This Guy Built a $90M Company on YouTube in 2006

We're still surprised people did this but... 50+ founders worth $10M to $4B reveal their personal finances. Here it is: https://joinhampton.com/mw-wrWhy do we do this? Because if you're an aspirational person or someone who runs a business and is making money, it's incredibly challenging to figure out what to do. Information is impossible to find — and that's what we put together: the net worth reveal and why we do this podcast, Moneywise.He took a second mortgage to keep WatchMojo alive. Today he's worth over $100M and is trying to buy a baseball team.Ashkan Karbasfrooshan is the founder and CEO of WatchMojo, one of the largest media companies ever built on YouTube. He started it in 2006 with a $282,500 check from the AskMen sale, racked up roughly $1M in losses by 2011, sold his retirement savings, took a second mortgage, and paid himself $32,000 a year for the first five years. Then the top-10 format hit, revenue went from $1M to $10M+ in a few years with EBITDA margins as high as 80%, and he turned down offers at $75M, $80M, and $90M valuations. In 2020 he sold 25% to Star Mountain Capital at a $90M CAD valuation. He still owns most of the company, and puts his net worth between $100M and $250M.This episode gets into what it's like to sign a second mortgage at a notary with no idea if you'll end up homeless, why he moved payroll to twice a month just to have two fewer panic attacks a year, the real reason he walked away from an $80M offer (it wasn't greed), and how saying yes to everything cut his EBITDA in half. We also go deep on how he actually invests now — $5M across 15 startups, two-thirds of his stock portfolio self-managed — why he still takes the $40-cheaper flight, and his current mission to bring the Montreal Expos back to MLB.Also, this podcast is made by Hampton, which is a community for founders doing on average $20 million a year in revenue. We saw a lot of these money conversations happening privately behind closed doors and we thought, "What the heck, let's make it public." If you are a founder, apply here: http://joinhampton.com/mwTimestamps:00:00 — Ash's background: born in Iran, raised in Montreal, and why "the self-made man is a myth"02:50 — 31 jobs and the reluctant entrepreneur: "Wall Street is not rolling out the carpet for anybody named Ashkan"07:03 — The AskMen exit: a $282,500 check at 27, plus ~$150K when News Corp bought IGN09:18 — Why he bet on YouTube in 2006: "You don't go to war with the army you want, you go to war with the army you have"14:23 — The dark years: $1M in losses, selling his RRSPs, and the second mortgage16:14 — "I made payroll twice a month instead of every two weeks because I wanted 24 anxiety incidences, not 26"18:24 — Being early vs. being too early (and the Quibi problem)20:37 — The hockey stick: $1M → $3M → $5M → $10M revenue, 67-80% EBITDA margins23:25 — Paying himself $32K a year for the first five years24:59 — The 2012 offer he almost took ($3.5M + earn-out) and why he was relieved it fell through28:32 — Turning down $75M, $80M, and $90M valuations in 201730:36 — "I was like a drunk sailor at a bar saying yes to everything" — EBITDA falls by half31:39 — Why walking away wasn't greed: the call-option trap he saw coming32:58 — The 2020 deal: selling 25% to Star Mountain Capital at $90M CAD37:54 — Net worth reveal: "anywhere from 100 to 250 million"39:03 — Monthly spend, paying off the house, and $5M into 15 startups43:37 — Was the deal life-changing? "More mindset changing than life changing"44:34 — What he never shares about money45:34 — The Montreal Expos comeback plan: "It's not impossible, it's improbable"Sponsors: Daily Body Coach - achieve your dream body with https://moneywise.dailybodycoach.comSubscribe to Moneywise: https://www.youtube.com/@themoneywisepodcastFollow Daniel on X: https://x.com/danielcberkListen on Spotify / Apple Podcasts: [search "Moneywise Hampton"]