Opinion
Mason: Yahoo in 2010 was a place where great companies went to die
“And my perception of Yahoo at the time was it was a place where great companies go to die.”
Insight
Mason: Proliferation of daily deal copycats destroyed Groupon's core business model
“The Proliferation of clones was undermining the foundation of the business model. The business model was based on scarcity. It was based on the novelty of one of these things existing per day in a city, and when you have 50 different Groupons in Chicago, all o…”
What-if
Mason: Groupon could have rivaled tech giants without post-rejection execution mistakes
“And it could have, maybe it could have been, were it not for some execution mistakes that happened after we made that decision.”
Assertion Not publicly verifiable
Mason: Hired actress to impersonate Yahoo CEO Carol Bartz to prank staff
“What happened was we had an all hands meeting at this church down the street from the office and, you know, they're the 500 or a thousand Groupon employees were in this church. And I came up to the stage. I said, hey, I have a special announcement... I said, h…”
Disclosure
Mason: Pursuing an IPO was part of the board agreement to reject buyouts
“That was basically part of the agreement with the board.”
Opinion
Mason: Some merchants lost money on Groupon, as occurs with advertising
“I think, like, for sure, there are businesses that lost money on Groupon. It's a little tricky because it's this new form of advertising, basically. Businesses lose money on advertising all the time.”
Disclosure
Mason: Refused voluntary resignation, forcing Groupon board to fire him
“I mentioned earlier that we didn't have the same vision on, on where to take the business, so I wasn't super into that idea. And I was like, you can do that, but you'll have to fire me.”
Opinion
Mason: Quirky persona was tolerated while Groupon was private, weaponized post-IPO
“Anyway, it was all, like, good and fun when we were a private company, and then when we became a public company, it was kind of weaponized as a sign that I was, like, not suited for the job and immature. It didn't make sense to me, because it's like, I was thi…”
Assertion Not checkable as stated
Mason: Groupon scaled merchant take rates from ~10% to 50%
“Well, we didn't take that much at first. We might have taken, if we're 10 dollars a unit, we might have taken a dollar, if anything, in those first deals. As we did it more, and we started to see the value that these businesses were getting out of it, and star…”
Insight
Mason: Founders get slack on inexperience if they demonstrate rapid growth
“When you're a founder, you just have this, you just get a free pass on a lot of stuff. I guess you bring something to the table or people just like assume that you're stuck there or something like that, and they're willing to give you some slack and understand…”
Disclosure
Mason: Groupon found Google's 2010 acquisition interest far more exciting than Yahoo's
“Google got wind and came along, and that was more exciting. There, like, Google was the... The cool company.”
Opinion
Mason: Groupon's non-subscription daily turnover alienated Wall Street
“We're not a subscription business. It's harder to understand what's going to happen, especially when, like, You're completely turning over the inventory of your website every single day with completely new stuff. So, so I think we were like difficult for wall …”
Assertion Not checkable as stated
Mason: Groupon missed quarterly projections by $10M due to French spreadsheet error
“My CFO and I were meeting with investors in Barcelona or Madrid or something like that when we got a call from our French office that there was some, like, error in the spreadsheet they were using to Track stuff, and we were gonna miss our number in, in France…”
Disclosure
Mason: Detour was self-funded to avoid investor pressure
“Yes. At this point I was like, I need a break from investors. Like, I get the role, but I just want to build something truly great without thinking about anything else other than building something truly great.”
Insight
Mason: Except for rare outliers like Bezos, founder success requires luck
“I think there's like, I don't know, maybe Jeff Bezos and a handful of people where it almost like doesn't matter what circumstance could have shown up in their life. Like they were going to end up being a super successful billionaire. For the rest of us, it's …”
Insight
Mason: Every success I've had came from the rubble of previous messes
“Everything that I've done that's been any form of success has not been the obvious thing from the start. Like, you end up finding it in the rubble of some mess that you've created.”
Assertion Supported
Mason: Lefkofsky offered $1M to drop out and build The Point
“So after I'd been in school for just under a quarter, he called me up one day, and he had heard about another idea for a website that I'd had that later became known as The Point. And I think his business instincts didn't know what to do with something like po…”
Insight
Mason: The Point failed because collective action required too many participants
“This idea is indicative of what a terrible idea the point was. . It was like this academic theory. That sounded like a good idea, but then when we actually started doing it, all of the use cases required such, they were few and far between, or they required a …”
Assertion Supported
Mason: The Point raised around $4M to $4.8M from NEA
“So after the initial a million, I think we raised 4.8 from NEA. Or four million or something like that.”
Assertion Partly supported
Mason: Groupon's first deal required 20 buyers for $10 pizza
“Ultimately, the first business that ran on Groupon was a pizza shop. We offered 20 dollars of value in pizza, cost 10 dollars, so people are saving 50%. And we had to sell 20 in order to hit the so-called tipping point and actually have the deal become real.”
Assertion Supported
Mason: Thousands of Groupon clones emerged rapidly during early growth
“The emergence of what became literally thousands of Groupon clones added intensity to it because we felt like we had to stay ahead.”
Assertion Not checkable as stated
Mason: Detour audio walking tours cost $30,000 each to produce
“It was cool, like really prestige stuff, if you can say such a thing, but each one cost us 30,000 dollars to make.”
Assertion Not checkable as stated
Mason: Early investors showed little enthusiasm for podcasting software
“As we talked to investors there just wasn't a lot of enthusiasm about it.”
Disclosure
Mason: Classmate's $400 website sale initially deterred him from computer science
“And just to show you how entrepreneurs sometimes have incredibly little vision I remember thinking, well, I guess he's cornered that market. You know, no more opportunity for people to build websites. And that was actually, like, weirdly, like, a deterrent for…”
Andrew Mason