How I Went from Selling Weed at 15 to Founding a Startup at 42

I was always a restless, creative type. Sitting down absorbing information with no practical or creative outlet has never really been my style. I like to learn and put into practice at the same time. I learn faster, and am much more interested in what I’m doing if I can actually try it out for myself.

I was pretty bored in high school, as I usually found myself ahead of most of the class and it was mostly rote learning anyway. So when a friend introduced me to smoking weed at around the age of 14, I quickly took a liking to it as it alleviated a lot of the boredom I was experiencing at the time.

We were living in the countryside, and the same friend brought me over some marijuana seeds one day. I very quickly took up a passion for horticulture, and seeing as we lived on a big property, my parents weren’t any the wiser.

Around the same time, a lot of my friends, who still lived in the city where I’d grown up, had also found pleasure in the green herb. When I showed one of them my crop he couldn’t believe it. “That shit sells for a fortune in the city,” he said.

I had just started working at a local supermarket to make myself some extra pocket money, and was being paid about $14/hr, which I thought wasn’t too bad at the time. But when my first crop was harvested, and I sold a few ounces fo my friends in the city and made a couple of thousand bucks in a weekend, well, let me tell you… My whole perspective on life changed.

My parents had always worked for a wage, and they’d never seemed very happy about it. They never had the kind of time for themselves that they would have liked, to dedicate to things that really interested them. My father was a teacher and my mum a nurse, so they spent all their time looking after people who weren’t really in the best position to appreciate it.

Having worked myself for a wage for a few years also (before the supermarket I was a paperboy earning $15/week), the realisation that there was a much better way to earn money than simply slaving away for it was a total game changer.

I started studying business management at school, invested in the share market, and started another (more legitimate) business, importing Dr Martens shoes from the UK and selling them to my high school friends (this was in the ’90’s and the grunge scene was just starting to get big).

Apart from the fact that I wanted to become a full time entrepreneur, I learnt a few other important lessons from my days selling weed in high school:

  1. Find a product with a high profit margin
  2. Don’t sell directly to the public if you can avoid it — selling in bulk is much easier (I never sold directly to anyone except my friends, and they were the ones who divided it up and sold smaller quantities — or just smoked most of it!)
  3. Cash is your best friend!

After high school I travelled the world for a few years — calling both Mexico and Japan home — but I eventually wound up back in Melbourne.

Travelling was exciting, and I somehow wanted to replace that travelling buzz with something that would give me the same kick, but wouldn’t leave me poor at the same time.

Apart from being an entrepreneur, I’d always wanted to be a science fiction writer, and while I was travelling I’d started working on my first book: Perfectible Animals (now available on

Writing was a great lifestyle, but it wasn’t really paying any bills, so now seemed like a perfect time to start my next business — a Latin dance school! I’d learnt to dance while living in Mexico and my partner at the time was a great dancer, so we started it together.

I loved it. I loved the creativity and constantly thinking on your feet that running your own business requires. You never know where your next pay check is coming from, so you’re always hustling, always finding new, creative ways to get new customers or keep the ones you have already.

I was only about 22 at the time, so having my own “real” business felt fantastic (neither selling weed nor Dr Martens had ever felt like a serious business).

It took me quite a while to get used to the uncertainty, though. And even today I’m not 100% used to it.

I’ve gotten really good at telling myself that whatever happens, I will somehow work it out, though. And I’ve also learnt to trust myself, my own ability to manage difficult situations, and to find creative solutions.

If you’re thinking of going into business, these are essential skills. Because suddenly you are 100% responsible. The buck stops with you. Nobody else is going to clean up the mess, or find a solution for you, even if everything goes to sh#%!

So, if you like reliable days, where you know what’s going to happen, have no surprises, and don’t ever have to take drastic action at a moment’s notice, then building a business is probably not for you.

However, if you’re like me, and love variety, love excitement, love creativity and inspiration, and feel suffocated by having to do the same boring thing every day, then you’re well on your way to being a perfect candidate for the entrepreneurial life!

My next business, at 27, involved selling software and websites on Ebay.

Ebay had just launched, I had just learnt to design websites, and I’d bought a small piece of software that helped you create a basic membership site. I built one site after the other and sold them for $100-$300 each, which quickly turned into a thriving business.

I started selling the software directly from my own website, by running campaigns on Adwords, but eventually that business got shut down when Paypal decided to suspend my account. The software had some MLM features built into it, and they said it was against their terms of service.

It was a nasty lesson — so be careful if a large part of your business depends on a third party. If they make changes, then you might find yourself quickly out of business as I did.

Lesson 4: Be prepared for anything and have confidence in yourself that whatever happens, you WILL find a solution of some kind.

I was living with my girlfriend at the time and almost our entire weekly income depended on that business, so to have it suddenly shut off was a bit of a shock! This was probably my first experience of having the rug pulled completely out from under my feet in a business (there have been many examples since then!)

My girlfriend had been teaching Spanish to some local students and there seemed to be some real demand there (this was way before Duolingo), so we spent the next few weeks walking around the local universities putting up posters for Spanish classes.

One morning I was chatting to a friend of mine about our situation, and he suggested that we start running ads on Adwords for our Spanish classes. People were just starting to use Google and although I’d done well out of it by advertising my software business, I’d never really thought about applying online marketing to a bricks and mortar business. It just wasn’t really common in those days yet (this was 2003).

Anyway, I decided to give it a try, and I built a website for our “Spanish School” (which didn’t actually exist yet) and ran an Adwords campaign for it.

Boom — within a few hours we were getting calls from students wanting to book in!

We quickly hired a room in a local hall and had a couple of full classes before we even knew it.

Within 4 weeks, we’d hired another teacher!

Thus The Spanish Cat was born, which is still one of our businesses to this day.

Business lesson 5: Smoke and Mirrors and the MVP are your best friends. When creating a business, do it as cheaply as possible to start with to judge if there is any interest there. If there is, you’ll know about it pretty quickly. If there isn’t, then you haven’t wasted too much time or money. Some of my biggest business failures have been when I didn’t apply this lesson and spent a lot of money building a business before even testing the concept.

The Spanish Cat was almost too successful. Year upon year we made more money than ever before, almost effortlessly, and I started to get the impression that I had a Midas touch and could do no wrong. We opened schools in London, Mexico, and were about to open one in the United States.

But by this time the world economy was slowing. Then the GFC hit, and almost immediately our profits dropped by about 30% and continued on a downward trend for the next 5 years. We had to either shut down or heavily downsize all of our schools.

At the same time, apps were becoming more popular and everyone started using Duolingo. Duolingo is not the best way to learn a language, but it still managed to kill about another 30% of our student base!

Business lesson 6: Just because things are going well, doesn’t mean they always will. Businesses have a life cycle, and if you don’t stay on top of new trends and technology, there is a big chance your business will not survive forever. At the very least, it won’t remain the same. Be prepared for this change before it happens and don’t spend years, as I did, trying to scrape to make ends meet while you re-structure everything to match the new conditions.

During the years that I was running The Spanish Cat I was also doing a fair bit of freelance web design work. I enjoyed building websites, but I hated dealing with customers. People get very fussy when it comes to their websites, and making constant tiny changes started driving me crazy. I did some digital marketing work as well, but didn’t really find it that fulfilling. If my heart isn’t in something, I find it hard to keep going when the going gets tough.

Business lesson 7: Make sure you’re doing something you love and believe in, or it’s very hard to keep up the motivation when things get difficult — which they invariably will.

My next “real” business was a bar/restaurant in the centre of the city in Melbourne. As with my other successful business ventures, I started very small with this one. Some friends, along with my wife and I, started running some small parties. Well, we thought they were going to be small. The first one had over 300 people packed into a tiny office space that we’d fitted out for the occasion by covering the walls with posters and building a tree (yes a tree) in the centre of the room.

The parties were so successful that we decided to find a proper venue for them, and thus VAMOS was born. It has evolved over the years from a party venue to a really nice tapas restaurant and cocktail bar (we’ve grown up!) and the four of us still run it to this day.

Business lesson 8: Never open a restaurant! They are the stupidest type of business in the world. Honestly, potato farming would probably be easier. The profit margin is tiny, the amount of work is huge, and chefs are nuts! Also, you’ll probably become an alcoholic from dealing with the long hours and the easy access to alcohol.

After Vamos was up and running, I decided to go back to online businesses, where I wouldn’t have such direct contact with customers! I actually had three ideas at the time: a hospitality hiring app, a booking engine for classes and workshops, and a social network built for the crypto community.

I started doing market research and created MVPs for all three of them. I also enrolled in a startup incubator with the Founders Institute.

The first idea was a complete flop, the second one got a bit of traction but wasn’t really that successful, and the third one took off like a rocket. It seemed the demand for information about the crypto and blockchain space was huge, and people in this community were interested in having a social network dedicated just to them. Plus — I was offering people the chance to earn crypto from creating content.

Business lesson 8: Good market research is even more important than an MVP. Seriously, you can hardly do too much of this stuff. During the FI course we had to do long form interviews — which meant contacting total strangers in the industry we were interested in working in and asking them for an hour of their time. I was petrified at first of doing this at first, but people were so responsive and helpful, and the information I gathered was so rich, that I actually ended up doing more of these than I needed to and they really helped to refine my business plan.

Anyway, that’s how it all started. That’s how I ended up becoming the founder and CEO of Trybe brings together my interests in teaching, in writing, and in technology — particularly web technology and cryptocurrencies.

And I haven’t looked back.

In less than 6 months we now have over 20 staff, many of whom are full time on the project, and we are about to launch a new web app and some mobile apps a bit later in the year.

We’ve survived being hacked, being scammed, and having way too much traffic for our website to handle. Somehow it’s brought together a fantastic bunch of passionate people.

I always wanted to create something of value, not just for myself but for the world at large, and I think the way people create, receive, and share information has been distorted by existing social networks. We need something that actually educates people, rather than just giving them mindless entertainment. And something that connects them at the same time.

This world is in trouble — and if we are going to save it then I believe we need to educate ourselves and work together in ways that we have never done before.

And maybe, just maybe, technology can help us with that.

So — there you have it. A brief history of my journey from selling weed in high school to running a tech startup. And even though I’m probably poorer now than I’ve been in a long time (building a new business always requires you to spend way more money than you’ve got, and deplete both your capital and your income down to almost nothing) I’m probably happier than I’ve been in a long time.

I love this project. It brings meaning and purpose to my life.

And that is worth more than anything.

If you’re interested in reading more about the building of Trybe, read my previous blog posts here: How I built Trybe for less than $10K

Thanks for being part of this amazing journey with me.

How I Went from Selling Weed at 15 to Founding a Startup at 42 was originally published in Hacker Noon on Medium, where people are continuing the conversation by highlighting and responding to this story.

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