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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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Kevin shares lessons from Pretty Good AI on how AI reveals broken workflows, exposes bottlenecks, and becomes a forcing function for alignment.
Featured Post

What Your AI Is Really Telling You About Your Business

AI As a Mirror Welcome back to Founder Mode! When teams talk about AI, they usually focus on one metric. How many calls did it answer? How many tickets did it resolve? How many hours did it save? But after building Pretty Good AI and deploying it inside real operations, I have learned something different. The real KPI is not what the AI handles. It is what it exposes. AI is not just automation. It is a mirror. And sometimes what it shows you is uncomfortable. We Thought It Was a Demand...

3 days ago • 3 min read
Lessons from CrackBerry Kevin on building intentional hardware, creating a new category, and launching products without fantasy math.

Bring Back BlackBerry with Kevin Michaluk Welcome back to Founder Mode! Most tech products today try to do everything. Your phone is your camera, your inbox, your calendar, your TV, your wallet, and your work tool. That sounds great. But it also creates a problem. When a device does everything, it is hard to focus on one thing. In this episode of Founder Mode, we talked with CrackBerry Kevin. He spent years building one of the biggest and most loyal tech communities in the world. Now he is...

8 days ago • 3 min read
Kevin shares lessons from Pretty Good AI on why AI fails in messy workflows and how alignment, clean data, and configuration drive success.

The Real Bottleneck Isn’t the AI Welcome back to Founder Mode! I keep hearing the same thing from teams rolling out AI. “The model isn’t performing the way we expected.” Most of the time, that’s not true. The bottleneck is not intelligence. It’s alignment. At Pretty Good AI, we have seen this pattern repeat across healthcare groups, service companies, and even tech-forward operators. Teams think implementation means turning on AI. In reality, implementation means cleaning up everything...

10 days ago • 3 min read
How AI and honest money talks can strengthen relationships. Founder Ronke Oyekunle modernizes prenups for today’s couples.

Founder Mode Episode 45 - Modernizing Prenups with Ronke Oyekunle Welcome back to Founder Mode! In this episode of Founder Mode, we talked about something most founders avoid. Prenups. Money. Marriage. Hard conversations. Ronke Oyekunle is building Neptune, a company that modernizes prenups using AI and human lawyers. At first glance, it sounds cold. Legal. Transactional. But the more we talked, the clearer it became. This is not about divorce. It is about alignment. The Conversation Most...

15 days ago • 2 min read

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...

17 days 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...

22 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...

24 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...

29 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...

about 1 month 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...

about 1 month ago • 2 min read