Jesse Fowler has enjoyed a lot of successes in his business career, but when I ask about his most important milestone, he instantly names a failure – the day his web design business almost went under.
He was 34 and living in Scarborough, designing inexpensive websites for a handful of small businesses. The numbers just weren’t adding up. He was discouraged and reluctantly thinking about getting a “regular” job. That’s when his dad suggested talking with a business coach. He did, and it changed the trajectory of his company, OSC Web Design.
With help from Jim Lyon of Summit 9 Consulting, Jesse redesigned his business model. He started offering comprehensive packages including website design, development and strategy services, search engine optimization, photography, even videography. It was more expensive than what he had been doing, but it would take all the work off his clients’ shoulders. It worked. Today, OSC is a robust team of ten specialists managing clients across the country. Their websites and apps help businesses such as J.B. Gottstein deliver wholesale groceries and medicine to remote communities in Alaska; they allow Lobster 207, a lobsterman-owned cooperative, to fill orders from around the world; and they work with Standard Baking in Portland.
Amidst this success, Fowler still prioritizes small businesses in Scarborough, where he has lived since he was a teen. This spring, he is proud to be updating Pat’s Pizza’s Scarborough website (they were his first client back in 2011) and he is helping Dunstan Smokehouse launch its online ordering platform. He is even helping this publication improve its website, offering a lot of insightful, free business advice along the way.
During even a brief conversation with Fowler, his entrepreneurial tendencies are immediately evident. I first met him in his role as the president of Scarborough Buy Local. As I asked about the group, he asked about this magazine, and then began sharing the stream of ideas that sprang to his mind – excellent suggestions for distribution, marketing, and content.
This phenomenon wouldn’t surprise those who knew Fowler well. He was an entrepreneur before he knew the meaning of the word. As a child, he was always a hard worker, whether selling vegetables in front of his house or hawking items for school fundraisers.
For one fundraiser with a particularly enticing prize (he can’t remember what), he started knocking on doors as soon as he got home from school, even though it was raining. He recalls thinking, “I’ve got to get out there or the competition is going to beat me.” As a high school senior, Fowler bought his first business, Bayside Bait & Tackle, a convenience store, gas station, and tackle shop in Pine Point (now the Garage BBQ). How did he have the confidence to do that? “I was 18 and, ‘Why not?’” He could work from 5am to 9pm and still hang out with friends afterward. It was a great job for a young person, in part because he worked nonstop for nine months and then had three months off to travel the country in the winter.
Fowler closed the business after a few years, having gained even more confidence and a lot of practical business experience. He managed the Camp Ellis General Store for one summer and turned it around to a profitable business in just one summer. He tried retail in Old Orchard Beach and sold apparel & airbrush tattoos at fairs. He even lobstered for a few years. He has been self-employed his entire life, minus one year when he worked at his father’s fuel card company. It was there he learned about the need for web design services and importance of SEO, which eventually led him to start OSC Web Design.
In addition to OSC, Jesse is now a partner of three other businesses – My Energy Doctors, Drone Your Own, and My Contract Doctors, and is an investor in Dunstan Smokehouse. His long-term goal is to have stakes in about ten companies and focus his skills and energy into helping them continue to grow.
Reflecting on his life as an entrepreneur, Fowler says, “No one would be shocked.” Sometimes his business mindset makes family members roll their eyes and say, “Everything’s a business idea.” Recently a friend gave him a cocktail recipe and quipped, “Don’t go trademark this.” With a surplus of ideas, Fowler has learned to be selective. “You have to be patient for the right one to come along. And you have to believe in it fully.”
Fowler’s unique depth and variety of experience helps him connect with the business owners who are now his clients. This is essential to being a successful entrepreneur, he says. “Being relatable helps build trust.” It also helps him in his role as president of Scarborough Buy Local (SBL). This business networking group helps small, independently-owned businesses thrive in Scarborough. Fowler, an inveterate traveler, says his devotion to the group stems in part from his observations of how dominant franchises are elsewhere in the U.S. and globally. He feels strongly about helping independent businesses. Vice president Amanda Huebner says Fowler has “…a visionary blend of web design prowess and leadership…. [His] unwavering support paves the way to success for local businesses.”
Fowler’s SBL work unites two of his deepest passions – entrepreneurship and Scarborough. He grew up visiting his grandmother in Pleasant Hill before moving with his dad to Pine Point 25 years ago. He and his wife, Shannon, now live here with their three children. For Fowler, Scarborough is an ideal base of operations, both professionally and personally. It has great schools, great beaches, and is minutes away from Portland and its airport. Shannon works for an airline and, when time allows, the whole family loves hopping on a flight to an exotic destination. They also love food, which pairs well with travel. They’ve tried ramen in Japan, fish and chips in Ireland, and pasta in Italy. Fowler and his family live in his grandmother’s house, which he bought from the family a few years ago. What was once the site of his lowest professional moment is now where he manages multiple businesses, dreams up new ventures, and helps other Scarborough residents find success for themselves, cheering for them every step of the way. At just 39 years old, the future is bright.
JESSE FOWLER’S ADVICE FOR YOUNG ENTREPRENEURS
We asked what advice Jesse would give to young people thinking of starting a business. Here’s what he said.
What are some of the most important lessons you’ve learned in two decades of entrepreneurship?
I have learned to fail, I have learned that not everything is easy and comes naturally. I’ve learned that it’s most important to know what you don’t know – be aware of that – and find people who fit those weak spots and hire them. Don’t settle for mediocre, always strive for the best. Good enough is never truly good enough.
I’ve changed by realizing that I need to rely on the right people, such as my business consultant, and learning to let go of my own pride. I’ve learned that there are so many amazing people in Scarborough, in Maine, and throughout the world. There are many entrepreneurs who have some amazing ideas that you would never have thought of. I’ve learned that even as an introvert, I need to get out there and network – it’s really hard to meet all the right people from my home office after all.
What advice would you give to young entrepreneurs?
I think that you need to start by letting go of the fear of failing, realizing that you don’t know everything and no amount of preparation will change that. It’s times like these that you should find others who have paved the way, lean on them when appropriate, understand they have been there and have had the challenges that you are going to have, and probably know how to navigate them best.
If you’re going to fail, fail early. Everyone fails in one way or another, so although you don’t try to fail, understand that’s part of it sometimes, and you have to get back out there and go again. It’s better to fail while you are young and learning than later on when you have a family and other responsibilities to take care of.
For some smaller points, come up with a business plan, check out the competition – again, someone has paved the way, and competition isn’t a bad thing, it means there’s a market. Come up with SMART goals, then act on them.
Network and meet likeminded people. You are the median of the five closest people to you, so find those who are going to lift you up, give you inspiration and help make you successful, while you do the same for them.
When meeting with a client, listen first, listen last – you’re selling your personality first. If you are a relatable and likable person, your service will be able to sell itself. Don’t be afraid to provide selfless help to others – karma is real and the good you put out will come back to you.
Written by Kate Reilly deLutio. Lead photo by Amanda Huebner Photography.
