Entrepreneurship is embarrassing. I can't stress that enough. If you're just doing this for the clout or so that people think you're cool, this probably isn't the route you want to take. You're constantly putting yourself out there, things rarely go according to plan, and you constantly have to ask people to critique not only you, but your child (whoops, I mean startup)!

From the pitch competitions and the investor meetings to the constructive criticism from everyone--you tend to develop a tough skin. But every now and then, there are moments that catch you off guard and force you to re-examine who you are. This was one of those moments.

Titles Don't Pay the Bills 

After I graduated from college, I had the privilege to work on our company full-time. We had just been admitted into an accelerator with rent-free office space and we felt on top of the world. But this wasn't the large, six-figure investment deal that most accelerator programs dish out.

To say it humbly, our investment definitely couldn't cover our "living wages." So, while it was cool to capture the title of chairman and CEO right after graduation, titles don't pay the bills, and bills don't just disappear because you want to follow your dreams.

After Uber-driving my car out of commission, I had to get a job that was flexible enough to not take up my business hours, but consistent enough to yield a decent paycheck. I started looking for part-time work that would allow me to flex an employee discount for not only myself but the homies too.

Celebrate the Small Stuff

I found a job at my local gym as a janitor from 11 p.m. to 3 a.m. every night. It came with a free membership (and allowed me to bring a free guest, i.e., one of the homies). Besides making me tired all the time, it didn't interfere with our startup; it was perfect. I cleaned those toilets for months on end, as my manager told me I was one of the "best cleaners we've ever had" and "probably the first we've had with a college degree." I'm not being sarcastic when I say I took all those words to heart and proudly disinfected the showers. Sometimes you have to celebrate the small stuff.

In college, I participated in a variety of extracurricular activities, from theater and radio to Quidditch and some prominent internships, but my favorite activity of them all was being a teaching assistant. I got to work side-by-side with one of my favorite professors and hang out with my peers. The office hours, the tests, the papers--I loved it.

Fast-forward to me being the best cleaner my gym has ever seen; it didn't take long for one of my former students to walk into the gym. As this young man walked into the men's locker room, I saw his eyes go back and forth between my face and the in-use toilet plunger in my hand. In what seemed like slow motion, he said, "Oh my God, weren't you my TA?" Wearily I responded, "I sure was, man...and you better stay in school." I immediately speed-walked away.

As I made my best effort to run without bending my knees a million questions came to mind. Why was that the first thing I said?! Should I go back and actually talk? Did he see that toilet water splash on my shirt? As I sat in the janitorial closet, I started to think.

Not All Bad Moments Are Bad Moments 

More than anything, I was embarrassed that I was actually embarrassed. Embarrassed that I really had the nerve to think that this route would be a bit more glamorous. Embarrassed that for some reason I cared more about what someone thought of me than about the sacrifice necessary to make my dreams a reality. I was disappointed in myself. At that moment, a chord was truly struck inside me.

I thought that I defined the phrase "scrappy entrepreneur," but after that moment I took things to another level. I slept in more airports, confronted my bad decisions, and fully embraced the tedious parts of running a company on the rise. Dealing with the laborious head-on gave us more opportunities to do what we love, like talking directly with customers, executing marketing plans, or creating new partnerships to advance our user experience. I think that the sooner we as entrepreneurs come to realize that there will be specific aspects of running a startup that we won't like, the sooner we can come to terms with defeating them and getting to the parts that we enjoy.

I never expected this journey to be pretty, but I learned the hard way that if I am going to not only survive but thrive, I need to embrace just how dirty--pun intended--things can get.

How to Stay Motivated, Even in the Early, Most Difficult Stages of a Startup

Published on: Apr 19, 2018