Get Rich Slow with Keith Wasserman Welcome back to Founder Mode! My guest this episode is Keith Wasserman, co-founder of Gelt, a real estate investment firm that's completed billions of dollars in transactions over the past 20 years. He and his cousin Damien bought their first deal in 2008, a fourplex for $140,000, mostly out of a mix of ignorance and not wanting to work for anyone else. Twelve months and eleven or twelve fourplexes later, they'd learned the renovate-and-lease playbook well...
about 2 hours ago • 3 min read
The Zoo Animals Are Out Welcome back to Founder Mode! It's another solo one, just Jason and me, fresh off Jason finishing his first marathon the day before we recorded (he hit his "don't get hurt" and "finish it" goals, missed "under four hours," and an AI nutrition coach ordering his DoorDash mid-training deserves its own episode someday). But the real topic this week is a lot less fun and a lot more real than it was a year ago. In 2025, AI misbehavior was mostly staged lab experiments:...
17 days ago • 4 min read
Google's Storyteller Walked Out with Claire Stapleton Welcome back to Founder Mode! Jason and I sat down with Claire, who spent twelve years inside Google and YouTube, first ghostwriting for Larry Page, then working in Google's Creative Lab before moving into marketing and social media at YouTube. In 2018, she co-organized the Google walkout, 20,000 employees who walked out over how the company handled sexual harassment allegations. She left in 2019, and this year published her memoir, "Don't...
24 days ago • 1 min read
[Headline] Welcome back to Founder Mode! This episode brings back two repeat guests, Viktor Petersson of Sbomify and Screenly, and Alex Finn of Henry Intelligent Machines, who sit on almost opposite ends of the same question: how much should you actually trust your AI agents? 🎧 Listen to Founder Mode Episode 77 here: Cage or Release Your Agents?... Oct 8 · Founder Mode 40:48 Viktor runs every one of his agents through a web proxy that gives it just enough access to do its job and nothing...
about 1 month ago • 3 min read
Was Yoda Right About AI? with JJ Zhuang (Plus Pretty Good AI Episode: Pretty Good AI, One Year In) Welcome back to Founder Mode! I have two shows for you this week, and both feature my co-founder JJ Zhuang, so this is a bit of a special one. First, check out the newest episode of Founder Mode. Then stick around for episode six of the Pretty Good AI Podcast. 🎧 Listen to Founder Mode Episode 76 here: Was Yoda Right About AI? wit... Oct 1 · Founder Mode 33:21 JJ is one of our first repeat guests...
about 1 month ago • 3 min read
The $1 CRM Killer Welcome back to Founder Mode! On the latest Founder Mode episode, it's just Jason Shafton and me again, catching up on everything AI-related that happened to us this past week. Jason kicks it off with a story about asking an AI agent to draft a Slack message for a client, only to have it send the message instead, tagged "sent from Claude" at the bottom. When he pointed out the mistake, the agent offered to file a bug report against itself. We got into why the wording you...
about 2 months ago • 3 min read
The Fursuit of Happiness with Kiko Zang On the latest Founder Mode episode, Jason Shafton and I talk with Kiko, founder of Chomp, about something most founders don't say out loud: how much of building a company is really about figuring out who you actually are. Kiko grew up moving between China, New Zealand, and the US, and spent years adapting her personality to fit whatever room she was in. She built her first crypto company, Orca, while staying anonymous for a year and a half. Later, she...
about 2 months ago • 2 min read
The Accountant vs. QuickBooks Test with Mohammad Moahid On the latest Founder Mode episode, Jason Shafton and I talk with Mohammad Moahid, an operator who's turning AI agents into an actual part of how a business runs, not just another tool bolted on the side. 🎧 Listen to Founder Mode Episode 73 here: The Accountant vs. QuickBook... Sep 10 · Founder Mode 26:21 Mo built his first AI system to solve his own problem: an influencer-seeding tool for his e-commerce company. From there, he took the...
about 2 months ago • 3 min read
13 Agents Watching 76 Agents I have two shows for you this week. First, check out the newest episode of Founder Mode. Then stick around for episode two of the Pretty Good AI Podcast. 🎧 Listen to Founder Mode Episode 72 here: 13 Agents Watching 76 Agents Sep 3 · Founder Mode 28:27 On the latest Founder Mode episode, Jason Shafton and I get into how we price our services, what happens when AI quietly breaks instead of loudly failing, and why some of the biggest deals in healthcare tech are...
2 months ago • 3 min read