We recently connected with Tommy Galan and have shared our conversation below.
Tommy , thanks for taking the time to share your stories with us today Risk taking is something we’re really interested in and we’d love to hear the story of a risk you’ve taken.
Risk taking has always defined my life. I don’t jump out of planes, or drive fast cars, but I do tend to jump and move fast in life choices. As an undergraduate student, I took a chance and went to law school. Six months after I graduated, I quit my job at a law firm, signed a two-year lease on an office in Manhattan, signed a mortgage on an apartment, and with $10,000 total to my name (not to mention $65,000 in student loans), I started my own law firm and my own life. The odds were against me. However, within six months, my partner and I took over another law firm and in my early 20’s, I owned a successful firm with over 500 cases in litigation.
Over the next 7 years, I managed my practice, had a smashing good time in NYC, started performing comedy, got married and had my first of three sons. All risks in their own right!
In 2010, I decided to sell my law practice and become an improv comedy teacher and performer. I started volunteering as an intern at NYC’s Peoples Improv Theater (The PIT), mopping floors and locking up at night. On April Fool’s Day, we signed the contracts with the new firm owner. When I returned home, I found correspondence from the NYS Continuing Legal Education Board, that my class “Improv for Lawyers” was accredited for continuing legal education. I was able to use this accreditation to begin teaching improv through the theater, and within a few months, I was the Director of Corporate Programming traveling all over the US and Canada to teach attorneys and other organizations the real-world benefits of improvisation skills and training.
Three years later, came our biggest risk and adventure. My wife was offered a new job in San Diego. Even though we had built our lives and careers and family in NYC, we made the life-changing decision to accept it. Four weeks later, we said goodbye to New York, packed our 4-year-old and 8-month-old sons in the Honda CRV with our 75lb dog, Bella and left for San Diego. We were on our own over 3,000 miles from family and friends, but sometimes it’s important to have no other choice but to make it work. There were so many challenges. Within a week of our arrival, our dog needed surgery. A week later, our landlord put our apartment on the market to be sold, and although I was still working remotely, part-time, for The PIT, it wasn’t enough to sustain us in this new and very expensive city. So, I started San Diego Gutters to do some rain gutter cleaning on the weekends.
Within a few months it was up and running. After the first year or so, there was an El Nino, which caused a very busy rainy season and many clients began calling to have their gutters serviced. Everything was moving along nicely over the next few years, but risk, adventure, and taking chances continues forever. We bought the apartment, and had another baby, I started performing and teaching at Finest City Improv in San Diego and continue there to this day. It’s my home stage in San Diego. A few years later my elderly father moved in with us and we moved a year later to a larger home. My wife wound up quitting her job and becoming a freelance writer and now manages a team of 50+ writers. This year, I started my newest venture, SD Roof Inspections, and I’m working on new performances as well as performance course development.
Risks are scary, but it helps to start early and young. When I was in my 20’s, I could take bigger risks because I didn’t have a family that was dependent on those decisions. In my 30s, I was able to take risks because of my wife and kids and support structure. In my 40’s I find that my risks are certainly more calculated and intentional because my responsibility level is so much greater. However, a day will come when the kids are out of the house, college is paid for, and it’s only me and my wife again. When that time arrives, I’m sure we will challenge each other to continue taking risks. Who knows, maybe we will jump out of a plane together, and then drive fast to make it to another performance!

Tommy , before we move on to more of these sorts of questions, can you take some time to bring our readers up to speed on you and what you do?
I’m a performer and an entrepreneur. I perform improv comedy and I also own SD Gutters (a rain gutter cleaning company) and SD Roof Inspections.
We provide a very simple service…we clean rain gutters.
We also offer some minor repairs, but as soon as it rises to the level of a major repair or installation, we refer our clients to the installation companies.
We are known for customer service, and we are proud to treat all of our clients as we would our own family.
What sets us apart is a personalized service. You call me. You email me. You hear back from me. You see me on the day of service. You know exactly who you are dealing with and I follow up with you each year.
Any thoughts, advice, or strategies you can share for fostering brand loyalty?
Rain Gutter Cleaning and Improv Comedy are long term relationships. Your gutters will get dirty and your soul will need lifting.
By offering hard work, commitment and honesty clients return year after year, show after show!
Can you talk to us about how your funded your business?
I’ve run many businesses over the years, and I’ve started all of them on a shoestring budget. Spending lots of money in the beginning isn’t a secret of success. It’s only a great way to waste money. Even if you have the money to spend, be resourceful because a time may come when you won’t have the money to save you and you will need to rely on other means. Be resourceful. Spend time instead of money at the beginning and get it off the ground!!!
Contact Info:
- Website: www.sdgutters.com
- Instagram: @sandiegogutters
- Facebook: @sandiegogutters
- Twitter: @sandiegogutters
- Yelp: https://www.yelp.com/biz/san-diego-rain-gutter-cleaning-san-diego-2
- Other: Phone: 858-208-0612 Email: [email protected]

