Chapter Five: The Entrepreneur
“When I was just getting started and had little professional experience planning events, I talked to prospective clients about every party and wedding that I had ever been to as if I had planned them single-handedly. I tried to remember everything about these events (name of the band, construction of the centerpieces, etc.) so I could speak about them with a fair amount of confidence. I would also take notes on the events that I attended and follow up with vendors that I saw there so that I could use these events as jumping off points in my own career.” -Lindsay, 29, Event Planner
Who wouldn’t envy the entrepreneur, a person with the courage to stand on a high board and dive into the pool below without a moment’s hesitation? Starting a business in today’s world is never easy, and successful entrepreneurs like Lindsay have to have the smarts – and the guts – to make it happen despite the obstacles of inexperience, money, and competition. The number of Americans taking their careers and their futures into their own hands, though, is currently higher than at any time in the last decade. As I write this book, more than 23 million people (or almost 12% of all Americans) are in the process of starting a new business or are managing one that is less than four years old.
Though entrepreneurs come in all shapes and sizes, they are united by their ability to push past fear and take leaps of faith in the pursuit of a vision. “A true entrepreneur isn’t deterred by risks, but stimulated by them,” says Lindsay, 29, the owner of Lindsay Landman Events. “There is no ceiling for us, because we push the envelope every time to achieve something that hasn’t been done before.” Julia, 30, the co-owner of bridal boutique Hitched, agrees. “It’s a rush to chart unknown territory and create something tangible of which we can be proud. Every day presents a new challenge, and every day has small, and sometimes even big, rewards.”
The risk-taking nature of the entrepreneur, however, is accompanied by an ability to observe the world around him and uncover needs that he can meet. “I’m always on the lookout for annoying, everyday problems that are just aching for solutions,” says Brian, 32, an inventor. Many of them can trace the origins of this talent to their childhoods. “When I was growing up, tourists used to come out to our area to pick apples,” says Kori, 32, the owner of Kori Elizabeth Events. “I was just in second grade, but I saw an opportunity. I built a lemonade stand – not just any stand but a yellow one with brightly-striped curtains. Under my supervision, my friends sold drinks, cookies, and candy to the hungry apple-pickers.”
At the same time, though, the smartest entrepreneurs accept that they don’t know everything, especially when just starting out. They are skilled in seeking out expertise and using the learnings and opinions of others to their own advantage. “I’ve worked with reputable trainers from all over the world,” says Lisa, 39, the owner of Studio Elle Pilates. “I aim to get to them before they retire so that I can soak up all their knowledge.” Steve, 36, the founder of the popular Micropersuasion.com blog, uses an RSS reader to keep tabs on what dozens of marketing and business experts are saying every day. “I have to be an information junkie,” he says. “To do my job well, I always need to have a sense of what others consider important, and what I should be blogging about.”
The entrepreneurs I met were full of energy and even somewhat frenetic, which is probably an evolutionary response to the active, harried lifestyle they must lead. “One moment I’ll be working with a customer and the next I’ll be rushing to a strategy meeting with my partner,” says Carin, 31, Julia’s co-owner in Hitched. “There’s never a dull moment and we are busy from morning until night…and then some.” Most of them wouldn’t trade the craziness for anything, though – they aren’t the type of people to be happy sitting at a desk from 9-5 or dealing with the bureaucracy or routine of traditional business environments. “When I put in a good day’s work, I get to see the results immediately,” says Beth, 33, a professional organizer. “I set my own hours in order to be the most effective, instead of languishing in an office in Corporate America on someone else’s watch.” Will, 30, the founder of sports blog Deadspin.com, is right there with her. “Business meetings, and other such things, are the antithesis of productivity,” he says. “I love being able to work when I want, the way I want.”
The endless amount of difficult tasks involved in launching a new company – from drafting a business plan and securing financing to attracting customers and marketing your offering – require an upbeat, optimistic outlook and a streak of resourcefulness. “Inevitably, your plans won’t cover everything,” says Terry, 35, who had to open his bed and breakfast, ArtistsInnResidence, a year late after unforeseen circumstances delayed the renovation. “You have to trust that you’ll find a way to make it happen, even in the face of big setbacks.” And whether her business is still in the incubation stage or is fully hatched, the entrepreneur never stops coming up with new ideas. “I try to keep myself from thinking about product launches and feature articles when I’m enjoying dinner with my girlfriend, but I often find my personal to-do-list popping into my head at the most inappropriate of times,” says Jonah, 24, the owner of Rivalfish.com, an online sports apparel business.
As you can imagine, most entrepreneurs encounter their share of naysayers. “When I first started out, a business coach told me I was making the worst decision focusing on technology marketing,” says Alyah, 30, the owner of the Internet-based marketing firm ActiveNation.com. “Thank god I didn’t listen to him, because this niche has actually been a major reason for our success. It makes me laugh every time I remember this guy telling me how I was going to fail.” Jenna, 25, the owner and president of Model Challenge USA, had a similar experience during her firm’s infancy. “There were a lot of venue owners who didn’t take us seriously in the beginning,” she says. “I love getting phone calls from owners who hung up on us a few years ago. Now that we’ve made a name for ourselves, they want in.” Entrepreneurs who don’t have a thick skin have to grow one quickly, for if they let difficult people, including clients, stand in their way, they won’t last very long. “I’ve had not to take what clients say personally,” says Gina, the owner of It’s An Organized Life. “Some people question me through the whole process, as if they don’t believe what I’m telling them. I have to remember that it’s not about me, and that I can only help those who want to be helped.”
But entrepreneurs, incredible as they may be, aren’t perfect. They do have the tendency to jump into situations without thinking them through, and to skip over critical details as they struggle to move a business forward. “Back in high school, I had a crush on this guy, and so I decided to plan this huge Sadie Hawkins dance just so I had an excuse to ask him on a date!” says Lindsay. Lisa shares a story about a time when a situation at her fitness center got too hot to handle. “I had to take some time off after 9/11, but one of the teachers who covered for me was mediocre and didn’t bother to charge anyone,” she says. “My clients held on and waited for me to come back, but they weren’t happy. I almost went out of business.” Fortunately, though, the best entrepreneurs usually land on their feet. “It was out of the ordinary to start a business in which we had no experience,” says Julia. “But by taking our time and doing significant research, we were able to insert ourselves into the market.”
Entrepreneurs start businesses that do just about everything. If you want to launch a firm that produces entertainment for goldfish and you are committed enough, there’s probably a market out there for you. In this chapter, however, we’ll explore the entrepreneurial careers that my survey participants found most attractive – including bed and breakfast innkeeper, blogger, boutique owner, event planner, health club owner, internet-based business owner, inventor, pet sitter, and professional organizer. You’ll learn what each job entails, as well as what you need to do to set up that type of business.
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