The less-than-glamorous life of a young entrepreneur

By Hayden Williams , written on July 7, 2013

From The News Desk

This is the first in a PandoDaily weekly series that chronicles the experiences of a young entrepreneur as he bootstraps his startup. Come back next Sunday to read the 2nd installment. 

awake in the middle of the night to the sound of wood scraping against floor. I’m not in San Francisco, we don’t have earthquakes in New York City. I live west of any subway line, so that can’t be it. I lurch up in bed then hear a whisper.

“Hey. I pushed up the code, we should be good to go.”

It's my best friend and co-founder, Paul Osetinsky. We share a bunk bed and he’s just executed the requisite ladder climb and Indiana Jones-esque shoulderroll to squeeze in between the ceiling and the top bunk.

Why do we sleep in bunk beds? We don’t suffer from Peter Pan syndrome. We’re not afraid to grow up. You’ll find no lava lamps or beanbag chairs in our 10' by 12' room, and Paul only wears Michael Jordan cologne on Saturdays. But many things in our life do mirror the the student life we thought we'd left behind.

You've heard stories of the young entrepreneur who starts a company in his parent's garage, subsisting on ramen noodles while pouring his life into a product that eventually makes him a billionaire. Paul and I are that – minus the garage and product that has taken the world by storm. Yet.

We’ve known each other nine years, first meeting as freshmen at Vanderbilt. Last year we were working in finance jobs we didn’t love (a polite way of saying we hated them). We both wanted out, but didn’t want to blindly transition to another boring job. We wanted to talk to peers who had made career transitions, but found it difficult to find these people. Junior personnel aren’t prominently displayed on company websites and don't become the voices of their industry.

We decided there should be a networking equivalent to online dating sites, where people could go when they wanted to meet peers outside their network. So, we quit our jobs to build Treatings, a community of people open to talking about their work – over coffee.

The tipping point for me came during a slow day at work. I was hunched under my desk using my phone to watch an interview with an entrepreneur, because this type of “propaganda” was blocked on our work computers. In the video, the entrepreneur said something to the effect of, "You can’t read a book on skiing. You have to get out there, and if you aren’t falling you aren’t learning." I realized I had never truly fallen, at least not in my professional life. I figured it was time to break out of my comfortable gig and add some wipeouts on my resume.

Now that we’ve been bootstrapping Treatings for over a year, I can say I definitely got what I asked for. To cut back on rent, Paul and I moved into a three bedroom apartment with two friends and share the smallest room. There’s nothing comfortable about being 6’3 and sleeping in a bunk bed. It's also no fun asking an employee at Bed Bath & Beyond where  the twin XL sheets are and her saying “I don’t think you are looking for twin XL. Those are only for dorm room beds.” The only income I’ve had in the last year is a jury duty check for $120.

For “office space,” we leveraged an old apartment address to get “Friends of the Library” passes at New York University's Bobst Library. These passes are normally reserved for donors whose names are plastered on school buildings. We spend so much time in the library that when Paul or I walk past security without the other, the guard will inquire about the wellbeing of the other.

Of course bunk-bed sleeping, library-working entrepreneurs need a way to get around, so we picked up bikes. Then came backpacks, which at this point our friends wouldn’t recognize us without. For better or for worse, we have essentially merged ourselves with Treatings. Our morale tracks the highs and lows that come with building a company. It has consumed the last year of our lives and much of our savings.

There is no bookend to put on our story because it’s very much evolving. The best case would be for Treatings to become the first place professionals turn when they want to learn about companies or skills but don't know anyone with relevant experience. Companies would then rely on the platform to engage with passive job candidates. The worst case scenario? It fails, potentially because of the inherent friction of two strangers meeting in person or a hesitancy to reach out to strangers. Then I'll have to figure out what to do next.

Nevertheless, I wouldn't trade this experience for anything. I've developed a resiliency that makes it easier to get up and dust myself off every time I fail – and that happens a lot. Am I glad I quit my job to build Treatings? Yes. Was it a good decision? To be determined. The things I’m surrounded by every day – the bunk bed, the library, the dwindling savings account – are a constant reminder of how transient my lifestyle is.

We’re seeking to bootstrap Treatings as long as we can, but our runway isn’t endless. I just hope we hit an inflection point before it’s my turn to take over the top bunk.

Image: Flickr