The guide to dating an Entrepreneur
The startup journey is a lonely one. No one thinks like you do, sees your vision, or understands why you're working twice as much for half the pay. Tasks and errands that are deemed normal to most, like cooking at home or doing laundry, become luxuries that you simply don't have time for. Encompassed in the list of "things I wish I had time for:" is dating.
Entrepreneurship has become very sexy over the last decade. With shows like Shark Tank and the movie Social Network, entrepreneurs are becoming pop culture icons overnight like athletes and musicians. Names like Cuban and Musk are as household as Jordan and Spears. As a result, it is not surprising to see people fall in love with the idea of being an entrepreneur as well as dating one. All that glitters is not gold, though; just as it is not easy starting a business, being with someone who has decided to pursue an entrepreneurial lifestyle can be very taxing. If you are considering dating an entrepreneur, here are a couple things you should know before you start envisioning your future as the next Mrs. Zuckerberg or Mr. Winfrey (s.o. to my female entrepreneurs):
You are not going to change them.
Like a sweet girl going after the bad boy, people tend to meet a single entrepreneur engulfed in their business and think they can change their ways. If your idea of a perfect relationship involves having dinner every night after work and having your spouse all to yourself on the weekend, it's best to stay away. You cannot expect a status quo relationship from an entrepreneur--the whole reason why they are entrepreneurs are because they not content with the status quo. Their life is more than likely going to be hectic, and until their business becomes fairly sustainable, that will not change. Clarity is key to any strong relationship, so I recommend having a conversation about expectations early on.
On every first date I go on, I always have a conversation with the girl regarding my lifestyle. I let her know that there will be times I won't be able to talk to her for hours, how I may get a phone call in the middle of a date that will require me to rush back to my business to put out a fire, and that at times it will feel like I'm constantly choosing my business over them. I do this in an effort to hear her feedback and align our expectations, so that we both know what we're getting ourselves into. If you are still interested after you have a conversation like that, go for it. If you think you can just play along right now and fix them later once you're deeper in the relationship, let me know how that works out.
Think Value
Kate and Andy Spade with one of the first Kate Spade bags
If there's one thing an entrepreneur can appreciate, it's a solid value proposition. Rather than focusing on what you think your best traits are, learn what they value most about you. If they enjoy your sense of humor, send a funny snap here and there; if you are both big into cycling, get a morning ride in before their day starts. Conventional dates do not have to be the only way you develop value in their eyes. Time will not always be on your side. More often than not, you'll be finding yourself planning a date a week out in advance, only to reschedule two more times before actually following through. A bond laced with multiple layers of value, however, is a choice adhesive for a lasting relationship.
Stay Flexible
Uncertainty is one of the biggest deterrents when people consider becoming an entrepreneur. For me, that is part of the fun, but there are times where that does get in the way of spending time with others. If you are dating an entrepreneur, be prepared to adapt and call audibles on the fly. You may see each other daily one week and then only once for a quick lunch date the next. It may bother you because it will seem as though they are constantly choosing their business over you. I understand that feeling, but before you drop an ultimatum between you and the business, I'd like to provide an analogy from an entrepreneur's perspective.
Vlogger Casey Neistat and his wife Candice Pool
A startup is like a newborn baby to an entrepreneur--it requires them to nurture and care for it constantly. Just as it is difficult for a mother to leave her newborn with a babysitter, so is it with an entrepreneur leaving their business in the hands of a manager or employee. So when you give an entrepreneur an ultimatum of choosing either staying with you or tending to their business, it is as if you are asking them to choose between you and their baby.
Rather than keeping score of the number of times they chose the business over you, look for intimations that demonstrates that they sincerely value your time. One way I show someone that their time is valued is by offering a resolution when I can't make it out or have to cut a night short. I'm sorry, something came up so I can't do Thursday anymore. I really want to see you, though. Friday for dinner? A sincere apology and offer for an alternative solution really goes a long way in relationships, especially when it comes to dating. As long as you feel your time is still valued, observe a little patience and stay flexible.
Be Passionate
The driving force for an entrepreneur persistence is not fame or fortune--it's passion. It's a trait that is apparent in every successful entrepreneur and every successful relationship. The most common remark I hear from people who are dating an entrepreneur is that seeing their significant other's passion motivated them to discover their own. I believe you should always pursue your dream, no matter how lofty it may be. If being judged is a reason why you are hesitant to move forward, then there is no better time to pursue it than while dating an entrepreneur. Their goals will be as--if not more--farfetched than yours. Rather than hearing,"why would you do that?" you'll more than likely be asked,"why aren't you pursuing it already?" The entrepreneurial spirit has a magical power of pushing boundaries and turning impossible to possible. Use it to ignite your passion and to keep theirs kindling when times get tough for them.
Is it worth it?
Dating an entrepreneur is not as glamorous as it may appear. There will be ups, downs, and inbetweens. Inevitably, you will become a pro bono employee of their business; date night some weeks may shift from dinner and a movie to packing and fulfilling orders. And there's going to come a point where you ask yourself is it worth it? Well, there's a saying I once heard, it takes years of personal sacrifices to look like an overnight success to others, which I think is pretty applicable to relationships. One of the greatest aspects of dating, as well as starting a company, is sharing life long memories together. It's the struggles, the unpredictable moments, the war stories that are worth reminiscing on. The road is tougher than most, the journey will be more attrite than expected, but the reward is supreme. If you're into an entrepreneur, but are worried about making the leap remember this: it is much easier to jump off a cliff when someone is holding your hand along the way. Make the jump and get your power couple on.
MMA superstar Conor Mcgregor and his wife Dee Devlin
