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TBT: Urban Hiker Leads Tours in San Francisco
Welcome to Throwback Thursday / "Where are they now?" where we take an in-depth look at someone whose story has evolved considerably since we first featured them.
Today, in our latest feature, we'll hear from Alexandra Kenin, who owns an urban hiking business in San Francisco. Like many of us, she's experienced massive challenges along the way—but she's also been able to adapt.
My name is Alexandra Kenin and I live in San Francisco, California. My side hustle is called Urban Hikers San Francisco, and I was featured all the way back on episode 158—an episode called Urban Hiker Climbs the Steep Success in San Francisco.
It's an urban hiking tour business where we explore the stairways, hills, and hiking trails of San Francisco. In our city, we've got 70 miles of trails. We host small groups, private groups, and corporate groups on tours that last two to three hours and four to five miles.
I got started with my side hustle following Chris Guillebeau's ideas from his book, The $100 Startup. For very little money, I bought a domain, created a website with Wix, and made a free profile on TripAdvisor so that people could find my business. I registered my business with the city, joined San Francisco's visitors bureau, and got insurance. I also got started by doing tours for friends and family to get TripAdvisor reviews. Between all that and doing some search engine optimization work on my website, people started finding my business on their own.
I have a job at a company called Wordsmithy where I get to do writing and marketing communications work for companies like Google and other tech companies. I do that 20 or more hours a week, and the rest of the week I have for my side hustle—whether that's doing tours, planning tours, or working on guidebooks.
So much has happened since episode 158. On a personal note, I had a baby who's now going to be two on the Fourth of July. Professionally, a lot of change too. I still have that solid paycheck with my day job.
But for Urban Hikers SF—as I got closer to having the baby, I realized there would be a time before and definitely after where I couldn't guide all the hikes myself. So I made sure that other guides could do my job. And now, even two years later, my guides are still running most of our tours. I pitch in occasionally when all my guides are busy or if there's a large corporate group. Having guides has been really neat because it's made me feel like I have more of a passive income stream—still bringing in money with even less effort.
Another piece of news: I finally paid for a professional website. You can check that out at UrbanHikersSF.com.
Going back to 2016, I wrote a hiking guidebook called Urban Trails San Francisco, which has now sold close to eleven thousand copies. And now my second hiking guidebook, Urban Trails East Bay, is coming out.
On a less positive note—because I was so focused on my book last year, I sadly didn't focus as much on the tour side of my business, and it didn't do as well. But now I have a renewed focus, with a bunch of corporate events planned.
To the point of this podcast—it's essential to have multiple income streams in today's world. I know people who are fully running core businesses and they are devastated, their income is zero. But I don't have to be in that situation, and I'm very thankful I have diversified income streams.
One exciting challenge ahead: a client has asked me to run a 150-person event with a hike and a boat cruise on the San Francisco Bay. My largest tour so far has been 45 people. So this is going to be a stretch, but an exciting one.
If anyone wants to follow in my footsteps: do a lot of research, but not too much—you've got to get started too. Research other tour businesses in your area and understand the landscape so you can see where you might fit in. And know your strengths. You can't possibly do everything yourself, so don't be afraid to bring on partners when you need someone to complement your skills.
Early on, Alex recognized she shouldn't be leading all the tours herself—and that smart move is now paying dividends as near-passive income. Her book Urban Trails East Bay is out now. Learn more at urbanhikerssf.com.
