How I Invest with David Weisburd

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...

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 horizo...

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 hundre...

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...

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 fundame...

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 adva...

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-qu...

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 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...

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 f...

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...

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,...

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 workf...

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 resil...

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 smal...

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...

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 l...

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 p...

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 valu...

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 emerg...

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...

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 alloca...

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 fo...

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-investm...

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 sh...