Building How I Invest: Podcasting, Venture Deal Flow, and the Long Game with David Weisburd

Building something great is hard. The question is: which hard are you willing to choose?That’s something David Weisburd and I dug into on the latest episode.David chose podcasting as his hard.Three years ago, he committed to building How I Invest for at least a decade - before he knew whether it would work. There were no guarantees. Just the grind of booking guests, navigating compliance, building credibility, and showing up episode after episode. That commitment eventually turned the podcast into something much bigger: a network of investors, entrepreneurs, relationships, and venture deal flow.And that’s what I found most interesting about our conversation...The podcast wasn't just building David’s network. It was building David.We talked about:→ The power of “information alpha” and “relationship alpha”→ Why some emerging managers have a winner mindset—and others don't→ Why founder-product fit matters→ How relationships compound over time→ And why the best opportunities often come from playing the infinite gameMy biggest takeaway: You can’t make building something great easy. But you can choose a hard worth doing.Then you have to stay in the game long enough for the compounding to begin. Big thanks to David for joining the pod.Listen to the full convo here:⏱️ Chapter Markers:00:00 — Intro — why this convo is meta01:02 — Meet David Weisburd and How I Invest03:15 — Origin story: dinner with Eric Torenberg; launching the pod07:45 — Network effects and early marquee guests10:40 — The grind: LP compliance and identity risk12:10 — When it “clicked”: letting the podcast work on you16:50 — Skill-building, humility, and editing your own transcripts19:50 — Podcast as mentorship; testing yourself with elite minds22:40 — The infinite game of investing; a 10-year commitment24:35 — Information alpha, relationship alpha, parasocial effects28:10 — Why podcast convos deepen relationships; “mock podcasts”30:20 — From founder to podcaster; values-first firm-building34:30 — Weisburd Pierce: partnering on sensitive pro rata rights37:40 — Media as access: why companies want creators on cap tables39:45 — What makes a great GP: the winner vs. victim mindset43:00 — Tactics to be default-alive; example from Hustle Fund46:20 — Founder–product fit, psychology, and productizing yourself49:10 — Long-term relationships > short-term fees in private markets52:00 — Closing thoughts and thanksLINKSDavid Weisburd: LinkedInHow I Invest Podcast: WebsiteInterplay: Website, LinkedIn, XMPD: LinkedIn, X