I have been properly self employed with no other income propping me up since 2006, but have had side hustles since well before it was cool to do so. Even though back then I didn’t know what my business obsession was. Hobby business maybe? Who knows.

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My first hustles were in my teenage years. I loosely figured out how to install car stereos. I was absolutely not qualified to do this, but no one stopped me, until I tried to do an install for a friend and it didn’t work and I enjoyed a lesson in not doing things I was not qualified for. Sadly, I had to fail a lot harder before this lesson would really set in.

Since then, I’ve started, failed, sold, approximately twenty businesses. Since my ADHD diagnosis, I learned that having so many business interests isn’t your standard way of living and so I got rid of pretty much all of them. I now just have this writing I do for funsies, and my main business - a PR firm with my business partner, David Cormack.

There are two main influences that helped me get started

1. My parents have been self employed for as long as I’ve known them, and even before then. They are the ultimate small business hustlers. Buy a business, do it up a bit, work in it, sell it, and repeat. Not massive exits worth millions. These are simple, small businesses delivering a product or a service. My parents did this over and over across a number of industries, and they made it look easy and so I’ve always believed it was.

2. Being perpetually bored because of undiagnosed ADHD meant I was always looking at other opportunities, other things to do, other things to try. People with ADHD have faster brains. Sometimes so fast, that the story we’ve told ourselves about an idea or a concept, has whirled around the brain at such a speed, the fear of starting a new thing doesn’t really exist. We just believe we can do whatever we want to do.

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But suppose you are not the product of hustlers, nor do you have ADHD. You can still be your own boss, you’ve just got to have a really really good idea, or have enough experience in your field to quit your job and go out on your own.

A really good idea has to be something that people want that they can’t get easily from anywhere else. You’ve probably heard this a million times before, but it’s so important.

I’m lucky now that after all my many fails, I’ve ended up on my feet, and with a successful business in its 8th year of operation. It is definitely easier to run a business with someone else. Ideally someone you trust is a good start, but DCG was essentially started by two people who didn’t really know each other at all and it has turned our really great.

But prior to DCG, there wasn’t always a gap in the market of the businesses I wanted to do. Some business ideas I had were too future for actual customers to want (see the futuristic weird thing below). And those were the businesses that crashed and burned in a spectacular way.

LouLaBelle’s was by far my biggest failure. It was a beauty studio focusing on hydrotherapy massage. We were based inside the old Chase Plaza on Albert Street. I tidied up an old retail space as best I could and had a tanning machine in one room and usual beauty things - waxing, nails, facials etc in the other. And in the main room, the pièce de résistance, 2 enormous spa capsules that looked a bit like this.

To be fair, the actual hydro massages were really good. I had several chronically stressed people working in neighbouring towers come to me every day for 10-20 minutes. But not enough custom to make a successful business. Also, a big bummer that I wasn’t a beauty therapist at all so had to hire staff for that part. All in all, we just weren’t making the moolah to stay open. Shit is expensive and so if there was one piece of solid advice I could give you it is:

Do the math before the business. Have the savings to fall back on. Whatever you think your business is going to cost you to start, double it and you’ll be a bit closer. Side hustles became a thing because people upping sticks and starting their own business without their usual income is a terrible idea. I quit my job and it was entirely the wrong thing to do. I should have asked to reduce my hours or perhaps not sign a commercial property lease or expensive equipment lease without some proper guidance. My job at the time was an utter pill. So I had to leave eventually. But Loulabelle’s as fun as it was to start up really wasn’t the best exit strategy.