Should an entrepreneur ever marry, given the higher-than-usual likelihood of divorce? Maybe the best bet is to marry another entrepreneur.

The world is abuzz today with the news that Karlie Kloss is engaged to Josh Kushner. Kloss, best known as a supermodel, is also the founder of Kode With Klossy, a summer camp scholarship program to teach girls programming skills. Kushner is the founder of investment firm Thrive Capital and the co-founder of Oscar Health. He is also, of course, brother to Jared Kushner, President Donald Trump's son-in-law and advisor. 

The two had been a couple for six years before Kushner popped the question during a romantic weekend in Upstate New York. In addition to (presumably) giving him a verbal answer, Kloss, who is a social media powerhouse, also Instagrammed her response, "I can't wait for forever together. Yes a million times over." 

With divorce rates somewhere between 40 and 50 percent, any new marriage is an uncertain proposition. But the fact that Kloss and Kushner have already spent six years as a couple--and the fact that they're both entrepreneurs--may give them a fighting chance to make their marriage a success.

Married to your startup?

Marrying an entrepreneur is a famously dicey proposition. Most are first and foremost married to their companies, leaving their actual spouses feeling like second best. The nonstop demands of running a company mean entrepreneurs often work evenings and weekends, and may have heavy travel schedules that frequently take them away from home. And even when they are home, their minds are often somewhere else, because when you run a company it's difficult or impossible to leave work at work.

It just might be that the best solution to this dilemma is for entrepreneurs to marry each other. A spouse who is preoccupied with his or her own startup is less likely to take offense if you spend long hours at the office and are constantly thinking about work. As a fellow entrepreneur, your spouse may be able to give you useful advice when you're faced with a business problem. Even if not, you'll have the comfort of talking to someone who knows exactly what you're going through.

Besides (unless, like Kloss, it's your side hustle), entrepreneurship is a fundamentally risky approach to earning a living. The worst conflicts between entrepreneurs and their spouses are typically arguments over money, because starting a business not only means you won't be bringing in a salary for a long time, but often that you've liquidated the family savings, or gone into debt to fund your endeavor. Since the majority of startups don't survive, a husband or wife might be understandably unhappy about taking that kind of financial risk. 

But marry another entrepreneur, and you're partnering with someone whose attitude toward financial risk may be very similar to your own. Your spouse will have a better chance of understanding why you want to max out the credit cards and take out a home equity loan if that spouse has done the same thing when starting his or her own business. Or if that spouse hopes to do so in the future once your business is self-sustaining. (It's probably a bad idea to go into massive personal debt for both businesses at once, so if you're both looking to start up at the same time, you may need to decide which partner gets to go first.)

Here are two other two-entrepreneur couples who, like Kloss and Kushner, look like they're making it work:

Sara Blakely and Jesse Itzler

Spanx founder and former Shark Tank shark Sara Blakely married Jesse Itzler, co-founder of Marquis Jet, former rapper, and author whose most recent adventures involve having a Navy SEAL move in and train him, living with monks, climbing Vermont's Stratton Mountain 17 times in a row, and running 100 miles in an ultramarathon.

The two met at a charity poker event in Las Vegas. She had spotted him from afar and decided she'd like to meet him earlier that day. He was intrigued that she went to bed at 9:30, even though they were in Vegas. "That intrigued me," he said

They emailed each other for a while and began dating. He would tell her that he could marry her, and she would respond "Bring it!" Eventually, he proposed with a gold band that said "BRING IT!!" (He had several other rings hidden around their apartment, including an emerald engagement ring.)

The two are very different. He's a health fanatic who eats fruit all day while Blakely claims to indulge in candy bars and Cheez-Its. They've told several media outlets that their trick to defuse serious arguments is to stop and slow dance for a minute or so. But, both being entrepreneurs, they have one important thing in common. "We respect that each of us moves at a fast pace," Blakely said in an interview. "That might bother some, but we get it."

Dennis and Chelsa Crowley

Dennis is the co-founder and executive chairman of Foursquare. Chelsa is co-founder and creative director of the fashion startup Stowaway, which makes small-sized cosmetics that are both more portable and more practical than the more usual sizes. The company won my heart with a simple question that might resonate for most women: "When was the last time you finished a lipstick?" 

In true Internet fashion, Dennis first noticed Chelsa before they met, when she began showing up in a friend's Flickr feed. He knew he wanted to hang out with her and so was eager when she later turned up at his annual tree-trimming party. "She's the first person I've ever met who I have trouble keeping up with," he told the Times when they married in 2013. 

Their friends say that she's the girl version of him and he's the boy version of her, and that it's cute that they seem to want to do everything together. So much so that they got in trouble for their joint participation in the 2014 Boston Marathon. A year earlier, a terrorist attack disrupted the marathon such that Chelsa was able to complete the race but Dennis was not, and the two were separated. The couple really, really wanted to finish the race together in 2014. Because the attack stopped him from completing the race in 2013, Dennis was automatically allowed to run the following year, but despite their attempts, she was not able to get a race number for 2014. So he simply forged one for her so they could run together.

It seemed like no big deal to them--they blithely posted pictures of themselves with their numbers at the finish line to social media. And that's how they got caught: The real owner of Chelsa's fake race number was aghast to see pictures of someone else wearing the same number she had, and she quickly called out the deception. 

It was a black mark for which Dennis had to quickly and profusely apologize. To those affected by the Boston Marathon bombing, it was indeed inexcusable. But it was also sweet to note that, when so many entrepreneur's marriages fail, this couple's biggest misstep came about because they really wanted to be together. 

Published on: Jul 24, 2018
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