Why a millionaire hired a Seal to kick his butt

On a freezing 5-degree day in December 2010, Jesse Itzler found himself waist high in a frozen lake in Connecticut.

"We've got five minutes till frostbite … GET OUT NOW!" his Navy Seal house guest yelled at him.

Jesse didn't know what to think.

"Don't touch your skin to the ice as you get out — it'll stick," Seal barked.

Jesse grabbed his sneakers and used them as gloves, climbed out of the hole in the ice, and crawled across the frozen lake with his bare feet sticking up. It took him two minutes to get to land. He had about three minutes left until frostbite. Jesse started to run up a snow-covered hill barefoot and managed to get about halfway to his house when he heard:

"Don't worry, the snow will dry out your feet. We've got two minutes. RUN!"

Jesse has a list of accomplishments a mile long: He co-founded private-jet-card company Marquis Jet, then sold it to Warren Buffett's Berkshire Hathaway, and helped pioneer the coconut-water craze by partnering with Zico, which they then sold to Coca-Cola. He's a former MTV rapper, who currently is an owner of the NBA's Atlanta Hawks and is married to Spanx founder Sara Blakely.

Yet for some reason, he decided to hire a Navy Seal to kick his butt.

"Seal" and Jesse Itzler. (Crop of the book cover of "Living With a Seal." Courtesy of Center Street/Hachette. Jacket photograph courtesy of Deana Levine.)
"Seal" and Jesse Itzler. (Crop of the book cover of "Living With a Seal." Courtesy of Center Street/Hachette. Jacket photograph courtesy of Deana Levine.)
"If it doesn’t suck, we don’t do it." -Seal

Seal, as he's known in the book (to protect his identity), moved in with Jesse, Sara and their son in their Central Park West apartment in Manhattan for a month in December 2010. That winter went on to be one of the snowiest on record.

What would possess someone to do such a thing? I've known Jesse for 15 years and spoke with him weekly during the book process. When he told me about Seal, my first thought was — "Of course he's doing this. That's so Jesse." Here's how he explains it:

What made you do this?
I felt like I was drifting on autopilot in my life. Wake up, go to work, go to the gym — repeat. I wanted to shake things up. I wanted to get better.

You realize asking a very angry Navy Seal to move in with you and your family for a month isn't normal — right?
I think abnormal may be the new normal. I have always lived my life outside of the box. I find it to be way more fun there. When I met Seal, he had something that I wanted. I wasn't exactly sure what it was at the time, but I knew that having him around me for a period of time would make aspects of my life dramatically better. At the time, that felt perfectly normal.

You have houses, a driver and fly by private jet. Seal, as you describe him in the book, had only a military ID, cash and a backpack. What was it that he had that you wanted?

It actually had nothing to do with money at all. I was after the psychological side of Seal. What makes him tick? Where does all his drive and motivation come from? This was a man that had a focus unlike anything I had ever seen. I wanted to learn more about that mindset and apply it to my life. Interestingly, I learned that some of his drive and good habits are tied to the simplicity of his life. Not that I'm going to sell everything and live out of a backpack, but I learned a lot of valuable life lessons.

How did you find a Seal in the first place?

I first saw Seal at a race in San Diego. I was on a team of six that was going to run for 24 hours straight. Seal was on a team by himself. He did the entire race alone. I knew I had to meet this guy.

How did Seal train you? Describe a typical day with Seal.
The one condition he gave me in order to move in was that nothing was off-limits — I had to do anything and everything he said. No day was like the other. The only consistency was it was going to be a very difficult day.

He pushed my limits in all aspects of my life. We jumped in a frozen lake, I had to sleep in a chair one night and we woke up at all hours of the night to train.

What was the hardest part or moment from your time with Seal?

Well, I definitely didn't like getting up at all hours of the night. I didn't like jumping in a frozen lake either. However, the hardest thing for me was trying to keep up with Seal's "no excuses" attitude. There were plenty of days that I just wanted to stay in bed and take the day off, but there would be none of that. It's way easier to slack then it is to commit and Seal was focused on teaching me that slacking is never an option. He would say "We do things with 110-percent effort or we don't do them."

You mentioned one of the reasons you hired Seal was to shock your system. Was it shocked?
Absolutely. So many of us live our lives on autopilot. We wake up, go to work, have dinner, go to sleep …repeat. When I found myself drifting in that direction, I needed shock to the system. Seal's nomadic lifestyle clashing with my upper west side lifestyle was exactly what I needed. It was unorthodox and unexpected, but research shows that stepping out of your comfort zone and mixing it up is good for your mind and your body. He didn't just shock my system, he jump-started it!

Jesse Itzler
Photo: Chris Hamilton Photography
Jesse Itzler

How has this experience changed you?
One of my big takeaways from my time with Seal was the level of appreciation he has for difficulty. The harder the task or the challenge, the more satisfaction Seal got out of it and the more alive he felt. One of his favorite sayings was "If it doesn't suck, we don't do it." He taught me that in order to get better you have to get comfortable being uncomfortable. I try to take that "do more" spirit with me in everything I do.

How has it changed your approach to life, business and risk-taking?
When Seal lived with me, I was in awe with how much we were able to accomplish in a day. It was like everyone else was playing with 24 hours and we had 27. Sure we got up early, but it's amazing how much more time frees up when you eliminate the non-essential stuff in your routine. He took the concept of no dilly-dallying to another level. I have been able to incorporate that into my daily routine and it has made me way more efficient.

A lot of people know who your wife is — especially the CNBC audience. What did she say when you told her you wanted an accomplished Navy Seal, also widely known as the "toughest man on the planet" living with your family?
It's interesting, the things that would completely faze a lot of people, don't faze Sara. She has lived her life so outside of the box that nothing surprises her. Plus she loves to try new things and put herself out there. So, she was completely supportive. I married the right girl!

In the history of entrepreneurship, sometimes failing has led to some of the greatest successes in business. How has failure played a role in your experience?
I try and step out of my comfort zone on a daily basis, it's part of my DNA. As an entrepreneur you are constantly playing in uncharted territory and sometimes things don't work out. That doesn't mean you failed, it just means you may be off course. Failure has never been a signal for me to quit, it's always been a sign for me to go down another path.

What is your greatest failure? And what did you learn or where did it lead you?
This is going to sound crazy but one fail on my part that I still regret was not trying out for my high school basketball team. I wasn't scared of NOT making the team, I was actually scared OF making the team and that fear stopped me from playing. I regretted that decision after the fact and promised myself I would never let fear stop me from doing something I really wanted to do again.

"Living with a Seal: 31 Days Training With the Toughest Man on the Planet" is due out on Nov. 3.

Commentary by Turney Duff, a former trader at the hedge fund Galleon Group. Duff chronicled the spectacular rise and fall of his career on Wall Street in the book, "The Buy Side." He's also a consultant on the upcoming Showtime show, "Billions," starring Damian Lewis and Paul Giamatti. Follow him on Twitter @turneyduff.

Correction: Jesse Itzler is not a billionaire. His wealth was mischaracterized by the author in the headline of a previous version of this article.