Claim OwnershipHow I Invest with David Weisburd
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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.
288 Episodes
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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 Director 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.
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.
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.
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.
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