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Immigration status shouldn’t depend on a paperwork nightmare.
But for many immigrants, navigating the US immigration system means months of uncertainty, complicated filings, and life-changing consequences when something goes wrong.
Aizada Marat knows this firsthand. After experiencing the system’s challenges herself, she founded Alma to transform how immigration legal services are delivered.
Aizada joins me on the pod to discuss how Alma combines AI, technology, and experienced attorneys to make immigration law more efficient, transparent, and predictable.
We explore:
→ Why AI could make legal services more human
→ Where AI will - and won’t - disrupt the legal industry
→ How companies are rethinking immigration as they compete for talent
→ Why skilled immigration matters to America’s innovation economy
Special thank you to Aizada for joining the pod and to Alma for all of the amazing work they’re doing.
⏱️ Chapter Markers:
00:00 — Introduction: Meet Aizada Marat and Alma
00:51 — What Is Alma? Rethinking Immigration Law
02:15 — From Cooley to Alma: A Founder’s Personal Immigration Journey
05:14 — Why Immigration Is a Systemic Challenge
06:15 — The Problem With Traditional Immigration Legal Services
06:46 — How AI Makes Legal Services More Human
10:26 — Alma’s Model: Technology Meets Experienced Attorneys
13:03 — Measuring Success: Quality, Speed, and Transparency
16:21 — Which Parts of the Legal Industry Are Most Vulnerable to AI?
20:41 — Why AI Will Augment Lawyers Rather Than Replace Them
24:18 — Immigration as a Competitive Advantage in the AI Talent Race
28:15 — Rethinking the Debate Around Skilled Immigration
29:56 — The Connection Between Immigration, STEM, and Innovation
38:32 — Aizada’s Policy Priorities: Digitizing USCIS
40:42 — Closing Thoughts
LINKS
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
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:
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
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:
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:
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:
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:
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:
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:
Is the global economy stronger than it looks or more fragile beneath the surface? If you’re trying to reconcile booming markets with rising geopolitical risk, this week’s episode brings an important perspective.
I sat down with Chris Zhang, Partner & CIO of Ascend Interplay, to break down the real forces shaping 2026:
Big thanks to Chris for a thoughtful, data-driven discussion.
⏱️ Chapter Markers
00:00 – Welcome & Why 2025 Defied Gravity
02:00 – Global GDP Surprise & Market Performance
03:30 – The Structural Bull Market in Gold & Silver
07:45 – When Would Gold Actually Fall?
10:00 – 2026 Outlook: Cautiously Constructive
11:45 – AI’s Real Impact on Productivity & Labor
14:30 – Middle East Conflict & Oil Markets
17:15 – Are Trade Wars Really Over?
19:30 – Structural Protectionism & Supply Chains
22:00 – The Americas Strategy & Regional Integration
26:30 – U.S. Debt: Is There a Real Solution?
29:45 – The Fed, Growth & Kevin Warsh’s Role
32:45 – Final Takeaways for 2026
Links:
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