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

Connect with Keith Wasserman

Gelt Venture Partners • LinkedIn • X/Twitter

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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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Connect with Kevin

LinkedIn • X/Twitter

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LinkedIn • X/Twitter

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

Connect with Claire Stapleton

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

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Connect with Kevin

LinkedIn • X/Twitter

Connect with Jason

LinkedIn • X/Twitter