How to Date an Entrepreneur

By Caroline Leung on
How to Date an Entrepreneur

Entrepreneurs aren’t an alien species. They’re not Jekyll with you, and Hyde with their business. Entrepreneur is just another title, like lawyer, doctor, or chef. We’d be remiss, however, to disregard the oddities entrepreneurial life can bring to a romantic relationship.

As natural disruptors of the mediocre, entrepreneurs have a knack for illuminating variables that are just “good enough,” and turning those variables into something extraordinary. They’re bound to offer the same level of energy and intensity to you, their loving partner.

With an entrepreneur by your side, you’ll be coaxed out of your comfort zone, exposed to an unorthodox work-life schedule, and encouraged to partake in thrilling, sometimes even unusual experiences. But the entrepreneurial way of being also has a dark side. In pursuit of greatness, obsession, anxiety, narcissism, and impatience can manifest. If you don’t view the world through an entrepreneur’s lens, this behavior can be challenging to endure.

Consider this guide a compass for a healthy relationship for any non-entrepreneur/entrepreneur couple currently navigating their share of differences, be it in personality, interests, or—indeed—work.

Remember: Two Mindsets are Better Than One

When founder of the Vinetta Project Vanessa Dawson met her partner, Grant, it was a classic case of opposites attract. Where Grant was calm, Vanessa was spontaneous.

“He’s got this grounding kind of affect on our relationship,” she explains. “[Though] I was into the concept of a power couple—where you’re both doing the entrepreneurial thing hardcore and working at your company—it’s really nice to have this balance where he is my rock. He is a source of stability when I’m all over the map, literally and mentally.”

Whether you’re the dreamer to their pragmatist, or the big-picture thinker to their eye for detail, during moments where your differences give rise to frustration, it can help to remember that contrast provides balance and attraction, even if you don’t fully understand where they’re coming from, or why they’re being so pedantic.


‘I have an idea.’ My wife is sick of hearing that one... She knows I’ll spend several days, weeks, or months talking about it.
— Chris Ronzio, Entrepreneur

Understand That Work Will Come First at Times

According to Inc. 500 entrepreneur Kevin Daum, “entrepreneurs are benevolent narcissists.” He says that while an entrepreneur’s desire to realize their vision almost always comes from an innate desire to make the world a better place, it can lead entrepreneurs to obsess, overwork, and talk ad nauseum about what they’re working on.

If you don’t share a similar level of intensity for your profession, it can be hard to support the behavior in someone else, especially on the occasions when your partner’s work takes precedence over your relationship.

Isabelle Thye discovered a remedy to this scenario during her relationship with an entrepreneur: invest time spent apart on your own interests and passions. “You need to be comfortable being with yourself, developing your own passion, honing your skills and navigating your way toward your goals,” she writes.

Communicate your expectations around spending time together, and re-frame the instances when your partner is working as ‘quality alone time’ rather than as ‘neglect’. Scheduling time together on a routine basis, well away from work distractions, can also offset those instances when your partner is pulling an all-nighter at the business.


There’s a not a lot of talk about the emotional rollercoaster—what you’re really going through.
— Vanessa Dawson, Founder of The Vinetta Project

Believe in Them During Times of Self-Doubt

As entrepreneurs are often the embodiment of their business, a setback can deliver a disproportionately severe sting. If the business fails, or if cash flow dips, it isn’t just their time, money, or health on the line—it’s their name, reputation, core beliefs, and values, too.

Vanessa is quick to point out that she’s experienced this firsthand as an entrepreneur. 

“There’s a lot of focus on the success and glory of being an entrepreneur, but there’s not a lot of talk about the struggles and ups and downs and emotional rollercoaster—what you’re really going through,” she says.

“Society glorifies the entrepreneurial lifestyle because you see all the wins and successes. But we really need to talk more about the mindset and mentality that you need in order to be an entrepreneur, and supporting that mentality both consciously and subconsciously.”

Thankfully, when Vanessa is going through stressful times, Grant is there to quell her self-doubt, reminding her that she's doing the right thing despite impeding factors beyond her control. “It’s one of the things I really like about her, that drew me to her—this passion for building this business and bringing some change into the culture of business in our society," he says. "She’s made a big impact on a lot of people already, no matter what happens.”

As a non-entrepreneur, with the privilege of an outside perspective, you can remind your significant entrepreneurial other why their vision was worth it in the first place. Having faith during those times when your partner’s is faltering can bring them back from the brink of an emotional setback, and help keep your relationship on track.


Entrepreneurship is absolutely impossible without help, love, and support.
— Stacey Alcorn, Author and Entrepreneur

Know that Your Presence is Invaluable

Possibly the most daunting aspect of the entrepreneurial journey is the need to keep up appearances. From enlightening friends who are curious about how the business is doing, to reassuring family members who may be worried about the risks taken, to maintaining a game face for stakeholders... it can be a lonely life. Often, a romantic relationship is the one place where entrepreneurs can be completely vulnerable and at ease.

Casey Ames, who owns and operates his website management platform Base Enterprises, considers the support of his girlfriend, Amelia, to be invaluable: “[We] make life decisions together. That's something I don't have to do with friends, family, or other entrepreneurs. If they don't support me, that's okay because I can continue on. If Amelia were to stop supporting me, then it would end up affecting my whole lifestyle and the decisions I make.”

The influence of your presence is untold, even if that’s not always explicitly communicated by your partner.


We have a sense of freedom we’ve never even imagined before. We’re living the life we’ve always wanted. And, now that you’re a part of our life, we want to share that freedom with you.
— David Hrostoski, Entrepreneur

Leverage the Unorthodox Nature of Your Relationship

When Joe Bauer founded his own online nutrition coaching platform All Around Joe, the flexibility of his location-independent business allowed for him and his girlfriend, Emily, to explore their love of adventure.

“Having the ability to spend quality time together whenever we want, free of the constraints of a ‘normal’ nine-to-five career has allowed us to pursue the things we love most,” Emily explains. The pair plan to spend next year traveling, living, and working remotely out of a van.

Similarly, before he met his entrepreneurial partner Vanessa, Grant remembers feeling bored and restless with his life. “I was living in the same place, [with] the same habits for four years. My job was very stable and repetitive,” he says. “Those four years are pretty similar. They all blur together for me. When Vanessa came along, it inspired me. She was like, ‘I have an idea, let’s get some change into our lives,’ it was exactly what I needed."

Grant has since relocated from New York to Los Angeles, both to live with Vanessa, and to work as a gaming developer. He acknowledges that Vanessa’s entrepreneurial spontaneity played a large part in inspiring him to make the move.

Although the lifestyles and work schedules of entrepreneurs can be unpredictable, they also tend to be more flexible than the schedules dictated by full-time employment. In addition, entrepreneurs tend to embrace risk. So make sure you have fun with these traits in your partner.

Who says date night has to be on a Friday? And is there really anything stopping you from relocating to a new city, or taking a sabbatical together? Leverage the unorthodox nature of your relationship, and you may come up with new ways to enjoy your time together that fall well outside of mainstream thinking.


The belief that romantic relationships are all bliss and no work is a common misconception.

Every coupling requires individuals to navigate their partner’s quirks and idiosyncrasies as they journey deeper into the relationship. Anyone who’s made it past the honeymoon phase would agree that helping a relationship succeed calls for grit, patience, and determination.

Although the mindset gap between non-entrepreneurs and their entrepreneurial other halves may be wider than most, the magnitude of your differences could be the very thing that helps your pairing become the most interesting, diverse, and adventurous relationship of your life.

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