Building How I Invest: Podcasting, Venture Deal Flow, and the Long Game with David Weisburd
Building How I Invest: Podcasting, Venture Deal Flow, and the Long Game with David Weisburd
I recently sat down with my friend David Weisburd, host of How I Invest, for a conversation about podcasting, venture capital, relationships, and what it takes to play the long game.
David took a very intentional approach to building How I Invest. He committed to the podcast for at least a decade and used it to create something much bigger than a media platform: a network of investors, entrepreneurs, and relationships that continues to compound.
We talked about the challenges of building from zero, why you have to “pick your hard,” how the businesses we build can change us, and why long-term relationships may be one of the most valuable forms of alpha in venture.
Pick Your Hard
One of David's simplest, and most compelling, ideas was that you have to pick your hard.
When he decided podcasting was his hard, he knew the early years would be difficult. Booking LPs was challenging, compliance teams had concerns, and there was no guarantee the show would gain traction.
Instead of judging the idea after a handful of episodes, David committed to the game for a decade.
That's an important lesson for entrepreneurs. Early traction can be misleading, and many worthwhile businesses take years to develop. Sometimes commitment has to come before the results.
The Business Works on You
David also shared an idea that really stuck with me: while you work on a business, the business works on you.
Podcasting has forced David to become more self-aware. He watches his episodes, studies how he communicates, and constantly looks for ways to improve.
That feedback loop applies to entrepreneurship as well. Customers, employees, investors, and the market are constantly giving us information. The best founders aren't simply building a business, they're allowing the process of building to change them.
Podcasting as a Network
For David, How I Invest has become a powerful combination of information and relationship “alpha.”
Every conversation gives him access to someone else's experience and thinking. But the relationships may be even more valuable.
A podcast creates permission to have deeper conversations. You can ask about someone's motivations, decision-making, failures, and worldview in ways that might feel unnatural in a traditional business meeting.
Over time, those conversations compound.
The podcast itself also benefits from network effects: better guests create better content, which drives more attention, which attracts better guests.
The challenge is getting started. You don't have the audience or credibility yet, and the people you most want to reach have little reason to say yes.
David built that credibility one episode at a time.
The Winner Mindset
We eventually moved from podcasting into venture capital and what separates successful emerging managers from those who struggle.
David described this as the difference between a winner mindset and a victim mindset.
A winner mindset isn't about pretending everything is going well. It's about deciding to stay in the game and figuring out how to adapt when conditions get difficult.
For an emerging manager, that might mean changing a fund structure, raising a smaller vehicle, or developing another source of value while continuing to pursue the core strategy.
The question isn't whether the environment is difficult. It's whether you can build something resilient enough to keep going.
Founder-Product Fit
We also discussed an idea I think deserves more attention: founder-product fit.
We spend a lot of time talking about product-market fit, but founders should also ask whether they are uniquely suited to build the business in front of them.
David's background across entrepreneurship, finance, investing, and psychology has shaped what he's building today. His experience is unusually aligned with his product.
That's not necessary for success, but the broader lesson is powerful: understand your strengths and build around them.
Self-awareness isn't just a personality trait. It can be a competitive advantage.
Relationships Compound
Perhaps my favorite part of the conversation was our discussion about long-term relationships.
Everyone says relationships compound. Far fewer people actually behave that way.
In venture, the best relationship decision isn't always the one that maximizes the economics of today's transaction. Sometimes it's helping someone before there's an obvious benefit, making an introduction, sharing information, or simply being useful.
Those actions may not produce an immediate return. But over a decade, they can create opportunities that transactional thinking never would.
Play the Infinite Game
Ultimately, that's what I took away from my conversation with David.
Whether you're building a podcast, a startup, a venture fund, or a career, the most interesting opportunities are often infinite games.
You don't win once and walk away. You keep learning, improving, building relationships, and adapting.
David committed to How I Invest because he was willing to play that game for the long term. I think there's a broader lesson for all of us:
What is the hard you're willing to choose—and are you committed enough to keep playing when it gets harder?
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