I’ve tried many businesses and side hustles over the past 15 years. I’ve mowed lawns, was a DJ at weddings, negotiated real estate deals, started an e-commerce business, and many others. Some of those endeavors made me money, but others didn’t.
Now I have a successful digital marketing agency. People often ask me how I did it.
My business failures taught me a few things along the way. Hopefully, you can learn from my mistakes.
Do the work
In 2014, Elon Musk gave a commencement speech at USC. His advice to young graduates hungry for success? He told them to work 100 hours per week.
He said, “Work hard, like, every waking hour… If you do the simple math, say that someone else is working 50 hours and you’re working 100, you’ll get twice as much done in the course of the year as the other company.”
Looking back, I can see one obvious difference between my ventures that were successful and those that weren’t. It’s that I worked much harder at the successful ones.
People like to complicate entrepreneurship. However, in my mind, it’s actually quite simple. All you have to do is get customers and deliver products. That’s it.
During the Great Recession in 2009, I had a very hard time getting a job. So I asked myself, what do I know how to do? What will someone pay me to do?
I literally wrote out a big list. It included the simplest things, like doing the dishes and finishing homework. My goal was to create a business that earned me more than a $10-per-hour job.
I settled on mowing lawns. I figured if 14-year-olds do it, I could, too.
I literally threw my mom’s lawnmower in my truck and started knocking on the doors in my parent’s neighborhood. (It wasn’t a wealthy neighborhood, by the way.)
Within a few weeks, I had enough clients to keep me working part-time, and I was making about $1,000 per month. My time doing the work averaged about $30 per hour. Not bad for a bootstrapped side hustle!
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Don’t quit
That little lawnmowing business put food on my table for a few months, but I literally walked away from it overnight when another opportunity came along.
That other opportunity was in the form of seasonal 1099 contract work. In California, paid signature gathering is big business every election season. I made about $1,500 per week working as a full-time political canvasser, while the work was available.
My family couldn’t believe that I quit my lawnmowing business for seasonal work. My grandpa asked me, “Why don’t you just keep your lawn mowing business on the side and do both?”
He was right, of course. But I didn’t want to work the long hours required for doing two jobs. In retrospect, there was momentum with my lawn mowing business that I shouldn’t have ignored. If I had persisted with it, maybe I could have built up a pretty big business.
Who knows where it might have gone?
More than 50% of the money that an entrepreneur makes in a business happens when they sell it. Let that sink in for a minute, and you’ll see why you should never leave a business without selling it first.
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Build your credit
After the political canvassing season ended, I turned my interest to real estate. In 2010, the market was bottoming out, and I knew it. I figured if I could get a few loans and raise some capital, I could buy up a lot of houses on the cheap.
The math was highly encouraging. At the time, three-bedroom houses in the neighborhood that I grew up in were going for about $130,000 apiece. The monthly mortgage payment on a 30-year loan would only be about $600, and those same houses were renting for at least $1,000 per month.
It was a unique opportunity. The only question was: Where would I get the money?
Due to bad choices I had made the previous year, my credit was shot. Unfortunately, none of the family or friends that I approached would let me use their credit, either.
After unsuccessfully looking for potential partners with credit or capital in my personal network, I gave up.
Giving up was a huge mistake. I ended up missing most of the real estate swing in the last decade.
Later in my career, I learned how to raise capital and eventually fixed my personal credit. And even better, I learned how to build business credit, which at the time I had never even heard of.
Research shows that 45% of small business owners don’t know they have a business credit score. Yet for many small businesses, a good business credit profile could be the difference between success and failure.
Credit is one of those things that you have to build before you need it. Many well-run small businesses don’t need financing for their day-to-day operations. But if the need arises, a few low-interest lines of credit can make all the difference.
Now my credit scores are all in the 800s and have given me access to tens of thousands in low-interest financing for my business.
Build a team
Self-employment is great, but it has its limits. If you want to grow your business beyond a small operation, you need other people to help you get there.
Hiring is one of the most daunting facets of business ownership for most people. Yet it doesn’t have to be nearly as complicated as it seems.
In my current business, I don’t yet have any full-time, W-2 employees. Yet I have a full-time contractor working for me in India on the other side of the world, a part-time editor, and a team of freelance writers that I rely on heavily.
Contractors, virtual assistants, partners, vendors and suppliers can all be integral parts of your team before you make that first full-time, in-house hire.
Flexible work arrangements are super popular right now. If you can provide good opportunities for other people, they’ll treat you right.
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Create systems
A business is nothing without workable, scalable systems. You need your business to run like a well-oiled machine, and that takes some configuring.
My favorite books on this subject are small business classics: “The 4-Hour Workweek” by Tim Ferriss and “The E-Myth” by Michael Gerber. If you find yourself trapped in running your business, both of these books teach you how to build systems that take you out of the day-to-day operations.
Your team members aren’t going to train themselves. You need standard operating procedures, written guidelines, training videos and clear expectations.
I created dozens of training videos for my team that document everything they need to do. We have weekly project management “sprint” meetings where we review the work from the last week and plan the work for the coming week.
And most importantly, you need systems that help you stay accountable to yourself. If I have a difficult long-term project or goal, I give myself short-term deadlines along the way.
Without short-term deadlines, you can forever procrastinate the non-urgent. Before you know it, a year has gone by, and you haven’t achieved anything of importance.
The me of 10 years ago never would have done what I’ve achieved now. My “wantrepreneur” self procrastinated hard things, quit too early and got distracted easily.
If you’ve been struggling as a wantrepreneur, know that you’re a lot closer to achieving your goals than you think. Follow these steps, and you’ll be surprised at how quickly your business can grow.
