EO Member: Matt Stringfellow
Years in Business: 7
How long have you been a member of EO Chicago and why did you join the organization?
I joined in the fourth quarter of last year because I’ve been around other EO members at brokerage firms and saw that the organization had a positive effect on the leadership at those companies. My business partner, Greg Oswald, was also an EO member in Park City, Utah. He recently got into YPO out there so it made sense for me to join EO. The shorter answer would be that I wanted to explore the personal and professional growth opportunities that EO provides.
What was your first job?
My first job was Matt’s Lawn Company when I was 17 or 18. I had two employees—friends of mine—as well as one truck, one trailer, and a rideable tractor.
Can you describe your entrepreneurial journey? Where did you start and where do you hope to go in the future?
I’ve always been in sales, working as an independent contractor even when I was with other brokerage firms. Because of this, I never had a ton of support or guidance and already felt like an entrepreneur even before I started my own business. So I was very open to and excited about starting my own company.
Down the road with SOLJETS, I want what I think everyone wants—to do a lesser volume of transactions for a greater profit. I also see the value in maintaining our current course. We have a lot of new and exciting projects at the moment, so I’m pretty satisfied with where we’re going.
What do you enjoy most about your work?
I fell into this business because I went to school to be a pilot. I graduated from Purdue’s flight technology program and it’s absolutely my passion, so my favorite part is flying. I still do deliveries and mentor training with my clients when they buy jets. About 50% of the clients I deal with are owner-operators, so they sit up front and fly their families or employees in their own jet. It’s fun to talk to them about the operations side of things—the flying, the performance, and the avionics.
What daily challenges do you face at work?
Not having enough time in the day and struggling to stay focused. In particular, I struggle to maintain a focus on growing the company while also accomplishing my five year goals.
What is the best career advice you ever received?
“Never give up.”
What’s the coolest thing you’re working on right now?
Two things: one, I’m in the process of buying a helicopter for my personal use out of Kuala Lumpur. And two, we’re currently closing on the purchase of a Gulfstream out of Canada. It’s an eight-passenger super mid-size jet that can fly from here to Hawaii.
Who or what inspires you?
Mainly my father, rest his soul.
If you could go back in time five years and share advice with your past self, what advice would you share?
“Enjoy the calm times.” I think a lot of us have this tendency to panic and immediately start trying to counter and correct when things get quiet in business or you see your numbers drop. Now, though, I appreciate the downtime and use it to work on myself. I think I’d be farther ahead now if I hadn’t stressed myself out so much five or ten years ago.
What is the greatest challenge you have overcome?
Losing my dad in a car accident and then almost dying in a car accident within two weeks of each other.
What brought you to Chicago?
Do you like living in Chicago?
I don’t dislike it, but I grew up in Boulder. I love the mountains and skiing, stuff like that. I don’t love the winters here but I do love taking my boat out on the lake in the summer.
How do you find work-life balance?
It’s not my specialty, but I’m learning to be better at it. I think it’s about putting your phone down and having dedicated family time.
What are your favorite things to do outside of work?
Aside from flying, I’m into day trading penny stocks. I enjoy learning about startups or really doing anything that takes my mind off of aviation. I also DJ on the side as a creative outlet. And I love the outdoors—skiing, snowboarding, hiking, camping, etc.
What’s one thing still left on your bucket list?
I’d like to travel more—countries in Asia, India, and South America.
What are you currently reading?
A book that a fellow EO member gave me—The Gap and the Gain by Dan Sullivan.
What’s your favorite restaurant?
RPM Seafood and Pizzeria Portofino in the city and The Capital Grille in Rosemont.
What is your favorite part about working in the Chicagoland area?
My network—I have spent half of my life here.
What is your top Chicago activity?
My happy place is on my boat on the lake.
Where’s your favorite place in the world to visit?
Turks and Caicos—the water is amazing, I highly recommend it.
Thank you to Matt for sharing his story for our February member spotlight. The Entrepreneurs’ Organization is a global business network of more than 14,000 entrepreneurs in 198 chapters and 61 countries. EO is the catalyst that enables entrepreneurs to learn and grow from each other, leading to greater business success and an enriched personal life.
If you’re interested in becoming an EO Chicago member, check our membership requirements and submit an application to join today.