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 game

My 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 meta

01:02 — Meet David Weisburd and How I Invest

03:15 — Origin story: dinner with Eric Torenberg; launching the pod

07:45 — Network effects and early marquee guests

10:40 — The grind: LP compliance and identity risk

12:10 — When it “clicked”: letting the podcast work on you

16:50 — Skill-building, humility, and editing your own transcripts

19:50 — Podcast as mentorship; testing yourself with elite minds

22:40 — The infinite game of investing; a 10-year commitment

24:35 — Information alpha, relationship alpha, parasocial effects

28:10 — Why podcast convos deepen relationships; “mock podcasts”

30:20 — From founder to podcaster; values-first firm-building

34:30 — Weisburd Pierce: partnering on sensitive pro rata rights

37:40 — Media as access: why companies want creators on cap tables

39:45 — What makes a great GP: the winner vs. victim mindset

43:00 — Tactics to be default-alive; example from Hustle Fund

46:20 — Founder–product fit, psychology, and productizing yourself

49:10 — Long-term relationships > short-term fees in private markets

52:00 — Closing thoughts and thanks

LINKS

• David Weisburd: LinkedIn
• How I Invest Podcast: Website
• Interplay: Website, LinkedIn, X
• MPD: LinkedIn, X