Best of Founder Mode II Welcome back to Founder Mode! After 40 episodes of Founder Mode, one thing’s clear:The same problems show up everywhere. Different founders, industries, and ideas, but the same core pressure. You’re making decisions with limited time, incomplete data, and real consequences. The insights that help most? Not more frameworks.It’s hearing how other builders actually think when it gets messy. So we cut together the rawest moments, the points where founders stopped posturing...
11 days ago • 2 min read
Founder Insights and Lessons Welcome back to Founder Mode! I’ve been thinking a lot about what actually moves the needle when building an AI company. And here’s the thing: it’s rarely the stuff that sounds impressive. The breakthroughs at Pretty Good AI didn’t come from better models or cleverer prompts. They came from fixing the boring parts. The parts that quietly slow everything down while everyone’s distracted by the shiny stuff. This week, I want to share a few lessons straight from the...
13 days ago • 3 min read
Founder Mode Episode 40 - Move Fast & Brake Things with Allen Berg Welcome back to Founder Mode! This week, we took Founder Mode out of the studio and onto the track. We joined Allen Berg at the legendary Laguna Seca to drive real open-wheel formula cars. Full-speed laps, stick shifts, no power steering, and no room for error. Honestly? It felt a lot like running a startup. Here’s what we learned, and why racing is the perfect metaphor for building companies. “It’s like all gas, little...
18 days ago • 2 min read
Founder Insights and Contrarian Takes Welcome back to Founder Mode! The longer I work on building an AI company, the more I realize that most of the best strategies don’t sound impressive at first. They don’t show up well on slides. They don’t fit neatly into the usual startup playbook. What actually works often feels backward. It’s about removing friction, giving up control where others try to lock it down, and doing the hard, boring work so customers don’t have to. Lately, a few ideas keep...
20 days ago • 4 min read
Uh-Oh Everything's Broken with Jonathan Sturgeon Welcome back to Founder Mode! I spend a lot of time thinking about systems. Sales systems. Product systems. Support systems. And today I want to share something we don’t hear enough: You don’t need to be an influencer to win. In this week’s episode of Founder Mode, we talked to Jonathan Sturgeon. He runs two real businesses (a creative agency and an IT company) with no personal brand, no daily posting habit, and no growth hacks. His model is...
25 days ago • 2 min read
Why We’re Betting on “Pretty Good” Instead of Perfect Welcome back to Founder Mode << NEW SITE I’ve been building companies in the Valley for a long time. Long enough to see hype cycles come and go. Right now, the loudest one is Artificial General Intelligence. Everyone is racing to replace humans entirely. But when you enter the real world, especially in healthcare, that vision crumbles quickly. At Pretty Good AI, we don’t spend our time chasing perfect systems. We answer phones, fix...
27 days ago • 4 min read
Founder Mode Episode 38 - From Flight Deck to Front Line with Max Trescott Welcome back to Founder Mode! In this episode, we recorded from the sky. Literally. Jason and I took a Vision Jet to Monterey. We brought aviation legend Max Trescott with us. Max has over 12,000 flight hours. He shared what flying teaches about leadership, stress, structure, and focus. Turns out, the cockpit has a lot to say about building startups. Let’s get into it. Startup Life Needs Checklists Pilots don’t wing...
about 1 month ago • 2 min read
Where Growth Breaks: Lessons From Building AI in the Real World Welcome back to Founder Mode! Lately, I’ve been thinking a lot about where growth actually breaks. Not on the charts. Not in pitch decks. But inside the system itself. At Pretty Good AI, we spend our days building AI for real businesses. Not just demos. Not hype. Real operations with real customers have real consequences if things go wrong. The deeper we dive, the clearer it gets: the biggest chances in AI are also the toughest....
about 1 month ago • 4 min read
Most of Building a Company Is Just Fixing the Plumbing Welcome back to Founder Mode and Happy New Year, everyone! As I look back this year at Pretty Good AI, the biggest lesson is not about strategy or big wins. It is about the small things that quietly make or break momentum. Most progress did not come from breakthroughs. It came from fixing what was already there. Cleaner systems. Better data. Clear ownership. Fewer handoffs that break under pressure. This year reinforced something I keep...
about 1 month ago • 5 min read