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

Most people only see the front end of fintech. The app. The card. The payment. But underneath that experience is an enormous amount of infrastructure and some of fintech’s biggest opportunities are hiding there.

Rory O’Reilly, cofounder and CEO of Knot, joined me on the pod to talk about how Knot is rewiring fintech and transforming financial connectivity.

We dive into:

• Why keeping a card “top of wallet” is harder than it sounds.
• The infrastructure required to connect financial institutions with thousands of merchants.
• Why security and compliance are foundational, not afterthoughts, in fintech.
• Where blockchain and stablecoins could fit into the financial stack.
• Rory’s unconventional path from selling shoes with his family to building fintech companies with his brother.

What I particularly enjoyed about this conversation is that Knot is tackling a problem most consumers don't even realize exists. The biggest innovations in fintech may not be the products we see, they may be the infrastructure quietly making everything work.

🎙️ Listen to the full conversation with Rory O’Reilly here:

⏱️ Chapter Markers:

01:12 — What Knot does: card-on-file updates, top-of-wallet

04:08 — The consumer pain: lost/expired cards and sticky subscriptions

06:20 — Why issuers/fintechs care: interchange and activation

09:05 — Go-to-market: selling to issuers; merchant API approach; 100M calls

12:44 — Security/compliance first: fractional CISO Brian Costello (ex-Yodlee)

16:18 — The fintech iceberg: why infra disruption is a long game

19:45 — Blockchain at the gate: stablecoins, Cash App's Lightning, backend use cases

24:58 — Founder origins: family hustle and resilience

30:36 — Harvard, Thiel Fellowship, gifs.com virality

35:52 — ICOs, ETH windfall and crash, and hard lessons

41:07 — Building with his brother: roles, trust, zero drama

45:30 — Closing takeaways

LINKS

• Rory O'Reilly: LinkedIn, X
• Knot: Website, LinkedIn, X
• Interplay: Website, LinkedIn, X
• MPD: LinkedIn, X

Every founder I know is asking the same question: "How should we actually implement AI across our company?"

The reality is that every playbook will require customization, but there are clear patterns beginning to emerge.

In this episode, Chetan Narain, Cofounder of Pepper, joins me and my colleague, Interplay Senior Partner Kevin Tung, to share how Pepper is integrating AI across its products and organization - and the lessons they've learned along the way.

We discuss:

• Where vertical SaaS ends and vertical AI begins

• AI agents and guardrails

• Organizational redesign

• How to move fast without creating chaos

If you're building a company and thinking beyond AI features toward AI transformation, I think you'll enjoy this conversation.

⏱️ Chapter Markers:

00:00 — Intro — Implementing AI across your company and why it matters now

01:23 — Where vertical SaaS ends and vertical AI begins: dashboards → autonomous agents

03:36 — Pepper 101: the $1T food distribution opportunity

05:37 — Pricing agents: moving from recommendations to action

08:42 — Trust, autonomy, and guardrails for mission-critical workflows

09:33 — ROI you can prove: GP lift and attribution clarity

11:25 — Experiments that broke: letting non-tech teams ship code

14:21 — Pepper's "product build system": AI-reviewed PRDs and prototypes

19:22 — Organizational design: single-threaded ownership vs. diffusion

23:03 — Speed traps: building 4 prototypes ≠ faster outcomes

24:22 — Kevin Tung on logging mistakes and compounding intelligence

26:10 — A/B testing as a sandboxed guardrail

27:02 — Chetan's path: Google PM to first PM of Uber Eats

29:37 — COVID pivot: Pepper Pantry hits $10M run rate in a week

32:57 — Distributor-first model: white-labeled apps and trust

34:33 — If king for a day: accelerating tech adoption in food

36:31 — Early adopters and tailwinds across 20k+ distributors

38:11 — Wrap and takeaways

Links:

• Chetan Narain: LinkedIn

• Pepper: Website, LinkedIn

• Interplay: Website, LinkedIn, X

• MPD: LinkedIn, X