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