How I Built a Lifestyle Business I Love
BY Jeff Haden
Most people wish they could say they do what they love. Here's how one business owner actually made it happen.
Like most platitudes, “do what you love” rings a little hollow… but not for everyone.
Take Lauren Hefferon. She loves bicycles: from an early age she loved the outdoors, loved to ride, and loved cycling on an athletic and a personal level.
“Starting when I was a kid,” she says, “I knew I didn’t just want to have time to ride. I wanted cycling to be at the center of whatever I did in my life.” Today Lauren owns Ciclismo Classico, an award-winning cycling tour company based in Boston that has won Outside magazine and National Geographic trip-of-the-year awards.
Lauren does what she loves. How? By design.
“To me, getting away is the dream,” Lauren says. “Life is not about having stuff, it’s about having experiences. Even in high school I thought the definition of awesome was to ride my bike, take hundreds of pictures, enjoy amazing scenery, and eat amazing food. I decided to design my life so I could always have those experiences and share them with others.”
Like how she chose a college. “My dad wanted me to go to Cornell,” she says. “It’s a terrific school, but what sold me was how great the surrounding area is for cycling. Cycling was like a stake in the ground that kept me engaged in school. If I had gone to college in, say, New York City, something would have been missing and I wouldn’t have been as engaged.”
While in college she led informal bicycle trips, and when she graduated she wasn’t sure what to do next. “I had studied anthropology,” she says, “and I loved culture and travel, so I went off to study in Italy. It goes without saying that Italy is an amazing place to ride. While I was there I looked for ways to take my love of cycling and make a life out of it. I thought about opening a bike shop, but I didn’t want to sell things. I really wanted to ride and travel.”
So she started working for a small cycling tour operator in 1985, leading trips from Rome to Paris and Rome to London. “Those trips are about as challenging as it gets for a tour leader,” she says, “and yet I was still totally stoked. So I came back to the States and started my own company.”
At the time cycling tours tended to focus on point-to-point excursions. Few, if any, tour operators offered specialized destinations and experiences. Lauren decided that with her anthropology background and her love of experiential learning, a bicycle tour wouldn’t have to only involve riding from place to place with a lunch strapped to your back.
“I love to learn,” she says, “and I thought education would be a cool component. So I started developing the formula: Cycling clinics, Italian lessons, cooking lessons, embracing the history and culture… really turning a cycling tour into more than just a bike ride. I decided my secret sauce was providing bicycle tours for the culturally curious. ”
She ran her first ad, booked her first clients, and led her first tours as a one-woman enterprise. To her surprise, the sales process came easily. “I love to talk about our tours,” she said. “I don’t see it as a ‘sales process.’ When you love something, selling is easy: Just talk about what you love.”
Over the years her business has changed. “When I started we took a more basic approach, using 2-star hotels, etc. In the 1990s people wanted a 5-star experience, so we created deluxe tours to satisfy the more affluent clientele. Recently we’ve shifted back, at least in part, taking a ‘more miles for less’ approach because that's what many clients want. But we still are known for our huge culinary focus and advanced riding experiences.”
She has adapted her role in the business to ensure cycling remains central in her life. “A business is like a child,” she says. “It should grow up and be the person it can be. You don’t need to mother it forever. Besides, the only person who ever succeeds fully is a musician: They get to market their music and play their music. The rest of us don’t get to do as much of what we love as we become more successful.
That’s always the challenge, but it’s definitely a challenge worth tackling.”
JEFF HADEN learned much of what he knows about business and technology as he worked his way up in the manufacturing industry. Everything else he picks up from ghostwriting books for some of the smartest leaders he knows in business. @jeff_haden