I am truly blessed. I bought a business on eBay during the .com crash of 2000 (esnipe.com) and turned it into a moneymaker. From there I am gone into investment in domain names and real estate.
I’ve also failed a lot, like the time when I spent $1,400,000 of my own money trying to beat craigslist.
I think I've met your doppelgänger, but on the east coast. I won't mention his successful business, but I know he spent at least $1.4MM trying to re-create Adobe Flash... for Android... in 2015.