How I Invest with David Weisburd

What if the best private equity opportunities are the ones no one else is set up to pursue? In this episode, I sit down with Jeff Collins, Founder and Managing Partner of Cloverlay, to explore how he built a $2 billion firm by going where capital isn’t. After 14 years at Morgan Stanley Investment Management, Jeff spun out to focus on what he calls “uncorrelated private assets” - niche, often overlooked segments where return dispersion is wide and operator selection matters more than financial engineering.

Why would an LP invest in the GP instead of the fund… and what problem is GP stakes really solving? In this episode, I sit down with Todd Owens, Managing Partner of Cantilever Group, to unpack the world of GP stakes. Todd explains what investors are actually buying when they take a minority stake in an alternative asset manager, why liquidity risk is the central challenge, and how structural innovation could reshape the asset class.

What separates elite venture LPs from everyone else… and why do most family offices underestimate the governance required to win? In this episode, I sit down with Michael P. Larsen, a longtime Partner at Cambridge Associates, to unpack nearly two decades of building venture and private equity portfolios for leading institutions and family offices. Michael shares why longevity may be the ultimate competitive advantage in asset management, how governance quietly determines venture outcomes, and why portfolio size can matter just as much as manager selection. We dive into power laws, spiky returns, growth equity’s overlooked role, co-invest best practices, and how benchmarking can help LPs stay disciplined during optically challenging cycles.

What if the biggest untapped source of alpha isn’t better investments… but better tax structure? In this episode, I sit down with Andrew Berman, Co-Founder and Managing Partner of Arqitel, to explore the overlooked power of tax-aware private real estate investing. After starting his career at AQR Capital Management and working closely with one of its co-founders inside a family office, Andrew saw firsthand how tax-aware strategies transformed public market investing. He realized private markets had yet to fully adopt the same discipline. We break down structural alpha, why many private real estate managers are incentivized to sell too soon, and how taxable investors can materially improve long-term wealth creation by aligning investment strategy with tax structure. In increasingly efficient markets, tax may be one of the few durable advantages left.

What if the easiest alpha in public markets isn’t stock picking… but taxes? In this episode, I sit down with Zach Wainwright, Founder of Twin Oak ETF Company, to break down structural alpha, ETF tax efficiency, and how high-net-worth investors can compound capital more intelligently. Zach shares lessons from his time at Wellington, TIFF, and inside a single-family office — and why long time horizons, incentive alignment, and tax awareness may be more powerful than traditional stock-picking alpha. We also dive into tail-risk hedging inside an ETF wrapper and how families can design portfolios to survive extreme drawdowns without sacrificing long-term compounding.

What if success isn’t about talent… but about multiplying your effort by 10? In this episode, I sit down with Grant Cardone, CEO of Cardone Capital, to break down the mindset behind the 10X Rule, omnipresence in marketing, raising billions from retail investors, and why quantity always precedes quality. Grant shares how he built a $5B real estate portfolio, scaled a media machine that sends hundreds of millions of emails per year, and combined Bitcoin with multifamily real estate to create a new hybrid investment vehicle. We also unpack why most people underestimate effort, why repetition builds self-esteem, and why illiquidity may be the real edge in investing.

If private equity generates alpha, why are investors still paying for beta? In this episode, I sit down with Roger Vincent, Founder and CIO of Summation Capital, to break down portfolio construction, co-investing, and fee alignment in private equity. After more than a decade leading Cornell University’s multi-billion-dollar private equity portfolio, Roger shares why diversification in PE actually increases expected return, how elite endowments use co-investments to systematically reduce fee drag, and why most allocators are misaligned with the capital they steward. We also unpack Summation’s industry-first structure—charging carry only on alpha over a public benchmark and offsetting fees through a no-fee, no-carry co-investment program.

Why does applying institutional investing frameworks often fail for taxable investors and families? David Weisburd speaks with Aneet Deshpande about adapting the endowment model to private clients, the rise of tax-aware private market investing, and why governance, pacing, and asset location matter more than product selection. Aneet explains how taxes, liquidity needs, and behavioral risks fundamentally change portfolio construction—and why clarity of objectives is the real edge.

Can ethics, generosity, and long-term relationships really outperform aggression in venture capital? David Weisburd speaks with David Hornik about why “nice guys finish first… eventually,” how power-law outcomes shape a venture career, and why reputation compounds more reliably than tactics. Hornik explains why backing unflinchingly ethical founders isn’t just moral—it’s a durable competitive advantage in an industry defined by uncertainty.

Why have continuation vehicles become one of the fastest-growing segments in private markets? David Weisburd speaks with Benjamin Carper about what’s driving record CV volume, how these transactions solve structural mismatches in private equity fund lives, and why both LPs and GPs hold mixed views on the strategy. Ben explains how continuation vehicles create liquidity, extend ownership of high-quality assets, and reshape portfolio management across buyout and venture markets.

Why has liquidity across private markets broken down and what does it mean for institutional portfolios? David Weisburd speaks with Alex Ambroz about collapsing distributions, the rise of continuation vehicles and secondaries, and why many allocators are facing a structural mismatch between models and reality. They explore whether “private is the new public,” how incentives shape GP behavior, and what LPs must change to adapt to a new normal of prolonged illiquidity.

What happens when AI stops assisting humans and starts replacing decision-making itself? David Weisburd speaks with Camilo Acosta about the rise of agentic AI, why incumbents still leave massive openings for startups, and how AI will reshape labor, venture capital, and entire asset classes. Camilo explains how investing ahead of regulation, betting on founders over ideas, and building for a fully agentic future define the next era of venture.

What happens when capital markets move from batch processing to real time? David Weisburd sits down with Yuval Rooz to discuss his path from Citadel and DRW to founding Digital Asset and building the Canton Network. Yuval explains why blockchain is less about crypto speculation and more about upgrading the infrastructure of global capital markets—unlocking 24/7 settlement, asset utility, and new forms of liquidity across public and private markets.

How do you compete with Sequoia and Andreessen while running a $650M fund and still expect to outperform? In this episode, I sit down with Glenn Solomon, Managing Partner at Notable Capital, to break down how focused early-stage investing can outperform mega-platform venture funds. Glenn explains why 70%+ of venture dollars now go into mega-rounds over $100M, why Notable stays disciplined at seed and Series A, and how delivering “unscalable” founder support creates real edge. We also go deep on Anthropic, the so-called “software apocalypse,” AGI narratives, and where durable alpha exists in an AI-dominated world.

Why does execution velocity matter more than pedigree at the earliest stages of company building? David Weisburd speaks with Eric Bahn about the concept of “hustle,” why early judgments about founders tend to persist, and how throughput, learning speed, and grit outperform traditional signals in pre-seed investing. Eric explains Hustle Fund’s wide-net strategy, its community-driven platform model, and how changing startup timelines are reshaping venture economics.

Why are vertical AI applications emerging as some of the most defensible opportunities in technology today? David Weisburd speaks with Nick Beim about why context—not raw intelligence—is becoming the key driver of AI performance, and how vertical software is reshaping wealth management, legal services, and defense. Nick shares how legacy infrastructure, industry economics, and human-centered workflows create enduring opportunities for AI-driven transformation.

How should investors think about risk when traditional measures like volatility fall short? David Weisburd speaks with Jeff Blazek about portfolio construction across institutions and family offices, why drawdown matters more than standard deviation, and how allocators should balance public and private markets. Jeff shares first-principles thinking on liquidity, behavioral risk, and building resilient portfolios across market cycles.

Where does real edge still exist in public markets and how do you size risk when certainty doesn’t exist? In this episode, I talk with Ari Levy, Founder and CIO of Lakeview Investment Group, about applying probability theory, arbitrage, and disciplined position sizing to public equity investing. Ari explains how early lessons from card counting and game theory shaped his approach to risk, why small-cap markets remain structurally inefficient, and how activism, arbitrage, and management access can create asymmetric outcomes—without blowing up the portfolio.

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.”

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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 working directly with 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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.