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?

Yoga — most people would snap

“We are all lonely entrepreneurs.”

Background

Two-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 Industry

They 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 Collapse

Ten 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.

3 Years of 20-Hour Days

You 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 Minutes

It 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 Movement

We 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 Discipline

Not most days. Every day.

  • 38 years without missing a workout day.
  • No carbs in 30 years.
  • 5-minute freezing cold shower every morning since October 2008.
  • Walks backwards up five flights of stairs daily.

These aren’t stunts — they’re identity.

Yoga On the Edge

Most 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 Edge

Most people would redline.

A test of tolerance — for discomfort, repetition, and pressure. And calves from outer space.

Every day for 38 years.

Workouts image

IMAGE COMING SOON

Dedicated to His Children

Most 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 Voice

We 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?

Michael Dermer — Yoga on the edge


Background
Wired for extremes.
  • Two-time Academic All-American.
  • Joined Willkie Farr & Gallagher — then walked away.

Invented an Industry
Built what didn’t exist.
  • “We’ll never pay people to be healthy.”
  • He built IncentOne anyway.

2008: The Collapse
Ten years — nearly erased in ten days.

Clients collapsed. Contracts vanished. Most stories end there. His didn’t.

MICHAEL’S JOURNEY — THE PERFECT STORM

20-Hour Days
You don’t manage collapse. You outlast it.

Three years. No end in sight. “You got kicked 20 times a day. You stopped noticing.”

Cold Shower
A ritual to test limits.

Five minutes in freezing water every morning since October 2008.

Starbucks Origin
“Who here is a lonely entrepreneur?”

Every hand went up. The movement had a name — and people felt seen.

Extreme Discipline
  • 38 years without missing a workout.
  • No carbs for 30+ years.

Not stunts — identity.

Yoga On the Edge
Most people would snap.

Stretch your limits or your ceiling becomes your coffin.

Workouts On the Edge
Most people would redline.

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.”

Video Library

Short clips from Michael’s story, crisis lessons, and the movement.