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

What happens when technology evolves faster than the venture capital model built to fund it?

In this episode, I sit down with my longtime friend Jenny Fielding, Cofounder and General Partner of Everywhere Ventures, to explore how venture capital is adapting to a world where competitive advantages can disappear faster than ever.

We discuss what it takes to raise a pre-seed round in today’s market, why traditional assumptions around defensibility are being challenged, and how AI is reshaping the economics of software companies.

Jenny also shares lessons from her time as a Managing Director at Techstars and explains why Everywhere Ventures built a community-driven approach to investing — leveraging founder networks and real-time market insight to identify breakout companies at the earliest stages.

Whether you’re a founder raising capital, an investor navigating a changing market, or simply curious about where technology is headed, this conversation offers a practical look at how venture is evolving for the next generation of companies.

Special thanks to Jenny for joining the show and sharing her perspective on the future of venture.

⏱️ Chapter Markers:

00:00 - Introduction and studio acoustics

01:05 - Generalist investing shift

02:09 - Redefining modern pre-seed criteria

04:26 - Global Slack diligence network

06:31 - Check sizing and syndicate structures

07:20 - Conviction-led turnaround speeds

09:21 - Venture capital's existential model crisis

11:48 - Defensibility against quantum technology

13:17 - Sourcing wisdom from international founders

16:01 - Evaluating the accelerator landscape

17:26 - Clear milestones for founder success

19:39 - Moving targets in the Series A gap

21:05 - Evolution of emerging tech hubs

23:32 - Retaining global talent via immigration reform

Links:

• Jenny Fielding: LinkedIn, X
• Everywhere Ventures: Website, LinkedIn, X
• Interplay: Website, LinkedIn, X
• MPD: LinkedIn, X

Socks are the #1 most requested item at homeless shelters. Dave Heath turned that single fact into Bombas — a one-for-one apparel brand that's donated over 200 million items of clothing and built a billion-dollar business along the way. What makes Dave a builder worth studying isn't just the scale; it's the discipline behind it: reverse-engineering an exceptional product from a mission, learning to test before betting, and protecting a brand as it grows.

In this episode, I sit down with Dave to break down:

• How he reverse-engineered an "exceptional product" from a donation mission — and brought athletic-sock innovation to the mass market

• The Shark Tank breakout: from $800K to $2M in revenue in the six weeks after airing — and why ~20% of customers still affiliate Bombas with the show

• The expensive lesson of expanding into adjacent products too fast — and the MVP-testing discipline that replaced it

• Why the "obvious" extensions (underwear, t-shirts) underperformed while a sleeper bet (slippers) became 20% of the business

• Radical-ish transparency: telling the whole company about a planned IPO and trusting adults to keep it quiet — and they did

• The mark of a great founder: the self-awareness to evolve his own role as the company scaled, and how he screened his successor for humility

• How Bombas is approaching AI — getting the whole company trained on Claude and Claude Code, and why building AI as a competency beat chasing shiny enterprise tools

Big thanks to Dave for coming on the pod and sharing the playbook — and the mindset — behind Bombas.

⏱️ Chapter Markers:

00:00 — Intro. An epic New York brand story

01:05 — What is Bombas? The one-for-one mission and 200M+ items donated

02:37 — Reverse-engineering an exceptional product. Athletic-sock innovation goes mass market

04:49 — The story before the story. An entrepreneurial upbringing and the "candy dealer" founder type

09:00 — The Shark Tank breakout. From $800K to $2M and the deal with Daymond

11:48 — Expanding beyond socks. The costly lesson of adding complexity too fast

14:27 — How to filter adjacent products. The slipper sleeper hit and MVP-testing over big bets

18:00 — Radical(-ish) transparency. Trusting the team with the data and a planned IPO

19:39 — Evolving the founder's role. Screening a successor for humility as the company scales

24:03 — Life beyond the day-to-day. Family. Hobbies. And a retreat full of founder regrets

26:14 — Staying a united front. Backing the team without undermining them

27:50 — AI as a tidal wave. Training the whole company on Claude. Competency over shiny objects

31:20 — The pace of change. Why this revolution moves in months not centuries

31:56 — The wand question. Cutting waste out of fashion and apparel

34:35 — MPD's closing thoughts. The discipline behind a brand built to last

Links:

Dave Heath: LinkedIn

Bombas: Website, LinkedIn, X

Interplay: Website, LinkedIn, X

MPD: LinkedIn, X

Cats are 40% of the pet market, but are somehow still chronically overlooked. Every innovation goes to dogs first. Even your vet's office is built for dogs first. Matt Michaelson, cofounder and CEO of Smalls, and his team have built an incredible cat-first brand precisely because of that blind spot.

In this episode, I sit down with Matt to break down:

• Why the cat industry is structurally underinvested (which includes VCs simply saying "I don't really like cats")

• What "human-grade" actually means for pet food — and the sustainability trade-offs nobody talks about

• Ingredient splitting: the regulatory hack that lets pet brands disguise what's actually in the bag

• "Wrestling in the mud": a feedback culture where every hire is expected to disagree

• Founders Pledge, and why committing 5% early changes the giving conversation later

Big thanks to Matt for coming on the pod and sharing the playbook behind Smalls.

⏱️ Chapter Markers:

00:00 — Why cats keep getting overlooked

01:05 — What is Smalls? Cat-first brand, human-grade nutrition

02:09 — What "human-grade" actually means (and the sustainability trade-off)

04:26 — Health impact: allergies, ingredient splitting, and the regulatory hack

06:31 — Why Matt chose cats: the market psychology nobody's pricing in

07:20 — Why every VC and pet brand defaults to dogs first

09:21 — From growth marketing to founder: building demand in a commoditized stack

11:48 — Emerging channels worth watching (and why DTC is just a channel, not a model)

13:17 — AI-native orgs: how the team uses AI without becoming a tech company

16:01 — Human-supervised AI teams and what entry-level jobs look like now

17:26 — "Wrestling in the mud": the air-grievances feedback culture

19:39 — Founders Pledge: committing 5% early changes the whole conversation

21:05 — Ingredient transparency: percentages on the label, fixing the labeling game

23:32 — MPD's closing thoughts on the cat opportunity

Links:

• Matt Michaelson: LinkedIn
• Smalls: Website, LinkedIn, X
• Interplay: Website, LinkedIn, X
• MPD: LinkedIn, X

Venture studios are quietly becoming one of the most effective models for company creation, but most people still don't understand what happens inside one.

For this podcast episode I sat down with Andy Bilinsky, Partner at Interplay leading our Studio, to break down exactly how we build companies from the ground up.

During our conversation, we covered:

• What a venture studio actually is and how it differs from traditional VC
• Why do we research industries deeply before ever writing a business plan
• The role of operating partners as true co-founders
• Why second- and third-time founders are choosing to build with a studio instead of going solo
• How Interplay went from 3 new companies in Q4 2025 to targeting 10+ in 2026

Big thanks to Andy for pulling back the curtain on how we build. We’re grateful to have him here at Interplay.

⏱️ Chapter Markers:

00:00 Introduction to Andy Bilinsky

01:15 Andy's Entrepreneurial Background

03:30 Early Career: Hyper-Growth at Haute Look

05:45 BeachMint, Science Incubator & Chirp Ads

08:00 Launching Lensable From Scratch

09:30 Why Andy Joined Interplay

13:00 What Is a Venture Studio?

15:30 Interplay's Thesis-Driven Approach

18:00 The Role of Operating Partners

20:30 What Makes a Great Studio CEO

24:00 Why Successful Founders Don't Go Solo

27:30 The Value of a Firm as Co-Founder

30:00 Administrative Support & De-Risking

33:00 Distributed Teams & Geographic Flexibility

35:00 Studio Growth: From 3 Companies to 10+

Links:

• Andy Blinsky: LinkedIn
• Interplay: Website, LinkedIn, Twitter
• MPD: LinkedIn, Twitter

Private credit has exploded into a trillion-dollar asset class, but most people outside finance still don’t understand how it works.

I sat down with Ivan Zinn, founder of Atalaya Capital Management and now part of Blue Owl Capital, to unpack the real mechanics behind the private credit market. Few people have a clearer view of how capital flows through the economy.

During our chat we unpack:

1. What private credit actually is
2. Why banks pulled back after the Global Financial Crisis
3. How private lenders stepped in to finance everything from consumer loans to equipment, infrastructure, and fintech platforms
4. Where entrepreneurs could build meaningful companies by modernizing the infrastructure behind asset management.

Big thanks to Ivan for sharing such a thoughtful and practical perspective on the evolving capital markets ecosystem.

⏱️ Chapter Markers

00:00 Introduction to Ivan Zinn

01:40 What Private Credit Actually Is

03:05 Asset-Based Lending Explained

04:36 Why Banks Don’t Make These Loans

08:11 How Private Credit Filled the Financing Gap

09:19 Ivan’s Journey into Credit Investing

11:49 Why Scale Matters in Private Credit

16:32 Is There Still Room for Small Credit Managers?

18:35 The Rise of Fintech-Driven Lending Models

19:29 Biggest Mistakes New Credit Managers Make

24:46 What CEOs Get Wrong When Raising Debt

29:08 Aligning Expectations Between Lenders and Founders

31:16 Why Private Credit Is Still Technologically Behind

35:30 Massive Opportunities for Fintech Builders

40:06 Selling Atalaya Capital Management to Blue Owl

42:30 Should Asset Managers Go Public?

44:58 Final Advice for Fintech Entrepreneurs

Links:

1. Ivan Zinn: LinkedIn
2. Interplay: Website, LinkedIn, Twitter
3. MPD: LinkedIn, Twitter