The Myth of the Flat Organization Welcome back to Founder Mode! I don’t care about your title, and neither should the person sitting next to you. That’s something I’ve come to believe more and more while building Pretty Good AI. We’re a small team. We’re moving fast. We’re building in a space that changes every week. And the fastest way to slow all of that down is to start worrying about who reports to whom. I’ve seen this pattern repeat. The moment people start asking about structure, things...
7 days ago • 4 min read
Founder Mode Episode 52 - Grab A Shovel Welcome back to Founder Mode! In this episode, it was just Jason and me. No guest. No script. We talked about something we’re both dealing with right now. AI is getting more powerful, but it’s also getting weirder. Sometimes it helps a lot. Sometimes it confidently does the wrong thing. And the tricky part is that the mistakes feel worse than human mistakes. Let’s get into it. 1. AI Mistakes Feel Worse Than Human Mistakes When a person messes something...
13 days ago • 3 min read
Customers Don’t Know Their Own Process Welcome back to Founder Mode! There is a question we ask every customer at Pretty Good AI. “How does this work today?” And almost every time, we get a clean answer. Clear steps. Logical flow. Everything sounds organized. Then we turn the system on. And within a few days, that clean story falls apart. The Story vs The System When people explain their workflow, they describe the ideal version. It is how things should work.It is how they believe things...
14 days ago • 3 min read
Turning Audiences Into Businesses with Courtney Spritzer Welcome back to Founder Mode! In this episode, we sat down with Courtney Spritzer. She is the co-founder of Entreprenista, a platform built to help women entrepreneurs grow through real connection, support, and visibility. We talked about the difference between an audience and a real community, how to turn attention into a business, and why in-person connection still matters so much. This one was a practical conversation about what it...
20 days ago • 4 min read
The Funnel Wins, Not the AI Welcome back to Founder Mode! There is a moment that happens in almost every AI deployment we do. The team gathers around the AI call. They listen to it. They analyze it. They debate whether it sounded natural. Whether it asked the right questions. Whether it could be improved. And I get it. The AI call is visible. It feels like the product. But more often than not, the real problem has nothing to do with the call itself. At Pretty Good AI, we have learned this...
21 days ago • 3 min read
When AI Agents Go Rogue Welcome back to Founder Mode! In this episode, Jason and I did something a little different. No guest. No big prep doc. Just two founders talking through what we are seeing right now with AI agents, chief of staff tools, and the shift from chatbots to systems that actually go do work. We talked about why AI feels more broken when it takes action, why the right mental model is a junior employee and not magic software, and why communication may matter more than ever....
27 days ago • 4 min read
Rules Nobody Questions Welcome back to Founder Mode. There is something I have started to notice more and more as we build Pretty Good AI. Most businesses run on rules that nobody questions. Not because they are right. But because they have been there for a long time. They live in conversations, habits, and assumptions. They get passed down from one person to another. Over time, they harden into policy. Then AI shows up. And suddenly, those rules have to be written down. That is when things...
28 days ago • 3 min read
The Future of AI-Built Software with Nima Keivan Welcome back to Founder Mode! In this episode, we sat down with Nima Keivan. He has built autonomous systems in both robotics and software, and now he is focused on one of the hardest problems in AI-built software: reliability. We talked about autonomous coding, why code generation is no longer the main bottleneck, and what it takes to move from a demo to real production software. This one was a strong reminder that writing code is only a small...
about 1 month ago • 3 min read
The Sunk Cost Trap Welcome back to Founder Mode! There is a pattern I keep seeing that has nothing to do with AI models or technology. It has everything to do with people. Teams hold onto broken systems long after they stop working. Not because they believe in them. But because they already paid for them. At Pretty Good AI, we run into this all the time. The hardest part of implementation is not building something new. It is helping people let go of what is not working. And that is a much...
about 1 month ago • 3 min read