Navigating the Ironic Journey of CEOhood

When Andrew Mason started Groupon 10 years ago he was in his mid-20s, fresh out of grad school, and running a company for the first time ever. Within 2 years Groupon was called the fastest growing company in history. 

And then just as rapidly and just as dramatically, its fortunes changed. This dream rise, the nightmare fall, all in this incredibly short time-span, it’s like a startup fable. But it actually happened. To a real guy!

In part one of this two-part conversation, Andrew talks with Alex about Groupon’s rise. How it started as a website designed for something completely different, what it felt like when it finally caught on and started to grow, and Andrew’s own conflicted feelings about being a CEO. 

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