How I Invest with David Weisburd

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...

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,...

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 Fore...

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 tradi...

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 ali...

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 advan...

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 cu...

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 insi...

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 challeng...

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 d...

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, producti...

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 relationshi...

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 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...

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. Lo...

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 o...

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 II...