EPISODE 81

Kevin 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.

CHAPTERS

00:00 – Welcome to the fourth Founder Mode best-of

00:49 – Anthony Ng Monica: when your body makes the call

02:32 – The AI stack nobody at the conference could name

03:32 – 76 agents and the one that failed silently

04:37 – Seek Sahib: the night he almost shut it all down

05:46 – Joe Speiser: the $100M cost of building on rented land

07:14 – "Do the right thing": letting Claude handle the inbox

09:07 – Optionality, default alive, and a 93 sleep score

10:17 – Jess Chan: the hard choice to grow slower

11:27 – Alex Finn and Viktor debate giving AI their email

12:49 – Jason Cohen: why customers don't cancel over price

14:18 – AI agents don't get weekends

15:39 – JJ's pitching machine rule for getting better at AI

16:48 – Mohammad Moahid: accountability stays with humans

17:41 – Will the AI labs eat your business?

19:08 – The AI outbound campaign that made $0

21:20 – Kiko Zang and the mascot suit

22:50 – Zimbra's free playbook and why it matters again

24:31 – JJ Zhuang: where the AI and human line goes next

26:15 – Claire Stapleton: YouTube and the ads machine

27:41 – Keith Wasserman calls all 1,800 investors

29:16 – Hand off the work, keep the judgment

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EPISODE 80

Keith 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.

CHAPTERS

00:00 – Why Fear Is the Best Time to Buy

00:36 – Investing Through Uncertainty

02:39 – Meet Keith Wasserman

03:16 – The $140K Fourplex That Started It All

04:51 – Scaling From Four Units to Hundreds

05:58 – Fixed-Rate Debt and Protecting the Downside

07:15 – Get Rich Slow: Why the Wealthy Never Sell

10:21 – Why This Cycle Is Harder Than 2009

11:50 – What Investors Misunderstand About Today's Market

12:49 – Real Estate vs. the S&P 500

15:52 – Calling 1,800 Investors One-on-One

19:50 – Building a Team Around Your Blind Spots

21:59 – Gelt's First Fund and the Austin Opportunity

24:24 – Founder Mode Top 5 Takeaways

LINKS

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EPISODE 79

In 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.

CHAPTERS

00:00 – Cold Open

00:43 – Jason's First Marathon and the AI Agent That Ordered His Carbs

04:42 – 2026: The Year AI Agents Hacked Real Companies

06:18 – How Worried Should We Be?

07:35 – Inside the Incidents: RubyGems, Gemini, Medicare and More

12:09 – 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 Heist

23:52 – Has a Robot Run a Marathon Yet?

24:50 – Founder Mode Top Five

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EPISODE 78

Claire 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."

CHAPTERS

00:00 – Cold open

00:41 – Is culture load-bearing or just marketing?

04:07 – Selling meaning as a perk

05:42 – Ghostwriting Larry Page and the cure-death era

08:35 – Google+ and the corporate bonus

10:29 – When the story cracked: Creative Lab

13:18 – YouTube and the brand vulnerability briefing

15:54 – Was advertising the real mission all along?

18:10 – Marketing to executives instead of the public

21:31 – Maven, the walkout, and why workers went quiet

25:21 – Would she organize the walkout again?

28:08 – The subway ride home

32:06 – Where to find Claire and Don't Be Evil

33:13 – The Founder Mode Five

LINKS

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Don't Be Evil • Tech Support • LinkedIn • X/Twitter • Instagram

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EPISODE 76

JJ 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.

CHAPTERS

00:00 – Cold Open: Why Not Just Solve All Your Problems?

00:31 – JJ Returns: Grading 10 Predictions One Year Later

01:58 – Generalists vs. Specialists: Who Should You Hire?

04:39 – Is AI Really Writing Half of All Code?

07:28 – Taste, Comprehension, and the Human Edge

09:58 – Instant Prototypes, Fast Software, and the Death of Slide Decks

12:39 – Directing AI and the Most Overhyped Buzzword

14:32 – Overhyped or Underestimated? The Opus 4.6 Moment

17:09 – The Scorecard: 6.5 for 10

18:00 – Pretty Good AI's Big Bet: Solve Every Problem

20:02 – What Success Looks Like: Becoming Your Customers' AI Team

20:39 – Designing Around AI That's Confidently Wrong

22:20 – Where the Line Between AI and Humans Moves Next

24:09 – Building on Models That Change Every Few Months

25:58 – Compliance When Your Team Is Agents

28:23 – What Patients Notice First

30:17 – How a Lean Team Wins a Crowded Market

LINKS

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EPISODE 75

Kevin 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.

CHAPTERS

00:00 – The Slack message Claude sent by itself

00:39 – A dozen AI tools in a single day

03:46 – $800 a month for a CRM

04:26 – Dharmesh's $1 CRM and the SaaSpocalypse

08:03 – Freemium after vibe coding: the Zimbra lesson

10:32 – Building an agentic agency

13:20 – Succession: hand off jobs, not titles

16:33 – What AI still can't do in marketing

19:18 – Biological age scores and walled-garden health data

22:22 – Founder Mode top five

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EPISODE 74

Kiko 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.

CHAPTERS

00:00 – More herself inside the suit

00:40 – Know your audience or know yourself

04:07 – Half a life spent pretending

06:14 – The PTA rehearsal that got her sent abroad

08:34 – The reluctant founder

11:44 – The fursuit and who gets assumed to be the founder

14:05 – Anonymity, honesty, and shared reality

16:12 – Playing Chomp live

19:24 – 93% green flag and the perception gap

22:20 – Pluralistic ignorance and why consumer has no moat

24:31 – Honest opinion as the data of the AI era

27:50 – The co-founder breakup and fears that aren't real

30:06 – Where to find Chomp

LINKS

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