Introducing Founder Roadbook

My side project prototype for first-time startup founders and bootstrapped entrepreneurs, to accelerate the learning of unteachable lessons in entrepreneurship.

Europe needs more tech entrepreneurs who succeed in building sustainable and profitable companies.

Tech entrepreneurship is about placing bets and taking calculated risks. If you're good at this, you have good judgment.

Now could AI support entrepreneurs in making better bets and taking smarter risks?

This leads me to my hypothesis:

“AI can accelerate the learning of unteachable lessons in entrepreneurship by providing real-time feedback, simulations, and optimising milestones, thereby reducing operational debt and the risk of derailing the company.”

The result? → Faster progress + bigger chance toward sustainable revenue.

If this is true, AI should be able to:

✅ Understand the founder’s type and profile, so advice is hyper-personalised.
✅ Identify where the company is right now and anticipate the next steps ahead of time.
✅ Determine what is validated and assess the maturity of current efforts, is it good enough?

If AI can do this, it could guide, support, and co-pilot mentor entrepreneurs.

I call this approach: Milestone-Based Building & Evidence-Based Investment.

First concept: Founder Roadbook: Accelerate the learning of unteachable lessons in entrepreneurship

The Challenge 🤔

Founders tend to be stubborn. Many score high on disagreeableness and overconfidence. Personality traits that help them push through challenges but can also blind them to critical advice. The key is knowing when to be coachable, when to listen to AI-driven insights, and when to trust your own vision. More about different founder personality types and profiles here.

AI should enable just-in-time learning:
📌 The right information
📌 At the right time
📌 For the right founder profile type

But a tool alone won’t be enough. Cognitive biases may still lead entrepreneurs to place the wrong bets/bad judgement or become emotionally attached to ideas, making it hard to accept tough advice from AI.

That’s why I believe mentors and coaching are still necessary to test the model, methodology, and milestone-based approach. Secondly, it also helps with accountability support.

Different Founder Profiles & Types

Building Founder Roadbook

Founder Roadbook is my first prototype for first-time startup founders and bootstrapped entrepreneurs.

What is Founder Roadbook?

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Founder Roadbook helps first-time startup founders and bootstrapped entrepreneurs, reach sustainable revenue faster by accelerating the learning of unteachable lessons in entrepreneurship.

Founder Roadbook

For now, it's a side project built with Lovable, Supabase, Resend, and Notion. I'm still learning and it’s fun. Feedback is welcome. 🙏🏼

I want to open-core my methodology so the community can use and contribute to it. This should be open to all entrepreneurs and mentors/coaches.

Prototype

First drafts: with the 7 Development Tracks, the 4 stages, the 4 gates and the 37 milestones.

First drafts: with the 7 Development Tracks, the 4 stages, the 4 gates and the 37 milestones.

Roadbook filled out with 37 Milestones, Gates & Operational debt.

Example to create & download your own Founder Roadbook.

Example create and download your own Roadbook at www.founderroadbook.com

First Unteachable Lessons with self-assessment, practical reflection and scenarios.

Founder Roadbook: Unteachable Lessons

What’s Next? Call to Actions 😋

Founder Coaching: I’m testing the model, milestones, and methodology. If you're a first-time founder (Seed/Series A) or bootstrapping a company, reach out at Founder Roadbook for startup founder/leadership coaching.

Create & Download your own Founder Roadbook using 37 milestones: Get it here.

Explore the first Unteachable Lessons and do the self-assessment. Try it out here.

Learn about Founder Personality Profiles & Types: Read my blog.

Understand Operational Debt: Read my blog.

Follow my newsletter for updates on AI entrepreneurship, milestone-based building, and founder leadership development: Subscribe here

I would love to get feedback. Please provide ideas and features here.

Please reach out if you want to build together and tackle this problem and help more entrepreneurs to succeed. 

Prototype: www.founderroadbook.com 

Founder Roadbook