10 min 51 sec

Urban Hiker Climbs to Steep Success in San Francisco

A project manager turns a passion for her city into a substantial side income of $50,000 a year.
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What It's About

An urban hiking tour company with low startup costs.

Business Model
Skills Required
Research & Resourcefulness
Profit Potential

Words of Wisdom

The best part about this side hustle model is that pretty much anyone can start something similar. Research tourism in your area, and ask yourself if there is enough tourism in your town to start a tour. If there is, what kind of tour do you want to run? Are there already competitors in your area?

If it's something that you think is feasible to do, plan out a couple tours and test them out with people you know!

Fun Fact

Most of the challenges Alexandra has had to face are related to her having to cancel tours due to rainy weather. Normally, this only happens a few times a year, but last winter the San Francisco area experienced the wettest winter ever recorded since they started tracking rainfall in 1895! That definitely slowed things down for Urban Hiker San Francisco before it picked up again this spring.

Notes from Chris

Episode 158

San Francisco-based Alexandra Kenin has a flexible job as a project manager and editor for a fully-remote company. It’s a dream job in the sense that she’s able to set her own schedule and go back and forth from focusing on those job responsibilities to building something for herself.

The company is in the tech industry, but Alexandra’s side hustle is completely different: it’s all about getting outdoors and showing city-dwellers and tourists a lesser-visited side of SF—the part of the city that includes scenic hills and hiking trails.

Depending on the season, Urban Hiker San Francisco: makes between $2,500 and $8000 per month, peaking in July. Overall, gross income is about $50,000 per year. Corporate groups are the biggest source of income. She typically earns $1000+ for each 2-3 hour event. Alexandra now has 4-5 contractors working for her, depending on the season.

More than 3,000 people have hiked with Alexandra and her guides, including a lot of foreign visitors. Sometimes it’s their very first day in the United States, so she loves being able to show off her city and provide a good introduction to the USA.



Inspiration is good; inspiration combined with action is better. Now get back to work!

Yours in the revolution,




Earn 50,000 travel rewards points (enough for 2 round-trip plane tickets or $625 in travel credit). You'll also earn 2x points on all travel and dining spend, with zero foreign transaction fees.

I use this card every day all over the world! ✈️

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Quote of the Day
"Anyone who lives in a city could create a tour business, and it costs virtually nothing to start! All I spend on each hiking tour is my time, and it’s almost all pure profit."
—Alexandra Klein #SideHustleSchool

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To infinity and beyond,

Chris Guillebeau