How I Invest with David Weisburd
How I Invest with David Weisburd is a podcast that interviews the world's leading institutional investors. Previous guests include The Ford Foundation, Northwestern University Endowment, CalPERS, Stepstone, and other top limited partners.
Episodes
E419: Venture Capital Has a Liquidity Crisis
Venture capital was designed around a relatively simple model: invest in a startup, help it grow, and eventually exit through an acquisition or IPO.
David sits down with Benjamin Black Powerlaw Corp. (Nasdaq: PWRL), Akkadian Ventures, Ben invests in growth-stage technology companies while providing alternative liquidity to founders, employees, angel investors, and venture funds.
In this episode,
E418: AI, Venture Capital & the Future of Investing
Most venture firms think AI is another productivity tool.
David sits down with John Melas-Kyriazi co-founder and CEO of Standard Metrics—the AI-native portfolio management platform used by leading venture capital and private equity firms—to discuss how AI is transforming every stage of investing, from sourcing and diligence to portfolio management, follow-on decisions, and firm operations.
John
E417: $20B Investor on Risk, Uncertainty & Adaptability
Most investors spend their careers trying to eliminate risk.
David sits down with Alec Litowitz the founder of Qstar Capital, founder and former CEO of Magnetar Capital, and one of Citadel's earliest partners to explore the difference between risk and uncertainty, why adaptability is becoming the world's most valuable skill, how elite investors make decisions when there is no model to follow, an
E416: Ares Investor on Data Centers, Investing Moats & Lessons Learned
Why do the largest investment firms keep getting bigger?
David sits down with Joel Holsinger, Co-Head of Ares Alternative Credit, to discuss why scale has become one of the biggest competitive advantages in investing, how Ares evaluates multi-billion-dollar opportunities, why data centers and AI infrastructure are reshaping private credit, and how great investors think about downside protection.
E415: Why Every VC Is Suddenly Investing in Defense
For years, defense investing was considered off limits for most venture capital firms.
Today, billions of dollars are flowing into defense startups as AI, drones, autonomy, advanced manufacturing, and national security become some of the biggest investment themes of the decade.
David sits down with Jake Chapman, Managing Director at Marque Ventures, to discuss why defense became mainstream, how
E414: How LPs Evaluate GPs in the AI Era
For decades, fundraising was driven by relationships. Today, it increasingly starts with AI.
David sits down with Lex Suvanto, Global CEO of Edelman Smithfield, to discuss how artificial intelligence is changing fundraising, why reputation is becoming one of the most valuable assets for investment firms, how GPs can differentiate themselves in an increasingly crowded market, and why authentic tho
E413: How AI Will Reinvent Venture Capital
Most venture firms are experimenting with AI. Footwork rebuilt the entire firm around it.
David sits down with Nikhil Trivedi, Co-Founder & General Partner at Footwork, to explore what an AI-native venture capital firm actually looks like, how autonomous agents are changing sourcing, diligence, portfolio management, and investment decisions, and why judgment and relationships may be the last true
E412: UPENN Endowment: Why AI Will Create a New Generation of PE & VC Firms
AI isn't just changing technology—it is reshaping how investment firms create value, evaluate managers, and generate alpha.
David sits down with Thomas Scriven, Managing Director University of Pennsylvania Office of Investments, institutional investor with experience across private equity, endowment management, and investment banking, to discuss why AI-native investment firms may outperform tradi
E411: How AI Is Creating a New Generation of Venture Firms
Most venture firms are using AI to save time. Earlybird is using it to generate alpha.
David sits down with Andre Retterath, General Partner at Earlybird, to discuss how his firm built an AI-native venture platform, why proprietary data is becoming venture capital's biggest competitive advantage, how machine learning improves investment decisions, and why the future of venture belongs to investor
E410: How Relationships Built a $3.6B Venture Firm
Consumer startups may grab the headlines, but some of the most valuable companies are built by solving mission-critical problems for businesses.
David sits down with Rick Heitzmann, Managing Director at FirstMark Capital, to discuss how he identifies high-growth technology-enabled business services, why sectors like data infrastructure, compliance, marketing technology, and information services c
E409: The Leadership Lessons That Built a $6.5 Billion Firm
Most investors chase what's exciting. Jason Koenig built a $6.5 billion firm by investing where almost nobody was looking.
In this conversation, Jason explains why overlooked industrial assets can produce exceptional long-term returns, how ITE grew from $60 million to $6.5 billion in assets under management, why culture compounds just like capital, and the leadership lessons he learned while scal
E408: HarbourVest: Why Venture Capital Is Chasing Trillion-Dollar Companies
Venture capital isn't about avoiding losses. It's about owning the handful of companies that change everything.
Scott explains why HarbourVest has built its venture strategy around power laws, why secondaries have become essential to modern venture investing, and how institutions evaluate managers, partners, and companies across thousands of investment opportunities.
E407: Why Venture Capital is Becoming a Winner-Take All Market
Venture capital has never been more competitive. Aram Verdian argues it has also never been more concentrated.
Drawing on Accolade Partners' research across more than 3,000 U.S. venture firms, Aram explains why fewer than 20 firms have consistently produced 3x net returns, what separates the firms that keep winning, and why venture is increasingly becoming a winner-take-all business. From portfoli
E406: Why AI Won't Transform Most Enterprises for 10 Years
Most companies use AI to make employees slightly more productive. Sushanth Raman believes AI should do the work instead.
As the CEO of Pallet, Sushanth is building an AI workforce for the $12 trillion logistics industry, helping carriers, brokers, freight forwarders, and shippers automate mission-critical operations inside the systems they already use. He explains why reasoning-driven AI represen
E405: Why AI Has Made Venture Capital Harder (Not Easier)
The best venture investors don't just identify great markets. They recognize exceptional founders before everyone else does.
Michael Gilroy shares lessons from investing at Coatue, Microsoft's M12, Battery Ventures, Insight Partners, and now Marathon Management Partners. He explains what separates extraordinary founders from everyone else, how venture investors evaluate conviction versus consensu
E404: Why This Billionaire Family Office Doesn't Rebalance Its Portfolio | Pincus Family CIO
Most investors obsess over pre-tax returns. Scott Abookire argues they're measuring the wrong thing.
As Chief Investment Officer of Pincus Capital, Scott oversees globally diversified public and private portfolios for multi-generational families. In this conversation, he explains why after-tax returns are the metric that truly matters, why he abandoned the traditional endowment model, and how sop
E403: Why the Best Investment Firms Stay Small | Sound Point Capital Founder
Most investors believe raising more capital is always a sign of success. Stephen Ketchum has spent nearly two decades proving the opposite.
As Founder, CEO, and CIO of Sound Point Capital, Stephen built a $46 billion credit platform by resisting one temptation that destroys investment firms: deploying capital simply because it's available. Instead of maximizing assets under management, Sound Poin
E402: $92B Coatue: Where the Value in AI Will Accrue
Everyone is asking which AI company will win. Lucas Swisher thinks investors are asking the wrong question.
The biggest opportunities won't necessarily come from picking a single model or application. They'll come from understanding where durable advantages are created across the AI stack. Drawing on Coatue's investments in companies like OpenAI, Anthropic, Databricks, and SpaceX, Lucas explains
E401: Einstein Was Wrong About What Actually Compounds
After more than 400 conversations with investors, founders, CIOs, and capital allocators managing over $10 trillion, the tables finally turn.
In this special episode, Curtis Pierce, Co-Founder of Weisburd Pierce and the How I Invest podcast, interviews host David Weisburd about the biggest ideas that have permanently changed his thinking.
David argues that the greatest compounding force isn't ca
E400: Anthony Pompliano on Power Laws, Conviction, and Compounding
Most investors spend their lives searching for more ideas. Anthony Pompliano thinks the real money comes from finding the rare idea and refusing to let go.
Across public markets, private markets, Bitcoin, startups, and careers, Anthony argues that value follows power laws: a tiny number of companies, people, and decisions drive almost everything. The hard part is not effort. It is recognizing dur
E399: How General Catalyst Finds Billion-Dollar Startups
Most investors assume that once a venture firm reaches $43 billion in assets under management, the real opportunities shift toward writing larger checks.
Yuri Sagilov believes the opposite.
General Catalyst continues to push deeper into seed because that's where investment themes are born, founder relationships are formed, and category-defining companies are first recognized. Rather than optimiz
E398: Hamilton Lane ($1T AUA) on Venture Capital, AI, and Private Markets
What separates the venture investors who consistently outperform from those who simply get lucky?
In this episode, I sit down with Miguel Luina, Co-Head of Global Venture Capital at Hamilton Lane, to discuss how one of the world's largest private markets investors evaluates venture managers, constructs portfolios, and thinks about the future of innovation investing. Miguel explains why venture an
E397: Why Venture Capital Is a Relationship Compounding Machine
What if the greatest edge in venture capital isn't having the biggest fund—but building the strongest relationships?
In this episode, I sit down with Elizabeth Weil, Founder and Managing Partner of Scribble Ventures, to discuss how emerging venture firms can outperform by staying focused, collaborative, and relentlessly founder-centric. Elizabeth shares how she built Scribble into a $280 million
E396: The Future of Compute, Data Centers, and AI
What if AI's most valuable commodity isn't software—but the computing power that makes intelligence possible?
In this episode, I sit down with Kush Bavaria, Co-Founder and CEO of Ornn, to discuss why AI compute is becoming the next global commodity and how financial markets are evolving to support it. Kush explains why GPU capacity should trade like oil or electricity, how derivatives and futures
E395: Russ d'Sa on AI, Agents, and the Future of Work
What happens when computers stop being tools and start behaving like collaborators?
In this episode, I sit down with Russ d’Sa, Founder and CEO of LiveKit, to discuss why voice AI may become one of the most important computing platforms of the next decade. Russ explains how LiveKit powers AI experiences for companies including Tesla and xAI, why voice is emerging as the natural interface for AI a
E394: How Great LPs Pick Venture Funds | Jamie Rhode
What if the biggest mistake LPs make in venture is backing the same managers over and over instead of constantly asking who they would invest in if they were starting from scratch today?
In this episode, I sit down with Jamie Rhode, Partner at Screendoor, to discuss what separates the best emerging managers from the rest of the market. Jamie explains why so many venture funds look identical today,
E393: What 8,000 LPs and GPs Taught Him About Investing | Ron Biscardi
What if the biggest edge in investing isn’t information, strategy, or even intelligence—but relationships?
In this episode, I sit down with Ron Biscardi, Co-Founder and CEO of iConnections, to discuss what separates the world’s best allocators and investment managers from everyone else. Ron shares lessons from building the largest capital introduction ecosystem in alternatives, with more than 26,
E392: Jason Pritzker on Family Offices, Venture Capital, and Long-Term Investing
What if the secret to building generational wealth isn’t finding the perfect investment—but finding the right people and holding great businesses for decades?
In this episode, I sit down with Jason Pritzker, Managing Director and Vice Chairman of The Pritzker Organization and founder of 53 Stations, to discuss the investing principles that helped shape one of America’s most successful business fa
E391: $17 Billion CIO on Taxes, Private Markets, and Building Wealth
What if the biggest driver of long-term investment success isn't finding better investments, but helping investors avoid their own worst decisions?
In this episode, I sit down with Ron Albahary, Chief Investment Officer at LNW, to discuss the unique challenges of managing wealth for taxable investors and why portfolio construction is as much about psychology as it is about finance.
E390: Ron Rofé on AI, Founder Obsession, and Venture Returns
What if the best venture investors aren’t chasing the hottest sectors—but the founders who would still be working on the problem long after the hype disappears?
In this episode, I sit down with Ron Rofé, Co-Founder and General Partner of Rainfall Ventures, to discuss why founder quality matters more than industry trends, how non-consensus investing creates outsized opportunities, and what he has
E389: The Future of Investing: Data Centers, AI & the Next Trillion-Dollar Companies
What happens when one investor sits at the intersection of venture capital, natural resources, AI, space infrastructure, and geopolitics?
In this episode, I sit down with Rob Stephens, Director of Investments at Spider Management, to discuss how institutional investors are adapting to a world where private markets are capturing more value, AI is reshaping capital allocation, and the boundaries be
E388: The Future of Investing: AI, Expert Networks, and Information Alpha
What if the biggest edge in investing today isn't having more information—but knowing how to turn information into conviction?
In this episode, I sit down with Matt Wells to discuss how AI is reshaping the investment process, why investors are drowning in data but starving for conviction, and where information alpha still exists in increasingly efficient markets. Matt explains the evolution of ex
E387: Where Alpha Hides in Private Equity | Josh Adams
What if the best private equity opportunities are hiding inside businesses that everyone else thinks are too complicated to touch?
In this episode, I sit down with Josh Adams, Partner at OpenGate Capital, to discuss why complexity has become one of the firm's greatest competitive advantages. Josh explains how OpenGate built a specialization around corporate carve-outs, why Europe offers more inef
E386: Adams Street ($70B): Venture Capital Has a New Problem
What separates the venture investors who generate extraordinary returns from those who simply participate in the asset class?
In this episode, I sit down with Jeff Diehl, Managing Partner and Head of Investments at Adams Street Partners, one of the world's largest private markets investors with more than $70 billion in assets under management. Jeff shares lessons from over four decades of venture
E385: Why Public Markets Need SpaceX, OpenAI & Anthropic
What if the biggest opportunity in private markets isn’t finding the next startup—but owning the next public company years before it ever rings the bell?
In this episode, I sit down with Matt Witheiler, Head of Late-Stage Growth at Wellington Management, to discuss how the line between public and private markets continues to blur. Matt explains why companies are staying private longer, why public
E384: CEO of Commonfund on Venture Capital, Power Laws & the Future of IPOs
What if the biggest edge in venture capital isn’t manager selection—but earning access to the managers everyone already knows are the best?
In this episode, I sit down with Mark Anson, CEO, President, and CIO of Commonfund, to discuss what he has learned managing capital across some of the world’s most influential institutions, including CalPERS, the Bass Family Office, and Commonfund. Mark expla
E383:Why the Next Fortune 500 Companies Will Be Built on AI
What if the biggest investment opportunity of the next decade isn’t AI itself—but the companies building the infrastructure and workflows that allow AI agents to actually do work?
In this episode, I sit down with David Blumberg, Founder and Managing Partner of Blumberg Capital, to discuss why he believes agentic AI is still in the first inning of a multi-decade transformation. David explains how
E382: Why Venture Capital Has a $3 Trillion Liquidity Problem
What if the biggest opportunity in venture today isn’t finding the next unicorn—but solving the liquidity problem created by companies staying private twice as long as they used to?
In this episode, I sit down with Ravi Viswanathan, Founder and Managing Partner of NewView Capital, to discuss how the venture ecosystem is evolving beyond the traditional fund model. Ravi explains why he left NEA to
E381: A16Z Partner: The Tax Strategy Hidden Inside Real Estate
What if the biggest inefficiency in investing today isn’t asset selection—but the fact that most investors still optimize for pre-tax returns instead of after-tax outcomes?
In this episode, I sit down with Jeff Bramel, Partner at a16z Perennial, to discuss why real assets remain one of the most misunderstood areas of institutional investing. Jeff explains how structural diversification works beyo
E380: How Billionaire Family Offices Actually Invest
What if the greatest threat to generational wealth isn’t bad investing—but the inability to think beyond the next liquidity event?
In this episode, I sit down with Eric Becker, Founder and Chairman of Cresset, to discuss why he built a modern multi-family office after decades as an entrepreneur and investor. Eric explains the structural conflicts inside traditional wealth management, why most ult
E379: Why Great Investment Firms Eventually Stop Performing
What if the biggest problem in asset management today isn’t investment performance—but misalignment between managers and the investors they serve?
In this episode, I sit down with Luke Sarsfield, Chairman and CEO of Ridgepost Capital, to discuss how incentive structures shape long-term outcomes in private markets. Luke explains why Ridgepost leaves most carried interest with underlying managers,
E378: Why LPs Keep Selling Their Highest-Quality Funds
What if the biggest opportunity in private equity today isn’t buying companies—but buying liquidity from investors who are forced to sell great assets for reasons unrelated to performance?
In this episode, I sit down with Ryan Levitt, Co-Head of LP Secondaries at ICG, to discuss why secondaries have evolved into one of the most attractive areas in private markets. Ryan explains how LP secondaries
E377: Midas List VC: Why Most VCs Miss the Biggest Companies
What if the biggest venture returns are already gone by the time a category has a name?
In this episode, I sit down with Niko Bonatsos, Founder and Managing Partner of Verdict, to discuss why the best venture opportunities emerge before consensus exists. Niko explains why “50% of the profits are made before a vertical even has a name,” how he identifies “freak” founders with extreme rates of lear
E376: The $3 Trillion Liquidity Problem in Venture Capital
What if the biggest opportunity in venture today isn’t funding new companies—but solving the liquidity crisis created by companies staying private for 20 years?
In this episode, I sit down with Jared Carmel, Founder and Managing Partner of Manhattan Venture Partners, to discuss how venture secondaries evolved from a gray market into critical infrastructure for private capital markets. Jared expla
E375: Why Tax Alpha Could Matter More Than Investment Returns
What if the biggest source of alpha for taxable investors isn’t stock picking—but minimizing friction inside the portfolio itself?
In this episode, I sit down with Brent Sullivan, independent tax analyst and author of one of the leading research platforms on tax-aware investing, to discuss why tax alpha has become one of the fastest-growing themes in wealth management. Brent explains how long-sho
E374: Why the Best Investors Prepare for Crashes Before They Happen
What if the key to outperforming isn’t taking more risk—but building a portfolio strong enough to survive volatility without breaking?
In this episode, I sit down with Doug Hanly, CIO of the Louisiana State Police Retirement System, to discuss why liquidity, simplicity, and process are the foundations of durable investing. Doug explains why he views short-term government credit as the “supply dep
E373: What Most CIOs Get Wrong About Alpha
What if the best investment opportunities are the ones most investors avoid because they’re too hard, too small, or too inefficient to pursue?
In this episode, I sit down with Raphael, Deputy CIO and Co-Leader of HighVista Strategies, to discuss the concept of “beautifully inefficient” markets and why durable alpha often exists where few investors are willing to spend time. Raphi explains how gov
E372: Why the Best Venture Investments Look Wrong Early
What if the best venture investments come from ignoring consensus and trusting your own taste before the market catches up?
In this episode, I sit down with Maya Bakhai, Founding Partner of Spice Capital, to discuss how cultural intuition, narrative cycles, and conviction shape venture investing. Maya explains how working with Kevin Durant at 35 Ventures gave her access to top-tier deal flow whil
E371: Midas List VC: Why AI Models Will NOT Become Commodities
What if the biggest winners in AI won’t come from having the best model—but from building the strongest feedback loops around users?
In this episode, I sit down with Hans Tung, Managing Partner at Notable Capital and longtime Midas List investor, to discuss how decades of investing across consumer internet and global technology shaped his thesis around AI. Hans explains why Anthropic stood out ea
E370: What Taxable Investors Still Get Wrong About Returns
What if the biggest source of alpha today isn’t stock picking—but structuring portfolios more intelligently after taxes?
In this episode, I sit down with Shang to discuss why tax alpha is becoming one of the most important themes in wealth and asset management. Shang breaks down how long-short tax-aware strategies work, why manager selection matters more than most investors realize, and how inves
E369: Midas List VC: Why Smart VCs Are Buying Secondaries
What if the best opportunities in venture today aren’t in new deals—but in existing companies right before an inflection point?
In this episode, I sit down with Ryan Moore, Founder of Revenant VC and longtime venture investor, to discuss why he made the shift from primary venture investing to secondaries after more than two decades in the industry. Ryan explains how longer liquidity timelines are
E368: Sovereign 2.0: How Mubadala Capital Is Reinventing the $430B Playbook w/CIO Oscar Fahlgren
The biggest edge in private equity is finding deals by going where others won't.
In this episode, I sit down with Oscar Fahlgren, Chief Investment Officer of Mubadala Capital, to discuss how embracing complexity and scale creates asymmetric opportunities in global private markets. Oscar explains why large, complex deals often have less competition, how Mubadala Capital uses its balance sheet to a
E367: The Family Office Betting on Humanity’s Future
What if the highest-return investments are the ones that reshape the future—not just the ones that fit today’s market?
In this episode, I sit down with L.R. Fox, Managing Director of NEXT Global Capital, to discuss why he rejected the traditional path of “build wealth first, give later” and instead built a strategy around impact from day one. Fox explains why capital is a vote for the future, how
E366: Keri Findley: The Credit Investor Peter Thiel Chose to Back
What if the best investments aren’t the riskiest—but the ones everyone else can’t own?
In this episode, I sit down with Keri Findley, Founder and CEO of Tacora Capital, to discuss how she built one of the most differentiated credit strategies by focusing on illiquidity, not risk. Keri explains how dislocations are often driven by forced sellers and structural constraints, why the best credit oppo
E365: Stanford GSB Professor on Venture Capital’s Manager Incentives
What if the biggest mistake in venture investing isn’t picking the wrong fund—but misunderstanding incentives and behavior?
In this episode, I sit down with Ilya Strebulaev, Professor of Finance and Private Equity at Stanford GSB, to discuss how incentives, biases, and portfolio construction shape outcomes in venture capital. Ilya explains why fee structures matter less than how they’re designed,
E364: $90B Limited Partner: Why We're (Still) Bullish on Large VC Funds
What if venture capital isn’t an asset class—but an access game where only a few managers matter?
In this episode, I sit down with Nolan Bean, CIO at FEG Investment Advisors, to discuss how institutional investors are adapting to a world where companies stay private longer and AI is reshaping every asset class. Nolan breaks down why access to top-tier managers matters more than allocation, how ve
E363: How Nigel Morris Built QED into a Fintech Powerhouse
What if the real edge in venture capital isn’t picking companies—but helping them survive long enough to matter?
In this episode, I sit down with Nigel Morris, Managing Partner at QED Investors and Co-Founder of Capital One, to discuss how fintech innovation actually happens and why most investors misunderstand the role of venture capital. Nigel explains why incumbents struggle to innovate despit
E362: Why Jensen Huang Believes Physical AI will be a $50 Trillion Market
What if the biggest opportunity in AI isn’t intelligence—but the missing data layer for the physical world?
In this episode, I sit down with Daniel Jacker, CEO and Co-Founder of ZaiNar, to discuss why physical AI could become a $50 trillion market and the infrastructure required to make it work. Daniel explains how turning wireless networks into a real-time sensing layer unlocks entirely new capa
E361: Why Venture Capital is Not an Asset Class
What if venture capital isn’t really an asset class—but a game where only a handful of managers actually matter?
In this episode, I sit down with Ian Sigalow, Co-Founder and Managing Partner of Greycroft, to discuss why venture returns are driven by a small group of firms with consistent access to the best companies. Ian explains why diversification often hurts venture outcomes, how the industry
E360: The Hardest Lessons I Learned from Building 4 Unicorns
What if the biggest breakthroughs in biotech don’t come from more capital—but from building better systems for innovation?
In this episode, I sit down with Errik Anderson, biotech entrepreneur and founder behind multiple billion-dollar companies, to discuss how building infrastructure, not just drugs, is reshaping the future of healthcare. Errik explains why most biotech companies fail the same w
E359: What Charlie Munger Taught Me About Venture Capital
What if the real edge in venture isn’t price—but who you choose to partner with for a decade?
In this episode, I sit down with Jamie Montgomery, Co-Founder and Managing Partner of March Capital, to discuss how long-term relationships, not transactions, drive venture outcomes. Jamie explains why asymmetric upside matters more than negotiating the last percentage point, how conviction and disciplin
E358: The Woman Behind the World's Top GP Brands | Jen Prosek
What if the biggest edge in investing isn’t capital or strategy—but how clearly the world understands you?
In this episode, I sit down with Jennifer Prosek, Founder and Managing Partner of Prosek Partners, to discuss how branding, narrative, and communication have become core drivers of success in financial services. Jennifer explains why firms went from ignoring marketing to depending on it, how
E357: CalSTRS CIO: Where Do You Invest $390 Billion Today?
What if the biggest edge in managing $390 billion isn’t picking assets—but controlling risk and liquidity when markets break?
In this episode, I sit down with Scott Chan, Chief Investment Officer of CalSTRS, to discuss how one of the largest institutional investors in the world is positioning for a period of massive structural change. Scott breaks down how AI, deglobalization, and the energy tran
E356: Why Co-Investments Are Taking Over Private Equity
What if the next source of alpha in private equity isn’t funds—but individual deals?
In this episode, I sit down with Rohan Parikh, Vice President at Houlihan Lokey, to discuss the rapid rise of co-investments and why they are becoming a core part of institutional portfolios. Rohan explains how extended fundraising cycles, larger deal sizes, and slower distributions have created a “perfect storm”
E355: From Deal-by-Deal to a $6.5B Platform: Building a Real Estate Investment Empire
What if the best investments aren’t found in chaos—but in having the discipline to act when others can’t?
In this episode, I sit down with Darren Fisk, Founder of Forum Investment Group, to discuss how he scaled from early syndication deals to a fully integrated multifamily investment platform managing billions. Darren breaks down how he leaned in during the 2008 financial crisis to acquire 9,000
E354: Why Most VCs Misunderstand Peter Thiel’s Power Law
What if venture capital isn’t about finding unicorns—but about consistently making good investments?
In this episode, I sit down with Eric Scott, Co-Founder and Managing Partner at Overlook Capital, to discuss how his approach to venture evolved from chasing power laws to focusing on fundamentals. Eric explains why most venture frameworks only make sense in hindsight, how thinking like a value in
E353: Why Biotech Is Struggling in Today’s Market (and the Future of Healthcare)
What if the biggest opportunity in healthcare isn’t new drugs—but reinventing how the entire system works?
In this episode, I sit down with David Berry, Founder of over 20 companies including seven $1B+ businesses, to discuss why the traditional biotech model is breaking and where the next wave of innovation in healthcare is emerging. David explains how pricing pressure, rising costs, and global
E352: JD Vance’s Co-Founder on Space Defense, Hard Tech, and the Biggest Opportunities Ahead
What if the best venture returns come from avoiding trends—not chasing them?
In this episode, I sit down with Colin, Co-Founder of Narya, to discuss how he approaches investing in frontier sectors without falling into mimetic behavior. Colin explains why the best opportunities are often “hidden in plain sight,” how mission-driven investing can still generate venture-scale returns, and why concent
E351: Why Most Family Offices Fail (And How a16z Fixed It)
What if the biggest edge in investing isn’t picking better assets—but structuring them better for taxes, incentives, and control?
In this episode, I sit down with Michel, Founding CIO of a16z Perennial, to discuss how institutional investing frameworks translate to individual portfolios. Michel breaks down why most wealth management fails at true investment management, how misaligned incentives s
E350: How Family Offices Quietly Build Generational Wealth
Is the real edge in investing not picking assets but structuring how you allocate capital?
Terence Thompson is a Vice President of Investments at DF Enterprises, about how single family offices think about portfolio construction, liquidity, and structural alpha. We break down why Terry uses a total portfolio approach, how family offices create edge through flexibility, and why being a liquidity p
E349: Built to Scale: The J.P. Morgan Growth Playbook
What if the biggest edge in venture today isn’t picking companies—but owning the entire lifecycle of capital?
In this episode, I sit down with Paris Heymann, Co-Managing Partner of Technology Investing at J.P. Morgan Private Capital, to discuss how the boundaries between public and private markets are breaking down. Paris explains why companies are staying private longer, how value is increasingl
E348: Why “Boring” Businesses Beat Venture Capital
Is private equity alpha really about picking great deals—or about executing the same playbook better than everyone else?
In this episode, I discuss with Monty Yort, Managing Partner at GenNx360 Capital Partners, about how disciplined execution and consistency drive long-term outperformance in private equity. We break down how GenNx360 approaches proactive sourcing, why lower middle market investi
E347: The $26B CIO Who Turned Superforecasting Into Alpha
How do you manage a $26 billion public fund while keeping every investment decision disciplined, every team member calibrated, and every partner accountable?
In this episode, I sit down with Mark Steed, Chief Investment Officer of AZ Public Safety Personnel Retirement System, to explore how super forecasting and probabilistic thinking shape portfolio management. Mark shares how lessons from Dr. P
E346: $7 Billion CIO: Why the Endowment Model is Changing
How do you build a $7 billion portfolio that performs across decades while keeping every client aligned and every manager motivated?
In this episode, I sit down with Karen Welch, Chief Investment Officer at Spider Management Company, to explore the evolving role of a CIO in today’s complex investment landscape. Karen shares how lessons from Stanford’s endowment shaped her approach, why the best i
E345: How I Raised $10 Billion in Venture Capital w/Scott Painter
What does it take to raise $270 million in a risk-off market while keeping your personal life, sanity, and team intact?
In this episode, I sit down with Scott Painter, Founder & CEO, TrueCar, to unpack the 21-month journey of taking a company private. Scott shares how persistence, strategic thinking, and mental resilience allowed him to navigate investor skepticism, market volatility, and persona
E344: How the Top Family Offices are Investing Today
What if the families with the largest fortunes generate the highest returns not by chasing hot sectors, but by pacing capital, managing liquidity, and investing with a multi-decade horizon?
In this episode, I sit down with Douglas Evans, Chief Investment Officer & Partner at Callan Family Office, to explore how a $10B family office approaches private markets like an institutional investor. Doug s
E343: The Death of the 60/40 Portfolio (And What Comes Next)
What if the biggest edge in portfolio construction isn’t picking better assets but structuring a portfolio you can actually stick with through cycles?
In this episode, I sit down with Chaya Slain, President and CIO at Virtera Partners LLC, to unpack how families can access institutional-quality investing without building a full family office. Chaya explains why alternatives are often the true dri
E342: The Rise of Venture Secondaries
What if the real edge in venture isn’t picking the hottest companies, but structuring your portfolio, pacing capital, and building relationships in a way most investors never do?
In this episode, I sit down with Jamie Melzer, Founder and Managing Partner of Altra Venture Partners, to break down how she built a firm focused on late-stage venture and secondaries at the height of market dislocation.
E341: Why VC is Changing Forever ($150 Billion LP)
What if the best venture returns come from the LPs that are most patient and most strategic?
In this episode, I sit down with Scott Voss, Partner at HarbourVest, to explore how the $150B multi-manager firm generates consistent outperformance across venture, growth equity, buyouts, and secondaries. Scott shares how consensus risk, vintage year timing, and strategic co-investing shape returns, why
E340: Why Family Offices Should Avoid 60/40 Portfolios
What if building a portfolio for high-net-worth investors is more about managing downside risk than chasing returns?
In this episode, I sit down with Damien Bisserier, Managing Partner and Co-CIO at Evoke Advisors, to explore how he constructs diversified portfolios for ultra-high-net-worth families. Damien shares why after-tax returns, alternative assets, and private markets matter more than con
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