How I Invest with David Weisburd

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.