323: My entrepreneurship journey

I haven’t told my entrepreneurship story in a while, but hopefully the pieces will help you understand my journey and perspective on life and business. I was born in southern Indiana, my mom was a school nurse, and my dad was a construction manager for a real estate developer. We were definitively middle class: I went to public school and didn’t grow up with wealthy neighbors or friends, but my dad understood business.

At 13 years old, my dad’s boss called him into his office and said that there was an opening to mow lawns for some commercial clients. My dad offered up my services, saying that I was ready to work. He set me up for 20 hours a week of mowing and sat me down at a table to give me a crash course on operations: he would lease the mower to me for $20 a week, he would buy me a trailer to transport the mower for $20 a week, and I would pay for my mom to drive me between sites since I didn’t have my license.

My first job was at a shopping center, and there was trash all over the grounds that I mowed over. When my dad scolded me telling me that I couldn’t mow over trash, I tried to quit in an outrage accentuated by the summer heat. My dad didn’t let me quit, so I went out and finished that first job, and suddenly it didn’t seem so bad to keep going.

Quickly, I realized I was making $40 an hour even after all my expenses. I got tired of my mom driving me, so I went to the high school and advertised a job opening, eventually hiring a kid to drive me around and help out for $15 an hour. This whole experience taught me how to solve problems, how to think about problems, and the fundamentals of what goes into running a business. Going off to college I had about $40K saved up from these summers working.

I went to Cornell for track, and after my junior year I posted my apartment on Craigslist for the summer while I was gone. Instead of subletting, I got offered $150 to pick up a person’s belongings and store them in a room for the summer. This sparked an idea, so I started to put out flyers and filled my apartment with other people’s things for the summer. Quickly, my partner Dan and I had a few thousand dollars in cash and were handling storage in our apartments, at which point we shook hands and formally started Storage Squad.

We set a goal for 250 customers in our first full year of operations and knew that we needed to operate on more than just Cornell’s campus. We expanded to Indiana, Illinois, and Iowa, campuses where we had friends we trusted to operate and included in our revenue-sharing plan. We used student loan money to buy vans off of Craigslist for $1500 each and just met our 250-customer goal. It was a stressful ride though, I found myself answering customer service calls at track meets and picking up boxes from customers the morning of my graduation.

After college, we decided to take Storage Squad full-time, opening at Penn State, Syracuse, and other locations throughout the northeast with a huge hub in Boston. Our revenue grew from $500K to $1.2M, and then to $1.7M, but it was an exhausting business. At peak, we had 6 full-time employees and 180 working part-time, we were renting box trucks and leasing warehouse space at 25 different colleges, and had to handle the logistics of delivering boxes, hiring and recruiting employees, and storage all with highly seasonal demand. We did this for several years and found profitability, but Dan and I were sleeping in warehouses, went weeks with just a few hours of sleep a night, and dealt with issues like customer service complaints and vans breaking down.

We made a little money from the student storage game and decided to put it towards real estate by building a self-storage facility in Ithaca. We got the property under contract for $250K and broke ground in July 2016, aiming for a 38K square foot facility and a $1.9M budget. My first job was to raise money, and I was turned down by the first 20 banks I walked into before I was able to secure a loan, but we still had to raise $500K beyond that. It took a year and a half of pitching to family friends, college friends, and even getting money from the broker who sold us the ground for our facility, wearing out every single opportunity to raise money that we could.

As luck would have it, we blew past our budget and the building cost $2.4M to develop, so we had to go out to those same investors and ask for more money, but we were finally open for business in May 2017. The property started leasing a ton of units, cash was flowing well, and we were running Storage Squad on the side. When we went to the bank to refinance, we were looking at a value of $5.25M, allowing us to give money back to investors and have some left over. We turned around and bought more self-storage, and then didn’t look back.

Things at Storage Squad became chaotic in 2020 with the onset of COVID-19, as students were sent home from campus on incredibly short notice. It ended up being the best year ever for us from an income perspective and opened a window for us to sell the company for $1.75M, even paying out bonuses to our employees.

The self-storage arm grew as we bought a property in Erie, PA for $600K, and it’s now worth $2.3M after we did a cash-out refinance. A few other early properties were huge wins, and the rest is history. I got on Twitter to grow my brand and podcasts, and the last piece of the puzzle was solved when that opened up my inbox to tons of new investors. In 2021 we bought $50M in self-storage, the company grew to over 50 full-time employees, and our properties have continued to operate well.

The big takeaway from my story is that you don’t need a new, sexy, get-rich-quick idea. I’ve always gone out just looking for a way to make money, executed well, and over a decade my life has changed beyond what I could have predicted. I got 8 years of practice in the trenches of a really hard business, and that helped me become good at what I’m doing now. Stress is relative, so being able to deal with a ton of high-stress situations has helped me work through them and stay level-headed over time. What we learned in our days at Storage Squad has us running circles around other people in the real estate game, as it gave us a huge crash course in hiring, managing, and making decisions.

Check the show notes here: https://sweatystartup.com/the-sweaty-startup/

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About Me

I started the Sweaty Startup in December of 2018 because I believe the Shark Tank and Tech Crunch culture is ruining the real spirit of low-risk entrepreneurship.