3456 7:30 Throwback Thursday

TBT: Urban Hiker Leads Tours in San Francisco

In this week's Throwback Thursday segment, we hear from a woman with two successful side hustles. Adapting to a changing world, she's able to thrive even in the midst of unexpected challenges.

7:30

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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.

Read the full transcript

This transcript was generated from the episode audio and may contain minor errors.

[Music]

Urban Hiker leads tours in San Francisco. Hey friends, what's up? Welcome back to Side Hustle School. Chris Guillebeau, your host. Welcome as well to Throwback Thursday, also known as Where Are They Now?

In this segment, we take a look at someone whose story has evolved since we first featured them. And today we're gonna go all the way back to one of the very early episodes of the show. I think she was in, I don't know, episode 158, I believe, which is way back in 2017. Her name is Alexandra Kinan. She has a couple of different businesses.

She is a multi-hustle side hustler. And one of them is an urban hiking business in San Francisco. So she's gonna talk about that. She might also mention her other business as well. We've known Alexandra for a while and she's very resourceful.

But coming up with ideas and also executing on them, which are of course two essential skills. All right, without further ado, I'm gonna pass the mic to Alexandra. I'll be back at the end with a few words of wrap up. [Music]

My name is Alexandra Kinan and I live in San Francisco, California. My side hustle is called Urban Hiker San Francisco.

And I was featured all the way back on episode 158. An episode called Urban Hiker climbs to steep success in San Francisco. It's an urban hiking tour business where we explore the stairways, hills and hiking trails of San Francisco. And in our city, we've got 70 miles of trails. We host small groups, private groups, corporate groups on tours that last two to three hours, four to five miles.

I got started with my side hustle following Chris Gilbo's ideas from his book, The $100 Startup. So 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've registered my business with the city, joined San Francisco's Visitors Bureau and got insurance. So that was a tiny bit later. And I got started also by doing tours for friends or family to get TripAdvisor reviews.

So 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 Word Smithy, which is really cool. 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 writing guidebooks.

So much has happened since back in episode 158. Personally, on a personal note, I had a baby who's now gonna be two on the 4th of July. So he has a very exciting firework filled birthday. Professionally, a lot has changed too. So I still have that solid paycheck with my day job.

But for the side hustle for Urban Hiker SF, as I got closer to having the baby, I realized there would be a time probably before and definitely after where I couldn't guide all the heights myself 'cause I would be recovering. So I made sure I had other guides who 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 when we all need to be working at once. But having guides has been really neat because it's made me feel like I have more of a passive income stream.

So that's been great. Still bringing in some money with even less effort. So that's great. Another thing I am happy about is that I finally paid for a professional website and you can check that out at urbanhikersf.com. A third piece of news, going back to 2016, I wrote a hiking guidebook called Urban Trails San Francisco, which has now sold close to 11,000 copies.

And now this May 1st, my second hiking guidebook called Urban Trails East Bay is coming out. On a less positive note, because I was so focused on my book last year in 2018 and 19, I sadly didn't focus as much on the tour side of my business and it didn't do as well as it did in 2017. But now I have a renewed focus on my tour business this year. I've got a bunch of corporate events planned for May, June and July, but I also have some exciting challenges to talk about too. So one is that a client has asked me to run a 150 person event for them in July with a hike in a book cruise on the San Francisco Bay.

My largest tour so far has been 45 people. So 100 less than what I'm asked to do now. So this is gonna be a stretch, but an exciting one. If anyone wants to follow in my footsteps, I would say, you know, do a lot of research. Oh, maybe not too much research.

You gotta get started too, but kind of get a lay at the land and research the other corporate business in your area. Start to understand the landscape so you could see where you might fit in. Another thing it's kind of general that applies to anyone, but it's really, really applies to that 150 person event that I'm planning in July. And that is to know your strengths. So I'm the kind of person who's really good with big ideas.

I'm less good with details. So for my upcoming 150 person event, I'm working with a partner, Debra from Tam Hiking Tours, which is another local tour company. She is fantastic with details and we're gonna partner up for the event together. And with her help, I believe everything will go smoothly. So, you know, you can't possibly do everything yourself and be good at everything.

So don't be afraid to bring on partners if you recognize that you need someone else to compliment your strengths. [Music]

Alexandra, thank you so much. I always enjoy your updates. And I was just taking a peek at Alex's website, urbanhikersf.com, urbanhikersf.com. She's been going for as long as we've been going, pretty much nine years, maybe even longer for her, but this business is still taking people on tours.

You can also check out gifts. She's got some resources, learn a little bit more about the business. What's different about Urban Hiker? I was just reading the frequently asked questions. And in fact, what's different is they are the only urban hiking tour company in San Francisco.

So that's some pretty good differentiation there. You can also learn more about her book on that same website, urbanhikersf.com. Also head to sidehustleschool.com if you'd like to access any or all of the previous episodes of the podcast, 3400 plus all sorts of case studies, tips, ideas, questions, answers, and more. And of course new episodes come out every day, seven days a week, always free. My name's Chris Guillebeau.

You're listening to "Side Hustle School." [Music]

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