How This Entrepreneur Turned His Love of Backpacking into a Full-Time Gig

How This Entrepreneur Turned His Love of Backpacking into a Full-Time Gig

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Advertiser & Editorial Disclosure

Steve Silberberg is living the dream. He left a high-stress tech job to start a company that taps into one of his passions – backpacking. Silberberg’s company, Fitpacking, takes people on backpacking adventures that help them get fit and lose fat. With trip destinations like Crater Lake, the Grand Canyon, and Joshua Tree, the company is thriving in its 12th year of business.

“Maybe Life Isn’t Infinite”

I have a master’s degree from M.I.T. and had worked in technology for many years. I had been at an investment firm doing software contracting for about 15 years. As I was getting into my 40s, I started realizing that maybe life isn’t infinite. I came in every day to a high-stress position wanting to stick a fork in my head. I thought maybe there is something else out there for me that would be more self-indulgent and make my life more enjoyable.

When I worked at the investment firm, my preferred vacation was backpacking. When I came back, I was kind of stress-free, I found that my clothes fit better, and I weighed a little bit less. I thought, “I bet there are other people who would want to do such a thing and use it as a motivation to jump-start their fitness level.” I didn’t know if it would work, so I put out some feelers and had a test trip where I had people come along and note their body composition metrics to see if hiking did affect body composition. It turns out it did.

The company I worked for was very gracious in letting me stay at their company for about a year or so while I was transitioning over to start my own business.

Financing the Business

The position I had at the investment firm was pretty lucrative, so I had saved up a certain amount of money and funded the business myself. At first, I was using personal credit cards for the business. I’m someone who doesn’t believe in paying debt service, though. What I was doing was making sure to allocate enough to pay my credit card off the next cycle. I’ve considered business loans, but I didn’t feel that I had a track record enough to secure a loan, and then I was afraid of servicing that debt. When I pay vendors and suppliers, I pay them outright.

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There are some people with whom I barter services. For example, on some trips we need transportation from a hotel to a remote wilderness trailhead, and then we need to be picked up 50 miles down the trail. People will join us on trips for a discounted rate in exchange for providing transportation.

December, January, and February is our slow season. However, that doesn’t mean the bills don’t keep coming in. So, what we do is run an annual sale at the end of the year to boost cash flow to make sure we can make it through the lean months. Then, during the rest of the year, we have a pretty constant flow of income.

Business Challenges and Rewards

Getting the word out and marketing is the most challenging thing about running the business. I’m not a natural marketer, so that’s the thing we constantly struggle with – letting people know that this is an option and getting the company’s name and services in front of them so that they know that we provide this service.

The most rewarding thing about this business is it’s very self-indulgent. I’ve always loved the outdoors and backpacking. There’s something really great about waking up in the Grand Canyon several days in a row and enjoying the big skies and the dry air. We’re going to Yellowstone and, as you can imagine, that has a different kind of beauty with thundering rivers, large trees, and mountain ranges.

Lessons Learned

Probably the biggest mistake I made was not having enough money saved up to float the business longer. I didn’t really anticipate the down season. I have had to, on occasion, go back and pick up a software contract in the off-season to keep cash flow going at times.

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One of the smartest things we’ve done is set up an aggressive loyalty program where people can earn credits towards every trip for as much as $700 off of a trip. Every time you go on a trip, you earn $100 off towards your next trip. It tends to bring in a lot of the same people. When you’re backpacking, it’s a social thing as well. You’re kind of creating a family. People keep coming back, and I think that has contributed to our success.

Advice to New Entrepreneurs

Make sure money is coming in. Make sure it’s profitable. If you have no money coming in, you have no business, unless you want to drain your savings and sell your house and assets and mortgage your children’s future. But, as long as you have money coming in, you can figure out all the rest. You’ll make mistakes, but you can overcome them. You’re driven, you’re an entrepreneur, you can figure this out.

The Future of Fitpacking

The business is small. It’s me, a couple of assistants, and about a dozen guides. I would like, within the next year, for the business to run without me present. Right now, it can run for a couple of months without me, but it’s still not completely self-sustaining. That’s my biggest goal. I think it’s attainable by 2018.

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About the Author — Ashley Sweren is a freelance marketing writer and editor. She owns her own small business, Firework Writing (http://www.fireworkwritingonline.com/), located in San Jose, California.

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