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 @kevinwtung , 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.

Socks are the #1 most requested item at homeless shelters. Dave Heath turned that single fact into @BOMBAS . The brand has 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. He reverse-engineered an exceptional product from a mission. He learned to test before betting. And he protected the brand as it grew. 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 effect, going from $800K to $2M in revenue in the six weeks after airing. • The expensive lesson of expanding into adjacent products too fast and the MVP-testing discipline that replaced it. • Radical-ish transparency. • 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. Big thanks to Dave for coming on the pod and sharing the playbook (and the mindset) behind Bombas.

Anduril: $5B raise, $61B valuation. The same week was the largest defense-tech VC week on record. Silicon Valley is re-enlisting — and it's worth remembering the Valley was born defense (Fairchild → Minuteman, Apollo → ~60% of all ICs, DARPA → ARPANET). Then it drifted. Cold War wound down in '91, the web arrived in '93, and by the late 2000s the dominant Valley archetype — Google, Facebook, Twitter — had near-zero federal exposure. The near-divorce hardened in 2018, when 3,000+ Googlers signed the letter that killed Project Maven. The reversal came quietly: Palantir (In-Q-Tel → 2020 IPO → $300B+), Anduril (founded 2017 to rebuild a prime the Valley way), SpaceX (the Pentagon's biggest launch provider). Today's Stanford/MIT grads compete for the offers that were career suicide in 2018. What changed? A hot geopolitical backdrop, DoD on-ramps (Replicator, OTAs) that fit startup timelines, and a founder generation that decided ceding the frontier was the bigger ethical risk. The $5B isn't the story. The story is there's no longer a contradiction. Full piece: interplay.vc/blog/silicon-va…

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.