
I slept on a park bench in Brooklyn last night.
Before that starts to seem like an awful thing, please note that it was gorgeous out. The sketchy circumstances surrounding my Bushwick siesta aren’t important because this isn’t rock bottom.
*leans back in recliner and takes puff of pipe*
Rock bottom was actually a couple years back. It was the Spring of 2013 and I had just graduated college the summer prior. I was working second shift at a law firm, which is a sexy way of saying I was working from 5pm to 12am every night doing bullshit work, but getting paid pretty decently. It allowed me to work on CycleStay, me and Justin’s first “company” or whatever one calls a concept that a couple kids in an entrepreneurship program tried to make go post graduation. It didn’t go, by the way, which is why you’ve probably never heard of it.
Anyway, back to rock bottom. Working second shift at a law firm allowed me to wear my CEO hat during the day. Mentor meetings, team meetings, investor meetings, work, emails, sleep(ish), rinse, repeat. Looking back, I had no clue what I didn’t know and ultimately, as it turned out, CycleStay wasn’t the right thing at the right time for the team we’d pulled together. Neither here, nor there though, because that’s all part of the journey. What was really important is that we were committed to figuring it out, so meetings and evening work was the thing. I was 22 with endless energy.
At the same time, I was working for my mentor and senior capstone professor at my alma mater (Go Rams). He’d invited us back to help think about curriculum in the program we’d just graduated from. The money wasn’t great, but it didn’t have to be. I was working a few hours a week for a man I thought (and still think) the world of, I was continuing to learn from some of the brightest academics in the business, and I was having a blast. The law firm paid the bills, the university kept me sharp, CycleStay was the dream.
For some reason though, content is not a concept I’ve ever been able to grasp. Over the course of a week, two of my best friends called (separately) to let me know that they loved me but thought the law firm was killing my passion and drive. That same week, my Department Chair shared that, in his opinion, I have a “low tolerance for minutiae.” (He wasn’t wrong.) A ton of unsolicited feedback in a short span of time, I know. But, with a few long days of reflection on passion and minutiae along with a few conversations with my concerned parents, I quit the law firm. No plan, no savings, just a commitment to not being boring. Call it stupidity, call it youthful exuberance; whatever, I was free.
And then reality happened. Keep in mind, the law firm was my only real source of income. I was only working a few hours a week at the university getting paid something close to minimum wage and, outside of a business plan competition our senior year, CycleStay wasn’t paying anyone anything. Broke was an understatement. I was picking a bill or two a month to pay and letting the rest sit until the next month when I picked different bills to take care of. We shifted a few things around at the university which got me to 20 or so hours a week. It helped, but I still wouldn’t call it gainful employment. Then my car broke down. My beautiful ’93 Honda Prelude wouldn’t start and was parked in a lot that I hadn’t paid for in a month or two. Needless to say, said Prelude got towed. By the time I got the bill, it was just over $1,000. I let the towing company keep the car.

Rock bottom is a funny thing. Even when it’s self-inflicted, it still sucks. I was as committed as anyone to my work and I had no intention of letting a simple lack of money get in the way of building something I felt was important. Money be damned. That’s not to say I didn’t wake up every morning and flip the light switch to make sure the electricity was still on. I’m just saying stress comes with the territory. It was a shitty time, but I was alive.
More importantly, when things turned around, I still had the experience of that Spring to lean on. Dr. Rutherford and I ended up getting a grant funded to pay for my work at the university, a feat in and of itself. Justin, a few friends, and I launched Coffitivity, one of TIME’s Best Sites of 2013. Things turned around and I got back on my feet.
I look back on that time fondly. Admittedly, the lowest of lows is relative. People I know have been in “the suck” worse and longer than I ever was. Even so, for a 22 year old with no real world experience, it was a ton to go through and something I think has made me better. My perceived tolerance for risk, stress, and psychological pain increased drastically that Spring. I learned a lot about myself — what motivates me, what scares me, what keeps me up at night, and what keeps me going.
Ultimately, it’s that time in early 2013 that I share with budding entrepreneurs most frequently. Even with all of the exciting times over the course of my short career, it’s that time that keeps me grounded when things are toughest. Stakes have changed, of course. As a more mature founder, there are investors, payroll, and people counting on me to not be rash or stupid. Life is different now, but it’s that Spring that I keep in the back of my head when I feel like quitting every so often. It’s been worse before, and it was alright. Once you’ve been to rock bottom, the debilitating fear of hitting rock bottom is no longer the unknown that you’re fighting frantically to avoid. It’s real and it’s not ideal, but it’s not the end of the world. Rock bottom didn’t kill me and now I know it never will.
So yeah, I slept on a park bench in Brooklyn last night. I didn’t plan on it, and I’d rather not have, but other than wishing that damn light hadn’t been on all night and needing some bug spray, it was fine. I’ve slept in worst places in worse states of mind. Besides, my AirBnb will be ready this afternoon, I’ve got a badass team, there’s a new Techstars class I get to hang with tonight, and I have irreplaceable family, mentors, and friends. What’s there to complain about?
Today is a new day and I woke up still a founder. For that, I’m fortunate and eternally grateful. Game on.
A huge shoutout to Dr. Matt Rutherford, Justin Kauszler, and Nicky Monk for hooking it up in ways they may not fully appreciate even to this day. Also, a big thanks to Chase Marchetti and Moira Spahic for nudging me out of the minutiae of a law firm I had no business working at in the first place.
Note: There’s been a humbling outpouring of folks offering couches and door codes over the last day or two. I’ve got my AirBnb all sorted, but I appreciate y’all. Much love.
