The List of Side Hustles I Have Had Over The Past 20 Years

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I’ve been an entrepreneur for most of my life. I have successfully built traditional businesses, but as I looked back over my entrepreneurial journey, I realized that I had an affinity towards side hustles.

Today, I am a big proponent of the side hustle as it is a great way to grow a business with far less risk than going all in with a new business venture (of which a high percentage fail). Imagine the feeling of having your financial needs met through a day job, and then using your side hustle money to get ahead, save, and plan to live a great life in your retirement years. If I had to do it all over again, that is what I would do, so my hope is to inspire others to take that path. And keep in mind, your side hustle doesn’t have to be forever. Many people make the transition from side hustler to fully self employed, and they do so with a much more solid backing using the side hustle as a starting point.

Below, I have documented my side hustles over the years.

 My Side Hustles as a Kid
Someone posted a few months ago in the question in the FinCon Slack channel asking “what your first side hustle?” Mine was selling greeting cards door to door at about 10 years old. I recall having an allowance and being encouraged to save for things I wanted and this was a way to maximize my savings. From there, I progressed to making candles and selling them (long before the MLM candle companies existed). As I got older, I took on the traditional teenage side hustles of delivering newspapers and shoveling snow (I haven’t always lived in a desert) 🙂

My Side Hustles As an Adult
So I also have a confession; I have ADD. And I am not just saying I have shiny object syndrome, I mean I have been diagnosed and strongly advised to be medicated in the past for the disorder. I never wanted to take medication, as I did not want to limit the creativity that often comes with the disorder. Nonetheless, I have had many side gigs over the past few decades, and I am sure some were in part to wanting to satisfy my curiosity of trying something new. That being said, here is my list of side hustles that I have made money from.

  • Auto Technician – Prior to my career in real estate (which was before my career in digital marketing), I was an ASE Certified Master Technician for many years. It’s a known fact that many technicians “do side work.” As I recall, it was a great side income and I even worked at several shops that allowed me to use the shop to do side work on my off hours.
  • Buying & Selling Cars – So another side gig that many auto technicians get into is buying cars that need work and fixing them and then selling them. In the state of Maryland where I did this, there was a limit to the number of cars you could sell in s year without having a dealers license, but I did this with colleagues, so we could do 6 cars per year in each of our names without a need for a license. The best deal I recall was buying a Honda Prelude from a customer who didn’t want to fix it. I offered him $200 and he took the offer. I put a fair amount of work into the car, and sold it at a nice profit (over $1,000 profit to my recollection.) At one point, my colleagues referred to me at the $200 car guy because I acquired at least 3 vehicles for $200 and sold them all at a profit. In one case, I never even picked the vehicle up. I found a buyer who paid for $500 and went and picked it up from the address of the original seller.
  • Rideshare (Lyft / Uber) Driver – I am seeing a car theme here and that was not intentional. As rideshare driving became more popular, I decided to give it a shot. I was running a traditional business and I heard that people were making good money doing this. I saw some amazing offers of guaranteed hourly rates of $25-$40 per hour, and I bit. I started with Lyft and if I had not, I may not have stuck with it. Lyft was offering those guarantees for drivers who were willing to work the late night / early morning shift (10pm to 3am) and if I did that on Friday and Saturday nights, I was bringing in about $300 per weekend… That’s a mortgage payment!
  • Timeshare Sales Rep – Don’t laugh at me or judge me. I actually own a timeshare and at one point in my conversation with one of the reps, I asked him what it took to sell timeshares. He told me all I needed was a real estate license, and that I could do it on the weekends since that is when they see most of the people. What he didn’t tell me was that it required you to be pushy and sell an overpriced product that people would ultimately hate you for. If you haven’t figured it out, I don’t recommend this as a side hustle. Ironically, I now help people get out of timeshares.
  • Blogger – I’ve been blogging since roughly 2006. I have had various levels of success as a blogger including selling one of my blogs and having a decent side income through my blog, mostly fueled by affiliate sales. Please know that it takes a lot of work to grow a blog to the point where it is profitable.
  • Casino Dealer – Ok, so I was not a real dealer in a casino. Lord knows I could not survive in that much cigarette smoke. I did however find a side gig years ago with a company that does casino parties. I was actually looking for poker tournaments to play in locally and I ended up becoming a casino party dealer. I would deal mostly blackjack, but I also dealt a little poker and even craps which is a super high energy game. They were great people to work with (and I am still friends with the owners today) and there were lots of weekend events, as well as many over the holidays that included nice tips. There were also opportunities to make money by setting up and / or running an event for additional pay. I did this at least once for a small event and it included loading and driving the truck, setting up the event, taking it down, reloading the truck and taking the truck back to the office. If I recall correctly, I made about $200 in one evening, which was pretty sweet. Best of all, the checks were prepared in advance so at the end of the (typically 3 hour) shift, you would get a check and were free to go home.
  • Affiliate Marketer – I LOVE affiliate marketing. When I started my online endeavors back in 1999, I started as an affiliate marketer. At the time I had no idea what affiliate marketing was. I was told that if I shared a link with a unique code it would be linked to me and I would get paid for it. I eventually had a thought that I could build a website and add the links throughout the site, so I taught myself HTML (this was before WordPress and blogging software was around) and built a website. Since no one was coming to my site, I eventually learned SEO (search engine optimization) and started to get people to not only visit my site, but click on that link and spend money.Today, I incorporate affiliate marketing in as many business endeavors as I can and I love getting those emails telling me I just made some money.
  • Catering – I had a friend who was talking about how much money he made part time as a caterer and I asked him if his company was hiring. As it turns out, they would get people on their call list and then when they had events, they would reach out to the list until the event was filled. If you did a great job, you were moved to the top of the list. All you need is a tux, which you can pick up at a consignment store (as I did) or Goodwill. Catering gigs usually have opportunities for food servers, bartenders, or kitchen help. Kitchen help is a decent gig if you are good in the kitchen and you won’t even have to dress up. 🙂
  • Independent Sales – I am one of those rare people who actually likes to sell. If you are good at sales, all you need is a good product. As an independent sales rep I have sold everything from discount cards for gas stations to home improvements.
  • Network Marketing – Have we all “tried” networking marketing at some time or another? I am actually one of those people who believes that network marketing is an amazing way to earn a living because of the low cost of entry and the usually amazing training. Where people fall short is “selling” something they don’t really believe in, something that doesn’t have real value, or something that is overpriced. I learned a lot on my journey and if I had to start all over again, I would not hesitate to build a business using a network marketing company. Although I am not actively building a network marketing business, I still earn residual income from work I did over a decade ago.
  • Freelancer – If you’ve got skills, being a freelancer is a solid way to make money as a side gig. I have done lots of freelance SEO since learning the art back in 1999. In fact, this was a side gig that grew into a full-fledged company that I eventually sold to my partners (and is still in business today!)
  • Domainer – I kind of fell into domaining because of my work in digital marketing. I had kind of an addiction in buying domain names, and around 2010 (as the mortgage business started to tank) I started to sell those domains before the market went away completely. I eventually learned the right types of domains to acquire, learned how to acquire them for a few bucks, and started to get 3 and 4 figure offers for my domains. In my experience, domaining is good side money, but it’s not consistent because you can’t control the buying cycles.
  • Affiliate Manager – Being an affiliate manager is a great gig for someone who is experienced in affiliate marketing and enjoys team building. I have been an independent affiliate manager and also built and managed affiliate programs as a part of my corporate roles. As an affiliate manager, your role is to recruit and train affiliate marketers to promote the products and services of the company you are representing. You can be paid with a base salary plus a percentage of sales, or simply as a percentage of sales. It’s a grind because statistically most affiliates don’t produce sales.
  • Field Inspector. Real estate and insurance companies often hire field inspectors to review properties or verify work that was completed. It’s a pretty simple job, mostly requiring a camera and the ability to fill our simple reports. When I was working in the mortgage business, I somehow ended up learning about this business. I still recall my best day, where I did 10 new property inspections before I got to my office. These were basic inspections that paid $20 each, which means I earned $200 before I even got to my office.
  • Instructor. When I had my first job in online marketing, I recall having lots of free time and I was looking for something else to do to grow as a professional. I was passionate about the web and was always helping people figure stuff out, so I set out on a journey to teach. Ultimately, I was hired by a school called The CompuClub where to teach and I taught a variety of courses including the History of the Internet and Basic HTML. Who knew it would set the stage for me to be a speaker and trainer.
  • Paid Speaker. If you enjoy speaking in front of crowds or teaching workshops or seminars, being a paid speaker could be a good side hustle for you. Most speakers start out speaking for free, and eventually grow into becoming a paid speaker. My journey was no different. I started out by letting people know that I was available to speak and took many unpaid speaking gigs. One day I decided to ask for money to speak. The event coordinator said she did not have a budget to pay me. This was an industry association having a monthly meeting, so I asked her if they attendees were paying to attend. She confirmed they were, so I then asked if she thought they would each pay an additional $10 to learn how to grow their businesses. She agreed that it made sense, and I don’t recall if she raised the fee or not for the attendees, but she clearly saw the value in what I was bringing and agreed to pay me.
  • Travel Agent. When I was in my 20’s I had the opportunity to travel all over the world by leading teams of teens on overseas mission trips. I developed a passion for travel and learned that a real estate colleague for mine owned a travel agency. I asked him what was involved in selling travel and he basically said, “a business card.”
  • Waiter. In one sense being a waiter is a part time job, but in another sense, it has many similarities to a side hustle and here is why. When I was waiting tables, I saw the entrepreneurial angle and that was the fact that when I showed up, I was given a certain number of tables to use to make money. My goals were to build rapport, make offers, sell food, earn big tips, and turn over tables. Some people may not know this, but in many restaurants servers develop regulars who ask for them, and often tip quite well. I could also pick up shifts pretty much when I wanted, and I learned the best times to do so. If I needed to pay a bill, I could show up and make some extra money. On a good Friday or Saturday shift, I could make $150 (cash) and if I worked a double shift, it was easily $200 if not $300. Truth be told, I really grew to enjoy the restaurant business, and had even thought about owning a restaurant, until I learned how many of them fail.

I know that sounds like a lot of side hustles. I guess that kind of gives some insight into my age (I am not in my 20’s anymore) 🙂 But the reality is I have been side hustling all of my life, no matter what I did for work full time whether working for myself or someone else and I still do it to this day.

I’d love to hear about your side hustles, so feel free to share in the comments section below and tell everyone what you are doing.

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Inspiring readers to earn, grow, and save money, retire early and never stop side hustling!