How I Invest with David Weisburd

What if managing your own capital and not outsourcing it is the highest-return investment decision you can make? In this episode, I talk with Alex Tonelli, Co-Founder of Endurance, about what changes when entrepreneurs manage their own money with the same first-principles thinking they use to build companies. Alex explains how Endurance evolved from a startup holding company into a highly structured family investment office, why principal-driven capital behaves differently than institutional capital, and how disciplined portfolio construction, vintage diversification, and contrarian thinking create durable long-term returns. We also explore why institutions systematically underperform their opportunity set — and how to avoid the behavioral traps that cause it. Highlights:

• Why Endurance was built as a product-market-fit response, not a plan
• How founders turned company building into an investing engine
• Why partners investing their own money changes every decision
• Endowment-style portfolio design with entrepreneur-level risk tolerance
• The “thermostat” approach to adjusting allocations
• Why vintage discipline beats market timing
• Why big brand funds often disappoint over time
• IRR vs. MoIC and why compounding wins
• The free lunch of diversification applied to illiquid assets
• How information flow itself becomes a form of alpha

Guest Bio:

Alex Tonelli is a Co-Founder of Endurance, a private investment office created by a group of serial entrepreneurs to build companies and manage their own capital using first-principles thinking. Before Endurance, Alex co-founded a series of successful enterprises, most notably including Funding Circle, which became the world’s largest small-business lending marketplace and went public in 2018. As Managing Partner at Endurance, he focuses his investment work on portfolio construction, manager selection, and building scalable internal investment infrastructure designed to optimize for long-term compounding rather than institutional constraints.

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

Stay Connected with David Weisburd:

X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/

Stay Connected with Alex Tonelli:

LinkedIn: https://www.linkedin.com/in/n-alex-tonelli-54b2a42/

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

This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

(0:00) Introduction (0:47) Success story of Funding Circle and Collective Medical (1:19) Building the investment office and decision to start investing together (2:01) Overview of Endurance's structure and activities (2:22) Principles behind creating the family office (3:38) Problem-solving: products vs. process/people (4:44) Portfolio construction, internal processes, and decision-making dynamics (6:02) Asset allocation, investment strategy, and market timing (8:52) Valuation dynamics and contrarian views in various market conditions (10:49) Comparison of IRR vs. MOIC in investment decisions (13:15) Expected returns and comparison with institutional endowments (15:45) Principal-agent issues and behavioral factors in decision-making (17:40) Diversification strategy and targeting high-risk assets (18:35) The virtue of illiquidity and reflection on investment strategy mistakes (21:14) David Weisburd on growth and economies of scale in investment brands (26:06) Alex Tonelli on changing investment principles and proactive capital conversations (28:18) David Weisburd on LP check sizes and maximizing returns (32:15) Understanding alpha, portfolio construction, and committee-based challenges (35:05) Balancing external influence with investment integrity (37:12) Influences from legendary investors and evolving strategy (38:19) Investment philosophy contradictions and information diet (39:56) Negative alpha, impact of negative information, and curated sources (41:12) Timeless advice for new investors and biggest COVID-19 investment mistake (43:07) Closing remarks

What kind of entrepreneur decides to bring back extinct species and why might that become one of the most important businesses of our lifetime? In this episode, I talk with Ben Lamm, Co-Founder and CEO of Colossal Biosciences, about why de-extinction is not science fiction but an engineering problem — and how solving it is creating breakthrough technologies across biology, conservation, and medicine. Ben shares how Colossal evolved from a bold idea into a multi-billion-dollar platform, why mammoths, dire wolves, and dodos became cultural gateways into serious science, and how mission-driven companies can attract talent, capital, and public imagination at once. Highlights:

• Why de-extinction is an engineering challenge, not a science breakthrough
• How Colossal is building a “portfolio of species” like products
• Why mammoths and dire wolves are cultural on-ramps to deep tech
• How Form Bio emerged from Colossal’s internal tooling
• Using memes, pop culture, and celebrities to make science mainstream
• Why investor alignment matters more than valuation
• The difference between persuading and educating
• How mission focus drives execution speed
• Why frontier companies require extreme context-switching
• How optionality becomes the ultimate business advantage

Guest Bio: Ben Lamm is a technology entrepreneur and the Co-Founder and CEO of Colossal Biosciences, a company focused on de-extinction, genetic rescue, and biodiversity restoration. He has previously founded and exited multiple companies across software, gaming, and AI, including Chaotic Moon (acquired by Accenture), Team Chaos (acquired by Zynga), and Conversable (acquired by LivePerson). Ben is also a Co-Founder and board member of Form Bio and is known for building ambitious, mission-driven companies that operate at the intersection of science, culture, and technology.

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.

Stay Connected with David Weisburd:

X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/

Stay Connected with Ben Lamm:

LinkedIn: https://www.linkedin.com/in/benlamm/

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

This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

(0:00) Introduction to de extinction, cultural significance, and company future plans (1:03) Scaling genome engineering and business models in synthetic biology (3:27) Potential applications of de extinction technologies and pharmaceutical uses (4:30) Inspiration and initial challenges in starting a de extinction company (5:22) Impact of previous successes and strategies for rapid growth (8:08) Leadership structure and the role of species leads (9:49) Lessons learned from previous ventures and aligning investors (12:34) Foundational principles and media strategy for Colossal (16:44) Worldwide awareness and balancing public narrative with business strategies (21:30) Vision for the next decade and the importance of species reintroduction (24:34) Capital market alignment and strategies for entrepreneurial resilience (27:46) Entrepreneurial mindset, dealing with failure, and the value of freedom (29:28) Episode closing and listener call-to-action

How do you spot a frontier-tech company before it becomes obvious and why is being early so much harder than being right? In this episode, I talk with Jonathan Lacoste, Founder and General Partner of Space VC, about investing at the moment when ideas are still non-consensus. Jonathan explains the difference between deep tech and frontier tech, why founder migration is the strongest signal of emerging opportunity, and how pre-seed investors create alpha by backing contrarian founders before markets agree. We discuss how grit and mission outperform IQ, why concentration beats diversification in early-stage portfolios, and how patience compounds into an edge over time. Highlights:

• The difference between deep tech, frontier tech, and “just tech”
• Why founder migration predicts where value is forming
• Investing before consensus vs. competing after consensus
• Why pre-seed alpha comes from people, not theses
• How grit, obsession, and mission predict founder success
• Why concentration works better than diversification at pre-seed
• How Jonathan evaluates first-time founders before companies exist
• Lessons from building and selling his own startup
• Why hardware and industrial tech are becoming venture-scale
• How patience and restraint compound into long-term advantage

Guest Bio:

Jonathan Lacoste is the Founder and General Partner of Space VC, a pre-seed venture firm backing frontier technology startups across space, defense, energy, robotics, autonomy, and physical AI. Before founding Space VC, Jonathan co-founded an enterprise software company that was later acquired by Vista, and he became one of the youngest founders to raise venture capital at age 19. He brings a founder-first approach shaped by firsthand experience building through multiple pivots, near-failures, and a successful exit. Originally from Ohio, Jonathan has spent over 15 years as a founder, investor, and advisor working with some of the most technically ambitious teams in the world.

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.

Stay Connected with David Weisburd:

X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/

Stay Connected with Jonathan Lacoste:

LinkedIn: https://www.linkedin.com/in/jonathanlacoste/

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

This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

(0:00) Introduction (0:42) Impact of economic conditions on startup formation and differences between deep tech and frontier tech (4:02) Transitioning from deep tech to mainstream with examples (6:12) Non-consensus investing and its importance for emerging managers (9:21) Understanding the two asset classes within venture capital (10:15) The significance of founder migration from top tech companies (12:16) Comparing thesis-led and founder-led investment approaches (18:48) The role of grit in hard tech entrepreneurship and Jebbit's challenges (24:16) Jonathan Lacoste's background and the concept of grit in startups (27:47) Mission orientation in founders and its impact on startup success (29:13) Effects of large liquidity events on founder motivation (30:29) Economic rationale for investing in frontier tech startups (32:32) Evolution of investment strategies from fund one to fund two (35:02) Communicating strategy and differentiation to LPs and aligning with them long-term (40:54) Advice on recognizing excellence and patience in capital deployment (43:48) Differences between successful entrepreneurs and VCs (45:06) Closing remarks

What if the most important decision in wealth planning isn’t the tax strategy—but who you trust to make decisions when you no longer can? In this episode, I talk with Thomas Monroe, Founder and President of Blue Sky Trust, about the real role of a trustee and why independence, judgment, and governance matter more than technical structuring alone. Thomas explains how trustees sit at the intersection of tax, legal, investment, and family dynamics—and why poor trustee selection can quietly undermine even the most sophisticated planning. We explore real-world trust use cases, parenting and purpose across generations, and how thoughtful structuring creates optionality without eroding values. Highlights:

• Why a trustee is a trusted advisor, not a commodity service
• The trustee as the “quarterback” of complex advisory teams
• Why independence is essential for both tax efficiency and judgment
• Common trust use cases beyond estate tax minimization
• Pre-liquidity planning and valuation discounting before exits
• The control paradox: why giving up control enables better outcomes
• Raising grounded, purpose-driven children with significant wealth
• Avoiding “trust fund baby” outcomes through structure and intent
• Why optionality matters more than optimization
• How governance and accountability keep the “Ferrari” running properly

Guest Bio:

Thomas Monroe is the Founder and President of Blue Sky Trust, a Nevada-chartered independent trust company serving ultra-high-net-worth families, entrepreneurs, and multigenerational family offices. With more than 25 years of experience, Thomas advises families and their advisory teams on sophisticated trust, estate, tax, and philanthropic planning, with a focus on governance, execution, and long-term alignment. He is widely recognized for bridging technical rigor with practical decision-making and for helping families navigate complexity while preserving flexibility, purpose, and family cohesion 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 david@weisburdcapital.com.

Stay Connected with David Weisburd:

X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/

Stay Connected with Thomas Monroe:

LinkedIn:https://www.linkedin.com/in/thomasmonroe/

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

This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

(0:00) Introduction (4:40) Understanding trusts: Who needs them and use cases (6:43) Tax considerations in trust planning (9:15) Tackling the "trust fund baby" stereotype and parenting (14:29) Fostering children's independence and passions (19:57) Trust structuring best practices and life exploration (22:30) Trust control vs. tax benefits and trustee independence (27:45) Institutional trustees and dealing with mortality (31:50) Managing trust complexity and administration (35:00) Gaining insights from diverse client experiences (37:20) Lessons from the successful and spotting opportunities (41:00) Key takeaways and choosing the right trustee (43:30) Closing remarks

What happens when you throw out the playbook of traditional private equity and instead build businesses with permanent capital, no exits, and no management fees? In this episode, I talk with Brent Beshore, founder and CEO of Permanent Equity, about a radically different approach to investing that focuses on ownership, compounding, and alignment with operators over decades—not years. Brent explains why avoiding leverage and fees isn’t just philosophically different but materially better for long-term outcomes, how Permanent Equity partners with founders who want legacy and culture to endure, and why patient reinvestment beats short-term optimization. We break down how permanent capital accelerates growth, how to think about cash flow vs. IRR optics, and the unique investor mindset required to succeed outside the traditional private equity model. Highlights:

• Why Permanent Equity uses permanent capital instead of typical PE fund structures
• How removing planned exits changes decision-making and drives better outcomes
• No management fees and minimal debt: aligning incentives with operators
• The power of long-term compounding inside small businesses
• Why distribution timing matters less than reinvestment discipline
• How culture and legacy factor into acquisition decisions
• The “cell phone test”: evaluating leadership and partnership quality
• Using downturns to make strategic progress rather than panic reactions
• Why cash flow is the core driver of long-term wealth creation
• How Permanent Equity thinks about growth vs. margin optimization
• Lessons on patience, discipline, and the psychology of long-term investing

Guest Bio:

Brent Beshore is the founder and CEO of Permanent Equity, an investment firm that acquires and builds small businesses with permanent capital and a long-term orientation. Unlike traditional private equity, Permanent Equity doesn’t plan exits or charge management fees, instead focusing on sustained cash flow growth, minimal leverage, and deep partnership with operators. Brent has spent his career refining this approach to deliver compounding outcomes across cycles by aligning incentives between investors and founders and giving businesses the time horizon they need to thrive. Under his leadership, Permanent Equity has developed a reputation for thoughtful acquisitions, disciplined reinvestment, and a culture-first approach to building enduring companies.

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.

Stay Connected with David Weisburd:

X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/

Stay Connected with Brent Beshore:

LinkedIn:https://www.linkedin.com/in/brentbeshore/

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

This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

(0:00) Introduction (1:31) Compounding growth and institutional investor perspectives (4:34) No management fee structure and staff incentives (7:05) Responsible use of debt and industry buying opportunities (12:51) Differentiating from traditional private equity (16:02) Portfolio diversity and the cell phone test (20:07) Handling difficult personalities and problematic investments (23:22) LP relationships, trust, and long-term business views (28:28) The importance of quality in investments (30:55) Closing remarks

Why do so many strong GPs struggle to raise capital today and what actually separates fast, oversubscribed fundraises from stalled ones? In this episode, I talk with Alexander Russ, Senior Managing Director at Evercore and Head of North America for the firm’s Private Funds Group, about what really drives fundraising success in today’s crowded private markets. Alex breaks down the psychology of LP decision-making, why momentum in the first close matters more than almost anything else, and how the best GPs differentiate themselves through narrative, preparation, and credibility rather than fee discounts. We dive into why fundraising is ultimately a momentum machine, how to engineer demand early, and why trust—built over years—can be lost in a single raise. Highlights:

• Why the first close determines the outcome of an entire fundraise
• The three golden rules of fundraising: preparation, control, and narrative
• Why LPs invest based on excitement, not fear or fee discounts
• How oversupply of GPs has changed LP behavior
• The real meaning of “nailing the narrative” in the first 5 minutes
• Why momentum beats aspiration when setting fund size targets
• How credibility compounds or collapses across fundraising cycles
• The danger of weak first closes and getting stuck “in the doldrums”
• Why LP relevance matters more than broad outreach
• How placement agents actually add value by filtering, not flooding

Guest Bio:

Alexander Russ is a Senior Managing Director at Evercore and Head of North America for the firm’s Private Funds Group, which he helped found in 2010. He advises general partners on competitive positioning, fundraising strategy, and execution across private equity, credit, infrastructure, and alternative strategies. Prior to Evercore, Alex worked at Neuberger Berman and Lehman Brothers, where he focused on alternatives advisory, capital raising, and distribution of hedge fund and liquid alternative products across the U.S. and Europe. He began his career in investment banking at Lehman Brothers and graduated with honors from Amherst College.

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.

Stay Connected with David Weisburd:

X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/

Stay Connected with Alexander Russ:

LinkedIn:https://www.linkedin.com/in/alexander-russ-610a0939/

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

This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

(0:00) Introduction (1:49) Key factors for a successful first close and strategies without fee concessions (6:07) The role of excitement and fear in LP investment decisions (9:30) Importance of credibility, long-term relationships, and a compelling narrative (18:25) Evolving fundraising strategies in a competitive market (24:53) Building credibility and effective communication with LPs (31:49) Best practices for the first meeting with an LP and setting fund targets (37:47) Improving the efficiency of the fundraising process and consequences of missing targets (40:09) Raising a smaller fund versus a bigger target and expedited processes (42:10) Golden ratio in LP cutbacks and securing allocations impact (44:47) Balancing LP relationships and demand with ideal outcomes (46:05) Importance of storytelling and relationships in fundraising (46:34) Value of placement agents for GPs (47:30) Closing remarks

Do private markets actually outperform public markets once you properly adjust for risk or is that belief built on flawed data? In this episode, I talk with Dr. Gregory W. Brown, one of the leading academic researchers in alternative investments, about what decades of data really say about private equity, venture capital, and risk-adjusted returns. We break down why private-market performance is so hard to measure, how tools like the Kaplan–Schoar PME changed institutional thinking, and what investors misunderstand about beta, volatility, and alpha. Greg also explains why buyouts and ventures behave very differently, how fund size and geography affect outcomes, and what this research implies for building diversified portfolios today. Highlights:

• Why alternatives are still under-researched compared to public markets
• The core data problem in measuring private-market returns
• How the Kaplan–Scholar PME creates apples-to-apples comparisons
• Buyouts vs. venture: radically different risk profiles
• Why buyout funds show positive alpha and venture largely does not
• What beta actually measures (and why volatility is misunderstood)
• The risk of ruin in high-beta, undiversified portfolios
• Why small funds have higher upside but require real manager selection skill
• Persistence of returns: partners matter more than firms
• How public-market bubbles change private-market relative performance

Guest Bio:

Gregory W. Brown is a Distinguished Professor of Finance at UNC Kenan-Flagler Business School and one of the world’s leading experts on alternative investments, financial risk, and derivatives. He is the founder and research director of the Institute for Private Capital and has held leadership roles including Executive Director of the Kenan Institute of Private Enterprise. Greg’s research has been published in top academic and practitioner journals, and he serves on the board of the CAIA Association. His work bridges academia and practice, helping institutional investors better understand private markets through rigorous, data-driven analysis.

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.

Stay Connected with David Weisburd:

X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/

Stay Connected with Gregory W. Brown:

LinkedIn: https://www.linkedin.com/in/gregory-brown-unc/

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

This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

(0:00) Introduction (2:00) Explanation and Insights from the Kaplan Shore Index (7:04) Risk and Alpha: Buyouts vs. Venture Capital (10:39) Fund Size and Returns Dispersion in Buyouts (15:08) Persistence of Returns and Incentives in Public Pension Investments (19:44) Value Creation Skills and the Impact of the Mag Seven (22:00) Future Outlook and Historical Performance in Private Equity (23:27) Game Theory, Valuations, and Diversification Strategies (25:05) Closing remarks

Why do most investors fail at the exact moments when staying invested matters most—and how can options help fix that? In this episode, I talk with Hamilton Reiner, Managing Director at J.P. Morgan Asset Management and CIO of the U.S. Core Equity Team, about how options can be used not for speculation, but to create discipline, manage risk, and help investors stay invested through market volatility. Hamilton shares lessons from more than three decades managing equities and derivatives, explains why volatility is misunderstood, and breaks down how hedged strategies, rebalancing, and risk-based portfolio construction can dramatically improve long-term outcomes—without requiring heroic market timing. Highlights:

• Why options are about precision, not leverage
• Hedging vs. income: the two primary institutional use cases for options
• How downside buffers help investors stay invested during drawdowns
• Why volatility is a feature of equities, not a flaw
• The biggest behavioral mistakes investors make in up and down markets
• Why missing the best days destroys long-term returns
• How rebalancing quietly outperforms market timing
• The role of options inside a modern 60/40 portfolio
• Why risk tolerance—not asset allocation—should come first
• Lessons from 2008, 2020, and decades of market cycles
• The underrated power of compounding and staying in the game

Guest Bio:

Hamilton Reiner, managing director, is CIO of the U.S. Core Equity Team, Head of U.S. Equity Derivatives for J.P. Morgan Equity Asset Management, and a portfolio manager. He has been managing U.S. equities and U.S. equity derivatives for over 30 years, at firms such as Barclays Capital, Lehman Brothers, and Deutsche Bank. He started his career at the options investing firm O’Connor and Associates, where he developed his passion for derivatives investing. Hamilton obtained a B.S.E. in Finance from the Wharton School of the University of Pennsylvania.

Our Podcast now receives more than 300,000 downloads a month. Are you interested in 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.

Stay Connected with David Weisburd:

X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/

Stay Connected with Hamilton Reiner:

LinkedIn: https://www.linkedin.com/in/hamilton-reiner-7033594b/

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

This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

(0:00) Introduction (0:32) Understanding Options: Strategies and Historical Use (4:20) Managing Stock Gains and Behavioral Biases in Investing (8:16) The Importance of Risk Tolerance and Market Timing (18:27) Decision-Making Challenges in Institutional Investment (22:17) Market Uncertainty and the Role of the VIX (24:14) Volatility, Investment Sizing, and Portfolio Integration (30:18) Market Cycles, Behavioral Biases, and Career Advice (38:23) Key Investment Lessons and the Power of Compounding (43:09) Closing remarks

Why do the most successful investors and founders still miss their best opportunities—and how much of that comes down to poor relationship management? In this episode, I talk with Patrick Ewers, founder of Mindmaven, about why relationships—not intelligence or effort—are the true limiting factor in professional success. Patrick shares lessons from being an early employee at LinkedIn under Reid Hoffman, coaching partners at top firms like Sequoia and Andreessen Horowitz, and building a systemized approach to relationship management that scales. We break down why important things lose to urgent ones, how delegation and leverage unlock effectiveness, and why small, consistent actions compound into billion-dollar outcomes. Highlights:

• Why relationships are the highest-leverage asset in investing and leadership
• The “importance vs. urgency” trap that causes missed opportunities
• How poor follow-up—not bad judgment—creates most investing regrets
• Practical delegation systems that free up 10–12 hours per week
• Why dictating follow-ups is more thoughtful than typing them
• Inbox shadowing and decision triage for leaders
• How to make people feel valued without fake niceness
• Why efficiency enables deeper, more authentic relationships
• The role of thinking time (“white space”) in elite performance
• Why relationship management is the CEO’s final job

Guest Bio:

Patrick Ewers is the founder of Mindmaven, an executive coaching firm focused on helping leaders unlock their full potential through relationship management. He was one of the earliest employees at LinkedIn, working closely under Reid Hoffman, and later became one of Silicon Valley’s most sought-after relationship coaches. Over the past 15 years, Patrick has coached hundreds of founders, executives, and investors, including leaders from firms such as Sequoia Capital, Andreessen Horowitz, Benchmark, and First Round Capital, as well as companies like Reddit, Roblox, and Thumbtack. He is the author of Radical Delegation and has been recognized by Forbes as one of Silicon Valley’s top relationship management experts.

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. Stay Connected with David Weisburd:

X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/

Stay Connected with Patrick Ewers:

LinkedIn: https://www.linkedin.com/in/patrick/

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

Disclaimer:

This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

(0:00) Introduction (1:00) Early career and importance of relationships in business (2:40) Challenges and consequences of neglecting relationships (6:50) Best practices for managing and delegating relationships (10:48) Techniques for efficient business communication (18:25) Balancing transactional and thoughtful relationships (24:29) Strategies for effective meetings and scheduling (27:08) Principles and tools for effective delegation (35:59) Psychological aspects and predictability in email management (41:07) Democratizing executive-level efficiency and avoiding micromanagement (44:26) Leveraging recruiting for sustainable advantages (47:32) Role of relationship management in founding a company (49:09) Best practices for unstructured thinking and managing time (54:19) Overcoming work ambiguity and optimizing thinking environments (55:47) How to collaborate with industry experts (57:36) Closing remarks

How do the best venture investors consistently spot unicorn founders before the rest of the market even knows they exist? In this episode, I talk with Jamie Lee, Co-Founder and Managing Partner of Tamarack Global, about sourcing asymmetric deal flow in deep tech and why founder referrals are the single strongest signal of future breakout companies. Jamie explains how Tamarack applies hedge-fund-level diligence at the seed stage, why intuition and pattern recognition matter as much as data, and how concentrated conviction—combined with relentless research—drives their unusually high unicorn hit rate. We also explore humanoid robotics, labor automation, and why the next industrial revolution is already underway. Highlights:

• Why founder referrals outperform every other sourcing channel
• Venture beta vs. true asymmetric alpha
• Applying hedge fund diligence to pre-seed and seed investing
• Why most early-stage investors under-diligence founders
• The power of intuition and “gut scores” in decision-making
• Lessons Jamie learned from Philippe Laffont at Coatue
• Why long-term time horizons matter more than near-term metrics
• The humanoid robotics market and the $40T global labor opportunity
• Playing offense by preempting rounds in breakout companies
• Why conviction beats caution early in an investing career

Guest Bio:

Jamie Lee is the Co-Founder and Managing Partner of Tamarack Global, an early-stage deep-tech venture capital firm investing across defense, aerospace, robotics, advanced manufacturing, AI, and the energy transition. He began his career in derivatives at Goldman Sachs, advised technology companies in special situations at JPMorgan, and later managed a $1.5 billion long/short equity portfolio at Coatue Management. Jamie holds a B.A. in Economics from Williams College and an MBA from Columbia Business School, where he also completed the school’s Deep Value Investing 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.

Stay Connected with David Weisburd:

X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/

Stay Connected with Jamie Lee:

LinkedIn: https://www.linkedin.com/in/jamie-lee-77430382/

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

This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

(0:00) Introduction (0:11) Jamie Lee's sourcing strategy and founder referrals (4:19) Winning competitive investment rounds and the role of due diligence (10:07) Insights from SpaceX and the humanoid robot space (15:34) Learnings from venture funds and lessons from Philippe Lafont (24:19) The interplay of gut instinct and social psychology in investing (30:12) The importance of diligence and pattern matching in manager selection (33:04) Advice for younger investors and predicting high-value outcomes (37:50) Confidence in investment picks and closing remarks (38:05) Closing remarks

How do you scale a growth equity firm from a $52M first fund to $5B across six funds—without losing discipline or trust? In this episode, I talk with Brian Neider, Managing Partner at Lead Edge Capital, about building a durable growth equity platform by combining rigorous metrics with deep relationship-building. Brian shares how Lead Edge created a differentiated LP model centered on high-net-worth individuals who actively support portfolio companies, why communication and education compound trust over decades, and how a strict investment framework helps avoid negative alpha as the firm scales. We also discuss why exits matter more than paper gains, how to think about “walking dead” portfolio companies, and what truly energizes long-term investing. Highlights:

• Why Lead Edge raised its first fund from individuals, not institutions
• How 700+ LPs became a competitive advantage, not a liability
• The importance of disciplined metrics before falling in love with founders
• How structured LP engagement improves deal sourcing and outcomes
• Why communication, education, and transparency compound trust
• The danger of “negative alpha” and unstructured decision-making
• How pattern recognition scales exponentially—but portfolio work does not
• Why exit planning should start on day one
• The hardest part of growth equity: managing the “walking dead”
• What motivates Brian most after more than a decade of investing

Guest Bio:

Brian Neider is a Managing Partner at Lead Edge Capital, where he helps oversee the firm’s investment strategy, portfolio management, and operations. He is a member of the firm’s Investment, Disposition, and Management Committees and has led or co-led investments in companies including Toast, Asana, Duo Security, Lucid, Amplitude, and Workhuman. Prior to joining Lead Edge in 2012, Brian invested at Bessemer Venture Partners and FTV Capital, focusing on mid-market growth opportunities across software, internet, and business services. He holds a B.S. in Economics from the Wharton School and an MBA from Columbia Business School and is based in New York.

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 with David Weisburd:

X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/

Stay Connected with Brian Neider:

LinkedIn: https://www.linkedin.com/in/brian-neider-7774041/ Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

Disclaimer:

This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

(0:00) Introduction (1:20) The first fund, early advice, and challenges with institutional investors (5:33) Building and managing relationships with investors (12:06) The role of LP dinners, NextGen events, and full-time engagement teams (17:01) Key metrics and strategies for investment selection (21:32) Competitive market strategies and the value of LP introductions (25:35) Utilizing introductions, advice, and understanding growth factors (32:40) Addressing challenges with portfolio companies and LP feedback (38:14) People-centric opportunity filtering and advice for early-stage LeadEdge (42:37) Comprehensive framework and strategies around exits (45:16) Closing remarks

How do you build portfolios that survive liquidity crises, inflation shocks, and the most volatile market regimes in modern history? In this episode, I talk with Alfred Lee, Deputy Chief Investment Officer at Q Wealth Partners and one of Canada’s most experienced multi-asset portfolio architects. Alfred previously managed over $75 billion across equities, fixed income, commodities, factor strategies, and thematic ETFs at BMO—while also spending a year at the Bank of Canada running part of its quantitative easing program during the pandemic. He shares what he learned from overseeing $25B in fixed income and $50B in equities, how ETFs transformed the public markets, why alpha is harder to generate than ever, and why alternatives, real assets, CTAs, and discretionary macro strategies must anchor the next generation of portfolios. Highlights:

• Lessons from overseeing $75B across fixed income, equities & commodities
• What Alfred learned managing QE operations at the Bank of Canada
• Why generating alpha in public markets is harder than at any point in history
• How Q Wealth Partners serves as Canada’s version of a modern RIA aggregator
• Building model portfolios using open architecture while staying within regulatory guardrails
• The “debasement regime”: why inflation will appear in bursts for years
• Why CPI understates real-world cost of living and what that means for investors
• How to allocate to Bitcoin, gold, and real assets through one-ticket solutions
• 60/40 is outdated: Alfred’s 50/30/20 framework for the next decade
• Behavioral finance as the biggest driver of investor outcomes
• Why illiquidity is a feature, not a bug—and the “virtue of staying invested”
• How to evaluate private credit, private equity, and alternative strategies
• Why liquidity collapses cause correlations to spike across asset classes
• How to run “portfolio war games”: preparing for the next crisis
• The single greatest lesson Alfred learned from 2008 and 2020: never assume liquidity

Guest Bio:

Alfred Lee is the Deputy Chief Investment Officer at Q Wealth Partners, where he oversees portfolio construction, asset allocation, and investment platform design for one of Canada’s fastest-growing wealth platforms. Before joining Q Wealth, Alfred spent over a decade at BMO, where he helped grow its ETF franchise to $100 billion in assets and managed more than $75 billion across fixed income, equities, commodities, and factor strategies. He previously completed a one-year secondment at the Bank of Canada, where he ran part of the central bank’s quantitative easing program during the pandemic, helping restore liquidity and functionality to the provincial bond and funding markets.

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 #startupsuccess #openlp #assetmanagement

Stay Connected with David Weisburd:

X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/

Stay Connected with Alfred Lee:

LinkedIn: https://www.linkedin.com/in/alfred-lee-cfa-cmt-dms-b329025/ Q Wealth Partners: https://www.qwealth.com/

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

This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

(0:00) Introduction (0:39) Influence of mentors in Alfred's career & building an asset management firm (2:23) Launching a gold bullion fund & overview of Q Wealth Partners (4:38) Portfolio allocation strategies and views on alternatives (8:49) Inflation, purchasing power, and philosophy on Bitcoin and gold (11:55) Behavioral finance and modernizing the 60/40 portfolio (18:19) Mapping portfolio construction with privates and diversification (23:26) Addressing the J-curve effect and interval funds usage (27:44) Handling unique investment opportunities and avoiding deworsification (32:13) Adding investments and the importance of uncorrelated returns (39:05) Timeless advice and managing liquidity during crises (41:51) War games and crisis preparation for asset managers (44:14) Closing remarks

What does it take to build a sovereign wealth fund from scratch—and still outperform in some of the hardest markets in decades? In this episode, I talk with Peter Madsen, Chief Investment Officer of the Utah School & Institutional Trust Funds Office (SITFO), one of the most quietly sophisticated sovereign wealth funds in the United States. Peter shares how he went from running hedge fund portfolios in London to becoming the first investment hire tasked with modernizing Utah’s endowment. We break down SITFO’s philosophy on mean reversion, factor-based investing, public vs. private markets, active vs. passive strategy, and how a small CIO team competes with far larger institutions. Peter also explains why small caps are broken, how he shifted capital into private equity, why micro-VC funds outperform mega-funds, and how SITFO uses AI and collaborative models to underwrite managers in a world of overwhelming information. Highlights:

• Why Peter left London to build a sovereign wealth fund with permanent capital
• The decline of fund-of-funds—and how it shaped his CIO philosophy
• Why mean reversion still matters, even when markets feel one-sided
• Active vs. passive: why benchmarks themselves are an “active decision”
• Why small caps are structurally different today—and no longer reliably outperform
• The “equal-weighted portfolio” origin story and how SITFO built asset allocation from scratch
• Why SITFO shifted capital from small caps into private equity
• How micro-VC funds outperform large venture funds mathematically
• Why SITFO partners with seed funds, super angels, and Fund I/Fund II managers
• The collaborative LP model: revenue-sharing, co-invest structures, and research leverage
• How SITFO built a zero-and-zero co-invest platform to recapture fee drag
• Using AI to screen manager decks, extract underwriting criteria, and systematize memo writing
• Why sovereign wealth fund investing differs from pensions and endowments
• Managing cashflows from land revenues while protecting K–12 distributions
• Why Sharpe ratio optimization is misleading for long-horizon investors
• Factor modeling, Venn by Two Sigma, and designing purpose-driven portfolios

Guest Bio:

Peter Madsen is the Director and Chief Investment Officer of the Utah School & Institutional Trust Funds Office (SITFO), where he has led the state’s sovereign wealth fund since 2015. He previously served as a Managing Director at Cube Capital in London and as a Partner at RVK, advising large institutional investors on global portfolios, governance, and asset allocation. At SITFO, Peter has overseen the evolution of the fund from a more traditional portfolio into a globally diversified allocator across public and private markets, grounded in mean reversion, factor-based risk management, and long-term stewardship for Utah’s public education system. 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 #interview #podcast

Stay Connected with David Weisburd:

X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/

Stay Connected with Peter Madsen:

LinkedIn: https://www.linkedin.com/in/pmads/

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

This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

(0:00) Introduction (2:02) Assessing fund managers and market conditions; Active vs. passive investing (7:22) Shift from small cap to private equity; Diversification and asset allocation (11:46) Factor exposure and tools for analysis in investment strategies (16:08) Investment strategy and evaluation in venture capital (23:03) Collaborative model and structuring co-invest accounts for better returns (27:10) Utilizing AI tools in investment screening (31:51) Sovereign wealth fund investing insights (32:55) Closing remarks

How do you turn distressed opportunities into structural alpha—again and again—in an asset class most investors still misunderstand? In this episode, I’m joined by Philip Benjamin, Co-Founder and Managing Partner of Colzen Capital, about how he built a differentiated pre-exit liquidity strategy that serves founders, executives, and investors simultaneously. Philip shares how his fourth-generation real estate background and the 2008 financial crisis shaped his investing worldview, how he applies a distressed-real-estate mindset to late-stage ventures, and why Colzen’s structured equity financing model creates downside protection, aligned incentives, and access to elite companies long before IPO. We also discuss portfolio construction, expected return math, founder psychology, and why this emerging asset class is quietly becoming massive. Highlights:

• How the global financial crisis shaped Philip’s investment philosophy
• The real-estate insight that led to Colzen’s equity financing model
• How Philip helped create a solution for executives facing the 90-day exercise deadline
• Why founders want liquidity without selling—and how Colzen solves that
• The investor’s advantage: downside protection, PIK interest, and equity participation
• Why late-stage venture outcomes cluster between 0.7x–3x—and how to systematize that
• Understanding structural alpha vs. manager alpha in Colzen’s model
• How to underwrite companies past binary risk and still outperform
• The psychology of founders choosing Colzen over selling secondary
• Why pre-exit liquidity is already a $60B asset class
• Education as the bottleneck—and why this market will become mainstream
• Why diversification across industries matters even within structured finance
• Building long-term LP relationships and evolving from Fund I to Fund II
• Creating win-win transactions: non-zero-sum liquidity for founders and investors
• The family-office analogy of planting, harvesting, and replanting new seeds

Guest Bio:

Philip Benjamin is the Co-Founder and Managing Partner of Colzen Capital, where he leads one of the most innovative structured equity financing strategies in the late-stage venture ecosystem. Philip’s investment philosophy is informed by his fourth-generation real estate family background and by experiencing the 2008 financial crisis just as he graduated college. His family’s timely liquidity event before the crash enabled him to explore private alternatives and eventually develop a distinctive approach to venture risk.

Before launching Colzen, Philip invested across fund managers, direct deals, and special situations, eventually partnering with Sam Buleau to refine a pre-exit liquidity model that supports founders and executives without forcing them to sell shares. Philip applies a distressed-real-estate mindset to venture—focused on downside protection, valuation discipline, and structured upside—and has become a leading voice in the growing pre-exit liquidity asset class.

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 #startupsuccess #openlp #assetmanagement

Stay Connected with David Weisburd:

X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/

Stay Connected with Philip Benjamin:

LinkedIn: https://www.linkedin.com/in/philip-h-benjamin/ Colzen Capital: https://www.linkedin.com/company/colzen/

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

This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

(0:00) Introduction (1:12) Transitioning to private alternatives and founding Colson (2:16) Mentorship and early real estate investment strategies (4:17) Creation of the equity financing model and navigating market crashes (6:34) Fund formation, strategy, and comparison to private equity (8:03) Value proposition for founders and executives (11:22) Investment strategy, decision-making, and expected returns (18:01) Evolution from Fund One to Fund Two and structural alpha (21:48) Expanding investor access and synergy in the venture space (24:10) Trends in pre-exit liquidity solutions and staying private (27:36) LP feedback and the importance of diversification (33:55) Relationship management and collaboration opportunities (37:50) The family office business and value creation (40:49) Decision-making and planning for future generations (41:32) Closing remarks

What does it take to build four top-decile crypto funds in one of the most volatile asset classes on earth? In this episode, I talk with Rennick Palley, Founder of Stratos, about how he approaches crypto investing with a disciplined, mathematically grounded framework. We break down how Stratos constructs top-performing venture and liquid portfolios, why crypto is shifting from momentum-driven trends to fundamentals, how to size positions without blowing up, and why Bitcoin and gold are behaving the way they are in today’s macro environment. Rennick also shares his philosophy on decisiveness, conviction, and avoiding the costly mistakes investors make when they hesitate. Highlights:

• How Stratos generated four top-decile crypto venture funds
• Why fund size matters more than most crypto investors admit
• Crypto’s evolution from momentum to fundamentals-driven investing
• How to size early-stage positions and avoid portfolio blowups
• Why the smartest investors focus on: “Just don’t screw this up”
• The future of Bitcoin as digital gold
• Why gold is outperforming Bitcoin this year — and why that may change
• What on-chain data reveals about global truth systems
• Why most crypto VC funds underperform the benchmark (just like traditional VC vs. Nasdaq)
• How institutions should think about crypto allocation and volatility
• The behavioral cost of hesitation and the danger of inaction
• Why crypto provides “free leverage” — and why that makes risk management essential
• Thoughts on government seizure scenarios, custody, and ETF risk
• Meme coins, debasement psychology, and the role of speculation
• How investors can compound returns across cycles without blowing up

Guest Bio:

Rennick Palley is the Founder of Stratos, an investment firm he launched in 2016 after entering the crypto markets. Under his leadership, Stratos has built multiple top-decile venture funds and a liquid strategy designed to compound capital across highly volatile cycles. Before founding Stratos, Rennick worked as a Research Associate at Sanders Capital, a $75 billion global equity manager known for its fundamental, value-driven approach. He holds dual Bachelor’s degrees in Applied Mathematics and Mechanical Engineering from Southern Methodist University and a Master’s in Quantitative Finance from the Massachusetts Institute of Technology. Rennick blends value-investing discipline, quantitative rigor, and crypto-native insight, making him one of the most analytical and thoughtful investors in digital assets today.

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 #startupsuccess #openlp #assetmanagement

Stay Connected with David Weisburd:

X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/

Stay Connected with Rennick Palley:

X/Twitter: https://x.com/RennickPalley Stratos: https://www.stratos.xyz/

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

This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

(0:00) Introduction (2:00) Key principles in crypto venture investing (4:18) Analyzing large outcome clustering in crypto (5:12) Momentum vs. value in evaluating crypto wins (8:14) The future of information and crypto as a hedge (12:22) Historical parallels and Bitcoin's potential challenges (17:45) Strategies for a potential Bitcoin confiscation scenario (21:01) Debating Bitcoin's future valuation and effects of forced sales (27:10) Insights from Rennick Palley and liquid crypto strategies (31:34) Comparing crypto to traditional endowment strategies (33:06) Sector importance and risk management in crypto (39:47) Systematic decision-making and the role of an engineering background (43:43) Portfolio construction and institutional crypto allocation (45:52) Transitioning from venture to liquid crypto investments (49:08) The benefits of illiquidity in alternative investments (50:31) Fund liquidity and managing investor relationships (53:10) Determining the optimal portfolio size for Bitcoin (54:13) Utilizing leverage in crypto investing (57:12) Guidance for newcomers to crypto investing (59:45) Closing remarks

How do you build a $10B real estate empire by turning yourself into a media company—and why is vulnerability the ultimate competitive advantage? In this episode, I talk with Ryan Serhant, founder and CEO of SERHANT., one of the most influential real estate brokerages in the world and a pioneer at the intersection of real estate, media, entertainment, and technology. Ryan breaks down the turning points that shaped his career—from selling a $13M townhouse through YouTube a decade ago, to betting everything on social media before anyone believed in it, to building a fast-growing real estate ecosystem powered by content, authenticity, and scale. We dive into Season 2 of Netflix’s Owning Manhattan, the biggest highs and lows of his year, the reality of leading a thousand-agent organization, and why the future of real estate is screenless, human-centric, and powered by creators. Highlights:

• How a YouTube video led to Ryan’s first $13M sale and changed his career
• Why he bet his entire future on social media long before agents believed in it
• The balance between going viral and preserving luxury brand credibility
• The power of authenticity online—and why the internet detects B.S. instantly
• How Season 2 of Owning Manhattan became his most raw and emotional year on TV
• The behind-the-scenes reality of office fights, breakdowns, and $60M deals
• Why vulnerability drives more business than perfection ever could
• The moment he realized he had to evolve from broker-friend to CEO-leader
• What broke at SERHANT. as the company scaled from 500 to 1,500 agents
• The difference between respect vs. trust—and why employees must earn both
• Ryan’s four rules for every new hire, including “perform magic”
• Why culture is defined by the behaviors you allow, not what you write on paper
• The future of content: micro-dramas, interactive media, and 5-minute emotional arcs
• How SERHANT. is building a screenless, AI-powered real estate transaction
• Advice for new agents: join a team, do the work no one wants to do, and get reps

Guest Bio:

Ryan Serhant is one of the most recognized and successful real estate brokers on the planet. He is the founder and CEO of SERHANT., a modern multidimensional real estate brokerage operating at the intersection of media, entertainment, education, and technology. Ryan has closed nearly $10 billion in sales and has represented clients in some of the most record-breaking transactions across New York and South Florida. Before launching his firm, he became a global personality as the star of Bravo’s Million Dollar Listing New York and now serves as Executive Producer and lead star of Netflix’s Owning Manhattan. Beyond real estate, Ryan is an entrepreneur, creator, bestselling author, and philanthropist whose content reaches over six million people. SERHANT. has grown rapidly under his leadership, expanding across multiple states and pioneering LISTED, a dedicated YouTube network focused on real estate and lifestyle. Ryan actively supports organizations including City Harvest, Feeding America, the Ali Forney Center, the NYC Sanitation Foundation, the American Cancer Society, and Project Sunshine. He lives in Brooklyn with his wife, Emilia, and their daughter, Zena.

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.

Stay Connected with David Weisburd:

X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/

###Stay Connected with Ryan Serhant: LinkedIn:https://www.linkedin.com/in/ryanserhant/ Website: https://serhant.com/

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

This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

(0:00) Preview (1:12) Selling a $13 million home via YouTube and the impact of social media (5:40) Authenticity, vulnerability, and balancing content in luxury real estate (12:02) High and low moments, scaling challenges, and leadership (22:29) Special guest insights on season two highlights (24:38) Real-time CEO moments and a major deal gone wrong (27:02) Season two highlights: Miami, Mercedes Benz, and narrative arcs (29:08) Learning from mistakes across seasons one and two (32:06) Discussing the future of content creation and media convergence (34:08) Ryan Serhant's vision for the future of his company (35:53) Advice for new real estate agents and industry insights (37:26) Closing remarks

Why do the world’s best CIOs make investment decisions based on gut — not spreadsheets? In this episode, I’m joined by Julia Rees Toader, CFA, Founding Partner at PrinCap and former Global Head of Portfolio Strategy at Goldman Sachs Asset Management. Julia spent a decade advising sovereign wealth funds, pensions, private banks, and ultra-wealthy families on portfolio construction, risk management, and asset allocation. She shares the biggest lessons she learned from working with the world’s top CIOs — from why diversification rarely drives behavior, to where the smartest allocators take idiosyncratic risk, to how emotions secretly influence the most sophisticated investment decisions. Highlights:

• What Julia learned rising from intern to global head at Goldman Sachs
• The surprising truth: top CIOs make decisions based on emotions + gut, not just models
• Why diversification rarely changes behavior — and why portfolios still converge to “vibes”
• Where the best allocators take idiosyncratic risk without blowing up the portfolio
• Why ultra-wealthy families succeed by leaning into their operating-business advantages
• Home country bias: the hidden 10x overweight that destroys returns
• How to avoid behavioral traps using blind comparisons and rotating devil’s advocates
• Options-based hedging vs. fixed income — and why 60/40 is outdated
• Why avoiding losers matters as much as picking winners
• Why volatility is emotional, not mathematical — and how Julia coaches clients through drawdowns
• The biggest risk mistakes she saw in sovereign wealth funds & global pensions
• The seductive danger of storytelling in investing — from thematic equity bubbles to VC pitches
• How AI will reshape diligence, bias detection, and decision-making

Guest Bio:

Julia Rees Toader, CFA, is the Founding Partner at PrinCap, an independent investment portfolio strategy firm advising institutions, family offices, and high-net-worth individuals on asset allocation, manager selection, and strategic portfolio design.

Before founding PrinCap, Julia served as Head of Portfolio Strategy and Head of Relationship Management at Heritage Holdings, a multifamily office. She previously spent over a decade at Goldman Sachs Asset Management, where she rose from founding intern to Global Head of Portfolio Strategy, advising CIOs of sovereign wealth funds, pensions, private banks, and other large allocators around the world.

Julia began her career in M&A and business development for an early-stage medical device biotech company. She holds a degree in Mechanical Engineering and Computer Science from Princeton University and is a CFA charterholder.

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 with David Weisburd:

X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/

Stay Connected with Julie Rees Toader:

LinkedIn: https://www.linkedin.com/in/julia-rees-toader-cfa-22871030/

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

This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

(0:00) Introduction (2:55) Emotional and qualitative considerations in taking idiosyncratic risks in portfolios (6:04) Flexibility and unique strengths of allocators (7:15) Building meaningful portfolios with high returns (8:30) Options-based hedging strategies (11:29) Overcoming behavioral biases and market timing (14:01) Addressing home country bias in investment committees (17:02) Dynamics and size of effective investment committees (19:12) Role of tax strategy and alpha in investment (22:00) Strategic value and managing portfolio fluctuations (25:18) Tools and client risk tolerance in portfolio risk assessment (28:07) Lessons from transitioning to a family office (30:40) Family office investment strategies and perspectives on risk (34:24) Outsourcing tasks and addressing personal liability in decisions (37:01) Evaluating family office dynamics and resource advantages (39:04) Incorporating AI in investment management (41:04) Timeless advice for new investors and thought experiments with AI (45:22) Market timing and asset class favorability (46:09) Closing remarks

What does it take to build the most dominant FinTech investment bank in the world—starting from a $99 incorporation and a used laptop? In this episode, I speak with Steve McLaughlin, Founder, CEO, and Managing Partner of FT Partners, widely regarded as the leading investment bank in FinTech. Steve has personally closed hundreds of the biggest M&A, capital raise, and IPO advisory transactions in the industry—while pioneering a completely different approach to value creation in investment banking. We cover everything from the humble beginnings of FT Partners, to Steve’s philosophy of “never die,” to his groundbreaking thesis on AI, tokenization, defensibility in FinTech, and why he believes we’re entering a new era of trillion-dollar global financial technology companies. We also dive into the incentives model Steve built that has generated some of the largest fees in the history of investment banking—and why clients keep coming back. Highlights:

• How Steve left Goldman to launch FT Partners during the dot-com crash—with no brand, employees, or clients.
• The “never die” mindset and why consistency compounds in markets.
• FT Partners’ deep-work model: 500-page decks, long-term models, and internal data science.
• How the firm differentiates from Goldman/Morgan Stanley and attracts elite talent.
• The incentives behind nine-figure fees—and why Steve thinks bankers should be paid like PE/VC when they create real value.
• Inside FT Partners’ $25M investment in Model ML and how AI will reshape investment banking.
• Tokenization, stablecoins, and where the next trillion-dollar FinTech giants will emerge.
• Why the strongest FinTech companies embed AI across every function.
• How AI will change deal sourcing, buyer mapping, and global transaction execution.
• The future of FinTech over the next decade—post-AI and fully digital.
• Steve’s views on money, charity, family, and why he still personally handles major client calls.

Guest Bio:

Steve McLaughlin is the Founder, CEO, and Managing Partner of Financial Technology Partners (FT Partners), the leading investment bank focused exclusively on FinTech. Since launching in 2001, Steve has built FT Partners into a globally recognized advisory powerhouse, completing hundreds of the most important transactions across payments, digital banking, crypto, wealth & capital markets tech, InsurTech, healthcare payments, and more.

He has been ranked #1 on Institutional Investor’s “Most Influential Dealmakers in FinTech,” named Investment Banker of the Year, and recognized as the #1 FinTech banker in Silicon Valley by The Information. FT Partners has also won Investment Banking Firm of the Year four times since 2004.

Before founding FT Partners, Steve led the Global Financial Technology Group at Goldman Sachs. He earned his BSBA from Villanova University and his MBA from Wharton.

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 with David Weisburd:

X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/

Stay Connected with Steve McLaughlin:

LinkedIn: https://www.linkedin.com/in/stevemclaughlinftpartners/ FT Partners: https://www.ftpartners.com

Disclaimer:

This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are solely their own and do not represent the views of Weisburd Capital or its affiliates. Participants may hold positions or have other financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are based solely on the opinions of the speaker and are subject to risks and uncertainties. Information discussed in this episode may include third-party data or opinions; while believed to be reliable, such information has not been independently verified. Listeners should conduct their own research and consult their own professional advisors before making any investment decisions.

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com. (0:00) Introductions (0:04) FD Partners origin story, early challenges, and current scale (1:49) Lessons from market downturns and economic cycles on fintech (3:48) Long-term strategy, resilience, and talent strategy (6:34) Innovations in AI and fintech (7:58) Teamwork and the F1 racing analogy (9:47) Traditional banks vs. fintech and value-added roles (15:15) Private markets and client engagement strategies (19:28) Being labeled the world's richest banker and fintech trends (24:58) The future of fintech and AI's impact (29:06) AI's defensibility and pricing in the fintech market (32:07) Competitive differentiation with AI in fintech (33:24) Closing remarks

What does it take to recruit the top 0.1% of engineers in the world — and why has talent become the ultimate constraint in AI? In this episode, I’m joined by Chris Vasquez, Founder & CEO of Quantum Talent, one of the most in-demand technical recruiting firms in the AI ecosystem. We discuss why elite engineering talent has become the core bottleneck in AI, how companies can actually attract S-tier builders, what founders get wrong about hiring, and why talent density—not headcount—is the strongest predictor of outcomes in today’s startup environment. Highlights:

• Why AI founders are “at war” — and recruiting firms are the arms dealers. Defining S-tier talent: clear evidence of greatness, spiky abilities, and proven complexity-handling.
• Capital is abundant; talent is the true constraint in modern AI company building.
• Why companies must tell a compelling story if they lack high-signal founders or top-tier backers.
• How AI’s rapid improvement reshapes recruiting needs — fewer engineers, but far more specialized ones.
• The Sequoia-backed company that failed to hire until they raised their comp bands. (7 declines vs. 17 hires after fixing comp.)
• Why founders should overpay strategically for the roles that matter most.
• Key signals elite engineers look for: founding team quality, investor pedigree, mission clarity, and market upside.
• Why “experience with greatness” de-risks execution in early-stage teams.
• The #1 heuristic Chris wishes he learned earlier: “If you wouldn’t hire 100 of that person, don’t hire one.”

Guest Bio:

Chris Vasquez is the Founder & CEO of Quantum Talent, a specialized recruiting firm focused on placing elite technical talent into leading AI, frontier-tech, and enterprise software startups. Quantum works with hundreds of venture-backed companies and has partnered with 80% of Tier 1 VC firms, helping founders build high-density engineering teams capable of shipping breakthrough products.

With deep expertise in identifying the top 0.1% of engineers, researchers, and product leaders, Chris and his team have become one of the most trusted upstream partners in the AI ecosystem — operating at the intersection of talent, technology, and high-velocity company building.

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.

Stay Connected:

X / Twitter: David Weisburd: @dweisburd

Stay Connected with David Weisburd:

X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/

Stay Connected with Chris Vasquez:

LinkedIn: https://www.linkedin.com/in/chris-vasquez-66137553/ Quantum: https://www.quantumtalent.io/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com. david@weisburdcapital.com. (0:00) Introduction (2:38) Talent Density and the Shift from Capital to Talent in Startups (5:16) AI's Impact on Talent Recruitment and Compensation Strategies (9:45) What S Tier Engineers Seek in Companies (11:14) Establishing Talent Density by Overpaying Initial Hires (14:28) The Role of Talent in Product-Market Fit (17:21) Strategies for Recruiting Top AI Talent (24:01) The Distinction Between Good and S-tier Recruiters (27:43) Effective Recruiting Heuristics and Compensation Tactics (30:23) Managing Internal Politics for High Compensation Hires (31:48) Timeless Advice for Recruiters (34:34) Closing remarks

How do you balance power-law outcomes with real risk management while building a durable venture franchise? In this episode, I speak with Mark Peter Davis (MPD) — Managing Partner of Interplay, entrepreneur, author, podcaster, and one of New York’s most active early-stage investors. We discuss how Mark’s philosophy of investing has evolved over 20 years in venture, why VC psychology is so different from other asset classes, and how he manages for both outliers and consistency across vintages. Mark breaks down secondaries, constructing high-access portfolios, founder relationships, narrative risk, the role of operational support, and why grit compounds just like interest. Highlights:

• How 20 years in venture reshaped Mark’s thinking on risk, liquidity, and exit timing.
• Why early VCs get caught in the “TechCrunch punch” and over-index on hope.
• Power laws vs. portfolio consistency — why vintages swing and how Mark mitigates volatility.
• How secondaries, tenders, and mid-market PE can drive liquidity for the “middle 80%” of winners.
• The “tweener rule”: why Interplay often sells ~50% when outcomes are unclear.
• Incentive alignment between GPs and LPs — and why building a long-term institution changes behavior.
• Avoiding narrative traps: why founder behavior and fund construction matter more than storytelling.
• Brokerage-model VC vs. operational-institutional VC — and why the difference is huge.
• How soft commits, goodwill, and reference strength drive proprietary access.
• Entrepreneurship patterns: the “500 problems” every startup faces.
• Why you can’t learn entrepreneurship in a classroom — only through reps.
• The compounding effect of grit and staying in the game long enough.

Guest Bio:

Mark Peter Davis is a venture capitalist, serial entrepreneur, author, and startup community organizer.

MPD is the Managing Partner of Interplay, a startup ecosystem based in NYC that supports founders and innovation at every stage. The ecosystem comprises a top-performing venture capital fund, an accelerator, a studio, a services platform, and a multi-family office. With over 100 companies funded, incubated, or founded, he ranks among the most active startup founders and investors in New York City.

MPD is also an active podcaster, the author of The Fundraising Rules, and the founder of both the Columbia Venture Community and the Blue (Duke) Venture Community.

Prior to his current ventures, MPD was a venture capitalist at DFJ Gotham Ventures and Primary Ventures. Before entering VC, he was a M&A advisor to Fortune 1000 acquirers at KPMG and a strategy and operations consultant at Bain & Company.

MPD earned his BA from Duke University and his MBA from Columbia Business School.

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 #startupsuccess #openlp #assetmanagement

Stay Connected with David Weisburd:

X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/

Stay Connected with Mark Peter Davis:

LinkedIn: https://www.linkedin.com/in/markpeterdavis/ X/Twitter: https://x.com/mpd Interplay: http://interplay.vc/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com. david@weisburdcapital.com. (0:00) Introduction (0:31) Evolution and counterintuitive lessons in venture investing (3:25) Reconciling investment worldviews and managing liquidity (7:35) Decision-making and aligning VC incentives with LP interests (12:03) Building an enduring institution and measuring success (18:07) Achieving access to competitive deals and proprietary deal flow (24:24) Competitive tension's impact on investment support (27:19) Integrity and resources in VC partnerships (30:02) Entrepreneurial experience's value in venture capital (32:24) Startups' challenges and the role of pattern recognition (35:24) Unlearning and cognitive restructuring in entrepreneurship (37:23) Mastering the complexities of long-term entrepreneurship (38:11) Timeless advice for aspiring entrepreneurs and enduring success (41:51) Closing remarks

How do the best family offices consistently spot power-law opportunities and avoid the trap of “fake busy” work? In this episode, I’m joined with William (Bill) Brown, CIO of the Terrace Tower Group, about the lessons he learned working for billionaire Leonard Stern, how he helped evolve a legacy real-estate portfolio into a globally diversified family office, and what pattern recognition looks like across trades like the Big Short, crypto, and private credit. We discuss how Bill thinks about decision-making, mental models, productivity, and the mindset required to survive long enough to capture asymmetric upside. Highlights:

• Lessons from working under Leonard Stern — focus on what truly matters.
• Why “don’t confuse activity with progress” became a lifelong principle.
• How Stern gathered insights by walking the office and challenging ideas in real time.
• The importance of taking leaders on a journey, not presenting decisions once.
• Batting average vs. slugging percentage — finding your investing style. (Ichiro vs. Aaron Judge)
• Behind the scenes of the Big Short trade — identifying early signals.
• Navigating months of drawdowns and conviction challenges.
• How to know whether you’re the “dumbest person in the room” and avoid confirmation bias.
• Why the best ideas often come from “other herds” and cross-network pattern recognition.
• Crypto pattern recognition — spotting the signal when two very different founders agree.
• How Terrace Tower built a diversified global portfolio from a real-estate foundation.
• Using private credit to replace income after a major asset sale. “Fake busy” vs. deep work — designing days for real thinking.
• Staying in the game long enough to benefit from power-law outcomes.

Guest Bio:

William “Bill” Brown is the Chief Investment Officer of Terrace Tower Group, a global family office originating from the Westfield legacy. Bill oversees the group’s non-real-estate portfolio, spanning public equities, private equity, venture capital, and private credit. Before joining Terrace Tower in 2010, Bill worked in investment banking and spent his early career at Salomon Brothers. His investing philosophy is shaped by decades of experience working with the Stern family and managing multi-asset portfolios across cycles.

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 with David Weisburd:

X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/

Stay Connected with Bill Brown:

LinkedIn: https://www.linkedin.com/in/william-brown-1a48593/ Terrace Tower Group: https://www.ttgroup.co/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com. david@weisburdcapital.com. (0:00) Introduction (0:12) Leonard Stern's investment philosophy and unique work habits (2:16) Leonard Stern's idiosyncratic bets and discussion on risk (4:49) Jeff Bezos and asymmetry in business (5:23) Introduction to and expansion of the big short trade (13:30) Evaluating complex trades as a family office (15:18) Cultivating the right investment mindset (18:53) Early investments in crypto and avoiding busy work (23:02) Energy management and strategic networking (25:10) The importance of not overthinking and perfection in investing (27:03) Resisting the temptation to sell too early (29:13) The importance of staying in the game and imagination in investing (33:19) Terrace Tower Group's current focus and portfolio execution (42:02) Advice for younger self and focusing on what matters (46:42) Closing remarks

How do you scale from a $10M first fund to managing over $1.5B — all in one of the most capacity-constrained asset classes on earth? In this episode, I talk with Eva Shang, Co-founder and General Founder of Legalist, about dropping out of Harvard, getting into Y Combinator, pivoting from legal analytics to litigation finance, and raising their first $10M fund long before they had any track record. We discuss why Legalist chose the fund model over the venture-backed originator model, how they deployed their algorithm to find late-stage cases at scale, why litigation finance is capacity constrained, and how Legalist expanded into adjacent strategies like bankruptcy, mass torts, law-firm lending, and government receivables. Highlights:

• How Legalist began as a data-driven legal-analytics platform.
• Why the team shifted from software to asset management.
• How technology identifies litigation, bankruptcy, and receivables opportunities.
• The role of public-records sourcing and automated case screening.
• Why Legalist focuses on uncorrelated, niche credit strategies.
• How Legalist evaluates risk in litigation finance.
• How the team structures underwriting across legal and credit factors.
• Why government receivables and bankruptcy claims require specialized processes.
• How Legalist works with law firms, claimants, and contractors.
• Eva’s philosophy on building teams, culture, and long-term systems.

Guest Bio:

Eva Shang is the Co-founder and General Partner of Legalist, an asset manager specializing in technology-enabled investments across litigation finance, bankruptcy, law-firm lending, mass torts, and government receivables. Eva co-founded the firm in 2016 after leaving Harvard and entering Y Combinator, and has led Legalist from its $10M debut fund to over $1.5B in AUM across multiple strategies.

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 with David Weisburd: X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/

Stay Connected with Eva Shang: LinkedIn: https://www.linkedin.com/in/eshang/ Legalist: https://www.legalist.com/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com. (0:00) Introduction (2:20) Y Combinator insights and venture capital decisions (4:51) Emphasizing IRR in building a sustainable business model (6:48) Lessons from early fundraising and growth strategies (9:36) Diversification and understanding capacity-constrained assets (13:33) Fundamentals of litigation finance and sources of alpha (18:08) Exploring the government receivables strategy (20:38) Cultivating long-term vision and independent mindedness in entrepreneurship (24:33) Reflecting on past decisions and the importance of team building (26:14) Closing remarks

What does it actually take for an emerging manager to convince a top LP to invest? In this episode, I’m joined by Alex Edelson, Founder of Slipstream, and one of the most respected LPs backing elite seed funds today. Alex pulls back the curtain on how LPs use AI, what “real talk” references look like, how he evaluates GPs, and why only a tiny percentage of funds ever make it through his screening. We also dive into portfolio construction, picking and winning founders, why deep tech requires more shots on goal, and how Alex builds long-term trust with the world’s top institutions. This conversation is a masterclass in LP underwriting and what separates good managers from truly exceptional ones Highlights:

• How top seed funds use AI for sourcing, diligence, and market research.
• Why underwriting venture still comes down to relationships, brand, and founder trust.
• Why Slipstream screens out ~95% of funds before doing references.
• What “real talk references” reveal that most LPs never hear.
• Why deep tech sometimes needs more shots on goal with slightly lower ownership.
• How Alex developed his “right to win” as an LP after QED.
• What GPs misunderstand about the bar for raising today.
• How anti-selling helps LPs filter for long-term partners.
• Why LP relationships often become deep personal relationships over time.
• The frontier of the next decade: AI-driven investing and pre-consensus founder identification.

Guest Bio:

Alex Edelson is the Founder of Slipstream, an LP firm focused on backing top early-stage venture funds. Before launching Slipstream, Alex was part of the leadership team at QED Investors, where he helped shape their approach to portfolio construction, fund strategy, and LP engagement. His legal background and deep relationships across the founder/VC ecosystem have made him one of the most sought-after LP partners for emerging and established seed GPs.

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/ Alex Edelson: https://www.linkedin.com/in/alex-edelson-604767b/

Links Slipstream Investors: https://www.slipstreaminvestors.com/ Weisburd Capital: https://www.weisburdcapital.com/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com. (0:00) Introduction (0:06) Seed funds, AI usage, and diligence processes (1:56) Growing prominence of AI and unique investment approaches (4:00) Constructive GP conversations and Slipstream's strategy (6:11) Comparisons to Palantir and investment beliefs (8:07) Differing views on identifying good GPs (10:55) The importance and role of references in diligence (19:04) Screening out funds and challenges for emerging managers (25:49) Attracting top LPs and building relationships (30:03) The concept of antiselling and excitement for the future (35:17) Closing remarks

What does it really take to raise a venture fund—and why does fundraising never get easier, even at Fund 5 or Fund 6? In this episode, I talk with Yasmine Lacaillade, Founder of Sinefine and one of the most respected capital formation leaders in venture. Yasmine shares her journey from TPG Axon in London to joining Drive Capital at Fund I—years before it became consensus. We discuss why fundraising is always difficult, how LP sentiment shifts every 2–3 years, and why top fundraisers treat the process like enterprise sales rather than relationship maintenance. Yasmine breaks down her market mapping framework, why the top of the funnel must always stay wide, how to qualify LPs quickly, and why “adding value first” is her core operating principle. She also explains how she evaluates new managers, how to identify true LP demand today, and why people, culture, and team cohesion matter more than anything else in venture. Highlights:

• How moving from London to Columbus led Yasmine into the earliest days of Drive Capital.
• Why she joined Drive at Fund I—and what she saw before LPs did.
• Why fundraising never gets easier, even after multiple successful vintages.
• How LP priorities, liquidity, and macro cycles shift every 2–3 years.
• The difference between networking vs. honing existing relationships.
• Why Yasmine treats fundraising like enterprise sales—and why a huge top of funnel is essential.
• What LPs are actually looking for in a first meeting
• How to qualify LPs quickly by asking exactly what they’ve invested in over the last 6–12 months.
• Why the most important skill in fundraising is mapping the market and respecting LPs’ time.
• How Sinefine structures a new engagement with a GP—from deck narrative to LP segmentation.
• Why she only works with a handful of managers and how she selects them.
• How she evaluates team cohesion and founder intensity
• Why her philosophy is to add value before asking for anything.
• The psychology of transactional vs. non-transactional relationships and the idea of “goodwill reservoirs.”
• Why she shut down her fund-of-funds product and how she built Sinefine into a product-oriented platform.
• How Zoom culture has changed LP behavior, time allocation, and transparency.
• The importance of story evolution, narrative sharpening, and portfolio math in venture.

Guest Bio:

Yasmine Lacaillade is the Founder of Sinefine, a capital formation and institutional fundraising advisory firm working with top-tier venture managers. Before launching Sinefine, Yasmine spent over a decade in investment and fundraising roles, including at TPG Axon in London and as an early team member at Drive Capital, where she helped build one of the leading venture franchises in the Midwest from its first fund onward. Yasmine specializes in market mapping, LP strategy, investor relations, and helping emerging and established GPs navigate complex fundraising environments. She is widely recognized for her clarity of thinking, LP intelligence, and ability to guide managers through the entire capital formation journey.

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/ Yasmine Lacaillade: https://www.linkedin.com/in/yasmine-lacaillade-6448888/

Links Sinefine: https://www.sinefine.co/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com. (0:00) Introduction (3:08) Fundraising challenges in venture capital vs. hedge funds (5:00) Networking and managing relationships in fundraising (9:12) Balancing relationships with the transactional nature of fundraising (13:22) Market mapping and targeting LPs effectively (17:02) Long-term investment decisions and adapting to market conditions (21:58) Building trust in first meetings with LPs (27:36) Transactional relationships and adding value in LP-GP dynamics (31:08) Onboarding a new fund and quick trust-building (34:44) Pursuing relationships with potential managers and the Ashton Kutcher investing principle (38:45) Balancing personal and professional commitments (40:06) Embracing people-pleasing as a strength in investing (42:49) Reputation and value creation in the investment world (44:31) Passion for venture capital and finding excitement in buyouts (49:30) Team cohesion and investment success (50:09) Closing

How do LPs unlock liquidity from private-fund positions without selling at a discount? In this episode, I talk with Alex Simpson, Co-founder of Liquid LP, a platform that provides NAV loans backed by LP and GP interests in private funds. Alex explains how NAV loans work, how lenders underwrite illiquid portfolios, and when borrowing may be preferable to selling in the secondary market. We also discuss how different types of investors—high-net-worth individuals, family offices, and institutions—use these loans for personal liquidity, capital calls, tax needs, portfolio rebalancing, or simply as a liquidity backstop. We also cover underwriting, LTV ranges, recourse structures, timing, advisory boards, and the origin story behind Liquid LP. Highlights:

• What a NAV loan is and how LP interests serve as collateral.
• Why some LPs choose a NAV loan rather than selling at a discount.
• How high-net-worth investors use NAV loans for personal liquidity and taxes.
• How institutions use NAV loans for portfolio management and capital calls.
• Differences between Liquid LP and large banks like J.P. Morgan or Goldman Sachs.
• Underwriting approach: fund quality, diversification, existing pledges, and use of proceeds.
• Typical LTV ranges (approx. 20–40%) depending on underlying collateral.
• Loan pricing drivers: asset quality, diversification, and loan structure.
• Loan timelines: from fast two-week processes to more complex multi-week cases.
• Recourse vs. non-recourse structures and when each applies.
• Why purpose of the loan matters for underwriting, even if terms are asset-driven.
• Standby NAV lending partnerships with funds to support LP liquidity.
• How GPs sometimes use loans to bridge GP commitments when DPI is slow.
• How Alex built Liquid LP, beginning with pre-IPO lending before shifting to LP liquidity solutions.
• Key risks in NAV lending: undisclosed pledges, documentation issues, and thin data on smaller funds.
• Lessons learned from building an advisory board and aligning incentives.

Guest Bio:

Alex Simpson is the Co-founder of Liquid LP, a fintech platform that provides NAV-backed lending solutions for LPs, GPs, family offices, and wealth-management clients. Before founding Liquid LP, Alex built and operated companies in South Africa and Australia and worked closely with executives at late-stage and pre-IPO technology companies. His experience in private markets, lending, and alternative-asset liquidity led him to develop a platform focused on helping investors access liquidity without selling long-term positions.

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.

Stay Connected:

X / Twitter: David Weisburd: @dweisburd

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Alexander Simpson: https://www.linkedin.com/in/alsimpson1/

Links LiquidLP: https://www.linkedin.com/company/liquidlps/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com. (0:00) Introduction (1:07) Scale of operations, target clientele, and market rates (2:29) Use cases for institutions and competition with large banks (4:04) Due diligence and factors influencing loan terms (8:15) Recourse vs nonrecourse loans and loan's purpose (10:37) NAV loans for investment stability and GP commit solutions (12:46) Flexibility and risk assessment in lending (15:07) Loan durations, processing times, and standby partnerships (18:22) GP stakes field and LiquidLP's origin and evolution (21:04) NAV loan risks and managing an advisory board (24:34) Advisory board strategy and balancing impact with finance (27:52) Company culture, leveraging finance for impact, and unifying principles (34:25) Closing remarks

What makes a GP interest valuable — and how do you evaluate a manager beyond the fund they’re raising today? In this episode, I talk with Mark Wade, CAIA, Partner at CAZ Investments, about how his team assesses GP interests, private-market managers, partnership structures, and long-term durability. We discuss why GP transactions have evolved, why some firms seek outside capital, and the practical differences between investing as a GP versus an LP. We also touch on evaluating leadership succession, LP base diversification, liquidity considerations, and why sports franchises continue to attract investor interest. Highlights:

• How GP interest transactions have changed over the past decade.
• Why private-market firms seek external capital to support growth.
• Key differences in evaluating a GP interest versus an LP fund commitment.
• What CAZ looks for in partnership stability and leadership succession.
• How LP base diversification factors into long-term durability.
• Liquidity considerations and how secondary/tender processes work.
• Why sports franchises attract investor attention and how league structures differ.

Guest Bio:

Mark Wade is a Partner at CAZ Investments, where he leads investment strategy and firm initiatives. Since joining CAZ in 2013, Mark has helped the firm expand its presence across asset classes, with a particular focus on GP stakes, energy, and professional sports. Prior to CAZ, Mark earned his MBA from the University of Chicago Booth School of Business. CAZ is known for its alignment-first model—deploying more than $700 million of insider capital alongside its LPs across a range of alternative investments.

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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X / Twitter: David Weisburd: @dweisburd

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Mark Wade: https://www.linkedin.com/in/mark-wade-caia-334b951b/

Links CAZ Investments: https://cazinvestments.com/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.c (0:00) Introduction (0:14) Mark Wade's background and focus on private markets (2:14) Structuring and capital needs in GP stakes investments (7:15) Key considerations and differences in GP stakes vs LP investments (11:24) Downside protection and alignment of interests in GP stakes (15:01) Base case expectations and liquidity concerns in GP stakes (19:39) Sports investments discussion and value growth (24:15) Comparing sports investments to Bitcoin and impact of AI (25:07) Future trends and investing focus in sports entertainment (26:08) Closing remarks

Is traditional valuation dead for the biggest winners of the AI era? Or have investors simply been looking in the wrong place? In this episode, I talk with Dan Ives, Managing Director and Global Head of Technology Research at Wedbush Securities, and one of Wall Street’s most followed tech analysts. Dan has covered the software and technology sector for 25 years, becoming known for his bold, high-conviction calls on Tesla, Nvidia, Microsoft, and Palantir long before they became consensus. We break down why Dan calls Tesla the world’s leading “physical AI” company, why he thinks AI is the largest tech transformation in 40–50 years, what investors miss when they rely only on spreadsheets, and how his pattern-recognition framework helps him spot multi-baggers years before the herd. Highlights:

• Why he views Tesla far beyond autos; autonomy, robotics, robo-taxis, and multi-trillion-dollar upside.
• Why he believes AI is a 40–50 year mega-cycle with second- and third-order winners.
• Why do great companies look expensive every year until suddenly they don’t.
• On pattern recognition, global customer conversations, and signals that never show up in models.
• Lessons from 2008, 2022, and sticking with calls through volatility.
• Why Nadella, Musk, Karp, and Lisa Su are misunderstood and mispriced by Wall Street.
• His 1–10 conviction framework and how he sizes up when inflection happens.
• Where he’s looking for the next multi-baggers in the AI supply chain.
• How setbacks early in his career reshaped his investing worldview.
• His role as Chairman of ORBS (EightCo Holdings) and Worldcoin-aligned authentication.
• Why he partnered with Snow Milk on a fashion collaboration and how “owning who you are” fuels differentiation.

Guest Bio:

Daniel Ives is the Managing Director and Global Head of Technology Research at Wedbush Securities, where he has been a senior equity research analyst covering the technology sector since 2018. Dan has spent 25 years on Wall Street following software, cloud, cybersecurity, mobile, and the broader enterprise tech ecosystem.

He is also the Chairman of EightCo Holdings (ORBS), focused on authentication and digital identity infrastructure aligned with the emerging AI era.

Dan is one of the most sought-after tech experts globally, regularly appearing on CNBC, Bloomberg, BBC, Fox Business, ABC, NBC, Sky News, France 24, NPR, and many other global outlets. He is frequently cited in The Wall Street Journal, The New York Times, Financial Times, Barron’s, Time, The Telegraph, and other major publications.

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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X / Twitter: David Weisburd: @dweisburd

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Daniel Ives: https://www.linkedin.com/in/daniel-ives-542321a8/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com. (0:00) Preview (1:17) Dan Ives on the AI revolution, Tesla's market dominance, and valuation methodology (5:10) The importance of long-term vision and global insights in tech investing (10:52) The role of retail investors and the impact of market sentiment (14:25) The significance of true believers and early adopters in investments (16:13) Recognizing when an investment thesis is wrong and adjusting strategies (22:32) Investment sizing, portfolio construction, and utilizing customer feedback (26:16) Psychological biases and their effects on investor confidence (27:06) Leveraging social media and conferences for investment insights (28:31) Understanding power law returns and second/third order effects in the market (32:20) Evaluating investment success: hit rates and the role of outliers (34:09) Influencing stock narratives and decisions at the board level (37:21) Identifying mispriced founder-led companies and embracing failures (43:41) Dan Ives' personal background and approach to maintaining conviction (47:48) Future projects at Wedbush and personal ventures (49:19) Closing remarks

Is private equity still worth it — or has the industry scaled its way into mediocre returns? In this episode, I talk with Nolan Bean, CFA, CAIA, Chief Investment Officer and Head of Portfolio Management at FEG Investment Advisors, an independent, employee-owned firm advising on $90+ billion in assets for endowments, foundations, healthcare systems, and mission-driven institutions. We dig into the state of OCIOs, interval funds, private equity, and why Nolan believes the lower middle-market still offers the clearest path to real alpha. Nolan also breaks down the coming wave of 401(k) access to private markets, why large-cap buyout is structurally challenged, and how FEG uses a “crisis playbook” to lean into markets without pretending to time them perfectly. Highlights:

• How FEG advises on $90B+ across 300+ clients, mostly nonprofits.
• OCIO incentives, risk-taking, and why some firms drift toward being too conservative.
• Interval funds: easy access, hidden liquidity risks, and “Hotel California” redemptions.
• Why large buyout PE faces pressure from high entry multiples, rates, and too much capital.
• Why lower middle-market buyout still works: founder-led deals, ops value-add, less leverage.
• Main risks in small companies: fragility, client concentration, and key-person exposure.
• Factor models vs. real alpha: where Fama-French stops explaining PE returns.
• Shrinking small-cap universe and why public markets may have adverse selection.
• The coming 401(k) and retail flow into alternatives — and shrinking illiquidity premia.
• FEG’s VFS (valuation, fundamentals, sentiment) crisis framework for drawdowns.
• Four key risks: goal risk, market risk, illiquidity risk, and maverick risk.
• Nolan’s top two lessons: don’t fight the Fed, and relationships compound.

Guest Bio:

Nolan Bean is the Chief Investment Officer and Head of Portfolio Management at FEG Investment Advisors, where he has worked since 2004. He leads portfolio construction, research oversight, and investment strategy across FEG’s OCIO and advisory clients. Nolan is both a CFA and CAIA charterholder. He holds a finance and quantitative analysis degree and an MBA from the University of Cincinnati.

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/ Nolan Bean: https://www.linkedin.com/in/nolanbean/

Links FEG Investment Advisors: https://www.feg.com/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com. (0:00) Introduction (0:28) Growth catalysts and criteria for RIAs and investment advisors (2:13) Criticisms of OCIOs and conservative risk-taking (3:59) Discussion on interval funds and private equity buyouts in 2025 (7:39) Challenges in large buyout funds and lower middle market opportunities (16:23) Risks and benchmarking in lower middle market investments (21:45) Democratization of private markets and 401(k) investments (24:36) Illiquidity premium and institutional investors' response (27:06) Identifying opportunities in out-of-favor sectors and portfolio construction (31:07) Managing risk tolerance and market downturn strategies (34:24) Behavioral finance and liquidity in portfolio management (37:18) Evaluating hedge funds and strategies for market downturns (41:21) Diversification benefits and long-term market trends (44:03) Public policy influence on markets and timeless investment advice (47:55) Interest rates' impact on asset prices and politicians' market influence (53:14) Investing during crises and the importance of relationships (56:18) Venture capitalists, reciprocity, and value in relationships (58:22) Closing remarks

How do you build a multibillion-dollar company from scratch, walk away at the peak, and reinvent your life around purpose, generosity, and impact? In this episode, I talk with Pete Kadens, one of America’s most respected first-generation wealth creators and one of the leading philanthropists focused on closing education and opportunity gaps across the U.S. Today. Pete and I dive into how he built Green Thumb Industries (GTI) into a multibillion-dollar cannabis company, the unsexy strategies that made it work, and why choosing overlooked markets and consumers unlocked massive profit. We cover the power of ownership cultures, transparency, discipline frameworks, and why giving equity and education to employees creates extraordinary performance. We also explore the character transformation that led him to retire at 40. Highlights:

• The unsexy strategy behind scaling GTI into a multibillion-dollar operator
• Why Pete targeted the 30–50-year-old female consumer long before the market noticed
• How choosing Toledo instead of Chicago and Erie instead of Philadelphia created monopolistic advantages
• The power of ownership cultures, ESOP-style alignment, and financial transparency
• Why employees perform better when they are treated like owners
• Pete’s shift from business success to a life of impact and philanthropy
• The emotional toll, guilt, and clarity that led him to retire at 40
• How he rebuilt his parenting philosophy: presence, character, and modeling discipline
• Why “how you do anything is how you do everything” became his family standard
• The timeless rule he lives by: the gap between “I should” and “I did”

Guest Bio:

Pete Kadens is a serial entrepreneur and dedicated philanthropist who currently serves as Chairman of The Kadens Family Foundation, a national charitable organization focused on closing education and wealth gaps. He is also the Founder and Co-Chairman of Hope Chicago, which is educating tens of thousands of underserved Chicagoans, and a key supporter of Hope Toledo, now serving more than 300 families with tuition-free college and trade-school pathways.

Pete is the Founder & Chairman of Warmer, a new social platform designed to create kind, supportive, and non-toxic peer-to-peer interaction. He also serves as Chairman Emeritus of StreetWise, one of Chicago’s largest homeless assistance organizations, and sits on multiple nonprofit and for-profit boards dedicated to social impact.

Pete is a 2019 Henry Crown Fellow at the Aspen Institute, one of the most selective fellowship programs in the world, recognizing leaders who create ventures solving society’s most challenging problems.

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/ Pete Kadens: https://www.linkedin.com/in/petekadens/

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

(0:00) Introduction (0:19) Founding Green Thumb Industries and seizing opportunities in the cannabis industry (2:08) Focusing on profit and choosing unsexy locations (4:05) Targeting non-obvious customer segments and building partnerships (7:44) Creating a disciplined framework for employee autonomy and engagement (13:06) The importance and advantages of an employee ownership culture (18:54) Transitioning from business to philanthropy (19:47) Exploring different forms of wealth and personal fulfillment (24:11) Balancing business success with personal life and trade-offs (30:30) Role modeling, parenting philosophies, and teaching kindness (37:40) Pursuing excellence, discipline, and lessons from Aspen Institute fellows (41:41) Importance of suspending assumptions and embracing rest (43:37) Valuing idiosyncratic excellence and embracing neurodivergence (46:28) Turning aspirations into achievements and celebrating progress (49:09) Concept of the minimum lovable product and reflecting on success (50:44) Closing thoughts, gratitude, and how to follow Pete Kadens (51:14) Closing remarks

What separates elite CIOs from everyone else? In this solo-style deep-dive conversation, I sit down with Alan McKnight, Executive Vice President and Chief Investment Officer at Regions Asset Management, to unpack how one of the industry's most respected allocators makes decisions across public and private markets. Alan oversees investment strategy, risk management, and portfolio construction across the firm's full platform — and brings decades of experience from leadership roles at Truist, SunTrust, Equitable, and Morgan Stanley. We get into the realities of managing capital across different client types, how CIOs should think about illiquidity versus opportunity, where structural alpha truly comes from, and the process-driven framework Alan uses to separate skill from luck. If you're an allocator, founder, CIO, or LP, this episode lays out one of the cleanest mental models you'll hear on building durable long-term returns. Highlights:

• Why liquidity is the most misunderstood variable in portfolio construction
• How allocators overestimate what they actually need.
• The barbell playbook Alan uses to balance “hyper-liquid” and “hyper-private” exposures across client types.
• How to generate structural alpha by lowering fees and accessing co-investments without adding unnecessary risk.
• Why outcome-based thinking destroys CIO performance
• How process accountability creates compounding advantages.
• How to re-underwrite every position with brutal honesty, even when the mark looks terrible in the short term.
• The alignment problem: why CIO tenures don’t match fund cycles and what it means for long-term returns.
• The traits that separate world-class allocators from good ones
• Why the unsexy work often creates the most alpha.
• Alan’s advice to his younger self and the career decisions that would have accelerated his trajectory even further.

Guest Bio:

S. Alan McKnight, Jr., CFA is the Executive Vice President and Chief Investment Officer of Regions Asset Management, responsible for overall investment strategy, portfolio and risk management, and portfolio construction across $70BN in assets under management and $150BN in assets under advisement.

He is Chairman of the firm’s Investment Working Group and serves on the Asset Liability Committee, regularly representing Regions as its chief spokesperson on markets with outlets including CNBC, Bloomberg, FOX Business, The Wall Street Journal, The New York Times, and CNN Money. Before joining Regions in 2015, Alan served as Head of Institutional Investments for Truist, Chief Investment Officer for SunTrust Institutional Investment Advisors, and held portfolio management roles at Equitable Asset Management and Morgan Stanley Asset Management.

He holds a B.A. in Economics from Washington and Lee University, an MBA from the University of Texas at Austin, and the Chartered Financial Analyst designation. Alan has served on boards including the Alliance Theatre, Cherokee Garden Library, The New Normal Society, and the Woodruff Arts Center Investment Committee.

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 #startupsuccess #openlp #assetmanagement

Stay Connected:

X / Twitter: David Weisburd: @dweisburd

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Alan McKnight: https://www.linkedin.com/in/s-alan-mcknight-jr-cfa-2b69993/

Links Regions Bank: https://www.regions.com/personal-banking

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com. (0:00) Introduction (1:05) Assessing illiquidity: willingness, capacity, and psychological aspects (3:28) Private investment access for smaller investors and alternatives market (6:42) Challenges for small and mid-sized managers in alternatives (8:07) Interval funds: characteristics and practicality (11:06) Liquidity needs and planning across market environments (18:07) Alpha generation, manager selection, and behavioral economics (22:45) Neurobiological and human bias in trading decisions (25:48) Illiquidity benefits and structural alpha in private markets (31:48) Liquidity management strategies and accountability in investing (37:19) Team dynamics and incentive alignment in institutional investing (42:00) Attracting and educating top investment talent (45:03) Leveraging AI in investment research (48:09) Evaluating and interacting with new managers (51:22) Trust and reunderwriting in investment relationships (54:10) Reflective advice and value in foundational tasks (56:21) Closing remarks

What happens when you’re forced to face your biggest fear? In this solo episode, David Weisburd shares a deeply personal reflection on how moments of crisis can become the crucible that forges strength, resilience, and clarity. Drawing inspiration from Lloyd Blankfein’s reflections on the 2008 financial crisis, David explores why confronting your greatest fears—rather than avoiding them—can transform you into a more powerful, anti-fragile version of yourself. From Joe Rogan’s public reckoning to founders who rebuilt stronger after near-death moments, this episode unpacks the paradox of hardship: how the moments that almost break you often become the foundation for your greatest breakthroughs. Highlights:

• Why your greatest fear may hold the key to your personal and professional growth
• What Lloyd Blankfein learned from leading Goldman Sachs through the 2008 crisis
• How Joe Rogan turned public backlash into renewed influence and clarity
• Why “manufacturing crisis” might reveal what truly limits you
• How top founders come back stronger from near-death experiences
• The mindset shift that turns fear into fuel for anti-fragility and leadership growth

Host Bio:

David Weisburd is the founder of Weisburd Capital and the host of the How I Invest podcast. Previously, Mr. Weisburd was a Partner and Head of Venture Capital at 10X Capital, where he led notable firm investments into Robinhood, Honeybook, Palantir, and DraftKings. Mr. Weisburd founded Growth Technology Partners, a solo-GP venture firm, which was acquired by 10X Capital.

Prior to his venture capital career, Mr. Weisburd was on the founding teams of two venture-backed technology startups, iSocket (acquired by Rubicon Project (NYSE: RUBI)) and RoomHunt (acquired by RentLingo).

Mr. Weisburd served as a member of the board of directors of 3 publicly-traded companies.

Mr. Weisburd received an MBA from Dartmouth’s Tuck School of Business, and a master’s in psychology from Harvard University.

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:@dweisburd LinkedIn:https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.linkedin.com/company/weisburd-capital How I Invest: https://howiinvestpodcast.com/episodes

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com. (0:00) Introduction (0:30) Reflection on Lloyd Blankfein's career, antifragility, and confronting challenges (2:42) Closing remarks

Can a 23-year-old Harvard dropout build the next billion-dollar company? In this episode, I talk with Steven Wang, founder and CEO of dub, a U.S. copy-trading platform that lets you automatically mirror the portfolios of real investors and traders. We get into why he thinks most retail investors won’t get good at stock picking, why the future is about picking people, not tickers, and how dub is trying to turn social-media-driven, mimetic trading into better financial outcomes. We also cover the retail trading boom, meme stocks, the “retail army,” what dub’s top creators actually do to generate alpha, and how a creator-led marketplace for strategies could reshape how the next generation builds wealth. Highlights:

• Why dub is America’s first regulated copy-trading platform and how it works
• The retail trading boom: meme stocks, FOMO, and 20–35% of daily volume coming from retail
• How Gen Z thinks about wealth, risk, and becoming a millionaire through investing
• What dub’s top creators actually do to generate alpha (micro-caps, swing trading, social influence)
• How momentum trading can become real value (GameStop, Opendoor, AMC)
• Steven’s founder journey: VR startup at 16, Harvard dropout, and raising $47M
• Leadership lessons: moving from micromanagement to mission-driven culture
• The Sisyphus mindset, meditation, and staying grounded during low moments
• What Steven would tell his 2021 self about reinvention, feedback, and patience

Guest Bio:

Steven Wang is the founder and CEO of dub, a regulated U.S. copy-trading platform that lets investors follow and automatically mirror the portfolios of real investors and creators. Dub is owned and operated by DASTA Inc., with advisory services provided by dub Advisors, LLC, an SEC-registered investment adviser, and brokerage services provided to retail customers by DASTA Financial, LLC, an SEC-registered broker-dealer and FINRA/SIPC member, with clearing through APEX Clearing Corporation.

Dub has raised $47 million in total funding, including a $30 million Series A, and offers access to 200+ crowdsourced Creators with real, transparent track records that users can copy starting from small account sizes. Before founding dub, Steven built and sold a VR startup he began as a teenager, worked briefly at Apple, and attended Harvard before leaving to focus on dub full-time.

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/ Steven Wang: https://www.linkedin.com/in/swangentr/

Links Dub: https://www.dubapp.com/

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

(0:00) Introduction (0:14) Retail investors' underperformance and the thesis behind Dub (0:32) Historical context and explosion of retail trading (1:19) Cultural zeitgeist, social media, and trading during COVID-19 (3:12) Dub's mission post-2022 crash and entrepreneurial journey (5:15) Startups: Timing, market conditions, and young entrepreneurship challenges (7:23) Scaling the business, culture, and hiring practices (12:11) Anti-selling in interviews and wealth transfer to younger generations (14:32) Simplifying investing and the importance of trust in decisions (17:09) Broadening participation in wealth creation and investing habits (19:20) Operationalizing trends and building a marketplace of strategies (23:33) Impact of meme stocks and retail investor strategies (27:11) Legal strategies behind traders' success and building a strong network (35:50) Mindfulness, advice for entrepreneurs, and decision-making (38:23) Balancing ambition, patience, and clarity of vision in startups (41:00) Leadership strategies and the power of compounding efforts (41:28) Closing remarks

How do you turn whiskey barrels into an institutional asset class? In this episode, I sit down with Giuseppe Infusino, Chief Investment Officer and Managing Partner at InvestBev Group, to explore how a real asset like aged whiskey is quietly becoming one of the most uncorrelated and profitable investments in alternative markets. From his early years at RVK advising multi-billion-dollar allocators to managing institutional portfolios in a niche category few understand, Giuseppe shares how InvestBev has built an entirely new asset class from the ground up. We discuss the economics of whiskey aging, how barrel pricing creates asymmetric returns, and why alcohol performs differently across economic cycles. This conversation breaks down incentives, alpha generation, and how to educate LPs on emerging strategies long before they go mainstream. Highlights:

• The incentives that keep consultants from finding the “best and brightest” managers—and how RVK broke the mold
• Why 90% of RVK’s fund allocations were self-sourced, and how that approach drives better returns
• The conversation that led Giuseppe to co-found InvestBev—and how whiskey became a new institutional asset class
• The real asset characteristics of whiskey barrels—and why they appreciate over time like fine art
• How InvestBev’s analysis with Kellogg proved near-zero correlation between whiskey and traditional markets
• Why barrel investments deliver equity-like returns with half the volatility of equities
• How to educate LPs when creating a new asset class—and what early adopters get right
• Why InvestBev’s edge comes from deep beverage-industry relationships across Bacardi, Molson, and Coors
• The scaling lessons from Fund I to Fund V—and how institutional credibility compounds over vintages
• Why operational excellence, data, and early hiring decisions define fund longevity
• The best LP advice he ever received: “No investor ever complains about getting their money back.”

Guest Bio:

Giuseppe Infusino is the Chief Investment Officer and Managing Partner at InvestBev, where he leads the firm’s investment strategy, sourcing, diligence, and structuring processes across consumer brands, beverage services, and hard assets.

Prior to InvestBev, he spent over a decade managing institutional investment portfolios for prominent allocators deploying multiple billions in private markets. He holds an MBA in Marketing & Entrepreneurship from the Kellogg School of Management, Northwestern University, and a B.S. in Finance & Real Estate from the University of Wisconsin-Madison.

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/ Giuseppe Infusino: https://www.linkedin.com/in/giuseppe-infusino-331b198/

Links InvestBev: https://www.linkedin.com/company/investbev/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com. (0:00) Introduction (1:30) Incentive structures in consulting and investment staff (3:20) Consultants and emerging managers (4:55) Sourcing and transitioning to bourbon investments (7:54) Market dynamics and correlation of bourbon investments (10:27) Asset allocation in bourbon investing (12:05) Educating LPs on bourbon investments (14:15) First mover challenges in new asset classes (16:21) Organizational influence on investment decisions (17:14) Economics of alcohol production (19:07) The three-tiered system in the alcohol industry (19:30) Lessons from starting and scaling a fund manager (21:11) Growth rates and transitioning to private credit (25:43) Operational investments and valuation models (28:27) Best LP advice and perspectives on capital return (31:01) Utilization of AI in investment strategies (33:14) Closing remarks

What separates great investors from generational ones—and how do you actually find the next Elon Musk? In this episode, I sit down with Mike Annunziata, Founder & Managing Partner of Also Capital, a solo GP fund backing the world’s most ambitious hard tech founders. Before launching Also Capital, Mike spent years at the Cornell University Endowment, helping allocate over $1 billion across venture and private equity managers—giving him a front-row seat to what “world-class” really looks like. We talk about how LPs identify the next top-decile fund managers, why the best founders are like amateur pilots, and how to find the tiny behavioral tells that separate the merely ambitious from the truly elite. From identifying credibility under pressure to understanding the physics of hard tech investing, Mike shares a rare, insider’s look at the art of backing outliers. Highlights:

• How working at the Cornell Endowment shaped Mike’s investor mindset and revealed what “world-class” really looks like
• The difference between top-quartile and top-decile managers—and why early risk-taking defines greatness
• Why founders who combine ambition with credibility are the ones who build generational companies
• What venture investors can learn from Bain Capital Life Sciences and the power of early conviction
• The “amateur pilot” framework: how to identify founders who take disciplined risks under pressure
• Why great founders are magnets for talent—and how followership predicts success more than ideas
• The difference between competitiveness, urgency, and toxic culture in startups
• How AI is transforming hard tech—from edge computing to design cycles
• What it takes to spot a breakout hard tech company before anyone else does
• Why discipline—not deal-chasing—is the real driver of long-term venture success

Guest Bio:

Mike Annunziata is Managing Partner at Also Capital, where he invests in and supports hard-tech companies solving atomic scale problems—across aerospace, defense, robotics, advanced manufacturing, communications, mobility, and applied AI. Since 2019 he’s seeded companies now valued at over $2 billion including Radiant, Varda Space, K2 Space, and Northwood, which have collectively raised over $500 million.

Previously, Mike was Co-Founder & CEO of Farther Farms, a Series B startup out of Cornell University, and spent three years as Senior Investment Analyst at Cornell University’s Investment Office, allocating capital across venture and private funds. He holds a B.S. in Industrial & Labor Relations and an MBA from Cornell University’s Johnson Graduate School of Management.

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.

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X / Twitter: David Weisburd: @dweisburd

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Mike Annunziata: https://www.linkedin.com/in/mike-annunziata-12853bb/

Links Also Capital: https://www.alsocapital.com

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com. (0:00) Introduction (0:24) Understanding investment talent and managing risk (0:54) Identifying world-class funds and great managers (2:03) Example of early successful fund: Bain Capital Life Sciences (3:26) Building a brand and competitive advantage in investing (5:00) Traits of successful founders and top decile managers (8:02) Investment edge and volatility in venture strategies (12:27) Focus and diversification of Also Capital investments (16:54) Nonconsensus views and breaking down ambitious projects (19:04) High IQ and EQ in founders and early leadership signs (24:08) Competitiveness, sense of urgency, and mission-driven motivation (31:08) Impact of AI on hard tech startups and identifying big founders (36:08) Attracting top talent and advising young founders (41:10) Dynamics of high RPM vs. high gear in startups (44:20) Timeless advice and understanding pitfalls for new VCs (46:29) Balancing deal volume with founder quality and knowing your founders (52:19) Closing remarks

How do you turn purpose, legacy, and innovation into a single investing philosophy? In this episode, I speak with Sara Crown Star, Venture Partner at FemHealth Ventures and President of SCS Innovations. Sara shares how her experience growing up in one of America’s most prominent families shaped her values as an investor and why she believes the next trillion-dollar opportunity lies in women’s health. We discuss the evolution of FemHealth Ventures’ investment thesis, the creation of the “FemHealth Framework,” and how it’s redefining what women’s health means across drugs, devices, diagnostics, and AI-driven solutions. Sara also shares personal stories from her family’s legacy—how values like integrity, community, and purpose continue to drive generational success. Highlights:

• How FemHealth Ventures is redefining women’s health through the “FemHealth Framework”
• How AI and data analytics are transforming fertility outcomes through Cercle, backed by Sheryl Sandberg
• Why innovation in postpartum depression could save lives—and how Reunion Neuroscience is pioneering new treatment paths
• The overlooked investment opportunity in women’s health—and how half the population remains underrepresented in clinical trials until 1993
• What the Crown family’s story teaches about values, reputation, and resilience across generations
• The founding lessons of Henry Crown during the Great Depression—and why character still compounds
• How the Henry Crown Fellows Program at the Aspen Institute turns success into significance
• Why purpose and meaning unlock the “sixth gear” for investors and founders
• Advice for future generations: raising independent thinkers, building genuine friendships, and preserving family values

Guest Bio:

Sara Crown Star is a Venture Partner with FemHealth Ventures, a top-decile VC firm with $100 million in AUM, focused on advancing innovations in women’s health. FemHealth Ventures invests in companies developing drugs, devices, diagnostics, and digital/AI-enabled solutions. Sara is also president of SCS Innovations, which connects entrepreneurs with capital to bring new technologies to market. She serves on the board of 1871 (Chicago’s entrepreneurial hub), is a life trustee of the Erikson Institute, and is President of the Colonel Henry Crown Scholarship Fund. She is also a director of Musicians on Call, the Jewish United Fund of Chicago, the Ortus Foundation, and the Crown Family Foundation. Sara graduated with a B.S. from the University of North Carolina at Chapel Hill and a J.D. from Georgetown University Law Center. She also completed the Wexner Heritage Program and received an Executive M.B.A. from Northwestern’s Kellogg School of Management.

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.

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X / Twitter: David Weisburd: @dweisburd

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Sara Crown Star: https://www.linkedin.com/in/saracrownstar/

Links FemHealth Ventures: https://www.femhealthventures.com/

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

(0:00) Introduction (1:18) Sara's passion for women's health and career beginnings (2:34) Investment highlights: Gynesonics and Reunion Neuroscience (7:28) Women's exclusion in clinical trials and market potential (9:13) Future trends and family values in women's health investing (14:08) Community impact and the role of purpose in success (22:23) Challenges of prominence and wealth management in the Crown family (25:23) Closing remarks

Why are we wired to chase quick wins instead of lasting breakthroughs—and how can investors reprogram that bias? In this third solo episode, David Weisburd unpacks the neuroscience of decision-making and how understanding dopamine can dramatically change the way you operate as an investor, founder, or builder. Drawing on insights from his conversation with Dave Fontenot of HF0, David explains why long-term rewards (“slow dopamine”) create compounding advantages while short-term hits (“fast dopamine”) destroy focus. He shares tactical strategies for building “monk mode” systems that protect deep work, how to avoid the illusion of productivity, and why the most valuable ideas require discomfort and delay before payoff. This episode is about rewiring your brain for compounding—not con Highlights:

• How fast dopamine (short-term gratification) undermines long-term focus
• Why slow dopamine is the neurological key to compounding performance
• How to structure your day for deep work and “monk mode” productivity
• Why checking emails or chasing small wins creates addictive behavior loops
• How to identify the most important, non-urgent tasks that create 10x leverage
• Why most founders confuse activity with progress—and how to fix it
• The mental models behind HF0’s ability to 20x ARR in just 12 weeks
• How to replace short-term dopamine hits with long-term focus triggers
• What Ryan Hoover’s automation philosophy teaches about time leverage
• How to act “slow” in a world addicted to fast—and win over decades

Host Bio:

David Weisburd is the founder of Weisburd Capital and the host of the How I Invest podcast. Previously, Mr. Weisburd was a Partner and Head of Venture Capital at 10X Capital, where he led notable firm investments into Robinhood, Honeybook, Palantir, and DraftKings. Mr. Weisburd founded Growth Technology Partners, a solo-GP venture firm, which was acquired by 10X Capital.

Prior to his venture capital career, Mr. Weisburd was on the founding teams of two venture-backed technology startups, iSocket (acquired by Rubicon Project (NYSE: RUBI)) and RoomHunt (acquired by RentLingo).

Mr. Weisburd served as a member of the board of directors of 3 publicly-traded companies.

Mr. Weisburd received an MBA from Dartmouth’s Tuck School of Business, and a master’s in psychology from Harvard University.

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:@dweisburd LinkedIn:https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.linkedin.com/company/weisburd-capital How I Invest: https://howiinvestpodcast.com/episodes

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com. (0:00) Introduction (3:50) Aligning business goals with slow dopamine and differentiating career paths (4:59) Ryan Hoover's approach to problem-solving and long-term efficiency (6:53) Dramatic upside of slow thinking and human evolution (7:08) Closing remarks

How do you democratize access to private markets and what happens when everyone can invest like a VC? In this episode, I sit down with Kendrick Nguyen, Co-Founder and CEO of Republic, the global platform that’s opened up private investing to over 3 million people across 150 countries, facilitating more than $2.6+ billion in transactions. We unpack how tokenization, fractionalization, and regulatory innovation are reshaping private markets. Kendrick explains how Republic is bridging the gap between institutions and retail investors, what tokenized SpaceX and OpenAI shares mean for the future of liquidity, and why the next evolution of finance is about participation—not speculation. Highlights:

• How tokenization creates a faster, cheaper, cross-border infrastructure for capital markets
• Why retail participation in private markets remains shockingly low—and how Republic is changing that
• How Robinhood’s tokenized SpaceX and OpenAI campaign boosted stock performance and retail awareness
• The $150 trillion opportunity in retail capital waiting to enter private markets
• Inside Republic’s partnership with Hamilton Lane to open institutional funds to everyday investors
• Why tokenization could make private equity more profitable than public equities
• How Republic balances legal engineering, regulation, and innovation to stay ahead in fintech
• The social side of investing: why “return on experience” can be as powerful as ROI
• How fractional ownership can restore optimism and access to the American Dream
• Why fintech founders must partner—not fight—with regulators to scale safely

Guest Bio:

Kendrick Nguyen is the Co-Founder & CEO of Republic, a global platform for investing in private markets. Before launching Republic in 2016, he served as General Counsel at AngelList, leading regulatory affairs and international expansion. He has also co-founded CoinList and held prior roles at The Permal Group and Kanbar Enterprises, and has been a Fellow at Stanford Law School and the Rock Center for Corporate Governance.

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/ Kendrick Nguyen: https://www.linkedin.com/in/kendrick-nguyen-7145bb5/

Links Republic: https://republic.com/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com. (0:00) Introduction (1:45) Retail participation and barriers in private equity (2:51) Access and liquidity issues in private markets (4:25) Social good and gateway products for tokenization (7:25) Robinhood's token giveaway and market impact (11:08) Mirror tokens, regulatory aspects, and partnerships (15:28) Growth in private equity and market disruption comparisons (20:18) Republic's evolution and influencer engagement (26:07) Learning to invest through small investments (31:26) Changing American dream and investment excitement (34:09) Social component and future of crowdfunding (40:52) Legal expertise and regulatory collaboration in fintech (45:44) Launching tokens and long-term investment benefits (50:51) Personal success stories and overcoming obstacles (57:24) Timeless advice and closing remarks (59:39) Closing remarks

Can founders 10x their progress in 12 weeks? In this episode, I speak with Dave Fontenot, Founder of HF0, a groundbreaking startup residency that’s redefining how AI companies are built. HF0’s model—part hacker house, part monastic focus—is based on the idea that startups grow fastest when founders eliminate every distraction and operate in uninterrupted flow. Dave explains how the residency model is helping founders make “two years of progress in 12 weeks,” why the most dangerous distraction is the second most important thing in your business, and how recursive subtraction leads to breakthrough realizations. We discuss what true flow looks like, how competition in AI has changed company-building forever, and why the next generation of founders will work like athletes in training camp. Highlights:

• How HF0 redefined startup acceleration by replacing addition with subtraction
• Why the most insidious distraction for founders is the second most important thing in their business
• How residency-based company building leads to “a year or two of progress in 12 weeks”
• The psychology behind avoidance—and why even elite founders escape the hardest problems
• How AI changes the calculus of startup speed by compressing iteration cycles
• Why “flow compounds” and how context continuity multiplies productivity
• The secret to building software 10x faster: protect the compound return of uninterrupted work
• Why empathy and trust—not specs—create products with soul
• How HF0’s model is spreading globally, spawning a new generation of residencies
• Practical ways to create “HF0 Lite” in your own life—down to ordering routines and workspace design

Guest Bio:

Dave Fontenot is the Founder and CEO of HF0, a residency program designed for exceptional founders building the next generation of AI and software companies. At HF0, he helps entrepreneurs compress years of progress into months by creating an environment of deep focus, trust, and accountability.

Before HF0, Dave co-founded Backend Capital, an early-stage venture fund backing developers and technical founders, and was one of the key builders behind MHacks, one of the largest collegiate hackathons in the United States.

He began his career as a software engineer and community builder, working with some of the world’s most ambitious early-stage founders. Dave’s work sits at the intersection of engineering, psychology, and company building—and he’s become one of the leading voices shaping how high-performing startup teams operate in the AI era.

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/ Dave Fontenot: linkedin.com/in/davefont

Links HF0: https://www.hf0.com/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com. (0:00) Introduction (0:32) Historical examples of residency formats in company building (1:01) Overview of the eleventh batch at HF0 (2:21) The principle of subtraction in HF0 (4:01) Role of AI in increasing the rate of realizations (5:21) Practical examples of subtraction in maintaining flow state (7:06) Focusing on the most important business lever (9:01) Success stories and collaboration with investors at HF Zero (12:37) Psychological aspects of task avoidance (17:26) Adaptability of AI-driven startups (18:50) Infinite potential for AI innovation (20:27) The compound return of flow state on productivity (24:02) Flow state comparison to jazz and surfing (27:21) Continuous context in software development (29:07) Identifying valuable AI products (31:09) Building trust and empathy with AI tool users (31:48) Implementing HF0 principles in daily life (34:07) The rise of residencies in early-stage venture (36:03) Auditing interruptions to maintain flow (38:49) Focusing on high-impact tasks (40:13) Competitive nature of AI and residency programs (41:40) Superior company building through residencies (42:43) Practical steps for focus and productivity (43:51) CEO's role in problem-solving (44:21) Closing remarks

How do you train the next generation of allocators—and what separates elite investment offices from the rest? In this episode, I speak with Alex Ambroz, Founder and CEO of the Allocator Training Institute, whose mission is to professionalize allocator education. Alex has spent his career building and leading investment teams across Morgan Creek, J.P. Morgan, Cleveland Clinic, Aberdeen, and now as the founder of Allocator Training Institute. We dive into the evolution of the endowment model, how allocators detect hidden risk, the difference between true alpha and disguised beta, and why collaboration—not competition—is the secret to better portfolio outcomes. Alex also explains how today’s top allocators use data, relationships, and operational excellence to stay ahead of market shifts. Highlights:

• How Morgan Creek brought the endowment model to the broader OCIO world and scaled to $10 billion AUM
• Why early adopters of new strategies share the same psychographic traits as elite innovators
• How allocators spot “fake alpha” hidden behind high beta exposure and factor drift
• Why most allocators still don’t go beyond CAPM beta—and how that hides systemic risks
• How the best teams operationalize everything so analysts can focus purely on analysis
• Why top allocators collaborate instead of compete—and how peer groups share best practices
• How to build trust through transparency, discretion, and consistency across relationships
• What allocators really look for in on-site due diligence—down to the parking lot test
• How great GPs educate allocators by simplifying complexity without dumbing it down
• Why asking the right questions is a bigger edge than having all the answers

Guest Bio:

Alex Ambroz is the Founder and CEO of the Allocator Training Institute, the first structured education platform dedicated to developing the next generation of institutional allocators.

Before founding ATI, Alex spent two decades in senior investment roles at Morgan Creek Capital, J.P. Morgan, Cleveland Clinic, and Aberdeen Standard Investments, where he built and managed multi-asset portfolios across public and private markets. He has trained hundreds of analysts and investment officers globally and holds deep expertise in portfolio construction, factor modeling, and operational due diligence.

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/ Alex Ambroz: https://www.linkedin.com/in/alexambroz/

Links Allocator Training Institute: https://allocatortraining.com/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com. (0:00) Preview (0:48) Alex Ambroz's career journey and experience at Morgan Creek (3:16) Endowment model, early adopters, and identifying alpha versus beta (10:30) Fama-French model, factor analysis, and characteristics of forward-thinking LPs (17:50) Collaboration among top allocators and the non-zero-sum nature of asset allocation (25:05) Andy Golden's perspective on allocator influence and fund evaluation (28:10) Operationalizing new asset classes and the importance of asking the right questions (34:02) On-site visits versus Zoom meetings and red flags in operational due diligence (41:47) Effective communication between GPs and LPs and the Allocator Training Institute (49:09) Target audience for Allocator Training Institute and revisiting the infinite game of investing (53:32) Closing remarks

What separates the good investors from the great ones? In this 2nd solo episode, David Weisburd shares the three rules that every world-class investor follows—rules that have nothing to do with IQ, luck, or access, and everything to do with how they think, use time, and define their game. Drawing on hundreds of private conversations with elite fund managers, David breaks down why consistency is overrated, how to buy back your time, and why clarity about your “game” might be the biggest competitive edge of all. If you’re an investor, founder, or builder looking to sharpen your mental model, this episode offers a rare inside look at the mindset of the best in the business. Highlights:

• Why the best investors don’t care about being consistent—they care about results
• How cognitive dissonance becomes a superpower in a world that changes daily
• Why responding to every email is a lie—and what true time management looks like
• How guarding your time like a hawk directly increases business revenue
• Why great investors define their “buy box” with boring specificity—and win because of it
• How clarity about your game protects your time and attracts the right deals
• What top investors do differently when it comes to decision filters and opportunity flow

Host Bio:

David Weisburd is the founder of Weisburd Capital and the host of the How I Invest podcast. Previously, Mr. Weisburd was a Partner and Head of Venture Capital at 10X Capital, where he led notable firm investments into Robinhood, Honeybook, Palantir, and DraftKings. Mr. Weisburd founded Growth Technology Partners, a solo-GP venture firm, which was acquired by 10X Capital.

Prior to his venture capital career, Mr. Weisburd was on the founding teams of two venture-backed technology startups, iSocket (acquired by Rubicon Project (NYSE: RUBI)) and RoomHunt (acquired by RentLingo).

Mr. Weisburd served as a member of the board of directors of 3 publicly-traded companies.

Mr. Weisburd received an MBA from Dartmouth’s Tuck School of Business, and a master’s in psychology from Harvard University.

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:@dweisburd LinkedIn:https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.linkedin.com/company/weisburd-capital How I Invest: https://howiinvestpodcast.com/episodes

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com. (0:00) Introduction (0:19) Cognitive dissonance and guarding time in top investors (1:39) Specificity and clear investment criteria (2:09) Closing remarks

What happens when an investor treats crypto like software infrastructure, not speculation? In this episode, I sit down with Avichal Garg, Co-Founder and Managing Partner of Electric Capital, to unpack the evolution of crypto investing—from speculative hype cycles to infrastructure that powers the next era of the internet. Avichal explains how Electric Capital measures developer activity across blockchain ecosystems, why he believes the next trillion-dollar opportunities are being built quietly by open-source engineers, and how software-based incentives will transform everything from finance to governance. We discuss the reality of investing through crypto winters, the rise of modular blockchains, the lessons learned from building at Google and Facebook, and how AI and decentralization are beginning to converge. Highlights:

• How Electric Capital built the most comprehensive developer data set in crypto
• Why tracking engineers is a better signal than token price or TVL
• How Avichal differentiates between speculation and true infrastructure investment
• Why open-source software is the backbone of the next financial system
• How Electric measures developer retention and ecosystem health across chains
• Why crypto winters are the best time to back new protocols and founders
• How decentralization and AI will intersect to create new governance models
• Why the future of crypto is about composability, not maximalism
• How venture capital must evolve to serve protocol-based companies
• Why patience and conviction separate enduring investors from trend followers

Guest Bio:

Avichal Garg is the Co-Founder and Managing Partner of Electric Capital, a venture firm investing in builders of decentralized networks, infrastructure, and developer tools.

Before launching Electric Capital, Avichal founded Spool (acquired by Meta) and previously held senior roles at Google and Facebook, where he helped scale some of the most widely used consumer products on the internet.

He is recognized for pioneering a data-driven approach to crypto investing—using developer activity, GitHub commits, and open-source metrics to identify early momentum in blockchain ecosystems.

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/ Avichal Garg: https://www.linkedin.com/in/avichalgarg/

Links Electric Capital: https://www.electriccapital.com/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com. (0:00) Preview (1:26) Introduction with guest Avichal Garg (1:30) Electric Capital's inception and trust in investing (6:01) Long-term trust, integrity, and alignment in partnerships (10:00) Future opportunities for new General Partners (13:43) Electric Capital's investment thesis and engineer necessity (19:10) Disruption of TradFi by crypto and regulatory moats (23:32) Coinbase's potential and crypto prediction markets (29:42) Crypto's integration and stablecoins' market dynamics by 2030 (35:11) Bitcoin valuation and dollar depreciation (39:09) Asset allocation in high growth tech and inflation strategies (44:46) Lived experience vs. CPI, economic and tax policy impacts (50:07) Middle class plight and social contract solutions (52:52) Policy, AI, and robotics in shaping the future (54:06) SEC regulations and digital assets (56:04) Investing advice: patience and resource management (58:55) Market participation and timing strategies (1:02:12) AI's limitless potential and US economic leadership (1:03:09) Closing remarks

How do you build trust in an industry that’s built on auctions and price maximization? In this episode, I speak with Melvin Hibberd, Chief Investment Officer of Hunter Point Capital, about how the firm is redefining GP stakes investing through proprietary partnerships, structural creativity, and long-term alignment. Melvin takes us inside the evolution of GP stakes—from his pioneering work at Blackstone Strategic Partners to launching Hunter Point—and shares how he avoids auction dynamics that distort relationships, what truly drives alignment between investors and GPs, and why patience, not speed, builds lasting value. We cover everything from bespoke deal structuring and evergreen capital to portfolio construction, procurement savings, and the next phase of mid-market growth. This conversation is a masterclass in how to partner with GPs the right way.

Disclaimer: This podcast is provided for general and educational purposes only and is not intended to constitute legal, tax, securities or investment advice or a recommended course of action in any given situation. All opinions and views constitute our judgments as of the date of production and are subject to change at any time without notice. This information is provided for illustrative purposes only and is not a prediction, projection or guarantee of future performance. All investing is subject to market risk, including the loss of principal.

Highlights:

• How Hunter Point entered the GP-stakes market nearly a decade after the first movers—and why timing still mattered
• Why auctions distort alignment and how proprietary relationships build long-term trust
• How Hunter Point targets 10–25% ownership stakes while keeping founders in control
• Why independence and focus on GP stakes (not competing asset classes) create cleaner alignment
• How bespoke structures—carry attachments, earn-outs, and yield features—bridge valuation gaps
• Why evergreen capital matches the long-term nature of GP partnerships
• How proprietary origination becomes a flywheel of trust, referrals, and inbound deal flow
• Why procurement platforms, credit solutions, and strategic advice create measurable LP value
• How Hunter Point defines “mid-market” GPs and why sector specialists are the next alpha engines
• What causes GP-stake deals to fail—and how to avoid misalignment and mediocre partnerships
• Why patience, education, and “strategic patience” are the rarest skills in private markets

Guest Bio:

Mr. Hibberd is a Managing Director and serves as Chief Investment Officer at Hunter Point Capital.

Prior to joining HPC, Mr. Hibberd served as a Managing Director and Member of the Investment Committee within The Blackstone Group’s (“Blackstone”) GP stakes business, Strategic Capital Holdings. During his seven years at Blackstone, Mr. Hibberd facilitated key transactions and was responsible for deal team coordination, due diligence, term negotiation, and execution.

He also supported the Group’s origination effort, helping to source proprietary investment opportunities for the firm. Prior to Blackstone, Mr. Hibberd was an Associate in KKR & Co.’s North American Private Equity Group and an Associate in Goldman Sachs’ Global Natural Resources Group.

Mr. Hibberd earned his M.B.A. from Harvard Business School and his degree in Engineering from Cambridge University.

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.

Stay Connected:

X / Twitter: David Weisburd: @dweisburd

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Melvin Hibberd: https://www.linkedin.com/in/melvin-hibberd-bab4b018b/

Links Hunter Point Capital: https://www.hunterpointcapital.com/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com. (0:00) Preview (0:50) Welcome and Guest Introduction: Melvin Hibberd (0:58) Hunter Point's Market Entry, Strategy, and Competitive Edge (7:24) Structuring Deals, Aligning Interests, and Evergreen vs Fixed Term Funds (14:40) Proprietary Deal Sourcing, Portfolio Impact, and Differentiation Strategies (20:24) Portfolio Construction, Mid Market Significance, and LP Concerns (28:39) Benefits of GP Stakes, Investment Types, and Failure Reasons (36:53) Key Man Risk, Alignment, and LP-Driven Sourcing (43:27) Lessons from Launching Hunter Point and Ideal Deal Characteristics (48:23) Timeless Advice for Young Professionals (50:09) Closing remarks

David Weisburd had a chance to witness live the conversation between Jack Kokko, Founder & CEO of AlphaSense, and Lloyd Blankfein, former Chairman and CEO of Goldman Sachs, during AlphaSummit 2025 in New York City. In this wide-ranging discussion, Jack draws out Lloyd’s reflections on his early years in Brooklyn, his path to leading Goldman Sachs, and the lessons learned from steering the firm through periods of volatility and transformation. Together they explore how leadership, risk, and technology continue to shape Wall Street—and what it takes to stay adaptable in an ever-changing world. Highlights:

• How Lloyd’s early life in Brooklyn influenced his leadership style
• Lessons from being rejected by Goldman Sachs — and eventually running it
• Guiding Goldman through the 2008 financial crisis and its aftermath
• The value of partnership culture and communication in high-performance teams
• The changing dynamics of Wall Street amid AI and automation
• Balancing risk, intuition, and data in modern decision making
• The evolving relationship between private and public markets
• Lloyd’s reflections on adaptability, market cycles, and staying ahead of change

Guest Bio:

Lloyd Blankfein served as the Chairman and CEO of Goldman Sachs from 2006 to 2018, leading the firm through the global financial crisis and major transitions in global markets. He remains an influential voice on economic leadership, risk management, and the future of finance.

Host Bio:

Jack Kokko is the Founder and CEO of AlphaSense, a market intelligence and search platform used by financial institutions and corporations worldwide. His work focuses on advancing decision making through AI-powered information discovery.

Learn more about AlphaSense and upcoming AlphaSummit events at: alpha-sense.com. (0:00) Introduction (1:46) Lloyd Blankfein's Early Career and Decision-Making Reflections (7:13) Leadership, Communication, and Managing Teams (10:27) Evolution of Wall Street and Technological Impacts (15:30) Automated Trading: Risks and Trust in AI (19:23) Investment Banking Risk Control and Balancing Innovation (21:48) Thought Experiment: Starting a New Investment Bank (24:12) Equity Market Evolution and the Rise of Private Markets (31:18) Big Picture Market Changes and Future Speculations (34:25) Advice for Investors in an Evolving Market (36:12) Closing remarks

How do you invest when it’s “too early for data”—but just right for conviction? In this episode, I speak with Vivek Ladsariya, Managing Director at Pioneer Square Labs (PSL), about what it really takes to back founders before traction, before funding rounds, and sometimes even before incorporation. Vivek shares how he partners with founders as a thought partner instead of a coach, why iteration trumps ideas, and how efficiency and automation have rewritten what it means to earn a Series A today. From early-stage pattern recognition to AI-driven productivity and new definitions of founder resilience, this conversation is a masterclass in what “being early” actually means in 2025 Highlights:

• How investing “too early” often creates the strongest long-term alpha
• Why the best investors act as thought partners, not back-seat CEOs
• How ego, relentlessness, and intellectual honesty predict outlier founders
• Why great ideas matter less than constant iteration and customer focus
• How Series A benchmarks have shifted to roughly $7 million ARR—and what it means for founders
• Why AI is the new leverage for coding, sales, and operations efficiency
• How language itself has become code, allowing anyone to automate with LLMs
• How PSL’s studio + fund model accelerates founders from zero to one
• Why small, elite teams outperform larger organizations in the AI era
• How becoming a parent sharpened Vivek’s priorities and patience as an investor

Guest Bio:

Vivek Ladsariya is a Managing Director at Pioneer Square Labs (PSL), where he leads pre-seed and seed investments out of PSL Ventures Fund II ($100 million), focusing on AI, cybersecurity, infrastructure, industrial tech, and DevOps. Before joining PSL, he was a General Partner at SineWave Ventures and an entrepreneur behind ventures such as GameGarage and Moyyer.

His investments include Databricks, Rescale, Osaro, and Evolv Technologies (NASDAQ: EVLV). Vivek holds an MBA from Yale University and a B.E. from the University of Mumbai.

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/ Vivek Ladsariya: https://www.linkedin.com/in/vivek-ladsariya-8a828535/

Links Pioneer Square Labs: https://www.linkedin.com/company/pioneer-square-labs/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com. (0:00) Preview (0:06) Evolution of programming languages and business automation (1:05) Welcome and guest introduction (1:16) Investing early in startups and the role of a VC (4:17) Creating value in startups and being an effective thought partner (7:11) Handling crises, feedback, and the role of ego in startups (11:27) Ray Dalio's concept of believability and startup ideas (18:22) Customer pain points and the idea maze (21:17) Predicting entrepreneurial perseverance and evaluating founders (24:44) Iterating startup ideas and future Series A expectations (35:16) The impact of AI on programming and business processes (42:56) Preparing skills for a post-AI world (46:14) Pioneer Square Labs and thoughts on seed strapping (50:52) Advice to a younger self and the impact of life changes on investing (57:07) Closing remarks

How does an $8B venture platform turn a 650-fund network into a repeatable co-investing edge? In this episode, Jonathan Roosevelt, Managing Director at Industry Ventures, explains how the firm evolved from a pioneer in venture secondaries into a platform combining secondaries, co-investments (directs), fund-of-funds, and tech buyout—with AUM “a little over $8B” and 25+ years in market. We break down why Series A/B/C co-investing requires a different lens than seed, how believability guides which GPs get a “stamp” for later-stage deals, and why customer calls are ground truth when underwriting mid-stage businesses. Jonathan also shares how asymmetric information and inflection points create true co-invest alpha—and when to ignore comps for N-of-1 companies. Highlights:

• $8B platform: Secondaries, co-invests, fund-of-funds, tech buyout
• 650-fund network: ~250 primaries, ~400 via LP secondaries
• Co-invest engine: 100% sourced from seed/early GP relationships
• Seed vs. mid-stage: PMF stories vs. durable unit economics
• Believability lens: Repeatable process before a later-stage “stamp”
• Ground truth: Independent customer diligence over CEO references
• Asymmetry & inflection: Board insights at turning points drive edge
• Do the unscalable: Sector depth, real customer intros, hands-on help
• N-of-1 underwriting: Backcast valuation from end-state outcomes

Guest Bio:

Jonathan Roosevelt is a Managing Director at Industry Ventures, where he focuses on originating, valuing, and managing primary fund commitments, early secondary LP stakes, and direct company investments within the firm’s Direct & Partnership Holdings strategies. Previously a Venture Partner at Industry Ventures (2017), he was promoted to Managing Director in 2019; earlier, he founded and led companies, was an early employee/VP of Sales at SoFi, and invested as an angel in Fitbit. He holds an MBA and BA from Harvard.

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/ Jonathan Roosevelt: https://www.linkedin.com/in/jroosevelt/

Links Industry Ventures: https://www.industryventures.com/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com. (0:00) Preview (0:04) Customer feedback's impact on investments (1:03) Industry Ventures' co-investment strategy (3:44) Co-investment opportunity lifecycle (7:19) Assessing investment manager credibility and diligence (17:14) Identifying exciting co-investment opportunities (19:47) Triangulating information for investment decisions (23:04) Customer enthusiasm in the investment process (27:16) Relationship significance in investment decisions (29:34) Operator vs investor perspectives in venture capital (34:01) Risk management for seed stage investments (37:10) Competing as an emerging manager in venture capital (38:43) Valuation strategies for new venture capitalists (41:18) Closing remarks

What if the U.S. dollar’s dominance has already ended—and we’re just living through the lag? In this episode, I sit down with Balaji Srinivasan, one of the most original thinkers in technology and finance, to unpack his boldest prediction yet: the death of the dollar and the rise of a digital, decentralized global economy. Balaji explains how inflation, weaponized finance, and technological sovereignty are accelerating a massive shift away from traditional monetary systems—and why crypto, AI, and network states could define the next reserve paradigm. We go deep into why he believes the internet will replace the nation-state, how founders can build parallel institutions from scratch, and why opting out—not lobbying—is the only path forward. This is not a doomsday take. It’s a blueprint for builders who believe the future is already here. Highlights:

• The Network State: How online communities will evolve into sovereign cities.
• From Crypto to Cities: Why blockchain can fund and govern real-world nations.
• The Balaji Fund: Backed by Brian Armstrong, Marc Andreessen, and David Sachs—investing in “techno-radicals.”
• Replacing Broken Systems: How founders can build alternatives to failing institutions like education, healthcare, and media.
• Lessons from China: What the U.S. can learn from China's manufacturing and infrastructure speed.
• India’s Decade: Why Balaji believes India is becoming the new global tech engine.
• High-Risk Seed: Why his investment strategy targets contrarian, world-changing founders.
• From Bitcoin to Benchling: Inside Balaji’s personal portfolio and his “index the outliers” approach.
• The Frontier Mindset: How today’s founders can reclaim the spirit of Silicon Valley’s pioneers.
• Opt-in Capitalism: Why the future of governance will be voluntary, networked, and global.

Guest Bio:

Balaji S. Srinivasan (born May 24, 1980) is an American entrepreneur, investor and author. He co-founded genetic-testing firm Counsyl and led cryptocurrency company Earn.com before becoming first CTO of Coinbase and a General Partner at Andreessen Horowitz. He holds a BS, MS and PhD in Electrical Engineering and an MS in Chemical Engineering from Stanford University.

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.

Stay Connected:

X / Twitter: David Weisburd: @dweisburd

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Balaji Srinivasan: https://www.linkedin.com/in/balajissrinivasan/?originalSubdomain=sg

Links Balaji Srinivasan: https://en.wikipedia.org/wiki/Balaji_Srinivasan

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com. (0:00) Preview (3:24) Steps to create a new country and the concept of network states (7:18) The Internet's transformative impact and decentralized countries (10:41) Crypto tribalism and Bitcoin's economic role (14:13) Cryptocurrencies as emerging digital nations (17:42) Government inefficiencies and the future of democracy with digital currencies (21:27) The evolution of capitalism and democracy (23:37) The role of DAOs in digital governance and network states (31:09) Utilizing crypto for crowdfunding and real estate (35:01) Introduction to the Balaji Fund and investment strategies (38:15) Technological solutions for societal problems (41:16) Profit maximization aligned with values and addressing Baumol's cost disease (45:03) Regulatory challenges in healthcare and childcare (47:34) DAOs' potential in real estate and community formation (51:20) Translating digital processes into physical communities (54:16) Balaji Fund's investor alignment and societal impact (1:02:21) Government, technology, and cost dynamics (1:06:20) Political pressures and pension paradoxes in investments (1:09:15) Diagnosing inefficiencies in real estate and construction (1:11:17) China's strategic advantages and US challenges (1:15:17) US-China strategies and the American dynamism dilemma (1:25:26) US political and social divides, government failures, and potential solutions (1:27:49) Competing with traditional institutions through innovation (1:30:20) Addressing societal issues with technology and portfolio construction (1:32:37) Investing in high-potential founders and the rise of Indian tech talent (1:35:28) Global capital impact of crypto and cybersecurity importance (1:37:14) Balaji's investment strategy and notable successes (1:41:33) Closing remarks

What happens when one of tech’s best community builders turns his playbook on venture capital itself? Ryan Hoover — the founder of Product Hunt and Investor at Weekend Fund — joins me to unpack how he’s reinventing early-stage investing. From building one of the internet’s biggest startup communities to managing a fund with 360+ LPs, Ryan shares the hard-won lessons on productizing VC, scaling systems as an introvert, and finding founders who hold true “earned secrets.” We dive into his journey from launching Product Hunt to building Weekend Fund’s third vehicle, how he thinks about portfolio construction, why weird ideas often win, and what it really takes to back the next generation of breakout founders. Whether you’re a founder, operator, or investor — this episode is packed with insights on scaling yourself, spotting alpha before it’s obvious, and turning community into competitive advantage. Highlights:

• How Ryan built Product Hunt into a launchpad for over 100,000 startups.
• The story behind raising from 360+ LPs — and why one investor literally became a monk.
• Why Weekend Fund prefers staying small to keep conviction high.
• The psychology of “weird” investing — and why strange ideas often outperform.
• How Ryan productized LP intros and scaled value-add through software.
• Why the best investors give without expecting anything in return
• How to build a scout network that multiplies your reach without adding complexity.
• The key traits of elite super connectors (and why Ryan doesn’t see himself as one).
• Why founders with “earned secrets” beat consensus every time.
• Ryan’s one piece of advice to his younger self before launching his first fund.

Guest Bio:

Ryan Hoover is the Founder and Investor at Weekend Fund, an early-stage venture capital firm investing in founders with earned secrets—deep insights derived from firsthand experience. Weekend Fund has raised three funds and invested in over 100 startups globally, including Deel, Replicate, and Rally, backed by a diverse community of more than 360 limited partners. Before founding Weekend Fund, Ryan founded Product Hunt, the platform that helped launch tens of thousands of startups and shaped how the tech world discovers new products. He has since focused full-time on building a new venture model centered around community, transparency, and product thinking.

Stay Connected:

X / Twitter: David Weisburd: @dweisburd Ryan Hoover: @rrhoover

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

Links Weekend Fund: https://www.weekend.fund/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com. (0:00) Preview (0:14) Secrets, lived experience, and productizing LP intros (1:51) Fundraising challenges and LP base management (3:07) Downsides and expectations with 360 LPs (6:31) Venture capital as a product and Weekend Build experiment (9:10) Rolodexer success and becoming an elite super connector (14:18) Using value add to win deals and portfolio construction strategies (22:10) Ryan Hoover's LP activities, SPVs, and strategic investments (26:11) Scaling productivity and weekend partners program (29:17) Transparency and investing in non-consensus companies (37:42) Information diet, advice to younger self, and early strategies (42:00) Best product importance vs. portfolio construction and market changes (43:32) Managing a large portfolio and scaling support with tools (44:14) Closing remarks

Why are Institutional Investors betting big on Private Markets? Franklin Templeton oversees more than $1.6 trillion in assets, with over $260 billion dedicated to private markets. But what’s driving this massive shift — and how are the world’s largest allocators navigating liquidity, valuations, and the next era of private credit? In this episode, I speak with John Ivanac, Head of U.S. Institutional Alternatives at Franklin Templeton, to uncover how the firm is positioning itself for the next decade of alternative investments. We explore the evolution of private markets post-GFC, the consolidation wave among asset owners, and why liquidity, governance, and strategy selection are becoming more critical than ever. John also shares his perspective on Franklin’s acquisition strategy, how they integrate firms like Lexington Partners and Benefit Street Partners, and what it truly means to be a “trusted partner” to LPs in an increasingly complex market. Highlights:

• Structural Shifts: How regulation and capital formation reshaped private markets post-GFC
• Private Credit Boom: Why a $3.5T market could expand 10x in the next decade
• Secondaries Surge: Inside Franklin’s bet on Lexington Partners and the maturing PE ecosystem
• LP Consolidation: Why institutional allocators are backing fewer but deeper partnerships
• Holistic Partnerships: How Franklin Templeton redefines client alignment beyond products
• Digital Assets Strategy: Why the firm built a 60-person blockchain and crypto investment team
• Retail & Institutional Synergy: The future of democratizing alternatives responsibly
• Culture of Long-Termism: How generational leadership drives Franklin’s innovation mindset

Guest Bio:

John Ivanac is the Head of U.S. Institutional Alternatives at Franklin Templeton, where he focuses on expanding and managing the firm’s suite of Alternative Investment Solutions for institutional investors.

John brings over 20 years of experience in the alternatives space, having previously served as Managing Director, Head of U.S. Consultant Relations at Partners Group and Global Head of Alternatives at BlackRock. He has also held senior leadership roles at The TCW Group, Scoggin Capital, and Barclays.

He holds a J.D. from St. John’s University School of Law and a B.A. from Rutgers University, bringing a deep understanding of both the structural and human dynamics driving today’s institutional capital markets.

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.

Stay Connected:

X / Twitter: David Weisburd: @dweisburd

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

Links Franklin Templeton: https://www.franklintempletonglobal.com/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com. (0:00) Preview (0:59) Introduction to Franklin Templeton and private investment strategies (2:51) Drivers and opportunities in private market growth (7:15) Institutional investment and volatility in alternatives (14:44) Future outlook and building a significant portfolio (19:02) Acquisitions, strategic focus, and consolidation trends (21:51) Partnering and aligning with asset managers (25:46) Culture and long-term vision in expanding portfolios (28:46) Franklin Templeton's benefits for LPs and manager consolidation (35:58) Digital assets and balancing investor types (39:40) Retail market practices and investor education (45:38) Career advice and patience in investment (47:53) Building credibility, trust, and partnership roles (50:59) Addressing short termism in public markets (51:31) Closing remarks

Can a $324.3 billion wealth manager reinvent how high-net-worth investors access private markets? In this episode, I speak with Robert Picard, Head of Alternative Investments at Hightower Advisors, who is leading one of the industry’s most ambitious expansions into private markets. We discuss how Hightower is bringing institutional-grade research, access, and due diligence to individual investors, what the NEPC acquisition means for its alternatives platform, and how technology and AI are reshaping the way portfolios are built. Robert also shares lessons from more than 35 years of building multi-billion-dollar alternative platforms atThe Carlyle Group/Rock Creek, Optima Fund Management, RBC Capital Markets and State Street/InfraHedge, and explains why the future of wealth management will look more like an endowment model than ever before. Highlights:

• How Hightower is bridging institutional research with private-client portfolios
• The strategic rationale behind acquiring NEPC and its impact on Hightower’s platform
• Why private markets are still under-owned among high-net-worth investors
• The “democratization and miniaturization” of private markets and what that means for access
• Robert’s framework for allocating 10–30% of portfolios into private assets
• Why illiquidity can actually be your ally during market downturns
• How AI and technology will transform investment diligence and portfolio construction
• The evolution of independent wealth managers competing with Wall Street wirehouses
• Why maintaining curiosity, networks, and fun are keys to a 35-year investing career

Guest Bio:

Robert Picard is the Head of Alternative Investments at Hightower Advisors, where he leads the firm’s alternative investment platform and oversees research, due diligence, and portfolio design. He previously held senior roles building multi-billion-dollar alternative platforms at The Carlyle Group / Rock Creek, Optima Fund Management, RBC Capital Markets, and State Street / InfraHedge, and served as Head of Alternatives at First Republic Private Wealth Management.

Robert has over 35 years of experience in global investing, with a background in equity derivatives, structured products, and private markets. He is widely regarded for his insights on the convergence of institutional and private wealth investing

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.

Stay Connected:

X / Twitter: David Weisburd: @dweisburd

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

Links Hightower Advisors: https://hightoweradvisors.com/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com. (0:00) Preview (1:07) Hightower Advisors and NEPC Acquisition Strategy (2:33) NEPC's Research Benefits and Portfolio Differences (5:55) Democratization of Private Markets for Individuals (8:56) Private Asset Allocation Strategies (13:35) Illiquidity Benefits and Market Downturn Preparation (17:34) Long-Term Cybersecurity and AI Investment Strategies (23:06) The 2030 Asset Management Outlook (24:26) AI in Private Market Research and Growth Projections (28:40) Life Sciences Investment Opportunities (30:18) Independent Wealth Managers vs. Wirehouses (33:20) Evolving Role of Family Offices (36:00) Diversification in Private Markets and Future Trends (42:05) Technological Advancements in Private Markets (45:02) Managing Multiple Advisor Practices and Efficiency with AI (49:33) Career Advice for Young Professionals (51:11) Work-Life Balance and Industry Transformations (51:58) Closing Remarks and Future Podcast Plans (52:09) Closing remarks

If “fixed income is broken,” what are investors actually missing—and how should they rebuild the 40% to protect and compound through drawdowns? In this episode, I speak with Thomas E. Swaney II, former Chief Investment Officer of Global Fixed Income at Northern Trust Asset Management, who oversaw more than $600 billion across global fixed income. Thomas explains why traditional bond allocations fail when it matters most, how to separate duration from credit risk, and how to use notional leverage to target true diversification without sacrificing liquidity. We explore the structural flaws in 60/40, how to design a fixed income portfolio that actually offsets equity drawdowns, and why the future of bond investing depends on better risk budgeting—not higher yield. Highlights:

• Fixed Income Is Broken: Why most bond portfolios don’t diversify when equities fall
• Rebuilding the 40%: Duration vs. credit and managing correlation through regimes
• Notional Leverage: Using treasury futures and IG CDX to build volatility with quality
• Risk Parity Framework: Allocating by contribution to risk, not nominal dollars
• Rebalancing Alpha: Liquidity and negative correlation as the real edge
• Curve Positioning: Why the belly of the curve often outperforms the long end
• Convexity Mismatch: Public vs. private assets and the lagged rebound effect
• Inflation Regimes: How correlation flips and when to incorporate TIPS
• Leadership & Culture: Lessons from Ellington and Northern Trust on process and debate
• The Next Decade: Bonds are relevant again—if built for resilience

Guest Bio:

Thomas E. Swaney II is the former Chief Investment Officer of Global Fixed Income at Northern Trust Asset Management, where he had broad oversight of the $600+ billion fixed income platform, spanning business management, portfolio management, and strategy. As CIO, he chaired the Fixed Income Strategy Committee, guiding macroeconomic themes, risk budgeting, and portfolio construction across all fixed-income portfolios. He also served on Northern Trust’s Investment Committee and Executive Group within Asset Management.

Prior to Northern Trust, Thomas held senior executive and portfolio management roles at J.P. Morgan Asset Management, Morgan Stanley Investment Management, OFI Global Asset Management, and Ellington Management Group. He holds a B.B.A. and M.B.A. with a concentration in corporate financial analysis, as well as an M.Sc. in Finance from the Kelley School of Business at Indiana University, and has more than 26 years of investment experience.

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.

Stay Connected:

X / Twitter: David Weisburd: @dweisburd

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Thomas E. Swaney II: https://www.linkedin.com/in/swaneycio/

Links Factor Two Capital Management: https://brand.site/factortwocapital

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com. (0:00) Preview (0:48) Thomas Swaney's career and Miller Anderson's open debate culture (5:00) Challenges and impacts of open dialogue culture in investment firms (6:42) Education systems and their influence on investment thinking (7:47) Leadership vs. Investment Skills (9:40) Shifting Northern Trust's focus and lessons from Ellington (18:45) The role and strategies for fixed income in a diversified portfolio (23:35) Understanding market downturns and Bridgewater's equilibrium approach (27:24) Decomposing and maximizing efficiency in bond portfolios (33:56) Challenges and strategies with private assets in portfolios (38:40) The impact and use of leverage in investment portfolios (42:43) Introduction to Factor Two Capital Management (44:38) Exploring the relationship between volatility and expected values (49:16) Fed independence and market reactions to policy changes (51:35) Misconceptions about monetary policy and economic impact (53:04) Future outlook on fixed income versus equities and prediction markets (55:24) Closing remarks