Should Entrepreneurs Date Other Entrepreneurs?

Fourteen entrepreneurs candidly explain whether or not entrepreneurs looking for the "one" should start by browsing the local startup scene.

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There comes a day when you start looking … for a new office, a new business opportunity and a plus one. Some people say you are who you date, while others prescribe to a mental list of the best traits to look for in a mate. But do entrepreneurs have it any easier — or harder — when it comes to love?

Do founders make the perfect match? Fourteen entrepreneurs candidly explain whether or not entrepreneurs looking for the “one” should start by browsing the local startup scene.


1. No! It’s hard to manage a relationship with two different, and ultimate, goals …

“An entrepreneurial venture takes almost 100% of your time and to have someone else who is also devoting 100% to a different business would be impossible to manage and develop a relationship. On the other hand, if they had a complementary business where they could support each other while enhancing the individuals businesses, it may work as they have the time to spend together. I have created many businesses and my fiancé has as well. Currently we work together on one as a joint venture and I don’t see it working any other way. I would feel jealous of her time spent with any other business as well as miss the support of my own business if we had separate companies. I believe it best to find someone who has a venture you can support or find someone to support your venture.”

– Christopher Nelson, CFO at Glass Handbag, @glasshandbags


2. Yes! Definitely! Heck Yes! They will motivate each other to get more time and money.

“The reality is that being an entrepreneur is time consuming, and not necessarily from the ‘hours’ of work they put into their company. It’s the mental game that always takes precedence. Even after logging a 50 hour work week, entrepreneurs go home with the worries of their business over their heads. On a good day, they rejoice in their success. On a bad day, they are constantly putting out fires and fighting discouraging thoughts: Will we survive? Do I have to fire that person? Can I make payroll? For someone who has a different career, perhaps working for someone else, when they leave work, they ‘leave’ work. When dating or marrying someone who does not run their own business, entrepreneurs risk running into the I-dont-have-enough-time-for-you syndrome, not because they do it on purpose, but their company is of equal or (sadly at times) more value to them then time spent with their partner. Entrepreneurs understand that of each other, but 9-5ers often don’t, at least in my experience.”

– Renee Warren, Co-founder and CEO at Onboardly Media, @Onboardly


3. No. There may be lots of competition regarding who is doing better.

“As an entrepreneur, I believe in a ‘balanced’ life and to make your startup work, your life has to be somewhat imbalanced. Both [entrepreneurs] are trying to achieve big dreams. Both are alphas, [so] there may be lots of competition regarding who is doing better, or some insecurity complex (if one makes more than the other). While both people understand each other, they are imbalancing their lives typically with work [being more important than the] relationship. If one [person] is an entrepreneur and the other is not, it is easier to balance since the entrepreneur can take some time off to balance with the non-entrepreneur.”

– Albert Ko, Co-founder at DealGuppy.com


4. Yes. I’m in a relationship with another entrepreneur and it’s great.

“Owning a company is a very unique situation when it comes to time and money, so it’s nice to have a partner who doesn’t need me to explain why I sometimes work Saturdays or can take off with me mid-week should we both need a break.”

– David Hooper, Founder at Music Marketing [dot] com, @davidhooper


5. Yes, and I speak from personal experience.

“By dating another entrepreneur, they’re more understanding about your struggles and triumphs, they have great business advice, they have schedule flexibility and are also more understanding about roadblocks you may encounter and can offer encouraging words of support that all entrepreneurs need to hear to keep going.”

– Kendra Newton, Founder and CEO at Hot Property PR, @hotpropertypr


6. Yes, absolutely! Entrepreneurs are a species of our own.

“It helps to partner with someone who has the same sort of drive as you. If you don’t, and there is a mismatch of values, it’s probably not going to work. My husband and I became entrepreneurs together when we started our business, and I couldn’t imagine it any other way. I am so grateful that my husband and I share the same passion and zest for life and are able to carry that out in our work life as well. In addition to our venture together, we each pursue other entrepreneurship avenues separately. [He] is a personal trainer and I am a public speaker and writer. Entrepreneurs are a different kind of breed … it takes one to know one. For an entrepreneur to be happy in a relationship, they have to find a person who’s thirst for life matches their own.”

– Kelli Koehler, CEO at Wildway, LLC, @kellikoehler


7. No. A few months ago I called off my wedding to a Silicon Valley startup engineer.

“We were supposed to be married last month. I founded a design firm, started an event listing website, and joined a YC startup and was balancing these three projects at the same time. Then when my boyfriend proposed, I added wedding planning to that list. My fiancé was working, more than full-time, with a startup — recently acquired by Facebook. Between both of our busy schedules, I rarely saw my fiancé even though we lived together. One of us would leave for work before the other got up, or be sleeping before the other got home. I forgot who he was, what he was like to talk to and hangout with, and wedding planning fell to the wayside. I am very passionate about what I do and tend to get very focused on my work. My fiancé was the same way. While this is a helpful trait to have as an entrepreneur, it makes maintaing healthy relationships a challenge. Entrepreneurs are usually busy focusing on making things ‘bigger’ than themselves, which makes personal matters seem so ‘small’ in comparison.”

– Jessica Greenwalt, Founder and Principal at Pixelkeet, @pixelkeet

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