Feature Story

Jay Winchester: Word Wrangler, Copy Cowboy
By Carol Cortright

You’ve heard it before—Content is king!

What is content? Simply put-- Words!

No one knows this better than Jay Winchester, president of The Winchester Group, a Tampa-based copywriting company that “puts words to work” for a variety of clients, from Fortune 500 firms to local businesses.

Jay honed his writing talent “in the highly competitive world of freelance writing.” Now, at the helm of The Winchester Group, he provides services such as creative consulting, advertising copy, publicity materials, scripts for public speaking, and editing/proofreading assistance.

Jay Winchester’s diverse history in communications gives him a unique perspective on the power of words and their many applications. “I learned how to read with comic books,” Jay says of his early years, “and was writing poetry by age 11. I’ve always had an aptitude for communicating.”

In the beginning, however, Jay felt a disconnect between himself and the other men in his family. His grandfather, father and brother all worked in construction, an occupation that held no allure for him whatsoever. After a childhood spent moving from place to place—his grandfather was in the union and took the family wherever there was work—Jay said he “blossomed” when they finally settled in Detroit. While Jay knew what he didn’t want to do—which was to follow the others into construction—he wasn’t sure what he did want to do with his life…that is, until he noticed an Air Force recruitment poster that said “Find Yourself.” Talk about the power of words! Jay decided the poster was speaking directly to him, so he joined in 1972 and worked in computer operations.

When he got out of the Air Force in 1979, someone told him he should go to San Jose and check out this “Silicon Valley” phenomenon. “I did not ‘know the way to San Jose,’” Jay says, alluding to Dionne Warwick’s popular 1968 song, but he discovered when he got there that he loved it and spent the next decade and a half working in telecommunications for Intel and IBM. With his knack for words, he was the go-to guy when new procedures needed implementing—he was the one who could take the jargon and translate it into something everyone else could understand.

IBM transferred him to Florida, but sadly, in 1994, he found himself downsized. The day it happened he recalls coming home, walking the dog, and wondering how he was going to tell his wife he lost his job. He tried being a Rainbow vacuum salesman and then he tried selling insurance, meanwhile collecting hundreds of “rejection letters” from other fruitless job searches. He also took a stab at acting, landing “non-speaking extra parts on SeaQuest and a Dolly Parton project that never made it to the networks.”

All along, Jay’s wife Debbie knew what a gift he had with words and encouraged him to get into freelancing. He decided that he liked writing better than being in front of the camera. He admits that initially, he didn’t treat writing like a real business. Nonetheless, it led to some interesting and lucrative assignments. His first published article was, “How to break into writing infomercials,” for editor John Clausen, who, Jay said, “saw something special in my writing.” Meeting John turned into friendship and led Jay to a job as managing editor for two bi-monthly journals geared toward writers, while also contributing to a variety of other publications from in-flight magazines to book and music reviews.

A self-professed “guy who can’t say ‘no’ to a job,” he took on a project with PricewaterhouseCoopers, largely because he was the only freelance writer they interviewed who said “yes” to their crazy timeframe. In four weeks, he learned their new budgeting software, wrote a user’s guide and a field guide and developed training for 150 employees. He also ended up teaching part of the course when an instructor became ill. He looks back fondly on the experience and the way this particular client treated him as one of their own, even though he was only there for a temporary assignment.

It was instrumental in his development as a writer: “I decided to change my focus from periodical writing to commercial,” he said. By the year 2000, Jay was back in the corporate world—a client lured him from freelancing into a marketing director’s position. Six months later, Jay said this company “imploded and I was going to be laid off. Marketing is always the first to go.”

He one-upped the crashing company by suffering two heart attacks. After surviving those traumas and then a bout with a rare and aggressive form of skin cancer in 2003, Jay found himself working another corporate job with a long commute. Again, it was Debbie who reminded him that he could have a future as a wordsmith. As it turned out, she was his biggest supporter. “Why don’t you quit and go back to writing?” she urged, presenting what she called “Jay’s Jubilee,” a realistic action plan for financing the initial start-up phase that seemed to make perfect sense. It seems this smart and savvy lady had given it some serious thought—she was so in tune with what she knew her husband needed.

Still, he took his quandary to his best friend, Scott Hitchcock, for advice. Scott is a Tampa Bay area leader for the C12 Group, a nationwide organization for Christian entrepreneurs and CEOs. “This job is affecting your health,” Scott pointed out. “And—you’re not using the talents and skills God gave you.” The next day, Jay turned in his resignation and gave his inner wordsmith a second chance. And this time around, at the insistence of Scott and his wife Terry, he set it up as a business and incorporated.

“I got into this because I like to write,” Jay claims, “not to run a business. Business has never been particularly interesting to me.” That said, this reluctant entrepreneur is forced to handle the not-so-creative aspects of accounting and making those sales calls, a necessary evil when running one’s own show. Fortunately, Jay belongs to the local chapter of the C12 Group. Through networking, he’s made valuable contacts with professionals in other fields, upon whose expertise he can draw and likewise share what he knows about communication and marketing. “We all work together to help grow the best businesses we can while integrating our faith,” he says.

One of the biggest challenges he faces is the limitation of time. In the freelance world, workloads ebb and flow. Managing deadlines for his clients and delivering the goods on schedule can put the office work on the back burner. “It’s hard to find time to do it all,” he says, mentioning that he just might have to consider hiring a partner to handle the business and sales end of it one of these days.

Much of Jay’s work comes from referrals by past and current clients, many of them fellow members in C12. These are clients who “really appreciate what I do for them,” Jay says, and send other prospective assignments his way. He has a three-prong approach to taking on new projects. First, he asks, is it going to be fun or interesting work? Second, is this potential client “good people?” And third, does the possibility exist for building a long-term, mutually beneficial working relationship? Only after those questions are answered does he tackle the next challenge: setting the fees for his work. It’s definitely not his favorite part of the job. Fees are tailored to the different needs of each client.

One of Jay’s friends describes his marketing strategy as simply his gift for bringing people together. Sometimes he is able to connect companies who could use each others’ services, but aren’t aware of the possibilities. “I like helping people meet their needs,” he says, “whether it’s in my writing, my business or through my faith.”

Indeed, his faith is a guiding principle in his life and in his work. “Whatever success I enjoy and this goes way beyond making a living, I attribute it all to Jesus,” he explains. “Without my Christian faith, I would be a very different writer—in fact, a very different man. While the work would still be enjoyable, it would lose the overall sense of fulfilling a Purpose beyond putting words on paper.”

There’s no such thing as a boring day in his line of work, he says. “All my clients are different and every project presents an opportunity to learn.” He’s starting to get into gadgets as a way to keep organized, but what he really is, he says, is “a pile person.” Projects are stacked on his desk and woe is the poor soul who attempts to “clean up” his office by disassembling them in the name of neatness.

“A lot of the writing process, for me, is very internal,” Jay explains. “I do a lot of thinking about what a client said, and what they need, and then I sit down to write.” Jay wants businesses to think of all the ways communication plays a vital role in a company’s success, including sales staff talking to customers, management and employees talking to each other, prospective consumers reading the brochures and websites. Then there are user guides or other product information, and investors scanning the annual report, he points out. It’s all communication and it’s all content—and it’s a very good reason to bring in a professional writer.

He’s got a winning outlook—this is the best job he’s ever had, he says. “It’s fun, it involves my faith, I learn about a wide range of subjects and meet the most interesting people…and I get paid.”

While Jay Winchester found his own way in the world as a writer, he also found a connection with his family: every time he sits down at the keyboard, he is making a living with his hands, just like them.

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