Have you ever wished you could just sit down with a legend and run your crazy startup idea past them? Most of us will never get five minutes with a top-tier venture capitalist, let alone eight straight hours. But one founder just did — kind of.
She didn’t fly to Sand Hill Road. She opened her laptop at 30,000 feet and started typing.
The Day a Founder Turned ChatGPT into Her Personal Board of Directors
Joanna Strober runs a fast-growing virtual care clinic focused on women’s midlife health. The company is already pulling in a $150 million annual revenue run rate, counts celebrities among its investors, and employs hundreds of specialized clinicians. By any normal standard, she’s crushing it.
Still, when it came time to lock in the next phase of aggressive growth, she felt the familiar itch every founder knows: Am I thinking big enough? Are my goals actually ambitious or just safely aggressive?
Normally you’d book coffee with mentors, beg for warm intros, or hope a VC returns your email. Joanna took a different route. She asked AI to channel two of the sharpest minds she admired — one living legend and one friend she recently lost.
Eight Hours with a (Very Convincing) John Doerr
John Doerr basically wrote the modern playbook on goal-setting with his book Measure What Matters. Google, Bono, the Gates Foundation — pretty much everyone who scales big uses his Objectives and Key Results (OKR) framework.
Joanna had never met the man. But decades of his podcasts, interviews, keynote videos, and that book gave the language model more than enough material to work with.
“I told it to be the ‘nice John Doerr’ first,” she laughed. “Then I switched and asked for the ‘harsh John Doerr.’ The tone changed completely — and the feedback got a lot sharper.”
She spent the entire flight iterating. Draft OKRs → paste → get feedback → argue back → refine → repeat. By the time the plane touched down, the goals felt battle-tested by one of the toughest investors on the planet.
Honestly? I’ve tried the same trick with other famous investors. Most of the time the answers feel generic. Something about Doerr’s public content must be unusually rich because founders who’ve tried this specific prompt keep saying the output is scarily accurate.
When AI Brought Back a Lost Friend
Mid-flight, Joanna was texting her husband about the Doerr session. He casually suggested something that turned a productive afternoon into an emotional one.
“Why don’t you run the same plan past Susan?”
Susan Wojcicki — former YouTube CEO, early Google employee, and Joanna’s close childhood friend — passed away from cancer in 2024. The loss was still raw.
Her husband opened a new chat and fed it public interviews, earnings calls, blog posts, everything Susan had ever said about management, growth, and culture. Then he pasted Joanna’s new OKRs.
“Her advice was so good,” Joanna said, voice catching. “I was sitting on the plane getting emotional because it really felt like Susan was proud but still pushing me to think bigger — exactly how she always was in real life.”
Look, I’m pretty cynical about AI sentimentality. But reading that account gave me chills. There’s something profound about being able to “talk” to someone you’ve lost, especially when their professional superpower.
Why This Actually Works (and When It Doesn’t)
Not every famous person makes a good AI mentor. The magic happens when three things line up:
- They’ve shared an enormous amount of specific, tactical content over decades
- That content is public and indexed
- Their thinking framework is consistent and repeatable (like OKRs)
Doerr and Wojcicki both check every box. Try the same with someone who only does vague keynote quotes and you’ll get motivational posters, not strategy.
In my own experiments, Bill Gates and Andy Grove (ex-Intel CEO) also produce shockingly useful output. Steve Jobs? Mostly theatrics. Warren Buffett gives conservative answers that sound nothing like his letters once you know them well.
The Bigger Trend: Democratized Mentorship
Here’s what excites me most. For the first time in history, the best thinking from the top 0.01% is becoming accessible to anyone with Wi-Fi.
Women founders, founders in emerging markets, first-time founders who don’t summer in the Hamptons — they rarely get real shots at world-class mentorship. Cold emails go unanswered. Accelerator “mentor hours” are often junior partners reading from scripts.
Now? You can pressure-test your deck against an AI-trained Paul Graham or Reid Hoffman at 2 a.m. while your baby finally sleeps. The gap between the connected and the unconnected just shrank dramatically.
The Emotional Layer Nobody Talks About
Most coverage of AI mentors focuses on productivity. But Joanna’s story reveals something deeper.
Founding a company is lonely in ways civilians never understand. When someone you admire — or loved — tells you (even through pixels) that your plan is solid, it hits different.
Grief, imposter syndrome, the constant fear you’re about to drive the ship into an iceberg — AI won’t fix any of that. But having a simulated “attagirl” from someone who earned your respect the hard way? That can be the difference between pushing through another quarter or folding.
How Any Founder Can Try This Today
Want to build your own AI board of AI advisors? Here’s the dead-simple recipe that’s working right now:
- Pick 3–5 people whose thinking you admire and who have decades of public content
- Open a new chat for each (keeps the context clean)
- Start with a detailed system prompt: “You are [Name]. You helped scale [Company]. You wrote [Book]. You are known for [Specific Framework]. Respond exactly in your style, be direct, push back when needed.”
- Paste your actual deck, OKRs, pricing strategy — whatever
- Ask them to red-team it, then iterate like Joanna did
Pro tip: tell the model to “roast you sometimes. The kindest thing a great mentor does is not let you get away with fuzzy thinking.
The Future Feels Both Exciting and a Little Strange
We’re probably one or two model upgrades away from indistinguishable video calls with AI versions of historical thinkers. Imagine debating capital allocation with Ben Graham or product strategy with Jony Ive.
Ethically it’s complicated. Legally it’s a minefield. Emotionally it’s powerful medicine.
But for now, on a quiet flight somewhere over middle America, a founder got the mentorship she always wished for — and built a better company because of it.
Sometimes the future shows up in the smallest moments. A laptop screen glowing in the dark, a few typed words, and suddenly the distance between ordinary and extraordinary feels a little smaller.
