AI Moats, Money, and Month to Month Trust Welcome back to Founder Mode! I have been spending a lot of time thinking about what actually creates a durable business in AI. Not a cool demo. Not a weekend GPT wrapper. A real business. One that customers trust, rely on, and pay for because the outcomes are too valuable to replace. Inside Pretty Good AI, we feel this shift every day. The market is crowded at the surface level. Everyone can build something neat. Everyone can stitch together prompts...
3 days ago • 4 min read
How I Learned to Win Founder Negotiations Using Pricing and Leverage Welcome back to Founder Mode! Happy Thanksgiving! Before we begin, I would like to express my gratitude. Thanks for reading. Thanks for building. And thanks for being part of this journey. Let’s get into it! How Founders Win Negotiations: Pricing, Leverage, and Value Most founders spend a ton of time building the product and almost no time thinking about how to price it. That used to be me, too. With Pretty Good AI, we’ve...
9 days ago • 3 min read
Founder Mode Episode 34 - When Founders Show Up Welcome back to Founder Mode! In this episode of Founder Mode, Jason and I explored a topic that many startup builders miss: events. Should founders stay heads-down and build? Or show up, sponsor booths, and pitch live? We just got back from a big healthcare AI conference in Nashville, and we learned a lot. Our team went all-in, and it changed how I think about events forever. “Founder mode events mean this: Don’t just attend—activate.” — Kevin...
15 days ago • 1 min read
The Firehose Effect: What I Learned About Learning, Listening, and Leading in the Early Days Hey, Welcome back to Founder Mode! I want to share something with you today. It's about those early days when everything feels like chaos. You know the feeling. You join a startup or start something new, and it's like drinking from a firehose. Information comes at you from every direction. You're supposed to know everything yesterday. I've been there. And I've made every mistake in the book. But...
17 days ago • 10 min read
The Healthcare AI Wedge: Go Narrow to Win Big Welcome back to Founder Mode! I've watched dozens of AI startups try to break into healthcare. Most of them fail. Not because their technology is bad. They fail because they try to do too much at once. Let me tell you what actually works. Start Small, Win Big To sell AI to hospitals and healthcare companies, I learned you need a way in. Think of a wedge like the thin edge of a door stopper. You don't kick the door down. You slide something small...
22 days ago • 8 min read
Electrifying Aviation with Kevin Noertker Welcome back to Founder Mode! In this episode, we traveled to Long Beach Airport. There, we chatted with Kevin Noertker, the co-founder and CEO of Ampaire. Kevin is building a new type of airplane: a hybrid-electric model. This could change the aviation industry. Ampaire upgrades current aircraft with hybrid-electric engines. They want to improve the systems they have instead of building new planes. It’s faster, safer, and uses less fuel. The goal? A...
23 days ago • 1 min read
Will AI Replace Developers with Natalie Kaminski Welcome back to Founder Mode! In this episode, we chatted with Natalie Kaminski. She is the founder and CEO of JetRockets. She teams up with technical and non-technical groups. They work together to build secure, real software. We explored AI's impact on building. We talked about what it can do today. We also asked if software engineers should worry about being replaced. Natalie shared her view: AI is helpful, but it can't replace human skills....
30 days ago • 1 min read
The Systems, Speed, and Strategy Behind Great Founders Hey there, Welcome back to Founder Mode! I’ve thought a lot about what makes good founders different from great ones. It's not just about those who gather funds or attract press. It’s also about the people who create real changes in how we work and live. Before we continue, I’ll share what we learned at our Founder Mode Live event in San Francisco Tech Week. We talked to Max Mullen at Instacart and Andrew Ofstad at Airtable. Both have...
30 days ago • 9 min read
The Halloween Horror Story Every Founder Needs to Hear Welcome back to Founder Mode! It’s Halloween season! Some people think about costumes and candy. I want to bring up a topic that’s really unsettling: founder mistakes. Not the kind for LinkedIn posts or fancy case studies. These are the quiet ones that lurk in the shadows until they strike. The kind that empty your wallet, slow you down, and make you question what went wrong. Every founder fears competition, but that’s not the real...
about 1 month ago • 3 min read