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How I Invest with David Weisburd

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.

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Episodes

E302: Legendary CIO Larry Kochard On Where Alpha is Today

What actually creates sustainable alpha in endowment portfolios and why do most investors mistake activity for edge? In this episode, I talk with Larry Kochard about building investment programs that endure across cycles. Drawing on his experience as CIO at Georgetown and the University of Virginia and later at Makena Capital, Larry explains why preparation before crises matters more than heroics during them, how governance and stakeholder buy-in reduce behavioral mistakes, and where real alpha still exists in increasingly efficient markets. We unpack liquidity discipline, rebalancing under stress, manager sizing, and why ?people are upstream of everything.?
2026-02-11
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E301: Why Generating Alpha is So Hard

After 300 interviews with the world?s top investors, what does alpha actually look like and why is it almost never what people think it is? In this special episode, the roles are reversed. David Weisburd, host of How I Invest and Co-Founder of Weisburd Capital, steps into the guest seat as his co-founder Curtis Pierce takes over as host. Together, they unpack the most important lessons David has learned from more than 300 conversations with CIOs, LPs, GPs, founders, and allocators representing trillions in assets. The discussion centers on why real alpha is hard, boring, and often low-status, how structural advantages drive sustainable outperformance, and why governance and portfolio construction matter more than any single trade.
2026-02-10
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E300: How I Raised $100 Billion w/Rahul Moodgal

Can institutional capital really afford to rush or is patience the ultimate edge in fundraising? In this episode, I sit down with Rahul Moodgal to unpack what it actually takes to build long-duration institutional relationships in today?s cautious capital environment. We talk about why capital raising is harder than it looks, how elite LPs think about alignment over performance, and why the best partnerships are often built over a decade?not a quarter.
2026-02-09
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E299: Why Institutional LPs Are Moving Into Lower Middle Market PE

What does it mean to be a true partner to lower middle market businesses? David Weisburd speaks with Peter Elliot Rothschild about building RF Investment Partners around listening first, designing bespoke capital solutions, and investing as the first institutional capital in family-owned companies. Peter discusses minority versus control investing, the role of trust and relationships, and why value creation in the lower middle market is driven less by financial engineering and more by people, incentives, and execution.
2026-02-06
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E298: How Family Offices Think About Illiquidity, Taxes, and Compounding

How do tax efficiency, private markets, and structural change intersect in modern portfolio construction? David Weisburd speaks with Jeffrey Fulk about his career across hedge funds, fund-of-funds, and wealth platforms, and how AlTi Global approaches tax-aware investing, private credit, evergreen structures, and evolving access to private markets. Jeff shares insights on where opportunity is emerging as markets shift and why after-tax outcomes increasingly drive investment decisions.
2026-02-05
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E297: Advisory Boards & LPACs: A Complete Masterclass for GPs

Why do so many advisory boards look impressive on paper but fail to deliver real value when it actually matters? In his second appearance on the podcast, I sit down again with Matt Curtolo, a senior advisor to both GPs and LPs who has worked with more than 600 general partners across venture, growth equity, and private equity. Matt breaks down the biggest misconceptions around advisory boards and LP advisory committees, why ?performative? governance quietly destroys trust, and how the best managers design advisory structures with real purpose. We get tactical on compensation, LPAC construction, advisor selection, and how great firms turn advisors into a true strategic weapon?not window dressing.
2026-02-04
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E296: Former CIO of CalSTRS on Why LPs Overpay for ?Innovation?

What actually separates great institutional investors from average ones and why does governance matter more than brilliance? In this episode, I talk with Christopher J. Ailman, former Chief Investment Officer of CalSTRS, about the decisions that shaped one of the largest and most successful public pension funds in the world. Chris reflects on more than two decades leading CalSTRS, why asset allocation and governance drive the vast majority of outcomes, and how building a resilient, low-cost, long-term portfolio matters far more than chasing the latest investment trends. We also discuss culture, decentralization, and what CIOs consistently get wrong when managing people and risk.
2026-02-03
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E295: Why AI Agents Will Quietly Replace 80% of Investment Teams

Why are humans ? not models ? still the biggest bottleneck to AI progress, and what happens when that bottleneck becomes a business? In this episode, I talk with Ali Ansari, Founder and CEO of micro1, about the hidden layer powering today?s AI breakthroughs: high-quality human intelligence. Ali explains how micro1 pivoted from an AI recruiting startup into a critical data infrastructure company for frontier AI labs, why expert-generated data is now the limiting factor in model performance, and what needs to change for AI agents to actually work in production. We also explore how focus, market timing, and ruthless prioritization enabled micro1 to scale more than 30× in a single year.
2026-02-02
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E294: Endowment Model vs Total Portfolio Approach: The Real Trade-Offs

How should families think about portfolio construction when traditional diversification breaks down? David Weisburd speaks with Michael Phipps about building New Republic Partners, designing portfolios around growth, income, and diversification, and why open architecture matters in multifamily offices. Michael discusses common portfolio mischaracterizations, the role of alternatives and co-investments, and how families can better align risk, liquidity, and long-term objectives.
2026-01-30
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E293: Inside GEM: How a $12.5 Billion Platform Selects Outlier Funds

How do experienced LPs evaluate venture managers in an increasingly crowded and bifurcated market? David Weisburd speaks with Kate Simpson about her career as a venture allocator, her move to GEM to lead venture investing, and how institutional LPs assess sourcing, portfolio construction, and power-law dynamics. Kate explains how reference calls, fund sizing, access, and long-term relationships shape conviction in venture manager selection.
2026-01-29
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E292: How the Former CalPERS CIO Built a High-Performance Investment Culture

How does one of the world?s largest pension funds shift its culture, governance, and investment process at scale? David Weisburd speaks with Nicole about her transition from Ontario Teachers? Pension Plan to serving as CIO of CalPERS, implementing a total portfolio approach, and leading organizational change during a period of market and operational disruption. Nicole shares lessons on governance, board alignment, co-investing, and building long-term investment institutions.
2026-01-28
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E291: Incentives, Not Intuition: How VC Really Works

Why have consumer startups fallen out of favor and why might that be the biggest opportunity of the next decade? In this episode, I talk with Brian O?Malley, founder of Tactile Ventures, about why consumer investing is deeply misunderstood and how AI is unlocking a new wave of products that improve everyday American lives. Brian shares lessons from two decades investing at Accel, Battery, and Forerunner, why incentives?not talent?drive venture outcomes, and how the best consumer companies blend technology, business models, and human behavior. We also explore why AI is moving out of its ?toy phase,? why humans still need to stay in the loop, and how early-stage investors win by giving founders something large platforms can?t: time.
2026-01-27
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E290: How LPs Underwrite Venture in 2026

Why does today?s venture market feel increasingly untethered from historical precedent? David Weisburd speaks with Narayan Chowdhury about structural shifts in venture capital, the limits of data-driven decision-making, and how founders and investors navigate an unusually noisy and fragmented market. Narayan shares how access, trust, and long-term relationships are becoming more important as traditional signals lose reliability.
2026-01-26
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E289: The Evolution of Private Credit and What Comes Next

Why did private credit secondaries emerge, and what problem do they solve for investors? David Weisburd speaks with Rakesh Jain about building one of the world?s largest private credit secondary platforms at Pantheon, the mechanics of liquidity in private markets, and how seasoned portfolios differ from primary credit origination. Rick explains how diversification, underwriting discipline, and alignment shape risk-adjusted outcomes across cycles.
2026-01-23
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E288: Inside a PE Fund Ranked #1 in IRR, DPI, and TVPI

How do you raise $875M in one of the hardest fundraising markets in decades and still outperform on DPI, IRR, and culture? In this episode, I sit down with Jesse D. Serventi and Atif Gilani, Founding Partners of Renovus Capital Partners, to unpack what actually compounds in private equity over 15+ years. We break down why staying in the lower end of the lower middle market creates structural advantage, how talent density became their real edge, and why portfolio construction?not deal hype?is the hidden driver of net returns. Jesse and Atif also share how Renovus evolved from three founders doing everything into a scaled firm built to last decades, not cycles.
2026-01-22
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E287: What Separates Top Decile Managers from Everyone Else

What separates enduring investment firms from those that quietly break as they scale? In this episode, I talk with Chris Brimsek, Managing Partner of CAB Advisory, about the unseen mechanics behind building durable alternative investment firms. Drawing from his experience as Chief of Staff to David Rubenstein and former COO of Carlyle?s $15B Infrastructure & Energy business, Chris explains why culture, judgment transfer, and succession?not deal mechanics?are the true bottlenecks to long-term performance. We unpack how elite leaders create environments without intellectual hierarchy, why forgiveness builds trust faster than perfection, and how emerging managers can avoid the most common traps as they scale.
2026-01-21
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E286: How LPs Can Actually Find Alpha in Venture

How well do venture capital returns really reflect skill versus structure? In this episode, David Weisburd speaks with Abe about what large-scale AngelList data reveals about seed investing, power-law returns, and why traditional assumptions around expected value, conviction, and diversification often break down. Abe explains how adverse selection shapes outcomes, why access matters more than insight, and where data-driven strategies may ? and may not ? apply in venture capital.
2026-01-20
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E285: The Lower Middle Market: Where Private Equity Still Generates Alpha

What does it take to build an investment firm outside the traditional private equity model? David Weisburd speaks with Jeff Schwartz about founding Corbel Capital Partners, identifying opportunities in the lower middle market, and why structured capital fills a gap left by banks and large buyout firms. Jeff discusses the operational realities of scaling an investment platform, fundraising challenges, and how market inefficiencies continue to shape strategy selection.
2026-01-19
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E284: Why Family Offices Invest Differently w/Robert Blabey

How do family offices approach investing differently from institutional capital? David Weisburd speaks with Robert about building Align, identifying gaps between capital and resources in family offices, and why downside protection shapes every investment decision. Robert discusses private credit, opportunistic investing, shorter-duration strategies, and how collaboration among families creates a distinct and disciplined investment ecosystem.
2026-01-16
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E283: How AI will Affect Financial Markets

What happens when the marginal cost of intelligence approaches zero? David Weisburd speaks with Richard Socher about building U.com, the evolution of AI search and agents, and why infrastructure?not hype?will determine AI?s real economic impact. Richard shares a first-principles view on where AI creates value, how enterprises are deploying agents today, and what long-term shifts in labor, productivity, and education may follow.
2026-01-15
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E282: Why LPs are Investing into Independent Sponsors

What role do independent sponsors play in today?s lower middle market private equity ecosystem? David Weisburd speaks with Tom Duffy about how TIFF partners with independent sponsors, why deal-by-deal investing can improve alignment, and what differentiates high-quality sponsors in a rapidly growing market. Tom explains how sourcing, economics, and hands-on diligence shape long-term GP relationships and inform future fund commitments.
2026-01-14
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E281:The Tsunami of Pain Facing Venture Capital

Why do some venture-backed companies struggle to survive despite strong technology and teams? In this episode, David Weisburd speaks with Trey Ward about the structural differences between software and hard-tech businesses, the predictable ?Death Valley? many startups face, and what recent data suggests about the future of venture funding. Trey shares how capital intensity is often misunderstood, why graduation rates are declining, and how profitability can create a path forward when fundraising stalls.
2026-01-13
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E280: The Art of Quiet Compounding w/Mark Sotir

Why do the best investors spend more time preparing for what can go wrong than forecasting what might go right? In this episode, I talk with Mark Sotir, President of Equity Group Investments, about what it really means to invest with an owner?s mindset. Mark shares lessons from working alongside Sam Zell for nearly two decades, why staying alive matters more than maximizing any single outcome, and how long-term capital changes behavior inside portfolio companies. We break down why protecting downside creates asymmetry, how adaptability beats prediction, and why value creation comes from operating discipline, not transaction timing.
2026-01-12
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E279: Why Size Becomes the Enemy of Venture Returns w/Logan Allin

Why does venture capital break when liquidity disappears and what actually creates alpha when markets get hard? In this episode, I talk with Logan Allin, Founder and Managing Partner of Fin Capital, about why private markets are structurally changing, how secondaries are becoming a primary liquidity mechanism, and why discipline ? not optimism ? is what separates enduring managers from zombies. Logan explains how Fin Capital built a full-lifecycle platform across venture and late-stage secondaries, why fund size is the enemy of performance, and how contrarian positioning creates real structural alpha over time.
2026-01-09
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E278: What Separates the Top 1% of GPs

What if the most powerful investment strategy isn?t optimization but making one truly great decision each year? In this episode, I talk with Joshua Browder, Founder and CEO of DoNotPay and a solo pre-pre-seed investor, about how momentum, conviction, and first-belief investing create outsize outcomes. Joshua shares how DoNotPay became a profitable, dividend-paying AI consumer company with a team of 14, why he focuses on backing founders before they look credentialed, and how acting decisively on binary choices can matter more than years of incremental improvement. We also explore why grit beats IQ, how momentum keeps startups alive, and what it really takes to be a founder?s first believer.
2026-01-08
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E277:Why the Best GPs Refuse to Raise More Capital

Why is the hardest discipline in growth equity not finding great companies but refusing to grow past the point where returns break? In this episode, I talk with Deepak Sindwani, Co-Founder and Managing Partner of Wavecrest Growth Partners, about why fund size discipline, culture, and integrity matter more than optics in building a great investment firm. Deepak explains why Wavecrest capped Fund III at $450M despite excess demand, how staying in the sub-$50M equity check range preserves alpha, and why being a true growth partner ? not a financial engineer ? creates better outcomes for founders and investors alike.
2026-01-07
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E276: Lessons from Allocating $70B as CIO at the University of Texas

Why do the biggest investing breakthroughs come not from complexity, but from simplicity and why is that so hard for smart people to accept? In this episode, I talk with Britt Harris, one of the most experienced institutional investors in the world, about what really drives long-term investment success inside large pools of capital. Britt explains why simplicity beats complexity, how scale creates negotiating power and structural advantage, and why engagement ? not intelligence ? is the true separator of performance. We discuss how innovation in investing is usually recombination, not invention, why empowered teams outperform credentialed ones, and how leaders can systematically create cultures that compound.
2026-01-06
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E275: Does Grit Actually Matter in a GP ? or Is It Just a Good Story?

Why do the people who build the most meaningful things almost always choose the hardest path and what does that unlock in the long run? In this episode, I talk with Larsen Jensen, Founding General Partner of Harpoon Ventures, about why deliberately choosing difficult problems builds the resilience, clarity, and long-term edge required to create category-defining companies. Larsen shares lessons from his time as an Olympic medalist and Navy SEAL, how those experiences shaped his investing philosophy, and why venture capital is ultimately a power-law game driven by rare outliers. We explore how founders develop mental toughness, how conviction is formed under uncertainty, and why great investors learn to trust teams more than models.
2026-01-05
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E274:How LPs Miss Early Asymmetry by Waiting

What if the biggest barrier to earning returns in alternatives isn?t access, fees, or performance but friction, complexity, and behavior? In this episode, I talk with Brett Hillard, Founder and CEO of GLASFunds, about why infrastructure matters more than selection in alternative investing. Brett explains how GLASFunds helps wealth managers implement alternatives at scale, why K-1 friction keeps investors out of high-return asset classes, and how thoughtful design around vintages, liquidity, and reporting can dramatically improve long-term outcomes. We also explore why ?alternatives? is an overused label, how to build portfolios across vintages, and why illiquidity can actually protect investors from themselves.
2026-01-02
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EP273: What the Best Family Offices Do Differently

What if managing your own capital and not outsourcing it is the highest-return investment decision you can make? In this episode, I talk with Alex Tonelli, Co-Founder of Endurance, about what changes when entrepreneurs manage their own money with the same first-principles thinking they use to build companies. Alex explains how Endurance evolved from a startup holding company into a highly structured family investment office, why principal-driven capital behaves differently than institutional capital, and how disciplined portfolio construction, vintage diversification, and contrarian thinking create durable long-term returns. We also explore why institutions systematically underperform their opportunity set ? and how to avoid the behavioral traps that cause it.
2025-12-31
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EP272: How a $10B Company Turned De-Extinction into a Platform

What kind of entrepreneur decides to bring back extinct species and why might that become one of the most important businesses of our lifetime? In this episode, I talk with Ben Lamm, Co-Founder and CEO of Colossal Biosciences, about why de-extinction is not science fiction but an engineering problem ? and how solving it is creating breakthrough technologies across biology, conservation, and medicine. Ben shares how Colossal evolved from a bold idea into a multi-billion-dollar platform, why mammoths, dire wolves, and dodos became cultural gateways into serious science, and how mission-driven companies can attract talent, capital, and public imagination at once.
2025-12-30
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E271: The Future of VC: Space, Energy, Defense

How do you spot a frontier-tech company before it becomes obvious and why is being early so much harder than being right? In this episode, I talk with Jonathan Lacoste, Founder and General Partner of Space VC, about investing at the moment when ideas are still non-consensus. Jonathan explains the difference between deep tech and frontier tech, why founder migration is the strongest signal of emerging opportunity, and how pre-seed investors create alpha by backing contrarian founders before markets agree. We discuss how grit and mission outperform IQ, why concentration beats diversification in early-stage portfolios, and how patience compounds into an edge over time.
2025-12-29
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EP270: How Billionaires Avoid Family Chaos (and Taxes)

What if the most important decision in wealth planning isn?t the tax strategy?but who you trust to make decisions when you no longer can? In this episode, I talk with Thomas Monroe, Founder and President of Blue Sky Trust, about the real role of a trustee and why independence, judgment, and governance matter more than technical structuring alone. Thomas explains how trustees sit at the intersection of tax, legal, investment, and family dynamics?and why poor trustee selection can quietly undermine even the most sophisticated planning. We explore real-world trust use cases, parenting and purpose across generations, and how thoughtful structuring creates optionality without eroding values.
2025-12-26
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EP269: The $350M 30-Year Fund Model

What happens when you throw out the playbook of traditional private equity and instead build businesses with permanent capital, no exits, and no management fees? In this episode, I talk with Brent Beshore, founder and CEO of Permanent Equity, about a radically different approach to investing that focuses on ownership, compounding, and alignment with operators over decades?not years. Brent explains why avoiding leverage and fees isn?t just philosophically different but materially better for long-term outcomes, how Permanent Equity partners with founders who want legacy and culture to endure, and why patient reinvestment beats short-term optimization. We break down how permanent capital accelerates growth, how to think about cash flow vs. IRR optics, and the unique investor mindset required to succeed outside the traditional private equity model.
2025-12-24
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EP268: Inside LP Psychology: How Great GPs Raise Capital in 2025

Why do so many strong GPs struggle to raise capital today and what actually separates fast, oversubscribed fundraises from stalled ones? In this episode, I talk with Alexander Russ, Senior Managing Director at Evercore and Head of North America for the firm?s Private Funds Group, about what really drives fundraising success in today?s crowded private markets. Alex breaks down the psychology of LP decision-making, why momentum in the first close matters more than almost anything else, and how the best GPs differentiate themselves through narrative, preparation, and credibility rather than fee discounts. We dive into why fundraising is ultimately a momentum machine, how to engineer demand early, and why trust?built over years?can be lost in a single raise.
2025-12-23
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E267: Why 95% of LPs Misread Private Market Returns

Do private markets actually outperform public markets once you properly adjust for risk or is that belief built on flawed data? In this episode, I talk with Dr. Gregory W. Brown, one of the leading academic researchers in alternative investments, about what decades of data really say about private equity, venture capital, and risk-adjusted returns. We break down why private-market performance is so hard to measure, how tools like the Kaplan?Schoar PME changed institutional thinking, and what investors misunderstand about beta, volatility, and alpha. Greg also explains why buyouts and ventures behave very differently, how fund size and geography affect outcomes, and what this research implies for building diversified portfolios today.
2025-12-22
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E266: J.P. Morgan CIO: Mistakes Top Investors Make

Why do most investors fail at the exact moments when staying invested matters most?and how can options help fix that? In this episode, I talk with Hamilton Reiner, Managing Director at J.P. Morgan Asset Management and CIO of the U.S. Core Equity Team, about how options can be used not for speculation, but to create discipline, manage risk, and help investors stay invested through market volatility. Hamilton shares lessons from more than three decades managing equities and derivatives, explains why volatility is misunderstood, and breaks down how hedged strategies, rebalancing, and risk-based portfolio construction can dramatically improve long-term outcomes?without requiring heroic market timing.
2025-12-19
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E265: What the Coach to Sequoia, A16Z and Benchmark Learned About Power and People

Why do the most successful investors and founders still miss their best opportunities?and how much of that comes down to poor relationship management? In this episode, I talk with Patrick Ewers, founder of Mindmaven, about why relationships?not intelligence or effort?are the true limiting factor in professional success. Patrick shares lessons from being an early employee at LinkedIn under Reid Hoffman, coaching partners at top firms like Sequoia and Andreessen Horowitz, and building a systemized approach to relationship management that scales. We break down why important things lose to urgent ones, how delegation and leverage unlock effectiveness, and why small, consistent actions compound into billion-dollar outcomes.
2025-12-18
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E264: The Asymmetric Edge: Generating Alpha in Venture

How do the best venture investors consistently spot unicorn founders before the rest of the market even knows they exist? In this episode, I talk with Jamie Lee, Co-Founder and Managing Partner of Tamarack Global, about sourcing asymmetric deal flow in deep tech and why founder referrals are the single strongest signal of future breakout companies. Jamie explains how Tamarack applies hedge-fund-level diligence at the seed stage, why intuition and pattern recognition matter as much as data, and how concentrated conviction?combined with relentless research?drives their unusually high unicorn hit rate. We also explore humanoid robotics, labor automation, and why the next industrial revolution is already underway.
2025-12-17
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E263: Inside the $5 Billion Fund Backed by 700 LPs

How do you scale a growth equity firm from a $52M first fund to $5B across six funds?without losing discipline or trust? In this episode, I talk with Brian Neider, Managing Partner at Lead Edge Capital, about building a durable growth equity platform by combining rigorous metrics with deep relationship-building. Brian shares how Lead Edge created a differentiated LP model centered on high-net-worth individuals who actively support portfolio companies, why communication and education compound trust over decades, and how a strict investment framework helps avoid negative alpha as the firm scales. We also discuss why exits matter more than paper gains, how to think about ?walking dead? portfolio companies, and what truly energizes long-term investing.
2025-12-16
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E262: The 50-30-20 Portfolio: How Institutions Are Rebuilding 60/40

How do you build portfolios that survive liquidity crises, inflation shocks, and the most volatile market regimes in modern history? In this episode, I talk with Alfred Lee, Deputy Chief Investment Officer at Q Wealth Partners and one of Canada?s most experienced multi-asset portfolio architects. Alfred previously managed over $75 billion across equities, fixed income, commodities, factor strategies, and thematic ETFs at BMO?while also spending a year at the Bank of Canada running part of its quantitative easing program during the pandemic. He shares what he learned from overseeing $25B in fixed income and $50B in equities, how ETFs transformed the public markets, why alpha is harder to generate than ever, and why alternatives, real assets, CTAs, and discretionary macro strategies must anchor the next generation of portfolios.
2025-12-15
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E261: How Sovereign Wealth Funds Create Alpha w/Peter Madsen

What does it take to build a sovereign wealth fund from scratch?and still outperform in some of the hardest markets in decades? In this episode, I talk with Peter Madsen, Chief Investment Officer of the Utah School & Institutional Trust Funds Office (SITFO), one of the most quietly sophisticated sovereign wealth funds in the United States. Peter shares how he went from running hedge fund portfolios in London to becoming the first investment hire tasked with modernizing Utah?s endowment. We break down SITFO?s philosophy on mean reversion, factor-based investing, public vs. private markets, active vs. passive strategy, and how a small CIO team competes with far larger institutions. Peter also explains why small caps are broken, how he shifted capital into private equity, why micro-VC funds outperform mega-funds, and how SITFO uses AI and collaborative models to underwrite managers in a world of overwhelming information.
2025-12-12
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E260: How Founders Access Liquidity in Pre-IPO Companies

How do you turn distressed opportunities into structural alpha?again and again?in an asset class most investors still misunderstand? In this episode, I?m joined by Philip Benjamin, Co-Founder and Managing Partner of Colzen Capital, about how he built a differentiated pre-exit liquidity strategy that serves founders, executives, and investors simultaneously. Philip shares how his fourth-generation real estate background and the 2008 financial crisis shaped his investing worldview, how he applies a distressed-real-estate mindset to late-stage ventures, and why Colzen?s structured equity financing model creates downside protection, aligned incentives, and access to elite companies long before IPO. We also discuss portfolio construction, expected return math, founder psychology, and why this emerging asset class is quietly becoming massive.
2025-12-11
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E259: The Institutional Way to Invest in Crypto w/Rennick Palley

What does it take to build four top-decile crypto funds in one of the most volatile asset classes on earth? In this episode, I talk with Rennick Palley, Founder of Stratos, about how he approaches crypto investing with a disciplined, mathematically grounded framework. We break down how Stratos constructs top-performing venture and liquid portfolios, why crypto is shifting from momentum-driven trends to fundamentals, how to size positions without blowing up, and why Bitcoin and gold are behaving the way they are in today?s macro environment. Rennick also shares his philosophy on decisiveness, conviction, and avoiding the costly mistakes investors make when they hesitate.
2025-12-10
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E258: Ryan Serhant: Why Leaders Who Don?t Evolve Get Left Behind

How do you build a $10B real estate empire by turning yourself into a media company?and why is vulnerability the ultimate competitive advantage? In this episode, I talk with Ryan Serhant, founder and CEO of SERHANT., one of the most influential real estate brokerages in the world and a pioneer at the intersection of real estate, media, entertainment, and technology. Ryan breaks down the turning points that shaped his career?from selling a $13M townhouse through YouTube a decade ago, to betting everything on social media before anyone believed in it, to building a fast-growing real estate ecosystem powered by content, authenticity, and scale. We dive into Season 2 of Netflix?s Owning Manhattan, the biggest highs and lows of his year, the reality of leading a thousand-agent organization, and why the future of real estate is screenless, human-centric, and powered by creators.
2025-12-09
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E257: What I Learned Advising the World?s Top CIOs at Goldman Sachs

Why do the world?s best CIOs make investment decisions based on gut ? not spreadsheets? In this episode, I?m joined by Julia Rees Toader, CFA, Founding Partner at PrinCap and former Global Head of Portfolio Strategy at Goldman Sachs Asset Management. Julia spent a decade advising sovereign wealth funds, pensions, private banks, and ultra-wealthy families on portfolio construction, risk management, and asset allocation. She shares the biggest lessons she learned from working with the world?s top CIOs ? from why diversification rarely drives behavior, to where the smartest allocators take idiosyncratic risk, to how emotions secretly influence the most sophisticated investment decisions.
2025-12-08
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E256: What Fintech Will Look Like in 5 Years - Steve McLaughlin (FT Partners)

What does it take to build the most dominant FinTech investment bank in the world?starting from a $99 incorporation and a used laptop? In this episode, I speak with Steve McLaughlin, Founder, CEO, and Managing Partner of FT Partners, widely regarded as the leading investment bank in FinTech. Steve has personally closed hundreds of the biggest M&A, capital raise, and IPO advisory transactions in the industry?while pioneering a completely different approach to value creation in investment banking. We cover everything from the humble beginnings of FT Partners, to Steve?s philosophy of ?never die,? to his groundbreaking thesis on AI, tokenization, defensibility in FinTech, and why he believes we?re entering a new era of trillion-dollar global financial technology companies. We also dive into the incentives model Steve built that has generated some of the largest fees in the history of investment banking?and why clients keep coming back.
2025-12-05
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E255: How to Hire the Top 0.1%

What does it take to recruit the top 0.1% of engineers in the world ? and why has talent become the ultimate constraint in AI? In this episode, I?m joined by Chris Vasquez, Founder & CEO of Quantum Talent, one of the most in-demand technical recruiting firms in the AI ecosystem. We discuss why elite engineering talent has become the core bottleneck in AI, how companies can actually attract S-tier builders, what founders get wrong about hiring, and why talent density?not headcount?is the strongest predictor of outcomes in today?s startup environment.
2025-12-04
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E254: How to Build a 100-Year Venture Firm

How do you balance power-law outcomes with real risk management while building a durable venture franchise? In this episode, I speak with Mark Peter Davis (MPD) ? Managing Partner of Interplay, entrepreneur, author, podcaster, and one of New York?s most active early-stage investors. We discuss how Mark?s philosophy of investing has evolved over 20 years in venture, why VC psychology is so different from other asset classes, and how he manages for both outliers and consistency across vintages. Mark breaks down secondaries, constructing high-access portfolios, founder relationships, narrative risk, the role of operational support, and why grit compounds just like interest.
2025-12-03
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E253: How Great CIOs Think w/Bill Brown

How do the best family offices consistently spot power-law opportunities and avoid the trap of ?fake busy? work? In this episode, I?m joined with William (Bill) Brown, CIO of the Terrace Tower Group, about the lessons he learned working for billionaire Leonard Stern, how he helped evolve a legacy real-estate portfolio into a globally diversified family office, and what pattern recognition looks like across trades like the Big Short, crypto, and private credit. We discuss how Bill thinks about decision-making, mental models, productivity, and the mindset required to survive long enough to capture asymmetric upside.
2025-12-02
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