Founder Mode

EPISODE 80Keith Wasserman started with a single $140,000 fourplex and has since completed billions of dollars in real estate transactions as co-founder of Gelt, all while holding to one rule: protect capital first. In this episode, Kevin and Jason talk with Keith about why today's commercial real estate downturn is in some ways harder than 2009, with apartment values down 25 to 50 percent, and why the best time to deploy capital is when everyone else is scared. Keith explains why 95 percent of his portfolio sits on long-term fixed-rate debt, why the wealthiest real estate owners regret every sale, how illiquidity protects investors from their own emotions, and how real estate really stacks up against the S&P 500. He also shares why he's personally calling all 1,800 of his investors one-on-one, how he built a team around his blind spots (he doesn't even use Excel), and why Gelt is launching its first fund to buy newer apartments below replacement cost in oversupplied markets like Austin.CHAPTERS00:00 – Why Fear Is the Best Time to Buy00:36 – Investing Through Uncertainty02:39 – Meet Keith Wasserman03:16 – The $140K Fourplex That Started It All04:51 – Scaling From Four Units to Hundreds05:58 – Fixed-Rate Debt and Protecting the Downside07:15 – Get Rich Slow: Why the Wealthy Never Sell10:21 – Why This Cycle Is Harder Than 200911:50 – What Investors Misunderstand About Today's Market12:49 – Real Estate vs. the S&P 50015:52 – Calling 1,800 Investors One-on-One19:50 – Building a Team Around Your Blind Spots21:59 – Gelt's First Fund and the Austin Opportunity24:24 – Founder Mode Top 5 TakeawaysLINKSConnect with Keith WassermanGelt Venture Partners • LinkedIn • X/TwitterStay Connected with Founder ModeStay Connected with Founder ModeSubscribe to our newsletterConnect with KevinLinkedIn • X/TwitterConnect with JasonLinkedIn • X/Twitter

EPISODE 79In this solo episode, Kevin Henrikson and Jason Shafton dig into a turning point for AI. In 2025, agent misbehavior lived in staged lab experiments, but in 2026, at least four labs have admitted their agents hacked real companies. Jason walks through the recent incidents, from malicious packages on RubyGems and Gemini going after three real companies to an agent breaching Australia's Medicare statistics portal. The two debate how worried founders should be, whether an emergency brake already exists and who gets to pull it, and what to do when the labs can see your data, outspend you, and ship your product. Plus: why consulting is pivoting to AI implementation, OpenAI's $23 million Navier-Stokes heist, and how an AI agent fueled Jason's first marathon by ordering his carbs on DoorDash.CHAPTERS00:00 – Cold Open00:43 – Jason's First Marathon and the AI Agent That Ordered His Carbs04:42 – 2026: The Year AI Agents Hacked Real Companies06:18 – How Worried Should We Be?07:35 – Inside the Incidents: RubyGems, Gemini, Medicare and More12:09 – Emergency Brakes: Who Gets to Pull Them?15:40 – Will the AI Labs Eat Your Business?19:28 – Is the Age of the Consultant Over?20:49 – The $23 Million Navier-Stokes Heist23:52 – Has a Robot Run a Marathon Yet?24:50 – Founder Mode Top FiveLINKSStay Connected with Founder ModeSubscribe to our newsletterConnect with KevinLinkedIn • X/TwitterConnect with JasonLinkedIn • X/Twitter

EPISODE 78Claire Stapleton spent twelve years at Google and YouTube writing the company's story, from ghostwriting for Larry Page to running YouTube's social media, before she co-organized the 2018 Google Walkout, when 20,000 employees walked out over how the company handled sexual harassment. Kevin and Jason, who started at Google a year before Claire, talk with her about her new memoir, Don't Be Evil. They cover what happens when a company that sells meaning as a perk discovers that meaning is expensive, how Google+ got tied to everyone's bonus, why YouTube's marketing org ended up marketing to its own executives, and why tech workers who once petitioned and walked out have gone quiet. Claire also shares a story that didn't make the book, describes the subway ride home after leaving, explains what it was like to read talking points written about herself, and tells us why she still calls Google a "low key greatest company."CHAPTERS00:00 – Cold open00:41 – Is culture load-bearing or just marketing?04:07 – Selling meaning as a perk05:42 – Ghostwriting Larry Page and the cure-death era08:35 – Google+ and the corporate bonus10:29 – When the story cracked: Creative Lab13:18 – YouTube and the brand vulnerability briefing15:54 – Was advertising the real mission all along?18:10 – Marketing to executives instead of the public21:31 – Maven, the walkout, and why workers went quiet25:21 – Would she organize the walkout again?28:08 – The subway ride home32:06 – Where to find Claire and Don't Be Evil33:13 – The Founder Mode FiveLINKSConnect with Claire StapletonDon't Be Evil • Tech Support • LinkedIn • X/Twitter • InstagramStay Connected with Founder ModeSubscribe to our newsletterConnect with KevinLinkedIn • X/TwitterConnect with JasonLinkedIn • X/Twitter

EPISODE 77Viktor Petersson and Alex Finn were two of Founder Mode's earliest guests, and they're back with opposite answers to the biggest question in AI right now: how much should you trust your agents? Viktor, founder of Sbomify and co-founder of Screenly, routes every agent through an identity proxy that gives it just enough access to do its job, and it took him a long time to let even his human assistant into his email. Alex, founder and CEO of Henry Intelligent Machines and creator of Creator Buddy, gave his agents access to everything and says it changed his life. They get into how each of them starts the day with AI, why Alex switches to a new favorite agent almost every week, whether anyone at OpenAI is actually reading your email, and why skills and context stores might be a short-term fix. Alex explains why he's holding back the Henry launch to beat churn, why always-on ambient AI will only be possible with local models, and why a 9 a.m. and a 2 p.m. meeting cooks his whole day, while Viktor makes the case that Apple could win the long game and that reviewing agent output is the new bottleneck. They close on why one raised money for distribution while the other stays bootstrapped to avoid getting locked into a roadmap, plus a lightning round on the most overrated thing in AI and the one thing they'll never hand to an agent.CHAPTERS00:00 – Cold open: "What's your concern?"01:51 – Cage the agents vs. release the agents02:42 – How they start the day with AI05:14 – A new favorite agent every week07:28 – Would you give AI your email?11:44 – Building a company with a tiny team16:53 – Are skills and context stores a short-term fix?18:54 – Why Alex isn't rushing to ship Henry21:04 – Local models vs. frontier models23:31 – Ambient AI and hacking your hardware27:49 – Babysitting agents: the new bottleneck30:02 – Context switching and the perfect week31:17 – Raising money vs. bootstrapping35:07 – Lightning round39:28 – Founder Mode top fiveLINKSConnect with Viktor Peterssonvpetersson.com • LinkedIn • X/Twitter • GitHub • Nerding Out with Viktor Podcast • Sbomify • Screenly • Little Snitch Meets 1Password for AI AgentsConnect with Alex FinnYouTube • X/Twitter • Newsletter • Vibe Coding AcademyStay Connected with Founder ModeSubscribe to our newsletterConnect with KevinLinkedIn • X/TwitterConnect with JasonLinkedIn • X/Twitter

EPISODE 76JJ Zhuang, co-founder and CEO of Pretty Good AI, returns to Founder Mode to answer for the predictions he made on the show over a year ago. Kevin and Jason had Claude grade all ten, and JJ defends his record on hiring generalists over specialists, how much code AI is really writing, why taste is the one thing you can't train into a model, and why slide decks are dead when you can just build the thing. He finishes 6.5 for 10, which beats the weatherman, and points to the release of Opus 4.6 as the moment things that used to not work suddenly started working. In the second half, JJ looks ahead: why Pretty Good AI is skipping the "sell the same widget a thousand times" playbook to become the AI team for healthcare practices, how to build guardrails around AI that's confidently wrong, why the human work that's left will be 100% hard work, how the team keeps protected patient data away from AI agents, and how a lean team can win a crowded healthcare AI market.CHAPTERS00:00 – Cold Open: Why Not Just Solve All Your Problems?00:31 – JJ Returns: Grading 10 Predictions One Year Later01:58 – Generalists vs. Specialists: Who Should You Hire?04:39 – Is AI Really Writing Half of All Code?07:28 – Taste, Comprehension, and the Human Edge09:58 – Instant Prototypes, Fast Software, and the Death of Slide Decks12:39 – Directing AI and the Most Overhyped Buzzword14:32 – Overhyped or Underestimated? The Opus 4.6 Moment17:09 – The Scorecard: 6.5 for 1018:00 – Pretty Good AI's Big Bet: Solve Every Problem20:02 – What Success Looks Like: Becoming Your Customers' AI Team20:39 – Designing Around AI That's Confidently Wrong22:20 – Where the Line Between AI and Humans Moves Next24:09 – Building on Models That Change Every Few Months25:58 – Compliance When Your Team Is Agents28:23 – What Patients Notice First30:17 – How a Lean Team Wins a Crowded MarketLINKSConnect with JJ ZhuangPretty Good AI • LinkedIn • X/TwitterStay Connected with Founder ModeSubscribe to our newsletterConnect with KevinLinkedIn • X/TwitterConnect with JasonLinkedIn • X/Twitter