How I Invest with David Weisburd

Latest Episodes:

E203: How Elite Endowments Invest w/John Felix Aug 22, 2025

Show notes

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

E202: The Startup Lobbying Playbook w/Bradley Tusk Aug 20, 2025

Show notes

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.

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

E201: Top 10 Things LPs Look for in a General Partner w/Matt Curtolo Aug 18, 2025

Show notes

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

E200: 21 Harsh Truths Nobody Will Ever Tell You - Alex Hormozi Aug 15, 2025

Show notes

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

E199: How Rahul Moodgal Raised $99 Billion by Playing the Long Game Aug 13, 2025

Show notes

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

E198: How Family Offices Construct Portfolios in 2025 w/Scott Welch Aug 11, 2025

Show notes

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

E197: Why Most Family Offices Fail—7 Lessons from Harvard Professor Aug 08, 2025

Show notes

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

E196: Professor Steve Kaplan: Do Privates Really Outperform the S&P 500? Aug 06, 2025

Show notes

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

E195: 7 Lessons on Family Office Investing w/Stephan Roche Aug 04, 2025

Show notes

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!

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-- 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

E194: From Broke & Sleeping on the Floor to a $1 Billion Exit w/Tom Bilyeu Aug 01, 2025

Show notes

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

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