8 min 56 sec

Retail Worker Cleans Up With Litter-Picking Business

Despite having little in the way of business skills, money, or education, this retail worker turns his father’s side hustle into a multiple six-figure business.
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What It's About

A litter removal business that cleans up in more than one way!

Business Model
Skills Required
Resourcefulness & Power of Observation
Profit Potential

Words of Wisdom

You would think that going from parking lot cleanup to snow removal or grass cutting is logical, but Brian discovered that it was a mistake. Focus on that core competency!

Fun Fact

Brian says people leave all kinds of weird and valuable stuff in parking lots. It’s not uncommon to come home with a handful of cash or a new phone!

Notes from Chris

Episode 870
The year was 1981, and Brian Winch was stuck in a dead-end job. He’d wake up, shower, and drag himself off for yet another shift at his local sporting goods store. Brian knew he didn’t want this to be his life forever, so he began looking for an escape route.

Back then, however, he had little in the way of money, education, or specialized skills. There was nothing that screamed “successful businessperson” on his resume. So, he narrowed his search down to opportunities where he could get his hands dirty and work up a sweat.

He would come home from work each day and brainstorm lots of different ideas, and eventually settled on one that was inspired by his late father.

Brian’s dad was one of America’s original side hustlers. A few days a week he could get up early before work and head out to sweep local parking lots. Occasionally Brian would tag along to help out, and remembered it being as easy as going for a brisk walk—so he figured he’d give it a try!

This started in the land before time, also known as before the internet. There was no way to Google “shopping malls near me” to find a list of potential clients. Instead, he did what everybody in the 1980s had to do to find local businesses ... he reached for the Yellow Pages.

He began by looking up Property Management companies to get a list of prospective clients. He did this in a way that didn’t involve pitching his services but rather focused on gathering information. He armed himself with a list of questions like:

● Do you manage commercial properties?

● Do you find it difficult to keep them clean?

● If so, would you like to learn how to have a cleaner parking lot for less money?

He repeated this process a number of times—and, within a couple of days, landed his first three contracts. Brian says it doesn’t hurt to have a little elevator pitch planned out if you want to try this yourself, but focusing on information and their needs is more important.

When Brian started his sweeping business he expected it to become a part-time, one-man-band, kind of side hustle. But it quickly took on a life of its own. Brian started to receive requests and client referrals for him to expand his business, until he had so much work he couldn’t handle it on his own, even after quitting his job.

Brian brought his brothers on board and gave the company an official name, Cleanlots. And, whenever the workload got too much, Brian would just hire another person. Sometimes it would be for just one parking lot a week, sometimes it would be a full weekend of sweeping. But this is how the business grew; one parking lot and one employee at a time.

Brian has been successfully running his business since 1981 and now earns a full-time income of over six figures a year, and his business has yearly contracts of around $650,000 a year. Many of the people who work for his company earn up to $4,000 a month for part-time work!

Recently, he’s been looking at ways to teach people how to start their own Cleanlots-style business and has even written a book on it. He wants to continue to pass on the model of what he calls America’s Simplest Business.

It’s also a business you can really clean up with!


  • Cleanlots: Learn more about how you can start a cleaning business yourself over on Brian's website!
  • WordPress: Brian used WordPress to set up his website for Cleanlots, and here you can learn how to install your own WordPress site in 5 minutes


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

Yours in the revolution,


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Quote of the Day
"It's better to be the best at something than trying to do something for everyone.​"
—Brian Winch #SideHustleSchool

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To infinity and beyond,

Chris Guillebeau