Beyond the Case
A podcast where global leaders from the Harvard Business School Owner/President Management (OPM) community join in a personal capacity and share the real decisions, failures, and mental models behind building enduring companies.
This podcast is independent and not affiliated with Harvard Business School.
Beyond the Case
Sold to OpenAI: The Patience, People, and Principles Behind the Exit - Tomasz Kulakowski
He sold his company to OpenAI last month and the story behind it is a masterclass in patient entrepreneurship, long-term bets, and knowing when to start.
Tomasz Kulakowski didn’t start his entrepreneurial journey fresh out of college. He started after losing a job, being told he was “overqualified,” and asking himself a simple but dangerous question: If I’m overqualified to join, maybe I’m qualified to build.
That decision, made in his early 30s, led to multiple companies, several exits, and most recently, the sale of his AI infrastructure company to OpenAI.
Here are the Top 10 Takeaways from the conversation:
1) The hardest part of entrepreneurship is deciding to begin. Once you decide, most obstacles become solvable problems instead of excuses.
2) Job loss can be a gift. Being forced out of comfort creates the space to build something truly yours.
3) Start where you have unfair understanding. Tomasz anchored his ventures in advanced software, algorithms, and AI - domains he deeply understood.
4) Co-founders matter more than ideas. He credits early momentum to finding the right partners quickly and building with people smarter than himself.
5) Bet early on the future, not when it’s obvious. In 2014, long before AI was mainstream, his team began investing in machine learning talent and infrastructure.
6) Winning reveals opportunity. After winning a global Kaggle/NOAA competition, they realized something critical was missing: proper tooling for data scientists to collaborate, version models, and scale work.
7) Infrastructure beats hype. They built what became a “GitHub for data scientists” quietly powerful, deeply technical, and strategically valuable. OpenAI agreed.
8) Exits are fragile until the money hits the bank. Until closing, everything is risk. Due diligence is long, sensitive, and often reveals things founders themselves overlook.
9) For your first exit, optimize for closing, not ego. A slightly lower valuation is better than no deal. Your first exit buys freedom, credibility, and future leverage.
10) Wisdom = listening + sharing success. A wise leader listens more than talks, surrounds themselves with smarter people, and shares credit with the team.
His advice to younger founders?
Start earlier. Be brave. If you’re unsure—start anyway.
Entrepreneurship, as Tomasz shows, isn’t about perfect timing. It’s about committing early, compounding skill, and building with humility until opportunity finds you.
Books: Leaders Eat Last
