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All the Bad Things Make the Entrepreneur

Kenny L.
Kenny L.
Oct 11, 2020 · 6 min read

I remember, years ago, walking through the San Antonio office of one of the world’s largest oil companies. I was staring at an ocean of cubicles. Many of them stretched from floor to ceiling. A few of them stopped at hip height. “We’re trying an open concept on this floor,” the secretary said, as he guided me to the meeting room to meet with my clients.

“No one likes it, though,” he whispered with a smirk.

As an entrepreneur straight out of college, it was my first experience in a large corporate setting, and it was just as I had imagined. At that moment, I also remember asking myself, for the first time, if I could imagine myself working in a cubicle. The idea was foreign to me. Don’t get me wrong — the office was nice. But it wasn’t the office I knew, which started in a kitchen.

Most entrepreneurs would probably agree that building a startup changes your perspective on life and everything happening around you. Some events may seem bad in the short term. Over time, they transform into experiences that mold entrepreneurs into resilient and sometimes misunderstood humans.

A New Normal

During the first several months of starting my company, I had no idea how to fundraise, let alone run a company. As a result, money was scarce as my cofounders, and I hustled to build a product and get our first clients. The first few months were very tough. I was living with six other people in a house that had one bathroom. To get by financially, one of the things I’d do was go to this sketchy, unmarked building off the side of the freeway in Boston once every six weeks to sell my blood. Because it was for research purposes, the center would give me $50 in cash every time I visited, instead of cookies that you’d normally get if you donated blood to places like the Red Cross. I would’ve gone more often, but six weeks was the minimum amount required in between each visit. I learned this by trying to go again the next day after the first visit.

I remember my first visit — I was nervous. Walking through the unmarked doors, signing in at the lobby, filling out my application, and being led into a room full of beds (open concept, of course). As I laid there with the needle in my arm, my nurse (or doctor, or technician, or maybe someone else, I never really knew) would advertise other opportunities, including a higher premium for selling white blood cells and platelets, which were priced at around $100. By my third or fourth visit, though, it was just another chore that I had marked on my calendar.

Looking back on it, the only memory I carry with me is a dark dot on my right arm, where the second or maybe third needle was injected. It was supposed to heal, but I guess my body decided to give me a mole instead. Now, it’s a pretty fun dinner conversation because when I bring it up, people seem very surprised.

Trying (or not) is the only right answer

When I first started writing on Medium, I realized how hard it was to be a content creator. As a solution, I built an app that was meant to let content creators set a price for answering questions from their fans. The idea was that fans would enjoy having those interactions with creators and probably are interested in asking all sorts of questions. Content creators could use the platform to interact with their top fans while also earning more to support their work.

Fast forward two years later, and the app we built is self-sustaining and profitable. Our biggest user base, though, is astrologers and tarot readers. Some astrologers just signed up for it and started using it to take reading requests from their audience because those psychics don't really have a platform to do it. Alternatively, they would need to take PayPal payments, manage who sent them payments, make sure they don’t forget to answer questions, handle potential refunds, etc. — our app did it all for them.

We didn’t advertise to psychics. To this day, I’m still unsure of how the first ones started signing on. We had built an app that honestly would’ve failed if it wasn’t for this mysterious emergence of a group we never thought about targeting as users.

We could’ve argued around the coffee table, weighing the pros and cons of whether or not it would work. At the end of the day, though, the decision whether to try or not is the only answer that matters; all the logic and statistics and numbers being thrown around couldn’t have accounted for what happened with our app.

C’est la vie

Starting my first company was tough. Apart from the daily challenges, my own thoughts kept me up at night. My friends started their careers, getting stable, decent-paying jobs that let them enjoy their weekends and holidays. Meanwhile, I was making trips to the blood clinic every month and a half.

For better or for worse, I kept going. Every day, I’d make more phone calls to try to land a sale. The funny thing is, I never sold anything apart from candy for elementary school fundraisers. All I knew was to dial phone numbers and leave a voice message if no one answered. No one ever answered.

One day, I got a callback. I didn’t know what to do and was pretty nervous about answering the call. My cofounders huddled together over my cell phone, and I accepted the call on speaker.

“Hello? Is this Kenny?” the voice on the other line asked.

“Yes, this is Kenny,” I responded.

“Well, Kenny,” the voice continued, “I wanted to call you back because, in all of my professional career, I’ve never heard such a terrible voicemail. I have no idea what you do, so I needed to find out. Anyway, no, I don’t want any of whatever you’re going to sell me.”

And he hangs up. Awkward silence and disappointment filled the room, and we were once again back to square 0 with no light at the end of this tunnel. To be fair, my voicemails sucked. I recall it being something along the lines of, “Hi, this is Kenny. Call me back.” I give the guy credit for even responding.

Eventually, though, sales got better. We got lucky enough to find an early adopter, who purchased some things at deeply discounted rates. But it was enough to start getting the word out, and eventually, other customers started calling in as well. I remember when I could finally afford a queen mattress (I had been sleeping on the floor for a while). Before long, we had scored some big fish, and the business started taking off.

Sometimes things work out, and sometimes they don’t. With startups, it’s always a rollercoaster. Unlike with career promotions, where there might be limited spots and many contenders, there’s more than enough success and opportunity in this world for everyone, and many moments that we’ll come across it.

Entrepreneurship is certainly a rollercoaster. As an entrepreneur, we all go through challenges (some unique, others more relatable). Some of those challenges ended up well, while others fall into a disaster. Regardless, over time, they all become amazing experiences that drive your next choice as a weird, seemingly fearless human. At the end of the day, though, we’re just as normal as everyone else — we will continue to have fears. As I sat down in the meeting room and looked back out through the glass, I realized I had one fear: cubicles.

The Startup

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