Startups Are a Workaholic's Paradise

Like falling in love, initially everything was pretty fun and exciting. And then things started getting serious.
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A few years after The Social Network, startups are still seen in an overly romanticized light, when they're actually just a waking nightmare for most people.

But for those of us addicted to work and challenges and depressed by 9 to 5 monotony -- startups are way more romantic and life-changing than even Aaron Sorkin makes them out to be.

I'm still in the honeymoon stage, so let me give the other side:

I drank The Social Network Kool-Aid.

It took me two years -- but after being bitten by The Social Network bug, I set out to change the way people date, and started the Dating Ring. Deflated about a relationship that hadn't worked out, and not feeling challenged enough by the lifestyle company I had been running for four years, I emailed a developer friend of mine from college and asked her to drop everything and be the CTO. Within a week, she agreed.

Since then, we have been working on the company 24/7. I started out going to bars almost every night of the week with prospective Dating Ring members, giddily telling them about my idea, and asking them to join and refer their friends. I'd then return home and would stay up until 3 or 4 a.m. on calls with my CTO, trying to figure out if our product would be free or if we'd charge, how we'd get customers, how we'd go big. During the days I tutored students over Skype to support myself, while organizing Excel spreadsheets with email addresses and writing newsletters about my cat and Gilmore Girls, and how we were out to change the world.

Like falling in love, initially everything was pretty fun and exciting. And then things started getting serious.

As you've heard a million times before, starting a company is like getting married.

Just as you shouldn't get married just to "be married," so too should you never ever start a company just to "have a company."

When you get married because you are in love and compatible with the person and have really solidly aligned values and agreements about money and kids and who takes out the trash on Tuesdays -- it's pretty damn great, or so I've heard.

And when you start a company because you are just so damn passionate about the idea that you can't not do it, and you find business partners who you're long-term compatible with, and you have aligned values and agreements about money and long-term goals and hires (a.k.a. -- kids) -- it's pretty damn great.

Don't be drawn in -- or scared off by -- the shiny moments.

In September, I found myself onstage giving an impromptu pitch to my startup idol, Alexis Ohanian, in front of 1,000 people. Two weeks later, I had a panelist tell me in front of over 200 influential people in the tech world that he wanted to shit on my company, and that it would never work or get funded. A month later, the Dating Ring was featured in the New York Times, and a week later, it was accepted into Y Combinator's winter 2014 class.

These are the stories that everyone hears and knows about, that get the Facebook likes, that lead to crazy highs and lows. But those highs and lows fade quickly; it's the day to day interactions with customers and spreadsheets and numbers that drive the long-term satisfaction.

If you're encouraged to enter the startup world by the trophy moments -- or discouraged from entering due to the discouraging ones -- then it's probably not the world for you.

The magic is in the little challenges and triumphs.

The real romanticism in the startup life -- for those crazy people like me who enjoy this kind of work -- is in the day to day. After getting accepted into Y Combinator, my cofounders and I dropped everything and moved out to a sunny house in Mountain View with a big kitchen and an office. YC has given us thtree months to forget about pitching or investors or living expenses, when we instead get to focus on building the best product and user experience we can build. After bootstrapping with no salary and no end in sight for almost a year, I wake up every day thinking "Is this real life?"

Right now, I'm a customer service rep, matchmaker, vice product officer, CFO, COO and CEO. I'm doing six jobs combined into one, working 100 plus hour weeks and through the holidays, and I've never been happier.

There are a thousand and one things I can choose to focus on every day, from trying to figure out how to balance Paypal transactions in Quickbooks when I can't import the ".iff file" in the online version (help, anyone?) to reading the juicy feedback members give after their dates, to blogging about gender and tech, to planning big parties, to measuring how well two Facebook ads with different pictures of my friends are performing.

And even though I work almost every waking hour, I have the freedom at 2 p.m. to turn on an episode of Parenthood and have a good cry, or take a five mile run in 65 degree December weather (okay, now this may just be a lifelong north-easterner who's a bit googly eyed about living in California for the first time...)

Say goodbye to your social life.

The irony is, of course, that I started a dating company because I'm a huge romantic that values personal connections -- with family, friends and significant others -- above all else. And yet, starting a dating company leaves me with no time for anything except work. This will probably be the case for the next few years as my cofounders and I work our hardest to make this company sustainable.

I've given up a social life; I've said goodbye to N.Y.C. and my close friends; my "raucous" 20s are on hold; and -- hardest of all -- I've had to leave my beloved obese and tailless cat with my parents for a few months.

This workaholic has found her paradise.

But, this early on in my career, that sacrifice is well worth it. Considering work takes up a good part of your waking hours regardless of what you do, I just can't imagine what it would be like to wake up every day not excited to go to work.

Regardless of what happens with the Dating Ring, I know I'm not going to regret the time and effort I've put in. I've learned more in the past nine months than the past few years of my life combined; I've gotten to meet hundreds of people and I've felt like I am putting every ounce of myself into something I love.

At the end of the day, working 24/7 with no social life is hell for the majority of people. But then again, working 40 hour weeks at a desk with no autonomy is hell for the rest of us.

Startups are no easy way out. But they can be every bit as magical as they seem for those of us who enjoy impossible seeming challenges and will do anything to escape boredom and monotony.

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