Everyone, prepare to be angry at me.
2005 - Took my OSAP loan, invested in a company called Timminco when it was $0.38 cents. Bought about $2000 worth. Bought $2000 worth. Sold the entire lot at $16. Paid off my OSAP loan right away. If you're keeping track, this netted me $72K pretax. Take away about $7K for tax. Paid off my student loan. Timminco btw was a fraud. The company was exposed as such in the wake of the 2008 housing implosion. It was a solar energy company.
2006 - Discovered a company called Rally Energy for $2.20 on the TSX. Was an oil company. Invested about $5K in it. The company ended up being bought up by a middle eastern oil company for around $8 a share. My second major score, netted $15K profit here. Take away cap gains, it's about $12k after tax.
2007 - Bought my first condo. It was a converted loft factory in a poor neighbourhood in Montreal. Bought it prebuilt at a discount. Cost was $135K. Put down $50K to buy it so my monthly expenses were very low.
2008 - Dropped out of school. Got a job in the public sector as a low level employee. Defined pension. This comes into play later. I'm not working a very glamorous job but I'm debt free at this point and living within my means. Building equity and credit. Would pay off my condo relatively quickly.
2011 - Went deep in a big a poker tournament for $23,000. Cashed out $20K. Ran the remaining $3K up to $35,000 playing mid stakes PLO cash games. Cashed out $20,000. $10K was left on Full Tilt Poker, lost $8K of it. Black Friday happens, Full Tilt Poker steals $2k of my money. Would not be able to recover it for two years after but I've heard of guys being stuck 6 and 7 figures on Full Tilt so I'm one of the lucky ones. Once I got my money back from Full Tilt, I ended up losing all of it on Stars anyways because I'm a degen.
2015 - Leave my job in Quebec. My defined pension at this point has just over $12K in it. Sell my condo which at this point was 90% paid off. Sells for $220K. I end up keeping most of it. Add that to the pool of money I've collected over the years. Moved to rural Ontario. Started buying plots of land in cottage country with my old man and began building houses and selling them. Was just a three man operation - me, my dad and my younger brother. I funded the projects with money from the sale of my condo.
2016 - Started buying Ethereum with my pension. My average cost basis was $37. I have a sizable stack still. Sold most of it off at $300/Ether though. Was regretting it in 2017 but thanked my lucky stars in 2018.
2018 - Got a job in Toronto in the field that I worked in Montreal. Felt like it was time to move back to the city I was born in. Just entry level office work but I live within my means.
2019 - Will likely buy my first Toronto property, aiming for a rental multiplex unit in the $1.5-2m range.
My household income is $53K. But I've gotten extraordinarily lucky several times in my life and I live within my means. I have very low monthly expenses. Travel on the cheap, mostly just stay in Canada. Last time I left the country was to Southeast Asia which is a very cheap trip. Don't own a TV, don't play video games. No media subscriptions. I pirate just about all my media. I occasionally do drugs but not often. Don't go out to eat much. Don't eat that much meat when I'm at home. Am not good looking enough to be going out on dates regularly. Have access to high end gyms for little to no fees due to some connections.
TL;DR - Gamble, got lucky. Live like a degen.