Groupon's Andrew Mason: The Rise & Fall

Part 1 

  • The whole experience (running Groupon) seems like a fever dream that happened to someone else. (8:16) 

  • The origin story of Groupon: I was in grad school when I got a call from someone I used to work for. He said: Hey why don’t you drop out of school and I’ll give you a million bucks to come and start this thing. (9:01) 

  • The original idea was a website called The Point. Which was a way to say I’ll do something - but only if a critical mass of other people does it with me. (10:25) 

  • I had this vision of building a platform for solving the world’s collective action problems. An abstract model that would handle every kind of campaign for organizing people that one could imagine. . .Because it was so abstract no one knew what to do with it. (13:16) 

  • The pivot to Groupon: People would start campaigns to get 10 people together to buy something but only to get a discount. . .This felt like the dumbest and least inspiring application of the model compared to what we imagined it being used for. Out of desperation, we decided to try this group buying idea. We went out and found one deal a day and then emailed it out to a list of people who may be interested in it. (13:56) 

  • The opportunity for Groupon clones: We had a backlog, 9 months deep, of people who wanted to be featured. We ran one deal a day so we couldn’t serve all that demand. (24:47) 

  • How Andrew dealt with the stress of going from grad student to CEO of a fast-growing company: I was reading bullshit business books to try and figure out what was happening to me. (30:11) 

  • On the ride up there is a lot of stuff in the press to deify or make the founder seem like a hero or genius. (32:29) 

Part 2 

  • At the end of year two of Groupon: thousands of employees, hundreds of millions in monthly revenue. (1:51) 

  • I asked a financial advisor how much money I need to not worry about money anymore. So I could make decisions about the company without having to consider how this decision would affect my personal wealth. His answer: $15 million. (4:08) 

  • Why not sell to Yahoo: I looked at their other acquisitions and it was this graveyard for cool companies. That’s what we were afraid of. (5:30) 

  • The process of growing a company is a process of having principles methodically beaten out of you. (7:03) 

  • When we went public I just remember being bitter and mad (after constant criticism). The overall tenor had turned from an intense but wonderful ride to this embattled, highly stressful fight. (17:49) 

  • Being public was a huge distraction. The advice you get from people who have taken companies public is just ignore the stock price. You can ignore the stock price, but your employees won’t. It’s not something you can just ignore. The result was that 50% of my time was spent doing things that had nothing to do with building a great company and everything to do with managing the fallout from going public. We weren’t ready for it. (19:47) 

  • Biggest regret: the moments when I let a lack of data override my intuition on what is best for customers....There are certain things you have to be religious about in a company: sorry I’m not going to look at the data on that. This is what we are going to do because we know that is right. (30:32)