In 1998, brothers Shep and Ian Murray found themselves in jobs they wished they could leave. Shep, who was 27 at the time, worked for the Madison Avenue advertising firm Young & Rubicam. Ian, who was 23, worked nearby at a small public relations company.
During breaks from their offices, the two would meet up and commiserate. “We worked 20 blocks away from each other, and we met on 50th Street,” Shep said. “He was on 60th. I was on 40th. And we just talked about quitting every single day, but we just couldn’t figure out how to make a living doing something we loved.”
Eventually, the two settled on an idea. They would design and sell offbeat neckties that evoked the place where they had spent their childhood summers: Martha’s Vineyard. Shep explained their reasoning: “If a guy has to wear a tie, it may as well be one that he loves, that represents his passions, because a guy can’t really express himself wearing a suit.”
The two quit their jobs, a move they both agreed was a slightly jarring first step, and started selling their ties, brightly colored pastels dotted with Vineyard patterns, including whales, bluefish, and the island’s trademark street signs. Their enterprise, which they called Vineyard Vines, began primarily in their Jeep, which the brothers drove to stores around New England in the hopes of persuading a retailer to sell their clothing.
Soon enough, the business began to take off. Vineyard Vines now sells a wide array of apparel in over 600 retail locations throughout the United States, including Bloomingdale’s, Nordstrom, and Saks Fifth Avenue. The company also sells clothing overseas in Great Britain, Australia, and Greece.
Asked what advice they would give to young and aspiring businesspeople, Ian said: “Make sure they do it because they’re passionate about it. You shouldn’t start a company to go make money.” He added, “It’s got to be a lifestyle change. There’s nothing wrong with going out a starting a business that makes money, but if it’s the primary goal, I think it’s hard.”
Shep and Ian were two of several American entrepreneurs Slate interviewed for this Hive series, Invent Your Future. We wanted to determine if there was a secret to setting out and starting a successful business. In our talks with these businesspeople, we encountered a few counterintuitive revelations.
All of our interviewees insisted that working hard, of course, was important. But almost everyone we talked to agreed with Ian that a secret to success is to start a business because you’re passionate about it, not simply because you want to make money.
Like the Murrays, Alexa Hirschfeld and her brother James knew they weren’t a good fit for corporate America.
“I always sort of knew that I wasn’t going to work in an investment bank or a consulting firm,” says James, who is 25.
While he was a sophomore at Harvard, James wanted to organize a party for his friends to get together for his 21st birthday. He hoped to send out invitations for the party, but he didn’t know the addresses of many of his college buddies, and he found himself longing for a faster, easier way to send creative, elegant mailings.
So in 2008, James teamed up with his sister Alexa, now 27, to start Paperless Post, an online service that sends e-invitations modeled after high-end stationery. The company, which charges about $0.16 for each card users send, has grown at a stunning rate. The site, which now has two dozen employees, has sent out 45 million pieces of mail since it began.
The Hirschfelds said they were able to quiet skeptics who doubted that a pay model for online e-cards could work by offering a product that offered users unprecedented ways to put a personal touch on each note.
“I think what people like about it has been to give them tools that reflect who they are,” James said. “All emails look the same, and this is an opportunity for people to express themselves.”
I asked the two what they liked most about working for themselves at such young ages, and Alexa was quick to respond. “It is really fun,” she said, “because we can be creative and also be at work.”
What advice would she give to other young aspiring entrepreneurs?
“I would say, just do it,” she said of starting a business. “Just do the simplest version of it, and see if there’s an interest and if there’s a kernel of need out there.”
It’s not just twentysomethings who reboot their careers. Setting out on your own, of course, doesn’t always involve ditching a first job or launching a trendy Web startup from the dorm room. Taking a big business risk can often happen in the middle of a person’s life and career.
After working for a computer software company for 22 years, Tracey Getty and her husband decided they had to make a change. He worked for Hilton Hotels, and he was relocating constantly. The never-ending transience, Tracey said, took its toll on the couple.
“We were on the move forever,” she said. “Frankly, we got tired of moving.”
So in September of 1999, the couple purchased the Waybury Inn in Middlebury, Vt., and moved there. They renovated the 13-bedroom property, which had been in disrepair, and began taking in guests. Initially, Tracey said she and her husband were stunned at the work that running an inn required. “We both have worked hard in the corporate arena,” she said, “but we’ve never worked harder in our lives,” adding that the two often put in 80 and 90 hour workweeks to make sure the operation was running smoothly.
Despite the hard work, however, Tracey said the opportunity to run her own business has been worth the effort. There is “no boss, no corporate entity, no management to tell you what to do.” She added, “We really wanted to not have a corporate influence overshadowing what we did.”
And the Waybury Inn, with its rustic charm and highly personal service, is anything but corporate.
Tracey said many of the guests are regular visitors, and she has quickly become a part of their lives. “We know their dogs’ names, where they’re from, when they’re birthdays are,” she said. “And we make them cookies. It’s really rewarding.”
Like the Murrays and the Hirschfelds, Getty said the only way to succeed fully on your own in business is to love your work. And the recession hasn’t dampened their enthusiasm or their drive to improve their enterprises. If anything, it’s solidified their determination.
As Shep Murray explained to me: “I think basically the message that we can send is that the American Dream is still alive and well. There are plenty of opportunities out there. You just have to go out and make it for yourself.”
Slate’s Invent Your Future project is collecting your best real-world ideas about starting a business or reinventing a career. Share the best tip you got about starting your own business, the best advice for cobbling together gigs, the remarkable story of how you turned a hobby into a career. Read this introduction for more details and submit your story or tip below.