Leaving Google And Starting A Hiking Tour Business

Published: January 30th, 2019
Alexandra Kenin
Founder, Urban Hiker SF
Urban Hiker SF
from San Francisco, California, USA
started October 2012
market size
avg revenue (monthly)
starting costs
gross margin
time to build
270 days
growth channels
Word of mouth
business model
best tools
Twitter, Instagram, Canva
time investment
Side project
pros & cons
40 Pros & Cons
18 Tips
Discover what tools Alexandra recommends to grow your business!
Discover what books Alexandra recommends to grow your business!
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Hello! Who are you and what business did you start?

Hi all! My name is Alexandra Kenin and I run a tour business called Urban Hiker San Francisco, or Urban Hiker SF.

We run urban hiking tours that explore the stairways, hills, and hiking trails of San Francisco. Our standard 5-mile / 3-hour tours are offered on a weekly schedule, but we also offer private and corporate tours on our clients’ schedules. This video offers a short visual explanation of what we do.

For our standard tours, our customers are often visitors to San Francisco looking to see a new side of the city. Our corporate clients are often local companies who want to do fun activities with team members that get them out of the office for a day.

I make between $40,000-$45,000 every year on this project and up to $8000 a month in summer months at the peak of the tourist season. Winter is a slower tourist season for San Francisco and also our rainy season, which means I earn less monthly revenue during these months. For us, the biggest money maker is corporate tours. With corporate tours, we can make $1,000 or more in just a few hours.

Since the business launched in 2012, we have hiked with around 5,000 people from 30+ countries. At first, I did most of the tours myself. I now rely on between 5-7 guides to run the tours for me. I occasionally do tours myself but have been outsourcing to guides more and more. Our most popular tour day is Saturday, and since I just started a family, I haven’t found myself wanting to work weekends.

A corporate group enjoying an Urban Hiker SF tour

In addition to running tours, I am also aiming to become the go-to expert for hiking around San Francisco. I have written a book, Urban Trails San Francisco, which features 50 routes in an around the city.

I’ve sold over 8,000 copies since the book came out in November 2016. While working on the book has been fun, and I’m working on a second book, Urban Trails East Bay (Berkeley, Oakland, and other cities east of San Francisco), this is more of a branding play than a money maker. I’ve only made $5,000 total for the book for the countless hours I spent on it.

Urban Trails San Francisco

What's your backstory and how did you come up with the idea?

Before starting Urban Hiker SF, I worked as a marketing manager at Google from 2007 to 2012. By the end of my time there, I was very burned out on big company politics—and mainly on commuting (up to three hours a day), so I knew I needed to leave. I had saved a bunch of money and knew I had enough funds to take some time off.

After I quit, I took some time off to explore San Francisco. By that time, I had lived in the city for 4.5 years, but I didn’t know it that well as I spent most days at Google headquarters in Mountain View. With my time off, I explored our city’s mosaic stairways, our beautiful beaches, our “wave organ”—all the places I had wanted to visit, but never had the time to.

Take actionable steps toward your goals every day and you’ll make progress. Also, once you get started, you’ll meet people along your way to help you. You won’t necessarily find those people if you’re only doing research and not actually launching.

As I explored the city more, I realized that other people might also want to see the things I was seeing on my explorations. Thus was born the idea for Urban Hiker SF. I had no background or expertise in tourism—just a lot of interest and motivation.

I had read the book The $100 Startup by Chris Guillebeau, which taught me that I didn’t need to spend a lot of money to start a business. So I spent $100 to reserve a domain name and host a website on Wix.

I chatted with a few local tour operators to make some connections and get some initial advice. Then I sought out my first customers!

My first hikers came from three sources:

  1. My dad’s wife’s friends wanted to do a hike with their monthly hiking group
  2. At the time, Airbnb was running small local experiences (much smaller than their current Experiences program) and I reached out to them to see if they would be interested in my running a hike for their local Airbnb guests. They said yes!
  3. I ran a small coupon promotion with the now-defunct Zozi, a Groupon-style company specifically focused on outdoor activities.

After running hikes for all of these groups, people began to write TripAdvisor reviews, and that helped more people find me. I also focused on getting new customers through a few new channels:

  1. Partnerships: I worked with travel marketplaces like Viator and wedding registries like Zola to sell my tours).
  2. DMCs: Destination Management Consultants (DMCs) organize large corporate events with hundreds to thousands of people. They book hotels, restaurants, and activities. I reached out to local DMCs to present them with my Urban Hiker SF offering.
  3. Networking: I asked friends still in the corporate world if their companies needed team building activities.
  4. PR: I joined San Francisco Travel, our visitor's bureau, and they refer me out to traveling journalists who write up my tours. These journalists’ blog posts and articles attract new guests.

In 2013, I realized I could not survive on Urban Hiker SF income alone. I decided to pick up another more stable job while I built Urban Hiker SF. Since 2013, I have been working at Wordsmithie, an agency that does writing and design projects for tech companies. My boss was a former Googler, and that helped me get the job. To this day, I work 20 hours a week for Wordsmithie and spend the rest of my work week on Urban Hiker SF.


Take us through the process of designing, prototyping, and manufacturing your first product.

To appear like I was a more established business, I wanted to launch my tour business with three tours, but I knew I had to start with one—and I wanted that tour to be perfect.

First I needed to settle on a distance. I figured 5 miles could work as many people could hike that distance. I also wanted the tour to be 2.5-3 hours so that people could fit a hike in between meals and so they wouldn’t be too tired afterward.

I try to start my day by writing down three things I want to accomplish for my business. These can be small things like making sure to email a potential client, updating something on my website, or writing a part of my new book.

Twin Peaks is a scenic overlook in San Francisco and a major tourist area, so I knew I wanted the hike to go there. And I figured the Castro neighborhood (SF’s gay neighborhood and an appealing tourist attraction) would be a central place to start the hike. Then I decided to find the most interesting way to get from the Castro to Twin Peaks and back.

I found two other panoramic hilltops, a eucalyptus forest, and a bunch of stairways to make the hike interesting. I beta tested my initial route with friends and family and got feedback. One person suggested I should do the tour in the reverse order (clockwise vs. counterclockwise) and that was a great suggestion.

I then added 10 history stops along the tour so that people could learn while they were hiking. After all of this work, I had to memorize the route and the history. None of this cost any money, but it did take a bunch of my time—about a month in all.

I then repeated the process to create two other tours. I identified good, central start points, a few “anchor points” (key scenic points along the way), and history notes, and was able to launch three tours.

In terms of regulation, I spoke with a lawyer to see if I should do a sole proprietorship or LLC and I decided to go with a sole proprietorship and get insurance to cover potential legal issues. I officially registered my business with the city of San Francisco and bought tour insurance.

Describe the process of launching the business.

I launched my business website, www.urbanhikersf.com, on the Wix platform with a site I created myself. I bought the domain name from Google and let Wix handle the hosting. I also signed up for a service called Xola. Xola is a back-end booking system that powers “Book Now” button on my site. It also lets me process credit card payments and displays a tour calendar on my site. I still use this service to this day.

I spent about $100 on the initial web setup. Xola charges me about 3.5% of every booking, but they only charge me when I make money, so that’s nice! Registering the business with the city of San Francisco cost about $90 and insurance cost about $700. I self-funded all of these charges.

I got my first set of customers from the Zozi deal mentioned above. I had about 200 people buy the coupon and about 100 people actually come for a hike. I asked these people to write TripAdvisor reviews and since then, I have had a steady flow of customers.

Today, people find me through Google Search and TripAdvisor, and I’ve also joined up with marketplaces like Airbnb and Viator to sell my tours.

For lessons learned, I felt like this was an “if you build it, they will come” situation. As soon as I put myself out there, I started getting clients.

Since launch, what has worked to attract and retain customers?

For getting clients, as mentioned above, my main customer acquisition channels are my own website and partner sites like TripAdvisor and Viator.

To attract customers to my website, I do a regular Search Engine Optimization (SEO) audit using free resources like this Google SEO Guide and Wix SEO Guide. A few example SEO exercises I do are:

  1. Use the Google Search Console to understand my search performance and see if Google encountered are any errors crawling my site.
  2. Make sure that my page titles will display properly in search and that my meta descriptions make for good search result snippets.
  3. Use Google Analytics to see which keywords drew people to my site and try to place those keywords on my site (when natural, not forced).

I’m still far from an expert, so I may use an SEO expert in the future to further optimize my site.

Additionally, I regularly ask customers for TripAdvisor review, so I can continue to rank highly on that site.

Another big revenue channel (also mentioned above) for me is Destination Management Companies. These DMCs may only have one client for me a month, but I can earn $1,000 or more in a few hours each time I work with them.

For bigger groups like those that come from DMCs, I team up with a partner company Tam Hiking Tours. Together, Debra, Tam Hiking Tours’ founder, and I can handle groups of 40+ people. We add up all the profits and split them. We come to each other with requests for big groups—we’ve found it’s a great way to share business and still do well financially.

A few times a year, I do dating hikes with Match.com. On these hikes, 10-20 people show up and go on a hike and group date. That’s been fun and adds to my quarterly revenue.

For PR, I found the most effective way to get press was through San Francisco’s visitors bureau, San Francisco Travel. I pay $350 for an annual membership with them and they occasionally send journalists my way. When I take a journalist on a tour for free or for a discounted media rate, they often write about my business on their blog or in a magazine or newspaper article.

I do social media just to have a presence—it doesn’t often result in tours. I think I’ve booked 1-2 tours ever from social media. Still, I maintain profiles on Facebook, Twitter, and Instagram.

In terms of email, I send out a quarterly newsletter to my hikers. I have about 1,500 people on my email list. I don’t have many repeat customers since people are often out-of-town guests and don’t live in San Francisco. Still, these folks can always refer me to their friends or colleagues who are visiting San Francisco. I can also refer them to other non-location-specific items I sell like t-shirts. My book, Urban Trails San Francisco, can be a popular gift, so I use the newsletter to promote the book, and people buy the book and give it to friends.

How are you doing today and what does the future look like?

Given that I have another job that takes up 20 hours of my time and I’m in the thick of working on my second book, I’m pleasantly surprised that my business keeps earning money—even when I don’t spend that much time on it. I have engineered my business in such a way that most of the time I only spend money when I earn money, so it’s designed to be profitable. I only pay guides when I have hiking clients, for example.

Take actionable steps toward your goals every day and you’ll make progress. Also, once you get started, you’ll meet people along your way to help you. You won’t necessarily find those people if you’re only doing research and not actually launching.

I had a baby in July 2018 and stopped guiding most of my hikes myself in May 2018. This has been good for me (more personal time) and also good for my guides (more opportunities to earn money).

Profits were flat between 2017-2018, but I’m looking forward to a productive 2019. As I will not be having a baby during this year’s busy summer season :), I’m very hopeful for a good year.

For more 2019 projects, Tam Hiking Tours (mentioned above) and I are partnering with Tideline water taxis to offer hiking and boating tours on a regular schedule. We hope this will add a source of additional monthly revenue for us.

And in 2020, my second book Urban Trails East Bay will come out. The book is due in March 2019, and I’m excited to wrap up this project with my publisher.

Eventually, I may want to expand to other cities, like Los Angeles, but that seems like a lot of management, so I’m holding off on this for now. That said, if anyone reading this lives in LA and would like to be our LA city manager, I’m open to chatting!


Through starting the business, have you learned anything particularly helpful or advantageous?

One helpful thing I’ve learned through running my business is that just a few of my customers lead to most of my revenue.

When I work with corporate clients or DMCs (see notes on DMCs above), most of the time, they’re bringing me 10-20 hikers at a time (and sometimes 40!). This means I’m earning at least $500 at a time for each hiking outing—and often $1,000 to $2,000. On hiking outings with small groups, my per-hike earnings can be as low as $200. This tells me I have a true opportunity to grow my business by focusing in on corporate clients and DMCs.

A challenge I’ve faced is in training and retaining guides. It often takes one month to train a guide—to teach them the route and history for our hikes. My guides are often working for me as a side job, so they might leave us when they get a full-time job, they graduate from grad school, etc. I need to be able to streamline the training process so that I can get guides ready and on board earlier. That way, when guides inevitably leave, I won’t feel like I’m a month away from having new staff.

In terms of helpful skills, I try to start my day by writing down three things I want to accomplish for my business. These can be small things like making sure to email a potential client, updating something on my website, or writing a part of my new book. My general thought is that if you don’t write it down, you might forget it. Plus, I love writing things down because it feels so good to cross something off a to-do off a list!

What platform/tools do you use for your business?

Here is a list of tools I use to keep Urban Hiker SF up and running:

  • For my website, I use Wix. It’s a drag and drop design system and requires no coding experience.
  • For my domain name, I use Google Domains. It’s cheap and easy!
  • For my back-end booking service, I use Xola. This includes accepting credit card payments from customers, assigning guides to tours, managing my tour calendar, etc. I have met Xola’s team and they’re nice and very responsive.
  • I use Xero as my tax software. The $30/month I spend is worth it when I need to generate tax forms at the end of the year.
  • I use Track 1099 to pay contractors. I like doing everything on the books as I’m scared of authority figures like the IRS. ;)
  • I use Google Docs to create training materials and to share them with guides. Google Docs makes everything easy to edit and share.
  • I use Google Sheets to keep track of Urban Hiker SF’s monthly bookings and revenue. I’m totally Googlified, so this is just part of my whole system.
  • I use Square to do one-off invoices with clients. This helps when I can’t run a custom transaction through Xola.

What have been the most influential books, podcasts, or other resources?

Chris Guillebeau’s The $100 Startup was very influential in starting my business. It helped me realize that I didn’t have to spend a lot of money to test and launch something. I also loved his book The Art of Non-Conformity, which is about living an unconventional life in a traditional world.

Another favorite is Tim Ferris’s the 4-Hour Workweek. In short, the book wants you to work smarter and not harder, and I’m definitely in favor of that. I’m still working too much for my own liking though.

Today I listen to the Side Hustle School and Side Hustle Nation podcasts. These are interesting to me as my business is still a side hustle category as it’s only part of my income.

Advice for other entrepreneurs who want to get started or are just starting out?

I know many others have said this before me, but my advice to budding entrepreneurs would be to just get started. Before you start your business, you may think that you want to already have everything figured out before you launch, but you don’t need to do this—it’s impossible anyway.

Take actionable steps toward your goals every day and you’ll make progress. Also, once you get started, you’ll meet people along your way to help you. You won’t necessarily find those people if you’re only doing research and not actually launching.

Another thing that helped me was knowing that I didn’t need to spend a lot of money to test my idea. That lowered my stress level and allowed me to try out my business without a lot of negative financial consequences.

A third piece of advice would be to tell people not to go it alone. I run my business as a sole proprietor, but I have a community of people around me to help me. That includes my boyfriend and a network of other San Francisco tour company owners that I can ask for advice.

Are you looking to hire for certain positions right now?

I am always looking to hire more talented guides to lead our tours. No previous guiding experience is necessary, but a great outgoing personality is a huge bonus.

If anyone is interested in running a branch of Urban Hiker in Los Angeles, I’d also be interested to talk to potential city market managers who could run the LA business. I’m not sure I’m opening Urban Hiker LA, but I’m open to it!

Where can we go to learn more?

Want to start a tour company? Learn more ➜