Founders Don't Get Sick Days

EPISODE 82In this solo episode, Kevin and Jason break down how founders can travel constantly without wrecking their sleep, health, or productivity. Jason shares his contrarian experiment of staying on Pacific time for an entire trip to Amsterdam, while Kevin explains how he uses the Timeshifter app to reset his circadian rhythm. Kevin then unpacks the $20 Amazon backpack he's lived out of for years, including his never-unpacked everyday-carry kit, the cold and flu packs that keep him working when he's under the weather, and the single 280W charger that powers every device he owns. They also debate whether founders still need an admin now that AI agents can find routes and recover forgotten travel credits, why Kevin only books one-way tickets, how a Craigslist Prius explains his loyalty to airline status, the "Starlink is down" trick for getting the best Wi-Fi on the plane, and Sam Parr's "I'm in your city" power move for landing meetings with hard-to-reach people.CHAPTERS00:00 – Cold Open: The Craigslist Prius00:45 – Why You Should Never Travel with a Podcast Mic02:05 – Beating Jet Lag: The Amsterdam Experiment05:26 – Inside Kevin's $20 Travel Backpack08:39 – One Charger and No Devices in the Bedroom10:43 – Do Founders Still Need an Admin to Book Travel?12:36 – The Carpool Lane Theory of Airline Status15:41 – Is There a Vacation Angle to Founder Travel?18:04 – The "Starlink Is Down" Trick18:38 – Land in a City, Fill the Calendar20:52 – Founder Mode Top FiveLINKSGear MentionedBackpack • Sleep Mask • GaN III ChargerStay Connected with Founder ModeSubscribe to our newsletterConnect with KevinLinkedIn • X/TwitterConnect with JasonLinkedIn • X/Twitter

EPISODE 81Kevin and Jason are back with their fourth best-of, revisiting the moments from episodes 61 through 80 they keep coming back to. This stretch leaned heavily into AI, from Kevin's 76 scheduled agents (and the one that reported success for eight days while doing nothing) to handing his inbox to Claude with a single instruction: do the right thing. But the clips that stuck were mostly about people. Anthony Ng Monica of Daily Body Coach on the burnout that forced him to stop, Jess Chan of Longplay on choosing to grow slower, Joe Speiser on the $100 million lesson of building on rented land, WP Engine founder Jason Cohen on why customers almost never cancel over price, and Keith Wasserman of Gelt personally calling all 1,800 of his investors when the market turned. Along the way, Alex Finn and Viktor debate giving an AI agent their email, Mohammad Moahid makes the case that a human still owns every decision an agent makes, Kiko Zang explains the mascot suit that let her be herself, and the guys share the AI outbound campaign that booked dozens of podcast guests and made zero dollars. The takeaway: hand off the work, keep the judgment.CHAPTERS00:00 – Welcome to the fourth Founder Mode best-of00:49 – Anthony Ng Monica: when your body makes the call02:32 – The AI stack nobody at the conference could name03:32 – 76 agents and the one that failed silently04:37 – Seek Sahib: the night he almost shut it all down05:46 – Joe Speiser: the $100M cost of building on rented land07:14 – "Do the right thing": letting Claude handle the inbox09:07 – Optionality, default alive, and a 93 sleep score10:17 – Jess Chan: the hard choice to grow slower11:27 – Alex Finn and Viktor debate giving AI their email12:49 – Jason Cohen: why customers don't cancel over price14:18 – AI agents don't get weekends15:39 – JJ's pitching machine rule for getting better at AI16:48 – Mohammad Moahid: accountability stays with humans17:41 – Will the AI labs eat your business?19:08 – The AI outbound campaign that made $021:20 – Kiko Zang and the mascot suit22:50 – Zimbra's free playbook and why it matters again24:31 – JJ Zhuang: where the AI and human line goes next26:15 – Claire Stapleton: YouTube and the ads machine27:41 – Keith Wasserman calls all 1,800 investors29:16 – Hand off the work, keep the judgmentLINKSStay Connected with Founder ModeSubscribe to our newsletterConnect with KevinLinkedIn • X/TwitterConnect with JasonLinkedIn • X/Twitter

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

EPISODE 75Kevin and Jason go solo on the week AI stopped asking permission. Jason opens with a Claude Code session that sent a Slack message to a client's CEO instead of drafting it, complete with a "sent from Claude" tag at the bottom, then offered to file a bug report about itself. That kicks off a run through what founders are actually paying for now: Jason's $800-a-month HubSpot bill and his plan to swap it for Dharmesh Shah's $1-a-month USpot, levels.io running a multi-million-dollar business on hand-coded PHP and a single server, and why the "SaaSpocalypse" is more nuanced than Twitter thinks. Kevin traces the freemium playbook back to Zimbra, where 98% of users never paid and the top 2% funded the company, and asks the question that hangs over the whole episode: how do you build trust in a market where everything can be free? They also get into Jason's agentic agency experiment, why succession is really about handing off jobs rather than titles, why nobody has built a marketing agent with taste yet, and the biological age scores every app is suddenly handing out, each one conveniently favoring its own algorithm.CHAPTERS00:00 – The Slack message Claude sent by itself00:39 – A dozen AI tools in a single day03:46 – $800 a month for a CRM04:26 – Dharmesh's $1 CRM and the SaaSpocalypse08:03 – Freemium after vibe coding: the Zimbra lesson10:32 – Building an agentic agency13:20 – Succession: hand off jobs, not titles16:33 – What AI still can't do in marketing19:18 – Biological age scores and walled-garden health data22:22 – Founder Mode top fiveLINKSStay Connected with Founder ModeSubscribe to our newsletterConnect with KevinLinkedIn • X/TwitterConnect with JasonLinkedIn • X/Twitter

EPISODE 74Kiko Zang spent more than half her life pretending to be someone else — born in China, sent alone to boarding school in New Zealand at 12, then to USC at 17, then back to China as the Chinese-looking person who couldn't hold an adult conversation in Chinese. Pretending, as she puts it, was a survival instinct that became one of her strongest skills. In this episode she traces that pattern from the classroom in China where she refused to rehearse a fake PTA lesson, through the years of self-censoring at work, to the full head-to-toe mascot costume she wore around crypto conferences — where, strangely, the expectations placed on a female founder vanished and she got to be more herself than she was without it. Now CEO of Chomp, she's building an app around the gap between what people say in public and what they actually believe in private, and she brings the receipts: 50,000 users, two million answers, and a question about saying "I love you" in the first month of dating that came back 93% green flag when nobody was watching — while every single player assumed it would be a coin flip. Kevin and Jason play a live pack on air, and the conversation moves into why honest human opinion may be the most valuable data set of the AI era, why there's no durable moat in consumer, and what Kiko learned after a co-founder breakup when her own team had to tell her she'd been muting herself in meetings. Her conclusion: the fear felt true not because it was real, but because she believed it was.CHAPTERS00:00 – More herself inside the suit00:40 – Know your audience or know yourself04:07 – Half a life spent pretending06:14 – The PTA rehearsal that got her sent abroad08:34 – The reluctant founder11:44 – The fursuit and who gets assumed to be the founder14:05 – Anonymity, honesty, and shared reality16:12 – Playing Chomp live19:24 – 93% green flag and the perception gap22:20 – Pluralistic ignorance and why consumer has no moat24:31 – Honest opinion as the data of the AI era27:50 – The co-founder breakup and fears that aren't real30:06 – Where to find ChompLINKSConnect with Kiko Zangchomp.fyi • LinkedIn • X/TwitterDownload ChompRedeem the Founder Mode listener offerStay Connected with Founder ModeSubscribe to our newsletterConnect with KevinLinkedIn • X/TwitterConnect with JasonLinkedIn • X/Twitter

EPISODE 73Mohammad Moahid has operated multiple companies across e-commerce, consumer electronics distribution, and real estate, and competed for Team Canada as an equestrian. He argues the gap between companies talking about AI and companies actually running on it comes down to ops, not technology. In this episode he explains why leaders are structurally cut off from on-ground reality, why a 5,000-person firm is still managing a hundred active projects out of email threads while million-dollar invoices get written by hand, and where the MIT Nanda study's 95% failure rate really comes from (hint: it's the people layer, not the software). He walks through the "chief agent officer" model, an AI chief of staff coordinating specialist agents across zoning, leasing, acquisitions, and legal. He covers the four pillars he uses to diagnose any business, and the pricing thesis behind what his team calls outcome as a service: you don't pay an accountant for software, you pay so you never think about your books again. Plus what happens to agencies and professional services firms when outcomes get cheaper, and the one thing Mo says humans have to keep owning completely.CHAPTERS00:35 – AI as the operating system, not another tool04:37 – What competing for Team Canada taught Mo about execution05:23 – Why leaders are always removed from on-ground reality07:26 – Million-dollar invoices, still written by hand08:33 – Being his own first customer09:49 – Why 95% of AI implementations fail10:45 – The command brief and the four pillars12:49 – The chief agent officer and the 80/20 rule14:57 – Outcome as a service: accountant vs. QuickBooks19:05 – Employee fear, and why agencies should be worried21:17 – What humans still have to own completely22:41 – Building your own harnessLINKSConnect with Mohammad Moahidzerotoagent.com • LinkedIn • InstagramStay Connected with Founder ModeSubscribe to our newsletterConnect with KevinLinkedIn • X/TwitterConnect with JasonLinkedIn • X/Twitter