Had Groupon Founder Andrew Mason had decades of stellar entrepreneurial experience behind him when things at Groupon started going south, he might have been able to swoop in and save the company. (Instead in 2013, Mason, then 32, was fired from his CEO role as Groupon's stock price continued to slide.)
Then again, had Mason had the benefit of experience he's since accrued, he probably never would have started Groupon to begin with.
"It's hard to create this really perfect narrative because, actually, what I've found is that the wisdom that I have now would have prevented me from getting into the situation that led to Groupon's existence in the first place," Mason said.
He spoke Tuesday at Launch Festival 2015 in San Francisco. The three-day annual event had more than 11,000 registrants.
Now, as he works on his latest venture, called Detour, an iPhone app that provides location-based audio tours, Mason readily acknowledges that there's no such thing as perfect. But this is something he's only relatively recently accepted after sitting down with Ira Glass, executive producer of the This American Life radio show and podcast.
While Mason was in the researching phase for Detour, which launched last month, he met with Glass to learn more about audio content creation.
"Most of my questions were kind of getting at how we set up the conveyor belt for consistently putting out great stories at a high efficiency rate," Mason said.
"I asked a lot of questions that were getting at that idea, but eventually he was like: there is no conveyor belt. It's always messy. Every single story we do, every single pitch that we get -- it's a messy process," Mason recalled Glass explaining.
Ever since, Mason said he's been able to look back at the good and bad decisions he's made throughout his career in a new light. For instance, before Groupon became a deal website, it was a collective action platform -- similar to Kickstarter, but much less focused. Mason knew it wasn't going to work, and he was under pressure to pivot.
"It took making that bad decision and getting myself into a mess in order to be put in the situation where I had to figure out how to work with what I had and make something out of it," he said.
Today, Mason's OK with the idea of a flawed performance.
"If you're not getting yourself in a mess, then you're not really in the state where true innovation and breakthrough ideas can happen," he concluded.