A friend took me on my first urban hike years ago. We were walking across San Francisco and instead of taking me the most direct way from point A to B, he took me through parks, alleyways, hills, and other secret places. Since then, I’ve been hooked on exploring the city—finding the fun hidden spots that most people don’t know.
How did you make the transition to becoming a tour guide?
When I became a guide, I had no previous guiding experience, so I just threw myself into the experience headfirst. That said, I did have a few things going for me. I had a good amount of public speaking experience and I loved meeting new people. As for the tours, I created them myself, so I was more familiar with the routes and history than anyone else.
What does a typical day look like for you?
Believe it or not, I’m a marketing consultant for part of the week. I used to work at Google and still love doing marketing for tech companies. I work with an agency called Wordsmithie and work with them about 10 to 20 hours a week.
On most afternoons and on weekends, I’m guiding tours, working on partnerships with other groups and companies, and finding new ways to grow my hiking business.
Lastly, I’m writing a book on 50+ hikes that you can do in San Francisco, so I also spend part of my week either exploring the city or writing about the hikes I do.
I’d say my style is informative, but friendly. I try to teach my hikers a lot on my tours, but I also want to be approachable and develop a true connection with them. When someone comes back on a tour after a year or two, I normally remember their name, their face, or both.
What is the best part of your job?
I have two favorite parts of my job. First, there’s meeting people from all over the world—so far, I’ve hiked with about 2,000 people from more than 20 countries. Next, there’s getting paid to exercise and play outside. I love that my office is in the great outdoors.
What’s the most bizarre experience you’ve had on a guided tour?
This one actually happened in May—I was hiking with a group of about 10 people. We were about to go on a dirt hiking trail up to the Twin Peaks scenic overlook. As soon as we got on the trail, however, we saw there was a belligerent homeless person in our path. He was flailing his arms wildly and certainly wasn’t getting out of the way, so we turned around and found another trail to the top of the hill. I hope that doesn’t scare anyone off—that only happened once!
What I love about urban hiking (as compared with hikes out in nature) is the diversity of sights that you can take in in a single hike. In San Francisco, in one moment, I could be on a hiking trail. Then I could be exploring a large-scale artwork. Next, I could be sliding down a slide in a park. And then moments later, I could be taking in a great view of the skyline.
Ever had any odd requests from clients?
Nothing too odd – just hikers who want to do more than we can do in one tour. I’ve had a few hikers ask for half-marathon hikes.
Every job has its ups and downs. Are there any aspects of your job that you don’t like or aren’t that keen on?
I don’t love doing the back-office functions of my business. I do all my own accounting, but honestly, I’d rather be out on the trails.
A guide helps you unlock experiences that you couldn’t unlock yourself. For example, my tours have about 49 different turns on them. It would take someone a long time to figure out such a complicated route on their own and learn all the history that we cover in a tour. In addition, there is great energy that comes from a group situation. You meet new people and have a more fulfilling and memorable experience than if you were on your own.
Tell us something about urban hiking that only a guide would know.
There’s always something else to explore. A lot of people think they’ve seen all there is to see where they live. When I take San Franciscans on tours, they don’t necessarily think they’re going to see anything new. However, usually 80 to 100% of the sights that we visit are completely unknown to them. I tell people that however long you’ve been somewhere, you can still find new things to do and see.
Have you got any tips for people who are interested in booking a guide like yourself, but aren’t too sure what to look for?
If you’re looking for a guide, check out the way they describe the tours, check out the photos on their website, and make sure to read reviews on the tour to learn more about what they have to offer.