Eight Things to Know Before Dating An Entrepreneur

Entrepreneurs are their own breed of boyfriend.

Dating someone on the precipice of professional life or death is both fantastically enlightening and a huge pain in the ass. As the great and mighty Elon Musk says, “Starting a company is like eating glass and staring into the abyss.”

Kind of sexy, no?

There are a few quirks inherent in the entrepreneurial personality you should understand as a mate. Whether he’s the founder of a startup, owner of a brick-and-mortar business, or a professional who has found a way to write his own paycheck, here’s what you need to know to make it work with one of these crazy kids.

(Note: This is written from my perspective as a woman, but the same is true for men dating lady bosses).


If you’re dating an entrepreneur, you should try to get your sh** together.

The only significant predictor of a company surviving for more than 8 years is the founders level of conscientiousness. Entrepreneurs are planners, strategists, goal-setters, and organizers. They’re neurotic about time, space, diets, and co-workers. And for better or worse, they’ll probably expect the same from you.

I’ve been made to feel like an #adultfail for making the bed “halfway,” forgetting an ingredient required to cook dinner, feeling too tired to attend our social commitment, or not packing a sundress to meet mom. But this obnoxious conscientiousness wins them points for remembering birthdays, following up on promises, and doling out praise when deserved.

Try not to take the criticism personally. Conscientiousness means his company’s trains run on time. But do spruce up the areas of your life patched together with duct-tape before you let him in. You’ll thank me later.


If you’re dating an entrepreneur, your world will probably explode.

Each day is met with a new proclamation: “I’ve decided to eat blueberries and cricket powder for a month,” “I want to scale volcanos in Indonesia,” “I’m starting a new side project that should only take an extra 30 hours a week.”

Entrepreneurs are known for their schizophrenic array of hobbies, experiments, and personality quirks. A 2013 Swiss-German study found that entrepreneurs are more likely to be generalists and “Jacks of all Trades,” which means they bring a colorful assortment of skills, networks, and idiosyncratic obsessions to a relationship.

So use kid gloves. If you’re not cognitively flexible, tolerant of change, and extremely patient, you probably shouldn’t date an entrepreneur. As psychologist John Gartner says, “They’re like border collies–they have to run. If you keep them inside, they chew up the furniture.”


If you’re dating an entrepreneur, you might be dating an asshole.

Entrepreneurs are famous for being a disagreeable bunch. I’ve dated them, worked with them, heard the horror stories, and witnessed the prickly exchanges.

But they’re often assholes out of necessity. The willingness to take social risks, speak the brutal truth, turn people down, and do the unpopular thing gives them an IDGAF advantage. Malcolm Gladwell insists innovators are naturally more disagreeable because they don’t have the time, energy, or interest to care what you think.

If you’re dating an entrepreneur, get ready for a dose of cold-hard reality. You’ll get the unfiltered opinions you should only hear from your mother. They’ll call you out when your sunglasses don’t fit your face or when they don’t like your article or when you don’t shave your legs. True stories.

Sometimes it’s tough to swallow, but there’s something to be said for taking the bad with the good.


If you’re dating an entrepreneur, get ready for a professional Evel Knievel.

Successful entrepreneurs display an adaptive form of risk taking and are biologically wired with a high threshold for novelty, stimulation, and ambiguity. Research indicates entrepreneurs are more inclined to make “hot decisions” that require tolerance for risk and discomfort.

This is great… sometimes. Stuck in the airport? They’ll turn a stressful situation into an adventure. Facing tough stuff? They don’t shy from hard problems or awkward conversations. Want to have fun? They’ll cook up dates, trips, and conversations that feed their own laborator retriever appetite for stimulation.

But there’s a caveat. When a relationship is new, you are the mountain to climb, the landscape to explore, the challenge to win over. You are the ambiguity and novelty that gets them excited. Find ways to keep it fresh, because when routine overtakes novelty, you might go out of style like the last idea that bored them.


If you’re dating an entrepreneur, you probably only see half the picture.

When you first meet an entrepreneur, you’ll likely assume they’re more successful, well-off, or connected than they actually are. This is because entrepreneurs are generally impeccable impression managersImpression management is a skill honed from years of fake it till you make it. And it’s not just “helpful to have,” it’s a damn near entrepreneurial requirement.

Toby Thomas, CEO of EnSite Solutions, says being an entrepreneur is like riding a lion: “People look at him and think, This guy’s really got it together! He’s brave! And the man riding the lion is thinking, How the hell did I get on a lion, and how do I keep from getting eaten?”

So if you’re intimidated by the apparent success of the entrepreneur you’re courting, find comfort in the idea that their enviable personal PR is a necessary magic trick. They’re probably just trying to keep from getting eaten by the lion, like everyone else.


If you’re dating an entrepreneur, you’re probably dating a crazy person.

Don’t worry, crazy exists on a spectrum. Psychologist John Gartner believes a condition called hypomania is responsible for the success of many great entrepreneurs.

While full blown mania causes delusions (you think you’re Jesus or the president or Beyonce), hypomanics fall just under this crazy cliff. You have the edge of inflated confidence, boundless energy, and a sincere belief you’re pretty f***ing awesome.

While 1/3 of small businesses fail within five years and 2/3 fail within ten years, a whopping 33% of entrepreneurs believe their company has a 100% chance of success. That requires some serious grandiosity. In addition to hypomania, Nobel Prize-winning psychologist Daniel Kahneman credits this to delusional optimism.

You’ll have to navigate around an hefty ego and hint of narcissism to date a successful entrepreneur. It just comes with the territory. So if you can’t deal with manic work binges and an occasional (or perpetual) big head, then get out now.


If you’re dating an entrepreneur, you’ll probably feel like you’re never working hard enough.

It doesn’t matter how ambitious you are, they’ll probably have you beat. According to David McClelland, entrepreneurs are driven by an overwhelming need for achievement. They’re builders, fixers, and get-sh**-done-ers. And they inextricably attach their identities to personal achievements, so they’re very motivated to get it right.

It can be be mystifying to an entrepreneur if other people aren’t driven by the same obsessive need for achievement. My girlfriend was recently broken up by her entrepreneurial boyfriend who was disturbed that her law career was a “good job” rather than something she was passionate about.

So if your achievement in life isn’t directly tied to work, find another pursuit that offers the sexy glint of passion and purpose. An entrepreneur wants to see that something revs your engine.


If you’re dating an entrepreneur, you’re going to have to compromise.

Most entrepreneurs start companies so they never have to play by someone else’s rules. According to multiple studies, entrepreneurs demand independence, reject authority, and don’t like being told what to do. Which isn’t always conducive to the whole “being in a relationship” thing.

They play boss for a living, so don’t expect ultimatums, threats, or demands to be well-received. As Richard Branson says, “I believe in benevolent dictatorship, provided I am the dictator.”

Entrepreneurs need partners who are strong, but also flexible, forgiving, nurturing, and similarly independent. If you try to cage your free bird, you’re going to get fired.

Entrepreneurs can make the best or worst partners depending on their mate.

So figure out if you’re cool with an open relationship between you, your partner, his company, and a few quirks, hangups, and ego drivers. If you’re up for the challenge, it’s worth it every damn time.

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