Lifestyle Home Businesses that Actually Work

When you think of the ideal life, it’d most likely include something out of a Jimmy Buffet song: tropical islands, soothing tunes and margaritas, perhaps. And when you think of the ideal life as an entrepreneur or businessperson, you probably dream of simply being able to work at home. Well, combine the two ideals and you get TropiCast Media and Entertainment, our 2009 winner in the Home-Based 100 Most Slacker-Friendly category.

Creator James Jowsey actually used to play in a Jimmy Buffett cover band, Pirate Dreams, and was inspired by the music and island lifestyle to create his Angola, New York, company, which is a network of podcasts, streaming radio and video, news feeds and discussion forums devoted to fans of Trop Rock.

Now, you may be asking what the heck is Trop Rock? The term has yet to be entered into Webster’s Dictionary, however, Jowsey describes it as a genre of music that’s rooted in stories of tropical islands, sun-soaked beaches, string bikinis and the search for the perfect boat drink. Its fans are synonymous with the “Parrot Heads” that follow Jimmy Buffett–“anyone who has ever sat in their backyard with a string of tiki lights and a rum drink and imagined themselves on a deserted stretch of beach, soaking up the sun,” he adds. “[Our market] is definitely a state of mind or lifestyle as opposed to age groups and buying patterns.”

For Jowsey and his bandmates, Pirate Dreams and TropiCast started out simply as enjoyable pastimes (obviously!), but they quickly saw the potential when responses came pouring in following their first podcasts in 2006. “At the time, there didn’t seem to be a cohesive, organized outlet for these [musicians] and fans to connect on a national level,” Jowsey explains. “Hundreds of songwriters, thousands of listening hours, more than 50 episodes and hundreds of thousands of downloads later, TropiCast [is covering] all aspects of the Trop Rock genre.”

While the ability to work at home fits perfectly with the tone of Jowsey’s company, it’s not just a day lounging around. He devotes about eight hours a day to the company—that’s in addition to his full-time job as a vocational trainer for developmentally disabled adults.

In the early morning and late night hours, he and his one work-at-home staffer are plugging away: booking interviews for shows, writing and rehearsing, social networking, searching for partnerships, communicating with members, and posting news and events. Jowsey isn’t complaining by any means, though. “Most of what we do takes place sitting at the tiki bar discussing ideas and strategies, recording broadcasts and such,” he says nonchalantly. “This is the perfect job.”

COZY AND CONVENIENT

Courtney Young loves the ability to work at home, too. But she fell into her home-based business a little differently than Jowsey. Although she’d been interested and freelancing in the voiceover services market for 15 years, Spokesgoddess Productions, the 2009 Runner Up in the Most Slacker-Friendly category, was just a side business to her career in radio. But, as businesses do these days, the radio station downsized, opening the door for Young to work at home and put an increased focus on her voiceover work.

Because she’s also a full-time mom to a toddler, Young only spends a couple hours a day on Spokesgoddess. However, when her son enters daycare, she’ll be able to dedicate more time to her services, which companies use for applications like radio and TV ads, web videos and e-Learning courses. Young says there’s more than enough work out there to support a full-time enterprise, pointing to her client Tyco, which alone has more than 180,000 online courses in its database. However, she says “even when I have more time to dedicate to my business, I don’t foresee working at my desk for eight hours.”

The ability to work at home “works well for me,” Young says, adding that most of her work is web- and email-based. “I can really choose how busy I want to be and decide when I want to perform the work that does come in. I get to take two hours and go to the beach if I want and it’s a slow day.”

Despite how it may seem, entrepreneurs who work at home truly do work hard—just maybe from the comfort of their favorite tiki bar or a blanket on the beach. Entrepreneurship may not be a cheeseburger in paradise, but it doesn’t have to be an 8-to-5 in a cubical either. Says Jowsey, “[It’s] taking what you love and figuring out a way to make a living doing it.”