TaskRabbit

Slips: play the lottery from your phone with a TaskRabbit middleman

You can't legally run an online lottery, but you can pay someone to physically buy a ticket for you. Slips dispatches a person to a gas station, buys the ticket, photographs it, and custodies it digitally, bypassing the rules with a two-step process.

“What these guys did was they let you play the lottery from your phone legally. How do they do that? Well, basically wherever you are, you'll say, I'd like to buy a lottery ticket. And then they will physically go send somebody to a gas station. They'll buy the lottery ticket. So it's sort of like there's a TaskRabbit essentially that'll go buy the lottery ticket in person for you. 'Cause you can't actually buy them online.”

Steal thisFind an activity blocked from going online by regulation, then pay a human proxy to do the physical step so you stay legal.

The Penny Hoarder: a personal-finance blog that became a $50M affiliate machine

Sam recounts how founder Kyle started The Penny Hoarder as a broke college kid blogging about odd jobs, noticed Uber paid $2,000 per driver referral, and built it into a $50M/year content-plus-performance-marketing business by optimizing articles to drive affiliate signups.

“He started it as a finance blog where basically he was like a poor 20-year-old and he was doing like TaskRabbit and Uber driving and all types of odd jobs in order to make ends meet while he was in college because he came from a low-income household. He would blog about it. Eventually, this is his origin story. I don't know if it's true. He was like, "Oh, wow. Uber will pay me $2,000 for every person I refer to them. I'm going to write a little bit more about this and put more affiliate links." That's what he did.”