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How a Side Hustle Taking People on 'Urban Hikes' Became a Lucrative Business Kansas City native Lisa Peña shows tourists and locals parts of the city they'd never see by car.

By Jonathan Small

Key Takeaways

  • Lisa Peña took her passion for hiking into the streets of KC, starting a tour side hustle
  • The business took off during the pandemic when people were social distancing outside
  • Urban Hikes KC is now a thriving full-time business

Back in 2018, Lisa Peña heard a podcast about an entrepreneur in San Francisco who ran a business leading hikes across San Francisco. The concept was simple: Instead of taking hikes along nature trails, urban explorers were trekking through alleyways and winding city streets.

"I got that excited feeling that I've only had a couple of other times in my life, and I knew that I had to bring urban hiking to Kansas City," Peña told In Kansas City.

The Kansas City native launched Urban Hikes KC the following year as a side hustle, charging customers $28 to take guided tours with her on foot around the city she loved. Today, that business is a profitable, full-time endeavor that offers ten different hiking routes with a staff of 6 guides. Here's how she put Urban Hikes KC on the map.

A passion for travel

Like many successful entrepreneurs, Peña took an activity she had a passion for and figured out a way to monetize it. A former Peace Corps volunteer and backpacker, she loved to explore internationally and locally. Peña applied that same curiosity to her hiking business, taking tourists and locals to sights off the beaten trail.

After hearing the podcast interview about UrbanHikerSF, she contacted the company's founder, Alexandra Kenin, and asked her questions. Peña spent the next year researching routes, establishing a social presence, getting insurance, building a website, and figuring out a payment system.

Starting off as a side hustle

Peña launched her business in 2019 while working for Girl Scouts of NE Kansas & NW Missouri. Her first hike was the Crossroads Westside Urban Hike, which weaves in and out of alleyways in the city's Arts District.

Photo by Urban Hikes KC

"I started it out as a side hustle," she told Marketplace. "I didn't know how much money I was going to earn. I literally was starting from scratch. There was no other urban hiking sector in Kansas City."

Interest was so great that she added another tour to her business and then another. Soon, she realized she'd have to quit her full-time job if she wanted to scale."That was a scary leap," she says.

One of her first moves was upping her price from $28 a head to $38.

Slow burn

Peña concedes that she made no money in the business the first few years. Her expenses included insurance, her guides, and other bills associated with the business and life.

But in the summer of 2020, she started getting more guides and routes, and the business began to boom. "It was a great thing to do during the pandemic since we are mostly outside and can be socially distanced," Peña told In Kansas City.

By 2021, over one thousand customers took hikes with her company. By 2022, she had so much business she had to hire additional guides and add more routes.

As for profits, she's doing just fine now. "Finally I am making an income that is a sustaining income," she said on Marketplace.

What guests can expect

Peña says urban hikers can expect to see a side of Kansas City they've never seen, "even in neighborhoods they think they know. We learn about the history and stories of people who made a difference in Kansas City, and see different types of outdoor art, including murals, walk-up hidden stairsteps, bridges, alleyways, and parks."

Jonathan Small

Entrepreneur Staff

Founder, Write About Now Media

Jonathan Small is an award-winning author, journalist, producer, and podcast host. For 25 years, he has worked as a sought-after storyteller for top media companies such as The New York Times, Hearst, Entrepreneur, and Condé Nast. He has held executive roles at Glamour, Fitness, and Entrepreneur and regularly contributes to The New York Times, TV Guide, Cosmo, Details, Maxim, and Good Housekeeping. He is the former “Jake” advice columnist for Glamour magazine and the “Guy Guru” at Cosmo.

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