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Story & Photos by Ellen Porter

Not having chosen a career path in stenography or marketing because a good job should be a job doing something you like, are you becoming nervous, re-evaluating what a desirable resume could do for you? Are these the odds you face -- stone bored or dirt poor? We all think of it sometime... being our own boss. It’s a fanciful idea when you’re accustomed to spending your time half-heartedly behind counters at Starbucks stocking cups or ruining your clutch delivering pizzas in the Fan.

Thinking of the future can become a listless experience: toiling away for other people, being poor, and entering an already swelled academic jostling match for graduate schools to ride on the last coattail of student aid. All around me I see people I know trying to meld their skills and their heretofore unprofitable creative talents into a job, what we perceive as the ideal job --owning a business.

It is an uncertain game, and surely not for the faint of heart. Yet it is a manageable challenge, more manageable, I’d say, than facing years of the indigestible and routine work you might be doing now. It’s easy to be deterred by the statistics or, more practically, by the start-up costs. The drawbacks are many, yet the reward may be worth it. For many it is not the right choice. Those considering it need to explore themselves and their priorities. If you’ve been thinking about taking the plunge, feel encouraged. It seems we may be living in one of the riper cities. Richmond has been earning some accolades as of late. Entrepreneur magazine places it as one of the top 10 cities in the South for small businesses and Regional Financial Associates ranks Richmond as the second most cost-effective city for operating a business from the top 100 metro areas in the U.S.

I recently met Holly Edens, 28, when she decided to wait tables for a brief stint at the restaurant where I work. She laughed at the irony, as she had worked graveyard shifts at the same restaurant six years prior and thought she would never see herself there again. During her ensuing absence from Richmond, Edens had taken a tremulous path to owning, running, and finally, to selling her own business. Talking to her I’m more inclined to believe the business owned her.

Moving to San Francisco, Edens became an investor and partner with some close friends who had the opportunity to own and operate a new and used motorcycle parts shop, thoughtfully named "Lost Motor Functions." It was a deal she couldn’t pass up. She had originally agreed only to be a financial backer and with the sum of $9,000 from savings and family she proceeded to play the background role of friend and investor. A short one-and-a-half months into the venture, both partners abandoned her -- a woman without the immediate technical knowledge or the brawn -- leaving her with $1,000 a month rent and a lot of motorcycle parts. She certainly didn’t shrink from the challenge. For two years she sweat her life into it, facing obstacles that ran the gamut from klepto employees to shiny competitors only a few doors down. Finally she decided to sell. And sell she did, taking the money to travel around the country for almost a year visiting friends and family, until she swam full circle back into Richmond where she saved her money and has left again for the California coast. From what she knows, the four men who bought Lost Motor Functions are struggling more than she ever did and may not be able to remain open much longer.

I asked Edens if she would ever own a business again and she squawked at the idea. "When you own your own business, you think you’ll finally get to be the boss of yourself. Ha-Hah. Think again, the government is your new boss - taxes, permits, insurance, licensing... everyone wants to fuck you." After a moment or two, she softened, saying she has considered going into business again, but this time smarter. "I would own a band practice space or a recording studio where I primarily rent out to other people, something where the business runs itself and doesn’t steal your life."

Although most agree that experience is never exactly regrettable, it doesn’t have to be so obnoxious. Edens learned, reluctantly, about the problems in the byzantine structures of ownership and management. She was fortunate to have been so successful when she hadn’t prepared for it at all.

On the other hand, Dianne Roberts, the owner of fashionable City Shoes in Carytown, seems as if she has substantially prepared for the experience of entrepreneur. According to Roberts, "It never crossed my mind that I couldn’t do it." At 26, her confidence is well deserved. Business is better than ever, her store is celebrating a three-year anniversary, and plans for expansion are lurking in her shoeboxes. Fortunate to have a mentor in her mother who owned an antique and craft store, Roberts gained retail experience at an early age. Working at the store during high school and attending trade shows, she learned business lessons first hand. While a fashion design student at VCU, she dabbled in the world of waitressing and planned on going to New York City hoping to land a job with a designer. Her ample and distinct style is evident in the sublime settings and deliberate selection of shoes in her store.

Diane Roberts, 26, owns City Shoes in Carytown

While the rewards of starting a business are alluring, Roberts explains, it also requires commitment and devotion. "When I first started, I was totally unrealistic about how much time it would take and how much time I would be there," Roberts said. "I denied for a long time the commitment I had to make." Being interested in other ventures, she saw the shoe store as "a little side project." "After about a year," she elaborated, "I realized this was the key to getting somewhere in my life."

Another turning point for City Shoes came with a geographically tiny move in location. The store opened on Colonial Ave. (running adjacent to the Byrd Theatre), and I hesitate to confess I never had a chance to go there. Roberts acknowledges that business there was "okay, but never that great." She describes that period as very emotional and stressful. Wisely, Roberts seized the opportunity to relocate directly on Cary Street and, astonishingly, her business has literally tripled. The move wasn’t easy and Roberts is proud of her ingenuity, radically renovating an ancient, cinderblock typewriter repair shop into well-lit bastion of ladies footwear, all on a shoestring budget. "I got some really good deals," she said, adding that her father built the counters in the store.

Not only does the entrepreneur learn by necessity to be cost efficient, but she also learns her market. Targeting a specific woman, Roberts offers merchandise for clients with a more upscale and professional taste, as well as the cost-conscious college or high school student. "If I lose my focus, the customers won’t get it," Roberts says. While her clients appreciate shoes that are different, she notes that "It’s easy to go in the wrong direction."

Caution is healthy, but I don’t think Dianne Roberts has anything to worry about. For those interested in opening a business, she encourages prospective entrepreneurs to go for the risk. "The only way to find success is to gamble. It’s a risk, but focus on the prize." As for herself, opening a shoe store at the age of 23 was "way better than anything else I could be doing right now at my age. It’s been difficult at times, but overall it was the right decision to make."

Similar to Roberts, Greg Stephan has found himself breathing easier after a precipitous beginning. Stephan owns Soundhole, a music store with two locations, one in Southside across from Chesterfield Towne Center and another in the West End, curiously close to Peaches. These days Stephan takes time off every now and then and he doesn’t wake up at night wondering if his checks cleared or frightened that the Postal Service might have become more efficient. It wasn’t always so.

Like Roberts, Stephan’s father owned a store, the very store Stephan bought. But no scoffing, it was hardly a family give away. Business for his father had been so-so and finally he had decided to sell. Stephan had been out of school for awhile without any pressing plans. He thought he might go back to college and, "find something to do with myself." It was good timing. Stephan and his father arranged a sale through a lawyer, with loan payments and interest. He has almost paid off the loan now (never missed a payment ), and purchased everything, from the inventory and registers to the name of the business itself. "I didn’t want something for nothing. With my Dad closing the store, it benefited him and it benefited me." The $30,000 loan helped Stephan run the store for about six months before he moved the location, changed the name, and redesigned the store’s appeal.

Starting with an abysmal 200 CDs, he learned the art of floating checks, never knowing if at any given moment enough money would come in. The first summer was hard. He paid himself only $5,000 for an entire year. "We survived through credit cards and student loans. We kept our expenses really low. I did nothing that year. I put all the money back into the business, buying new CDs or vinyl." Deservedly, his instincts prevailed. He chose to direct his merchandise to the more obscure, favoring heavy metal and punk rock. He ordered things without a tangible clue anyone would buy them. Fortunately now, the kids from surrounding high schools go there to find out what’s new. It takes an acute observer to pick up on trends in such a trendy market as alternative music, but Stephan has proved to be adept. The fact that his business thrives a Stone-Temple-Pilot’s throw from larger chain music stores is enlightening enough. His strengths are not an overwhelming selection or even discount prices, but rather a faithful customer base and his own edgy personality.

Both Stephan and Roberts thought quickly enough to seize an opportunity when it arose. But sometimes the opportunity is made by the entrepreneurs themselves. Brian Landis and Tom Sullivan are both local musicians, (in the bands More Fire For Burning People and Brenda, respectively), and like most of us here in Richmond they hope for a healthier, more rewarding music scene. They would like to contribute by giving local and indie bands a venue to sell their music. At 21, Sullivan has already started his own label, RUIDO, releasing some 12 inches with a full length CD in the near future. Though not necessarily a financially rewarding endeavor, it has helped prepare Sullivan for the skills he is using now.

With equal and negligible sums of money (only $2,500 each), Landis and Sullivan set out to open a record store, using the bulk of their money to build an inventory of vinyl and pay for the necessary business licenses. They searched for rents and viable partners, exploring spaces around Grace Street and even contemplated some co-op situations. Finally they have the good fortune to be included in a burst of small business revitalizing the corridor of Cary Street behind the VCU dorms. It was here they met a sculptor/landlord who was willing to give them a reduced rent in exchange for a place to vend his own artistic creations; furniture curiously formed from car parts. The store promises to be eclectic. Landis and Sullivan plan to open in a month or so alongside the enigmatic vintage store Ethel and down the block from the always delightful 821 Bakery Cafe. Wisely chosen, for with the completion of the Engineering School at VCU, this area will undoubtedly be trafficked.

Brian Landis and Tom Sullivan, planning a record store near VCU.

Right now, Sullivan is working as a cook and Landis works at a copy shop. They don’t plan on giving up their jobs, but will try to work the many hours at the store around them. In the meantime Sullivan learns to install toilets, Landis knocks down walls. They show me their store, pointing to corners full of makeshift shelving and new light fixtures. I smile along with them, hardly aware of what they really have in mind– loungy, creative, coffee and car parts. This will be one piece of Richmond that is innovative and young. They will see what works.

Interestingly enough, no one I spoke to felt they were making permanent decisions for their lives. My father had the same job for 50 years. It is this understanding of the marketplace and our own skills to be evolving and adaptable that perhaps allows us to take risks and look ahead. The tags of Generation X and Slacker have been resented from the beginning. If anything, we toil at (seemingly) unrewarding tasks: college degrees in philosophy and religion, basements full of sculpture, and volunteer magazines.

When I look around the city at the places I love: Oregon Hill, Grace Street, Jackson Ward, Church Hill, and the Fan– I see a lot of vacancies. Places where rents are low, and renovation is to be had. To witness the newer generations beginning to stamp out their likenesses in the public of this city is hopeful and refreshing. It will still be awhile before the banks or the insurance companies begin to woo “Generation X.” So far only the advertisers of products like flavored ice tea have recognized us. But we are, of course, like other generations, best suited to recognize and meet our own needs and resent or learn from those that precede us.

Trisha Nguyen also contributed to this article.