How I Invest with David Weisburd

What are the real playbooks behind managing an $86B alternative asset platform—and where do the next decade’s returns actually come from? In this episode, I sit down with Payton Brooks, Managing Director on Future Standard’s Primary Investments team, to unpack the operating system behind a multi-strategy LP: how a combined platform serves both institutions and the wealth channel, why mid-market private equity still offers the best shot at alpha, and how evergreen structures can reduce cash drag while preserving optionality. We cover sourcing (spinouts, emerging managers), what great GPs do in downturns, the co-invest / secondaries / credit toolkit, and the partnership behaviors that earn re-ups across multiple fund cycles. Highlights:

• Future Standard under the FS + Portfolio Advisors merger with ~$86B AUM
• How wealth clients access institutional alternatives via structured vehicles
• Mid-market outperformance vs. large-cap PE
• Operating depth and specialization as scale drivers
• Evergreen strategies reducing cash drag
• Anchor LPs as credibility signals
• Partnership transparency as LP/GP discipline
• Co-invest, secondaries & credit augmenting optionality
• Patience, credibility & compounding relationships

Guest Bio:

Payton Brooks is a Managing Director on Future Standard’s Primary Investments team, focusing on manager selection and portfolio construction across the private-equity landscape. He joined the firm in 2014, and holds a B.A. from Southern Virginia University and an MBA from the Yale School of Management. Future Standard is a global alternatives platform investing across private equity, credit, and real estate, serving both institutional and private-wealth clients; the firm rebranded from FS Investments in July 2025 following its combination with Portfolio Advisors in June 2023.

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

Links Future Standards: https://www.futurestandard.com/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com. (0:00) Introduction (0:44) Client base and portfolio construction (1:40) Differences between high net worth individuals and pension funds (3:02) Access for high net worth investors to asset classes (4:05) Characteristics of successful private equity funds and large cap buyouts (9:21) Evaluating middle market managers and building relationships (16:40) Utilizing secondaries, co-investments, and internal team structure (19:01) Traits of elite superstar GPs and repeatable value creation (23:22) Decision-making process and portfolio construction within the buyout fund (28:39) Pension fund investment in Evergreen Fund mechanics and benefits (34:14) Evergreen Fund strategy, market impact, and comparison to drawdown funds (41:32) Challenges and strategies for emerging managers (44:02) Securing anchor investors and LP decision-making (47:58) Importance of time optionality in fund investments (51:08) Balancing early and late fund investments (53:20) Career reflections and advice to younger self (55:23) Enhancing investment knowledge and leveraging partners for insights (57:06) Closing remarks

Why do ~90% of first-time managers fail before Fund II/III—and what separates durable fund builders from good investors? In this episode, I unpack that question with Conrad Shang, Founder & Managing Partner at Ensemble VC. We examine why being a great investor is necessary but not sufficient to be a great fund manager, how to build for durability across cycles, and the partnership practices that earn long-term LP trust. Conrad shares lessons from UTIMCO, Norwest, and Bain Capital Ventures; why sometimes the hardest move is sitting out frothy markets; and how Ensemble uses a team-first lens and internal data products to focus time on the few opportunities that matter. We also discuss defense tech’s shift from “taboo” to mainstream, and why communication cadence and transparency determine who survives the first four to five years—when most managers wash out. Highlights:

• Investor ≠ fund manager: portfolio construction, firm-building, and 10–12 year horizons matter as much as deal picking.
• Durability over cycles: sometimes the right move is doing zero deals for ~12 months to avoid overpaying.
• Power laws require survival: stay in the game long enough to catch the outliers; size and pacing are part of edge.
• LPs as partners, not capital: trust, warm introductions (“trust by proxy”), and over-communication—without “crying wolf.”
• Team > solo founder myth: first hires and sequencing reveal how companies will actually be built.
• Defense tech arc: from taboo to obvious—examples include ICON (3D-printed homes), Saronic, and Manifest (ex-Palantir).
• Data-driven firm design: internal platform (“Unity”) reallocates time from low-yield first meetings to high-conviction winning.
• Pilot fund outcomes: Ensemble’s Fund I (pilot) marked ~12×; scaling the model required re-architecting org + software.

Guest Bio:

Conrad Shang is Founder & Managing Partner at Ensemble VC. Previously, he led/managed venture investing at UTIMCO and invested at Norwest Venture Partners and Bain Capital Ventures; earlier he was a consultant at Bain & Company. He’s a Kauffman Fellow and has sat on both the GP and LP sides of the table—experience that informs Ensemble’s product- and data-driven approach to firm 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.

#VentureCapital #VC #Startups #OpenLP #AssetManagement

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X / Twitter: David Weisburd: @dweisburd

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

Links Ensemble VC: https://www.ensemble.vc/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com. (0:00) Introduction (1:25) Fund management skills beyond investing (2:06) Time horizons in investments vs. fund management (4:24) Navigating economic cycles and long-term strategy (7:06) Venture investing and the power law paradox (8:24) Emerging challenges for new fund managers (10:48) Investment timing in defense tech and 3D printing (11:44) Team dynamics and talent as success predictors (14:57) Trust-building lessons from UTIMCO (19:04) The critical role of trust in LP-GP dynamics (21:21) Treating LPs as partners and the educational aspect (23:50) Mutual benefits of LP-GP collaboration (29:55) Fostering trusted long-term LP relationships (33:46) Transparency and communication with LPs (36:19) Investment theses and relationship importance (41:58) Insights from LP experience at UTIMCO (46:41) Practices of successful GPs (51:58) Relationship alpha and its impact on venture success (52:32) Ensemble's Fund One and its approach (54:16) Data and software in Ensemble's investment strategy (57:06) Data-driven investment case studies (1:00:37) Ensemble's Unity platform and efficiency tools (1:03:04) Using data for informed investment decisions (1:06:06) Team cohesion and its importance (1:08:14) Closing remarks

What really happens inside the hidden world of family offices—and why do they invest so differently from institutions? In this episode, I explore that question with Sid Malhotra, Chief Investment Officer at Kactus Capital, a single family office. Sid reveals how family offices align incentives between principals and investment teams, the advantages of having true “skin in the game,” and why their long-term, absolute-return mindset stands apart from pensions, endowments, and foundations. We also discuss the unique strategic role family offices play—from backing zero-to-one opportunities to leveraging deep sector expertise and networks—and how Sid’s career path, from Citadel to Pritzker Group to his current role, shaped his approach to risk, alignment, and building resilient portfolios. Highlights:

• Alignment over agency: how Kactus ties compensation and co-investment directly to long-term portfolio performance.
• Single vs. multi-family offices: why governance, focus, and principal control make a difference
• Strategic capital: family offices as early backers of crypto, seed managers, and illiquid opportunities institutions avoid
• Lessons from six years at the Pritzker Group: how legacy ownership and manufacturing DNA shape an investment lens
• Absolute returns and relative returns: why compounding capital while minimizing losses guides Sid’s philosophy
• Preparing for corrections: dry powder, T-bills, and opportunistic offense in market sell-offs
• Citadel training: lessons on multi-strategy flexibility, thinking across the capital structure, and risk-reward sizing
• The total portfolio approach: blending macro-awareness, bottoms-up selection, and thematic top-down views
• Career advice from Booth to CIO: why networking early is as critical as working hard

Guest Bio:

Sid Malhotra is the Chief Investment Officer at Kactus Capital Management, a single family office where he leads all investment activity across public and private markets. Before joining Kactus, Sid spent over six years at the Pritzker Group, helping steward the family’s legacy of business ownership and investing across multiple asset classes. Earlier in his career, he worked at Citadel, gaining multi-strategy and capital-structure investing experience. Sid holds an MBA from the University of Chicago Booth School of Business and a B.A. in Economics from the University of Michigan. He has completed the Value Investing Executive Education program at Columbia Business School and is a Chartered Financial Analyst (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.

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X / Twitter: David Weisburd: @dweisburd

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

Links Kactus Capital Management: https://www.kactuscapital.com/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com. (0:00) Introduction (2:09) Alignment of Interests and Trade-offs in Family Offices (5:24) Strategic Nature of Family Offices and Learnings from Pritzker Group (9:30) Focus on Absolute Returns and Criteria for Investment in a Manager (12:26) Investment Style: Jigsaw Puzzle vs. Treasure Hunt (14:24) Preparing for Market Corrections and Managing Dry Powder (18:19) Challenges of Cash Reserves and Strategy during Market Sell-Offs (22:33) Public vs. Illiquid Investments During Crises and Sources of Alpha (26:30) Lessons from Working at Citadel and Appeal of Multi-Strategy Firms (33:04) Impact of Tax Considerations on Portfolio Construction (35:46) Building a Career and Network Post-Business School (37:25) Closing remarks

Why is up to “$150 trillion” poised to migrate from public to private markets—and what will unlock that shift for RIAs and family offices? In this episode, I examine that question with David Sawyer, CEO & Co-Founder of Unlimited.ai. We unpack the real blockers to alternatives adoption—operational, reporting, diligence, and liquidity complexity—and how AI can turn PDFs and siloed portals into queryable, decision-ready data for LPs. We talk RIA psychology, the GP/LP information asymmetry, and why solving “complexity” is the catalyst for the public-to-private transition cited by industry leaders (including the oft-quoted $150T prediction). Highlights:

• Four kinds of complexity stopping alts adoption: access, legal/regulatory, reporting (K-1s, non-standard NAVs), and liquidity.
• Why operational complexity is the #1 reason many RIAs avoid alts (industry surveys ~40–50%).
• The public → private shift: volatility aversion + search for alpha and predictability.
• Information asymmetry has widened: trillion-dollar GPs vs. individuals and smaller RIAs—why tooling must level the field.
• AI’s role: extract, integrate, and chat with unstructured docs; unified LP workflow from access → diligence → reporting → exit.
• RIA reality: clients already bring outside deals/K-1s—consolidated balance-sheet reporting is now table stakes.
• Why due-diligence management is the sleeper pain point—and how comparative analytics change decisions
• Context for performance: the conversation references Kaplan–Schoar/PME research on PE vs. public markets (as discussed in-episode)

Guest Bio:

David Sawyer is CEO & Co-Founder of Unlimited.ai, an AI-native platform built to orchestrate LP workflows in private markets. Previously, he served as Managing Partner & COO at Legacy Knight, a multi-family office and alternatives platform, and as Managing Director at CAZ Investments. He holds a J.D. from the University of Houston Law Center, studied at the University of Texas at Austin, and is a CAIA charter holder.

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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LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ David Sawyer: https://www.linkedin.com/in/david-sawyer-a70ab912/

Links Unlimited.ai: https://www.unlimited.ai/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com. (0:00) Introduction (2:54) The role of technology in alternative investment management (7:31) Strategies for overcoming operational complexity in private markets (10:21) AI's impact on investor access and information symmetry (22:07) Standardization and transparency in private market investments (23:06) Empowering investors with technology and community initiatives (23:56) Closing remarks

How do you underwrite pre-seed founders when the only durable asset is the human—before there’s product-market fit? In this episode, I go deep with Mike Ma, Managing Partner at Sidecut Ventures, on his 30-day “work-alongside” diligence, why he optimizes for action-oriented self-awareness, and how to calibrate coachability—especially in go-to-market—without overfitting to investor bias. We unpack earned secrets, impact theses in education, climate, healthcare, and economic mobility, solo-GP advantages, alignment pitfalls from 2021-era rounds, and the mindset habits he wishes he’d had earlier: “write at a fourth-grade level” and “document your screw-ups.” Highlights:

• The 30-day “grind with them” model: watching founders operate to reduce storytelling bias.
• What predicts pre-seed survival: action-oriented self-awareness (execute fast and integrate feedback fast).
• Coachability, defined: focus on go-to-market (not deep tech) and respond to market-generated feedback.
• Earned secrets: the unfair advantage born at the intersection of novel markets + lived expertise.
• Why solo GPs can be more aligned: speed, conviction, and operator empathy at pre-seed.
• Valuation ≠ victory: how 2021-style prefs/marks can zero founders despite solid outcomes.
• Two habits for builders & investors: write simply and log your mistakes to kill self-deception.

Guest Bio:

Mike Ma is the Managing Partner of Sidecut Ventures, a pre-seed venture firm backing “coachable superheroes” in sectors including economic mobility, digital health, climate, and education. He brings a background as both an investor and operator, with prior roles that span venture capital, operating leadership, and company building. Before founding Sidecut, Mike held leadership positions at firms such as Sway Ventures and Nex Cubed, where he launched fintech initiatives and accelerator programs. He also served as a marketing leader at high-growth startups including Betterment and Own Up, and earlier in his career worked in brand strategy at major financial institutions. A graduate of Harvard University, Mike now applies his experience across investing, operations, and go-to-market strategy to help early-stage founders succeed.

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 Ma: https://www.linkedin.com/in/michaelwma/

Links Sidecut Ventures: https://www.sidecut.vc/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com. (0:00) Preview (2:30) Assessing and predicting startup success (7:06) Coachability in startup founders (13:14) Market size misconceptions and value creation platforms (22:15) Solo GPs and early-stage startup advantages (24:14) Innovation and the AI startup landscape (25:35) Optionality and premium in early-stage funding (26:48) VC-startup alignment and second-order effects (29:22) Misalignment in funding and tragic outcomes (29:50) Thirty-day LLM project insights (30:41) Asymmetric information and bias in investing (33:20) Coaching founders and personal advice (36:57) Closing remarks

How can families preserve wealth and well-being across five or more generations? In this episode, I dive deep into a conversation with James E. “Jay” Hughes, Jr., legendary family wealth advisor and author of five influential books including Family Wealth. Jay shares stories from advising families for over 50 years—why flourishing, not just financial returns, is the real measure of wealth; how families like the Rothschilds and Fords illustrate both triumph and tragedy; and why choosing trustees wisely may be the single most important decision for multi-generational continuity. We explore governance, purpose, philanthropy, Aristotle’s philosophy of flourishing societies, and Jay’s own midlife realization that the true professional question is not “what do you need?” but “how can I help?” Highlights:

• The Rothschild family story: diversification of human, intellectual, and social capital as a foundation for flourishing
• Trustee decisions: why one poor choice can unravel a fortune over generations
• The Ford family cautionary tale: Henry Ford’s dominance over Edsel, and Henry Ford II’s turnaround
• Aristotle’s timeless lesson: no flourishing society without flourishing families
• Why purpose and philanthropy grow—not deplete—family wealth
• The billionaire pledge: altruism with promise, but outcomes still unproven
• Jay’s midlife shift: moving from fulfilling needs to asking, “how can I help?”
• His father’s wisdom: knowledge is fungible, courage is invaluable

Guest Bio:

James E. “Jay” Hughes, Jr. is a pioneering family wealth advisor, author, and thought leader who has advised some of the world’s most prominent families for over five decades. A sixth-generation lawyer, Jay began his career in trusts and estates law before dedicating his life to helping families flourish across generations. He is the author of five books, including Family Wealth: Keeping It in the Family, and a frequent speaker on family governance, stewardship, and purpose. Jay has served as a trustee, mentor, and confidant to multi-generational families globally, and is recognized as one of the foundational voices in the modern family office movement.

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

Links About James E. Hughes, Jr.: https://www.jamesehughes.com/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com. (0:00) Introduction (1:39) James E. Hughes, Jr.: Background and trust and estate law career (3:14) Joint decision making challenges in wealthy families (5:05) Insights on creativity from Zixanth Mahai's book (9:16) Importance of trustee selection for wealth preservation (10:48) The Ford family's rise, fall, and legacy transformation (15:06) Purpose and philanthropy's role in sustaining family wealth (20:59) Billionaire's giving pledge and its effects on wealth management (22:32) James E. Hughes, Jr.'s advice for young professionals (27:07) Closing remarks

How should a public pension build an active equity and absolute-return program—without diluting alpha or chasing the “hot” manager? In this episode, I go deep with Brian Miller, Senior Investment Officer at the Sacramento County Employees’ Retirement System (SCERS), on constructing a $6B public-equity book inside a ~$15B plan, sizing managers, and using absolute-return strategies as true diversifiers. Brian reflects on 16 years at Tukman Grossman Capital Management (value, long-term compounding, and staying consistent), the realities of “LP capture” across cycles, and why tracking error isn’t the right risk lens. We unpack manager due diligence (including on-site visits), active vs. passive trade-offs, the global/US mix, and how SCERS uses MSCI Caissa for whole-portfolio visibility. Highlights:

• Lessons from Tukman Grossman Capital Management: consistency, long-term compounding, and fitting the “value/core” role for top LPs.
• LP capture in practice: how client flows can force or fund decisions—08/09 liquidity, 2020 upgrades, and who doubles down in drawdowns.
• Value vs. growth & small-cap value today: quality dispersion, a smaller small-cap universe, and why “stocks follow earnings” over time.
• Portfolio construction at SCERS: shifting to include global vs. pure international; active where it counts with ~half of US equity passive.
• Tracking error ≠ risk: focus on downside risk; information-ratio “gotchas” when TE is kept too low.
• Absolute Return (7% sleeve): diversifiers (event-driven, macro, market-neutral, derivatives-based arb) that protected in 2022 and target mid-single-digit returns with low vol.
• Tooling: how MSCI Caissa gives top-to-holdings look-through across public & private to manage exposures.
• Manager selection & diligence: narrow the funnel, visit on-site, prevent false positives, and stay rooted in the original thesis.
• Career advice: be a continual learner, build networks early, and develop conviction to hold through criticism.

Guest Bio:

Brian Miller is a Senior (Retirement) Investment Officer at the Sacramento County Employees’ Retirement System (SCERS), where he focuses on Global Public Equity and Absolute Return programs. Before SCERS, he spent 16 years at Tukman Grossman Capital Management in research and portfolio roles. At SCERS he leads manager selection and portfolio construction across public equity and diversifying 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

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X / Twitter: David Weisburd: @dweisburd

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Brian Miller: https://www.linkedin.com/in/brian-miller-205a85/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com. (0:00) Introduction (4:20) Long-term investing and its impact on success (8:22) Navigating market crises and opportunities (12:29) Dynamics of small cap value investing (16:51) Public-private market crossover and manager transitions (21:10) Manager evaluation and selection insights (27:46) Investment thesis and building a robust portfolio (33:44) Diversification and trade-offs in manager selection (40:50) Role of absolute return strategies (45:12) Portfolio diversification using MSCI tool (47:12) Career advice and the importance of networking (50:31) Investment process and conviction (50:48) Masterclass on public equity and value investing (51:01) Closing remarks

How can continuation vehicles and independent sponsors unlock structural alpha in private equity when traditional buyouts are struggling with low DPI? In this episode, I go deep with Paul Cohn, Co-Founder and Managing Partner of Agility Equity Partners, on why continuation vehicles (CVs) and independent sponsor deals are reshaping the buyout landscape. Paul explains how CVs let GPs hold their best companies longer while still providing LP liquidity, why the lower middle market offers outsized return potential, and what makes independent sponsors a fast-growing segment of private equity. We cover alignment dynamics, incentives, real-world deal structures, the findings from the HEC Paris study on CVs, and the lessons Paul has learned over 15+ years investing in this niche. Highlights:

• Continuation vehicle market grew from $7B in 2014 to $70B in 2024, with CVs now making up ~15% of PE exits
• Why CVs give GPs a way to hold their best assets longer while still providing LP liquidity
• Positive selection vs. adverse selection in CVs — why diligence is key
• Example mechanics: GPs rolling carry into CVs and LPs choosing between liquidity or rolling capital
• HEC Paris study: single-asset CVs outperformed buyouts on DPI, total value, and dispersion of returns
• Why CVs are less risky: tighter dispersion, better alignment, and GPs investing alongside LPs
• Growth of independent sponsors: ~1,500 in North America, often more deal volume than traditional funds
• Why lower middle market offers more alpha: easier growth, multiple expansion, less competition
• Key lessons from Paul’s career: trust your gut on people, make tough changes quickly

Guest Bio:

Paul Cohn is a Partner & Founder of Agility Equity Partners, responsible for sourcing and executing new investments, monitoring portfolio-company performance, and leading intermediary deal sourcing. Before founding Agility, he was Managing Director & member of the Investment Committee at Fort Washington Capital Partners where he led GP-Led Secondaries investments. He also served as a Partner at Mellon Ventures, Mellon Bank’s private equity affiliate (part of its founding team; over $1.3B invested/committed across 100+ companies & 70+ funds). Paul began his career as an investment manager at Westinghouse Credit Corporation, focusing on leveraged buyouts. He holds a B.S. and MBA from the Tepper School of Business, Carnegie Mellon 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.

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X / Twitter: David Weisburd: @dweisburd

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Paul Cohn: https://www.linkedin.com/in/paul-cohn-841914/

Links Agility Equity Partners: https://www.agilityep.com/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com. (0:00) Preview (1:52) Concerns about dry powder in large buyouts and CV market constraints (3:03) Explanation and incentives for GPs to use continuation vehicles (6:04) Diligence, adverse selection, and transitioning to CVs (10:20) Psychological influences and LP decision-making on CVs (14:42) Attraction of CVs for LPs and alignment of interests (16:54) HEC Paris study and private equity returns impact on CV market (20:55) Evolution of CVs and lower volatility measurement (23:26) Independent sponsor market growth and transition to raising funds (27:22) Single asset CV development in the buyout market (31:11) Allocator concerns and ethics in private equity (36:29) Conflicts of interest in CVs and advice for young investors (42:38) Experiences with underperforming team members and learnable lessons in investing (44:35) Closing remarks

Can venture capital be reinvented to deliver alpha without relying on “heroic assumptions”? In this episode, I go deep with Daniel Kimerling, Founder and Managing Partner of Deciens Capital, on his mission to build a different kind of venture fund—one focused on highly concentrated, long-duration bets in financial services. Dan explains why Deciens is unapologetically “get rich or die trying,” how his team avoids the venture hamster wheel of markups and momentum rounds, and why he believes the next generation of financial institutions (not just fintech apps) will be the true power-law winners. We cover his philosophy on portfolio construction, long timelines, liquidity vs. exits, and how Deciens publishes its playbooks openly to challenge orthodoxy. Highlights:

• Why Deciens aims to be an uncorrelated alpha stream within venture capital
• Radical transparency: aligning with LPs upfront on asymmetric return expectations
• Portfolio construction based on computational simulations; choosing concentration over diversification
• Targeting 10–15 companies per fund, with a model designed to deliver 5x net returns
• The case for financial services as venture’s overlooked mega-sector (20% of global GDP)
• Examples from the portfolio: Chipper Cash, Treasury Prime, Tint Insurance, Sidecar, SimplyWise, Generous Energy
• The “venture hamster wheel” of markups and why Deciens rejects it
• Why liquidity and exits aren’t the same—and why dividends can be just as powerful
• 14-year fund timelines aligned with LPs like pensions and sovereigns that can go long duration
• Deciens as a movement: defying orthodoxy, building with aligned entrepreneurs, and embracing authenticity

Guest Bio:

Daniel Kimerling is the Founder and Managing Partner of Deciens Capital, a first-principles venture firm backed by sovereign wealth funds, endowments, and pensions. Deciens is known for its concentrated focus on financial services—backing both fintechs (like Chipper Cash and Treasury Prime) and next-generation financial institutions (from insurance to asset management). Prior to founding Deciens, Dan co-founded Standard Treasury (acquired by Silicon Valley Bank) and served as GM of API Banking at SVB. A published writer and frequent speaker, he is recognized for challenging conventional VC orthodoxy through essays like Defying Orthodoxy and Betting on Convexity.

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 Kimelring: https://www.linkedin.com/in/dkimerling/

Links: Deciens Capital: https://deciens.com/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com. (0:00) Preview (0:52) Deciens's Capital's investment strategy and portfolio examples (3:00) Deciens's uncorrelated venture strategy and high-risk, high-reward philosophy (5:24) Managing LP expectations with transparency and communication (7:00) Nontraditional portfolio construction and computational simulations (9:45) Process of constructing a portfolio and the conservative approach (14:13) The potential of financial services companies and ecosystem background (20:01) Liquidity strategies and exit planning for non-traditional investments (22:49) Aligning strategy with LPs and venture return competition (26:28) Small fund size counterarguments and the importance of investment asymmetry (29:24) Long-duration investment timelines and compound growth (33:34) Structural alpha advantages and venture fund strategies (38:23) Learnings from closing Fund three and viewing Deciens as a movement (42:04) Pitfalls of traditional venture capital models (46:01) Advice to a younger self on the importance of differentiation (51:28) Creating durable alpha and structural advantages (55:11) The impact of the need for validation on investment decisions (59:21) Aligning firm success with charitable goals and personal motivation (1:01:22) Closing remarks

How can ultra-high-net-worth families invest like endowments—without becoming forced sellers when markets turn? In this episode, I go deep with Greg Brown, Co-CEO of Caprock, on how a modern multi-family office serves UHNW families. Greg explains why Caprock acts as CFO first and CIO second, forecasting liquidity across complex balance sheets before allocating to private markets. We cover the thresholds for when privates make sense, how to structure portfolios for resilience, the role (and limits) of interval funds, and how Caprock uses pooled scale to negotiate economics and secure access to top deals. We also explore tax-alpha strategies like QSBS, Opportunity Zones, and long/short overlays. Highlights:

• Why Caprock takes a CFO-first, CIO-second approach to wealth management
• Liquidity forecasting: mapping every entity, flow, and obligation
• Threshold for UHNW privates: around $10M investable assets
• How full balance-sheet visibility lets families hold more illiquids
• Scale advantages: pooled vehicles with no fees, no carry
• Direct access to elite deals: SpaceX, Anduril, Palantir, Addepar, Anthropic, and more
• Interval funds: where they fit, where they don’t, for taxable investors
• Liquidity buckets: 0–6 months, 6–18 months, and 2+ years
• How to avoid becoming a forced seller in downturns
• Why Caprock buys secondaries 19 out of 20 times
• Tax tools: QSBS, Opportunity Zones, PPLI, 130/30 overlays
• Why privates matter: many top companies now stay private longer

Guest Bio:

Gregory Brown is Co-CEO of Caprock, an SEC-registered multi-family office. Previously, he was an active investor and entrepreneur with experience in product & business development strategy, capital formation, and mergers & acquisitions. He holds a B.S. from the University of Idaho and dual MBAs (Columbia Business School and Haas School of Business, UC Berkeley). Greg is based in Seattle. Outside work he enjoys golf, skiing, cooking, and playing drums in a band. He also serves on the board of La Plaza International.

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/ Gregory Brown: https://www.linkedin.com/in/gregorybrown/

Links Caprock: https://caprock.com/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com. (0:00) Preview (0:24) Negotiating better economics through pooled capital (1:03) Introduction to Greg Brown and Caprock's overview (2:27) Scale, scope, and roles differentiation at Caprock (3:46) Client liquidity needs, cash management, and spending (6:25) Private market investment trends and challenges for high net worth families (9:53) Managing administrative complexity and client cash flows (12:13) Caprock's comprehensive service offerings (13:12) Pooled capital: Advantages, disadvantages, and interval funds (17:53) Cash flow and liquidity management best practices in family offices (20:24) Liquidity issues and solutions in private equity markets (25:33) Secondary market and tax considerations for investors (28:15) Tax loss harvesting, leveraged equity strategies, and private market investment rationale (34:35) Diversification and democratization of private markets (36:45) Opportunities and concerns in private credit and tax planning with PPLI (40:08) Lessons from founding Caprock and scaling venture co-investments (45:56) Closing remarks

How do you run a $1B endowment with a lean five-person team — while balancing liquidity, access, and high-conviction relationships? In this episode, I speak with Geeta Kapadia, CFA, Chief Investment Officer at Fordham University, about how she manages a concentrated portfolio of 30–40 manager relationships, the lessons she’s learned resetting the portfolio for liquidity, and why she favors passive equities with selective active bets in emerging markets and developed ex-US. We also dive into the shortcomings of interval funds, when to say yes to continuation vehicles, and how Fordham leverages the Gabelli alumni network and a student venture fund to extend sourcing and diligence reach. Highlights:

• Fordham’s endowment runs on ~30–40 core manager relationships.
• Portfolio was reset to improve liquidity without losing growth.
• Public equities are passive by default, with selective active in EM and ex-US.
• Interval funds fall short when redemption caps kick in.
• Continuation vehicles: default “yes” on merits, even if committees hesitate.
• DPI is more important than headline IRRs in private markets.
• At $1B, the edge comes from picking well, not chasing mega-funds.
• Building relationships from Fund II to secure later allocations.
• Gabelli alumni and student venture fund boost sourcing and diligence.
• Operator’s mindset: manage fees, portfolio roles, and energy like an orchestra.

Guest Bio:

Geeta Kapadia, CFA is the Chief Investment Officer at Fordham University, where she oversees the school’s ~$1B endowment. Prior to Fordham, she managed ~$5B at a healthcare institution. At Fordham, Geeta focuses on concentrated manager selection, liquidity optimization, and leveraging the university’s alumni and student networks to expand sourcing and talent pipelines.

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/ Geeta Kapadia: https://www.linkedin.com/in/geetakapadiacfa/

Links Fordham University: https://www.fordham.edu/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com. (0:00) Introduction (0:43) Portfolio construction and relationship management at Fordham's endowment (3:17) Leveraging alumni for investment opportunities and fund manager relationships (7:27) Team management and portfolio evolution under Geeta's leadership (12:40) Incorporating semi-liquid interval funds and dealing with fund term extensions (19:29) Evaluating investment performance and transitioning to passive management (27:40) Asset allocation strategies and the role of behavioral finance (32:16) Building GP relationships and aligning with the endowment's mission (38:28) Identifying valuable GP-LP relationships and balancing EQ with IQ (44:33) Access vs. picking in private markets and mid-sized endowment challenges (49:18) Embracing first principles in fund selection and openness to being wrong (52:17) Admitting mistakes and balancing listening with decision-making (55:44) Conclusion and future outlook (56:01) Closing remarks

How do you use the SBIC program to access long-dated, low-cost leverage—without blowing up risk? In this episode, I speak with Eric Rosiak, CEO & CIO of Amplify Community Investment Partners, about the mechanics of SBICs, the new accrual debenture license for venture and growth, what top LPs look for, and how policy changes could expand the opportunity set. We dig into eligibility tests, realistic fund sizes, diligence standards (they’re no joke), and why some large platforms now run SBIC sleeves alongside billion-dollar flagships. Highlights:

• How SBIC leverage works — ~$175M, interest-only over 10 years, priced roughly ~1% over the long-dated Treasuries.
• The 3-prong eligibility test: size (NAICS/employees) or financial thresholds (net worth & income).
• The new accrual debenture license for venture/growth, with Pelion Ventures as first licensee.
• Who’s investing: insurers, foundations, funds-of-funds, plus selective endowments.
• Program changes: leverage and family-of-funds caps, and likely increases under upcoming legislation.
• Big platforms entering via SBIC sleeves (Oaktree, Barings, EIP).
• Strong historical returns: ~16-17% IRR and ~2.3× MOIC.
• Rigorous SBA and GP diligence process. -Tactical advice: structuring LP agreements early to preserve SBIC optionality.

Guest Bio:

Eric Rosiak is the Chief Executive Officer & Chief Investment Officer at Amplify Community Investment Partners, where he focuses on community and economic development strategies and raises capital for SBICs/RBICs and affordable housing funds. He previously held roles at Bank of America, Ocean Tomo, Performance Trust, FBR, and B. Riley, and holds CPA and multiple FINRA licenses.

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/ Eric Rosiak: https://www.linkedin.com/in/ericrosiak/

Links: Amplify Community Investment Partners: https://www.amplifycip.com/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com. (0:00) Introduction (1:33) Understanding the SBIC program and investment criteria (3:15) Target companies and institutional investor types in SBICs (5:46) The role of leverage in SBIC fund performance and growth trends (9:54) Personal and institutional criteria for investing in SBIC funds (14:36) SBA's criteria and the process for accessing SBIC funds (19:20) Challenges for spinouts and first-time SBIC fund managers (22:56) Legislative efforts to impact SBIC investments (26:39) Lessons learned and advice for SBIC industry newcomers (30:02) The significance of leadership in SBIC success (30:52) Closing remarks

What would the bond market look like if it were built today? In this episode, I speak with Dylan Parker, CEO & Co-Founder of Moment, the operating system for fixed income that unifies trading, portfolio construction, and risk/compliance—and automates the workflows wealth platforms run every day. We dig into how fixed income finally went electronic, why half of bond trading still happens by phone or chat, and how Moment can build customized ladders in seconds instead of hours. We also unpack the (surprisingly big) after-tax edge in munis, and Dylan’s lessons from building automated credit trading at Citadel before raising a $36M Series B led by Index Ventures this summer. Highlights:

• Fixed income lags equities—workflows still fragmented.
• ~50% of bond trades still done by phone/chat.
• Smart routing enables millisecond auto-execution.
• Custom muni ladders built in 5–10 seconds.
• Automation drives 25–50× productivity gains.
• LPL ($1.94T AUM) adopted Moment’s OEMS.
• Clients include LPL, Hightower, and fintechs.
• Bonds enable unique tax-loss harvesting benefits.
• $145T fixed income market exceeds global equities.
• Building “ironclad” infra vs. move-fast culture.

Guest Bio:

Dylan Parker is the CEO & Co-Founder of Moment, a New York–based company building the first operating system for fixed income for wealth platforms and institutions. Before founding Moment, Dylan was a quantitative trader/researcher at Citadel Securities, where he and his co-founders worked on automated credit trading. He co-founded Moment with Ammer Soliman (COO) and Dean Hathout (CPO)—a team with deep fixed-income expertise and top-tier engineering that recently closed a $36M Series B led by Index Ventures (with participation from a16z, Lightspeed, Venrock, Neo, and Contrary).

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/ Dylan Parker: https://www.linkedin.com/in/dylan-parker-9b68b3134/

Links Moment: https://moment.com/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com. (0:00) Preview (0:38) Dylan Parker's background and Moment's Series B funding (2:19) Expansion and simplified explanation of Moment's operations (4:40) Citadel's culture, hiring exceptional talent, and trust building (8:53) Current fixed income trading practices and portfolio management (12:30) Trends in tax loss harvesting in fixed income (17:42) High net worth market growth and automation's impact (23:13) Balancing speed and accuracy in financial technology and customer needs (28:10) Hiring opportunities at Moment and David's investment enthusiasm (29:12) Closing remarks

What does it take to build an AI-native search engine for science? In this episode, I spoke with Eric Olson, Co-founder & CEO of Consensus, the platform making peer-reviewed research accessible through AI. We covered the company’s journey from Series A to millions of users, the realities of competing with tech giants, and what truly creates defensibility for AI startups. Eric shared his perspective on the “AI talent wars,” building products at hyperspeed, and what truly creates a moat for AI applications. If you allocate to or invest in AI, you’ll want to hear Eric’s frameworks for product strategy, market sizing, and execution speed. Highlights:

• Consensus as “Google Scholar powered by AI”
• 5M users, ~20-person team, scaling toward Series B
• Funded by USV, Nat Friedman, and Daniel Gross
• Why vertical focus beats horizontal platforms
• The 70/30 framework for product development
• Execution speed as the real moat in AI

Guest Bio:

Eric Olson is the Co-founder & CEO of Consensus, an AI search engine for scientific research founded in 2021 with Christian Salem. Before Consensus, Eric worked in data science at DraftKings and was a Division I football player at Northwestern University. Under his leadership, Consensus raised an $11.5M Series A in 2024 led by Union Square Ventures with participation from Nat Friedman and Daniel Gross.

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/ Eric Olson: https://www.linkedin.com/in/eric-olson-1822a7a6/

Links Consensus: https://www.linkedin.com/company/consensus-nlp/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com. (0:00) Preview (1:03) Series A Celebration and Talent Wars in AI (3:23) Consensus: Overview and Target Users (4:25) TAM for Consensus and Comparison with Google Scholar (8:42) The Edge of Startups in AI and Importance of Focus (15:57) Product Development and Building a Moat in AI (23:01) AI Market Investment Strategies for Asset Allocators (24:36) Fundamentals of Software Investing and Focus on Talent (26:15) Closing remarks

In this episode, I speak with Avy Stein, Founder & Chairman of Cresset—a multi-family office known for its private markets access and co-investing model. We cover Avy’s path from Kirkland & Ellis lawyer to private-equity dealmaker, the Willis-Stein spinout from Continental Bank, why multi-strategy platforms scaled so quickly, how co-invest rights really add alpha (and where adverse selection bites), and the rise of private credit in the middle and lower-middle market. We also get into culture building at scale, how Cresset thinks about alignment with GPs, and Avy’s best career advice from four decades in law, PE, operating, and wealth. Highlights:

• The “scrappy” early days of PE vs. today’s institutionalized playbook (sector teams, QofE, consultants, big ICs).
• Why distribution scale drove the multi-strategy model—and how large allocators should still find differentiated access with megafunds.
• Co-invest alpha math (hat tip Prof. Steve Kaplan) and how to avoid being adversely selected.
• Seeding new vehicles (including GP-stakes/interval-style concepts) and when limited GP economics make sense.
• Private credit today: typical senior-debt returns, leverage levels (lower in LMM), and why sponsor alignment limits downside.
• Culture at Cresset: a written “culture card,” extreme accountability, and hiring for behaviors using assessments plus scenario questions.
• Personal reflections: stepping away during a health battle, building an alt-energy company afterward, and the importance of being present

Guest Bio:

Avy Stein is Founder & Chairman at Cresset, an award-winning multi-family office with over $70B in assets under management (as of July 1, 2025). He previously co-founded and led Willis Stein & Partners (1994) after running CIVC at Continental Illinois; he began his career in 1980 as an attorney at Kirkland & Ellis. Avy holds a J.D. from Harvard Law School and a B.S. in Accounting from the University of Illinois. He also co-founded Lincoln Clean Energy (later acquired by I Squared Capital in 2016).

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/ Avy Stein: https://www.linkedin.com/in/avy-stein-7293251/

Links Cresset: https://www.linkedin.com/company/cresset-capital/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com. (0:00) Introduction (0:06) Avy Stein's early career and transition into private equity (2:45) Evolution of private equity and influence of multi-fund strategies (5:32) Synergies and distribution in private equity and private credit (7:41) Strategies and trade-offs in capital allocation (11:26) Co-investment terms and access in venture capital (15:00) Seeding opportunities, GP stakes, and fund evaluations (17:06) Managing large capital pools and co-investment vehicles (20:08) Aligning GP incentives and building long-term relationships (24:44) Strategy changes, returning capital, and selecting PE firms (28:26) Culture setting, hiring, and opportunities in the lower middle market (35:56) Evolution of lending and private credit for high-net-worth individuals (41:13) Career reflections and advice to younger self (44:17) Key career decisions and building Cresset's value proposition (49:34) Closing remarks

In this episode of How I Invest, I speak with Frank Mihail, CIO of the North Dakota Department of Trust Lands, which manages an $8B sovereign wealth endowment built to fund public schools. Frank shares how his three-person team runs a highly concentrated portfolio with 75% in alternatives, why they prefer evergreen fund structures for liquidity, and how they think about portable alpha, co-investments, and core-satellite strategies. We also discuss the trust’s broader mission: having already distributed $2B to North Dakota schools, with the long-term goal of covering the entire cost of public education. Highlights:

• The origins and purpose of the North Dakota Trust Lands sovereign wealth fund
• How the endowment has grown to $8B in investable assets and $12B total
• Why 75% of the portfolio is in alternatives, including private equity, venture, hedge funds, real estate, and infrastructure
• The case for evergreen fund structures over traditional closed-end vehicles
• Trade-offs between co-investments vs. manager selection for concentrated portfolios
• How portable alpha works in practice—and why North Dakota uses a “portable beta light” approach
• The role of fund-of-funds in reducing operational complexity and building core-satellite strategies
• Behavioral finance and why avoiding mistakes during volatility matters more than chasing marginal alpha
• The trust’s long-term mission to support public schools and reduce taxpayer burden

Guest Bio:

Frank Mihail is the Chief Investment Officer of the North Dakota Department of Trust Lands, where he oversees the investment of the state’s sovereign wealth endowment. Before joining North Dakota, Frank was an Investment Officer at the New Mexico Public Employees Retirement Association (PERA), where he managed hedge fund strategies. He holds deep expertise across public and private markets, with a focus on building resilient, high-performing institutional portfolios.

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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Stay Connected:

X / Twitter: David Weisburd: @dweisburd

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

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com. (0:00) Preview (1:56) Portfolio Construction, Asset Allocation, and Liquidity Strategies (4:45) Evergreen Funds: Benefits and Co-Investment Strategies (10:54) Strategies for Private Equity and Hedge Fund Exposure (18:30) Vanguard's Impact on Indexing and Portable Alpha Explained (23:29) Fund of Funds and Core-Satellite Investment Approaches (29:22) Behavioral Finance in Investment Decision-Making (31:25) Key Investment Thesis and Illiquidity Valuation (36:57) RVK's Role and Economic Impact on Public Education (42:05) Closing remarks

What happens when AI lets five people build what used to take fifty? Can you scale to eight figures in revenue without ever touching a “Series A treadmill”? In this episode, I talk with Henry Shi, co-founder of Super.com and creator of the Lean AI Leaderboard, about seedstrapping (raising once, then reaching escape velocity), outcome-based pricing, and a new, non-dilutive way to finance lean, profitable startups. We also get into how Henry “vibe-coded” an AI VC tool over a weekend, why survival rates should improve in the lean-AI era, and what founder traits show up again and again among these ultra-efficient companies. Highlights:

• Why AI-native teams can hit $10M+ ARR with tiny headcount: lower fixed costs + higher willingness to pay for outcomes.
• Outcome-based pricing beats per-seat SaaS when you deliver measurable business results (example discussed: GrowthX).
• Seedstrapping defined: raise a solid seed round, then avoid the pre-seed→A→B→C treadmill by using capital discipline and AI leverage.
• Henry’s investor model: non-dilutive, non-recourse revenue share structured like a founder-optional line of credit (5–10% of revenue; 2–3× cap).
• Why “reach Series A” is a broken success metric—and why DPI/ongoing cash generation matters more.
• Founder traits that correlate with lean-AI success: repeat builders, high agency, resilience, and comfort going against pattern-matching orthodoxy.
• “Vibe-coding” an AI VC assistant in a weekend: auto-memos, competitor scans, forecasting, and draft term sheets.
• Will YC adapt—or will AI-native incubators centered on seedstrapping emerge? Henry’s take.

Guest Bio:

Henry Shi is the co-founder of Super.com (originally Snaptravel/Snapcommerce), founded in 2016 and rebranded to Super.com in Oct 2022 as the company expanded beyond travel into a savings-focused “super app.” WikipediaPR NewswireSuper Super.com raised $85M Series C in Apr 2023 (over $150M total raised reported at the time). PR NewswireCrunchbase News Henry also launched the Lean AI Leaderboard, tracking ultra-lean, high-revenue AI-native companies; he describes himself as a repeat founder who built a $150M+ annual-revenue startup before “recently exiting.” leanaileaderboard.com He was named to Forbes 30 Under 30 (Consumer Tech, 2019).

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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Sponsor:

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Stay Connected:

X / Twitter: David Weisburd: @dweisburd

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Henry Shi: https://www.linkedin.com/in/henrythe9th/

Links: Super.com: https://www.linkedin.com/company/superdotcom/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com. (0:00) Preview (2:44) AI's Role in Lean High Growth Companies and Outcome-Based Pricing (5:08) Ideal Capital Structure for AI Startups and Venture Capital Challenges (7:53) Seed Strapping and its Suitability for Different Company Types (10:24) Vibe Coding and AI's Potential to Support Diverse Founders (15:26) Founder Characteristics and Incubator Models for AI Startups (18:32) Seed Strapping Investment Model and Fundraising Challenges (23:09) Startup Survival, Revenue-Based Funding, and Success Metrics (30:04) Henry Shi's Fundraising Experiences and AI Startups' Potential (32:52) Infinite Innovation and Encouraging Global Entrepreneurship (34:03) Closing remarks

I had the chance to talk with Francis X. Suarez, the 43rd Mayor of Miami, about how his "open-for-business" leadership transformed the city into a global tech and finance hub. We unpack Miami’s “quantum opportunity,” the practical growing pains—housing, schools, transit—and the civic strategy behind international diplomacy and major sports deals. We also explore his run as President of the U.S. Conference of Mayors and his reflections on leadership, resilience, and embracing failure. Highlights:

• How Miami built an ecosystem so attractive that "companies managing trillions wanted to be here"
• The “quantum opportunity” from migration trends after New York’s November election
• Zoning reforms to boost school capacity, and the housing affordability challenge
• Using Inter Miami’s stadium and star signings (Messi, Busquets, Alba) as civic brand accelerants
• The diplomacy of being "on the ground" in Riyadh during the Gulf trip
• Leadership in the age of mistakes: confidence, humility, and reflection

Guest Bio:

Francis X. Suarez — Mayor of Miami since 2017, President of the U.S. Conference of Mayors (2022–2023), and architect behind Miami’s rise in tech, finance, and global presence. He’s known for civic modernization, bold branding moves, and strategic city-scale 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.

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X / Twitter: David Weisburd: @dweisburd

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Francis X. Suarez: https://www.linkedin.com/in/francissuarez/

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

(0:00) Preview (1:49) Strategies for attracting entrepreneurs and addressing growth bottlenecks (9:14) Advice for political campaigns and US international relations insights (15:04) US-Saudi Arabia relationship and insights from diplomatic trips (21:41) Trump's diplomatic skills and comparison of political career paths (26:30) Personal and psychological insights into President Trump (30:35) Francis Suarez's advice to his younger self and reflections on success (34:45) The role of mindfulness and embracing failure in life (37:21) Closing remarks

Alan Zafran, Founder & Managing Partner at IEQ Capital, joins to unpack how ultra-high-net-worth families and institutions think about risk, cash runways, GP selection, illiquidity, secondaries, LPAC governance, and portfolio strategy amid rising rates and sovereign debt.

-- Highlights:

• The strategic value of a 3–12 month cash runway for risk capacity
• When concentrated allocations (e.g., private credit within IRA) can be intentionally diversified within a larger portfolio
• Why illiquidity premium in private credit demands careful underwriting in a softening market
• Using secondaries to access discounted, high-quality exposure when liquidity is in demand
• Why being opportunistic via marginal reallocations trumps sitting in cash
• GP selection principles: team-first, avoid style drift, manage fund size, and recognize that track records are lagging indicators
• IEQ’s LP governance: securing LPAC seats ~75% of the time to align interests
• Portfolio implications of sovereign debt, rates, and incentives
• Framing crypto (e.g., Bitcoin) as a store of value, if aligned with client preference
• The power of compounding trust in ultra-high-net-worth advisor-client relationships

-- Guest Bio: Alan Zafran is Founder & Managing Partner at IEQ Capital, a registered investment adviser overseeing $41.7B in Regulatory AUM (RAUM) as of June 30, 2025. With a career spanning Goldman Sachs, Merrill Lynch, and Luminous Capital, Alan brings nearly three decades of experience advising UHNW families and institutions. He holds several wealth-advisor recognitions and serves on multiple philanthropic and educational boards.

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

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Alan Zafran: https://www.linkedin.com/in/alan-zafran-0446438/

Links IEQ Capital: https://www.linkedin.com/company/ieqcapital/

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

(0:00) IEQ Capital overview and risk tolerance insights (2:35) Diversification and financial runway importance (6:41) Considerations for client diversification preferences (8:37) Investing in private credit and tax implications (13:05) Assessing the private credit market and opportunistic strategies (21:30) Compounding relationships in wealth management (26:15) Managing capital commitments for ultra high net worth individuals (28:18) Risks associated with single stock loans (31:50) Selecting general partners and vintage considerations (38:19) Relationship and governance with general partners (43:17) National debt impact on portfolio management (49:24) Incorporating crypto into high net worth portfolios (51:45) Staying informed with Alan Zafran and IEQ Capital (52:32) Closing remarks

In this episode I speak with Rafael Costa, who co-founded Across Capital to back category-leading software companies across the U.S. and Latin America. We dive deep on the Brazil tech flywheel — from why the central bank and Pix have accelerated fintech innovation, to the infrastructure winners like QI Tech that are becoming foundational rails for payments, banking and credit. Rafael walks me through Across Capital’s concentrated, high-conviction approach (a ten-company portfolio, deliberate sizing, then backing winners over time), how they underwrite downside protection in growth equity, and what AI actually changes for regulated industries. Along the way he shares practical diligence habits (the “what really matters” slide), how they build conviction over ~17 months, and one piece of advice he’d give his younger self about focusing on the present to compound relationships and learning.

-- Highlights:

• Why Brazil’s fintech moment is real — PIX, an innovative central bank, concentrated incumbents, and huge addressable markets.
• QI Tech: Across Capital’s early/high-conviction relationship with a Brazilian financial-infrastructure platform (Rafael says it was the fund’s first investment and has become a major position). Recent press shows QI Tech reached unicorn status and raised follow-on rounds with General Atlantic; Across Capital participated.
• Why Rafael runs a concentrated, 10-company portfolio — concentration forces clarity, deeper diligence, and the ability to back winners with outsized follow-on checks.
• Underwriting discipline: the “what-really-matters” slide — pick 3–5 drivers, re-underwrite objectively, and size up when the drivers out-perform.
• How AI affects growth equity: less about replacing regulated businesses and more about enabling them (efficiency, automation, product expansion) — attractive for companies in fintech and financial infrastructure.

-- Guest Bio: Rafael Costa is a General Partner at Across Capital, a growth-equity firm that invests in category-leading software businesses across the U.S. and Latin America. Before Across, Rafael worked on growth teams at Vulcan Capital and Summit Partners and started his career in investment banking. Across Capital lists software and growth equity as its core focus and includes companies such as Qi Tech in its portfolio.

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/ Rafael Costa: https://www.linkedin.com/in/rafael-costa-61bb479/

Links Across Capital: https://www.acrosscap.com/

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

(0:00) Introduction (1:34) Evolution of Brazil's tech ecosystem and fintech landscape (6:54) High conviction and concentrated portfolio construction strategies (12:09) Growth equity insights: Consistency, power laws, and sizing strategy (17:53) Institutionalizing investment discipline and exploring market leaders (22:55) AI's impact on growth equity and personal advice for success (27:04) Closing remarks

This episode features John Felix, General Partner & Head of Research at Pattern Ventures, a specialist fund-of-funds focused on backing small venture managers in the $5–50M range. We talk about the endowment principles that shaped John’s investing mindset, how to separate true specialists from résumé-driven narratives, why access and selection are two very different games, and the traps LPs face in co-investments. John also shares lessons on reserves strategy, portfolio construction, and what allocators consistently overlook when evaluating emerging managers.

-- Highlights:

• Why endowments that concentrate in their best ideas tend to outperform—and how that mindset translates to manager selection.
• The real difference between a “specialist” and someone with just a strong pedigree.
• Access vs. selection: most lose the game on access first, here’s how to filter for the best.
• Crawl → walk → run: a stepwise framework for first-time GPs.
• Solo GPs versus partnerships—where each model works and where risks emerge.
• How to think about reserves and portfolio construction in small venture funds.
• Spotting adverse selection in co-invest opportunities.
• Why operator empathy makes for better underwriting judgment.

-- Guest Bio: John Felix is General Partner & Head of Research at Pattern Ventures, where he leads manager selection and research. Pattern Ventures is a fund-of-funds focused on partnering with exceptional small venture funds ($5–50M) and offering co-investment opportunities. Previously, John led Emerging Managers at Allocate and was an investor at Bowdoin College’s Office of Investments under CIO Paula Volent, after earlier roles at an OCIO and Washington University’s Investment Management Company. He holds a BSBA from Washington University in St. Louis.

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/ John Felix: https://www.linkedin.com/in/johnfelix12/

Links Pattern Ventures: https://www.patternventures.com/

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

(0:00) Early career and market efficiency insights (2:02) Scott Wilson as a CIO and manager evaluation process (7:45) Balancing portfolio management with best ideas strategy (17:14) Deep research and the transition to Bowdoin College (23:37) Bowdoin's investment philosophy and Allocate experience (29:03) Founding Pattern Ventures and avoiding LP error (34:32) Early venture investing challenges and strategies (39:00) Venture capital industry bifurcation and fund characteristics (44:05) Mistakes and reserve strategies in venture investing (47:21) Final thoughts and importance of LP-GP partnerships (48:27) Closing remarks

I had the chance to speak with Bradley Tusk, the legendary political strategist turned venture capitalist. He started in politics—running Michael Bloomberg’s mayoral campaign and serving as Deputy Governor of Illinois—before becoming the fixer behind startups like Uber, FanDuel, Lemonade, and Coinbase. Now, he runs Tusk Holdings, where he invests in—and fights for—startups navigating regulation. We talked about his unique investing playbook, how to outmaneuver entrenched interests, what founders misunderstand about politics, and why he’s betting $20 million of his own money on mobile voting.

I had the chance to speak with Bradley Tusk, the legendary political strategist turned venture capitalist. He started in politics—running Michael Bloomberg’s mayoral campaign and serving as Deputy Governor of Illinois—before becoming the fixer behind startups like Uber, FanDuel, Lemonade, and Coinbase. Now, he runs Tusk Holdings, where he invests in—and fights for—startups navigating regulation.

We talked about his unique investing playbook, how to outmaneuver entrenched interests, what founders misunderstand about politics, and why he’s betting $20 million of his own money on mobile voting.

-- Highlights:

• Why he believes every policy output is a political input
• How he helped Uber win political battles across the U.S.
• What makes politicians tick—and how to move them
• Why crypto had a breakthrough 2024 election cycle
• How Tusk Ventures invests in highly regulated industries
• The origin story of the Mobile Voting Project
• When startups should start lobbying—and how to do it effectively
• The one investment he regrets (and what it taught him)

-- Guest Bio: Bradley Tusk is the founder and CEO of Tusk Holdings, which includes Tusk Ventures, Tusk Strategies, and the Tusk Philanthropies foundation. He was formerly Deputy Governor of Illinois and campaign manager for Michael Bloomberg’s 2009 mayoral race. He helped Uber navigate early political battles, taking equity as payment—and then repeated that playbook with FanDuel, Lemonade, Coinbase, and others. He is also the author of The Fixer and Vote With Your Phone, and the founder of the Mobile Voting Project.

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/ Bradley Tusk: https://www.linkedin.com/in/btusk/

Links Tusk Holdings: https://www.tuskholdings.com/

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

(0:00) Introduction (0:44) Strategies for Uber's expansion and political challenges (6:26) Michael Bloomberg's approach and political ROI examples (10:35) Modern lobbying and startup political influence (19:52) Timing for startups to engage in lobbying (22:19) Success and impact of the crypto lobby in elections (25:14) Elon Musk's potential political influence (30:04) Bradley Tusk's mobile voting project and its impact (35:20) Tusk Ventures' investment approach and regulatory appeal (39:51) Perspectives on opposing lobbies and venture capital (42:06) Lessons from investing and politics (43:23) Closing remarks

What does it take to be a truly great limited partner? In this episode, I spoke with Matt Curtolo, a veteran LP who’s worked with some of the most sophisticated institutional investors in the world—Hamilton Lane, MetLife, and Hirtle Callaghan. Today, Matt advises both LPs and emerging GPs, offering a rare perspective from both sides of the table. We dug deep into what separates elite LPs from the pack, how institutional incentives shape decision-making, the paradox of humility and self-promotion among GPs, and why the best partnerships are built on trust, EQ, and long-term thinking. If you're raising a fund—or allocating to them—this episode is a masterclass. Highlights

• Why emotional intelligence (EQ) often separates good LPs from elite ones
• The biggest mistake LPs make: underestimating upside
• How institutional misalignment discourages risk-taking
• What best-in-class co-investment programs actually look like
• How to assess GP conviction without asking directly
• Why emerging GPs struggle—and how Matt coaches them through it
• The real reasons LPs say no (hint: it’s not just returns)
• Why “people first” is Matt’s ultimate investment filter
• A framework for long-term games, trust-building, and kingmaking
• What smaller LPs can do to punch above their weight

Guest Bio

Matt Curtolo is an institutional investor, advisor, and coach with over 20 years of experience across some of the most respected LP organizations in the world. He spent the first seven years of his career at Hamilton Lane, followed by senior roles at Hirtle Callaghan and MetLife. Most recently, he was Head of Investments at Allocate. Today, Matt advises both LPs and GPs on investment strategy, manager selection, fundraising, and co-investments—with a special focus on helping emerging managers navigate the zero-to-one 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/ Matt Curtolo: https://www.linkedin.com/in/matt-curtolo-caia/

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

(0:00) Episode preview (0:11) Experience at Hamilton Lane and early career insights (1:19) Skills and best practices for an elite limited partner (6:15) Leveraging community and referencing in due diligence (10:16) Decision-making, risk tolerance, and LP conservatism (17:16) Characteristics of top-performing LPs and institutional culture (22:03) Advantages and benefits of co-investing for large institutions (27:27) Evaluating co-investment opportunities and GP conviction (32:38) Building relationships with GPs and organizational differences (36:46) Challenges for smaller LPs and quick rejections in GP pitches (42:10) Partnership mentality and long-term industry relations (49:09) Consulting GPs and LPs for a unique perspective (53:09) Common reasons GPs fail to raise money and balancing self-promotion (59:13) The ten-year commitment test and characteristics of emerging LPs (1:03:38) Closing remarks

In this episode of How I Invest, I’m joined by Alex Hormozi — entrepreneur, investor, and founder of Acquisition.com — to unpack the mindset and methods that have fueled his success across multiple industries. We dive deep into why entrepreneurship is more a “game of the heart” than the mind, the power of compounding skills, the dangers of “ignorance debt,” and how to strategically decide whether to build skills yourself or bring in outside talent. Alex shares candid stories from his career — from building gyms to scaling software companies — and offers sharp insights on persistence, focus, and eliminating distractions to win long-term. We also explore the nuances of goal setting, why tiny incremental improvements matter when scaled to millions, and the art of building high-value peer networks. Whether you’re an aspiring founder, seasoned operator, or investor, you’ll walk away with concrete frameworks to increase your odds of success — and the conviction to keep playing the game long enough to win.

-- Highlights:

• Why persistence outperforms raw intelligence in entrepreneurship
• The unseen advantage of being around excellence and winning teams
• How to identify and reduce “ignorance debt” in your business
• The compounding effect of stacking complementary skills over time
• Why patience and focus are the hardest — yet most valuable — entrepreneurial skills
• Building “luck surface area” and increasing your odds of success
• Deciding when to build a skill versus bringing in outside expertise
• Marginal gains at scale: why 2% improvements can move the needle massively
• The ROI framework Alex uses to decide where to spend his time and resources
• Strategic giving and networking: building IOUs that pay off years later

-- Guest Bio: @AlexHormozi Hormozi is an entrepreneur, investor, and philanthropist. With his wife, @leilahormozi Hormozi, he co-founded Acquisition.com, investing in and scaling businesses while sharing their methods through books, podcasts, and media. He’s the author of $100M Offers and $100M Leads, with his new book $100M Money Models launching August 16, 2025.

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

-- Huge Announcement:

Alex Hormozi's newest book, $100M Money Models, launches at a live virtual event Saturday August 16th. Register free: https://register.acq.com

The book will teach you how to get more customers to spend more, in less time, over and over again, ultimately eliminating cash flow as a constraint to growth of any business.

– Stay Connected: X / Twitter: David Weisburd: @dweisburd Alex Hormozi: @AlexHormozi

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

Links Acquisition.com: https://www.acquisition.com/

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

(0:00) Episode preview (1:00) Welcome back, Alex Hormozi and entrepreneurship insights (2:32) Underestimating time for success and skills around excellence (5:40) Learning from higher social status and power dynamics (9:46) Defining ignorance debt and the context of advice (17:27) Compounding skills versus mastering one (24:32) Luck surface area and restarting for cash flow (29:44) Focus as the hardest entrepreneurship aspect (31:17) Levels and characters in the entrepreneurial game (34:54) Tailoring advice to individual entrepreneurs (37:03) Changing behavior and soft skills in older employees (42:14) Preparing for book launch presentations (44:16) Sharing goals publicly and visualization techniques (50:32) Observable actions and career reflections (57:00) Investment regrets and doubling down on successes (1:00:19) Emotional investing challenges and building a mastermind (1:03:36) Networking strategies and bridging creator-investor worlds (1:06:26) Narrowing focus, expanding globally, and AI in deal flow (1:09:00) Transactional relationships and optimal give-to-take ratio (1:14:18) Content leverage and managing time (1:19:15) Initial behavior and relationship efficiency (1:22:21) Communication skills and meeting objectives (1:28:31) Anxiety, performance, and stylistic communication (1:33:25) Entertainment versus education in content creation (1:36:25) Influencing and effectiveness in content (1:39:41) Original content generation and value per word (1:45:45) Independent thinking for success and conviction in investments (1:49:30) Elon Musk's management strategies and leadership vision (1:59:43) High agency challenges and optimizing media production (2:03:51) Solving business constraints and the importance of talent (2:07:48) Closing remarks

Most people pitch performance. Rahul Moodgal built a career on pitching relationships. In this episode, I go deep with Rahul Moodgal—Head of Investor Relations at Parvus Asset Management and one of the most trusted capital raisers in the hedge fund world. Over his career, Rahul has raised $99 billion across platforms like TCI and Parvus, building decades-long relationships with LPs, endowments, and mission-driven institutions around the globe. We explore how Rahul flips traditional fundraising on its head: opening with the negatives, focusing on long-term alignment, and avoiding the sales-y traps that doom many GPs. If you're a manager trying to understand how world-class LPs think—or an allocator looking to work with truly values-aligned capital—this is the playbook.

-- Highlights:

• The Bear Stearns moment that changed everything: Rahul's unconventional pitch that led to 8 out of 12 investors committing capital.
• Why most GPs focus on transactions instead of relationships—and why that's a mistake.
• The difference between asset allocators and asset owners, and why Rahul focuses on the latter.
• How mission-driven capital re-energizes his team and provides a deeper sense of purpose.
• Why duration—long-term relationship building—is the ultimate differentiator in raising capital.
• The secret behind his famous email list and why it's so hard to get on it.
• Parvus’s contrarian investment style: buying when everyone else is selling and holding through the noise.
• Building a 30+ member group of female CIOs to foster collaboration and support.
• Why Rahul goes "analog" in a digital world and still flies thousands of miles for one meeting.
• A clear-eyed framework for distinguishing between “jigsaw” vs. “treasure hunt” LPs.

-- Guest Bio: Rahul Moodgal is Partner, Director of Investor Relations & Business Development at Parvus Asset Management, a London‑based firm specializing in European public equities with approximately $10 billion under management.

With over 25 years of financial services experience, Rahul transitioned into asset management after a period in academia. He studied and taught across four countries—UK, USA, Russia, and Japan—and earned degrees from Keele University, the London School of Economics, and Cambridge University.

Rahul was previously Partner leading Investor Relations & Business Development at The Children’s Investment Fund (TCI), where he became known for setting industry records—including initiating the largest-ever country and sector fund launches within a record timeframe. Following TCI, he advised and partnered with managers across Europe, contributing to firms such as Parvus, TCI New Horizon, KDA Capital, and Algebris Investments.

Beyond finance, Rahul serves as a trustee, board chair, and patron for multiple non-profit organizations in both the UK and U.S., including British Exploring Society, the Sumerian Foundation, Whizz-Kidz, and Scientific Adventures for Girls in Oakland, California

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/ Rahul Moodgal: https://www.linkedin.com/in/rahul-moodgal/

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

(0:00) Episode preview (0:06) Raising $99 billion and Bear Stearns event story (1:46) Changing the pitch strategy and starting with negatives (5:01) Relationship building and quality of capital (10:14) Asset allocator challenges and choosing mission-driven clients (14:32) Role and feedback of LPs in influencing GPs (19:58) David Swensen, Yale model, and LPs pitching value (23:57) Organizational alignment and understanding LPs (27:12) Jigsaw vs. treasure hunt strategies and relationship duration (32:20) Reconciling relationship duration with check size (34:36) Mission-driven investing and non-performance alignment (41:15) Transparency and partnership in investment management (47:02) Long-term relationships versus transactional interactions (50:19) Building personal relationships in the investment world (57:01) Overview of Parvis Asset Management and contrarian strategy (1:02:16) Shorting stocks: Criteria and approach (1:03:48) Rahul Moodgal’s email list and meeting strategies (1:08:02) The value of in-person meetings and flying for deals (1:09:24) Closing remarks

In this episode of How I Invest, I speak with Scott Welch, Chief Investment Officer and Partner at Certuity, a multi‑family office managing over $4 billion in assets. Scott joined Certuity’s Board of Managers in 2020, and now leads the investment strategy and participates actively in risk management across all facets of the firm's investments, including portfolio architecture, asset allocation, investment due diligence, and manager selection We talk about what’s keeping him up at night in public markets, his views on the Fed and interest rate policy, and how Certuity builds globally diversified portfolios that balance risk factor, asset class, and geographic exposure. We also go deep into taxes, where Certuity aggressively harvests losses using market-neutral overlays to create "tax alpha" for their clients.

-- Highlights:

• The logic behind all-weather portfolios—and how they protect investor discipline
• Why 20–25% is the sweet spot for most families in private investments
• How Certuity uses global diversification, risk factors, and asset class tilts
• The rise of market-neutral tax overlays and the case for tax alpha
• A CIO’s view on the Fed, interest rates, and Powell’s successor
• Why Scott is bullish on sports ownership and sailing as an asset class
• How Certuity sources private equity and credit managers—and the role of client networks
• When they’ll use fund-of-funds and when they go direct

-- Guest Bio: Scott Welch, CIMA®, is the Chief Investment Officer and a Partner at Certuity, a $4 billion multi-family office, where he leads the investment strategy team and serves on the Board of Managers and the firm’s risk management committee. He is responsible for portfolio architecture, asset allocation, manager due diligence, and investment decision-making across client portfolios. Prior to joining Certuity in 2020, Scott held senior roles including CIO of WisdomTree’s model portfolios, CIO of Dynasty Financial Partners, and Co-Founder and CIO of Fortigent, a $75 billion investment platform later acquired by LPL Financial. He began his career with over a decade on Wall Street. Scott holds the Certified Investment Management Analyst (CIMA®) designation and certificates in Investment Strategist, Advanced Investment Strategist, and Alternative Investments from the Investments & Wealth Institute (IWI). He has served on IWI’s board of directors, the ABA Wealth Management & Trust Conference advisory board, and the editorial boards of the Journal of Wealth Management and Investments & Wealth Monitor. In 2024, he received the Wealth Management Impact Award from IWI. Scott earned a B.S. in Mathematics from the University of California, Irvine, and an MBA in Finance from the University of Massachusetts at Amherst.

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/ Scott Welch: https://www.linkedin.com/in/scottwelch3/

Links Certuity: https://www.linkedin.com/company/certuity/

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

(0:00) Episode preview (0:05) Concerns in public markets and valuations (1:45) Policy framework, Fed independence, and decision-making (5:21) Fed chair's political influence and market reactions (10:12) Preparing clients for Federal Reserve changes (12:20) Behavioral finance, global diversification, and manager sourcing (18:18) Rebalancing, valuation differentials, and alternatives (22:48) Client preferences and strategies for illiquid investments (29:53) Informational alpha, taxes, fees, and sports team investments (35:40) Approaching private equity and the role of fund of funds (46:49) Streamlining Alt Plus and advice for finance professionals (49:42) AI's impact on careers and investment strategy for the youth (52:03) Best management advice and importance of strong teams (56:00) Educational system's shortcomings and closing remarks (56:57) Closing remarks

Christina Wing is a Senior Lecturer at Harvard Business School, where she teaches the “Family Enterprise” course—a foundational class for the rising generation of family office leaders. She’s also the founder of Wingspan Legacy Partners, where she advises ultra-high-net-worth families on governance, talent, and legacy. In this episode, I sat down with Christina to unpack why most family offices are structurally flawed—and what to do about it. Christina shares insights from advising dozens of families and training hundreds of HBS students from Gen 1, Gen 2, and beyond. We explore the real reason most family offices fail, how to build a high-functioning investment operation, and why separating investment, concierge, and philanthropic functions is critical. Christina also walks me through what makes MSD Capital, the Koch family office, and others stand out—and how the next generation can step up and lead with clarity.

Highlights:

• Why 90% of family offices are structured incorrectly—and how to fix them
• The biggest mistake families make when building a family office
• How the Koch and Dell families have structured their offices for performance
• Why talent is the number one constraint in the great wealth transition
• The critical distinction between cost centers and revenue drivers in family offices
• How to attract top investors to run your family’s capital
• Pay, incentives, and why family offices should behave like professional firms
• The psychological gap between generations—and how to overcome it
• Why Gen 2 and Gen 3 must take ownership and ask the hard questions
• How to align mission, capital deployment, and family legacy
• The future of family offices and why they could outperform other asset classes

-- Guest Bio: Christina Wing is the Founder of Wingspan Legacy Partners, a strategic advisory firm serving families and their enterprises, and a Senior Lecturer at Harvard Business School, where she teaches the Family Enterprise elective. Prior to founding Wingspan, she spent nearly two decades advising operating companies and family offices on leadership, succession, governance, and strategy. Christina is recognized for her work helping multigenerational families navigate the complexities of wealth, purpose, and transition. Her research and teaching sit at the intersection of family dynamics and business performance.

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/ Christina Wing: https://www.linkedin.com/in/christina-r-wing/

Links Wingspan Legacy Partners: https://wingspanlegacy.com/

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

(0:00) Episode preview (2:04) The Koch family's investment and concierge services model (5:24) Managing challenges and team optimization in family offices (7:16) Outsourcing and talent competition in smaller family offices (10:32) Recruitment strategies and pay scales in family offices (17:47) Revenue generation and tactical strategies for family office capital (23:07) Organic vs. fund perspective approaches in family office investments (23:53) Psychological and generational dynamics in family offices (29:18) Responsibility and wealth dynamics across family generations (36:42) The role of failure and resilience in family wealth (38:00) Wealth as an opportunity or a curse (40:33) Fostering proactive behavior in family office generations (44:03) Practical steps for family office success and post-liquidity strategies (47:50) Closing remarks

Why do Harvard and Yale seem to be exiting private equity? What does the most rigorous data actually say about buyout and venture performance? And how should serious LPs think about real estate, hedge funds, and co-investments? In this episode, I’m joined with Steven Neil Kaplan—Professor of Entrepreneurship and Finance at the University of Chicago Booth School of Business, co-creator of the Kaplan-Schoar PME metric, and one of the most widely cited academics in private equity and venture capital. Steve breaks down decades of private market performance data, busts myths around IRRs and overmarking, and gives a rare, honest evaluation of asset class performance through multiple cycles. This conversation is a masterclass in understanding what the real numbers say—direct from the person who helped shape how performance is measured.

Highlights:

• Why Harvard and Yale are selling private equity holdings
• What the best vintages in private equity have in common
• How the Kaplan-Schoar PME and Direct Alpha work
• The truth about buyout returns vs. S&P 500 and Russell 2000
• Steve’s candid take on Ludo Phalippou’s critiques
• Which asset classes he’d avoid if advising an endowment
• What really drives fund overmarking and fundraising timing
• The persistence of venture capital fund performance
• Why co-investing can meaningfully boost LP returns
• Steve’s advice on investing through cycles and downturns

-- Guest Bio: Steven Neil Kaplan is the Neubauer Family Distinguished Service Professor of Entrepreneurship and Finance at the University of Chicago Booth School of Business. He co-founded the entrepreneurship program at Booth and is a research associate at the National Bureau of Economic Research. Kaplan is one of the most published and cited academics in private equity and venture capital, and co-developed the Kaplan-Schoar Public Market Equivalent (PME), a widely used tool for comparing private equity returns to public markets. He has consulted for top private equity firms and advised institutional investors on strategy and fund selection.

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 Neil Kaplan: https://www.linkedin.com/in/steven-kaplan-69594718/

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

(0:00) Episode preview (1:42) Private equity performance vs. S&P 500 and data sources (5:07) Standardization issues and biases in private market data (8:18) Dividend impact and criticisms of private equity metrics (12:03) Predicting future private equity and alternative investment returns (19:34) Correlation between public markets and private equity (22:28) Private equity manager marking practices and customer service importance (29:48) Investor strategies and fee structure implications in private equity (31:51) Comparing large and small buyout market strategies (33:03) Adding value in private equity and challenges in exiting mega deals (37:16) Traits of successful private equity students and investment timing (41:48) Market cycles: Predictions and investment strategies (45:11) Benchmarking venture capital against public markets (47:08) Venture capital performance variability and return statistics (51:13) Closing remarks

What does it take to manage the wealth of America’s most iconic families? In this episode, I spoke with Stephan Roche, Partner at BanyanGlobal, and former senior executive for the Gates and Walton families. Stephan has had a front-row seat to how some of the world’s most sophisticated family offices think about investing, governance, and multigenerational legacy. At Banyan, he now advises enterprising families on ownership strategy and purpose. We explore the frameworks ultra-wealthy families use to structure portfolios, co-invest alongside GPs, and prepare future generations for stewardship—not just of capital, but of mission and values. Whether you’re managing family wealth or building toward it, this is one of the most insightful conversations I’ve had on long-term investing.

Highlights:

• Three dominant family office portfolio models: Yale endowment-style, --Warren Buffett-style, and bespoke/interest-driven strategies
• Why access—not size—is the true edge of large family offices
• The portfolio Stephan would build with $10B: 50–60% private equity, strong values alignment, and multigenerational purpose
• Why starting with estate planning is a mistake—and what to do instead
• Deep dive into private equity vs venture capital, private credit, and co-investing strategies
• How co-invests can boost net returns and “buy down” fund fees
• The importance of GP-level diligence—why it’s not just the fund, but the partner
• Why many family offices are overly focused on wealth instead of impact
• Lessons from “Die With Zero” and how Stephan applied them to a once-in-a-lifetime Gobi Desert trip
• The single best move a G1 wealth creator can make: write a “Letter of Intent” for the next generation

-- Guest Bio: Stephan Roche is a Partner at BanyanGlobal, a leading advisory firm that helps family enterprises govern shared assets and navigate complex transitions. He previously served as Chief Operating Officer of Cascade Investment (the Bill Gates family office) and CEO of Walton Enterprises (the Walton family office). Stephan brings decades of experience advising the world’s most prominent families, and today he helps clients align their values, ownership structures, and governance systems for long-term success

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

We’d like to thank @NordVPN and @Incogni for sponsoring this episode!

#VentureCapital #VC #Startups #OpenLP #assetmanagement

-- Sponsor: NordVPN is one of the fastest and most reliable VPN services available, helping users protect their personal data, block malware, and stay secure on any network. With over 7,000 servers in 125 countries, NordVPN allows investors, travelers, and remote professionals to change their virtual location, access region-locked services, and maintain privacy while working from anywhere. NordVPN believes that strong encryption and seamless connectivity are essential to a secure digital life. EXCLUSIVE NordVPN Deal ➼ https://nordvpn.com/invest. Try it risk-free now with a 30-day money-back guarantee!

Sponsor: Incogni, developed by the makers of NordVPN, is a data privacy tool that helps individuals remove their personal information from the internet. By automatically reaching out to data brokers on the user's behalf, Incogni helps reduce unwanted data exposure, limit spam, and enhance overall digital privacy. Incogni believes that everyone should have control over their personal information in a world where data is constantly being bought and sold. Use code [INVEST] at the link below to get an exclusive 60% off an annual Incogni plan: https://incogni.com/invest.

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

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

Links Banyan Global Family Business Advisors: https://banyan.global/

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

(0:00) Episode preview (1:15) Common investment models and designing a $10 billion portfolio (6:15) Long-term wealth preservation strategies (8:44) Family office commitments vs. pension funds and private equity vs. venture capital (14:10) Tax advantages and fund of funds strategies (19:09) Identifying and partnering with top-performing funds (21:16) Focus on fund of funds and spinouts (23:06) Segmenting emerging managers and co-investment opportunities (27:15) Building relationships with General Partners (GPs) (31:36) Family office dynamics and introduction to Banyan Global (34:34) Secrets to multigenerational wealth management (39:02) Utilizing wealth in service of the family's vision (42:12) Best practices for managing and preserving wealth (45:14) Maintaining perspective and cultivating gratitude (47:50) Insights from "Die With Zero" by Bill Perkins (53:21) Clarifying misconceptions of the Die With Zero philosophy (56:54) Advice for first generation wealth creators (59:59) Closing remarks

Tom Bilyeu went from sleeping on the floor to co-founding and selling a billion-dollar company, Quest Nutrition. Today, he's the force behind Impact Theory, a media studio with a bold mission: pull people out of the Matrix at scale. In this episode, Tom reveals the frameworks that helped him transform from a self-proclaimed “emotionally fragile” dreamer to a high-agency entrepreneur and truth-seeking machine. We cover everything from skill stacking and the physics of progress to first-principles thinking, radical candor in leadership, and how he’s building a real-world version of Ready Player One. If you're obsessed with performance, truth, and high agency thinking, this one’s for you.

Highlights:

• Why skill acquisition—not genius—is the real separator in life and business
• The "physics of progress" framework Tom uses to constantly test, learn, and improve
• How to reframe your ego to build elite teams and attract A+ talent
• The trap of emotion-based decision making—and how to escape it
• Why embarrassment kills more dreams than failure
• What he learned from wasting millions in game development
• Building long-term vision while executing short-term (pragmatic) wins
• His deterministic view on free will—and why he still lives like he has it
• The mindset shift that changed his entire trajectory

-- Guest Bio: TomBilyeu  Bilyeu is the co‑founder of Quest Nutrition, which he helped scale from a startup to a billion-dollar exit in just five years—with 57,000% growth in the first three years alone and reaching a $1 billion valuation by year five. Following that success, he founded @ImpactTheory in 2016, a modern media company focused on empowering audiences through transformative content across YouTube, podcasts, video games, webcomics, and TV/film.

Tom currently serves as CEO of Impact Theory, where he leads a lean yet mission-driven team based in Los Angeles. The studio’s content has amassed approximately half a billion views on YouTube alone and targets spreading a growth‑mindset to millions globally.

Over the past 15 years, Tom has built a personal brand and audience of over 8 million people and has interviewed nearly every high performer in the world. Today, he helps thousands of seven‑figure founders scale to eight figures and beyond.

Tom is a vocal advocate of first‑principles thinking and execution over passion or theory. He regularly shares founder‑level insights, such as running numbers before strategy, framing constraints as competitive advantages, and prioritizing data over narratives.

He holds a degree from the University of Southern California, and though he built Quest Nutrition without an MBA, Tom emphasizes self‑education—often quoting “YouTube is more useful than 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.

#venturecapital #vc #startups #openlp #assetmanagement #tombilyeu #impacttheory #investing

-- Stay Connected: X / Twitter: David Weisburd: @dweisburd Tom Bilyeu: @TomBilyeu

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

Links Impact Theory: https://impacttheory.com/

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

(0:00) Episode preview (2:58) The importance of stacking failures and mapping cause and effect (6:26) Navigating emotions and logical thinking in decision-making (10:39) The truth-seeking algorithm and skill acquisition (17:12) Managing embarrassment and building positive ego (24:21) The mission-driven mindset and long termism in business (33:39) High agency and the role of emotions in leadership (38:38) Passivity versus assertiveness in leadership styles (41:02) Differentiating leadership traits and creating a feedback culture (44:21) The comprehensive debate on free will (46:40) Scientific studies on decision-making (51:03) Accelerated knowledge and the digital age's impact (52:42) Future aspirations, media's role, and America's concerns (54:37) Finding and following guest's work (55:02) Closing remarks

What if your healthcare wasn't about just treating sickness, but maximizing your potential? In today's episode on How I Invest, I spoke with Dr. Cameron Sepah, founder and CEO of Maximus, a performance medicine company pioneering a new paradigm in healthcare. Cameron previously helped build Omada Health, now a billion-dollar public company, and coined the term “digital therapeutics.” Now he's productized his unique medical expertise into a next-gen men's health platform. We talked about the evolution of performance medicine, why testosterone and GLP-1s are changing how Americans manage their health, and how AI is reshaping clinical decision-making. We also dug deep into the personal and systemic failures of the traditional healthcare model — and what the next 10 years will look like as proactive medicine goes mainstream.

Highlights:

• Why traditional healthcare is really a “sick care” system
• What “performance medicine” is — and why it matters
• How Maximus prescribes testosterone and GLP-1s for optimization, not just treatment
• What Cameron learned as founding team at Omada Health
• Why Maximus runs clinical trials when most telehealth companies don’t
• The case for microdosing semaglutide (Ozempic) and GLP-1s
• What most men are missing in their bloodwork — and how to fix it
• The biggest misconceptions around testosterone therapy
• How AI will revolutionize diagnostics, dosing, and coaching
• Why Maximus could only have been built by a psychologist

-- Guest Bio: Dr. Cameron Sepah is the founder and CEO of Maximus, a consumer healthcare technology startup pioneering performance medicine. Before Maximus, he was on the founding team at Omada Health, where he served as Medical Director and coined the term “digital therapeutics.” He is a licensed clinical psychologist, former psychiatry professor at UCSF, and has advised numerous CEOs and venture capital firms on performance and mental optimization.

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

#VentureCapital #VC #Startups #OpenLP #assetmanagement

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

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

Links: Maximus: https://www.maximustribe.com/

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

(0:00) Episode preview (1:32) Lessons from Omada and Publishing Research (5:06) Clinical Trials and GLP-1 Microdosing Strategies (10:07) Insurance Challenges and Personalized Dosing of GLP-1s (14:16) The Future of GLP-1s and Obesity Treatment in America (18:31) Psychological Influences on Obesity and Dietary Choices (21:02) Comprehensive Research on GLP-1s and Weight Management (26:37) Medication Perceptions and Performance Enhancement Debate (30:36) The Role of AI in Advancing Healthcare (35:49) Key Diagnostic Tests for Men's Health Optimization (39:28) The Significance of Routine Blood Testing (41:22) At-Home Blood Testing Innovations (42:35) Turning Personal Expertise into a Scalable Business (43:32) Closing remarks

In this episode, I spoke with Anurag Chandra, Chief Investment Officer of a single-family office and longtime trustee and former Investment Committee Chair of the San Jose Federated City Employees’ Retirement System (FSERS). Over the past decade, Anurag has helped transform FSERS from one of the worst-performing pension plans in the U.S. into a top-decile performer. He’s also an experienced operator, venture capitalist, and accidental allocator—with hard-won insight into everything from re-risking public portfolios to model delivery and tax-loss harvesting. In our conversation, Anurag shared how EQ, team dynamics, and governance structure often outperform raw IQ in investing—and how he helped rebuild a $2.2B pension plan through careful governance reform, luck, and great timing. We also covered how he now applies those same principles at a nimble family office, blending institutional rigor with operational agility.

Highlights:

• Why Anurag believes a 120 IQ and a great network beats a 160 IQ and no network
• The governance overhaul that led San Jose FSERS from bottom-2 to top-decile performance
• Lessons from studying Canadian pension best practices
• How his CIO made a bold move during the March 2020 crash—and why it paid off
• Why he thinks more family offices should behave like institutions
• A breakdown of model delivery, tax-loss harvesting, and custom indexing
• How his operator/investor/allocator background informs his investing philosophy
• Thoughts on emotional intelligence in finance—and why it’s more than a “soft skill”

-- Guest Bio: Anurag Chandra is currently the Chief Investment Officer of a single-family office based in the Bay Area. He previously served for nearly a decade on the board of the San Jose Federated City Employees’ Retirement System, including several years as Chair of the Investment Committee. Under his leadership, the pension plan went from being one of the lowest-performing in the country to a consistent top-decile performer. Anurag has also worked as a venture capitalist, operator, and advisor, with 25+ years of professional experience across legal, investment, and entrepreneurial roles.

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/ Anurag Chandra: https://www.linkedin.com/in/anchandra/

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

(0:00) Episode preview (1:11) The Value of EQ and Resourcefulness in Business (11:40) Anurag Chandra's Career and San Jose Pension Fund Turnaround (19:14) Governance and Manager Selection Challenges in Pension Funds (23:45) Applying Pension Fund Lessons to Family Office Management (26:52) Strategies in Tax Optimization and Asset Allocation (30:05) Model Delivery Concerns in Asset Management (30:58) Integrating Skills for Better Investment Decisions (34:41) Cross-functional Experience and First Principles Thinking (35:05) The Role of a Board Member and Opinion Strength (37:02) Closing remarks

Randal Quarles has been at the helm of some of the most influential institutions in finance and government. From his tenure as Vice Chair of the Federal Reserve and Under Secretary of the Treasury, to his leadership role at The Carlyle Group, Randal brings a rare blend of private market acumen and public sector insight. Today, he's the Chairman and Co-Founder of The Cynosure Group—an investment firm anchored by the Eccles family and built to solve the very structural misalignments that plague private equity for families and foundations. In this conversation, we explore the evolution of private equity, the mismatch between GP incentives and family office needs, the importance of long-duration compounding, and how Cynosure is creating a modern investment firm inspired by the early days of Lazard and Rothschild.

Highlights:

• Why traditional private equity isn’t always aligned with family offices—and how Cynosure is solving that
• The challenges of long-hold investing and how cash-flowing businesses unlock structural advantages
• How Cynosure is organized: six subsidiaries across PE, credit, OCIO, ultra-high-net-worth advisory, hedge funds, and sports investing
• Why Randal prefers growth equity in “unloved” sectors like HVAC and sanitation—rather than chasing tech
• Lessons from working with David Rubenstein at Carlyle and deploying capital through the Great Financial Crisis
• The philosophy behind building an enduring investment firm—and the one piece of advice he’d give his younger self

-- Guest Bio: Randal Quarles is the Chairman and Co-Founder of The Cynosure Group, a Salt Lake City–based investment firm anchored by the Eccles family. He brings over 40 years of experience across financial services, public service, and private equity. Prior to founding Cynosure, he served as Vice Chair for Supervision at the U.S. Federal Reserve, U.S. Executive Director at the IMF, and Under Secretary of the Treasury. In the private sector, he was a longtime partner at The Carlyle Group, where he led its financial services fund.

Randal’s specialties include financial services investing and financial services policy. At Cynosure, he’s built a modern investment firm modeled after the early days of Lazard and Rothschild—designed to meet the structural and tax challenges faced by families, endowments, and long-term investors.

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

#VentureCapital #VC #Startups #OpenLP #AssetManagement.

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

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Randal Quarles: https://www.linkedin.com/in/randal-quarles-4b09788/

Links The Cynosure Group: https://cynosuregroup.com/

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

(0:00) Episode preview (0:06) Private equity funds vs family offices and tax implications (2:10) Evergreen structures, pension funds, and Cynosure Group overview (7:12) Transition to private investments and recruiting challenges (11:07) Cynosure's business structure and growth equity strategies (19:53) Asset class supply and demand dynamics (24:43) Asset allocation framework and sports investing strategies (26:16) Philosophical approaches to team building and recruitment (28:25) Initial impressions of Carlyle's leadership (32:48) Carlyle's Model T approach in private equity (36:02) Deploying a financial services fund during the Great Recession (38:13) Transitioning from law to investing and government influence (41:37) Career advice and investment principles (49:38) Encouraging career flexibility and understanding risk (51:00) Lessons on self-belief and meeting aspirational peers (51:38) The Eccles family's impact on Utah Jazz (52:46) Closing remarks

In this episode of How I Invest, I spoke with Thomas Lee, Co-President and CIO of Parametric, a $600 billion asset manager within Morgan Stanley Investment Management. Tom walks us through how Parametric helps high-net-worth individuals access institutional-quality investment strategies, why customization is the future of asset management, and how their technology powers nearly a quarter million highly personalized accounts. We talk about inflation myths, the credibility of the Fed, and whether the U.S. will eventually inflate its way out of debt. Tom also shares how Parametric brings tax-efficient investing and direct indexing to portfolios as small as $25,000, explains why "investments as a service" is not just a tagline, and offers valuable insights on long-term leadership, scale, and innovation. Whether you're an institutional allocator, wealth manager, or an individual trying to understand the future of investing, this episode is packed with takeaways.

Highlights:

• Parametric manages $600B AUM, accounting for ~37% of Morgan Stanley Investment Management
• Inflation discussion: CPI vs PCE, and why inflation "feels" higher than reported
• The myth of hidden inflation and how CPI is calculated
• Explanation of the Five-Year, Five-Year Forward Rate as a proxy for Fed credibility
• Why Parametric doesn’t try to predict markets—and what they focus on instead
• Delivering customized SMAs down to $25K accounts
• Use cases for tax-loss harvesting, completion portfolios, and values-based overlays
• The evolution of pooled funds to the current era of hyper-customized investing
• Behind-the-scenes on how Parametric runs technology at scale
• Thoughts on active vs passive investing and market efficiency
• The challenge of integrating private alternatives into public portfolios
• Tom’s leadership philosophy: resource allocation, storytelling, and resilient growth

-- Guest Bio: Thomas Lee, CFA is Co‑President and Chief Investment Officer at Parametric, part of Morgan Stanley Investment Management. He joined Parametric in 1994, brings over 30 years of experience, and previously spent two years at the Board of Governors of the Federal Reserve.

As Co‑President & CIO, Tom leads investment teams responsible for research, strategy, portfolio management, and trading, and serves as a voting member on all investment committees. He holds a BS in Economics and MBA in Finance from the University of Minnesota, is a CFA charterholder, and actively engages with the CFA Society of Minnesota.

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/ Thomas Lee: https://www.linkedin.com/in/thomas-lee-97a8826/

Links Parametric: https://www.parametricportfolio.com/

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

(0:00) Episode preview (1:06) Understanding Inflation: CPI and PCE Differences (3:25) Personal and Conspiracy Views on Inflation (6:21) Inflation Coordination and the Five Year Forward Rate (11:39) Tools for High Net Worth Clients in Institutional Finance (14:52) The Rise of Direct Indexing and Its Tax Advantages (17:09) The Shift to Hyper Customization in Finance (23:33) Managing Complexity in Fractional Shares and SMAs (24:51) Customization Strategies for Enhancing Returns (26:25) Debating the Efficient Market Hypothesis (28:16) The Integral Role of a Chief Investment Officer (CIO) (30:38) Communication Challenges within Large Organizations (34:34) Balancing Customer Feedback with Internal Innovation (36:03) Analyzing the Growth of Alternative Investments (41:39) Market Dynamics: Private vs. Public Asset Convergence (42:21) The Relevance of Active Investing in Efficient Markets (44:12) Investment Wisdom: Advice to a Younger Self (47:59) Investment Decision-Making and Contrarian Thinking (51:04) Parametric's Investment Philosophy and Future Plans (52:22) Closing remarks

Nancy Davis spent nearly a decade on Goldman Sachs’ legendary prop desk before founding Quadratic Capital, the firm behind the popular iVol ETF. In this episode, we dive deep into her options-based approach to investing, why she believes most investors manage risk backward, and how her firm is positioning for a potential return of stagflation. We also talk about her early days at Goldman, the psychological traps investors fall into, and why she thinks humility and coachability are underrated superpowers in finance. If you’ve ever wanted to understand volatility, inflation protection, or how to think like a derivatives trader—this episode is for you.

Highlights:

• Starting her career on Goldman Sachs’ Risk Arbitrage desk in the 1990s
• Managing Goldman’s capital like a hedge fund—without client exposure
• Why she avoids stop losses and manages risk upfront using options
• “Debit card investing”: sizing positions by max loss instead of leverage
• Turning the traditional core-periphery portfolio model on its head
• How Quadratic makes options the core strategy, not a hedge
• Lessons from trading during the 2020 oil price shock and SVB crisis
• How the market is not pricing in inflation anymore—and why that matters
• The risks of a stagflationary regime and how iVol is built to respond
• What it really means to be coachable and the power of feedback
• Her most contrarian take on the market going into 2025

-- Guest Bio: Nancy Davis is the founder and managing partner of Quadratic Capital Management and the portfolio manager for the firm’s investment strategies, including the Quadratic Interest Rate Volatility and Inflation Hedge ETF (ticker: $IVOL). Before founding Quadratic in 2013, she spent nearly 10 years at Goldman Sachs, where she was a key member of the proprietary trading desk. Nancy has been recognized by Barron’s and other financial media as one of the leading experts on interest rate volatility, inflation hedging, and options-based portfolio 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: X / Twitter: David Weisburd: @dweisburd

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

Links Quadratic Capital Management: https://www.ivoletf.com/

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

(0:00) Episode Preview (0:59) Differences in trading for internal partners vs. end clients (1:56) Anti stop-loss philosophy and risk management (4:24) Psychological aspects and significant trades in investing (8:41) Discussion on market inflation and lessons from Goldman Sachs (12:58) Importance of mentorship in finance (19:01) Contrarian market perspectives and stagflation explained (20:57) Closing remarks

Mark Wade leads strategy and investments at CAZ Investments, a Houston-based firm managing approximately $10 billion in assets. In this episode, we unpack the evolution of the alternatives landscape, the rise of evergreen funds, and what it means to lead with alignment—starting with $700 million of insider capital invested alongside clients. Mark gives a candid look at how CAZ sources differentiated deals, manages risk through the “CAZ Case” downside model, and builds trust by investing alongside 7,000+ LPs. We also dig into how the firm leverages NAV-based leverage, the growing appetite for alternatives from RIAs, and why humility is essential when allocating capital. If you're an allocator, an advisor, or simply trying to understand where private markets are headed, this episode is packed with insights from one of the most thoughtful voices in the space.

Highlights:

• The origins of CAZ Investments and how it scaled to $10B AUM
• Why Mark believes the RIA channel is the future of wealth advisory
• How CAZ gains access to top-tier deals—and why being the “first call” matters
• Explaining the CAZ Case: their rigorous downside underwriting model
• Why advisors must lead with conviction to retain and win clients
• The mechanics and benefits of NAV-based leverage
• Evergreen vs. drawdown funds—when and why each structure matters
• How alignment of interests drives investment outcomes
• Why top decile managers operate under an entirely different paradigm
• The future of consolidation in private markets and what it means for allocators
• Mark’s view on Tony Robbins becoming a strategic partner and investor in CAZ
• The surprising edge of having 7,000 investors in all 50 states and 36 countries

-- 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 Rice University’s Jones Graduate 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

-- Stay Connected: 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.com.

(0:00) Episode preview (2:09) The growing demand for alternatives in the high net worth space (5:14) Comparing independent advisers and wirehouses (8:21) The rise of alternative investments and regulatory impacts (12:01) CAZ's investment strategy and leveraging funds (19:14) Drawdown vs. evergreen fund structures and management (26:27) Evergreen fund valuation and GP-LP interest alignment (33:53) Encouraging junior team investments and diversified LP advantages (38:47) Building partnerships and obtaining honest references (44:04) Maintaining investment strategy vigor and flexibility (47:00) Trust-building and strategic partnership importance (50:33) Co-investment tactics and humility in due diligence (56:02) CAZ case study on downside protection (59:22) Emphasizing downside protection for sustained success (1:01:01) Navigating game selection in investment strategies (1:03:57) Predicting future trends in private asset markets (1:07:59) Strategic impact of relationship with Tony Robbins (1:10:48) Key lessons from early career experiences (1:13:00) Philanthropy's role in personal and professional success (1:16:29) Building meaningful, long-term relationships (1:19:19) Final thoughts on long-term thinking in market selection (1:19:44) Closing remarks

What if Berkshire Hathaway were built today, with the best of technology and long-term thinking baked into its DNA? That’s the question Matt Foran and his team at StoicLane are answering—by doing it. In this episode, I speak with Matt Foran, co-founder of StoicLane, a holding company quietly building one of the most interesting portfolios in private markets. With over 70 acquisitions across four major verticals—accounting, PEO, appraisal and mortgage services, and vacation rentals—StoicLane now manages $300M in TTM revenue and expects $60M in EBITDA this year. But it’s not just the numbers. StoicLane stands out for its permanent capital structure, seller-friendly integration approach, and deep use of technology and AI to transform old-school industries. We dive deep into how Matt thinks about company building, permanent capital advantages, competing with PE firms, and the cultural flywheels StoicLane is creating as they scale.

Highlights:

• The long-term edge of a permanent holding company
• Why legacy preservation wins deals in fragmented industries
• How StoicLane acquired 71 companies in 3.5 years
• Building the 2nd largest vacation rental platform in the U.S.
• The C-Corp + LLC structure and what it enables
• Aligning every employee with equity ownership
• Using AI to uplevel employees and improve service quality
• Why top talent is the only real constraint
• The tax advantages of evergreen structures
• Lessons from competing with PE playbooks—at a different pace

-- Guest Bio: Matt Foran is the Co-Founder, President, COO, Board Member of StoicLane, a holding company focused on acquiring and transforming real estate and small business service firms using technology and permanent capital. Since launching StoicLane, Matt and his team have completed 71 acquisitions across four major verticals, scaling the platform to $300M in trailing revenue and $60M in EBITDA. Prior to founding StoicLane, Matt built and exited multiple startups in FinTech, real estate, and InsureTech.

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/ Matt Foran: https://www.linkedin.com/in/mattforan/

Links StoicLane: https://www.stoiclane.com/

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

(0:00) Episode preview (0:31) Business scale, acquisitions, and holding company benefits (2:30) Long-term vision in vacation rental business (4:32) Stoic team background and competitive advantages (8:06) Financial outcomes with a unique investment approach (10:27) Business strategies in different verticals (11:26) Proprietary deal flow and acquisition strategy (15:02) Holding company incentives and reverse references (19:33) Commitment fulfillment and long-term relationship building (22:25) Tax benefits of Stoic's business structure (24:18) Capital redeployment and value compounding (26:26) Advantages of evergreen structures (29:14) Utilizing AI in business roll-ups (34:48) Limited use of holding companies in the industry (38:04) Seeking talent for Stoic's growth (40:34) The value of self-sufficiency in employees (42:11) Closing remarks

What’s the playbook for building a resilient, multi-billion‑dollar venture firm that weathers every market cycle? In this episode, Abe Finkelstein, Co‑Managing Partner at Vintage Investment Partners, shares how they underwrite managers, navigate funds‑of‑funds and secondaries, and spot next‑gen innovation—all while maintaining LP confidence across turbulent times.

Highlights:

• How Abe began his career in equity research and transitioned into institutional analysis
• The origin story of Vintage Investment Partners and how it grew to manage over $3B
• Why Vintage operates across fund-of-funds, secondaries, and direct growth investing
• How he evaluates managers and pricing across public and private markets
• What it takes to build long-term trust with LPs in an increasingly competitive market
• Abe’s thoughts on gaming, crypto, and Israel’s next big startup wave
• The decision to relocate to Israel and how that shaped his worldview

-- Guest Bio: Abe Finkelstein is a Co-Managing Partner at Vintage Investment Partners, a global venture platform investing in fund-of-funds, secondary, and direct growth-stage opportunities. Vintage manages over $3 billion across its strategies and partners with leading venture firms and startups globally.

Before joining Vintage, Abe was a Senior Equity Analyst at Goldman Sachs, where he covered Israeli technology companies. He began his career at Brown Brothers Harriman and later served as Vice President at U.S. Bancorp Piper Jaffray. Abe holds a B.S. in Economics from the Wharton School at the University of Pennsylvania, where he graduated magna cum laude.

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/ Abe Finkelstein: https://www.linkedin.com/in/abe-finkelstein/

Links: Vintage Investment: https://vintage-ip.com/portfolio/

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

(0:00) Episode preview (4:03) AI, regulation, and its impact on European venture (7:38) Vintage's investment strategy and focus on emerging managers (12:42) De-risking and advantages of investing in fund ones (23:49) Adapting investment strategies and annual evolution (25:20) Annual off-sites: Key topics and implementing lessons (30:31) Consistency in team across investment strategies (33:06) Generational transfer and firm resilience (37:30) Israel's investment ecosystem and potential peace premium (42:34) Impact of peace on Israeli entrepreneurs and market dynamics (44:43) Advice for aspiring venture capitalists (47:29) Celebrating venture wins and managing the professional-personal balance (48:06) Reflecting on past deals and closing thoughts (48:51) Closing remarks

I spoke with Amy Rubenstein, CEO of Clear Investment Group, about how she built a thriving real estate platform by focusing on one of the most overlooked areas of the market: distressed C-class multifamily housing. Amy didn’t come from institutional real estate — she taught herself everything from Excel to underwriting by reverse-engineering models, and built a company that now serves both high-net-worth and institutional LPs. Today, her firm consistently delivers 30%+ IRRs by stabilizing mismanaged assets and restoring them to market performance. We talk about her journey from buying a single six-unit property to leading a vertically integrated investment platform, her thoughts on risk and inflation, why C-class housing remains resilient, and how she thinks about scaling her team and her impact.

Highlights:

• Why Amy believes C-class multifamily is the most resilient and alpha-rich real estate strategy
• How Clear Investment Group creates value by stabilizing mismanaged assets
• The learning curve of becoming a solo GP with no institutional background
• Amy’s approach to managing and growing a high-performing team
• Her philosophy on impact investing — and why they never needed to label it as ESG
• Institutional fundraising: the 18-month grind and what comes after the first big check
• How her firm stress-tests for interest rate shocks and avoids market speculation
• The strategic vision for a one-stop-shop multifamily investment platform

-- Guest Bio: Amy Rubenstein is the CEO and co-founder of Clear Investment Group, a real estate investment firm focused on distressed, workforce multifamily housing across the U.S. Under her leadership, Clear has grown from small syndicated deals to managing institutional capital and generating 37%+ average IRRs. She has over two decades of experience in real estate investing, is a self-taught operator, and remains deeply involved in every aspect of the firm’s strategy and execution.

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/ Amy Rubenstein: https://www.linkedin.com/in/amy-rubenstein-a0514698/

Links Clear Investment Group: https://www.linkedin.com/company/clear-investment-group/posts/?feedView=all

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

(0:00) Episode preview (1:24) Management and tenant issues in distressed properties (3:02) Amy Rubenstein's industry beginnings and real estate asset performance (5:26) Forecasting interest rates and market conditions (7:59) Interactions with LP base and institutional investors (11:11) Institutional interest and tax benefits in C class real estate (14:07) Essentials of being a successful GP (17:09) Team management and the role of humility (21:22) Delegation, high achievers, and trust (24:19) Growth strategy and future business outlook (26:07) Multifamily real estate and market volatility (29:13) Investment lessons and self-taught skills (33:06) Impact investing and ESG perspectives (35:24) Closing remarks

Philip Krim is best known as the co-founder and former CEO of Casper, one of the fastest-growing direct-to-consumer (DTC) startups in history. Under his leadership, Casper hit $100M in revenue in its first year, went public in early 2020, and was later taken private. Today, Philip is building again—this time through Montauk Climate, a platform innovating in what he calls the “electron economy.” We talked about lessons from hypergrowth, managing through crisis, organizational design, and the future of climate investing.

Highlights:

• How Casper hit $100M revenue in its first year
• Building a brand consumers want to talk about
• What it takes to lead through hypergrowth
• Lessons from taking a company public right before COVID
• Why he believes DTC was just the beginning of a bigger thesis
• What the “electron economy” means and why it matters
• Why Montauk Climate is vertically integrated across venture, credit, and incubation
• How Philip evaluates early-stage founders—and what makes a good bet
• Why portfolio construction is the most underrated concept in venture

-- Guest Bio: Philip Krim is the founder of Montauk Climate and the former co-founder and CEO of Casper. Under his leadership, Casper became one of the most iconic DTC brands in the world, reaching $100M in revenue in its first year and going public in 2020. After exiting Casper, Philip launched Montauk Climate, a platform focused on building and investing in the “electron economy,” with a mix of venture incubation, growth investing, and credit strategies. He is also an active early-stage investor, with early bets in Ramp, MasterClass, and Relativity Space.

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/ Philip Krim: https://www.linkedin.com/in/philip-krim/

Links: Montauk Climate: https://www.montaukclimate.com/

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

(0:00) Episode preview (11:12) Hiring for new skills and functions (16:50) Organizational design for startups (19:42) Task structuring for scalability (20:56) Adapting core beliefs while maintaining credibility (22:21) Data-driven decisions versus gut instincts (23:02) Skills needed for founding a company (26:19) Venture vs. public investors' perspectives (31:09) Introduction to Montauk Climate and its strategy (34:47) Role of credit in energy transition (37:21) Electron economy and incubated companies (50:42) Investment approach for private allocators (53:08) Exploring the electron economy (54:35) Traits of successful early-stage founders (57:16) Predicting investment success challenges (59:35) Portfolio construction in venture capital (1:00:13) Closing remarks

Ron Biscardi is the Co‑Founder & CEO of iConnections, a fintech platform reshaping global capital introduction. With 25+ years in the alternative investment space, Ron has facilitated 36,000+ LP/GP meetings since launching iConnections in April 2020. He previously co-founded a boutique seeding firm, deploying over $600M in capital via 20+ deals. From a philanthropic start—with Funds4Food raising $1.9M in 2020 targeting pandemic relief—to anchoring flagship “Global Alts Miami” events, Ron discusses the strategy of building trust, technology, and community in capital formation.

Highlights:

• From charity event to $50M+ platform in five years
• How 17 crypto managers booked 800+ LP meetings
• The one thing top fundraisers do that others don’t
• Why LP behavior is a better signal than mandates
• The GP playbook for getting 50+ meetings at Miami
• Building a capital platform without raising VC
• What GPs get wrong about post-conference follow-up
• How iConnections is using AI to match funds to allocators
• Why Asia may soon outpace the U.S. in alternatives
• The surprising ROI of dinners, concerts, and long games

-- Guest Bio: Ron Biscardi is the Co-Founder and CEO of iConnections, the leading capital introduction platform for the alternative investment industry. Since launching the company in 2020, Ron has helped scale iConnections from a philanthropic idea during COVID into a global platform facilitating over 36,000 LP/GP meetings and powering flagship events like Global Alts Miami, New York, and Singapore. Under his leadership, iConnections has grown to over $50 million in annual revenue—all without venture funding—and is now used by major industry partners including SALT, CNBC, Forbes, and AIMA. Prior to iConnections, Ron co-founded a boutique seeding firm that deployed over $600 million across more than 20 deals. He’s also the driving force behind iConnections’ charitable initiatives, which have raised over $2.5 million for causes including food insecurity, mental health, and support for Ukraine. Ron holds a degree in Electrical Engineering from Drexel University and has spent over 25 years in the alternative investment industry.

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

We’d like to thank @NordVPN and @Incogni for sponsoring this episode!

#VentureCapital #VC #Startups #OpenLP #assetmanagement

-- Sponsor: NordVPN is one of the fastest and most reliable VPN services available, helping users protect their personal data, block malware, and stay secure on any network. With over 7,000 servers in 125 countries, NordVPN allows investors, travelers, and remote professionals to change their virtual location, access region-locked services, and maintain privacy while working from anywhere. NordVPN believes that strong encryption and seamless connectivity are essential to a secure digital life. EXCLUSIVE NordVPN Deal ➼ https://nordvpn.com/invest. Try it risk-free now with a 30-day money-back guarantee!

Sponsor: Incogni, developed by the makers of NordVPN, is a data privacy tool that helps individuals remove their personal information from the internet. By automatically reaching out to data brokers on the user's behalf, Incogni helps reduce unwanted data exposure, limit spam, and enhance overall digital privacy. Incogni believes that everyone should have control over their personal information in a world where data is constantly being bought and sold. Use code [INVEST] at the link below to get an exclusive 60% off an annual Incogni plan: https://incogni.com/invest.

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

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Ron Biscardi: https://www.linkedin.com/in/ron-biscardi-79063/

Links iConnections: https://www.linkedin.com/company/iconnections-llc/

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

(0:00) Episode preview (1:21) Rahul's approach to adding value to LPs and marketing strategies (7:14) Evolutionary biology, human behavior, and the mission of iConnections (10:35) Founding iConnections and community building (14:22) Compounding benefits of long-term strategies in investing (20:38) Customer feedback, product extensions, and content creation at events (25:24) Leveraging podcast studios for educational value at iConnections events (28:01) Enhancing LP education through meetings (32:41) Relationship building with significant investors (34:31) Effective strategies for GPs to maximize conference opportunities (39:39) Maintaining relationships after conferences (42:45) Impact of AI on manager selection and event planning (47:20) Data partnerships and opportunities (49:16) Addressing misconceptions about iConnections (53:27) Preview of upcoming iConnections events (56:49) Strategies for raising capital across different geographies (59:01) Commitment to expanding into new markets (1:00:44) The role of personal interactions in successful networking (1:02:42) Cultivating friendships to enhance business growth (1:02:58) Closing remarks

In this episode, I speak with Tyler Sosin, founder of Villain Capital, a new fund focused on investing in vertical software businesses. Having grown up in the venture business for 17 years with storied firms Menlo Ventures and Accel Partners, Tyler brings a unique - and perhaps contrarian - perspective to venture investing. With Villain, Tyler's ambition is to help vertical focused founders efficiently scale their start-ups into dominant franchises that can compound their growth and relative market share over decades. The name of the firm, Villain, was inspired by a quote by Harvey Dent, a character in the Batman film The Dark Knight, who said to Batman, “You either die a hero or see yourself live long enough to become a villain.”

Highlights:

• The power of vertical software and markets that start small but grow big
• Characteristics Tyler looks for in early-stage founders
• Misconceptions around TAM and the overlooked upside in niche markets
• Why customer lock-in and annuity-like business models matter
• Thoughts on growth at all costs vs. compounding sensibly
• Lessons from past investments like Flywire, Carta, and Indio
• What venture gets wrong about market sizing and competition
• How Villain balances elements of both VC and growth equity
• The underestimated strength of founders who’ve been burned before

-- Guest Bio: Tyler Sosin is the founding partner at Villain Capital and a board partner at Menlo Ventures. Tyler has a degree in International Relations from Stanford University and lives in New York City.

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/ Tyler Sosin: https://www.linkedin.com/in/tylersosin/

Links: Menlo Ventures: https://menlovc.com/team/tyler-sosin/

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

(0:00) Episode preview (1:37) Peter Thiel's perspective and the role of market power (5:12) Identifying potential villain companies in early stages (8:26) Successful strategies in product bundling and market control (12:44) Venture capital approach to small markets (19:11) Balancing growth and sustainability in startups (24:56) Historical impact and profitability of tech giants (27:37) The importance of collaborative thinking and networking in VC (31:03) Herd behavior and innovation in fund management (34:53) Vertical software companies: PE and growth equity interest (37:23) Debunking market size myths in startup success (42:36) Storytelling and scaling in startup growth (44:15) Strategies for expanding market reach in growth companies (48:56) Career advice from Tyler Sosin's perspective (51:00) The Thiel fellowship's influence on young entrepreneurs (51:40) Closing remarks

In this episode, I speak with T.C. Wilson, Chief Investment Officer of The Doctors Company (TDC Group), the nation's largest physician-owned medical malpractice insurer with $7 billion in assets under management. T.C. shares how he built an internal investment office, how insurance investing differs from endowment and foundation models, and why he treats surplus like an endowment portfolio. We dive into his framework for portfolio construction, his views on innovation in asset management, the underrated value of evergreen structures, and the specific ways GPs can tailor their approach to win over insurance LPs. T.C. also shares why he’s cautious on large-cap private equity, how he thinks about downside protection, and what extreme ownership has taught him as a leader. If you want to learn how a CIO with decades of experience invests across public and private markets with an eye toward solvency, surplus growth, and long-term resilience, you’ll want to listen to this one.

Highlights:

• T.C.’s path from Mercer to CIO of TDC Group
• Building an internal consulting-style investment team
• What makes insurance companies unique LPs
• Why surplus is treated like an endowment portfolio
• Portfolio construction: 80% non-VAR, 20% “fun stuff”
• How to think about investing as a taxable entity
• The role of rated feeder notes in optimizing statutory reporting
• What GPs often get wrong when pitching insurance allocators
• Evergreen structures and the “virtue of illiquidity”
• Why culture and leadership matter more than most realize

-- Guest Bio: T.C. Wilson is the Chief Investment Officer of The Doctors Company (TDC Group), where he oversees more than $7 billion in assets under management. He joined the firm in 2017 after serving as an external investment consultant to the company for 18 years. Prior to TDC, T.C. worked at Mercer and led an institutional consulting group focused on insurance clients. He has over 35 years of experience in investment management and is known for his deep understanding of how to balance surplus growth, solvency, and risk-adjusted returns within the insurance framework.

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/ Thomas (T.C) Wilson: https://www.linkedin.com/in/thomas-t-c-wilson-ab70b7a/

Links: TDC Group: https://www.tdcg.com/

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

(0:00) Episode preview (2:15) Capital allocation: Insurance vs. Endowments & $3.2 billion surplus impact (4:52) Tax considerations in portfolio construction (6:06) Traits of successful GPs and regulatory support (10:22) Rated feeder notes and attracting insurance investors (14:31) Evolution of asset managers and TDC Group's current strategy (20:35) Private equity insights and evergreen fund benefits (25:50) Investment strategy for downturns and portfolio resilience (30:34) Illiquidity's role and criteria for new PE manager investments (33:12) Portfolio construction vs. manager selection debate (37:38) General partners' practices and AI's future impact on asset management (42:11) Investor and allocator perspectives: Overrated and underrated aspects (45:12) Extreme ownership and its influence on company success (49:29) The significance of principles and culture in firms (50:09) Conclusion and contact details (50:19) Closing remarks

What does it take to allocate billions in private markets—and what sets a top-tier LP apart? In this episode, I speak with Patrick Miller, Executive Director and Portfolio Manager of J.P. Morgan Asset Management’s Private Equity Group, where he plays a central role in their alternatives platform, investing across venture capital and private equity. Patrick shares how a single energizing meeting with a Florida-based venture capitalist sparked his interest in the asset class and how his team has since built a differentiated barbell strategy combining legacy tier-one firms and new emerging managers. We dive into what LPs can do to truly add value to GPs, why fund size and ownership matter, how AI is shifting capital dynamics, and what makes a venture firm truly “differentiated.” Whether you're a founder, a new VC, or an allocator, this episode is full of real LP insights from one of the most thoughtful voices in the game.

Highlights:

• How Patrick first got excited about venture capital (and why he still is)
• What LPs bring to the table beyond capital
• The three most important differentiators for emerging managers
• Why J.P. Morgan Asset Management venture strategy uses a barbell approach
• The effect of AI on venture capital’s capital stack
• How small funds can outperform big ones—if you know what to look for
• What Patrick looks for in private equity managers
• The most important advice he’d give his younger self

-- Guest Bio: Patrick Miller is an Executive Director and Portfolio Manager of J.P. Morgan Asset Management’s Private Equity Group, where he is responsible for portfolio management, investment due diligence, and business development. He joined J.P. Morgan in 2012 and has played a key role in sourcing and managing investments across venture capital, private equity partnerships, co-investments, and secondary opportunities. Patrick earned his BA from Northwestern University, where he studied Communications and Business Institutions and was a member of the varsity baseball team.

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/ Patrick Miller: https://www.linkedin.com/in/patrick-miller-80386558/

Links: J.P Morgan Asset Management: https://am.jpmorgan.com/us/en/asset-management/institutional/investment-strategies/alternatives/private-equity-group/

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

(0:00) Episode preview (0:06) Patrick Miller's entry into venture capital and adding value as an LP (3:01) Stability and institutional experience in venture capital (4:36) Investing in emerging managers and conviction in their success (9:06) Impact of AI on venture capital (13:28) Examples of backed managers and investing in private equity (20:35) Advice for new investors and closing thoughts (22:37) Closing remarks

Michael Marvelli leads the private markets strategy at the UCLA Investment Company, managing a portfolio that spans private equity, real estate, and real assets. But his route to institutional investing wasn’t linear. Before UCLA, he spent time at Prudential and The Irvine Company in real estate and mortgage finance, and even helped launch a venture-backed startup as COO and CFO. That operating experience gives him a unique lens when evaluating managers today. In this episode, we talk about how UCLA builds conviction in lower-middle-market GPs, how they manage dry powder and fund pacing, and what it was like spinning out UCLA’s investment office into an independent entity.

Highlights:

• The origins of the UCLA Investment Company
• What it took to build the team, processes, and governance from scratch
• Why UCLA is drawn to undercapitalized and underfollowed private equity managers
• How real estate and real assets fit into a long-term endowment portfolio
• The importance of downside protection and flexible pacing in private markets
• How being a startup COO informs his view on GP talent, decision-making, and alignment
• What he looks for in truly “great” allocators and investors

-- Guest Bio: Michael Marvelli is the Deputy Chief Investment Officer of the UCLA Investment Company, where he leads the firm’s private markets strategy, overseeing private equity, real estate, real assets, and credit. He joined UCLA in 2003 and played a key role in the 2011 launch of the UCLA Investment Company.

Before joining UCLA, Michael worked in real estate and mortgage finance at Prudential and The Irvine Company, and co-founded a venture-backed startup where he served as COO and CFO. He holds a BS from UC Berkeley’s Haas School of Business and an MBA 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.

#VentureCapital #VC #Startups #OpenLP #assetmanagement

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

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Michael Marvelli: https://www.linkedin.com/in/michael-marvelli-9918557/

Links: UCLA Investment Company: http://www.uclainvestmentcompany.org/home

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

(0:00) Episode preview (1:46) Evolution of UCLA Investment Company's strategy (2:29) Asset allocation and its impact on returns (4:11) Manager selection vs. asset allocation strategy (7:30) Exploring the lower middle market in private equity (15:54) Challenges for endowments investing in the lower middle market (20:55) Specialization and focus in endowment investment strategies (25:50) Independent sponsor deals and search funds insights (29:59) Portfolio construction and commitment strategies (32:54) Investment deployment in the lower middle market (34:37) Value creation strategies in lower middle market investments (38:45) The influence of interest rates on private equity (40:56) Defining the ideal GP in private equity (44:03) The importance of sector specialization and operating executives (50:12) Founder-operator rapport in the lower middle market (54:54) Career advice for aspiring private equity professionals (58:34) Emphasizing first principles in investment strategy (1:02:48) Michael Marvelli's strategic thinking and personal strengths (1:04:30) Closing remarks

David Berry is one of the most prolific healthcare entrepreneurs of our time. In this episode, we discuss his transition from scientist to founder to investor, what it takes to scale transformational health companies, and how his firm Averin is helping usher in the next wave of AI-enabled healthcare. We also talk about his early experience launching a satellite at 14, how he's co-founded over 30 companies—including seven unicorns—and why patents, perseverance, and purpose are the trifecta behind lasting innovation.

Highlights:

• “The Elon Musk of Biotech?” Why Sorov called David that—and how David approaches world-changing problems
• From 0 to 7 Unicorns: What David looks for in the first year of a company that signals long-term greatness
• Pivots vs. Distractions: How to recognize the “kernel of truth” that transforms strategy
• The Power of Culture: Why early-stage hiring is make-or-break—and how his brother built an elite culture at TripleLift
• Replacing Founders Is Overrated: How world-class companies scale with visionary founders still at the helm
• Extreme Passion: The real signal that a team will stay late, even without being told
• The Investor’s Edge: Why early and mid-stage inflection points are where true multiples are made
• Averin Capital: His new firm focused on tech-driven health companies in the underserved growth stage
• The Coming Wave in Alzheimer’s: Why he believes personalized medicine will finally unlock real progress
• Product-Market Fit in Biotech? Why 60% of approved drugs still lose money—and how to avoid those pitfalls

-- Guest Bio: David Berry is the Managing Partner and co-founder of Averin, a Boston-based investment firm focused on helping build the next generation of great technology-powered healthcare companies. Prior to Averin, he was a General Partner at Flagship Pioneering, where he co-founded over 30 ventures across life sciences and sustainability—including seven that became unicorns. He holds an M.D. from Harvard Medical School, a Ph.D. in Biological Engineering from MIT, and a B.S. in Brain and Cognitive Sciences from MIT. David is also the recipient of numerous honors, including MIT Technology Review’s Innovator of the Year and World Economic Forum Young Global Leader. He is the inventor on over 200 patents and helped launch a satellite at age 14.

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 #biotech #assetmanagement

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

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

Links Averin: https://www.averincapital.com/

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

(0:00) Episode preview (3:21) Drive, perseverance, and strategic pivots in entrepreneurship (7:25) Company culture and founder roles during growth and scaling (15:09) Identifying entrepreneurial superpowers and inner circle support (17:23) Transitioning from entrepreneur to investor principles (21:29) Growth investing strategies and investor-management alignment (25:43) Navigating biotech's business and financial challenges (32:36) Skill stacking and venture capital dynamics in biotech (37:30) Closing remarks

In this episode, I speak with Rip Reeves, CEO of Institutional Investor and former CIO of AEGIS Insurance Services. Rip brings over four decades of experience across investment management, insurance, and endowments. We discuss his unconventional path from Salomon Brothers to leading one of the most iconic platforms in the investment world, his views on the OCIO model, portfolio construction, the “art” of manager selection, and why he believes building authentic relationships matters more than ever in this industry. We also cover his deep ties to LSU, how he uses qualitative signals (like waiting room conversations) in manager evaluations, and the future of Institutional Investor in a changing GP-LP landscape.

Highlights:

• Why LSU’s endowment chose the OCIO model with Cambridge Associates
• Rip’s view on optimal allocation for endowments — and why 40/30/30 isn't as rigid as it looks
• The surprising importance of culture and hallway conversations when vetting asset managers
• How Institutional Investor uses experiential events (like raft races) to build real trust
• Rip’s perspective on how the public vs. private market divide is blurring — and what that means for allocators
• Why fixed income is “back” for the first time since the GFC
• The hidden value of his wife Susie’s honest feedback in his investment thinking
• The one thing GPs should never do at an Institutional Investor event

-- Guest Bio: Rip Reeves is the CEO of Institutional Investor, a leading global platform serving allocators, asset managers, and consultants through content, community, and convenings. Before joining II in 2023, he spent over 11 years as CIO and Treasurer of AEGIS Insurance Services. Prior to that, Rip was Global CIO of Argo Group and held senior roles at BNY Mellon Asset Management, J.P. Morgan Investment Management, and Salomon Brothers.

Rip serves on the LSU Foundation Board, teaches finance at LSU, and is an advisor to Northern Trust Asset Management and Preferred Mutual. A Louisiana native, he holds a B.S. in Marketing and an MBA from Louisiana State 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/ Rip Reeves: https://www.linkedin.com/in/rip-reeves-1b725717/

Links: Institutional Investor: https://www.linkedin.com/company/institutional-investor/

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

(0:00) Episode preview (5:27) Importance of portfolio construction over manager selection (11:23) Qualitative factors and company culture in manager selection (21:59) Building relationships with asset managers (24:58) Rip Reeves on Institutional Investor magazine's impact and event value (31:33) David Weisburd's closing remarks and subscription call-to-action (36:37) Best practices for GP and LP relationship building (41:55) Touch points and allocations between GPs and LPs (44:18) Leveraging Institutional Investor for GP benefits (45:36) Learning about Institutional Investor with Rip Reeves (46:01) Closing remarks

John Trammell has been on the front lines of institutional investing for decades. He’s managed capital for some of the largest families and organizations in the world—from family offices to the Episcopal Church—and in this episode, he explains the seismic shifts happening in the world of endowment and foundation investing. We talk about secondaries, collateralized fund obligations (CFOs), the future of Bitcoin in institutional portfolios, and why concentration—not diversification—created most of the great fortunes. This is one of the deepest conversations I’ve had on how the smartest long-term investors are thinking today.

Highlights:

• Why top endowments are dumping assets in the secondary market
• How secondaries give institutions a way to clean up bad manager exposure
• The real reasons endowments need liquidity today
• Why some schools are now selling private equity... to themselves
• What a collateralized fund obligation (CFO) actually is
• Why John believes we’re past the Swensen model—and what’s next
• The truth about diversification (and when it fails you)
• How to build conviction to survive the toughest market moments
• Why cash is no longer a drag on portfolios
• How to cultivate a “prepared mind” for the next black swan event

-- Guest Bio: John Trammell is a seasoned institutional investor who has managed assets across public and private markets for decades. He currently leads investments for the Episcopal Diocese of New York and has previously managed portfolios for prominent family offices and foundations. John is known for his thoughtful, experience-driven approach to asset allocation, governance, and long-term investment strategy—and for his ability to distill complex ideas into timeless lessons.

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/ John Trammell :https://www.linkedin.com/in/john-trammell-258723/

Links: Episcopal Diocese of New York: https://dioceseny.org/

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

(0:00) Episode preview (3:11) Liquidity and portfolio construction in university endowments (5:26) Pros and cons of secondary fund investments (7:09) Secondary market investment mistakes by institutional investors (9:20) Asset quality tiers in secondary investing (10:04) Execution of collateralized fund obligations (13:02) Investment governance and alumni contributions (19:54) Swenson model evolution and diversification strategies (25:14) Portfolio management: Concentration vs diversification (28:06) Assessing portfolio diversification strategies (30:15) Bitcoin's role in portfolio diversification (32:27) Cash and emotional challenges in investing (35:18) Tactical strategies during market downturns (36:23) Conviction's importance in investment decisions (39:06) Institutional views on Bitcoin allocation (51:13) Educating stakeholders on liquidity management (54:06) The importance of investment education (55:38) Embracing a prepared mind in investing (57:43) Closing remarks

Aaron Jacobson is one of the most insightful thinkers at the intersection of AI, robotics, and cybersecurity—and in this conversation, he separates signal from noise. We explore the future of humanoids, the shifting threat landscape in cybersecurity, and why the next wave of industry-defining companies will be built on infrastructure, not just foundation models. Aaron Jacobson is a Partner at NEA, where he invests in AI, cybersecurity, and cloud infrastructure. He’s backed companies like Databricks, Horizon3.ai and Veza, and previously worked in tech M&A at Qatalyst Partners. In this episode, we dive into what’s real vs. hype in AI, the future of humanoids, and where the biggest opportunities in infrastructure are emerging.

Highlights:

• Why Elon’s humanoid prediction is “off by multiple orders of magnitude”
• What’s missing for humanoids to move from hype to real-world deployment
• The 3 biggest challenges in robotics—and why they’re so hard to solve
• How open models vs. closed models will shape the future of AI value capture
• Why NEA is doubling down on cybersecurity
• What cyber threats will look like in 5 years (spoiler: it's terrifying)
• Why pen testing and “exposure management” are the future of security
• How AI agents could close the gap between defenders and attackers
• What Aaron learned working with Frank Quattrone at Qatalyst
• How NEA thinks about multi-stage investing and the future of venture

-- Guest Bio: Aaron Jacobson is one of the most insightful thinkers at the intersection of AI, robotics, and cybersecurity—and in this conversation, he separates signal from noise. We explore the future of humanoids, the shifting threat landscape in cybersecurity, and why the next wave of industry-defining companies will be built on infrastructure, not just foundation models.

Aaron Jacobson is a Partner at NEA, where he invests in AI, cybersecurity, and cloud infrastructure. He’s backed companies like Databricks, Horizon3.ai and Veza, and previously worked in tech M&A at Qatalyst Partners. In this episode, we dive into what’s real vs. hype in AI, the future of humanoids, and where the biggest opportunities in infrastructure are emerging.

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/ Aaron Jacobsob: https://www.linkedin.com/in/aaronejacobson/

Links: NEA: https://www.nea.com/

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

(0:00) Episode preview (4:18) Safety and industrial applications of humanoids (9:01) Breakthroughs and acceleration in humanoid development (9:38) Value capture in LLM ecosystems and Facebook's LAMA strategy (14:04) Cybersecurity trends: ransomware and penetration testing (17:23) AI's impact on cybersecurity and role of insurance (20:30) Preventative cybersecurity measures and multifactor authentication (25:48) Closing remarks

In this episode of How I Invest, I speak with Arjun Sethi—Chairman and co-founder of Tribe Capital, Co-CEO of Kraken, and one of the sharpest thinkers in venture capital and crypto today. Arjun breaks down how he approaches investing in “N-of-1” companies, what most VCs get wrong about data, and why the traditional funding stages like “pre-seed” and “Series A” are being rewritten in real time. We also go deep into Arjun’s frameworks for scaling world-class companies, the evolution of crypto in a changing political landscape, and the big bets he’s making at the frontier—including humanoid robotics. Whether you're an allocator, founder, or just fascinated by the future of finance, this conversation is packed with sharp insights and original thinking.

Highlights:

• Why Arjun views Tribe as an “operating system” for venture
• What makes Kraken different from Coinbase and Binance
• The critical difference between a market leader and an N-of-1 company
• How Arjun uses leading indicators to invest ahead of revenue
• The vision behind Termina, Tribe’s in-house data platform
• What most investors get wrong about benchmarks
• How tokenized equities could reshape global capital markets
• Why humanoid robots could play a key role in defense and logistics

-- Guest Bio: Arjun Sethi is the Co-Founder and Chairman of Tribe Capital, a venture capital firm managing $1.8 billion across stages. He is also the Co-CEO of Kraken, one of the world’s largest crypto exchanges. Arjun previously worked at Facebook, was a partner at Social Capital, and has founded multiple companies across consumer, enterprise, and deep tech. Most recently, he incubated Foundation Robotics, a humanoid robotics company building toward a future of self-sustaining 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.

#VentureCapital #VC #Startups #OpenLP #AssetManagement

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

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

Links Kraken: https://kraken.com/ Tribe Capital: https://tribecap.co/

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

(0:00) Episode preview (1:06) Differentiation of Kraken from other exchanges and crypto trading evolution (6:00) Investing strategies: n of one companies vs market leaders (8:00) Advancements in data utilization for early-stage investments (11:47) Applying nuanced metrics to traditional and tech companies (16:16) Knowing your market position and strategic growth (18:23) Focus and product development in top companies (20:13) Vertical integration trends in various sectors (22:25) Strategies for competing with large venture firms and staying private (27:33) Tokenization in venture capital (29:49) Foundation Robotics: Mission and challenges (32:54) Future of humanoid robots in industry and defense (33:19) Closing remarks