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America's Simplest Side Hustle to Start

One question that I hear a lot is, "What is the simplest side hustle to start?" With so many ways to make money these days, it helps to narrow the list down to the most straightforward, most scalable, and most profitable options available.

Although 'simple' doesn't always equal 'better,' it has generally proven to be an effective strategy over the eons, especially for new entrepreneurs.

A "simple" side hustle is generally one that doesn't entail fancy equipment, government permits, or too much overhead.

Since 1981, Brian Winch of Calgary, Alberta, has earned a 6-figure income by cleaning up parking lots through his business CleanLots. He's even published a book detailing how he got started and hopes that others can use his knowledge to go into business for themselves.

We've invited him to share his secrets with the SideHustle.Tips community.

Here now, in his own words, is Brian Winch:

My Dad, the Original Side Hustler

Growing up, I never really knew the term 'side hustle,' but that definition perfectly fits my Dad. I grew up in a typical lower-middle-class family. My mom raised my brothers and me at home while my Dad worked two or three jobs to pay the bills. As a child, I never felt poor, but I knew that we needed to save where we could and couldn't afford to spend lavishly.

My Dad was employed as a school janitor, but he always worked in his spare time to make a little extra money. He would shovel snow in the winter, cut grass in the summer, and clean up litter outside a shopping plaza all year round.

When I didn't have school, my Dad would take me along with him. I always relished this father-son experience because I got a rare opportunity to hang out with my Dad, but I also found that I enjoyed the work. One of the jobs I particularly enjoyed was parking lot litter cleaning.

We would walk around the parking lot, sidewalks, and landscape outside a neighborhood shopping plaza and clean all the discarded trash. I liked being outside, getting a little bit of exercise, and I liked seeing the fruits of my labor. Seeing how easy it was to brighten up a neighborhood gave me a feeling of satisfaction and a sense of pride.

As someone from a lower-middle-class background, no one expected me to get a post-secondary education. Very few of my friends or classmates went on to university or college. After I graduated high school, I started to work at a sporting goods store, but I found my job unfulfilling. I also wanted to make good money, but I wasn't going to make it by working for someone else.

I started to look around for other opportunities and began looking for things I could do to make a little bit of extra money on the side. The trouble was I didn't have the skills or experience to do anything I considered "worthwhile." Most of my experience was working with my Dad, who unfortunately passed away in 1981.

My Dad was always a great source of inspiration, and I admired him. I took his passing hard. Although he didn't have a glamorous life, he had a strong work ethic and always spent as much time as possible with us, his family.

As I thought more about my Dad's life and what he accomplished, I wondered: why couldn't I do a parking lot litter cleaning business, just like he had done? It seemed easy enough, and it was more enjoyable than what I was doing, so I started it as a side hustle. Unfortunately, I didn't have my Dad's expertise to call on, but it seemed like an excellent opportunity to make some extra money.

Starting On My Own Business

I paid about $50 for some simple litter collection tools – nothing fancy, but enough t get the job done. From there, I was ready to start. All I needed were some clients. I began to call property management companies to see if there were interests in my services. This was back before the internet, and I found many of these companies by looking in the Yellow Pages telephone directory.

Every time I picked up the phone, I would make at least four or five calls, and for every one of those, I would have at least one request for more information or a request for a quote. I learned how to refine my elevator pitch to introduce myself quickly to my prospects. I learned how to explain who I was clearly, and the benefits of an on-foot litter cleaning service.

It didn't take me long to land my first client.

From there, I found more clients, and soon I was making more money with my side hustle than I was with my actual so-called real job! After only about two months, I quit my job and focused on my litter cleaning business full-time.

Growing My Business

Turning my side business into a full-time venture was a mental shift, but I was dedicated and determined to make it succeed.

As I contacted more and more businesses, the company grew steadily. I didn't mind doing cold calling as the property managers I talked to generally seemed interested in listening to what I had to say. Being a good salesperson is all about being polite, cheerful, good at communicating, and a good listener.

But being an introvert, selling didn't come naturally to me. I learned that it becomes much easier when you realize that you are simply sharing the benefits of your service with your prospect. People don't buy a service. They buy a solution to a problem they have. You are simply sharing with them how they can obtain a cleaner, litter-free property for less money while at the same time improving their image in the community.

I constantly hear people say to me that they can't sell or aren't good at it. But suppose you recall some of your past life experiences. In that case, you'll realize that you have had to "sell" yourself at different times in your life: making a case for a new toy, or a raise in allowance as a child, convincing someone to go on a date with you, or a job interview; these are just sales jobs in disguise. I found that you can sell almost anything, as long as you believe in what you're selling.

As technology became a critical part of everyone's life, I learned how to market myself through the internet. While I knew how to place an ad in the telephone directory or create a sales flyer, I had to learn how to set up social media pages, build a website, and attract customers through Google and LinkedIn. I learned terms such as SEO (search engine optimization) and landing pages, and even what a hashtag was!

The best source for new clients is your existing ones, so you need to provide exceptional customer service. Anyone can clean, but not everyone can or chooses to communicate with their customers. Our clients appreciate us acting as an "extra set of eyes" for them at their properties, making their jobs easier. When we are servicing our job sites and notice fresh graffiti, burned-out lights, property damage, or illegally dumped items on-site, we make notes and communicate any of such to our clients. Doing this also helps build trust and maintain relationships, leading to great customer reviews and referral business.

I was never scared of hard work and always willing to learn, so I soon found my business growing. Word of mouth spread, and I eventually had to recruit, train and manage others to keep up with the demand. With experience, I became even more profitable, and my small roster of clients grew into many. Today I manage an operation that services about 150 properties and generates nearly $650,000 a year in litter cleaning work.

Not bad for a $250 investment and a little passion, patience, and persistence.

Why Start A Litter Removal Business?

I'm the first to admit that starting a litter removal business isn't for everyone. If you care about fancy titles, you might want to consider getting into med school or getting an MBA. But the beauty of this business is in its simplicity. For starters, there is very little overhead. You'll need a phone, some litter collection tools, a vehicle, and that's it!

For many, starting a litter removal business as a side hustle makes the most sense. Since most litter removal occurs in the early mornings or late evenings, the operation fits nicely around a typical nine-to-five job. And if you want to transition out of that job and into litter collection full time, you can do so as you get more clients.

Time management is an essential factor for the business – as it is with any company. It is probably best to perform sales and marketing whenever you're able during the day and service your litter removal contracts after hours. As your business grows, there will be a tipping point where you are making enough with your litter removal contracts to begin to make sense for you to put all your attention toward your new business. You might want to manage your business and have others do the cleaning. The choice is yours to make.

It's a great business because it provides satisfaction that you're doing your part to reduce litter in your city. Every day, I'm thankful I'm not just some suit in an office going downtown to collect a paycheck. I get to make a difference, and that's the best feeling in the world! And it's a feeling you can have too!

The Simplicity of the Litter Collection Business

I coined this phrase over ten years ago, and it still holds today: it truly is America's simplest business. There's no need to share your profits with a third-party app, a marketplace, or a franchise ever again. You get to keep 100% of the profits.

Parking lot litter cleaning is done on foot using inexpensive hand tools. It's almost as easy as going out for a daily stroll – only you get paid to do it. You just walk the exterior of any commercial or industrial property, sweep up the litter, and toss it into a dumpster on site.

It's best to do it early in the morning before the businesses open when the parking lot is either empty or less busy. The fewer cars there are, the easier it is to spot the litter and clean it up!

You don't need to live in a big city, but you need a community of at least 30,000 to support your client's businesses.

How to Become a Parking Lot Litter Removal Contractor

Commercial real estate management companies are your best source of clients. Property owners contract them to manage their commercial properties. A management company typically has several properties in its portfolio.

While they are busy people, all you have to do to get started is google them. They usually list their phone numbers and email addresses on the company website, so all you need to do is contact them. Start developing an elevator pitch just like I did, and you'll start having success. Property managers won't mind spending a little money to make their lives easier and keep their tenants happy! Depending on the service, I would charge between $30 and $50 an hour, which was generally a lot less than what they were paying for a larger company to do the same service!

You're looking for small or medium-sized properties to handle, such as office buildings, shopping plazas, industrial parks – pretty much any commercial space that has a parking lot. You can cover these smaller properties by foot in only a matter of minutes.

Don't Do It Alone

The litter cleaning business has provided my family and me with a comfortable lifestyle. Now that I'm nearing retirement, I want to share my experience with you because I think that was what my Dad would have wanted. I believe he would have been proud of everything I have accomplished and no doubt a little surprised that I took his simple idea and turned it into a decent-sized business.

I'm only sorry that my Dad didn't get to see me and share in my success. He was never able to achieve his full potential, but he did manage to pass a lot of his knowledge to me, and now I want to do the same for you.

I'm not doing this to get rich, which is why I'm not franchising which would, frankly, make the most business sense for me, but I don't want to discourage people that were like me from trying out the business themselves.

I'm here to pass on my Dad's legacy in hopes that you'll break free of whatever shackles are holding you back from achieving the kind of success and lifestyle you want.

Everybody is a little different, and this business may not be for you, but if you're looking for something simple that you can do on the side and that you can grow, then I urge you to give it a shot.

In 2009, I wrote the first version of my instructional book on setting up and running your own litter cleaning business. I called it Cleanlots: America's Simplest Business. The book is more of an instructional manual, outlining my decades of experience and has everything you need to start your own business. Even if you don't want to create a litter collection business, it has a ton of helpful information you can use in whatever endeavor you decide to pursue.

I reveal all my tricks and secrets that have helped me grow my business to $650,000 in revenue a year; and because I know each person has their challenges that the book won't address, I provide my contact information for free support. The book has evolved over the years as technology changes and social media have become even more critical, but the fundamentals are all the same. I would urge you to pick up a copy at

So. What is the most simple side hustle? The answer to that question will be different for each person, given their life circumstances, skills, and likes and dislikes. For me, starting a litter cleaning business as a side hustle was the best choice I could have made.