Dating an Entrepreneur: Chaos & Coffee Dates

The other day I suggested to my boyfriend that we embark on a joint blog together where we would cover the craziness we are going through as two entrepreneurial types, working for startups and falling in love.

To be honest he really loved the idea. We joked about the pictures we could snap of late night brainstorms (aka our hot dates) at his office, our conference travels together (aka our pretend vacations), etc. We were super excited until we realized that the blog would likely become a public forum where we would both vocalize just how much this chaos freaks us out at times. We agreed against the blog (for now) but I still thought a post was worth embarking on.

Love is crazy. Like seriously crazy. There are all sorts of things that you don’t expect – compromise for one. Compassion for another. Sacrifice of course. Then there is self-discovery and confusion. There are inevitably moments of doubt. There is also (hopefully) laughter, and silliness. All of this for a common goal – to make it last. The two of you want to build something together that is greater than each of you.

Funny enough… a startup is all those things and more.  Read the paragraph again but think about a start up – compromise, sacrifice, doubt, laughter, silliness—and all for a common goal of building something bigger than yourself.

My boyfriend is a Partner and CMO of a Seattle-based start-up. You can go check him out here. He is a brilliant marketer and businessman. He is a knowledge-seeker, an information consumer, and (I believe) he is one of the biggest “thinkers” I’ve ever met.

He is also my boyfriend. I’ve dated for the last decade in hopes of finding a man like him. He is a Texas cowboy at heart, a family man, a singer, an artist, a film nut, a photography junkie. He is sarcastic yet respectful. He is gorgeous. Dimplessss for days.

We’ve been together a year and a half now. Which for me is quite some time. While things are fantastic at the core, we both admit that as our start-ups grow, our love feels the growing pains.

I’m not saying we have it harder than other couples, but I certainly do think some of our challenges are unique. Lets cover a few of the things that keep us cracking up (half seriously and half awkwardly) as we maneuver this challenge:

First off. We aren’t first. We can’t be. Ask any entrepreneur and they will tell you when all is said and done there are ties in the priority tree. There has to be. While we promise to be there for each other whenever we need each other, more than not we give each other passes on not being there when we need each other. Maybe we are out of state, maybe our sites went down, maybe it’s a trip to the valley that has us occupied. Whatever the reason…we both agree that –right now—for us there are ties for who is first. For me it’s him and my work. For him it’s me and his.

Secondly, our start-up worlds connect. Our industries (although separate) connect. We’ve spoken at three of the same conferences at this point. We have been invited to the same meetings, and the same events…separately. We have similar business friends, and super-connectors between us. This can certainly be an advantage…we can leverage knowledge, experience, trust. It can also be a scary fucking thing. What if we don’t make it? What then? How the hell does that break up work? Human nature reminds us we can only control so much and those unknowns are scary when so much overlaps.

Lastly, we’re freaking moving fast…like whoa hustle, crazy, bam, moving fast.  This is the start-up way. You all know what I mean. This week isn’t ever just “a week.” It’s the week, before the month, of the big thing that has to happen, before we talk to investors, before we can get the money, to reinvent the (fill in blank) so we can help the world…do what they love and we love…better. Phew.

When life moves so fast, it’s easy to forget how wonderful the people next to you are. All of a sudden you look to your right and either you left them behind or they jumped ship a few “sorry I couldn’t make it” or “I’m just too busy” excuses ago.

Those are just a few of the crazy things we deal with daily but maybe you get where I am going. Him and I, for the most part, talk about how lucky we are. We both love our companies. We both love this fast-paced industry. We both love the days we get to live.

But sometimes… occasionally… we look around at people sitting in cafes all day playing Battleship, instead of on their computers, and we daydream of what a life like this is like. What does love look like for them?

Funny enough, the second I start thinking about that… I realize it is so NOT us. We tried to take a vacation last year and after a few days of laying out in the sun we were seriously stress balls. We never fought so much as we did when we tried to slow down. We just aren’t those people, at least not now.

Right now we are the couple that meets up mid-day to brainstorm over coffee. We sneak a kiss or two, and we exchange what hour we think our days will end. It works for us right now, with a little shaky here and a little shaky there. I think that’s pretty common though.

For others it’s late night TV time that brings you together, for my parents it was the morning time when us kids were still asleep and for him and I – its two iced americanos and some big ideas.  Like I said, we are pretty lucky.

Whenever I start to think about how crazy it is that us two workaholic, start-up junkies fell in love at this point in our lives, I can’t help but think…it wouldn’t have worked any other way. It all comes down to one really important thing — he gets my crazy. And I get his. What more could two people ask for?