Imagine driving a mammoth 40-foot trailer from San Diego to NYC, navigating commercial vehicle lanes and maneuvering through the Lincoln Tunnel while steering around merciless New York drivers all in the name of golf. Well that’s exactly what Jenn Harris was doing before I called her for an interview. The young CEO of Street Swings, an innovative new company that provides a unique mobile golf experience, is on a 40-day tour around the Big Apple promoting the game of golf. Her innovative approaches to growing the game are starting to garner nationwide attention, and we wanted to find out what makes this golf entrepreneur tick.

You have more than one golf business. How did you come across the idea for your first entrepreneurial venture High Heel Golfer?

I came up with High Heel Golfer back in D.C., when I was working for a defense contractor. I was excited to finally use the golf skills my dad taught me growing up for business. When I asked my boss if I could play in a tournament with my clients, he said no unless I wanted to take a vacation day and pay for it myself. A few weeks later the clients heard I wanted to play golf and invited me out. We hit it off and they started asking me to be on all the big projects. A few months later I got a raise — all this stuff was happening because of my round of golf.

Then one day when I was sitting in my cubicle, I started brainstorming what I was passionate about and what I wanted to do. I decided there was something missing in the market to help business women play golf and leverage it to be successful the way I was becoming successful and basically get noticed. I wanted to help other women do the same and decided to leave my job and start the company.

What led you to the idea of Street Swings?

Street Swings was a pivot from High Heel Golfer. I was getting frustrated that as the guru of how to leverage golf as a business tool, I wasn’t allowed to teach because I wasn’t a certified teaching professional. I chose not to go the teaching route and to utilize different golf courses and their reaching professionals. A lot of things were getting in the way like they were stuck in traffic, or hung up at work, or the ladies didn’t know what to wear so they decided not to come.

Then one day I was doing a client event at Full Swing Golf and watching clients have more fun at their facility than they were having at my events. I loved the idea of having a cool setup with a few simulators, a bar, food and music, but that didn’t solve the underlying problem that it’s hard for business people to get there after work. That’s when I thought, let’s make this concept mobile.

What are some challenges you’ve encountered on your entrepreneurial journey?

The biggest challenges are with Street Swings. I started with a 41-foot trailer that was seven years old and one of the challenges was getting the thing to even open up. Trailers flex — it’s like its own organism and learning how they flex, how to drive it and open the sides was tough.

On the business side, really understanding what your clients want and how to deliver that for them is a learning experience. Some people want your personality and your vision, while others just want the product and the CEO to step out of it. Learning how to step back as a CEO is a challenge sometimes.

As an entrepreneur, you probably roll your sleeves up and do jobs you wouldn’t typically do. What are some of the unique tasks you’ve encountered as a business owner?

I started a company in a space that’s never really been attempted, in a field that I never learned — and now I’m traveling across the country in one of the most complicated driving experiences ever! I had to drive through the Lincoln Tunnel, but figure out which lanes are for commercial driving so I can’t use Google maps. Instead I had to use a truck map that I found online and make my own directions. I had to get through a 13-foot wide space on a turn to get up over a 7-inch curb to get to the Oculus Pavilion at the World Trade Center, the first truck to ever do so.

How does it feel to take that first leap in pursuing an idea and watch it come to fruition?

That’s my favorite part – building something is a high for me. I think as a kid I always wanted to be an inventor, so Street Swings is fun because it’s a tangible product and I’m working on sketches with the trailer manufacturers and piecing all these different things together that no one else can visualize except for me.

Can you relate the challenges/joys/pitfalls of running a business to playing golf?

I was at a business conference a few weeks ago, listening to this guy talk about golf in a different way than I’d heard before. He said, “if you look at golf as just keeping ball in play, same ball the entire round, then it’s more like business than scoring well.” Often times I felt like I needed to hit good shots and score well to succeed in golf, and it’s how I looked at my business. I was worried about landing big clients and making more money, but a true business is one that stays in play, keeps growing and makes it to the finish line.

Where do you see the golf industry in 20 years?

I think there will be more things like Top Golf or Street Swings to get people excited about the game. If you make it where someone can enjoy the game without being a good golfer or they don’t have to play 18 holes it will encourage more people to try it. Look at surfing for example: you can hit the water with a boogie board or a skim board and then you can graduate to a long board then a short board. But in golf people think “I have to play 18 holes to be a golfer” but it doesn’t have to be that way—there are executive courses, par 3 courses, the driving range, etc. I think if the golf industry continues to embrace those activities, it will grow.

Do you think playing golf prepared you for the business world?

Through golf I was introduced to all kinds of people and people I normally wouldn’t meet if I wasn’t on the golf course. Condoleezza Rice was walking down number 10 at Cypress when I was walking down a nearby hole. I’ve met millionaires, billionaires and top CEOs on the golf course, which I otherwise wouldn’t have. So, I don’t have a fear of carrying a conversation with successful people because golf is our common ground. Maybe I did when I was first starting out, but now it’s more like: we’re both on the course? Okay, let’s have a conversation. They’re probably looking at me thinking who is this girl? She must be important. That wouldn’t happen at a restaurant or somewhere else. Once you step up on the tee box you’re an equal.