How I made my first million dollars —  the true story of 21 failed businesses.
7 min read

How I made my first million dollars —  the true story of 21 failed businesses.

How I made my first million dollars —  the true story of 21 failed businesses.

I wrote this post years ago, but talking about making a million bucks without sounding like a jerk is…hard. I’ve read hundreds of these stories on the internet, and most of them are bullshit. Anyone giving you advice on how to “make a million dollars” is trying to sell you a course.

This post has no agenda other than to shed some light on the meandering journey I took to business success. I do not recommend following in my footsteps, but you will probably ignore that advice.

I’ve been playing the business game for almost 15 years.

After hundreds of ideas, dozens of domain names purchased, and countless false starts, my most recent project has been more successful than everything else combined. It reached $1m revenue a few years ago.

Though it didn’t register emotionally at the time, it’s a milestone that’s worth reflecting on.

The path of entrepreneurship is not a straight line. There is no formula.

Your first idea isn’t going to work. Your next one, probably not. Eventually you might get better at deciding what is a good idea. And that good idea might work, if everything else falls into place.

It’s hard to build a company, but you don’t need to be a genius like Bill Gates or Elon Musk to be more successful than 99% of the planet. If someone like me can build a company, you can too.

I wouldn’t suggest doing what I did. But if you do, try to enjoy the ride.

Here’s how I’ve made every dollar — from zero to a milly.


My mom & dad paid me 7 bucks a week to do chores. I was pretty lazy.


My Nana paid me $20 to mow the lawn and water her plants in the summer. That $20 included tea, cake, and great conversations about life. Even when I no longer needed the money, I kept doing the job.

Tennis coach

I was officially employed at 14 as a tennis coach at the Crescent Beach Swim club. The perfect summer job, I worked there for 3 summers. My salary maxed out at 5k for 2 months of work. Not bad, and I got a great tan.

This is the only full-time job I’ve ever had.


I made minimum wage as a dishwasher once a week while coaching tennis. I lasted a month. Dishes were not in my future.

Web designer (round 1)

I started making websites for a few family friends and people I worked for using Weebly in high school. It's a business anyone can start, now.

Car flipper

2Gs baby!

In 12th grade I bought a VW Jetta with a friend from the US and sold it in Canada for a $2000 profit. I was late for my grandparents 40th anniversary celebration because of the border lineup. I still feel bad about it.

We did not repeat this experiment.

Tree chopper

This involved chopping trees and trimming hedges at wealthy people’s homes. I made $20/hr plus occasional tips. I didn’t mind the manual labour.

Chair counter

I worked for UBC Classroom services for a year a part-time chair counter. Our job was to go to classrooms and see if the number of chairs they had matched what our sheet said they should have. If they didn’t have enough chairs, we moved chairs over and marked the sheet with a -1. Hours were self-reported.

This was my first experience with true passive income.


I just remembered this looking in my inbox for evidence I was in fact a chair counter. Apparently I started a moving company on Craigslist with a Zipcar truck for a few months during the school year. I made $1200.

Window cleaning franchise manager


I was one of the first franchisees of Panorama Window Cleaning. Essentially College Pro painting, but for window cleaning. It was a great business that did $40k in revenue in 4 months, and taught me many valuable lessons.

I had 2 employees, and did everything from sales and marketing to manual labour for the first three months of the company. Even when I broke my foot in a Jet-ski accident, I continued to do sales. I must’ve worked hard that summer, because we did well. I recommend anyone who thinks they might want to start a company to try out a franchise business.

Financial services cold caller

I made cold calls for Dundee Wealth Management in my boxers from my dorm room in third year university. I wasn’t very good at it.

Ponzi Scheme Scam Artist (Almost)

Thank goodness a family friend realized this was a complete scam, but I almost got caught up in a web of lies selling fake art to middle class people.

Window cleaning titan round 2

Lacking options, I started my own window cleaning company — High Definition Window Cleaning — with a friend. It did ok, but the most telling sign was turning down a $50k contract to go work in Ottawa because I would have to be available in the winter. I could’ve built that company to over $100k in revenue in year 2, but window cleaning was not my future.

In two months I cleared $10k in personal profit.

Production Assistant

The final two months of the summer, I went to live and work for a TV production company in Ottawa. I was a production assistant. I helped carry stuff, setup lights, and drive things around. I got bored as hell after a month.

Depressed and lonely, I quit to go drink in Europe.

Energy efficient venetian blind designer

My final year of University, I joined a class called New Venture Design that paired up business and engineering students. We designed an automated venetian blind that tracked the sun and reflected natural light into the ceiling. We won $15k in business plan competitions, and decided to start a company with that huge windfall.

Zipcar street team member

I lasted 5 months selling Zipcar memberships on the street to passersby. I was slightly above average at it, but did not enjoy it.

Composting mogul

During that time, I also thought that office composting was a good idea. A week later I launched Urban Dirt to pick up people’s compost and use it to make fertilizer. I had a quick trigger finger. My second week in, I cold-called the Operations Manager of Rogers Arena and got the meeting. I put together a passable pitch and was invited to bid for the entire building composting contract.

We didn’t get that deal.

Unfazed, I built the business to a whopping $200 in monthly revenue, including $20 of fertilizer made from coffee grounds we sold at a farmers market.

Web Designer

Wisely, I quit composting and decided to go into web design. My business partner and I threw up some Craigslist ads and made a bunch of websites for people. Clients included Woof It Up Dog Training, Little Rascals Daycare, and a few startups.

Financial blogger

As another supplement to our whopping web development income, my business partner and I started blogging on Seeking Alpha about buying stocks. We cleared $800 in a few months, despite the fact that I had $5k to my name and owned no stocks.

Apple’s Future Is In The iCloud (NASDAQ:AAPL)
Much of the discussion recently around Apple (NASDAQ:AAPL) has been about the release of an iPad competitor from Amazon (NASDAQ:AMZN), and the the release of th

Various bad ideas

Over the course of two years, we tried a bunch of very bad ideas. An events listing website for Vancouver (, a platform that connected students and businesses (, a Wordpress template directory listing (, and many more.

I’ve blocked plenty of these ideas from my memory.

To my credit, the best idea I’ve ever had (still) was Classpass before Classpass.

Damnit, I should have pursued that one.


Getting out of the web design business, we decided to build a product. We built KarmaHire — a copycat product of a few interesting recruitment software products. A very long story short, we ended up on a 2.5 year ride through a startup accelerator, raised a quarter million dollars, and ultimately failed.

In that time we built 4 products. Three of them generated revenue:

  • A recruitment marketing platform ($25k revenue)
  • An applicant tracking system ($10k revenue)

The years trying to build this business were formative. I went from a recent graduate with no experience to “CEO” of a funded tech company. I learned a ton about product development, marketing, hiring, and fundraising.

I also wasted so much time on bullshit startup things — desperately trying to push a product to customers that didn’t really want it, telling stories that were objectively true but not really true, and trying everything to survive.


We’re 3 years into my latest business. It’s a simple online resume builder with grander ambitions. Things are going well.

Our monthly revenue equates my total revenue from the last 5 companies.

We hit $1m in revenue within the first 2 years in business.

I still don’t know much, but here’s what I do know.

The truth is it takes a long time and many stupid ideas to build anything marginally successful.

Start very small. That first $10 that you made out of thin air will change your life.

And finally… try a bunch of stuff.

It’s not complicated. It’s just hard.

Like I said, no agenda. Follow me on twitter I guess?

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