Make

The Ultimate Partnership

By Richard Bradley

Entrepreneurs Sara Blakely and Jesse Itzler discuss how to combine work, wealth and family.

Only in retrospect does the partnership—which is to say, marriage—of Sara Blakely and Jesse Itzler seem inevitable. When the two entrepreneurs first met, both were immersed in demanding, high-powered careers. Blakely, now 39, was the founder of the enormously successful clothing company Spanx, which she created with an idea (women want flattering undergarments), a product (pantyhose without feet) and dogged persistence (for the company’s first three years, Spanx packaging featured a picture of Blakely’s Spanx-clad rear end).

Jesse Itzler, now 42, had followed a similarly unorthodox path to success. As a white teenager growing up in Roslyn, Long Island, Itzler decided that rap was his calling, and had some commercial success with music he recorded under the name Jesse Jaymes. Following that, he wrote the irritatingly catchy New York Knicks theme song—“Go New York Go!”—created the NBA slogan—“I love this game!”—and co-founded with friend Kenny Dichter a record label selling compilations of sports-related music. While traveling for work, the two came up with the idea of a company that let business travelers buy time on private jets. That led in 2001 to the founding of Marquis Jet, which sells jet “cards” worth 25 hours of time on a Net Jets plane. Marquis now has about 4,000 cardholders who pay a minimum of $116,000 per card. More recently, Itzler has started a new business, branding firm Suite 850.

Being successful and wealthy has its advantages, but it can also pose major problems for romantic relationships. How did Blakely and Itzler, who were married at Boca Grande’s Gasparilla Inn in October 2008, avoid the pitfalls? Worth sat down with them—and, until naptime, their baby boy Lazer—at their New Fairfield, Conn., country home to find out.

How did you meet?

Sara: We met at a poker tournament in Vegas in 2006. I had purchased my first 25-hour Marquis card, and the Marquis sales rep kept saying, “You’ve got to meet the co-founder of our business.” So I flew to Vegas and met him.

Jesse: The rep called me and said, “I want to invite one of my customers to this NetJets-Marquis poker tournament.” I explained that we were sold out. She said, “Go to this girl’s website.” I saw the picture and was like, “She can play.”

Did you have much in common?

Sara: We grew up in different worlds. I’m from Clearwater Beach, Fla.; Jesse grew up in Roslyn, N.Y. But we both had unconventional paths to success and entrepreneurship. Neither of us took business classes. Jesse went from being a rapper to writing sports songs to helping start Marquis Jet. I tried out to be Goofy at Disney World, but I was too short, so they made me a chipmunk. Then I became a stand-up comedian at night, and I sold pantyhose door to door for seven years. We started our entrepreneurship journey the same year, 2000. Was it appealing that you were both successful? Jesse: What was appealing was that we were both very independent. Neither was clingy. Sara: It was just such a relief to meet a match in that area of life, because a lot of the men I had dated hadn’t reached where they wanted to be financially or professionally. And would you talk about those issues with them?

Sara: You have the conversation in the beginning, and they say, “It doesn’t bother me,” and I say, “It doesn’t bother me,” and then it somehow becomes clear that it bothers either them or me.

So the differences in financial and professional success were a problem?

Sara: Jesse was the first person I had ever really dated where I didn’t feel like I was carrying the load.

Had you dated men who were successful but didn’t like that you were as successful as they were?

Sara: Yeah. And I also dated some men who were equally successful but it wasn’t their money, it was family money, and that created an even bigger issue: I felt like I was a constant reminder that they hadn’t earned their money on their own.

So the timing was good for both of you because you were at similar places in life.

Jesse: We didn’t meet when we were 21. We’d already fought business wars. We went through the start-up days. We met when our businesses were established.

Would your relationship have worked if you had met in, say, 2001?

Jesse: Either the relationship would have worked and the business wouldn’t have, or the business would’ve worked and this wouldn’t have. Because it takes so much effort to start what Sara built single-handedly and what I had to go through at Marquis with my partner. Years later, I’m exhausted. It was six in the morning to 11 at night, every day.

Even by 2006, your work lives must have been demanding. And you lived in different cities—Atlanta and New York. How did you date under those circumstances?

Jesse: We both had great management in place, so we had more freedom. We basically put everything on hold, business-wise, for six months.

Sara: We were old enough to know that how we felt about each other was really rare and we didn’t want to waste it by not prioritizing it. We just did whatever we needed to do to be together.

How were you able to disengage from your business? Because there are always people who want to pull you back in, right?

Jesse: I had a harder time than Sara did. I had a group of partners. Sara: I don’t have any partners.

Sara: I don’t have any partners. I’m the sole owner of the business. I have an amazing CEO and I had already stepped away from the business. Now, I’m the face of the brand, so that didn’t go away. What went away was me being at the office every day. I was on the phone and email more.

Since you’re both entrepreneurs, do you brainstorm together or bounce ideas off each other?

Jesse: Way more me to her. But work is not the number one priority in our life.

So you don’t talk about work a lot?

Sara: With other people I dated, I’d get home and there’d be a lot of questions [about work]. And then they’d get frustrated with me when I’d say, “I don’t want to talk about it.”

Jesse: In the beginning, you want to tell your story to everybody—“This is how I started.” It’s exciting. But after several years, when someone says, “How did you help start Marquis?” you can’t even get the words out of your mouth.

What are your roles in your businesses now?

Sara: I give a lot of input in the marketing, the product development ideas and sales. I’m on the road a lot. Women can relate to me, so I’m out there PR-ing.

Jesse: I started a new venture, Suite 850, about 18 months ago. I’m back in that start-up mentality. But at the same time, I’ve made commitments that I’m going to be home at a certain time. If Sara says, “I need you home by 6” when previously I’d be home at 11, I have to squeeze it all in.

Jesse, do you ever worry that starting a business requires that 6 a.m. to 11 p.m. commitment and that maybe you don’t have that edge anymore? That you’re not hungry enough?

Jesse: I have the edge. I have the hunger. I just don’t have the time. So I hire people who are hungrier and have more availability than I do.

For virtually every couple, money is an issue, and you’ve both made a lot of it. What were the challenges for you?

Jesse: We’ve never made it a huge issue. We never sat down and said, “We’re going to do x, y and z.”

But you must have had a financial advisor who said, “You’ve got to have that conversation.”

Jesse: We never had a sit-down with a team of advisors.

Sara: Are you talking about a prenup?

Yes, but also the more general questions— your life is changing, your financial planning should change.

Sara: When two people come to the table with their own money and their own thing going on, it’s like nothing’s changed. I still have my own money. I buy whatever I want when I want. He does the same thing.

So did you have a prenup?

Sara: We did. Our lawyers hashed it out, and after Jesse signed it he said, “I never read it,” and I said, “I didn’t either.”

Jesse: It’s a very weird dynamic. You’re 40 years old; you’re about to get married; you can’t envision anything going wrong in the relationship.

And you’re tasked with this thing—“In case it doesn’t work out, we’re going to do this.” I didn’t want to turn it into something that could be awkward or a conflict, so we kept it very simple.

Any advice for people who are—or are about to be—in your situation?

Jesse: Don’t let work ever interfere.

Sara: We slow dance if we ever get into an argument.

Really? That’s sweet.

Sara: Jesse came up with that idea.

Jesse: I’m like, “Sara, are you yelling at me? Get over here and slow dance.”

Sara: Something about slow dancing … There’s the physical contact, and you just realize: You’re in this together.