The Business of Love

A look inside how the world’s most powerful entrepreneurs master life and love.

As an Executive Matchmaker, I work with entrepreneurs from founders to musicians, athletes, and politicians. They all lead busy lives in and out of work and, naturally, expect no less in a partner.

When we meet, I advise, “If you think dating has been hard, try a relationship with someone with an equally, if not more, demanding lifestyle than you.” We persist in their quest for a co-equals nonetheless, but the real work begins when they fall in love. Then, what happens?

Ask Google, of course!

But Google results only provide quick fixes to dating an entrepreneur, including one that I see all too often: just break up. You see, the results are the problem. Love requires more than just a quick fix remedy. A break up is often not the right resolution.

I’ve read hundreds of articles and been left to my own devices to learn how to navigate such a deep and dynamic lifestyle. Until now, I have yet to provide an universal understanding of the mechanics that go into a successful entrepreneurial relationship.

1. Similar Values are Key

Melinda Gates tells Business Insider, “We agree on basic values. For our wedding, Bill’s parents gave us a sculpture of two birds side by side, staring at the horizon, and it’s still in front of our house. I think of it all the time, because life gets busy, but we’re still fundamentally we’re looking in the same direction.

So, how do you maintain the same direction in a busy world? At times, an entrepreneurs’ mind is completely consumed with work - a new idea, launch, or partnership. Whatever it is, they’ll forget to eat, sleep, and won’t be able to get it off their mind for days, weeks, — maybe months.

However, an entrepreneur’s debilitating focus does not make them blind to the world around them. A good man or woman is aware their relationship may be slipping, and they feel really guilty about it, but they always come around.

The key to continual advancement in your relationship is valuing what each other values. Be patient, encouraging, and give your partner grace, especially during the busy seasons.

2. Dare to Be Different

On meeting his future wife, Amal Clooney, George Clooney tells Vogue, “If you know anything about my crazy life, you know that I’d pretty much committed to the idea of never marrying again. But I started dating Amal, and I immediately knew that something was very different.”

He adds, “Of course she was beautiful, but I also thought she was fascinating… I thought she was brilliant. Her life was incredibly exciting—the clients she was taking on and the superhuman work that she was doing. I was taken with her from the moment I saw her.”

A relationship with an entrepreneur is riddled with the highest peaks and lowest valleys. There may be weeks where you feel as if you or your partner has fallen off the face of the planet and others where you’ll never have felt more loved in your entire life. Together, you’ll have the most fascinating experiences, conversations, and introductions to people who truly change the world.

When you’re dating an entrepreneur, you’re playing the long game. In a modern world of immediate gratification, enjoy the journey and dare to be different.

3. Accept Each Other

Sara Blakely, CEO of SPANX, adds with the New York Times, ‘I’ve learned it’s important not trying to change someone, and not trying to understand him, just love him. I’m along for the ride. So is he. We have each other’s back and are each other’s cheerleaders.’

I believe there is nothing more attractive than loving someone with undying passion and a relentless pursuit for what and whom they love, even if it means they don’t fit the traditional mold of a boyfriend or girlfriend. Once you accept your partner for who he or she is, your relationship will improve a tenfold.

4. Independence is a Must

Discover your own passions. Work on your own business. Give your partner space to think and strategize without them worrying about getting home at a certain hour. In order to successfully love a high performer, you must be own yourself - in your own right.

Jesse Itzler, NYT Bestseller and Co-Founder of Marquis Jet, dotes on his wife, Sara, saying, ‘She’s a human adventure. There’s always excitement and newness. I have a very good understanding of what makes her tick, and she has that for me. And she allows me to do things I want to, and vice versa. That takes away a lot of potential for resentment. We also understand each other’s needs.

Another key? Separate bathrooms.

Former FLOTUS, Michelle Obama, tells Bustle, "One of the keys to a successful marriage is separate bathrooms," Obama said. "When [Barack Obama] enters my bathrooms, sometimes I'm like, 'Why are you in here?' And he's like, 'I live here. Can I enjoy my bathroom too?'"

5. Be Resourceful

Jeff Bezos, Founder and CEO of Amazon.com once called himself a “professional dater.” He wanted a resourceful woman. “The number-one criterion was that I wanted a woman who could get me out of a Third World prison,” he said. “Life’s too short to hang out with people who aren’t resourceful.” 

In fact, Jeff wasn't alone when he made his cross-county road trip to Seattle in 1994. And he wasn't alone when he founded Amazon, his wife MacKenzie was there for the whole journey.

6. Own Your Yin-and-Yang

“Jeff is the opposite of me,” Bezos told Vogue. “He likes to meet people. He’s a very social guy. Cocktail parties for me can be nerve-racking. The brevity of conversations, the number of them—it’s not my sweet spot.” On the other hand, Jeff Bezos made a reputation as an extrovert, one who can make anyone feel at ease. “Jeff is obviously the extrovert who can make a speech on the spur of the moment; she is the one who is constantly observing,” said Danny Hillis, a longtime friend of the couple’s.

Sara agrees, saying, “He [Jesse] eats fruit until noon, I don't. He likes old school rap, I like old school 70s & 80s. He's a New Yorker, I grew up on Clearwater Beach, Fl. He can run 100 miles, I can run 1. I live to eat, he eats just to live.” No matter, choose to see your partner’s brilliance and support each other’s differences.

7. Have Mutual Respect

Melinda Gates, Philanthropist and Co-Founder of the Bill & Melinda Gates Foundation, admitted her mother didn’t think it was a great idea to date Microsoft CEO, Bill Gates. However, she didn’t listen. ‘"When I look back, Bill was the same kind of guy I was hanging out with in college," Melinda says. "I had a lot of respect for them, and they had respect for me.”. Melinda has said her relationship with her husband has changed over time. "We've had to change to really be coequals," she says. "It's not something that immediately happens overnight, but we're both committed to it."

8. Balance, Balance, Balance

Learning how to ‘balance the busy’ is difficult and can be quite time consuming, ironically. That’s because balance will look and feel radically different depending on the breadth and depth of obligations you both need to manage at any given time. Communicating what your needs (re: values) is the first step to creating a successful balancing act with your partner.

Jeff Bezos always starts his day with a healthy breakfast with his wife and kids before they head off to school. He never schedules early meetings. If it must, let the chaos be chaos, but we choose the begin and end our days peacefully with each other.

Michelle Obama tells Glamour, "When the kids go to bed and after he's done a little reading, we're usually curled up in our den, and we'll watch a show together. Or we'll talk and catch up. It's nothing major, but that's what marriage is about. Not the big, splashy stuff. It's just the little day-to-day sharing and routines and rituals that we still have."


In the end, it all boils down to this: we’re human beings. We all crave love, touch, and connection, even when we’re locked away with competing priorities.

That being said, entrepreneurs are likely to put our business before much of anything in our personal lives. At one extreme, they forget to eat, sleep, shower, and even socialize. At the other, they take better care of ourselves and our relationships than 99.9% of the general population. They’ll disappear, reappear, dive deep, and run away all within a moment’s notice.

But in the end, that’s just their way of saying, “I love you.”