The Extreme Personality Who Turned Survival Into a Movement — The Lonely Entrepreneur
Michael Dermer left one of the most prestigious law firms in the world to invent what didn’t exist. Then 2008 nearly erased a decade of work in 10 days. What followed wasn’t balance — it was extremism. What emerged wasn’t just a successful exit and a new industry. It was a movement. Unlocked by one of the extreme personalities of our time. Now he is helping entrepreneurs answer the question on everyone’s mind — will you survive AI?
“We are all lonely entrepreneurs.”
BackgroundTwo-time Academic All-American. Wired early. A two-time Academic All-American baseball player, Michael practiced without a glove to sharpen his skills. Extreme habits in his DNA. He then joined Willkie Farr & Gallagher — one of the most prestigious law firms in the world — and walked away. |
Invented an IndustryThey told him it would never work. Michael left Willkie Farr — and a life of prosperity — for a vision. They said “we will never pay people to be healthy.” He built IncentOne anyway — the first company to reward people for healthy behavior. What didn’t exist became an industry. |
2008: The CollapseTen years of work — gone in ten days. Michael built IncentOne to 800 employees over 10 years. When 2008 hit, it was nearly destroyed in 10 days. Clients collapsed. Contracts vanished. This is where most stories end. Not his. It led to a successful exit and the beginning of a movement. |
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3 Years of 20-Hour DaysYou don’t manage collapse. You outlast it. For three years during the financial crisis, Michael lived 20-hour days with no end in sight. “You got kicked between the legs 20 times a day. You just stopped noticing.” The result — an exit and the invention of an industry. |
Cold Shower: 5 MinutesIt started by mistake. And became a ritual to test his limits. One day after his normal 5 a.m. workout, the gym’s shower produced only freezing water. He didn’t flinch. Instead, he thought, “if I could endure this, I could face anything the day would bring.” Five minutes in freezing water every morning for two years. And every day since. |
Starbucks Origin“Who here is a lonely entrepreneur?” After the sale of IncentOne, an entrepreneur Michael was helping said “being an entrepreneur is lonely.” After telling a friend two weeks later, the friend walked into a Starbucks and said “watch this.” He yelled “who here is a lonely entrepreneur?” Every hand went up. The movement — and Michael’s true mission — was born. |
Unlock a MovementWe are all lonely entrepreneurs. The Lonely Entrepreneur gave language to something universal. What Sex and the City did for women wasn’t inventing experience. It was naming it — publicly, honestly, without apology. The Lonely Entrepreneur did the same for founders. Once the phrase existed, people didn’t feel weak. They felt seen. |
“People say Taylor Swift connects because young women feel like she’s talking to them in their bedrooms. Michael is the same for entrepreneurs. What he says is what we all feel every day.”
Extreme DisciplineNot most days. Every day.
These aren’t stunts — they’re identity. |
Yoga On the EdgeMost people would snap. A yoga practice that would make most people snap. Extreme flexibility only seen in gymnasts and professional ballet dancers. Stretch your limits or your ceiling becomes your coffin. |
Workouts On the EdgeMost people would redline. A test of tolerance — for discomfort, repetition, and pressure. And calves from outer space. Every day for 38 years. |
Dedicated to His ChildrenMost people have children. I have entrepreneurs. Never married. No kids. Entrepreneurs are his family. Not because he couldn’t — because he chose something else. His mission is to help founders turn passion into success. “Most people see their child’s first steps. I see 1000s of first steps every day.” |
Global VoiceWe are all lonely entrepreneurs. United States. Europe. Middle East. Asia. Africa. Michael’s message resonated everywhere not because it was his, but because it is theirs. Walk into a Starbucks in Shanghai, Dubai, London or Barcelona and yell “who here is a lonely entrepreneur?” |
AROUND THE WORLD
The Lonely Entrepreneur’s Guide To Business Success
How to Lead Through Crisis with Michael Dermer
Michael Dermer highlights The Lonely Entrepreneur
STEVE MADDEN AND MICHAEL ON CRISIS
BRANDON STEINER AND MICHAEL TALK ENTREPRENEURS
HEALTHY LIVING
DAVE MELTZER
ENTREPRENEUR MAGAZINE INTERVIEW
ASCENT AND DREW TARVIN
CITY CURRENT INTERVIEWS MICHAEL
WFAN INTERVIEW
SUCCESS WITH RADICAL INNOVATIONS / PLAYGROUND
BLACK ENTREPRENEUR INITIATIVE — GAINESVILLE
Survival → Extremism → Movement
Michael Dermer built what didn’t exist, nearly lost it all in 2008, and rebuilt through extreme discipline. What followed wasn’t balance — it was extremism. What emerged wasn’t just a successful exit and a new industry. It was a movement. Unlocked by one of the extreme personalities of our time. Now he is helping entrepreneurs answer the question on everyone’s mind — will you survive AI?

- Two-time Academic All-American.
- Joined Willkie Farr & Gallagher — then walked away.
- “We’ll never pay people to be healthy.”
- He built IncentOne anyway.
Clients collapsed. Contracts vanished. Most stories end there. His didn’t.
Three years. No end in sight. “You got kicked 20 times a day. You stopped noticing.”
Five minutes in freezing water every morning since October 2008.
Every hand went up. The movement had a name — and people felt seen.
- 38 years without missing a workout.
- No carbs for 30+ years.
Not stunts — identity.
Stretch your limits or your ceiling becomes your coffin.
Every day for 38 years. Calves from outer space.
“People say Taylor Swift connects because young women feel like she’s talking to them in their bedrooms. Michael is the same for entrepreneurs. What he says is what we all feel every day.”
Short clips from Michael’s story, crisis lessons, and the movement.
