Today we’d like to introduce you to Clayton Gentry.
Clayton, can you briefly walk us through your story – how you started and how you got to where you are today.
I grew up in mid-Missouri until I was 15. When I was 5, my father mentioned to me I could go to high school in Switzerland.
Fast forward to 1989, and I was flipping through my mom’s Town & Country magazine and at the back there was a listing for a high school in Switzerland. After somehow remembering what my dad had told me when I was younger, I secretly sent in my application to the school and got accepted.
All excited, I went to my dad and said, “Dad, I need some money.”
He said, “What do you need money for?”
I said, “Do you remember when you told me I could go to high school in Switzerland?? Well, I applied and got accepted and I’m going next year so I need some money.”
My dad was all for it, my mom freaked out. And remember this is 1989/90, there’s NO INTERNET!! So we all flew over and checked out the school and I was lucky enough for them to say yes.
After Switzerland, I got accepted to Babson College just outside of Boston. While going to college, I got a real estate sales license, had an office on Newbury Street, and rented apartments, sold a few condos and even a commercial building.
During my junior year, my father passed away. None of my brothers were interested in going back to Missouri to run the family real estate business so I finished college and went straight back to mid-Missouri with a little bit of real estate experience from Boston.
After being away for seven years in Switzerland and Boston, Missouri was not exactly the plan; however, it was a great start and a definite character builder. We had a small eclectic portfolio of mid-Missouri properties (apartment buildings, retail centers, office buildings, mobile home parks, vacant land and one little storage facility. After reviewing the portfolio, I decided to sell the properties that were ready to be sold, fix and lease up older properties to eventually sell. But there was one property that I gravitated towards – the small self storage facility.
Self-Storage is a service based business attached to a real estate deal. After my experience at Babson, building and growing all kinds of theoretical startups in Babson’s entrepreneurial program, I gravitated toward the real estate deal that had a service based business attached. I enjoyed having the operations and marketing associated with it as opposed to the other rental real estate in the portfolio. So I dove in head first and learned everything I could about the industry.
Shortly thereafter, I was speaking to my old roommate from Boston and his brother who both happened to work for their New York based real estate company. It turned out that they had one self-storage property also. I had just sold a property in Missouri and was looking re-invest the capital (anywhere outside of mid-Missouri).
We decided to partner up with each other on a shopping center in New Jersey just outside of Philadelphia. Shortly thereafter the vacant land became available. We all decided that if I could get the approvals and put the deal together, I would move to Philadelphia. I moved there, got the approvals, got the financing, hired a construction supervisor and built the first 21st Century Storage location.
While living in Philadelphia, I built and converted several more storage locations from Philadelphia to New Jersey to Baltimore. For the last several years, I’ve mostly focused on buying and selling existing storage properties in the northeast as well as in California and now in the Miami area.
Two years ago, I purchased one property at 200 NW 79th St., Miami. This year I’m redeveloping a former Kmart in Naranja (near Homestead, FL) and have another ground up a little further north from there also on South Dixie Highway. Also, this year I’m opening a fund specifically for self storage investment.
I now live in Aspen, CO with my beautiful wife, Hayley (who I met in Miami) and our two kids. I have to travel to visit my storage facilities, but at least after all that travel, I get to come home to a beautiful place!
Overall, has it been relatively smooth? If not, what were some of the struggles along the way?
Once you start growing and having multiple locations, self storage has its challenges like any business. Since 2000 when I opened the first 21st Century Storage location, I would say the financial crisis presented the most challenge, and opportunity.
Self Storage thrives on transition. In the economy, there is good transition and bad transition. Both provide business for my industry. If the economy is good, people and businesses are buying things and expanding and ultimately find a need to store. In a bad economy, self storage provides a cheap alternative to store belongings while people or businesses downsize. Everybody stores for every reason.
Banks were difficult in the recession. They needed to de-lever their balance sheets. They didn’t just go after those people who didn’t pay, they also went after people and companies who had money and who did pay. All I want to do is rent storage units and add value, but let’s just say I found myself talking to more lawyers and bankers than storage customers for a few years. At the end of the day I learned a lot, never missed a mortgage payment, and ended up making a lot of money.
Alright – so let’s talk business. Tell us about 21st Century Storage – what should we know?
21st Century Self Storage® builds and operates the finest storage facilities by having the most highly trained managers, providing superior customer service and immaculate properties.
We created a Storage University program to train all of our managers to be the best in the industry.
In self-storage, we rent space. My 10×10 is the same as my competitors in size, but we differentiate the experience by how our facilities are kept clean and maintained. One example would be that we don’t just sweep out our units when a customer vacates, we actually vacuum and mop each unit with pinesol. When a customer opens up one of our units, they are spotless. This is one way we differentiate a highly homogenous service.
Any shoutouts? Who else deserves credit in this story – who has played a meaningful role?
I believe that great employees make the difference. I have a small company and it’s hard to compete with the packages larger companies can offer their employees. But I believe each property is only as good as the local managers who run them and the support staff overseeing them. So we try very hard to keep great employees.
The Self-Storage Association and every banker and broker I’ve met thru them have been a great support over the years.
Also, every customer service experience I had growing up from restaurants to hotels to airlines, etc contributed to what makes 21st Century Storage what it is today.
Contact Info:
- Website: www.21css.com
- Phone: 970-920-7833
- Email: [email protected]
- Facebook: https://www.facebook.com/21CSS/

Image Credit:
Jen Senn
Getting in touch: VoyageMIA is built on recommendations from the community; it’s how we uncover hidden gems, so if you know someone who deserves recognition please let us know here.

Joseph Kabatt
October 19, 2017 at 11:59 pm
Clayton:
Congrats on the magazine article and your recent success. I always knew you would bounce back.
Even though there were a few bumps when you started 21st Centuty Storage, I am glad we worked together and you put your trust in me. Together we built some nice looking buildings.
Again, congrats to you. If you are ever in the Philadelphia area and feel the need for a coffee, call or text me at 610-715-4023.
Sincerely,
Joe Kabatt
Virgil Gene Baker
October 21, 2017 at 4:45 am
Way to go–Clayton Gentry….Come by sometime and you can cook my breakfast again. Love to the family. Virgil Baker