The Best Side Hustler I’ve Ever Known

5+ lessons I learned from a former coworker

If you Google, “Side Hustle”, you’ll get at least 111 million results (that’s six zeros). However, before “side hustle” was a trendy term, I had a coworker who I consider the “Side Hustle King.” I’ve worked with other people who had several side hustles, but no one has ever matched Jim.

Setting the Scene

I worked with Jim from 1990 to 2005. We worked together at two different office supply stores. Jim was about 25 years older than I was. He was a warehouseman like me. In fact, he is the one who trained me in order filling, shipping, receiving, and delivery route assignments.

But his true gift was making money whenever he needed it (and many times when he didn’t):

• Water heater suddenly broke — No problem. He would start selling BBQ tickets, and voila, the new water heater was paid for within two weeks.
• Car needed a new transmission — No problem. He’d hire two teens, lend them his lawnmowers, call a couple apartment complexes, and within a month, the transmission was paid for too.
• His son wanted a car — Jim wasn’t going to buy it for him. He would set his son up with a side hustle to pay for it himself.

Jim’s business savvy could have easily put him in the store’s management, but he didn’t want that. He wanted to clock in at 9am and leave at 5pm. Then he could have the freedom to side hustle whenever he wanted. Jim didn’t want a salary with “work as much as you need to get the job done.”

I learned many lessons about work, and especially about side hustles from Jim, and now, I will share some of them with you.

Jim’s Side Hustle Lessons

Lesson #1: Making Money is Not Hard; It Just Takes Work and a Simple Idea

None of his money-making ventures were what we would call “passive” income. They all took work and time. However, he wasn’t afraid of hard work. He had a list of ideas that he knew he could monetize and do so quickly.

Lesson #2: To Make Money, You Need to Have a Goal

Formally, we would call this a business plan. Jim never went to college, but through experience he had created about a dozen different business plans. Whenever he needed some extra money, he would pick the one he thought would be the most appropriate given certain factors:

How much money was needed

When the money would be needed

How much money needed to be put in up front

How much labor he had to play with (people, hours, etc.)

Once he knew the answers to these questions, he picked one of his side hustle plans and put it into action. It became like a “turnkey” operation each time.

Lesson #3: Never Stop Looking for New Opportunities

This was in the 1990s. We weren’t talking about “multiple income streams” and other jargony words like that.

However, conceptually, he practiced this all the time. If one side hustle became too competitive, he had two other new ones that he wanted to try.

He instinctively knew exactly how the supply and demand curve worked.

For example, one summer, there were tons of people selling BBQ plates as fundraisers. He told me, “Well, I can’t make money with so much competition. So, no plates this summer. I’ll shift to prepacked picnics.” (Same idea, but new packaging, and a new potential market.)

Lesson #4: Don’t Forget to Save For the Next Job

No matter what side hustle he worked on, he saved 10–15% of all the revenues. Jim put that money away in an account. That savings account became the money he could tap for raw materials for the next hustle. He didn’t have to dip into his family’s budget.

Without knowing, he was practicing a basic accounting concept called, “Business Entity.”

The side hustles were a “business” that he kept separate from his personal finances. They could help fund family needs, but the family didn’t fund the side hustles.

And the most important lesson:

Lesson #5: A Good Side Hustle Solves Someone’s Problem, Satisfies a Desire, or Creates a Desire

One time while we were working late unloading a large stock order, I asked Jim, “How do you come up with your business ideas?”

He said:

“I think of what can solve a minor problem someone has, what I can do to satisfy a ‘want’ people have, or I try to create something that they will want.”

Basically, he focused his side hustles on three categories: problem solving, desire fulfillment, and desire creation.

There were three additional important ideas he told me when we still worked together:

1. “My businesses never try to solve large, important problems. Those are too risky, and your potential customers start to debate whether they need your service or whether to hire a professional.”
2. “Lack of time is the problem most people have. I target things that people don’t have time to do.”
3. “Convenience will overcome price most of the time. I make my service so convenient people see the value in what I do.”

Final thoughts

Jim was a born businessperson. During the time we worked together, we saw three different management interns with Bachelor’s in Business, come and go. None of the three had the “nose for business” that Jim had.

I have not seen him for almost 7 years, ever since we both attended the funeral of another coworker. At that time, he had already “retired,” but even then, he told me he was running three side business:

• Buying, placing, and restocking gumball machines at local business (making about $800 a month in profit)
• Hiring out people to mow people’s lawns (making over $1,000 a month in profit)
• Being on retainer as a minor, fix-it “handyman” for an 8-apartment complex (a $1,500 a month fixed salary)

As a retiree, he was still actively earning $2,800 a month from his side hustles on top of his social security. He must be 75 years old by now, and probably not a handyman anymore. However, I am sure he’s still managing the other business and maybe even starting new ones.

If he had been 30 years younger, I’m sure not only would he have all the businesses I’ve already mentioned, but he would have an Etsy store, an Ebay flipping business, a Print-on-Demand Redbubble store, and then writing on Medium to give Tim Denning a run for his money.

Or, maybe he does and I just haven’t seen Jim’s stores and stories yet… 😄

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