Andrew Mason wasn’t a puppet in this scheme, but he was ‘the product guy.’ The business stuff — the massive expansion, t

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tart is your cost of living. Dividend stocks don’t pay for your retirement. They pay for a certain amount of your expenses. If you have extra money left over from your dividend payments after factoring in all expenses, you’ve retired from dividend investing.

“A lot of the examples that got me most excited, like the idea of building a dome over the city of Chicago which is something that if you had a way to go to everyone in Chicago and say, what would it be worth to you to make the winters here obsolete, people would say like, I don’t know, $10,000. Everyone would. Before you know it, you would have billions and billions of dollars for this project.”

When it finally launched, Andrew spent the bulk of the $1 million on search engine marketing — targeting specific social campaigns. The result? An embarrassing 1,000 hits per month, most of whom were online trolls looking to legalize weed.

The first deals were slow and labor-intensive. They required a lot of hands-on selling. But when Andrew sold 500 Groupons to a sushi place weeks later, he knew he was onto something.

The idea was that if enough people pledge to a cause, it would be much easier for that cause to gain traction. But it wasn’t exactly political activism Andrew was interested in.

“I think The Point should have been a book. You know, The Point is much more of an idea. It’s so abstract. […] People need to be able to go to a website and in a second and a half understand exactly what it is.”

The decision was made to target small, local businesses — like bakeries and sports goods stores. Unlike national brands, mom-and-pop stores had a hard time taking advantage of e-commerce — or promotions in general. Most of them didn’t own a website — or any online marketing channels whatsoever.

Groupon would promote them for free, taking a cut from the sales. But nobody wanted to trust a kid with a website. Ironically, after cold calling a bunch of businesses, Andrew found Groupon’s first deal in his own building.

It was a beautiful idea — but it was better off as an idea than an actual product. The concept of The Point was so novel and grandeuse it was difficult for people to grasp it. Few people would open up their wallets for a website they didn’t trust — let alone understand.

“We got this other deal at Motel Bar, which is the bar and pizza place downstairs from our office. I think we sold 20 of those the first day that we ran it. The way that we sold them was by going to the lobby of the office building, or standing outside of Motel Bar, and handing out little postcards that we had printed.”

“It’s not very fair. I’ve been a customer for this company for five years and they’re hitting me with a $200 cancellation fee because it doesn’t fall on any one anniversary. […] There should be a way for us to all come together and say, ‘We refuse to pay this fee.’”

The thing to understand about Groupon is that it was designed for a massive buyout. Its strategy was literally to expand to as many cities as possible before the copycats would take over, and then have all of that investment ($1.4 billion in total) pay off via big exit.

What happened next was nothing short of intoxicating. Businesses stacked into a 9-month waiting list to have their daily deal run. Groupon’s email list grew to 10 million subscribers within years. They borrowed a bunch of money and hired a bunch of people.

The idea was that if you get enough people willing to buy a certain product, the business will be incentivized to give a mass discount — and share profits with the middleman.

Even though The Point was mostly a playground for weed-legalizing-trolls, some users saw a more practical application for it: strangers online would organize themselves into groups to get discounts from local businesses, like movie theatres.