Wheels Up: Takeoff, Landing, and the Most Dangerous Part

About this episode

Matt Stone discusses the flight analogy for starting new ventures, emphasizing the vulnerabilities during takeoff and landing.

Fifty-four days until summer, and Matt’s got a feeling they’re going straight from late winter into the Hades era of heat. Welcome to Backstage—he likes the art, hopes you do too, sticking with it for a while. After sharing trivia about the yellow fever vaccine (1932—back when vaccines were seen as positive), Charles de Gaulle resigning (1969), and A Chorus Line closing after 6,137 performances (1990), he dives into the flight analogy that’s been on his mind. Flying has always been exciting since he was a kid—first plane ride probably when his father was deployed to Europe, TWA, smoking on the plane where the only difference between smoking and non-smoking was the seat number. Flight is a great analogy for starting a new venture. The Bigger Stage is a few months old, still an infant. The plane has left the tarmac, back wheels are off the ground. Great. But here’s the thing: takeoff and landing are the most dangerous parts of a flight, when most crashes happen. Like car crashes in parking lots near your home, not on the freeway. It’s normal to feel very vulnerable after takeoff because you are vulnerable. It’s precarious—you’ve got to believe the parachute will deploy. Usually…

People in this episode

Host: Matt Stone

Topics covered

• flight analogy
• starting a new venture
• vulnerability in business
• fundraising
• operator-to-icon shift

Keywords

• flight analogy
• business venture
• fundraising
• vulnerability
• entrepreneurship

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• Start With a New Story · September 4, 2026 · 10 min
• People Love to Be Sold To · September 3, 2026 · 10 min
• Lead the Whole Industry · September 2, 2026 · 10 min
• A Different Font · September 1, 2026 · 13 min
• Take Them on a Field Trip · August 31, 2026 · 12 min