tour guide

Today, I have a very unique side hustle interview with Alexandra Kenin of Urban Hiker SF.

She started a successful side hustle as a tour guide and now earns around $2,000 to $8,000 per month from it. That’s an awesome income for a side hustle.

This can be a great side hustle if you love traveling or you have some extra time on hand.

How You can Earn While You Travel as a Tour Guide

Please tell us about yourself and your background.

I’m Alexandra Kenin and I live in San Francisco. For work, I’m an employee of Wordsmithie, a content and design agency. I also run a tour company called Urban Hiker SF that helps people explore the stairways, hills, and hiking trails of San Francisco.

Before I started working at Wordsmithie and creating my tour business, I worked at Google as a product marketing manager. Working at Google was wonderful in many ways, but it required commuting up to 1 ½ hours each way to/from work. It was also a large company, and I felt like I couldn’t see the impact I was having on people’s lives (if any).

With Urban Hiker SF, I get to show people around San Francisco and have a lasting impact on their impressions of the city. It gives a lot of meaning to my work.

On a personal note, my passion is travel. I’ve been to 47 countries and love hiking wherever I go. On my last two vacations, I walked across the entire country of Liechtenstein (only 10 miles/16 km) and hiked 70 miles in Hong Kong.

hiking in hong kong

How did you start this side hustle of urban hikes?

I left Google in 2012 as I was sick of commuting and working at such a large company. I had saved up enough money that I knew I could take a few months off. After a few months, though, I knew I needed to start figuring out a plan. I started looking at product marketing manager job openings at other tech companies, but at the time, my heart just wasn’t in it.

While I was taking time off, I finally got the chance to explore San Francisco. I got to see places I had been curious about for years like our mosaic stairways, Stern Grove, and Fort Funston. I don’t have a car, so I did a lot of this exploration on foot.

These explorations helped me fall in love with San Francisco again. I figured other people traveling to the city might want to explore the city on foot like I had. After doing research on tour businesses in the San Francisco area, I realized there were no hiking tour companies, so I decided to start my own!

At the same time as this was happening, I attended Chris Guillebeau’s World Domination Summit and read his book The $100 Startup, which says you don’t need a lot of money to start a business.

So with just a set of business cards and a website, Urban Hiker SF was born! We’ve now been around for around five years now. The whole thing has been a phenomenal learning experience.


How do you get your customers?

I got my first 200 customers through (think Groupon, but with an outdoors focus). After touring with customers, I would ask them to give my business a review on Reviews on Tripadvisor are a huge help for raising awareness and getting new customers.

Now, I get customers through a number of sources:

What are the costs involved in this hustle?

The wonderful thing about this hustle is that there are very few monetary costs involved. Each year, my fixed costs are a business license, business insurance, and a membership to our tourism bureau. Then I buy snacks for customers and pay guides. With my guides, I never have to pay them unless I’m already running a tour, so this means profitability is built into my business model.

How much money can someone make if they are starting out as a tour guide?

For now, our baseline rate is $50 for the first four hikers on the tour, and they get to keep all the tips they receive. They make more and more as we get more hikers. For example, I’m running a 40-person tour this week. I’ll run one group of 20, and the other guide will run the other group of 20. She’s earning $200 for this tour. With this model, when I make more money, so do my guides. When I succeed, they do too.

And when it comes to my business income, I earn between $2,000 and $8,000 per month, depending on the season.

Is this side hustle suitable for anyone or do you need any particular expertise?

Anyone can learn to be a tour guide and anyone can learn a tour route. However, not everyone is going to like being a guide. You have to be able to be outgoing and make small talk with people from all over the world, and not everyone likes that. Curiosity helps too as you have to be curious about history to want to learn more about the city.

What are your tips for beginners in this field?

If someone wants to get into the tour business, I suggest they do research on what’s already available in their city. I also suggest that they meet with other tour operators to get to know them. We’ve been able to create a whole community of tour operators in San Francisco, and we share information and best practices.

For starting up, I suggest practicing your tours a lot before you actually get out there. People can offer free or discounted tours to get practice in front of guests. Then gather as many reviews on Tripadvisor as possible to attract new customers.

I also suggest getting one’s logistical and financial ducks in a row. Make sure you’re set up legally in the city. Since you’ll be earning gross income, you’ll also be responsible for taking out your own taxes. I work with an accountant to figure out my estimated quarterly tax fees. Paying quarterly ensures that I won’t be slapped with a giant tax burden at the end of the year.

What are your future plans to grow this hustle?

My big project last year was to launch my guidebook Urban Trails San Francisco. My book features 50 hiking routes in and around San Francisco. It took a lot of effort, but I’m so proud to see it out in the world. You can buy it online as well as at many tourist-friendly locations like the bookstore at the Golden Gate Bridge and at Crissy Field’s Warming Hut.

urban trails san francisco

I’m going to continue to promote my book by doing some book talks and being featured on hiking and outdoors-related podcasts.

In general, the biggest way for us to do better as a tour company is to focus on corporate and private tours. I’m working with businesses and destination management companies—or DMCs (read more here)—to acquire more of these customers.

In terms of other plans, I just got a Merch by Amazon account, so I may create some merchandise. I may also create another book or eBook that I’ll publish on Amazon. What will I write about? I’m still figuring that out!

I thank Alexandra for giving a great insight into an awesome side hustle. If you are looking for a side income then why not show off your city and make money!!


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About Sireesha Narumanchi

Hi, I am Sireesha, and thank you for stopping by to get to know me. I am a work-at-home mom, a side hustler, and a firm believer in making "working from home" a success for everyone. I have worked in a remote job for over 11 years and tried many side gigs. I have been featured on many popular websites like Forbes, Business Insider, American Express, QuickBooks, The Muse, Moneyish, Virtual Vocations, Spark Hire, Bustle, Fairygodboss, Side Hustle School, Payoneer, Jobbatical, and Skillcrush.Read more...

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