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Founder Mode

by Kevin Henrikson

Founder Mode is a weekly newsletter for builders—whether it’s startups, systems, or personal growth. It’s about finding your flow, balancing health, wealth, and productivity, and tackling challenges with focus and curiosity. Each week, you’ll gain actionable insights and fresh perspectives to help you think like a founder and build what matters most.

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Featured Post

Why Your AI Is Breaking and How to Fix It

AI Doesn’t Fail. Your Process Does. Welcome back to Founder Mode! Over the past month, I have had the same conversation again and again. “The AI messed up.” Every time I hear that, I pause. Because in most cases, the AI did not mess up. It followed the rules exactly as they were written. The real problem was buried deeper. At Pretty Good AI, we have learned this the hard way. Most AI failures happen slowly. They are not dramatic crashes. They show up as wrong bookings, strange routing...

about 7 hours ago • 4 min read
Jason Fried shares why keeping surface area small, working 40 hours, and staying independent leads to better products and lasting companies.

When Enough is Enough with Jason Fried Welcome back to Founder Mode! In this episode of Founder Mode, we sat down with Jason Fried, co-founder of 37signals, the makers of Basecamp, HEY, and now Fizzy. Jason has been building software for over two decades. He has strong opinions about design, work, independence, and how companies should operate. This conversation was not about growth hacks. It was about restraint. Here is what stood out to me. Software Should Feel Like Something You Can Touch...

5 days ago • 2 min read
Kevin shares lessons from Pretty Good AI on audit-driven sales, reliable automation, voice trust, and why depth beats width in enterprise AI.

AI, Agency, and Audit-Led Sales Welcome back to Founder Mode! There is a strange pattern I keep seeing as we build Pretty Good AI. The things people say they want are often not what they actually respond to. We assume customers want more human touch. We assume business owners want big platform pitches. We assume the fastest way to grow is to sign more logos. But when you step into the real world and look at behavior instead of opinions, the truth is different. Reliability beats charm. Depth...

7 days ago • 3 min read
Stephanie Joyce shares how to scale multi-location service businesses by prioritizing people, building systems, and navigating crisis with clarity.

Scaling Multi-Location Businesses with Stephanie Joyce Welcome back to Founder Mode! In this episode of Founder Mode, we sat down with Stephanie Joyce, a medspa founder and multi-location operator who’s led through turnarounds, acquisitions, and rapid growth. If you're scaling a service business, or even thinking about adding a second location, this one is packed with playbooks. Stephanie's operated in high-pressure environments where getting it wrong meant losing customers, team trust, or...

12 days ago • 2 min read
Kevin shares lessons from Pretty Good AI on how to sell AI by lowering friction, leading with small utilities, and targeting the real pain holders.

The Trojan Horse Playbook for Selling AI in the Real World Welcome back to Founder Mode As we build Pretty Good AI, I see that most enterprise deals fail. It’s not because the technology isn’t good enough. They fail because we ask for too much trust, too early. Founders love pitching the big vision. The platform. The transformation. The future state. But most buyers are buried in today’s problems. They don’t have time to imagine a new world. They just want one annoying thing to go away. This...

14 days ago • 3 min read
From the OR to mental health: Dr. Jay Motley shares how ketamine, lifestyle medicine, and AI are reshaping care. Here's what founders should know.

Founder Mode Episode 42 - From Doctor to Founder with Jay Motley Welcome back to Founder Mode! In this episode, we sat down with Dr. Jay Motley. He is a former anesthesiologist who left the operating room to build a new kind of mental health clinic. We talked about lifestyle medicine, ketamine therapy, and what it’s like to leave a 10+ year career in medicine to become a founder. It was one of the most honest and inspiring conversations we’ve had. Let’s get into it. 1. Time Is the Scarce...

19 days ago • 2 min read
Startup advice that actually works. From healthcare to racing, founders share raw insights about risk, pressure, and what to do when things get messy.

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...

26 days ago • 2 min read
Kevin shares hard-earned lessons from building Pretty Good AI on AI operations, onboarding, distribution, and protecting real intellectual property.

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...

28 days ago • 3 min read
Driving a formula car is like running a startup. Here’s what I learned about control, momentum, and focus after racing at Laguna Seca.

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...

about 1 month ago • 2 min read
Kevin shares contrarian lessons from building Pretty Good AI on monetization, trust-first contracts, AI onboarding, and turning data into a utility.

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...

about 1 month ago • 4 min read