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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 how Pretty Good AI reveals hidden workflow assumptions, exposes broken rules, and forces teams to align processes for real AI success.
Featured Post

The Rules Your Team Follows That No One Wrote Down

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...

about 16 hours ago • 3 min read
AI can write code fast, but durable software still depends on context, requirements, and real production reliability.

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...

6 days ago • 3 min read
Kevin shares lessons from Pretty Good AI on why teams stick with broken systems, how sunk cost bias slows growth, and when to walk away to win faster.

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...

8 days ago • 3 min read
AI agents are changing how companies operate. Learn why founders must shift from building to system design and orchestration.

The End of Prompt Engineering with Dennis Pilarinos Welcome back to Founder Mode! We’re in the middle of a shift. Not a small one. Not another tool. Not another framework. A real shift in how companies get built. As I said in this episode: “It used to be build the product, hire the team, scale the ops. Now it's design the system, orchestrate the agents, and make the calls that can't be automated.” That’s the job now. And if you don’t see it yet, you will soon. AI Isn’t a Tool Anymore. It’s a...

13 days ago • 3 min read
Automation without measurement creates broken expectations. Learn why visibility must come first and how to fix your workflows before scaling.

Automation Without Visibility Is Dangerous Welcome back to Founder Mode! I keep seeing the same mistake. A team finds a task they hate doing by hand. It is slow. It is repetitive. It feels like the perfect place to automate. So they set up the workflow. They turn on the texts. They schedule the follow-ups. They build the sequence. Everyone feels productive. Then the system breaks trust. Not because the automation failed. Because the team automated something they did not understand. That is...

14 days ago • 6 min read
AI agents are changing the founder job. Here is how I think about systems, judgment, hiring, and what should still stay human.

AI Agents Are the New Employees Welcome back to Founder Mode! For a long time, the founder's job was pretty clear. You built the product. You hired the team. You scaled the operation. That is still part of the job. But it is no longer the whole job. What is changing now is the layer above all of that. Founders are starting to manage AI agents the way they once managed software tools, contractors, and teams. That means less manual work and more judgment. Less clicking and more deciding. Doing...

17 days ago • 4 min read
Kevin shares lessons from Pretty Good AI on how AI reveals broken workflows, exposes bottlenecks, and becomes a forcing function for alignment.

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...

22 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...

27 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...

29 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...

about 1 month ago • 2 min read