From Broke Ottawa DJ to a NYT Front Page Mention: My Weird 15-Year Entrepreneur Journey

Alright, I’m gonna just type this out normally because the last few versions I tried posting keep getting flagged as AI (which is hilarious because it’s literally my life lol). Maybe this helps someone who’s been through weird ups and downs too.

So yeah… back in like 2009 I was DJ’ing around Ottawa. Nothing glamorous, mostly tiny gigs, bars, random events, whatever paid a bit. During the day I had a co-op placement through Algonquin in this Government of Canada department. I only did one year of the program and the co-op. I didn’t have some big plan or anything, I was kinda drifting between “this might be something” and “I have no clue.”

Then I had to go overseas for family reasons and when I came back the gov job was gone. No explanation, nothing. Just “position no longer available.” That one stung more than I expected because I grew up in co-op housing and we had constant money problems, so even a small stable job felt huge to me. Losing it just… knocked the wind out of me.

By 2012 things were rough. Ottawa winter, broke, confused, living with my dad. I applied for social assistance and got $800/month. Honestly that $800 kept me sane while I was trying to figure out how people made money online.

I’d spend hours every day looking up stuff like “how do people make money on the internet” and half of it was garbage. Eventually I ended up on BlackHatWorld and found this whole underground world where people were boosting YouTube views. I didn’t even know that was a thing.

I hired this small dev guy who automated it for me and suddenly my DJ videos were doing way better. Then I thought “ok maybe I can sell this.” So I made a Fiverr gig: 500 views for $5. And it somehow blew up. I started getting dozens of orders a day, then hundreds. I went from basically no income to $5–6K a month which, at the time, felt unreal.

Then Fiverr nuked the entire category overnight. No warning. Gone.

That was the first time I learned how fast an online income can disappear.

So I built my own site (badly at first lol) and taught myself SEO. Mostly from forums, random posts, trial and error. Somehow I ended up ranking #1 for big keywords and was suddenly making serious money… like, $30–40K/month sometimes. I bought a house, travelled, partied a lot. Honestly got ahead of myself.

By 2014–2015 everything started slipping though. Competition got bigger, algorithms changed, and my income dropped to $8–10K/month. Still great, but it felt like a huge fall mentally. I also made the mistake of giving too much money to friends and certain family members and that created drama I wasn’t ready for. I eventually had to cut most people off because it was messing with my head.

2016–2018 I partied too much and didn’t focus enough. Business kept slipping.

Then out of nowhere a New York Times journalist emailed me, asked if I’d talk about the whole YouTube views world. I said yeah sure. He actually flew to Ottawa and interviewed me for two days. A couple months later the story lands on the FRONT PAGE. Seeing my name there was insane and honestly stressful.

A few months after that my payment processor shut down my account and just like that I was back to zero income again. Another restart.

In 2018 I said screw it, I’m rebuilding this properly. Learned WordPress and web dev seriously. Built hundreds of websites. Not glamorous, but it kept food on the table. Then in 2019 my kid was born and that basically reset my whole mindset. I got way more focused and disciplined.

From 2019 to now it’s just been steady work. No viral success, no fast wins. Just showing up every day, building stuff, improving, getting clients slowly.

Last year I got into AI + coding and built an app from scratch. It gave me that same spark I had back in 2011 when everything felt new and full of possibility.

I don’t know where the next five years are going, but for the first time in a long time it feels like I’m starting something instead of patching something.

A few things I’ve learned:

• your first hustle is never the final one
• don’t depend on a platform for your whole life
• money makes people act strange sometimes
• reinventing yourself is part of this
• you don’t need the full map, just the next logical step

If you’re rebuilding or stuck, I’ve been there more than once. You can come back from way more than you think.

Anyway, that’s my story. Maybe it helps someone.