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...
7 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...
12 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...
14 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...
19 days 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....
21 days 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...
28 days ago • 5 min read
Founders’ Notebook: Emerging AI Insights That Actually Matter Welcome back to Founder Mode! It’s Christmas Eve, and this is the time of year when I naturally slow down and reflect. Not just on wins or numbers, but on what actually changed, what worked, and what didn’t. It’s a rare pause in the noise, and a good moment to think clearly about where things are heading, especially in AI and services. As we build Pretty Good AI and spend time with operators across industries, a few patterns keep...
about 1 month ago • 4 min read
Building a Smarter Dumb Phone: Why Simplicity Still Wins Welcome back to Founder Mode! We all know smartphones have become addictive. Notifications, endless scrolling, and constant distractions have taken over. But what if the answer isn’t no tech just less? In this episode of Founder Mode, Jason and I chatted with Austin Boer. He founded Sleke, which makes the “perfect dumb phone.” His team is creating a distraction-free phone. It offers the essentials like maps, calls, and texts, but keeps...
about 1 month ago • 3 min read
Founder Insights and Contrarian Takes Welcome back to Founder Mode! The more we develop Pretty Good AI (PGA for short), the more I see that most founders aren’t failing due to competition. They’re losing because they’re using the wrong playbook. Standard startup advice may seem wise, but it can lead you astray. The founders who win today are the ones who look at a messy problem and say, “I want that one.” They ignore the trends. They ignore the noise. They focus on what brings real leverage....
about 1 month ago • 4 min read