Starting a company and having a girlfriend isn't easy

By Hayden Williams , written on July 21, 2013

From The News Desk

This is the third in a PandoDaily weekly series that chronicles the experiences of a young entrepreneur as he bootstraps his startup. Read Part 1, ”The less-than-glamorous life of a young entrepreneur,” and Part 2, “How to survive co-founding a company with a friend,” and come back next Sunday to read the next installment.

“This bed isn’t going to fit, buddy,” the exasperated mover said.

This wasn’t a feng shui crisis of how to properly position the bed to maximize ch’i. It was a game of inches. There was already one queen bed in this small, windowless room -- the kind only coveted by cash-strapped young people in New York City. We just had to squeeze in one more.

I was sweating. It could have been because I’d spent the whole day moving apartments or the fact that I was in danger of being late for Valentine’s Day dinner with my girlfriend, Claire.

It was bad enough that I was moving on Valentine’s Day. What made it worse is that I was moving into a studio with someone other than my girlfriend. My friend/future co-founder Paul and I had quit our well-paying finance jobs to start Treatings, an online to offline networking platform that lets you get career advice from strangers over coffee. We put our two-bedroom apartment on Craigslist to see if we could get out of our two-year lease and find a cheaper option. When someone snapped it up on the condition that he move in immediately, we scrambled to find an available studio.

So there I stood, on February 14, 2012, alone with the movers as Paul hadn’t given notice at his job and had to run back to the office. The movers were shaking their heads, finding sadistic humor in the situation, sure that the second bed wouldn’t fit. I nervously looked back and forth between my watch and the bed outside the apartment, knowing I should have left five minutes earlier to make it to dinner on time.

My phone vibrated. “Hey, just got out of work. Heading to the restaurant, see you soon!” read the text from Claire.

Siren went off in my head. It was go-time.

“There’s no time for backup,” I announced, as if auditioning to be Denzel Washington’s wacky sidekick in a bad buddy cop film.

I wrestled the mattress out of the mover’s hands, dragged it into the room, propped it up, then dropped a poorly executed cannonball on the mattress to wedge it between the wall and other bed. I ushered the movers out of the apartment, dug some wrinkled clothes out of a cardboard box and ran out the door.

Despite these heroics, I still arrived to dinner late. As you can imagine, apologizing to Claire for my lateness by explaining how hard it was to get my queen bed squeezed next to Paul’s didn’t set a romantic mood.

I’m happy to report, as I knock on wood, that our relationship survived. Arriving late to a Valentine’s Day dinner date is, of course, a first-world relationship problem. It’s one of many Claire’s gotten used to -- the “while my friends are getting taken out on nice dates, my boyfriend found a bar with an extended happy hour where you can order discounted Seamless” type problems.

I know, call me Romeo.

But these superficial problems are trivial compared to some of the other baggage that comes with dating a first-time entrepreneur trying to figure out what the hell he’s doing.

Like many founders and employees at startups, my week is dominated by work. This leaves little time to see Claire, or anyone besides Paul for that matter. Certainly no one is forcing us to work at any pace, but we’re susceptible to the fear that if at least one of us isn’t pushing the product forward, it will fall backwards.

What I lost sight of while throwing myself into Treatings is that relationships are no less fragile than startups. Since we are in our startup’s early stages, we can’t just sit back and hope the community builds itself. A lot of manual work goes into recommending individuals for our members to reach out and meet for coffee. Similarly, I can’t expect Claire and my relationship to flourish, or even exist, without nurturing it.

“Going to happy hour on Friday doesn’t make up for not seeing each other at all during the week,” Claire said after another stretch of three or four weekdays when we exchanged little more than a few gchat messages.

“I know, I’m sorry. But this is only temporary” was my half-hearted response.

She called bullshit. We both knew that (hopefully) certain bunk-bed aspects of my entrepreneurial bootstrapping life are transitory, such as the bunk bed my roommate/cofounder traded in our queens bed for, but any amount of success Treatings has will only ramp up the pressures. Better to deal with it now.

I try to walk the line between mapping out time for us to spend together without making it feel regimented. Friday happy hour and dinner, Saturday venture outside Manhattan, Sunday explore inside Manhattan, that sort of thing. The goal is consistency without losing all form of spontaneity. What makes it especially tricky is that I also like to see my friends on the weekends. They’ve never been accused of planning ahead of time, so it can be difficult when Claire and I are heading to dinner and I get a “Dude, we’re nailing a hot sauce festival in Brooklyn, can you be there in 30?” text.

But since I also worked long, varied hours in investment banking, the amount of time we spend together isn’t the biggest change since starting Treatings. Rather, it’s the fact that now my mind is often preoccupied with startup fever.

So-called work-life balance gurus preach, “Don’t take your work home with you.” In my last job, walking out of the office, getting into the subway and getting out of my suit as fast as I could was an effective disconnecting routine. But when you don’t have an office, work anywhere with wireless Internet, and “home” is the room you share with your co-founder, it’s harder to disengage.

“Should we switch ‘networking’ to ‘informational meetings’ on the landing page?” is not the first thing Claire wants to hear out of my mouth when I haven’t seen her in days. Especially when the week before I was asking the reverse question.

“You have to stop talking about Treatings all the time. Not for my sake, because I like hearing about it and helping, but for your sake,” was one memorable response.

She was right, of course. For a long time after starting out, I was oblivious to the fact that I was injecting Treatings into almost every conversation we had.

While it can be lonely being an entrepreneur, I think it can be even more lonely being in a relationship with an entrepreneur. I’m lucky to be building a company with a long-time friend who can relate to the ups and downs of startup life. Claire doesn’t have a reference point or support network of friends who are dating crazy excited/scared (depending on the hour), obsessive and cheap guys whose demeanor are wrapped up in a nascent company that could fail tomorrow.

In the end, I think there’s a healthy amount of fear in any romantic relationship. The second you think it’s self-sustaining is the second it could blow up in your face. Complacency can kill relationships just as fast as it can kill startups.

I was able to write about my relationship with my co-founder, and a week later I still haven’t lost him. I’m hoping for the same outcome with my girlfriend, but will she come to her senses and head for the hills?

Check back next week!