Refounding: Why this $80m founder quit as CEO, and what it says about the future of startups

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1. 

   S5 · E18 · 8 Jun 2026 · 43 min

   How to fix a 'broken industry' (w/ Brandon Weber – Nava Benefits, VTS, Hightower)

   Every founder gets a version of the same advice: don't pick a fight with an entrenched industry. The incumbents have the relationships, the regulatory cover, the deep pockets - you'll bleed out trying. But some of the most interesting companies of the last decade were built ignoring that advice, winning over markets that were nearly impenetrable. In this episode, Yaniv Bernstein is joined by Brandon Weber - co-founder and CEO of Nava Benefits, a Series C-funded AI-powered health benefits brokerage. Before Nava, Brandon co-founded Hightower, a commercial real estate startup that merged with…

2. 

   S5 · E17 · 1 Jun 2026 · 53 min

   Why Gary Lo's product strategy has evolved in the era of DIY software

   What if writing software became as easy as taking a selfie? This episode, Yaniv Bernstein sits down with Gary Lo - founder of OpenBA and one of the sharpest AI-and-startups thinkers Yaniv knows - to discuss the concept of 'selfie software': disposable, hyper-personal, AI-generated tools that anyone can create for themselves, with no hand-written code. AI-generated tools like these are changing the startup landscape. While founders now have more tools at their disposal, it's now necessary than ever to create a product that truly disrupts the market. Gary and Yaniv discuss all of this and…

3. 

   S5 · E16 · 25 May 2026 · 57 min

   Author Eric Ries (The Lean Startup) on how to build an incorruptible company

   Most founders set out to build something that matters: a company that’s aligned with their mission, now and forever. But what if the very systems we use to build ‘real’ companies are the thing that corrupts them? In this episode, Yaniv Bernstein is joined by Silicon Valley legend Eric Ries author of the era-defining 'The Lean Startup', founder of the Long-Term Stock Exchange, and now the author of a provocative new book, 'Incorruptible: Why Good Companies Go Bad and How Great Companies Stay Great'. Eric makes the case that corruption is a structural problem, rather than a failing of the…

4. 

   S5 · E15 · 21 May 2026 · 39 min

   FEED DROP: Could AI Make Capitalism Better? Henrik Werdelin Is Optimistic (from FAFO with Dan Blumberg)

   This is a bonus feed drop from Dan Blumberg's podcast 'Future Around and Find Out' (FAFO), winner of the 2026 Webby Award for Best Technology Podcast. If you like what you hear, check out FAFO at https://www.futurearound.com/ Original description: Henrik Werdelin is one of my favorite entrepreneurs. He’s founded and incubated several unicorns, most notably BARK, the dog happiness company. Henrik himself is a pretty happy guy — an optimistic guy who likes to ask what could go right? — and on the day we recorded (a few months ago as I was squirreling away interviews for the podcast relaunch),…

5. 

   S5 · E15 · 18 May 2026 · 1 hr 5 min

   The Science of Scaling: Using data to scale your startup perfectly w/ Mark Roberge

   Most founders treat 'scale' like a switch you flip after raising a round: hire 14 reps, 10x the ad spend, and pray. About half scale too early and burn the runway, while the other half scale too late and get caught by a more aggressive competitor. Almost nobody can tell you, in measurable terms, when they're actually ready. In this episode, Yaniv Bernstein is joined by Mark Roberge - founding CRO at HubSpot (where he scaled the company from $0 to $100M ARR), senior lecturer at Harvard Business School, cofounder of Stage 2 Capital, and author of the new book 'The Science of Scaling'. Mark…

6. 

   S5 · E13 · 4 May 2026 · 38 min

   Adapting your startup to an AI-native world (w/ Marlon Nichols)

   Many AI startups funded in the last 18 months won't last three years - so what makes a business durable today? Yaniv Bernstein is joined by Marlon Nichols, co-founder and managing general partner of MaC Venture Capital - one of the most active seed-stage AI investors in the market, having scaled MaC to over $600M AUM across three funds in just four years. Marlon's portfolio includes Pipe, Stoke Space, Thrive Market, Chef Robotics, and exits like Wonder Dynamics to Autodesk and Gimlet Media to Spotify. In this conversation, Marlon uses his industry experience to explain the biggest threats to…

7. 

   S5 · E12 · 27 Apr 2026 · 29 min

   How the best founders balance fear and hope

   Being a founder has always meant dreaming big while keeping a close eye on potential trip-ups, and in the age of AI, finding and maintaining that balance is more important than ever. Today, Yaniv Bernstein talks about the importance of getting that balance right. Using deep insight and decades of industry experience, he discusses why now is the time for founders to be more ambitious than ever before - while identifying threats to success and keeping a keen, near-paranoid eye on them. In this episode, you will: Understand why ‘paranoid optimism’ has always been the founder superpower, and why…

8. 

   S5 · E11 · 20 Apr 2026 · 50 min

   Same As Ever: 7 rules that HAVEN'T changed about building great startups (w/ Amir Shevat)

   Between AI shaking up the industry, geopolitical upheaval, and unpredictable capital, being a founder has never been more confusing. So what advice, if any, is still relevant? In this episode, Yaniv Bernstein is joined by Amir Shevat (Silicon Valley developer platform veteran and now General Partner at Darkmode Ventures) to answer exactly that. Focusing on what isn't changing rather than what is, Amir walks through seven truths of startup building that have become more important in the age of AI. In this episode, you will: Discover why AI-generated sales outreach is backfiring, and why…

9. 

   S5 · E10 · 13 Apr 2026 · 48 min

   Surviving the AI SaaSpocalypse: Will AI kill your startup? w/ Scotty Allen

   Will AI kill your startup? For a lot of startups, probably yes. But which ones? And more importantly, how do you make sure yours isn't one of them? Yaniv Bernstein is joined by returning guest Scotty Allen (bootstrapper, founder of The Product Bus, and startup strategist extraordinaire) to reason through one of the most pressing questions of 2026: how do you build a startup to survive the SaaSpocalypse? They discuss why this AI wave is more of a threat to tech startups than Google and Facebook ever were, and why the B2B/B2C distinction has never mattered more. Along the way, Yaniv discusses…

10. 

    S5 · E9 · 6 Apr 2026 · 29 min

    ‘Unlearning’ with Yaniv: Why founders need to rewrite outdated, radioactive mindsets

    You may have spent years (or even decades) building your expertise. But is any of it still relevant? And how much of it is an active detriment to your startup? In this special solo episode, Yaniv Bernstein delivers a no-guest monologue on the most critical skill any founder can develop right now: ‘unlearning’. Drawing on Morgan Housel's ‘Same as Ever’; real-world examples from his own startup, Vera; and frameworks for rebuilding beliefs from the ground up, Yaniv makes the case that obsolete knowledge is as bad as radioactive waste actively distorting your decisions. In this episode, you…