Andrew Mason is still worth hundreds of millions of dollars. Sure, he was fired from his job, but I wouldn't exactly call that a "fall". It's not like they took away his equity in the company.
https://www.forbes.com/sites/joanlappin/2013/03/05/dont-cry-...
The entire Groupon story is a black stain on Chicago startup history.
For execs? I'd assume frequently.
I think we tend to equate failure with not living up to our expectations, no matter how unrealistic they were. Andrew is probably comparing his actual outcome with the potential outcome that was envisioned when Groupon was flying high. He’s not in the three comma club like he expected, or like his (former) peers are. Hence, “failure”.
You could argue that anyone reading this right now on a computer is probably anthropologically successful enough that “failure” is never a fair term to apply to them.
First, it was a fail if felt your primary responsibility is to the team, shareholders and just general commitment you often set out to as a founder fulfill in building something that people love and use.
Being fired from something you believe you tried your hardest at doing right is brutally painful to self-identity. The quality of the food you eat after word at best distracts you from some of the pain and nagging "what-ifs."
https://amp.businessinsider.com/steve-case-lesson-aol-time-w...
https://www.nytimes.com/2006/08/18/business/media/aol-adds-a...?
I wouldn't trust myself running a big company!