This one will probably be obvious but everyone seems to enjoy it when I tell it: I was hired out of college to work for a NYC-based startup called 'Games Media

This one will probably be obvious but everyone seems to enjoy it when I tell it: I was hired out of college to work for a NYC-based startup called 'Games Media Properties' that ran a video game tournament called the World Series of Video Games (both horrible names, I didn't come up with them). We spent roughly 300-400k per event to throw these huge productions, then another 1-2 million to film a TV series about it. There were 7 events, 3 in the US and 4 international. The business model was a mix of ticket sales ($80 competitors and $5 spectators paying to come in), and ad sales (pay and be a sponsor). Each event attracted around 30,000 attendees and we were asking for $1 million to be a 'title' sponsor of the series. You can do the math on your own, but it essentially equated to $1 million to reach 30,000 people (assuming there was 1 title sponsor per event). At the same time, we were building a few websites around the tournament. One for news coverage, one an actual 'tournament' site, etc. We had the idea to sell ads for our online sites with a near-inverse value proposition: Spend $30,000 to reach 1,000,000 people. Needless to say, we stopped doing tournaments about two years in once all the advertisers flocked to the online model. That company is now called Giant Realm and is an 18-34 male-focused ad sales organization that was recently acquired :)