How to Use AI to Create Your Own Personal Board of Directors
(Even If You’re a Team of One)
Starting a business, or making any big career move, can feel like being the CEO of a company with no exec team, no investors, no advisors, and no map.
But what if you could build your own personal board of directors?
Made up of legendary thinkers, founders, operators, and creators — even if they’ve never met you?
Thanks to AI, you actually can.
And in this article, I’m going to show you how to assemble your own dream advisory board using publicly available content + AI tools to simulate their thinking, guide your decisions, and help you avoid costly mistakes.
Why Build a Personal Board of Directors?
You don’t need more opinions. You need better frameworks.
Your board isn’t about giving you the answers — it’s about helping you ask sharper questions and see your blind spots.
Think of this as building a diverse panel of virtual mentors who each offer unique perspectives on:
Product and pricing decisions
Brand strategy and positioning
Market entry and timing
Hiring and team dynamics
Fundraising vs. bootstrapping
Personal mindset and leadership
Step 1: Choose Your Board. Curate 5–7 Strategic Personas.
Here’s a sample board structure you can borrow or remix:
1. The Visionary Operator – Elena Verna
👉 Known for growth loops, GTM strategy, and operating with clarity.
2. The Practical Creator – Steph Smith
👉 Known for building indie projects with distribution in mind from day one.
3. The Emotional CEO Whisperer – Claire Hughes Johnson
👉 Former COO at Stripe, excellent at org design, decision-making, and scaling teams.
4. The Hype-Free VC/Angel – Elizabeth Yin
👉 Cofounder of Hustle Fund. Candid, tactical, anti-fluff investor.
5. The Content-First Founder – Justin Welsh
👉 Champion of one-person businesses, distribution-first mindset.
6. The Systems Thinker – Lenny Rachitsky
👉 PM turned writer with frameworks for scaling, product-market fit, and growth.
7. Wildcard/Mentor-You-Wish-You-Had – Think Scott Galloway for tough love or Brené Brown for leadership courage.
You can always swap in your own faves — whether it’s Naval, Chamath, Sophia Amoruso, Arlan Hamilton, or a mix of niche creators from LinkedIn or YouTube.
Step 2: Collect Their Content. This Is Your Data Source.
You’ll need a decent “training set” to simulate their thinking.
Blog posts
YouTube interviews or podcasts (transcripts work too)
LinkedIn thought pieces
Twitter threads
Books or essays
Course content, if accessible
Tip: Use tools like Glasp or Readwise Reader to clip and tag your favorite insights.
Step 3: Upload to NotebookLM or ChatGPT with Custom Instructions
NotebookLM – Upload docs or transcripts. The AI will synthesize and summarize the person’s key ideas. Great for comparing across your board.
ChatGPT (Custom GPT or GPT-4 with memory) – Use system prompts like:
“You are Justin Welsh, a solopreneur and content creator. Based on your past content, respond to questions as Justin would — focusing on distribution, leverage, and one-person businesses.”
Repeat this for each “board member.”
Step 4: Ask Your Board Questions
Whenever you’re facing a tough decision, run your idea through your “board.”
Here’s an example:
Scenario: You’re deciding whether to turn your coaching offer into a productized service.
Ask your virtual board:
What would Steph Smith say about this from a content leverage perspective?
How would Claire Hughes Johnson advise me on operational complexity?
What’s Elizabeth Yin’s take on this model from a scalability or fundraising lens?
What would Lenny Rachitsky want to see in terms of early traction?
Let AI respond using each persona’s lens. You’ll be surprised by how clear things become when you “hear” it from multiple perspectives.
Bonus: Use Voice AI to Talk It Out
Tools like HeyPi or Replika let you simulate conversations. Set up a “Pi” with your persona’s vibe and talk to them out loud.
Or record a Loom and use AI transcription tools (like Descript) to pull out insights and match patterns.
Why This Works
You’re not just getting random advice.
You’re creating a decision-making filter based on values, proven experience, and mental models.
It’s not about idolizing these people.
It’s about borrowing their lenses.
TL;DR: How to Build Your AI-Powered Board
1. Pick 5–7 mentors you admire with publicly available content
2. Collect their writing, talks, or interviews and feed it to an AI tool
3. Create custom GPTs or NotebookLM files to simulate their guidance
4. Ask them questions when you’re stuck or deciding something big
5. Let their frameworks sharpen yours
Final Thoughts
You’re not alone, even if it feels like it sometimes.
The smartest founders and operators don’t make decisions in a vacuum. They surround themselves with people who think differently, challenge assumptions, and elevate strategy.
Thanks to AI, you can do the same.
So build your personal board.
And don’t just ask, “What should I do?”
Ask, “How would they think about this?”
You’ve got more wisdom in your orbit than you think.
Let’s use it.