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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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In this episode, Sohin Shah sits down with Mathieu Roegiers, a Belgian entrepreneur who has already lived three careers: professional field hockey player, 777 captain for Etihad Airways, and now founder of Cosmos Fund.
He takes us into the cockpit during a brutal flight through extreme weather, when a 26-year-old Mathieu had to fly the aircraft alone. That moment, along with years of intense simulator training, shaped his decision-making style: identify the biggest risk, act quickly with imperfect information, and compartmentalize.
When COVID grounded global aviation, Mathieu lost his job. Instead of breaking, he used the reset to pivot into entrepreneurship, building a luxury property development and management business in Bali.
Mathieu also reflects on his time at Harvard Business School’s OPM program - especially the two competing schools of thought he encountered: building businesses to last vs. building businesses to sell, and how that reframed his sense of long-term value.
Here are the Top 10 Takeaways from the conversation:
1. Reinvention is a skill, not an event.
Mathieu has lived three full professional lives - athlete, airline captain, entrepreneur. Each pivot required humility, discomfort, and starting from zero, proving reinvention is a muscle you build.
2. Leadership shows up when the title disappears.
His definition of leadership: people follow you even when you don’t have authority. The best leaders give responsibility, not orders, and they don’t need the spotlight.
3. Calm is a competitive advantage.
In the cockpit, when a senior captain froze in extreme weather, Mathieu - 26 years old - took over. His calm wasn’t talent; it was trained under pressure over years.
4. You can always reset the situation.
His story about confronting the worst captain in the company - and then turning it into the best flight of his career - reminds us that almost any relationship can be reset if someone is willing to own the moment.
5. Prioritization = survival.
Aviation teaches ruthless focus: handle the biggest fire first, then the next one. Leaders often drown in data; Mathieu focuses on “the next right decision.”
6. Comfort is the enemy of growth.
He applied to Harvard Business School’s OPM not because he thought he belonged, but because it scared him. He thrives outside the comfort zone - and credits discomfort for every major leap.
7. Don’t pivot alone.
Mathieu says his transition from aviation to real estate only worked because he had partners who balanced him. His formula: find people smarter than you in the domain you want to enter.
8. Take bigger swings early in life.
If he could go back to age 20, he’d take more risks. When you’re young and responsibility-light, “the sky is not the limit” - your imagination is.
9. Don’t marry your beliefs forever.
He openly admits he changes his mind often. Sticking to one lifelong belief, he says, is “not a healthy principle.” Adaptability beats stubbornness.
10. Build to last… but don’t ignore exits.
Before HBS, he only thought in “build forever” terms. Professor Das’s frameworks made him rethink the strategic value of building to sell - and keeping both lenses on the table.
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