Vend, Write, Trade: A Side Hustle Story

Before I ever started a side hustle, I was like most people. I worked for someone else and collected a paycheck. Until things took a turn…

Photo by Skitterphoto from Pexels

I walked out of his office and left the building. It was over, well, almost. I stuck around for ten weeks to transition someone else into my role. It was a painful ten weeks, but I did it to keep the family together. At least, that’s what I kept telling myself.

I had wanted to run my own business for years. The arrangement I left seemed like a perfect fit. But it didn’t work out…

I was a college dropout military veteran whose best days were in the past. I had no direction, no job, and no money. I didn’t know what I wanted to do, but I had a wife and bills to pay.

Luckily some income wasn’t far away.

A New Job

I’ve always been a go-getter. My customers and vendors alike enjoy doing business with me. I keep my ducks in a row, and when I need a favor, I’m always sure to repay it.

No less than three hours after I left my father-in-law’s company once and for all, I received a call. It was a job offer from one of my former customers. They were opening a new location and needed to build a team. I accepted without much thought.

It was a pay cut (33%), but I didn’t have much savings, and I needed a job. So I took the first offering.

Soon I felt stuck—one source of income, enough to pay my bills but not much else. The benefits were subpar, and the opportunity for advancement was non-existent.

With any journey, the key is to take the next step.

Pushing Forward

I knew I didn’t want to spend my days working for someone else. I took a resource that I had at my disposal and kept plugging along.

I served nearly five years in the Marines, which entitled me to the GI Bill. With a helpful nudge from my wife, I re-enrolled in college.

I had no clear direction, so I chose a generic major: business administration, with a concentration in entrepreneurship. I wasn’t sure what would come next, so I started with what I had and took a step forward.

Photo by Olya Kobruseva from Pexels

Within a few years, my degree was in hand, but I still had no clear direction.

One thing I had learned in college was that I would need money to start a business. But the options presented for raising cash didn’t jive well with me. You could take on massive debt or enroll friends and family as investors. Perhaps, if you’re lucky, you could find an angel investor to help start a business.

But none of these sources sounded like viable options for me.

Since I started the new job, my pay had increased, and I was now doing a little better than just ‘getting by.’ Knowing I needed cash to one day start a business, I started saving about $50 per week from my paycheck. Looking back, it could have been $20 or $5 per week … the key is you have to start somewhere.

Once I saw my savings grow, it motivated me. I wanted to save more … But how? In the little spare time I had, I started to hustle.

I bought things at garage sales and clearance racks, then flipped them on eBay and Amazon. I drove Uber a few hours per week. Anything I could to make an extra buck. I tucked all this extra cash into a separate account.

Until one day I found an opportunity…

Side Hustle: Vending Machine

I scanned craigslist daily for businesses for sale. Maybe I could take over something existing?

One day I found an ad: Vending Machine, On Location: $3,000. I called and set up an appointment to see it. It’s located in the employee break room of a large hotel. The owner was bringing in $100 per week in revenue.

I scrounged up all the cash I had, but it was only $1,600. I convinced my wife to let me take the other $1,400 out of our savings to bridge the gap. With $3,000, my business was born.

Since it was in a hotel, I could access it 24/7. This allowed me to keep a flexible schedule, and it didn’t detract from my day job.

But with any journey, expect twists and turns…

The Learning Curve

There were a few issues. 

  • The previous owner used off-brand products that weren’t selling.
  • Some inventory didn’t sell through fast enough. So instead of selling everything, I was throwing products away.
  • There was also another competing machine right next to mine.

So I started fixing things…

In college, I learned the importance of branding. I switched to all brand-name products. The customer knows what to expect when buying “Doritos,” not so much with “Sam’s Cheese Corn Chips.” And sure, I would refund them if they didn’t like it, but was it worth risking $1 for something you’re not sure about? Who wants to hassle with a refund?

Considering the customer’s point of view made this an easy decision.

This is an important lesson. The customer’s always right. In this case, the customer only wanted the name-brand products. So, that’s exactly what I gave them.

Next, I needed to turn all my products to avoid the wastefulness of throwing stuff away. I figured the best way to do this was to expand the business.

I set an alert on Craigslist for more vending machines. I found another one, not as much volume, but the price point was much lower, only $1,000. This machine produces about $25 in revenue per week. The nice part … it sold the same snacks, so I could turn over all my inventory without throwing away anything.

I bought this machine with my American Express. Two problems solved, one to go…

The competing machine … but there wasn’t much I could do about that. So I focused on what I could…

Customer Satisfaction

As I filled my machines every 2-3 weeks, I would make small talk with my customers. I asked what else they wanted to see in the machine? 

One of the cleaning ladies asked for Peanut M&M’s. I added it on the same day and gave a few to the lady that made the request and her coworkers.

The next time I arrived at my main machine, it was the only one there. The competing machine was gone. I’m not 100% sure, but I believe I gave the customers what they wanted, and after a little bit, they only bought from me.

I still run those two machines, but the pandemic meant they sat idle for most of 2020.

Pre-pandemic, the machines brought in about $250 in profit per month. It comes out to about $50 per hour of effort, not too bad.

I paid off my credit card, put the $1,400 back in savings, and had some cash coming in free and clear.

Putting some skin in the game taught me several important lessons. It also meant I could now take on new expenses and grow my business.

The cash flow was great, but I still relied on the nine-to-five to earn a living. My goal was to change that.

Learning to Hustle

I found an incredible book that was the exact ticket I needed. “The $100 Startup” by Chris Guillebeau.

He promotes building business for yourself but not risking your future doing so. Start small, don’t hesitate to spend a little money, but don’t go broke on an idea. 

His thought process did jive with me. I knew it was much more palatable for our financial situation too.

The cash started to pile up. Within two years, I saved up nearly $5,000 from hustling, saving, and my vending machine business. I still didn’t know what I wanted to do. So I kept plugging away and saving up.

It was 2017 now, and the stock market was going crazy. Every stock was just going up and up and up. Nothing seemed to slow it down.

I had a small amount in an IRA, but I’d never actively traded or invested in the market.

I figured I had to start somewhere, so I started trading, and while I was at it, I started a blog about my experience. I shared every trade … the good, the bad, and the ugly.

2017 was a good year in the market. Nearly everything I bought went up. I traded big names like Tesla (TSLA), Amazon (AMZN), and Walmart (WMT). I also traded penny stocks, companies you’ve never heard of (SGMD, UITA, XXII).

It was a good year … My vending machines were profitable, and trading stocks was easy money … So I thought.

By the end of the year, I had about $25,000 saved up.

My blog wasn’t making any money, but it was fun to write, and I enjoyed it. So I kept the blog and the expenses. My vending machine profits more than covered the cost of the website. I continued to trade and grew a small following on Twitter … 2,800 followers at writing.

But it turned out that trading isn’t easy…

Learning to Trade

2017 was a great year in the market. Every idiot made money. I didn’t have rules, and I didn’t have a system … I just bought whatever was hot. I chased 100 tips a day, and they worked.

But that market didn’t last…

2018 was rough. I was learning that the stocks don’t just go up. There is also a rule called the Pattern Day Trader (PDT) rule. It mandates you have at least $25,000 in your account to trade as much as you want. Anything less, and you’re greatly restricted.

At the time, I was hovering near that magical number but having trouble breaking through.

Daily swings of $1,000-2,000 were common for me at the time. One day I decided that I grow my account beyond $25,000 once and for all. But the market had other ideas…

Learning to Fail

When you deal with the market, you must learn to take what it gives if it gives you anything at all. But you must never tell the market what to do…

The day I learned this lesson is a day I’ll never forget. 

The ticker was IGC. It had been moving in the pre-market and started flying as soon as the market opened. I placed an order for $3, but no fill. I bumped the price up to $3.25, no fill. $3.50 then $3.75 still it was moving too fast, I couldn’t buy a single share. Until…

BOOM! My order filled! 6,000 shares at $4.06. But the only reason my order filled is because the stock had finally reversed. The price was falling fast. Before I knew it, the price had fallen back to $3. I was staring at a $6,000 loss on paper.

I was stubborn and refused to cut my losses. It was a Friday, and by the end of the day, the loss had grown to $8,000. I held the position. I didn’t sleep that weekend. I tried to clear my mind by running, but it didn’t work. 

I studied my options, but I couldn’t figure out how to dig myself out of this hole.

On Sunday, I finally made a plan. I had to exit the trade and salvage the cash I had left in the account. Monday came, and the loss was now over $10,000. I had no choice … I had to cut my losses. I sold the entire position for $2.37 per share.

One lousy trade practically cut my account in half. I was devastated…

Learning to Trade

After that, I decided to take trading seriously. I enrolled in a course to learn trading from a pro. Tim Sykes is a penny stock guru with more than 20 years of experience. Learning from him put me back on track.

I’m not a millionaire yet, but I stopped losing money and once again have profits to show for my efforts.

Trading is not a full-time income by any means, but it has added extra cash to my savings.

My writing about the stock market would soon come full circle. And I’m still optimistic that I can grow trading into something more. But I know better than to rush it.

In the meantime, I kept moving forward.

Side Hustle: Write

If you can write something people want to read, it becomes an asset. But there are always costs associated with any business venture.

My blog wasn’t free. I bought a domain name, spent a few hundred dollars putting together a decent website, and paid an editor. The project lasted for nearly three years and never made a dime.

Over three years, I spent about $2,000 on the project. My advertising revenue and affiliate sales are under $500…

Not exactly the extra source of income I was looking for.

I also wrote an eBook about transitioning to a gluten-free lifestyle geared to those who don’t cook. It’s something I experienced and saw a need for. To date, it cost me about $500 and generated $85 in revenue—another little money pit.

Maybe I wasn’t cut out for writing. Maybe it was time to cut my losses…

But I decided to keep at it. My expenses are minimal. The vending machines have paid for everything. So at the end of the day, I’ve lost nothing, and I’ve had some fun along the way.

I decided to keep writing but without a monetary goal. I cut the unnecessary expenses from my blog and kept writing. From now on, writing was just for fun.

That’s when another door opened… 

Side Hustle: Paid Writing

To develop my trading skills, I attended a three-day conference in Orlando hosted by Sykes.

On the second day of the conference, they made an announcement. They are actively recruiting writers. They needed help with their blog. I tracked down the head copywriter and shared my blog, book, and enthusiasm for the stock market.

I had to follow up a few times, but eventually, I landed some paid writing gigs.

I started at 12 cents per word. Writing one 2,000 to 3,000-word post a week paid $1,000+ per month. It took me two months to make back all the money I spent training myself to write.

Over the next two years, I wrote for them consistently. In my second year, I earned over $50,000 from this one contract.

You never know what tomorrow might bring…

Never Give Up

If I can offer a single piece of advice to any budding hustler or entrepreneur wannabe out there, it’s this … Start something!

I didn’t have the foggiest clue where my journey would take me. I didn’t know I could make $1,000 per month writing part-time for someone else’s blog. Everything I learned along the way brought me to the next moment.

If you are looking to start or grow a business and have limited resources, the best thing to do is take a step forward. Don’t worry about the rest. You need to learn, and the best way to learn is by doing.

Working for yourself is hard. There is no boss to give you direction when you fail. No one demands that you produce something by the end of the day. You’re accountable to no one but yourself. It’s essential to continue to push forward at all times. Failures are learning experiences.

I don’t fail anymore, but I learn a lot!

Tomorrow’s Coming

As of this writing, I’m negotiating with the hotel to put vending machines on the guestroom floors. That could generate $30,000 per year or more.

My trading is coming along great, and I’m consistently profitable. Though the profits are small, my trading record puts me in the top 10% of traders out there. Big profits require the top 2% … It’s a work in progress. Gotta keep moving forward!

By the beginning of 2021, my writing had become my main hustle … I ditched the nine-to-five!

But wait, there’s more!

My New Brand

This post serves as the jumping-off point for my new brand. I want to introduce myself to you … The ones who are trying to learn the market from the ground up.

Here are some unverified stats:

  • 80% of traders are out of the market in two years or less.
  • 90% of traders lose money.

In the market, the odds are against you. But it’s not about luck, and it’s about working hard. It’s about not giving up when you lose half your account. It’s about learning the lessons the market inevitably teaches you.

Trading for Keeps

My new brand, “Trading for Keeps,” continues the mission I started with my first blog post. Provide free resources for new traders and share my experience: the good, the bad, and the ugly.

Trading isn’t easy. Some of the smartest people in the world don’t make it on Wall Street. Most who read this don’t have what it takes to make it in the long run.

To the few who have what it takes: I hope the lessons I share inspire you and become stepping stones on your journey.

Sign up here to stay dialed in to all the latest offerings from Trading for Keeps. Plus, you’ll receive my daily watchlist with market notes for free.

There are podcasts, live trading, and blog posts. Please don’t hesitate to reach out with questions or to share stories of your own. 

We’re all strong together.

Step forward and prosper,


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