Leap of Faith: An Interview with Entrepreneur Jason Watford

An Interview with Jason Watford

Jason Watford started his cleaning company in 2014 with a mop, a bucket, and 5,000 dollars. Eight years later, he’s built a commercial cleaning empire that serves over sixty different clients and employs dozens of employees and subcontractors across the Big Island of Hawai`i. He is also one of Suite Possibilities’ oldest clients. I sat down with Jason to learn more about his business and talk tips for island entrepreneurs. 


Jason grew up working for his dad’s Service Master franchise in Panama City, Florida. His dad was a serial entrepreneur who owned many different businesses over the years. “I was his guinea pig,” says Jason. While he wasn’t always excited about the work as a teenager, he learned how a cleaning business operated and what it took to work for yourself — something that would give him the guts to start his own company from scratch years later. 

Building a Business 

Jason’s business, JW Cleaning Systems, LLC, began in 2014 with him driving around Kailua-Kona, Hawai`i in a used van, knocking on doors. He started out doing residential cleaning. Whatever jobs he could find, he took. He cleaned vacation rentals, private homes, windows, floors, you name it. He even delivered groceries a few times. His hard work was worth it. By 2015, he was bringing in 10,000 dollars a month from his residential cleaning accounts. 

But then, he met a man who told him to give all his accounts away! Jason met Keola Boak, who had a successful commercial cleaning company, in a local chapter of the business networking group, Business Network International. “I was thinking, you’ve got to be kidding me,” says Jason. But he took Boak’s advice. He got rid of all his residential accounts but one and started going after commercial clients with a specific focus: financial institutions and commercial properties. 

After a few nerve wracking months, the leap of faith paid off. He landed a contract with all the rental car facilities on the island. Then, a few months later, he landed a really big fish: Bank of Hawai`i. Jason remembers flying over to O`ahu for a meeting at the corporate headquarters. They asked how many employees he had and he said twenty-five. In reality, he only had two guys on staff. As soon as he got back to Kona, he started hiring people like crazy. Simply put: say YES and seize the opportunity. The details can be worked out later.  

His Suites Story 

In 2017, Jason’s business grew by 400%. He credits Suite Possibilities for enabling him to scale. “Suites is an integral part of my business,” says Jason. “Without them, I wouldn’t be able to operate at the capacity that I do. They’ve got the entire administrative side of my business streamlined.” Jason uses the full portfolio of Suite Possibilities services, including bookkeeping, mailbox services, virtual receptionist, and more.

Jason is a father of two young boys – Declan and Phoenix – with his wife Sarah. One of the greatest benefits of scaling his business and delegating administrative tasks is more time for his family. It also means more time for his passions like hunting and golfing. “For me, entrepreneurship is about the pursuit of personal freedom,” says Jason. There is less stability than a 9-5 job, but you get to build the life you want. 

Advice for Entrepreneurs 

As someone who has gone from humble beginnings to extreme success in the span of just eight years, I asked Jason if he has any words of wisdom for entrepreneurs just starting out. He shared three key tips: 

#1: Get started. 

Just take action. Get a mop and a bucket and start knocking on doors. Don’t worry about the details. Just move your feet and the rest will follow. 

#2: Sales cures all. 

“I see so many people get hung up on their expenses, their profit and loss, their marketing, etc.,” says Jason. “In the beginning, just focus on sales. As long as you’re selling and closing, you’re going to be just fine.” Jason likes to live by the acronym ABC – “always be closing”.  

While Jason may be a natural salesperson, the art of sales can be learned for those less inclined. He suggests to stop thinking of sales as sleazy. Everything in life is a sell, whether you’re going out on a first date and trying to get the girl or guy to like you, negotiating with a client, or bargaining at the flea market, he says. There are many resources out there for learning how to sell. He recommends a classic: Dale Carnegie’s How to Win Friends and Influence People as a must read for entrepreneurs. 

#3: Find a mentor. 

“I’m not the smartest guy in the room,” says Jason. “I am where I am because I am surrounded by smart, dependable people.” They include his long term mentor and friend Keola Boak, his employees, the Suite Possibilities team, and a network of professionals and business owners who he regularly bounces ideas off of. Asking for help – it’s probably the most important thing an entrepreneur can do. 

Work With JW Cleaning Systems

Jason’s company JW Cleaning Systems, LLC is always on the look out for solid people to join their team. Full time and part time positions are available. Full time benefits include competitive pay, medical, 401 K, annual bonuses, employee parties, incentivized work, and flexible schedule. Interested candidates should call 808-446-5630 and arrange to fill out an application. Visit them online at JW Cleaning Systems LLC.

About Suite Possibilities 

Founded in 2015, Suite Possibilities is a resource center and meeting place for Hawai`i small business owners. With services like conference room rental, office rental, professional mailbox rental, virtual receptionist, bookkeeping, and more, Suite Possibilities supports small business owners in Hawai`i to scale up and succeed. 

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About the Author  Emily Gleason is a writer and web designer based in Kailua-Kona, Hawai`i. Learn more and connect with her at: https://mthewriter.com/