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

LINKS

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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

LINKS

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