What It's About
The tours are "free," but this creative Chicago guide still earns $2,500/month from them.
Words of Wisdom
Jeff has found his ‘free’ business model to be more beneficial than tours that charge per person. However, he stressed the need to maintain a five-star rating and grow his reviews. This is critical. Just like he was skeptical on his first walking tour, some people question his service’s legitimacy because it advertises as free. The rating assures guests that he’s a legit business.
There's a lot of interesting (albeit sordid) history in Chicago, and Jeff’s Free Chicago Walking Tours takes advantage of that with his Chicago Crime & Gangster Tour. On this tour, you'll learn how the Chicago mafia came to power as well as take you to some lesser known, infamous Chicago mob hangouts!
Notes from Chris
Episode 643Jeff Mikos has been the manager of a pet care business for a large grocery cooperative. He’s also dabbled in real estate, with two rental properties, including one he manages himself. A few years back, Jeff and his wife had an experience while traveling that ended up turning into an accidental side hustle. On an extended trip through South America, they stumbled upon a free city walking tour in Santiago, Chile. They were skeptical at first—how good could a free tour be?—but they decided to try it out. They ended up enjoying it so much that they sought the tours out in every city they visited. While on a tour in Quito, Ecuador, Jeff’s idea sprouted legs and took a walk of its own. He thought that implementing this model in his hometown of Chicago might have a walking chance. Jeff did some research and discovered this model had a low barrier to entry. “Who wouldn’t want a free walking tour?” Jeff got to work! He and his wife spent an entire weekend passing out brochures to every hotel and hostel in the area. Jeff racked up more steps than his pedometer knew what to do with but said it was hard to determine the ROI because there was no way to track it. (There weren’t any coupon codes or anything else that separated signups from one source versus any other.) Once his site was published, people began signing up. He remembers looking at his wife and thinking, “Huh, we’ve got guests!” Since its creation, Free Chicago Walking Tours went from nothing to a 5 star TripAdvisor tour company with hundreds of reviews. Jeff has maintained that five-star rating, earning a Certificate of Excellence from TripAdvisor. They walk a fine line! So far, they’ve led more than 15,000 guests on the tours, and it’s regularly bringing in more than $2,500/month in extra income. It’s not a ton of money, but at this point, the business is low-maintenance—not completely passive income, but close. He’d like to expand his operations to include additional cities in the midwest. He supplements his income with the private tours and hopes to be running even more tours next year.
MENTIONED IN THIS EPISODE:
- Free Chicago Walking Tours: Learn more about this soon-to-be Chicago institution over on Jeff's website!
- The Guardian | How to start a tour operator business: Interested in starting your own urban touring company? Get started, here
- Urban Hiker Climbs to Steep Success in San Francisco: A project manager turns a passion for the urban area of San Francisco into a substantial side income bringing in an additional $50,000 a year
- Policy Researcher Offers Private Tours of Nation’s Capital: A public policy researcher starts a Washington, DC tour guide business and overcomes the hurdle of competitive TripAdvisor reviews
- Florida Man Leads Scooter Tours After Watching Macklemore Video: Had a broken keyboard, bought a broken keyboard: this corporate refugee relocates to Florida and kicks off a new hustle leading adult scooter tours
Download 2020 episodes: JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP Download 2019 episodes: JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC Download 2018 episodes: JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC Download 2017 episodes: JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC
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! ✈️
Want to build any kind of website for your hustle? If so, you'll need somewhere to host it! This is the reliable company I've used for my past 5 websites. It's cheap, flexible, and you can get support 24 hours a day.
Get your own hosting plan for just $5 a month!
Quote of the Day
Sponsors & Gratitude
This week, Side Hustle School is brought to you by Crazy Enough to Work, a popular podcast and film series. 📈
When the rest of the world is still zigging, some companies know when it’s time to zag. Elizabeth Banks has teamed up with State Street Global Advisors to make a series of podcasts and films that uncover the bold moves mid-cap companies make to thrive and survive.
Side Hustle School is for you! If you’re enjoying it, please take a quick moment to leave a rating or write a quick review. It's really easy and it makes a difference! ✅
It also makes a huge difference when you tell your friends about the show. Remember, it's 100% free and listener-supported.
Keep in Touch
There’s a new story every single day on Side Hustle School. Episodes are produced to be short and to the point—I know you’re busy. Be sure you subscribe to get instant notification of the day’s broadcast!
To infinity and beyond,