Relationships Talk

In one of their first joint interviews as married entrepreneurs, Blakely and Itzler talked about how they met, why it’s important to build a life résumé, and the most important decisions they’ve ever made.

Get on Their Radar

Jesse: I first met Sara at a poker tournament. She was a customer of my company, Marquis Jet, and we met at a customer appreciation event. I knew I liked Sara, but we were only sort of friends.

I’d signed up for the USA National Ultramarathon championship. I wasn’t a huge runner at the time and had given myself 90 days to train for the event. I wanted to get on Sara’s radar, so I called her assistant. That is a theme in my life: if I want to get on someone’s radar, I cold call them, or I show up.

I called the next day and I said, “Lisa! This is Jesse Itzler, I’m about to run a 100-mile race, and I will run the entire 100 miles in Spanx for a testimonial or a donation from Sara.” [Sara laughs.]

Lisa put me on hold and told Sara a lunatic was on the phone, saying he’s going to run 100 miles in Spanx. Sara said, “I think I know that lunatic,” and a year later, we were married. You can ridicule the process, but it works!

Sara: Even now, if Jesse reads an article in the newspaper, in a magazine, or if a commercial comes on TV, he’ll want to know that person. And he literally finds them and either calls them and goes and meets with them, or sends them letters. It feels like fourth grade: “Do you want to be my friend? Check yes or no.” It’s so funny, but it’s how he operates.

Rip Up the Playbook

Jesse: I met a Navy SEAL at a 100-mile race. He weighed 285 pounds at the time and by 70 miles in, he had broken all of the bones in his feet because he weighed so much. I watched this guy duct tape both of his feet, pick himself up out of his chair, and then run another 30 miles to finish the race.

I was really interested in what makes a guy like that tick. I cold called him, and he said he would give me 15 minutes. We ended up having lunch and by the end, I’d invited him to come and live with us, and he’d said yes. Sara called that afternoon to ask about my lunch meeting, so I said it had gone great, and very quickly I said, “He’s coming to live with us.” She was like “You met him on a bus?!” And I was like no, “He’s coming to live with us . . .

On Friday.

For a month.”

Sara: That was a very fascinating time for our whole family. A lot of times in life we seem to gravitate toward common threads; the people we work with are similar, the people we went to school with are similar, and the older you get the more that happens.

Part of what I love about being married to Jesse is that he just disrupts that whole model. Having a Navy SEAL that had been living on the road out of a backpack collide with our world and live with us in our New York apartment was fascinating. He’s constantly bringing people like that home!

Jesse: Sara brings up a good point. As entrepreneurs, part of our job is to rip up the playbook. Like-minded people are amazing, but you learn so much more from people that are nothing like you. My biggest takeaway from living with a Navy SEAL, or from my recent experience living with eight monks in a monastery, is that you can incorporate their systems and perspectives and apply them to your everyday life to make you better.

I’ve always come from a place of investing in experiences. I believe in building your life résumé as well as building your business and traditional résumé, and that’s worked really well for me. Sara always says the more you experience, the more you have to offer. I’ve just tried to live my life building experiences, and I’m blessed with parents that allowed me to have that freedom, and that it led me to my wife.

Advice for Aspiring Entrepreneurs

Sara: I like to say there’s a job, a career, and a calling. As best as you can, find your calling and pursue a path that you are passionate about. If you are struggling to figure out your calling, ask yourself what makes you cry. That answer can get you close to what you’re really passionate about.

Differentiate yourself. Learn how to tell somebody in a minute or less why you’re different, why you’re the best option, and work really hard. Never underestimate how hard you’ll work. I always say start small, think big, and scale fast.

Jesse: Start the process. It’s more important to be passionate about the process than to be passionate about your product. We often try to get all the I’s dotted, T’s crossed, and get a lot of experience. I like to say that sometimes experience can be overrated. It just takes too long. As an entrepreneur in today’s fast-moving world, I’d say start. You don’t have to have all the answers figured out, but you have to start the process.

Both Blakely and Itzler appreciate that their marriage is something special. They share hopes and dreams for their four young children and have a mutual respect for each other as entrepreneurs. “We respect that each of us moves at a fast pace,” Blakely has said. “That might bother some, but we get it.”

As for the one decision that’s made the biggest impact on their lives? For each, it is the other. “Marry the right person,” Itzler advised at the end of our interview. “It is the most important decision you’ll ever make.”

Tagged Household Names, Advice, Family Entrepreneurship