49:31) The critical role of diversification and understanding asset classes (53:33) The evolving skillset for investment professionals and industry competition (55:45) Dynamics of mergers and acquisitions in the investment sector (56:41) Closing remarks

Jamie Gull is the GP/Founder of Wave Function Ventures, a deep tech seed fund, and an engineer turned investor who previously worked at SpaceX during its early, intense years of scaling. In this episode, Jamie and I discuss the high-responsibility culture at SpaceX, how it shaped Jamie’s approach to company building and investing, and what makes a deep tech founder stand out. We also explore why fast iteration matters more than perfect planning, how techno-economics drive investment decisions, and why deep tech’s reputation for being overly capital-intensive is becoming outdated. Jamie shares firsthand stories from his time working under Elon Musk, his angel investments in companies like Boom Supersonic and K2 Space, and the founding principles behind Wave Function Ventures. If you're interested in the future of deep tech investing, how to identify category-defining founders, or how hardware startups can scale efficiently, this is a must-listen.

Highlights:

• Jamie’s experience at SpaceX and the "responsible engineer" framework
• How Elon Musk's real superpower is organizational design and culture
• Why fast iteration beats careful waterfall planning in deep tech
• Jamie's investment thesis at Wave Function Ventures
• Why MBAs leading hard tech startups are often a red flag
• Understanding techno-economics and how technical feasibility isn't enough
• Lessons from investing early in Boom Supersonic and K2 Space
• Why the myth of deep tech needing excessive capital is breaking
• The role of escalation and decision-making speed at SpaceX
• How to distinguish scientific risk from engineering execution risk

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Guest Bio: Jamie Gull is the GP/Founder of Wave Function Ventures, a $10 million seed fund focused on investing in deep tech startups tackling hard hardware problems. Before becoming a full-time investor, Jamie spent over five years as an engineer at SpaceX, working on the Falcon 9 rocket, and later founded two venture-backed deep tech companies: a space deployables startup and an electric vertical takeoff and landing (eVTOL) aircraft company. His second company received eight government contracts and was acquired in 2023. Jamie combines deep engineering expertise with founder experience to help startups scale in hard tech sectors.

Over the last several cycles, prevailing wisdom in the industry has been that hard tech companies couldn’t achieve extraordinary returns. More recently, this has been busted with the dawn of companies like SpaceX, Anduril, Saronic, etc. These companies are solving large, important societal problems, capitalizing on a perfect storm of events, from geopolitical considerations, to capital, to a massive talent influx from SpaceX and the like to government support. This theme, you can call it American Dynamism, Deep Tech, or Reindustrialization, is fueling top talent to launch and build the largest techno-industrials we have seen.

However, investing in these areas requires specialized expertise. Enter Wave Function Ventures. WFV is a new deep-tech focused fund launched by industry veteran and investor Jamie Gull. Jamie possesses the depth and breadth of experience to position WFV to see and win the best deals in this space. He is a former SpaceX engineer who played a key role on Falcon 9 reentry, started and sold his own deep tech company, Talyn Air, that went through Y combinator, has VC experience as a Venture Partner at Pioneer Fund and Next Gen Venture Partners, and has been angel investing in deep tech companies for a decade in companies like Boom Supersonic, Varda, and K2 Space, among others.

Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com.

#VentureCapital #VC #Startups #OpenLP #assetmanagement

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Stay Connected: X / Twitter: David Weisburd: @dweisburd Jamie Gull: @jamiegull

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Jamie Gull: https://www.linkedin.com/in/jamie-gull/

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Links: Wave Function Ventures: https://www.wavefunction.vc/ Email: info@wavefunction.vc

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Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

(0:00) Episode preview (2:16) Role and downsides of the responsible engineer framework (5:52) SpaceX culture and personal growth (8:43) Jamie's meetings with Elon Musk (10:38) Introduction to Wave Function Ventures (12:08) Technoeconomics and founder assessment in deep tech (19:41) Comparing power law outcomes in deep tech vs. software (21:36) Analyzing technical vs. market risk in deep tech (24:39) Second-order effects and Boom Supersonic's origin (27:16) Asking the right questions in recruitment and investment (29:28) Rapid iteration's importance in deep tech startups (32:49) Traits of successful portfolio companies (36:18) Elon Musk’s approach to organizational design (39:13) Decision-making and investing strategies at SpaceX and Wave Function Ventures (41:14) Closing remarks

Paige Finn Doherty, Founding Partner of Behind Genius Ventures, joins the How I Invest podcast to share how she built one of the most distinctive brands in early-stage venture capital — all before turning 25. Paige talks about the power of content and community, how her engineering background shaped her investing style, and why being deliberate about media strategy can transform access to top founders and LPs. She also breaks down her investment thesis around AI in overlooked industries, the importance of institutional-grade operations from day one, and what it really takes to build a lasting venture firm.

Highlights:

• How Paige landed Sandana Capital as a cornerstone LP at just 24 years old
• The "substance and vibes" approach to getting LPs to say yes
• How media scaled her reach with both founders and investors
• Behind Genius Ventures’ investment theses: "technical storytellers" and "clipboard companies"
• What founders of billion-dollar companies have in common
• Building a resilient brand through storytelling, community, and consistency
• Why Behind Genius invests in embodied AI and AI agents
• How Paige thinks about sourcing deals from TikTok to co-investor networks
• Best practices for building a strong brand as an emerging manager on Twitter (now X)
• Why investing in institutional-grade back office systems from day one matters
• The vision for Behind Genius' next phase: high-production visual storytelling

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Guest Bio: Paige Finn Doherty is the Founding Partner of Behind Genius Ventures, a venture firm she launched at 22 years old to back early-stage technical storytellers building in overlooked industries. She’s the author of Seed to Harvest, a children's book about venture capital, and the host of the Seed to Harvest podcast. Paige is known for her deep conviction in building brands, fostering community, and bringing an engineering mindset to portfolio construction. Through her thought leadership, content, and investing, she’s shaping the next generation of venture capital.

Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com

We’d like to thank @Republic for sponsoring this episode!

#VentureCapital #VC #Startups #OpenLP #AssetManagement

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Sponsor: Republic is the leading global investment platform making premier private market opportunities accessible to all investors. With over $3 billion deployed across its network of investment platforms, funds, and affiliated firms, Republic opens the door to new asset classes typically reserved for institutional investors such as—private equity, venture capital, and even sports teams and your favorite film producers.

All securities, including the Hamilton Lane’s Private Infrastructure Fund, are offered through affiliate Republic Broker-Dealer, OpenDeal Broker LLC Member FINRA & SiPC. All securities come with specific risks not limited to a total loss of your investment. Past performance is not indicative of future results. Please review the risks specific to this investment on the HLPIF deal page hosted on http://republic.com/hlpif.

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Stay Connected: X / Twitter: David Weisburd: @dweisburd Twitter: https://x.com/paigefinnn

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Paige Doherty: https://www.linkedin.com/in/paigedoherty/

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Links: Seed to Harvest the Book: https://www.amazon.com/Seed-Harvest-Explanation-Venture-Capital/dp/0578906457/ Behind Genius Ventures: https://www.behindgeniusventures.com/ Behind Genius Podcast / Youtube: https://www.youtube.com/channel/UCOsbv-4bWVXIqPQAp2BCf8Q The Technical Storyteller: https://www.behindgeniusventures.com/post/technical-storyteller What it Takes (Billion Dollar Exit): https://www.behindgeniusventures.com/post/what-it-takes-1 Clipboard companies: https://www.behindgeniusventures.com/post/clipboard Cold Outreach: https://paigefinndoherty.com/2020/03/25/a-cold-outreach-workshop/ Fortune Fund II Launch: https://fortune.com/2024/04/23/behind-genius-ventures-raises-second-fund-8-million/ Term Sheets Viral Thread: https://x.com/paigefinnn/status/1255208492312358912

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Questions or topics you want us to discuss on How I Invest? Email us at david@wesiburdcapital.com.

(0:00) Introduction and guest overview (0:55) Paige's passion for venture capital and Behind Genius Ventures' differentiators (4:08) Securing top LPs and media strategy for branding and deal flow (10:39) Sponsor: Republic partnership with Hamilton Lane (11:05) Taking a stand in venture capital and advice for diverse figures (15:54) Solo GP vs. joining a top fund and value add to portfolio companies (20:12) Thesis on AI in antiquated industries and sourcing strategy evolution (26:17) Building a brand on Twitter: Strategies for VCs (30:13) Institutional service providers, LP relations, and future storytelling plans (35:03) Closing remarks and gratitude

Meghan Reynolds, Partner and Head of Capital Formation & Talent at Altimeter, has spent over 20 years at the intersection of GPs and LPs, helping some of the largest firms in the world raise capital, navigate investor relationships, and scale their strategies. In this episode, she breaks down what it takes to be a best-in-class capital raiser—how to expand into new strategies, find the right investors (not just any capital), and build enduring partnerships in a hypercompetitive environment. We also talk about what’s changed in the last 20 years, how the best GPs handle crisis communication, and why building a brand as an investor matters more than ever.

Highlights:

• The difference between capital formation and investor relations—and why many GPs get it wrong
• How fund strategy changes impact the investor base
• Why the most strategic capital isn’t always the largest check
• Lessons from educating LPs about private equity in the early 2000s and private credit in the 2010s
• The real reasons LPs don’t re-up: performance vs. transparency
• Why geography, regulation, and timing matter in capital campaigns
• How investor communication has evolved with tools like WhatsApp and Zoom
• The enduring value of warm introductions in LP fundraising
• Why small LPs might one day become your biggest supporters

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Guest Bio: Meghan Reynolds is a Partner and Head of Capital Formation & Talent at Altimeter, a technology-focused investment firm. She leads the firm’s capital formation efforts and has previously held senior roles at TPG and Goldman Sachs. Over her two-decade career, Meghan has built deep relationships across the LP landscape, spanning sovereign wealth funds, pensions, endowments, and family offices. She is known for her insights into how firms scale, evolve their strategies, and communicate effectively with investors.

Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com.

We’d like to thank @Carta and @Republic for sponsoring this episode!

#VentureCapital #VC #Startups #OpenLP #AssetManagement

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Sponsor: At Carta, we’re on a mission to connect the participants in private capital — from investors and LPs to their portfolio companies — through a suite of financial intelligence and reporting software that’s purpose-built for venture capital and private equity. Since 2018, we’ve been empowering GPs, CFOs, and CEOs to escape obsolete systems of disconnected FP&A tools — all in favor of a single, unified software suite that helps them make impactful strategic decisions and deliver outstanding results for their investors. Learn more at: www.carta.com/fundtax

Sponsor: Republic is the leading global investment platform making premier private market opportunities accessible to all investors. With over $3 billion deployed across its network of investment platforms, funds, and affiliated firms, Republic opens the door to new asset classes typically reserved for institutional investors such as—private equity, venture capital, and even sports teams and your favorite film producers.

All securities, including the Hamilton Lane’s Private Infrastructure Fund, are offered through affiliate Republic Broker-Dealer, OpenDeal Broker LLC Member FINRA & SiPC. All securities come with specific risks not limited to a total loss of your investment. Past performance is not indicative of future results. Please review the risks specific to this investment on the HLPIF deal page hosted on http://republic.com/hlpif.

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Stay Connected: X / Twitter: David Weisburd: @dweisburd

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Meghan Reynolds: https://www.linkedin.com/in/meghankreynolds/

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Links: Altimeter: https://www.altimeter.com/home

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Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

(0:00) Episode preview (0:38) Strategic investment and capital formation (3:13) Launching and evolving fund strategies (5:28) Identifying new capital sources (8:52) Educating investors in private markets (12:25) First movers advantage vs. track record (18:13) Reasons LPs leave a fund and the importance of transparency (23:00) Enhancing LP communication and trust (27:27) Building trust through transparency and empathy (29:06) Equity and involvement in investor relations (31:31) Streamlining LP communication with tools (33:18) Capital allocation strategies and diversification (37:06) Geographic diversification strategy (41:47) Accessing and developing new LP relationships (47:00) Leveraging media and social media for fundraising (51:05) Internal and external communication strategies (55:00) Insights for LPs and staying connected (56:52) Closing remarks

D.A. Wallach’s journey is one of the most unconventional paths in venture capital. He went from fronting a rock band discovered by Kanye West and Pharrell, to investing in Spotify, SpaceX, and founding a biotech VC firm reshaping human medicine. In this episode, we dive into his evolution—from artist to investor—and what he’s learned from being in the room with Mark Zuckerberg, Elon Musk, and Ron Burkle. D.A. shares why great investing is an act of taste, how he earned his first big break with Ron Burkle at Inevitable Ventures, and why he believes biotech is the most exciting place to invest over the next decade. We also discuss how aesthetic intuition applies to investing, how to think in second and third order effects, and what it really means to be contrarian when contrarianism has gone mainstream.

Highlights:

• How D.A. invested in SpaceX after meeting Elon Musk socially in LA
• Lessons from working with Spotify, including his invented role as “artist-in-residence”
• What he saw in Facebook in the early days and how he used it to grow his band
• How Kanye West and Pharrell discovered his music and launched his career
• The backstory behind raising capital for Spotify and meeting Ron Burkle
• What made Ashton Kutcher and D.A. uniquely valuable investors at the time
• Why he pivoted from tech into life sciences and started a healthcare-focused VC firm
• The importance of developing aesthetic judgment as an investor
• How to think about portfolio construction in biotech vs. software
• Why investing is mostly about people—and what pattern recognition D.A. uses
• The subtle power of learning from failures and “almost mistakes”
• How to be truly contrarian in an environment where contrarianism is trendy

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Guest Bio: D.A. Wallach is a venture capital investor and former recording artist. Discovered by Pharrell Williams while at Harvard, he toured with artists like Lady Gaga and Blink-182 and released music through Interscope and Capitol Records. In 2011, he shifted to investing, backing companies like Spotify, SpaceX, Ripple, and Neuralink. Today, he focuses on biotech and healthcare as co-founder of Time BioVentures. Named to Forbes' “30 Under 30” and Fast Company’s “100 Most Creative People,” D.A. also co-founded the Franca Fund for preventive genomics and appeared in the film La La Land.

Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com.

We’d like to thank @Republic for sponsoring this episode!

#VentureCapital #VC #Startups #OpenLP #AssetManagement

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Sponsor: Republic is the leading global investment platform making premier private market opportunities accessible to all investors. With over $3 billion deployed across its network of investment platforms, funds, and affiliated firms, Republic opens the door to new asset classes typically reserved for institutional investors such as—private equity, venture capital, and even sports teams and your favorite film producers.

All securities, including the Hamilton Lane’s Private Infrastructure Fund, are offered through affiliate Republic Broker-Dealer, OpenDeal Broker LLC Member FINRA & SiPC. All securities come with specific risks not limited to a total loss of your investment. Past performance is not indicative of future results. Please review the risks specific to this investment on the HLPIF deal page hosted on http://republic.com/hlpif.

--

Stay Connected: Twitter: David Weisburd: @dweisburd

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ D.A. Wallach: https://www.linkedin.com/in/dawallach/

Links Time BioVentures: https://www.timebioventures.com/

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Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

(0:00) Episode preview (2:00) Elon Musk's early views on AI and building SpaceX (4:18) Transition from music to investing and collaboration with Spotify (7:17) Leveraging Facebook for a band’s success and networking strategies (12:06) Mark Zuckerberg's early projects and the rise of Facebook (14:39) Contrarianism and its role in modern investing (19:22) How a music background influences investment decisions (22:32) Working with Ron Burkle and Inevitable Ventures (27:17) The journey of learning venture capitalism (30:10) Assessing higher-order effects in investments (31:52) The critical importance of investing in people (33:17) Diving into healthcare and biotech investing (36:46) Portfolio strategies in biotech versus traditional venture capital (39:38) How to compete with major biotech firms (44:40) The advantages of being surrounded by top performers (46:58) Learning from near-misses and investment failures (48:25) Closing remarks

Jim Bethea oversees $1.7 billion at the University of Iowa’s endowment—and he does it with a team of just five people. In this episode, we cover how Jim thinks about asset allocation, governance, manager selection, and why Iowa has decided to specialize in certain asset classes like lower middle market private equity. This conversation is full of nuance, clarity, and hard-earned lessons that every allocator, GP, and fund manager will benefit from. Jim pulls back the curtain on how small teams can still invest in niche, high-performing funds, how to manage investment committee dynamics, and why more isn't always better when it comes to diversification.

Highlights:

• The pros and cons of managing a $1.7B portfolio with a lean team
• Why Iowa focuses on areas where they can outperform by 300 to 1,000 basis points
• How to evaluate a new asset class and build relationships with experts
• The myth of diversification and why over-diversification is often expensive beta
• Jim’s philosophy on manager selection—and why governance matters more than most realize
• How incentives (or lack thereof) impact committees and investment staff
• The discipline embedded in illiquidity and why private markets can help prevent bad decisions
• Why Iowa prefers smaller private equity funds and the edge in lower middle market
• A candid discussion on when to re-up with top performers and when to walk away
• Jim’s take on fund-of-funds, venture exposure, and building a durable investment operation in Iowa City

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Guest Bio: Jim Bethea is the Chief Investment Officer at the University of Iowa Foundation, where he manages a $1.7 billion endowment. With over 15 years at Iowa and a deep background in both consulting and investment banking, Jim has crafted a concentrated strategy that punches well above its weight. He’s a respected voice among endowment CIOs and a strong advocate for information-sharing and collaborative learning in the LP community.

Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com.

We’d like to thank @Republic and @Carta for sponsoring this episode!

#VentureCapital #VC #Startups #OpenLP #AssetManagement

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Sponsor: Republic is the leading global investment platform making premier private market opportunities accessible to all investors. With over $3 billion deployed across its network of investment platforms, funds, and affiliated firms, Republic opens the door to new asset classes typically reserved for institutional investors such as—private equity, venture capital, and even sports teams and your favorite film producers.

All securities, including the Hamilton Lane’s Private Infrastructure Fund, are offered through affiliate Republic Broker-Dealer, OpenDeal Broker LLC Member FINRA & SiPC. All securities come with specific risks not limited to a total loss of your investment. Past performance is not indicative of future results. Please review the risks specific to this investment on the HLPIF deal page hosted on http://republic.com/hlpif.

Sponsor: At Carta, we’re on a mission to connect the participants in private capital — from investors and LPs to their portfolio companies — through a suite of financial intelligence and reporting software that’s purpose-built for venture capital and private equity. Since 2018, we’ve been empowering GPs, CFOs, and CEOs to escape obsolete systems of disconnected FP&A tools — all in favor of a single, unified software suite that helps them make impactful strategic decisions and deliver outstanding results for their investors. Learn more at: www.carta.com/fundtax

--

Stay Connected: X / Twitter: David Weisburd: @dweisburd

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Jim Bethea: https://www.linkedin.com/in/jim-bethea-cfa-caia-b90302177/

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Links: IOWA: https://uiowa.edu/

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Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

(0:00) Episode preview (2:41) Deciding on new asset classes and information bartering (7:05) Governance and its impact on investment returns (11:11) The role of investment committees and incentives (20:50) Analyzing top and bottom performers in portfolios (24:15) Educating the investment committee and higher concentration strategies (30:28) Co-investment interest and its impact on due diligence (32:14) Diversification versus concentrated portfolio risk and consultant incentives (37:49) Lessons from past market cycles and using fund of funds (42:13) Picking asset classes for alpha and time commitment in underwriting (44:06) Balancing alpha-generation with indexing in public equities (47:05) Liquidity considerations: Asset or liability? (51:00) Behavioral finance and maintaining investment discipline (55:26) Evaluating private equity returns in a competitive market (1:00:12) Specializing in lower middle market private equity and associated risks (1:07:51) Private credit investment climate and technical default issues (1:08:09) Overcoming early challenges and importance of in-house knowledge (1:09:39) Relationship dynamics between GPs and LPs and understanding underperformance (1:10:36) Turnaround stories and the value of investing in smaller funds (1:11:31) Closing remarks

In this thought-provoking debut episode of Turpentine VC, Erik sat down with Ben Horowitz, Co-Founder of Andreessen Horowitz, to explore the evolving landscape of venture capital, leadership, and the future of innovation. Ben shares his insights on navigating market cycles, building resilient companies, and the role of culture in long-term success. This conversation, recorded live at a16z’s Menlo Park offices in 2023, is packed with practical wisdom and candid stories from one of Silicon Valley’s most influential investors.

Highlights:

• VC Market Insights: Ben’s perspective on the current venture capital landscape and how it compares to previous cycles.
• Leadership Lessons: How to manage effectively during uncertain times and build resilient companies.
• Founder Resilience: The key traits that drive founders to succeed and how to foster resilience.
• Company Culture: Why culture is a competitive advantage and how to build a strong one.
• Investment Strategy: Insights into Andreessen Horowitz's approach to finding and backing standout startups.
• Future Trends: Ben’s predictions on AI, crypto, and other emerging technologies.

Guest Bio: Ben Horowitz is a Co-Founder and General Partner at Andreessen Horowitz (a16z), one of the most prominent venture capital firms in Silicon Valley. He is also the author of best-selling books "The Hard Thing About Hard Things" and "What You Do Is Who You Are." With decades of experience as an entrepreneur, CEO, and investor, Ben is a leading voice in the startup and VC ecosystem.

Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com.

We’d like to thank @OldCityInvestmentPartners and @Republic for sponsoring this episode!

#VentureCapital #VC #Startups #OpenLP #AssetManagement – Sponsor: Alpha on the Delta is a captivating, invitation-only alternative investment conference held during New Orleans' legendary JazzFest. Now in its third year, it brings together 150 institutional LPs, 30 leading GPs, and visionary entrepreneurs for a dynamic experience of knowledge sharing, relationship building, and cultural celebration.

The carefully curated agenda features engaging panel discussions with industry leaders, facilitated 1:1 meetings, and exciting social events showcasing the vibrant spirit of New Orleans. Attendees also enjoy access to Weekend 2 of JazzFest, offering an unforgettable blend of world-class music, cuisine, and connections. With limited attendance, Alpha on the Delta fosters meaningful relationships and transformative insights in an unparalleled setting.

Join us for a packed agenda spanning the Alternative Investment industry, music, and world-class cuisine. Visit http://HowIInvestDelta.com.

Sponsor: Republic is the leading global investment platform making premier private market opportunities accessible to all investors. With over $3 billion deployed across its network of investment platforms, funds, and affiliated firms, Republic opens the door to new asset classes typically reserved for institutional investors such as—private equity, venture capital, and even sports teams and your favorite film producers.

All securities, including the Hamilton Lane’s Private Infrastructure Fund, are offered through affiliate Republic Broker-Dealer, OpenDeal Broker LLC Member FINRA & SiPC. All securities come with specific risks not limited to a total loss of your investment. Past performance is not indicative of future results. Please review the risks specific to this investment on the HLPIF deal page hosted on http://republic.com/hlpif.

–

Stay Connected: X / Twitter: David Weisburd: @dweisburd

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/

Links: Andreessen Horowitz (a16z): https://a16z.com/ Subscribe to Turpentine VC: https://link.chtbl.com/TurpentineVC – Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.

(0:00) Episode preview (1:48) Andreessen Horowitz's structure vs. Y Combinator's approach (4:25) Evolution and public consideration of venture firms (8:15) Alignment issues with venture firms going public (9:38) Fund sizes, market opportunities, and talent retention (15:24) Governance and future trends in venture capital (20:14) Ben Horowitz on technology trends and AI strategy (24:30) Web 3, AI development, and crypto regulatory challenges (29:18) Venture vs. multi-asset firms and LP relations (31:16) Firm strategy influenced by macro factors (32:13) Advice for aspiring venture capitalists and wartime mindset (35:53) Technology optimism and building a tech media company (39:05) Media's impact on tech and concerns about AI power concentration (41:16) Decentralizing power and closing thoughts (41:31) Closing remarks

Paul Chai’s journey from first-generation immigrant to Chief Investment Officer of a $1 billion endowment is anything but conventional. In this episode, we unpack how he transitioned from aerospace engineering to managing capital, his approach to investing in “outsiders,” and the delicate balance of taking risk in hedge funds, GP stakes, and tactical trades like TALF 2.0. Paul shares how Kansas State University's endowment supports the school’s mission, why they invest in lower middle market buyouts and small hedge funds, and how they find and evaluate emerging managers.

Highlights: How being a first-generation immigrant shaped Paul’s investment philosophy

Why Kansas State backs outsiders—and what they look for in emerging managers

The TALF 2.0 trade that returned 8% in 6 months—4x the bond index

How small hedge funds and lower middle market buyouts can deliver outsized alpha

Kansas State’s 3-bucket portfolio structure: growth, diversifiers, and liquidity

Why investing in people is Kansas State’s highest-ROI strategy

Guest Bio: Paul Chai is the Chief Investment Officer of the Kansas State University Foundation, where he manages the school’s $1 billion endowment. A former aerospace engineer and consultant, Paul was recruited into investing by his college roommate and spent 12 years at a family office before joining Kansas State. He leads the investment team’s efforts across public and private equity, hedge funds, tactical strategies, and more — all while supporting the university’s mission of accessible, affordable education. Paul is a first-generation immigrant and an MIT graduate.

Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at david@weisburdcapital.com.

We’d like to thank Carta, Republic and Old City Investment Partners for sponsoring this episode!

#VentureCapital #VC #Startups #OpenLP #AssetManagement

Sponsor: Republic is the leading global investment platform making premier private market opportunities accessible to all investors. With over $3 billion deployed across its network of investment platforms, funds, and affiliated firms, Republic opens the door to new asset classes typically reserved for institutional investors such as—private equity, venture capital, and even sports teams and your favorite film producers.

All securities, including the Hamilton Lane’s Private Infrastructure Fund, are offered through affiliate Republic Broker-Dealer, OpenDeal Broker LLC Member FINRA & SiPC. All securities come with specific risks not limited to a total loss of your investment. Past performance is not indicative of future results. Please review the risks specific to this investment on the HLPIF deal page hosted on http://republic.com/hlpif.

Sponsor: At Carta, we’re on a mission to connect the participants in private capital — from investors and LPs to their portfolio companies — through a suite of financial intelligence and reporting software that’s purpose-built for venture capital and private equity. Since 2018, we’ve been empowering GPs, CFOs, and CEOs to escape obsolete systems of disconnected FP&A tools — all in favor of a single, unified software suite that helps them make impactful strategic decisions and deliver outstanding results for their investors. Learn more at: www.carta.com/fundtax

Sponsor: Alpha on the Delta is a captivating, invitation-only alternative investment conference held during New Orleans' legendary JazzFest. Now in its third year, it brings together 150 institutional LPs, 30 leading GPs, and visionary entrepreneurs for a dynamic experience of knowledge sharing, relationship building, and cultural celebration.

The carefully curated agenda features engaging panel discussions with industry leaders, facilitated 1:1 meetings, and exciting social events showcasing the vibrant spirit of New Orleans. Attendees also enjoy access to Weekend 2 of JazzFest, offering an unforgettable blend of world-class music, cuisine, and connections. With limited attendance, Alpha on the Delta fosters meaningful relationships and transformative insights in an unparalleled setting.

Join us for a packed agenda spanning the Alternative Investment industry, music, and world-class cuisine. Visit http://HowIInvestDelta.com.

Stay Connected:

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd Paul Chai: https://www.linkedin.com/in/ppchai/

Links Kansas State University Foundation: https://ksufoundation.org/

(0:00) Episode preview (2:44) Building connections and motivation in fund managers (6:04) Mutual value in manager relationships and balancing manager size (9:18) Tactical investment approach, TALF 2.0 trade, and partnering with nimble managers (13:09) Trust with the board and significance of TALF 2.0 trade (16:11) Portfolio leverage, diversifiers, and hedge fund strategies (20:11) Measuring portfolio diversification and the quarterly review process (23:41) Re-underwriting and portfolio structure with investment categories (27:36) Target return, portfolio levers, and dislocation opportunities (30:59) GP stakes, endowment strategy, and managing risk with smaller fund managers (37:16) Advantages of smaller hedge funds and Kansas State's investment strategies (42:12) Personal mission and Kansas State's impact (43:22) Closing remarks

Blake Scholl started with a crazy idea: bring back supersonic flight. A decade later, Boom Supersonic pre-orders from the likes of Virgin, United, and American Airlines, and is building the fastest commercial jet since the Concorde—without the sonic boom. But what looks like an inevitable success now was, at the beginning, a nearly laughable dream. In this episode, we break down how Blake went from crashing a Virgin Galactic rollout to pitching Richard Branson over breakfast, to getting a “yes” 24 hours before Y Combinator Demo Day. It’s a masterclass in high-agency entrepreneurship and building something audacious from first principles. From pitching billionaires to proving physics, from engineering emotional payoff for teams to raising capital from LPs directly, Blake unpacks how to build hard tech companies that actually work. If you’re a founder, builder, or dreamer, this one’s for you.

Highlights: Crashing Richard Branson’s party (literally) — and landing Virgin’s $2B commitment 24 hours before Demo Day

How Blake turned a cardboard prototype into a billion-dollar narrative

The best startup pitch ever to a billionaire: “I’m not asking for money, just the first 10 planes.”

Boom's first supersonic jet XB-1: how it was built, what it taught, and why it’s a game-changer

Why burnout isn’t working too hard—it’s working too long without emotional payoff

Boom’s path to proving “boomless” flight—and why that could unlock coast-to-coast supersonic travel

How Boom raised capital by skipping VCs and going straight to LPs

Why the market for supersonic flights could be bigger and more profitable than subsonic

The lesson from Uber, jets, and the Beatles: when you shorten time, you grow the market

Blake’s advice to hardware founders: “Don’t start with Starship. Start with Falcon 1.”

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Guest Bio: Blake Scholl is the Founder and CEO of Boom Supersonic, the company building the world’s fastest commercial airliner. Prior to Boom, Blake worked at Amazon and was part of the early team at Groupon. He’s raised hundreds of millions from bold investors like Reid Hoffman, Michael Moritz, and Y Combinator, and he’s built Boom into a company that could transform the future of global mobility.

Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at dweisburd@gmail.com.

We’d like to thank @Republic and @OldCityInvestmentPartners for sponsoring this episode!

#VentureCapital #VC #Startups #OpenLP #AssetManagement

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Sponsor: Alpha on the Delta is a captivating, invitation-only alternative investment conference held during New Orleans' legendary JazzFest. Now in its third year, it brings together 150 institutional LPs, 30 leading GPs, and visionary entrepreneurs for a dynamic experience of knowledge sharing, relationship building, and cultural celebration.

The carefully curated agenda features engaging panel discussions with industry leaders, facilitated 1:1 meetings, and exciting social events showcasing the vibrant spirit of New Orleans. Attendees also enjoy access to Weekend 2 of JazzFest, offering an unforgettable blend of world-class music, cuisine, and connections. With limited attendance, Alpha on the Delta fosters meaningful relationships and transformative insights in an unparalleled setting.

Join us for a packed agenda spanning the Alternative Investment industry, music, and world-class cuisine. Visit http://HowIInvestDelta.com.

Sponsor: Republic is the leading global investment platform making premier private market opportunities accessible to all investors. With over $3 billion deployed across its network of investment platforms, funds, and affiliated firms, Republic opens the door to new asset classes typically reserved for institutional investors such as—private equity, venture capital, and even sports teams and your favorite film producers.

All securities, including the Hamilton Lane’s Private Infrastructure Fund, are offered through affiliate Republic Broker-Dealer, OpenDeal Broker LLC Member FINRA & SiPC. All securities come with specific risks not limited to a total loss of your investment. Past performance is not indicative of future results. Please review the risks specific to this investment on the HLPIF deal page hosted on http://republic.com/hlpif.

--

Stay Connected: X / Twitter: David Weisburd: @dweisburd Blake Scholl: @bscholl

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Blake Scholl: https://www.linkedin.com/in/blakescholl/

Links: Boom Supersonic: https://boomsupersonic.com/

--

Questions or topics you want us to discuss on How I Invest? Email us at dweisburd@gmail.com.

(0:00) Episode preview (0:18) Efforts to repeal regulations and pitching to Richard Branson (2:23) Sales strategies, initial LOIs, and gaining credibility (3:51) Crashing Virgin Galactic's rollout and securing a deal with Richard Branson (7:48) Lessons for hardware founders, market validation, and the XB-one prototype (12:29) Overcoming technological barriers in supersonic flight (13:36) Comparison with SpaceX's incremental approach (18:22) Focusing milestones in the early years (19:23) Recruiting top talent and capital misconceptions for hardware companies (23:09) Profitability and competitive advantage in the airline industry (25:57) Regulatory landscape and supersonic flight over land (32:25) The importance of in-person meetings and future travel accessibility plans (34:06) Lessons learned from building Boom and advice for hardware entrepreneurs (39:02) Mission success events and emotional payoff (45:27) The role of ego in setting audacious goals (46:39) Timeline for Boom's supersonic jets and curating the right investor base (50:09) Closing remarks

In this episode of How I Invest, Evan Fisher, Founder of Portal Ventures, shares his expertise in fundraising, venture capital, and deal flow. He discusses the key elements of successful fundraising, how to craft a compelling pitch, and what investors look for when evaluating opportunities. Evan’s insights provide valuable lessons for both founders seeking capital and investors looking for high-quality deals.

Highlights: Fundraising Strategies: How founders can secure funding more effectively.

Pitch Deck Secrets: What makes a pitch deck stand out to investors.

Venture Capital Insights: How investors analyze deal flow and make investment decisions.

Emerging Investment Trends: The future of startup fundraising.

Building Relationships: The role of trust and networking in venture capital.

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Guest Bio: Evan Fisher is the Founder of Portal Ventures, a firm specializing in helping startups secure funding through strategic advisory and pitch deck optimization. With a background in investment banking and venture capital, Evan has helped companies across various industries raise significant capital. His deep understanding of investor psychology and storytelling makes him a sought-after advisor for high-growth startups.

Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at dweisburd@gmail.com.

We’d like to thank @Carta, @OldCityInvestmentPartners and @Republic for sponsoring this episode!

#VentureCapital #VC #Startups #OpenLP #AssetManagement

Sponsor: Republic is the leading global investment platform making premier private market opportunities accessible to all investors. With over $3 billion deployed across its network of investment platforms, funds, and affiliated firms, Republic opens the door to new asset classes typically reserved for institutional investors such as—private equity, venture capital, and even sports teams and your favorite film producers.

All securities, including the Hamilton Lane’s Private Infrastructure Fund, are offered through affiliate Republic Broker-Dealer, OpenDeal Broker LLC Member FINRA & SiPC. All securities come with specific risks not limited to a total loss of your investment. Past performance is not indicative of future results. Please review the risks specific to this investment on the HLPIF deal page hosted on www.republic.com/hlpif.

Sponsor: At Carta, we’re on a mission to connect the participants in private capital — from investors and LPs to their portfolio companies — through a suite of financial intelligence and reporting software that’s purpose-built for venture capital and private equity. Since 2018, we’ve been empowering GPs, CFOs, and CEOs to escape obsolete systems of disconnected FP&A tools — all in favor of a single, unified software suite that helps them make impactful strategic decisions and deliver outstanding results for their investors. Learn more at: www.carta.com/howiinvest.

Sponsor: Alpha on the Delta is a captivating, invitation-only alternative investment conference held during New Orleans' legendary JazzFest. Now in its third year, it brings together 150 institutional LPs, 30 leading GPs, and visionary entrepreneurs for a dynamic experience of knowledge sharing, relationship building, and cultural celebration.

The carefully curated agenda features engaging panel discussions with industry leaders, facilitated 1:1 meetings, and exciting social events showcasing the vibrant spirit of New Orleans. Attendees also enjoy access to Weekend 2 of JazzFest, offering an unforgettable blend of world-class music, cuisine, and connections. With limited attendance, Alpha on the Delta fosters meaningful relationships and transformative insights in an unparalleled setting.

Join us for a packed agenda spanning the Alternative Investment industry, music, and world-class cuisine. Visit http://HowIInvestDelta.com.

--

Stay Connected: X / Twitter: David Weisburd: @dweisburd Evan Fisher: @evanbfish

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Evan Fisher: https://www.linkedin.com/in/evanfisher1/

Links: Portal Ventures: https://portal.vc/

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Questions or topics you want us to discuss on How I Invest? Email us at dweisburd@gmail.com.

(0:00) Episode preview (1:24) Crypto's new asset classes and first-check advantages (3:52) Reinventing in the fast-evolving crypto industry (8:07) Developing thematic bets and the Bitcoin economy thesis (14:00) Market size evaluation and strategic partnerships (15:51) Post-investment founder support and proprietary deals (18:19) Co-investing risks and analyzing investment failures (19:52) MEV space exploration and decentralized science (DeSci) (24:42) Comparing crypto and biotech investing strategies (26:29) Early investment signals and partner dynamics (31:21) Long-term crypto survival strategies (35:04) LP interest in crypto and its liquidity profile (37:19) Bitcoin's continued dominance and future trends (41:09) Closing remarks

In this episode of How I Invest, Billy Libby, Co-Founder and CEO of Upper90, discusses how his firm is redefining venture capital through a hybrid investment model that combines equity and credit. He shares how Upper90 empowers founders to scale without excessive dilution and offers insights into navigating today’s venture landscape. Billy’s approach to alternative financing provides valuable lessons for entrepreneurs and investors alike.

Highlights: Alternative Financing: How Upper90's unique blend of equity and credit helps founders grow without giving up control.

Venture Capital Insights: Billy's perspective on the changing dynamics of the VC world.

Supporting Founders: The importance of aligning incentives between investors and entrepreneurs.

Navigating Market Cycles: Lessons from managing capital through different economic environments.

Growth Stories: Real-world examples of companies that benefited from Upper90's approach.

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Guest Bio: Billy Libby is the Co-Founder and CEO of Upper90, a leading hybrid investment firm providing both equity and credit to high-growth companies. With a background in trading and risk management, Billy leverages data-driven strategies to support founders in building successful, sustainable businesses. Upper90 has backed numerous successful startups and continues to innovate in the venture capital landscape.

Our podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at dweisburd@gmail.com.

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Stay Connected: X / Twitter: David Weisburd: @dweisburd

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Billy Libby: https://www.linkedin.com/in/billy-libby-76464b1/

Links: Upper90: https://upper90.io/

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Questions or topics you want us to discuss on How I Invest? Email us at dweisburd@gmail.com.

(0:00) Episode preview (2:37) Startups' perception of credit usage and structuring investments in new theses like NVIDIA chips (6:27) When startups should consider credit versus equity and the financial metrics required (9:22) Seasoning process for financial instruments and capital availability (12:12) Impact of macroeconomic cycles on capital deployment (17:36) Network-driven fundraising, time management, and investor relations (20:23) Institutional practices for transitioning between funds (24:05) Equity flavor in private credit and catalysts for institutional investors (26:17) Hiring strategy, rationale for early hiring, and diversification (29:56) Consistency in returns and addressing lack of diversification (31:14) Closing remarks

In this episode of How I Invest, Aaron Hodari, Managing Director at Schechter, delves into the world of wealth management and alternative investments. He shares how his firm navigates market uncertainties, crafts resilient portfolios, and uncovers unique opportunities for high-net-worth clients. Aaron's insights provide valuable lessons for investors seeking to optimize their financial strategies.

Highlights: Alternative Investments: How Schechter incorporates alternative assets to diversify and strengthen portfolios.

Tailored Wealth Management: The firm's approach to creating personalized investment strategies for clients.

Market Insights: Aaron's perspectives on navigating economic uncertainty and market volatility.

Private Equity and Credit Markets: The role these asset classes play in long-term financial growth.

Career Lessons: Aaron's key takeaways from years of experience in wealth management.

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Guest Bio: Aaron Hodari serves as Managing Director at Schechter, a leading wealth advisory and financial services firm. With deep expertise in alternative investments and comprehensive portfolio management, Aaron works with clients to protect and grow their wealth across generations.

Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at dweisburd@gmail.com.

We’d like to thank @Carta for sponsoring this episode!

#VentureCapital #VC #Startups #OpenLP #AssetManagement

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Sponsor: At Carta, we’re on a mission to connect the participants in private capital — from investors and LPs to their portfolio companies — through a suite of financial intelligence and reporting software that’s purpose-built for venture capital and private equity. Since 2018, we’ve been empowering GPs, CFOs, and CEOs to escape obsolete systems of disconnected FP&A tools — all in favor of a single, unified software suite that helps them make impactful strategic decisions and deliver outstanding results for their investors. Learn more at: www.carta.com/howiinvest.

--

Stay Connected: X / Twitter: David Weisburd: @dweisburd

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Aaron Hodari: https://www.linkedin.com/in/aaronhodari/

Links: Schechter: https://www.schechterwealth.com/

Questions or topics you want us to discuss on How I Invest? Email us at dweisburd@gmail.com.

(0:00) Episode preview (3:01) Diversification and tax optimization for founders (8:20) Estate planning: Control and management of funds (10:34) Sponsor: Tactic by Carta (11:41) Passion, purpose, and income tax planning (19:02) Comprehensive look at long-short strategies (24:37) Strategic tax planning and gifting assets (28:42) Understanding tracking error in tax loss harvesting (32:57) Overview of the private credit market (36:17) Exploring middle market direct lending (39:45) General Partner lending and financing insights (41:56) Interval funds: benefits, fee structures, and tax efficiency (49:38) Closing remarks

In this episode of How I Invest, Logan Allin, Managing Partner and Founder of Fin Capital, shares how his firm uses AI-powered predictive models to evaluate startups. We explore how AI can assess founder DNA, predict billion-dollar outcomes, and transform the venture capital landscape. Logan also highlights the surprising traits that lead to startup success, the advantages of repeat founders, and what the future holds for fintech. This conversation offers valuable insights for investors, entrepreneurs, and anyone fascinated by the intersection of AI and venture capital.

Highlights: AI-Driven Investing: How Fin Capital uses generative AI to predict startup success with up to 90% certainty at the seed and Series A stages.

Founder DNA: The 35 key factors Fin Capital assesses to evaluate founder potential, including surprising insights on prior CEO experience.

Repeat Founders Win: Why founders with prior exits are more likely to build billion-dollar companies and how data supports this trend.

Beyond the University Label: Why prestigious degrees don’t significantly predict startup success.

Fintech Focus: How specializing in fintech gives Fin Capital a competitive edge in sourcing and supporting founders.

Evolving AI Models: The role of continuous backtesting and data refinement in improving prediction accuracy.

The Future of Fintech: Logan’s predictions on the next wave of fintech innovation and how AI will continue to shape venture capital.

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Guest Bio: Logan Allin is the Managing Partner and Founder of Fin Capital, a leading fintech investment firm. With extensive experience in venture capital, Logan has built Fin Capital into a data-driven powerhouse focused on backing repeat founders and disruptive fintech companies. He is a passionate advocate for AI-driven decision-making in venture investing and a recognized thought leader in the fintech ecosystem.

Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at dweisburd@gmail.com.

#VentureCapital #VC #Startups #OpenLP #AssetManagement

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Stay Connected Twitter: David Weisburd: @dweisburd

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Logan Allin: https://www.linkedin.com/in/loganallin/

Links Fin Capital: https://www.linkedin.com/company/fin-capital-fintech/

-- Questions or topics you want us to discuss on How I Invest? Email us at dweisburd@gmail.com.

(0:00) Episode preview (3:04) Founder DNA and success archetypes (7:00) Utilizing AI and tracking stealth companies (10:46) Reverse reference calls and competing with top firms (16:09) Specialization in fintech (17:35) Hiring a head of AI and building a strategic LP base (24:25) Evolving investor relations strategy (26:48) Decision making on post-lockup shareholding (29:42) Scaling to a billion dollars in AUM (35:19) Investing in emerging managers (37:02) Lessons from SoFi for Fin Capital operations (39:25) Closing remarks

In this episode of How I Invest, I speak with Brendon Parry, Head of Private Markets, Deputy CIO, and Managing Director at TIFF Investment Management. Brendon shares insights on TIFF’s mission to serve nonprofit institutions through tailored investment solutions. He discusses the importance of private market investments, the legacy of leaders like David Swensen, and how TIFF partners with foundations to achieve long-term financial goals. Tune in for actionable strategies and valuable perspectives from a seasoned investment professional.

Disclaimer: Brendon Parry, CFA, is the Head of Private Markets, Deputy CIO at TIFF Investment Management. All views expressed by him on this podcast are solely his opinions and do not reflect the opinions of TIFF. You should not treat any opinions expressed by Brendon as a specific endorsement to make a particular investment. References to any securities are for informational purposes only and do not constitute an investment recommendation or offer to provide investment advisory services. Any past performance discussed is not indicative of future results. Please keep in mind that investment in a fund entails a high degree of risk, including the risk of loss. Please note that the ads featured in this podcast are not endorsed by TIFF, and TIFF is not a sponsor of these ads.

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Highlights: TIFF’s Mission: How TIFF Investment Management supports nonprofits with specialized investment solutions.

Private Markets Expertise: Insights into early-stage venture capital, lower middle market buyout, and growth equity investments.

Partnership Approach: How TIFF collaborates with nonprofits of various sizes to customize portfolios and deliver long-term returns.

Legacy of Leadership: The influence of David Swensen, former Yale CIO, on TIFF’s investment philosophy.

Risk Management: Strategies for balancing risk and reward in complex market environments.

Career Insights: Lessons from Brendon’s journey in private equity and investment management.

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Guest Bio: Brendon Parry is the Head of Private Markets, Deputy CIO, and Managing Director at TIFF Investment Management. He has been with TIFF since 2011, leading the firm's private markets initiatives with a focus on early-stage venture capital, lower middle market buyout, and growth equity. Before TIFF, Brendon worked at Providence Equity Partners and Cambridge Associates. He holds an AB in Economics from Brown University and an MBA from Harvard Business School. With a passion for helping nonprofits achieve their financial goals, Brendon plays a key role in TIFF’s mission.

Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at dweisburd@gmail.com.

We’d like to thank @Carta for sponsoring this episode!

#VentureCapital #VC #Startups #OpenLP #AssetManagement

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Sponsor: At Carta, we’re on a mission to connect the participants in private capital — from investors and LPs to their portfolio companies — through a suite of financial intelligence and reporting software that’s purpose-built for venture capital and private equity. Since 2018, we’ve been empowering GPs, CFOs, and CEOs to escape obsolete systems of disconnected FP&A tools — all in favor of a single, unified software suite that helps them make impactful strategic decisions and deliver outstanding results for their investors. Learn more at: carta.com/howiinvest.

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Stay Connected: X / Twitter: David Weisburd: @dweisburd

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Brendon Parry: https://www.linkedin.com/in/brendon-parry-77a5677/

Links: TIFF Investment Management: https://www.tiff.org/private-markets/

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Questions or topics you want us to discuss on How I Invest? Email us at dweisburd@gmail.com.

(0:00) Episode preview (2:06) TIFF's mission and partnership with foundations (4:01) TIFF's investment strategies with a focus on private markets (7:01) Reasons for focusing on lower middle market and early stage VC (9:02) Sponsor: Tactic by Carta (10:09) Risk assessment in lower middle market PE vs. larger PE (23:11) Historical performance comparison: fund ones vs. fund twos (24:42) Diligence process for independent sponsors (27:01) Coordinating sponsor and deal diligence teams (27:37) Organizational changes and lessons from 14 years at TIFF (32:05) Building an antifragile portfolio and the confidence paradox in investing (37:31) Predicting the future and core principles in manager selection (41:35) Closing remarks

In this episode of How I Invest, I dive deep into a conversation with Charlotte Zhang of Inatai Foundation. Charlotte shares her approach to managing a $2.4 billion private investment program, the importance of market inefficiencies, and how she strategically builds GP relationships. We explore how Inatai identifies top managers, why LPs are increasingly interested in fundless sponsors, and what makes a great investment philosophy. Whether you're an LP, VC, or just curious about institutional investing, this episode is packed with insights on capital allocation, conviction-based investing, and long-term partnership building.

Highlights: Building a $2.4 Billion Investment Program: How Charlotte structured Inatai’s approach without rigid asset allocation targets.

GP Selection Strategy: The four P’s—People, Philosophy, Process, and Performance—that guide investment decisions. Market Inefficiencies & Innovation: Why Inatai prioritizes global opportunities in venture, buyout, and select real assets.

Fundless Sponsors: Why LPs are increasingly backing fundless sponsors and the advantages of doing so.

Investment Discipline: How to evaluate managers over time and avoid the pitfalls of FOMO-driven investing.

Handling Market Downturns: The characteristics of managers who thrive in turbulent markets.

The Role of LPs as Value-Added Partners: How LPs can help GPs beyond just providing capital.

Diversification vs. Concentration: How Inatai balances a high-conviction portfolio while maintaining risk-adjusted returns.

The Future of Inatai: How the foundation is expanding its impact through its outsourced CIO platform.

-- Guest Bio: Charlotte Zhang is a Senior Portfolio Manager at Inatai Foundation, where she leads private investments within the $2.4 billion portfolio. She has previously held roles at Medley Partners and Iconiq Capital, developing expertise in manager selection, portfolio construction, and market inefficiencies. Charlotte is passionate about long-term investing, identifying top-tier GPs, and fostering meaningful LP-GP relationships. Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at dweisburd@gmail.com.

#VentureCapital #VC #Startups #OpenLP #AssetManagement

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Stay Connected: X / Twitter: David Weisburd: @dweisburd

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Charlotte Zhang:https://www.linkedin.com/in/charlotterzhang/

Links: Inatai Foundation: https://inatai.org/

Questions or topics you want us to discuss on How I Invest? Email us at dweisburd@gmail.com.

(0:00) Episode preview (1:20) Creating and executing a lower middle market PE strategy (3:39) Spending years on investment decisions and handling market downturns (8:08) Exploring interest in fundless sponsors and largest deals (11:09) Inatay team structure and the generalist team approach (13:17) Managing infinite opportunities and diversification strategies (16:38) Sourcing and adding value to GP relationships (21:30) Closing remarks

In this episode of How I Invest, I sit down with Matt Fitzpatrick, CEO of Invisible Technologies and former head of McKinsey’s QuantumBlack Labs. Matt shares his deep insights on enterprise AI adoption, model fine-tuning, and the challenges businesses face when integrating AI into their workflows. We explore why only 8% of AI models make it to production, how enterprises can overcome friction points, and the future of AI-powered enterprise solutions. If you’re curious about the intersection of AI and business strategy, this episode is a must-listen.

Highlights: Enterprise AI Adoption: Why only 8% of AI models reach production and how companies can improve their success rates.

AI Fine-Tuning for Enterprises: The importance of domain-specific AI models and why general AI solutions don’t always fit enterprise needs.

The Data Challenge: Why poor data quality is the biggest barrier to AI adoption and how companies can fix it.

Human-AI Collaboration: The role of human feedback in training AI models for enterprise use cases.

Real-World AI Success Stories: How companies like Moody’s and Klarna successfully implemented AI solutions.

Invisible Technologies’ Vision: How Invisible is building an AI-powered enterprise services platform to modernize business operations.

Future of AI in Business: How AI-native companies will rethink workflows and software applications from the ground up. Matt’s Journey: From leading McKinsey’s AI lab to scaling one of the fastest-growing AI companies.

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Guest Bio: Matt Fitzpatrick is the CEO of Invisible Technologies, a rapidly growing AI-powered services company. Before joining Invisible, Matt led McKinsey’s QuantumBlack Labs, where he worked on large-scale AI and data transformation projects. He has extensive experience in enterprise AI adoption and has helped some of the world’s largest organizations modernize their operations using artificial intelligence.

Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at dweisburd@gmail.com.

We’d like to thank @Carta and @Daloopa for sponsoring this episode!

#VentureCapital #VC #Startups #OpenLP #AssetManagement

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Sponsor: At Carta, we’re on a mission to connect the participants in private capital — from investors and LPs to their portfolio companies — through a suite of financial intelligence and reporting software that’s purpose-built for venture capital and private equity. Since 2018, we’ve been empowering GPs, CFOs, and CEOs to escape obsolete systems of disconnected FP&A tools — all in favor of a single, unified software suite that helps them make impactful strategic decisions and deliver outstanding results for their investors. Learn more at: www.carta.com/howiinvest.

Sponsor: Daloopa uses AI to provide the best fundamental data service for equity analysts globally. Daloopa empowers users to automatically update existing models and expedite new model builds so that users can spend more time on insights and ideas. Accurate data is central to all investment decisions and can influence speed and confidence for decision-makers. Daloopa believes that AI technology can improve clarity and efficiency for investors and financial markets. Learn more at: www.daloopa.com/how.

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Stay Connected: X / Twitter: David Weisburd: @dweisburd

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Matt Fitzpatrick: https://www.linkedin.com/in/matthew-fitzpatrick-97b62722/

Links: Invisible Technologies: https://www.invisible.co/

Questions or topics you want us to discuss on How I Invest? Email us at dweisburd@gmail.com.

(0:00) Episode preview (1:46) Training vectors and core business components of Invisible Technologies (3:21) Successful enterprise models and future AI evolution (5:07) Challenges and evaluation of AI model deployment at scale (7:49) Human feedback and accuracy requirements in AI models (10:03) Fine-tuning AI models for enterprise applications (12:27) McKinsey's successful enterprise AI use cases (13:23) AI's impact on productivity and process redesign (15:39) Invisible Technologies' growth strategy and focus on enterprise fine-tuning (17:22) Building a modern ServiceNow with GenAI and avoiding obsolescence (18:26) Modernization of legacy systems and AI native application development (20:03) Shifting focus in the AI ecosystem and agentic layer (22:30) Comparing AI native CRM to traditional CRM systems (23:18) Invisible Technologies' future vision and optimism about enterprise AI (24:33) Closing remarks

In this episode of How I Invest, I interview Robert Cherun, an expert in search funds and small-cap investing. Robert shares his journey from launching his own search fund to building and exiting a highly successful business. We dive into the fundamentals of search funds, the economics of acquiring and scaling small businesses, and the key traits that make a successful searcher.

Highlights: What Is a Search Fund? How search funds enable entrepreneurs to acquire and grow established businesses with investor backing.

Impressive Returns: Search funds have historically generated 35% net IRRs and 4.5x ROI, making them a compelling investment strategy.

Barriers to Institutional Adoption: Despite high returns, institutional investors struggle to deploy capital effectively in this micro-cap space.

Search Fund Lifecycle: A breakdown of how searchers raise capital, find businesses, and structure acquisitions.

Portfolio Strategy: How Robert constructs a diversified portfolio of search fund investments to maximize returns.

TAM & Growth of Search Funds: How the space has evolved from niche to mainstream, with billions invested in recent years.

Traits of a Successful Searcher: The skills and qualities investors look for in entrepreneurs, from financial acumen to leadership ability.

Lessons from a $150M Exit: Robert’s journey from acquiring a $5M security business to scaling it into an industry leader with 2,000 employees.

The Asurion Story: A legendary search fund deal that delivered 100x–1,000x returns to early investors.

Search Funds vs. Startups: Why search funds offer a lower-risk path to entrepreneurship compared to venture-backed startups.

Co-CEO Model: Best practices for managing leadership dynamics and decision-making between business partners.

Governance & Investor Relations: How search fund investors maintain oversight while giving CEOs operational control.

Biggest Misconceptions About Search Funds: Why experience isn’t everything and how young entrepreneurs can successfully run businesses.

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Guest Bio: Robert Cherun is a leading investor in search funds and small-cap businesses. As the co-founder of a successful security company, he scaled the business from $5M to $150M in revenue before exiting to a strategic buyer. Now, through his firm Legate Partners, Robert invests in and mentors the next generation of search fund entrepreneurs. Passionate about small business transformation, Robert specializes in identifying high-potential searchers and helping them build industry-leading companies.

Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email me at dweisburd@gmail.com.

#VentureCapital #VC #Startups #OpenLP #AssetManagement

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Stay Connected: X / Twitter: David Weisburd: @dweisburd

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Robert Cherun: https://www.linkedin.com/in/robcherun/

Links: Legate Partners: https://www.legatelp.com/

Questions or topics you want us to discuss on How I Invest? Email us at dweisburd@gmail.com.

(0:00) Episode preview (0:51) Overview of search funds and historical returns (2:16) Capitalization and portfolio construction in search funds (3:26) Growth of search funds and searcher profiles (5:05) Comparing search funds with traditional startup models (7:37) UCIT Online Security acquisition journey and deal economics (10:22) Famous search fund deals and Legate Partners introduction (11:33) Legate Partners' strategy and CEO selection criteria (13:24) CEO profiles and co-CEO best practices (15:55) Governance and decision-making in search funds (17:44) Insights on search fund dynamics and governance (19:11) Transitioning from finance to search funds and key lessons (20:11) Final thoughts on team dynamics and search fund misconceptions (20:58) Closing remarks

In this special solo episode of How I Invest, I break down one of the most powerful forces in investing: compounding. Over the course of 142 episodes, I’ve discovered that the best investors all leverage compounding—not just in their portfolios but in every aspect of their business. From relationships and reputation to proprietary information and top talent, compounding creates exponential advantages in a hyper-competitive market.

Highlights:

Compounding Beyond Capital: The biggest investors understand that everything compounds, including reputation, diligence, and deal-making experience.

The Power of Relationships: Trust compounds with each deal, leading to faster and more efficient decision-making.

Reputation as an Asset: Warren Buffett’s ability to negotiate superior terms stems from his compounding reputation as an ethical and skilled investor.

Proprietary Information Loops: Access to unique insights leads to better investments, which generate even more privileged information.

People as a Compounding Advantage: The best organizations attract and retain A-players, who in turn recruit other top talent, creating a self-reinforcing cycle of excellence.

The Arbitrage of A-Players: Paying A-players above market rates is a competitive advantage, as they generate exponentially greater value.

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Stay Connected: X / Twitter: David Weisburd: @dweisburd

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/

Questions or topics you want us to discuss on How I Invest? Email us at dweisburd@gmail.com.

(0:00) Episode preview (0:21) The role of compounding in investing and relationships (2:13) Trust bias, deal-making efficiency, and reputation effects (4:23) Proprietary information and the compounding of talent (6:50) AI's impact on productivity and compounding (7:49) Closing remarks

In this episode of How I Invest, I interview Scott van den Berg, an expert in celebrity-founded brands and the managing partner of Hotstar VC. Scott shares deep insights into how celebrities are leveraging their platforms to build billion-dollar businesses and why some partnerships thrive while others fail. We discuss the shift in celebrity investments, the rise of creator-led brands, and key lessons from success stories like Ryan Reynolds' Mint Mobile, Kim Kardashian's Skims, and George Clooney's Casamigos.

Highlights: Lessons from Ryan Reynolds: How he strategically invested in "unsexy" industries and built massive brand value.

The Power of Celebrity-Led Brands: How stars like Kim Kardashian, Logan Paul, and Ryan Reynolds built billion-dollar companies.

Equity vs. Cash Deals: Why traditional talent managers prefer cash over equity and how this impacts startup partnerships.

Product-First Approach: The importance of having a strong product, even when backed by a celebrity.

Celebrity Product-Market Fit: Why aligning a celebrity's brand with the right product is crucial for success.

The Over saturation of Celebrity Tequila Brands: Why so many celebrities enter the liquor market and the real economics behind it.

The Rise of the Creator Economy: How influencers are turning their massive audiences into thriving businesses.

Avoiding Common Pitfalls: The biggest mistakes startups make when partnering with celebrities.

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Guest Bio: Scott van den Berg is the managing partner at Hotstar VC, a fund specializing in investments in celebrity and creator-led brands. With experience in 55 celebrity-founded businesses, Scott has worked with stars like Selena Gomez, DJ Khaled, and Jake Paul. His team includes co-founders of some of the most successful celebrity-led brands, such as The Honest Company and Feastables. As a thought leader in the space, Scott shares insights on how celebrities can build sustainable businesses and transform their influence into long-term value.

Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at dweisburd@gmail.com.

We’d like to thank @Carta and @Daloopa for sponsoring this episode!

#VentureCapital #VC #Startups #OpenLP #AssetManagement

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Sponsor: At Carta, we’re on a mission to connect the participants in private capital — from investors and LPs to their portfolio companies — through a suite of financial intelligence and reporting software that’s purpose-built for venture capital and private equity. Since 2018, we’ve been empowering GPs, CFOs, and CEOs to escape obsolete systems of disconnected FP&A tools — all in favor of a single, unified software suite that helps them make impactful strategic decisions and deliver outstanding results for their investors. Learn more at: www.carta.com/howiinvest.

Sponsor: Daloopa uses AI to provide the best fundamental data service for equity analysts globally. Daloopa empowers users to automatically update existing models and expedite new model builds so that users can spend more time on insights and ideas. Accurate data is central to all investment decisions and can influence speed and confidence for decision-makers. Daloopa believes that AI technology can improve clarity and efficiency for investors and financial markets. Learn more at: www.daloopa.com/how.

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Stay Connected: X / Twitter: David Weisburd: @dweisburd

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Scott Van den Berg: https://www.linkedin.com/in/scott-van-den-berg-22b534150/

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Links: HotStar VC: https://www.hotstart.vc/

Questions or topics you want us to discuss on How I Invest? Email us at dweisburd@gmail.com.

(0:00) Episode preview (5:01) Sponsor: Tactic Bicarda (6:20) Selecting and partnering with the right celebrity for a brand (9:09) Sponsor: The Loop (10:13) Navigating challenges with celebrity managers and agencies (13:10) Hotstar VC's methodology in celebrity-founded brand investments (16:43) Case studies of celebrity brand successes (18:31) Key takeaways from investing in celebrity-driven ventures (19:22) Closing remarks and upcoming episode teaser (20:15) Sponsor: Vanguard (23:45) Closing remarks

In this episode of How I Invest, I have a conversation with Scott Chan, Chief Investment Officer of CalSTRS, to explore how he oversees a staggering $350 billion in assets. Scott shares insights on CalSTRS’ collaborative investment model, their approach to private and public markets, and why they aim to be the "global partner of choice." We also discuss the importance of structural alpha, liquidity management, and identifying long-term supply-demand imbalances.

Highlights: The Collaborative Model: How CalSTRS brings more assets in-house to lower costs and increase control over risk and alpha.

Public vs. Private Markets: Why 80–85% of public market assets are managed internally while private investments rely on partnerships.

Becoming the Global Partner of Choice: Why being a top three call for GPs is crucial for accessing the best private market transactions.

Portfolio Allocation Strategy: How CalSTRS is shifting risk exposure toward private markets to enhance returns.

Contrarian Investing: Scott’s view on why the stock market may underperform over the next decade and where he sees better opportunities.

The Importance of Liquidity: Why liquidity will be "more valuable than gold" and how CalSTRS prepares for market downturns.

Identifying Supply-Demand Imbalances: Where CalSTRS sees long-term opportunities, from real estate to private credit and infrastructure.

Structural Alpha: How CalSTRS structures deals to generate uncorrelated alpha without taking additional market risk.

Governance and Decision-Making: How a nimble, delegated investment approach allows CalSTRS to act quickly on opportunities.

The Role of Team & Culture: Scott emphasizes why a strong leadership team is the ultimate competitive advantage.

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Guest Bio: Scott Chan is the Chief Investment Officer of CalSTRS, overseeing $350 billion in assets for over one million California teachers. With decades of experience in institutional investing, Scott has led CalSTRS in developing its collaborative investment model, focusing on cost efficiency, structural alpha, and strategic partnerships. His contrarian mindset and deep expertise help position CalSTRS as a global leader in asset management. Our Podcast now receives more than 200,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at dweisburd@gmail.com.

We’d like to thank @JuniperSquare for sponsoring this episode!

#VentureCapital #VC #Startups #OpenLP #AssetManagement

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Sponsor: Juniper Square is dedicated to transforming the private markets investing experience. The company provides a full range of modern, connected fund technologies and services for over 2,100 private markets GPs across fundraising, reporting, fund administration, treasury, compliance, and business intelligence. Today, over $1 trillion of assets and 600,000+ LP accounts are managed through Juniper Square software and fund administration services. Learn more at www.junipersquare.com.

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Stay Connected: X / Twitter: David Weisburd: @dweisburd

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Scott Chan: https://www.linkedin.com/in/chanscott/

Links: CalSTRS: https://www.calstrs.com/

Questions or topics you want us to discuss on How I Invest? Email us at dweisburd@gmail.com.

(0:00) Episode preview (1:09) Introduction to CalSTRS and collaborative investing (2:11) Public vs private markets and global partnerships at CalSTRS (5:26) Public and private market investment strategies (7:03) Collaborating with private managers and selecting GPs (11:41) Contrarian thinking and current investment focus (17:13) Liquidity management and market opportunities (18:19) Sponsor: Juniper Square (19:43) Liquidity options and alternative asset opportunities (21:31) Market crisis preparation and governance structure (26:30) Exploring structural alpha and capital base implications (31:20) Leveraging supply-demand imbalances in investing (35:58) Personal alignment and development as a CIO (40:29) Closing remarks

In this episode of How I Invest, I chat with Balaji Srinivasan—former CTO of Coinbase, General Partner at Andreessen Horowitz (a16z), and bestselling author of The Network State. Balaji shares his vision for how the internet could ultimately succeed America, the rise of network states, and the implications of Bitcoin's exponential growth. We discuss the future of digital governance, crypto democracy, and how decentralized technologies are reshaping global power structures. Whether you're a crypto investor, a technology enthusiast, or someone curious about the future of governance, this episode is packed with thought-provoking insights.

Highlights: The Internet as the Next Superpower: Just as America succeeded Britain, Balaji argues that the internet is on track to become the dominant global force.

Bitcoin vs. Fiat: Over the last decade, Bitcoin has appreciated by roughly 8% per month, while fiat currencies have consistently depreciated.

The Rise of Network States: Inspired by historical precedents like Israel, Singapore, and the American frontier, Balaji explains how digital communities can evolve into sovereign entities.

Crypto as Digital Government: Cryptocurrencies already provide key governmental functions—property rights, monetary policy, and dispute resolution—without traditional state infrastructure.

Decentralized Governance & DAOs: Online communities are allocating billions of dollars in funding through decentralized governance structures, challenging traditional political systems.

The Future of Democracy: Balaji discusses different models of democracy—Western, Indian, and crypto-democracy—and how blockchain technology can enhance governance.

The Balaji Fund & High-Risk Seed Investing: A look into Balaji’s new venture fund, backing radical technological innovation with an ideological edge.

Building at Internet Speed: Why traditional infrastructure development is stagnating, and how countries like China are achieving 1,000x efficiency improvements in construction.

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Guest Bio: Balaji Srinivasan is a renowned investor, entrepreneur, and futurist. He served as the CTO of Coinbase, was a General Partner at Andreessen Horowitz, and co-founded multiple startups, including Earn, Teleport, and Counsyl. His book, The Network State, became a bestseller and has inspired a new movement around digital governance and decentralized nation-building. Balaji is a thought leader on Bitcoin, crypto governance, and the future of technology-driven societies.

Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at dweisburd@gmail.com.

We’d like to thank @JuniperSquare and @Daloopa for sponsoring this episode!

#VentureCapital #VC #Startups #OpenLP #AssetManagement

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Sponsor: Juniper Square is dedicated to transforming the private markets investing experience. The company provides a full range of modern, connected fund technologies and services for over 2,100 private markets GPs across fundraising, reporting, fund administration, treasury, compliance, and business intelligence. Today, over $1 trillion of assets and 600,000+ LP accounts are managed through Juniper Square software and fund administration services. Learn more at www.junipersquare.com.

Sponsor: Daloopa uses AI to provide the best fundamental data service for equity analysts globally. Daloopa empowers users to automatically update existing models and expedite new model builds so that users can spend more time on insights and ideas. Accurate data is central to all investment decisions and can influence speed and confidence for decision-makers. Daloopa believes that AI technology can improve clarity and efficiency for investors and financial markets. Learn more at www.daloopa.com/how.

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Stay Connected: X / Twitter: David Weisburd: @dweisburd Balaji Srinivasan: @balajis

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Balaji Srinivasan: https://www.linkedin.com/in/balajissrinivasan/

Questions or topics you want us to discuss on How I Invest? Email us at dweisburd@gmail.com.

(0:00) Episode preview (0:58) Guest introduction and discussion on "The Network State" (2:18) Network states: examples and historical precedents (4:46) Network states vs. traditional countries and the internet's role (9:19) Social media's political impact and cryptocurrency's economic influence (12:07) Sponsor: Juniper Square (13:25) Bitcoin and cryptocurrencies' influence on governance and fiat currencies (18:26) The future of democratic capitalism and its different forms (22:09) Capitalism and democracy through the ages (24:02) Digital identity, SingPass, and DAO governance (27:38) Use cases for DAOs and funding mechanisms (27:51) Sponsor: Daloopa (28:26) Investing in software development and community (30:15) Content creation, research funding, and crowdfunding real estate with crypto (35:01) The network state concept, techno capital fund investors, and ideological bent (38:07) Seed investments and tech solutions for institutional problems (41:06) Corporate vice vs. virtue and profit alignment with values (44:04) Government intervention, regulatory constraints, and construction impact on real estate (49:01) Closing remarks

In this episode of How I Invest, I sit down with Erik Hirsch, Co-CEO of Hamilton Lane, a global leader in private market investing. Erik discusses the evolving landscape of private markets and the integration of digital tools like tokenization in investments. He dives into how private markets are becoming more accessible to retail investors and the future of asset management, with a focus on education and technology. From the role of RIAs and wirehouses to the impact of digital wallets and tokens, Erik provides deep insights into what’s next for investors at every level. If you're curious about the future of investment opportunities and how they will change by 2030, this episode is a must-listen.

Highlights: Private Market Access: How tokenization is revolutionizing private market access for retail investors, making it easier and more efficient to buy into private funds.

The 2030 Vision: The future of investing where both retail and institutional investors can seamlessly manage public and private assets in one place.

Roadblocks and Education: How myths about private markets and a lack of education are slowing adoption, and why proper education is key to unlocking the future of investment.

The Role of RIAs: Why wealth advisors play a critical role in helping clients navigate these changes and how their education will be key to accelerating private market growth.

Adapting to Consumer Expectations: The difference in expectations between institutional and retail investors and how firms need to adjust to meet these demands, especially in terms of technology and accessibility.

Culture at Hamilton Lane: Erik shares how building and maintaining a strong company culture has been a key driver of Hamilton Lane’s success.

The Path to a Trillion Dollars AUM: What Hamilton Lane's growth trajectory looks like, and the future goals as they continue expanding globally.

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Guest Bio: Erik Hirsch is the Co-CEO of Hamilton Lane, a leading private markets investment management firm. With over 30 years of experience, Erik has helped lead Hamilton Lane's growth into one of the largest players in the private market space. Based in Philadelphia, Erik's leadership has focused on innovation, diversification, and bringing private market opportunities to a broader range of investors. His commitment to education and customer-first culture has been instrumental in Hamilton Lane’s success.

Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at dweisburd@gmail.com.

We’d like to thank @JuniperSquare and @ReedSmith for sponsoring this episode!

#VentureCapital #VC #Startups #OpenLP #AssetManagement

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Sponsor: Juniper Square is dedicated to transforming the private markets investing experience. The company provides a full range of modern, connected fund technologies and services for over 2,100 private markets GPs across fundraising, reporting, fund administration, treasury, compliance, and business intelligence. Today, over $1 trillion of assets and 600,000+ LP accounts are managed through Juniper Square software and fund administration services. Learn more at www.junipersquare.com.

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Sponsor: Reed Smith is a dynamic international law firm dedicated to helping clients move their businesses forward. With an inclusive culture and innovative mindset, Reed Smith delivers smarter, more creative legal services that drive better outcomes for their clients. Their deep industry knowledge, long-standing relationships and collaborative structure make them the go-to partner for complex disputes, transactions, and regulatory matters. Learn more at www.reedsmith.com.

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Stay Connected: X / Twitter: David Weisburd: @dweisburd

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Erik Hirsch: https://www.linkedin.com/in/erik-hirsch-hamilton-lane/

Links: Hamilton Lane: https://www.hamiltonlane.com/en-us

Questions or topics you want us to discuss on How I Invest? Email us at dweisburd@gmail.com.

(0:00) Episode preview (1:13) The fallacy of the 60/40 portfolio and institutional strategies (3:54) Diversification strategies in private vs public assets (7:42) Hamilton Lane's focus on the retail market (8:07) Sponsor: Juniper Square (10:32) Hamilton Lane's retail market targeting strategies (13:43) Liquidity concerns for retail investors (15:47) Tokenizing Hamilton Lane funds for accessibility (18:52) Retail and institutional investment convergence vision (20:01) Challenges in retail access to private markets (23:06) Incentivizing RIAs to support private market investments (23:29) Sponsor: Reed Smith (24:48) Erik Hirsch's journey to co-CEO of Hamilton Lane (25:54) Pros and cons of Hamilton Lane's Philadelphia location (27:28) Career insights and underappreciated starting points (28:31) Growth dynamics within Hamilton Lane (29:26) Hamilton Lane's growth and trillion-dollar goal (30:29) Closing remarks

In this episode of How I Invest, I engage with Jackson Craig, Managing Director and Co-Head of H.I.G. Bayside's U.S. Special Situations and Distressed Debt Strategy. With over 20 years of experience in private equity investing, Jackson shares his expertise on navigating distressed debt markets, building resilient portfolios, and uncovering hidden opportunities in complex financial situations. From sourcing distressed assets to managing risk, Jackson offers a masterclass on investing in challenging environments.

Highlights: H.I.G. Capital’s Growth: How the firm expanded from a $75 million fund in 1993 to managing over $67 billion across multiple asset classes, including private equity, real estate, infrastructure, and credit.

Understanding Distressed Debt: The mechanics of distressed debt investing, including yield benchmarks and risk perceptions in distressed securities.

Risk Management in Distressed Investing: How H.I.G. constructs portfolios with a high hit rate and limited downside by focusing on first-lien debt.

Sourcing Distressed Opportunities: The unique ways distressed debt investors find deals—often without companies even being aware of the transactions.

Building Strategic Relationships: Why success in distressed debt relies on long-term relationships with restructuring attorneys, turnaround consultants, and industry insiders.

Portfolio Diversification Beyond Industries: The importance of avoiding over concentration in single risk factors, such as interest rates or energy prices, rather than just industry or geography.

The Role of Optimism in Distressed Investing: Why successful investors need to see beyond the immediate problems to uncover long-term value.

Lessons from 16 Years at H.I.G.: Jackson’s biggest takeaways, including why leadership stability is often a key indicator of a company’s strength.

H.I.G.'s Investment Philosophy: A deep dive into the firm’s focus on small and mid-cap, value-oriented, cash flow-centric investments and its commitment to seeking out complexity.

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Guest Bio: Jackson Craig is the Managing Director and Co-Head of H.I.G. Bayside's U.S. Special Situations and Distressed Debt Strategy, overseeing investments in special situations, restructuring, and turnaround opportunities. With over 20 years of experience in private equity investing, Jackson has been instrumental in the firm’s growth and success in alternative investments. His expertise spans private equity, credit markets, and distressed investing, making him a leading voice in the industry.

Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at dweisburd@gmail.com.

We’d like to thank @JuniperSquare and @ReedSmith for sponsoring this episode!

#VentureCapital #VC #Startups #OpenLP #AssetManagement

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Sponsor: Juniper Square is dedicated to transforming the private markets investing experience. The company provides a full range of modern, connected fund technologies and services for over 2,100 private markets GPs across fundraising, reporting, fund administration, treasury, compliance, and business intelligence. Today, over $1 trillion of assets and 600,000+ LP accounts are managed through Juniper Square software and fund administration services. Learn more at www.junipersquare.com.

Sponsor: Reed Smith is a dynamic international law firm dedicated to helping clients move their businesses forward. With an inclusive culture and innovative mindset, Reed Smith delivers smarter, more creative legal services that drive better outcomes for their clients. Their deep industry knowledge, long-standing relationships and collaborative structure make them the go-to partner for complex disputes, transactions, and regulatory matters. Learn more at www.reedsmith.com.

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Stay Connected: Twitter: David Weisburd: @dweisburd

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Jackson Craig: https://www.linkedin.com/in/jackson-craig-458b645b/

Links H.I.G. Capital: www.higcapital.com

Questions or topics you want us to discuss on How I Invest? Email us at dweisburd@gmail.com.

(0:00) Episode preview (1:25) Understanding distressed debt investment (4:53) Identifying and assessing distressed debt opportunities (7:24) Investment process and due diligence (9:02) Sponsor: Juniper Square (9:36) Relationship management and distressed sales (10:39) Tax considerations and investor base (11:33) Investment discipline in distressed debt (12:36) Success factors in distressed debt investing (14:43) Portfolio diversification and risk management (19:03) Sponsor: Reed Smith (19:38) Evaluating business quality and management in distress (21:02) Navigating the bankruptcy process (22:02) Long-term strategy in distressed investing (23:19) Overcoming sourcing challenges (23:48) HIG's distinct investment approach and LP feedback (25:21) Competitive advantage in distressed markets (25:45) Closing remarks

In this episode of How I Invest, I speak with Jeremy Heer, Managing Director at the University of Illinois Foundation, about the art of networking, the power of super connectors, and the evolving landscape of institutional investing. Jeremy shares his insights on building relationships that drive investment success, the importance of strategic networking, and how attending conferences with intent can create game-changing opportunities. He also dives into the future of nuclear energy, the role of generalist investors in discovering new asset classes, and the long-term value of investment engagement.

Highlights: The Role of a Super Connector: Jeremy explains what defines a “super connector” and why having them in your network is essential for success in investing.

Strategic Networking: How building and maintaining relationships across industries can unlock top-tier investment opportunities.

Conference Best Practices: Why proper preparation and a mix of structured and stochastic networking can maximize the value of attending events.

The Future of Nuclear Energy: Jeremy’s investment thesis on nuclear as a high-potential energy source and the challenges in capital deployment.

Generalist vs. Specialist Investing: How being a generalist can give investors a first-mover advantage in emerging asset classes.

Lessons from the University of Chicago: Jeremy shares insights from his time at one of the top endowments in the world.

The Long-Term Value of Relationship-Based Investing: Why some of the best investment opportunities emerge from patient, long-term engagement rather than immediate transactions.

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Guest Bio: Jeremy Heer is the Managing Director of the University of Illinois Foundation, where he leads investment research and engagement. Before joining Illinois, he spent over a decade at the University of Chicago’s endowment, one of the top-performing institutional funds in the world. With deep expertise in building strategic relationships, Jeremy is a master of leveraging networks for investment success. He is passionate about connecting with top-tier investors, founders, and thought leaders to uncover unique opportunities in the market.

Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at dweisburd@gmail.com.

We’d like to thank @JuniperSquare for sponsoring this episode!

#VentureCapital #VC #Startups #OpenLP #AssetManagement

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Sponsor: Juniper Square is dedicated to transforming the private markets investing experience. The company provides a full range of modern, connected fund technologies and services for over 2,100 private markets GPs across fundraising, reporting, fund administration, treasury, compliance, and business intelligence. Today, over $1 trillion of assets and 600,000+ LP accounts are managed through Juniper Square software and fund administration services. Learn more at www.junipersquare.com.

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Stay Connected: X / Twitter: David Weisburd: @dweisburd

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Jeremy Heer: https://www.linkedin.com/in/jeremy-j-heer-cfa-caia/

Links: University of Illinois Foundation: https://uif.uillinois.edu/

Questions or topics you want us to discuss on How I Invest? Email us at dweisburd@gmail.com.

(0:00) Episode preview (3:56) Non-financial drives of super connectors (4:11) Sponsor: Juniper Square (5:55) How to be memorable & Networking at conferences (12:33) The investment potential of nuclear energy & University experiences (17:00) The unique role at University of Illinois Foundation & Generalist investors in VC (19:03) Closing remarks

In this episode of How I Invest, I dive deep into a discussion with John Skjervem, Chief Investment Officer at Utah Retirement Systems (URS), to uncover the unique governance and investment strategies behind one of the most innovative public pension funds in the United States. John shares his insights on governance structures, private equity allocations, the benefits of a "fishbowl-free" decision-making process, and his approach to alternative energy investments. Whether you're curious about pension fund management or the future of disruptive energy investments like nuclear fusion, this episode is a masterclass in strategic thinking and long-term investing.

Highlights: Governance Matters: Why URS’s closed-door investment meetings create better outcomes compared to traditional public pension governance.

Transparency vs. Returns: How excessive transparency can lead to political grandstanding and ultimately harm long-term investment performance.

Asset Allocation Strategy: A deep dive into URS’s allocation, including a 14% allocation to private equity with significant exposure to venture capital.

Direct Real Estate Investments: How URS has built a successful real estate portfolio, reducing fees and maintaining long-term control over assets.

Energy and Infrastructure Investments: The role of direct investments in oil, gas, and alternative energy as an inflation hedge.

The Case for Venture Capital: Why URS prioritizes venture capital investments over private credit to maximize returns.

Betting on Nuclear Fusion: The potential for a 100x return on URS’s investments in fusion energy and the long-term implications for the energy sector.

Size vs. Agility: Why smaller funds like URS have an advantage in private markets despite their scale limitations.

Lessons from the Global Financial Crisis: How John’s approach to risk management and asset allocation was shaped by 2008.

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Guest Bio: John Skjervem serves as the Chief Investment Officer at Utah Retirement Systems, where he oversees over $50 billion in assets. With prior experience managing larger funds like the Oregon Public Employees Retirement Fund and Northern Trust's wealth business, John brings a wealth of expertise to his current role. Known for his innovative governance approach and deep knowledge of alternative investments, John is passionate about achieving long-term success for URS beneficiaries.

Our Podcast now receives more than 300,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at dweisburd@gmail.com.

We’d like to thank @JuniperSquare @ReedSmith for sponsoring this episode!

#VentureCapital #VC #Startups #OpenLP #AssetManagement

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SPONSOR: Juniper Square is dedicated to transforming the private markets investing experience. The company provides a full range of modern, connected fund technologies and services for over 2,100 private markets GPs across fundraising, reporting, fund administration, treasury, compliance, and business intelligence. Today, over $1 trillion of assets and 600,000+ LP accounts are managed through Juniper Square software and fund administration services. Learn more at www.junipersquare.com.

SPONSOR: Reed Smith is a dynamic international law firm dedicated to helping clients move their businesses forward. With an inclusive culture and innovative mindset, Reed Smith delivers smarter, more creative legal services that drive better outcomes for their clients. Their deep industry knowledge, long-standing relationships and collaborative structure make them the go-to partner for complex disputes, transactions, and regulatory matters. Learn more at www.reedsmith.com.

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Stay Connected: Twitter: David Weisburd: https://x.com/DWeisburd

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ John Skjervem: https://www.linkedin.com/in/john-d-skjervem-cfa-4698794/

Links

Utah Retirement Systems: https://www.urs.org/

Questions or topics you want us to discuss on How I Invest? Email us at dweisburd@gmail.com.

(0:00) Episode preview (1:00) Asset allocation and governance at Utah Retirement Systems (4:07) Governance structure at Utah Retirement Systems (9:25) Long-term investment challenges (10:57) Sponsor: Juniper Square (11:30) Private equity and real estate in asset allocation (15:44) Managing a $50 billion fund (16:25) Sponsor: Reed Smith (17:30) Investment check sizes and advisory roles (20:31) Comparing Utah Retirement Systems with Alaska Permanent Fund (22:11) Lessons from the 2008 financial crisis (23:57) Exploring high-risk investments: Fusion portfolio (26:10) Closing remarks

In this episode of How I Invest, I interview Constantine Karides, a Lead Partner at Reed Smith, to discuss the critical role lawyers play in the startup and venture capital ecosystem. Constantine shares insights on what founders and investors should look for in legal counsel, the leverage model law firms use, and how AI is reshaping the legal landscape. From the importance of choosing the right law firm to navigating legal costs effectively, this episode is packed with actionable advice for entrepreneurs, venture capitalists, and investors.

Highlights: Choosing a Lawyer as a Strategic Partner: Beyond paperwork, founders should seek legal advisors who bring investor connections, industry expertise, and pricing flexibility.

The Importance of Internal Influence: How a lawyer’s standing within a firm impacts their ability to secure favorable terms and resources for clients.

VCs & Legal Counsel: What venture capital funds should prioritize when selecting legal partners and how these relationships can create long-term value.

Law Firm Profit Models: Understanding the leverage model law firms use to maximize profits and how clients can navigate these dynamics.

AI & The Future of Law: How artificial intelligence is transforming the legal industry, from document review to litigation strategy.

Building Long-Term Client Relationships: Constantine’s philosophy on blending business with personal relationships to drive success.

Lessons from Experience: Mistakes Constantine made early in his career and how they shaped his approach to law and business.

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Guest Bio: Constantine Karides is a Lead Partner at Reed Smith, a global law firm known for its expertise in venture capital, private equity, and corporate transactions. With over 30 years of experience, Constantine has built a reputation as a trusted advisor to startups, funds, and investors, offering not just legal counsel but also strategic business insights. Recognized as a "rainmaker" at Reed Smith, he emphasizes client relationships, networking, and long-term value creation.

Our Podcast now receives more than 200,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at dweisburd@gmail.com.

We’d like to thank @ReedSmith for sponsoring this episode!

#VentureCapital #VC #Startups #OpenLP #AssetManagement

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SPONSOR: Reed Smith is a dynamic international law firm dedicated to helping clients move their businesses forward. With an inclusive culture and innovative mindset, Reed Smith delivers smarter, more creative legal services that drive better outcomes for their clients. Their deep industry knowledge, long-standing relationships and collaborative structure make them the go-to partner for complex disputes, transactions, and regulatory matters. Learn more at www.reedsmith.com.

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Stay Connected: Twitter: David Weisburd: @dweisburd

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/
Constantine Karides: https://www.linkedin.com/in/constantine-karides/

Links Reed Smith: www.reedsmith.com

Questions or topics you want us to discuss on How I Invest? Email us at dweisburd@gmail.com.

(0:00) Episode preview (2:08) Law firms' internal credibility and Venture Capital specific needs (5:29) Evaluating Startups and the leverage model in law firms (9:57) Trust-building and client relationship philosophy (14:41) Early career lessons and the impact of AI on the legal field (19:00) Client views on AI adoption in law firms (21:03) Closing remarks

In this episode of How I Invest, I have a conversation with Mel Williams, Co-Founder and General Partner at TrueBridge Capital Partners. We dive into TrueBridge’s pivotal role as Forbes' data partner for the prestigious Midas List, its strategic approach to venture capital fund-of-funds investing, and how the firm consistently identifies and backs the top-performing fund managers. Mel provides a masterclass on portfolio construction, risk management, and scaling a successful venture investment platform. Whether you’re an institutional investor, a fund manager, or simply intrigued by the inner workings of venture capital, this episode is packed with essential takeaways.

Highlights: The Midas List Partnership: How TrueBridge collaborates with Forbes to curate the definitive VC ranking and what it means for the industry.

Fund of Funds Strategy: The five key investment strategies that shape TrueBridge’s unique venture approach—core venture, seed, direct, secondary, and blockchain investments.

The Power of Forced Ranking: A disciplined framework for ranking fund managers and how it enhances returns.

Gaining a Competitive Edge: How TrueBridge’s relationships with elite GPs provide them unparalleled access and insight.

Navigating Blockchain Volatility: TrueBridge’s philosophy on investing in blockchain and adjusting for its extreme market cycles.

Scaling Venture Funds Effectively: Best practices for fund managers to grow while maintaining their competitive advantage.

International vs. Domestic Venture Investing: How TrueBridge evaluates and ranks global venture funds against U.S.-based managers.

Lessons from Building TrueBridge: The realities of raising early funds and scaling a top-tier fund-of-funds platform.

Debunking the Fund-of-Funds Fee Myth: How TrueBridge offsets the double-fee structure through strategic overcommitment and capital recycling.

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Guest Bio: Mel Williams is the Co-Founder and General Partner at TrueBridge Capital Partners, a premier venture capital fund-of-funds specializing in backing top-tier venture firms and startups. With a background in institutional investing at the University of North Carolina Endowment and the Rockefeller Foundation, Mel brings unparalleled expertise in fund selection, portfolio construction, and venture capital strategy. Under his leadership, TrueBridge has cultivated one of the most coveted LP portfolios in the industry, leveraging deep networks and a research-driven investment approach.

Our Podcast now receives more than 200,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at dweisburd@gmail.com.

#VentureCapital #VC #Startups #OpenLP #AssetManagement

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Stay Connected: Twitter: David Weisburd: @dweisburd

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Mel Williams: https://www.linkedin.com/in/mel-williams-00584a5/

Links TrueBridge Capital Partners: https://www.truebridgecapital.com/

Questions or topics you want us to discuss on How I Invest? Email us at dweisburd@gmail.com.

(0:00) Episode preview (4:38) Investing in blockchain and managing volatility in venture funds (5:51) Building relationships and the forced ranking system in portfolio management (10:21) Criteria for adding or removing venture fund managers (14:43) Best practices for scaling and international venture investments (20:23) Challenges in raising funds and the venture industry evolution (2012-2021) (24:17) Comparing fund of funds to direct venture capital investments (26:51) Efficiency and key aspects of TruBridge's fund of funds model (29:05) Closing remarks

In this episode of How I Invest, I dive deep into a conversation with Henry Ward, CEO of Carta, to discuss his journey building one of the most transformative companies in private market infrastructure. From cap table management to fund administration and beyond, Henry shares his insights on entrepreneurship, innovation, and the future of private equity. We delve into Carta's strategic pivots, its playbook for turning services into scalable software, and Henry's contrarian views on AI and leadership. This episode is packed with lessons for founders, investors, and operators navigating the evolving landscape of private capital.

Highlights: The Carta Journey: How Carta evolved from solving cap table management to building software for fund CFOs.

Scaling Through Innovation: The importance of constantly iterating and innovating in markets with limited growth potential.

AI in Private Markets: Why Henry is focused on using AI to enhance customer experiences instead of reducing headcount. Building the Carta Cartel: How former Carta employees are founding companies with Henry's support—and reshaping angel investing.

Services to Software: Carta's unique playbook for acquiring service businesses and turning them into software-driven solutions.

Future of Fund Admin: The roadmap for automating fund administration and achieving “one-click” reporting by 2030.

Private Equity Expansion: Carta’s strategy for becoming the operating system for private capital beyond venture.

Leadership Insights: Henry’s take on founder mode, micromanagement, and why caring deeply is essential to great leadership.

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Guest Bio: Henry Ward is the CEO of Carta, a company revolutionizing private market infrastructure through software. Since its founding in 2012, Carta has grown into the industry standard for cap table management, fund administration, and private market data. Henry is also an active angel investor, backing numerous startups founded by former Carta employees. Known for his visionary thinking and contrarian ideas, Henry is committed to reshaping how private capital markets operate.

Our Podcast now receives more than 200,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at dweisburd@gmail.com.

#VentureCapital #VC #Startups #OpenLP #AssetManagement

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Stay Connected: X / Twitter: David Weisburd: @dweisburd Henry Ward: @henrysward

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Henry Ward: https://www.linkedin.com/in/heward/

Links: Carta: https://www.carta.com/

Questions or topics you want us to discuss on How I Invest? Email us at dweisburd@gmail.com.

(0:00) Episode preview (2:31) Building Carta: Innovation and Execution (5:03) AI's Role and Impact at Carta (9:21) Fund Administration Challenges and Solutions (12:33) Investing in Carta's Team and Culture (14:51) Angel Investing and CEO Controversies (17:48) Balancing Founder and Investor Roles (22:03) Carta's Acquisition Strategy and Automation Goals (25:10) Carta's Role for CFOs in Private Equity and VC (27:32) Carta's Strategic Pivot and Growth Plans (30:39) Brand Transition: Venture to Private Equity (34:35) Closing remarks

In this episode of How I Invest, I connect with Lorenzo Thione, Managing Director at Gaingels, one of the most active and inclusive venture syndicates in the world. Lorenzo discusses his philosophy on diversity, equity, and inclusion (DEI), the democratization of venture capital, and his thoughts on the AI revolution. From his experience building a portfolio of over 100 investments to lessons learned from co-founding PowerSet, Lorenzo provides invaluable insights for investors and entrepreneurs alike.

Highlights: Philosophy on DEI: How the distribution of talent and opportunity shapes Gaingels' mission to bring inclusivity to venture capital.

Gaingels’ Approach: Investing in companies that prioritize diversity in talent, governance, and capital while enabling LPs to invest with as little as $1,000.

Venture Allocation: Advice for high-net-worth investors on diversifying their portfolios across stages, sectors, and liquidity horizons.

Lessons from Uber: Why Lorenzo passed on the Uber seed round and how it shaped his investment philosophy.

AI Investing: Insights into the evolution of AI, the importance of category-defining opportunities, and the impact of recent major investments in AI infrastructure.

Angel Investing: The importance of backing founders you know and trust, and how personal relationships can lead to better investment outcomes.

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Guest Bio: Lorenzo Thione is a serial entrepreneur, investor, and expert in Artificial Intelligence. Currently, as Managing Director of Gaingels, he leads investments in AI, deep-tech, and consumer tech, promoting diversity in venture capital. He co-founded Powerset, an AI-driven search engine acquired by Microsoft and integrated into Bing. Beyond technology, Lorenzo is a celebrated Broadway producer, with productions like "Hadestown" and "The Inheritance," earning multiple Tony Awards. He also co-founded StartOut, supporting LGBTQ+ entrepreneurs. Born in Milan, he holds an M.S. in Computer Engineering from the University of Texas at Austin.

Our Podcast now receives more than 200,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at dweisburd@gmail.com.

#VentureCapital #VC #Startups #OpenLP #AssetManagement

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Stay Connected: X / Twitter: David Weisburd: @dweisburd

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Lorenzo Thione: https://www.linkedin.com/in/lorenzothione/

Links: Gaingels: https://www.gaingels.com/

Questions or topics you want us to discuss on How I Invest? Email us at dweisburd@gmail.com.

(0:00) Episode preview (2:52) Gaingels syndicate and low minimum LP investment strategy (5:15) Venture capital allocation advice for high net worth individuals (6:19) Diversification strategies within venture capital (8:37) Analyzing long-term venture capital returns (9:52) Gaingels investing access and strategic insights (13:03) Key lessons from early-stage angel investing experiences (16:56) Investing in AI and portfolio strategy considerations (19:37) SoftBank and Sam Altman's AI investment impact (23:29) Closing remarks

In this episode of How I Invest, I dive into a conversation with Nichole Wischoff, Founder and Managing Partner at Wischoff Ventures, to explore her remarkable journey of raising a $50 million fund during one of the toughest markets of 2024. Nichole shares her insights on fundraising strategies, the power of media in deal sourcing, and building a personal brand. She also discusses her unique approach to fostering relationships in venture capital and why community and authenticity are key drivers of success in this space. This episode is packed with actionable takeaways for emerging fund managers and anyone navigating the world of VC.

Highlights: $50 Million Fundraise: How Nichole secured her fund’s anchor and achieved a first close in just two months.

Building Distribution Advantage: Leveraging social media and brand-building to access top founders and close deals.

Fund Size Challenges: Overcoming objections from institutional LPs and proving scalability.

Strategic Fundraising: Nichole's timeline, drip campaigns, and tactics to convert LPs at a 26% rate.

Community-Driven Success: The value of collaboration among emerging managers and fostering trusted relationships.

The Twitter Advantage: Nichole’s journey to building a massive online following and using it as a competitive edge.

Cringe Scales: Why embracing discomfort on social media pays dividends for fund managers.

Future Focus: Nichole’s advice for navigating relationships, building a firm, and standing out in the VC world.

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Guest Bio: Nichole Wischoff is the Founder and Managing Partner of Wischoff Ventures, a venture capital firm investing in early-stage startups. With deep operational experience at multiple high-growth companies and a proven track record in venture capital, Nichole has built her reputation as a leader in the emerging manager space. Known for her authenticity and strategic approach, she is passionate about building her firm and brand in public while supporting the next wave of groundbreaking founders.

Our podcast now receives more than 200,000 downloads a month. Interested in sponsoring an episode? Please email me at dweisburd@gmail.com.

We’d like to thank @ReedSmith for sponsoring this episode!

#VentureCapital #VC #Startups #OpenLP

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SPONSOR: Reed Smith is a dynamic international law firm dedicated to helping clients move their businesses forward. With an inclusive culture and innovative mindset, Reed Smith delivers smarter, more creative legal services that drive better outcomes for their clients. Their deep industry knowledge, long-standing relationships and collaborative structure make them the go-to partner for complex disputes, transactions, and regulatory matters. Learn more at www.reedsmith.com.

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Stay Connected: X / Twitter: David Weisburd: @dweisburd Nichole Wischoff: @NWischoff

LinkedIn: David Weisburd: David Weisburd LinkedIn Nichole Wischoff: Nichole Wischoff LinkedIn

Links: Wischoff Ventures: www.wischoff.com

Questions or topics you want us to discuss on How I Invest? Email us at dweisburd@gmail.com.

(0:00) Episode preview (2:08) Leveraging social media and brand for distribution advantage (4:31) Overcoming LP objections and scaling investments (6:49) Strategies for first close and securing anchor LPs (10:29) Identifying and engaging interested LPs (13:34) Insights into decision-making of top quartile LPs and endowments (15:52) Collaborating with emerging managers and building trust (19:43) Importance of the 80/20 rule in relationships (21:27) Strategies for building a Twitter presence and follower psychology (25:47) Tips for effective Twitter engagement and brand growth (28:28) Closing remarks

In this episode of How I Invest, I sit down with Nick Shekerdemian, entrepreneur, investor, and founding partner of The Venture Collective (TVC). A former Oxford student turned Thiel Fellow, Nick shares his journey of dropping out of university to pursue big ideas and how the fellowship helped shape his path in venture capital. We explore TVC's unique approach to portfolio construction, investing in deep tech and computational biology, and why thesis-driven investing is the future of venture capital. Nick also discusses challenges like founder breakups, scaling value-added strategies, and his thoughts on the next big shifts in technology and bio-defense.

Highlights: Thiel Fellowship: Why Nick left Oxford to join the fellowship and how it transformed his career.

Portfolio Construction: TVC’s concentrated approach to seed-stage investing and leveraging informational advantages to support founders.

Thesis-Driven Investing: Why Nick believes the future of venture capital lies in backing big, transformative ideas, especially in deep tech, computational biology, and AI.

Bio-Defense and Innovation: How advancements in AI and biology could revolutionize healthcare and address emerging bio-defense challenges.

Supporting Founders: The importance of transparency, setting micro-goals, and building trust for navigating challenges like founder breakups.

Opportunities in Deep Tech: Exploring transformative sectors like defense tech, healthcare personalization, and reindustrialization driven by sustainability and AI.

Shifts in Venture Capital: Nick’s prediction that rapid innovation will redefine the venture landscape in the next few years.

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Guest Bio: Nick Shekerdemian is the founding partner of The Venture Collective (TVC), a seed-stage investment firm focused on backing visionary founders tackling transformative problems. A former Thiel Fellow, Nick has built his career at the intersection of entrepreneurship and venture capital, with a deep passion for investing in ambitious ideas in deep tech, healthcare, and sustainability. He’s committed to supporting founders who think differently and aren’t afraid to challenge the status quo.

Our Podcast now receives more than 200,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at dweisburd@gmail.com.

#VentureCapital #VC #Startups #OpenLP #AssetManagement

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Stay Connected: Twitter: David Weisburd: @dweisburd

LinkedIn: David Weisburd: linkedin.com/in/dweisburd/ Nick Shekerdemian: https://www.linkedin.com/in/nshekerdemian/

Links The Venture Collective: https://theventurecollective.com

Questions or topics you want us to discuss on How I Invest? Email us at dweisburd@gmail.com.

(0:00) Episode preview (1:10) Dropping out of Oxford and Thiel Fellowship Insights (4:01) Seed Stage Startup Portfolio Construction (5:58) Leveraging Informational Advantages (8:33) Scaling Value-Added Strategies for Startups (10:28) Reporting Cadence vs. Company Performance (11:42) Fostering Transparency with Founders (14:17) TVC's Alpha Sources and Thematic Investing (18:28) Deep Tech Investments and Defense Tech Excitement (20:02) Changing LP Sentiments and Non-Momentum Investing (22:40) Computational Biology as an Investment Opportunity (24:50) Contrarian Views on Venture Capital (26:15) The Future of Biodefense and Bioweapons (27:46) Call to Action for Problem Solvers (28:34) Closing remarks

In this episode of How I Invest, I sit down with Marcie Frost, CEO of CalPERS, the largest public pension fund in the United States. From her beginnings in public service to leading a $502.9 billion portfolio, Marcie shares her journey and offers insights into managing one of the most influential pension funds globally. We discuss the challenges of governance, integrating climate change risks into investment decisions, and the importance of building a culture of trust and innovation. Marcie also delves into CalPERS’ strategic focus on sustainable investments, diversity, equity, and inclusion initiatives, and how the organization is setting benchmarks in transparency and fiduciary responsibility.

Highlights: Public Service Journey: Marcie’s transition from Washington state's Department of Retirement Systems to leading the largest public pension fund in the U.S.

CalPERS’ Mission: The role of a $502.9 billion portfolio in securing the financial future of over 2 million California public sector workers and their families.

Strategic Asset Allocation: How CalPERS utilizes its Asset Liability Management process to inform asset allocation decisions and set investment return assumptions.

Integrating Climate Risks: The incorporation of climate change risks into investment decisions across all asset classes and the launch of a $100 billion sustainable investment strategy aimed at reducing carbon emissions intensity by 50% by 2030.

Building a Culture of Trust: Marcie’s approach to fostering an inclusive culture through the development of CalPERS' first Diversity, Equity & Inclusion framework.

Sustainable Investments: CalPERS' commitment to sustainable investing, including its role as a founding member of Climate Action 100+, an initiative with 700 signatories and $68 trillion in assets under management.

Stakeholder Engagement: Expansion of stakeholder outreach to ensure all parties are informed and have a voice in the system's future.

Advocacy for Defined Benefits: Marcie's belief in providing equitable and affordable health care and retirement options for public employees.

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Guest Bio: Marcie Frost is the Chief Executive Officer of CalPERS, overseeing the largest public pension fund in the United States. With over 30 years of experience in public service, Marcie is a dedicated advocate for financial security, transparency, and sustainability. Under her leadership, CalPERS has advanced its goals in asset management, stakeholder engagement, and cultural transformation, ensuring that its over 2 million members can retire with dignity.

Our Podcast now receives more than 200,000 downloads a month. Are you interested in sponsoring an episode? Please email me at dweisburd@gmail.com.

We’d like to thank @ReedSmith for sponsoring this episode!

#VentureCapital #VC #Startups #OpenLP #AssetManagement

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Sponsor: Reed Smith is a dynamic international law firm dedicated to helping clients move their businesses forward. With an inclusive culture and innovative mindset, Reed Smith delivers smarter, more creative legal services that drive better outcomes for their clients. Their deep industry knowledge, long-standing relationships and collaborative structure make them the go-to partner for complex disputes, transactions, and regulatory matters. Learn more at www.reedsmith.com.

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Stay Connected: X / Twitter: David Weisburd: @dweisburd

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Marcie Frost: https://www.linkedin.com/in/marcie-frost-56a30a281/

Links:

CalPERS: https://www.calpers.ca.gov/

Questions or topics you want us to discuss on How I Invest? Email us at dweisburd@gmail.com.

(0:00) Episode preview (0:35) CalPERS' strategic asset allocation, risk limits, and board dynamics (2:39) Composition, election, and decision-making of CalPERS' investment committee (5:25) Understanding board members' risk appetite and stakeholder engagement (9:07) Navigating political aspects and role differentiation at CalPERS (14:02) Changing organizational culture and focusing on investment results (18:29) Sponsor: Reed Smith (21:22) Managing media scrutiny and its impact on investment decisions (22:36) Stability and importance of the CIO role at CalPERS (23:13) Emerging managers, diversity, and strategic planning for 2025-2029 (24:55) Evaluating private markets, liquidity premium, and active vs passive management (27:47) Building relationships as a first call partner to managers (29:43) CEO reflections and fostering a world class culture at CalPERS (31:27) Key takeaways about CalPERS for listeners (34:38) Closing remarks

In this episode of How I Invest, I connect with Ken Smythe, founder of Next Round Capital, to discuss his journey in private markets, lessons from hedge fund management, and the future of thematic investing. Ken shares insightful stories about spotting talent, using key executive moves as signals for investment opportunities, and the rise of AI and defense technology. We also explore the challenges facing venture capital and private equity in today’s market, including liquidity bottlenecks and the hunt for alpha in a rapidly evolving landscape. Ken's personal story of resilience and his passion for innovation shine through in this inspiring conversation.

Highlights: Key Signals in Early-Stage Investing: Why tracking executive moves from established companies like Apple or Stripe to startups can offer a major edge in spotting emerging opportunities.

AI's Evolution: The current state of AI innovation compared to the early days of the internet and the need for sustainable business models to monetize AI advancements.

Defense Tech: How startups are disrupting traditional players like Lockheed Martin and General Dynamics with cutting-edge technologies tailored to modern battlefields.

Hedge Fund Insights: The importance of diversification, risk management, and identifying specialized talent in building successful multi-strategy hedge funds.

Secondary Markets: The growing role of VCs, family offices, and retail investors in accessing shares of companies like SpaceX and how liquidity challenges are reshaping private equity strategies.

Thematic Investing: From AI chatbot agents to defense technology, Ken outlines the trends and themes that he believes will dominate in 2025 and beyond.

Personal Resilience: Ken’s inspiring journey of launching his own firm amid personal challenges, underscoring the importance of seizing opportunities and living with purpose.

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Guest Bio: Ken is the founder of Next Round Capital, a firm specializing in secondary investments, co-investments, and niche opportunities in technology and AI. With a background in hedge fund management and a focus on thematic investing, Ken leverages his deep network and expertise to identify groundbreaking opportunities in private markets. He is passionate about innovation and building meaningful relationships in the venture ecosystem.

Our Podcast now receives more than 200,000 downloads a month. Are you interested in sponsoring an episode? Please email me at dweisburd@gmail.com.

#VentureCapital #VC #Startups #OpenLP

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Stay Connected: X / Twitter: David Weisburd: @dweisburd

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Ken Smythe: https://www.linkedin.com/in/ken-smythe/

Links: Next Round Capital: https://www.nextroundcapital.com

Questions or topics you want us to discuss on How I Invest? Email us at dweisburd@gmail.com

(0:00) Episode preview (1:37) Key Executive Movements in Tech (3:38) Adverse Selection in Venture Capital (4:35) Investment Trends for 2025 (6:27) Focus on Defense Technology Investments (8:06) Managing Liquidity in Venture Portfolios (10:36) Analyzing SpaceX's Investment Potential (11:45) Hedge Fund Insights from a $5 Billion Experience (14:37) Strategies for Recruiting and Evaluating Portfolio Managers (24:50) The Art of Referencing and Backchanneling (26:01) Spotlight on Next Round Capital (27:39) AI Investment Landscape Analysis (28:34) Business Model Significance in Tech Sector (29:52) Closing remarks

In this episode of How I Invest, I sit down with Lawrence Calcano, Chairman and CEO of iCapital, to explore the transformative potential of alternative investments in the wealth management space. Lawrence shares his journey from Goldman Sachs to building iCapital, a platform managing over $200 billion in alternative assets. We dive deep into the challenges and opportunities in democratizing access to private markets, the role of technology in scaling the alternatives industry, and the growing appetite for private equity and credit among high-net-worth investors. If you're curious about the future of wealth management and the intersection of technology and alternatives, this episode is a must-listen.

Highlights: The Wealth Market's Untapped Potential: Retail investors collectively control $145 trillion globally, rivaling institutional markets.

Democratizing Alternatives: iCapital enables financial advisors to access institutional-quality alternative products and simplifies operational complexities with technology.

Trends in High-Net-Worth Investing: A shift back to equities in 2025 following a credit-dominated two years.

Illiquidity as a Feature, Not a Bug: How private markets generate alpha through active management during illiquidity periods.

Overcoming the Chicken-and-Egg Problem: Building trust with both advisors and general partners to grow the platform.

Technology as a Game Changer: AI, distributed ledgers, and automation reduce inefficiencies and errors in managing private fund investments.

Future of Alternatives: Allocations to alternatives are expected to grow significantly as education and access improve.

Key Lessons in Investing: Lawrence emphasizes the importance of understanding investments fully to navigate market dynamics effectively.

Building a Cohesive Culture: Insights on leadership, teamwork, and fostering a shared mission at iCapital.

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Guest Bio: Lawrence Calcano is the Chairman and CEO of iCapital, a leading platform providing access to alternative investments for wealth advisors and their clients. With a background in tech investment banking at Goldman Sachs, Lawrence has been instrumental in modernizing how advisors and high-net-worth individuals access and manage private market investments.

Our podcast now receives more than 200,000 downloads a month. Are you interested in sponsoring an episode? Please email me at dweisburd@gmail.com.

We’d like to thank @ReedSmith for sponsoring this episode!

#VentureCapital #VC #Startups #OpenLP #AssetManagement

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SPONSOR: Reed Smith is a dynamic international law firm dedicated to helping clients move their businesses forward. With an inclusive culture and innovative mindset, Reed Smith delivers smarter, more creative legal services that drive better outcomes for their clients. Their deep industry knowledge, long-standing relationships, and collaborative structure make them the go-to partner for complex disputes, transactions, and regulatory matters. Learn more at www.reedsmith.com.

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Stay Connected: X / Twitter: David Weisburd: @dweisburd

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Lawrence Calcano: https://www.linkedin.com/in/lawrence-calcano-5b8b9111/

Links: iCapital: https://icapitalnetwork.com/

Questions or topics you want us to discuss on How I Invest? Email us at dweisburd@gmail.com.

(0:00) Episode preview (1:14) I Capital's founding and evolution from Goldman Sachs (2:37) Private equity's wealth channel strategy and challenges (4:56) Comparing high net worth and institutional investors (7:31) Investor trends: From credit to equity interests (10:27) Projections for the future of the alternatives industry (14:45) Wealth channels' impact on adverse selection (15:23) Sponsor: Reed Smith (19:28) I Capital's aggregation service for General Partners (GPs) (20:32) The enduring nature of the wealth channel (22:16) The role of emerging managers in the wealth channel (26:00) Lawrence Calcano's investment philosophy and early lessons (27:40) The significance of investment comprehension (28:03) Fostering and maintaining iCapital's company culture (30:39) Scaling company values with organizational growth (32:31) iCapital's ambitious vision for 2030 (33:22) Addressing challenges in the alternatives sector (34:43) Leveraging technology to solve client problems (37:11) Implications of the accredited investor rule (38:46) Closing remarks

In this episode of How I Invest, I sit down with Felix Ejeckam, Co-Founder and CEO of Akash Systems. Felix discusses how Akash is leveraging synthetic diamond technology to revolutionize cooling for high-power microchips used in AI servers and satellite communications. He shares insights on their $68 million CHIPS Act funding, the importance of U.S. semiconductor manufacturing, and Akash’s journey through tough times to becoming a leader in cutting-edge technology. A must-listen for anyone interested in semiconductors, AI, or transformative tech innovations.

Highlights: What is Akash Systems? A company pioneering synthetic diamond cooling technology to enhance performance and efficiency in AI servers and satellite communications systems.

Synthetic Diamond Technology: How Akash grows lab-made diamonds and integrates them into chips to reduce cooling costs and improve performance by up to 90%.

Massive Market Opportunity: Targeting a $200-$400 billion market spanning data centers, satellite communications, EVs, smartphones, and defense systems.

CHIPS Act Funding: Akash recently secured $68 million in CHIPS funding to scale manufacturing, establish a semiconductor fab in Oakland, and support U.S. economic and national security goals.

Overcoming Tough Times: Reflecting on the challenges during COVID-19, Akash used the “quiet years” to refine its technology, expand into new markets like AI, and emerge stronger.

Staying Non-Consensus: The importance of conviction, foresight into market trends, and building a team that balances optimism and pragmatism.

What’s Next for Akash: Upcoming satellite launches, server shipments in Q1, and a trajectory to becoming the leading high-end AI server company globally.

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Guest Bio: Felix Ejeckam is the Co-Founder and CEO of Akash Systems, a trailblazing company using synthetic diamond technology to transform semiconductor cooling and performance. Under Felix’s leadership, Akash has achieved groundbreaking innovations in AI servers and satellite communications systems, contributing to U.S. manufacturing and technological independence. Felix is passionate about fostering innovation and building resilient companies that thrive in challenging times.

Our Podcast now receives more than 200,000 downloads a month. Are you interested in sponsoring an episode? Please email me at dweisburd@gmail.com.

#VentureCapital #VC #Startups #OpenLP #AssetManagement

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Stay Connected: X / Twitter: David Weisburd: @dweisburd Felix Ejeckam: @felixejeckam

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Felix Ejeckam: https://www.linkedin.com/in/felixejeckam/

Links: Akash Systems: https://www.akashsystems.com/

Questions or topics you want us to discuss on How I Invest? Email us at dweisburd@gmail.com.

(0:00) Episode preview (2:08) Akash Systems and the cost of cooling server chips (4:05) Chips Act funding (7:13) Competitive landscape in AI server market (11:33) US election impact on Akash Systems (12:39) Overcoming COVID-19 challenges (14:32) Building resilience and strategic pivots (19:30) Non-consensus investing strategies (22:38) Closing remarks

In this episode of How I Invest, I connect with Matt Hougan, Chief Investment Officer at Bitwise Asset Management. Matt shares his expertise on Bitcoin and cryptocurrency investments, offering actionable insights on portfolio allocation, valuation, and the evolving crypto market. From the benefits of a 2–5% Bitcoin allocation to the potential of Bitcoin as a global settlement currency, Matt provides a compelling case for crypto as a transformative asset class. This episode is a must-listen for institutional investors, financial advisors, and anyone curious about the future of digital assets.

Highlights:

Bitcoin Allocation: Why institutional investors should allocate at least 2% to Bitcoin to stay neutral with benchmarks and up to 5% to maximize risk-adjusted returns.

Portfolio Benefits: Adding Bitcoin improves Sharpe ratios due to its low correlation with traditional assets, offering higher returns with minimal additional volatility.

The Importance of Timeframe: Bitcoin’s performance as a hedge improves over a long-term horizon, despite short-term volatility.

Behavioral Risk: The biggest risk in crypto investing is behavioral, emphasizing the importance of maintaining balanced portfolio allocations.

Beyond Bitcoin: The case for diversifying into other cryptocurrencies like Ethereum, and the advantages of buying a basket of assets versus picking individual winners.

Crypto Cycles: Why crypto markets are highly cyclical due to their early-stage nature and speculative tendencies, and how this volatility is decreasing over time.

Regulatory Clarity: How a pro-crypto regulatory environment under the new U.S. administration could unleash institutional investment and entrepreneurial growth in the crypto space.

Bitcoin Valuation: Using supply-demand dynamics and gold’s $18 trillion market as a benchmark, Matt explains why Bitcoin could eventually reach $1 million per coin.

Bitcoin as a Settlement Currency: The potential for Bitcoin to become a non-political settlement currency in a multipolar world.

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Guest Bio: Matt Hougan is the Chief Investment Officer at Bitwise Asset Management, where he leads the development of innovative crypto investment strategies. A pioneer in crypto asset management, Matt created the first crypto index fund and has been guiding investors through the complexities of digital assets for over seven years. He’s known for his precise, academic approach to crypto and is passionate about helping investors understand the transformative potential of blockchain technology.

Our Podcast now receives more than 200,000 downloads a month. Are you interested in sponsoring an episode? Please email me at dweisburd@gmail.com.

We’d like to thank @ReedSmith for sponsoring this episode!

#VentureCapital #VC #Startups #OpenLP

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SPONSOR: Reed Smith is a dynamic international law firm dedicated to helping clients move their businesses forward. With an inclusive culture and innovative mindset, Reed Smith delivers smarter, more creative legal services that drive better outcomes for their clients. Their deep industry knowledge, long-standing relationships and collaborative structure make them the go-to partner for complex disputes, transactions, and regulatory matters. Learn more at www.reedsmith.com.

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Stay Connected: X / Twitter: David Weisburd: @dweisburd Matt Hougan: @Matt_Hougan

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Matt Hougan: https://www.linkedin.com/in/matthougan/

Links: Bitwise Asset Management: https://www.bitwiseinvestments.com/

Questions or topics you want us to discuss on How I Invest? Email us at dweisburd@gmail.com.

(0:00) Episode preview (1:04) Institutional investment strategies in Bitcoin (4:35) Portfolio diversification with Bitcoin (8:13) Case study: MicroStrategy's Bitcoin strategy (10:03) Exploring other cryptocurrencies for institutional investors (12:45) Advantages of cryptocurrency baskets (14:38) Sponsor: Reed Smith (16:03) Cyclical nature of cryptocurrency markets (19:54) US government and Bitcoin investment prospects (21:42) Crypto's regulatory landscape under the Trump administration (25:40) Bitcoin's future beyond a store of value (27:21) Assessing Bitcoin's value without traditional cash flows (29:08) Bitwise investment strategy overview (30:17) Closing remarks

In this episode of How I Invest, I sit down with Alifia Doriwala, Co-CIO and Managing Director at RockCreek, a multi-asset and OCIO solutions firm managing $16 billion in assets. Alifia delves into RockCreek’s unique approach to managing customized portfolios for endowments, foundations, and pensions. She shares her perspectives on navigating public and private markets, the evolving role of hedge funds, and the outlook for IPOs and M&A activity in 2025. This conversation is packed with insights for asset managers, institutional investors, and anyone seeking a deeper understanding of market trends and investment strategies.

Highlights:

What is RockCreek? A multi-asset and OCIO firm managing portfolios for clients with under $2 billion in AUM, combining private and public market expertise.

Customized Solutions: Tailoring portfolios to meet client needs, including thematic private market investments like innovation in the aviation industry.

Key Themes for 2025: Anticipating a rebound in IPO markets, increased M&A activity, and opportunities in healthcare and biotech within private markets.

Public Markets Outlook: A shift toward active management as market dynamics broaden, with sector-specific opportunities in U.S. equities like energy, pharmaceuticals, and fintech.

Private Markets Allocation: Targeting 20–30% in private equity and venture capital for long-term institutional investors, with 35–40% in alternatives when including real assets.

Interest Rates and Inflation: Insights into the current rate environment and long-term concerns about inflationary pressures due to trade policies and tariffs.

The Role of Hedge Funds: Understanding why institutions are increasing allocations to hedge funds for alpha and downside protection, and the contrasting strategies between discretionary and quant approaches.

Lessons from a 20-Year Career: How starting in sales and trading shaped Alifia’s investment approach and the importance of being data-driven, dynamic, and open to new ideas.

Continuous Improvement: Strategies for sharpening skills as a CIO, including constant learning, engaging with peers, and leveraging diverse macro perspectives.

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Guest Bio:

Alifia Doriwala is the Co-CIO and Managing Director at RockCreek, where she oversees multi-asset portfolios for institutional investors, including endowments, foundations, and pensions. With a career spanning over two decades, Alifia’s expertise bridges public and private markets, offering strategic solutions tailored to client needs. She is passionate about data-driven decision-making, market research, and mentoring the next generation of asset managers.

Our Podcast now receives more than 200,000 downloads a month. Are you interested in sponsoring an episode? Please email me at dweisburd@gmail.com.

#VentureCapital #VC #Startups #OpenLP #AssetManagement

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Stay Connected:

X / Twitter: David Weisburd: @dweisburd

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Alifia Doriwala: https://www.linkedin.com/in/alifia-doriwala-4382629/

Links: RockCreek: https://therockcreekgroup.com/

Questions or topics you want us to discuss on How I Invest? Email us at dweisburd@gmail.com.

(0:00) Episode preview (1:00) Solving client problems and investment themes for the new year (3:26) IPO market predictions and future interest rates (7:08) Alternatives portfolio strategies for endowments and foundations (11:53) Career insights: From sales and trading to investment management (13:30) Family offices' investment trends in hedge funds (16:27) Reflections and advice for aspiring CIOs (17:32) Closing remarks

In this episode of the How I Invest Podcast, I interview David Clark, CIO of Vencap, to discuss the venture capital landscape. We discuss assumptions about small vs. large venture funds, unpack survivorship bias in performance data, and explore the power law dynamics in early-stage and growth funds. David Clark shares Vencap's strategy for identifying top-performing managers, insights on fund size limits, and the implications of political and economic shifts on venture capital. A must-listen for investors seeking a data-driven perspective on navigating the venture ecosystem.

Highlights:

Myth of Small Fund Outperformance: David Clark challenges the belief that smaller venture funds consistently outperform larger ones, noting limitations in available data and survivorship bias.

Survivorship Bias in VC Data: Many underperforming funds don't report their results, skewing datasets like PitchBook and Cambridge. Clark highlights Carta as a potential unbiased source for small fund performance data.

Power Law Dynamics in Venture Capital: Vencap's data shows that even growth funds exhibit power law outcomes, with 1.6% of their investments being fund returners—higher than early-stage funds (1%).

Focus on Top-Performing Managers: Over 90% of Vencap's capital goes to 12-13 managers who have a track record of consistently backing fund-returning companies.

Venture vs. Private Equity: Venture funds show stronger persistence of returns compared to private equity, with top-quartile funds often repeating their success.

Fund Size Considerations: Vencap evaluates whether fund sizes align with the ability to back companies that generate massive returns. Excessively large funds can dilute performance potential.

State of Venture Post-2020 Election: While short-term political changes may influence sentiment, Clark emphasizes focusing on long-term relationships with top managers and founders.

Valuation Practices in Venture: Skepticism over inflated venture fund valuations is warranted, but Clark sees signs that portfolios may now be undervalued.

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Guest Bio: David Clark is the CIO of Vencap, a firm specializing in venture fund investments since the 1980s. With a data-driven approach, Vencap partners with top-performing venture managers to navigate the power law dynamics of venture capital. David’s insights are rooted in decades of data, challenging conventional wisdom and focusing on long-term outperformance in venture markets.

Our Podcast now receives more than 200,000 downloads a month. Are you interested in sponsoring an episode? Please email David Weisburd at dweisburd@gmail.com.

We’d like to thank @ReedSmith for sponsoring this episode!

#VentureCapital #VC #Startups #OpenLP #AssetManagement

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SPONSORS: Reed Smith is a dynamic international law firm dedicated to helping clients move their businesses forward. With an inclusive culture and innovative mindset, Reed Smith delivers smarter, more creative legal services that drive better outcomes for their clients. Their deep industry knowledge, long-standing relationships and collaborative structure make them the go-to partner for complex disputes, transactions, and regulatory matters. Learn more at www.reedsmith.com.

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Stay Connected: Twitter David Weisburd: @dweisburd David Clark: @DaveClark85

LinkedIn David Weisburd: https://www.linkedin.com/in/dweisburd/ David Clark: https://www.linkedin.com/in/david-clark-6678b6b/

Links VenCap: https://www.vencap.com/

Questions or topics you want us to discuss on How I Invest? Email us at dweisburd@gmail.com.

(0:00) Episode preview (3:38) Survivorship bias and its effects on venture capital (11:48) VenCap's investment strategy and return persistence (16:04) Key factors influencing founder choices of investors (16:25) Sponsor: Reed Smith (19:04) Relationship between fund size and performance (20:06) Venture market insights after the 2024 election (23:36) The interplay between startups and investor actions (25:28) What excites LPs about the venture asset class (26:46) Venture fund valuations and market concerns (27:16) The predictive power of TVPI and DPI in venture funds (29:03) Following David Clark online and data-driven investing (31:04) Closing remarks