Back in his days running Groupon, Andrew Mason had a reputation for unseriousness, one he cultivated with weird jokes like bringing a pony to the office and making a video of himself doing yoga in his underwear. When I recently interviewed Mason in San Francisco, however, he was far from the adolescent class clown I was expecting. In conversation, he came across as an unusually reflective and forthright person, who in the years since he last peddled daily deals, has spent a lot of time thinking about technology's impact on humans. You can see proof of that in the novel ownership structure of his newish startup,  Detour

Rather than parcel out shares in Detour according to a conventional startup equity structure, Mason essentially invented a new one. He calls it Progressive Equity, as in progressive taxation. In a progressive equity structure, once the value of a founder's shares pass a certain pre-set threshold, they get "taxed" at 50 percent, with the taxes getting redistributed to other employees.  The idea, as Mason put it in a blog post, is to "maximize the number of employees that achieve financial independence" in the event of a big IPO or other liquidity event, "and minimize the number of newly-minted dynasties." 

The desire to share the wealth more equitably was born out of Mason's experience at Groupon, from which he walked away with a reported $260 million. (At one point, before their value collapsed, his shares were worth $1.5 billion.) Mason left feeling like he had a lot more money than he had any use for, while others who had worked just as hard for Groupon's success for nearly as long received only modest bonuses. Looking around Silicon Valley, he saw the same situation playing out all over. "The scale gets so large that you end up with founders making more money than they can spend in a million lifetimes," he says. "Once you get to above a certain threshold it seems weird you would just continue to pile money onto these founders instead of finding ways to distribute it more equally." 

He believes the standard equity model, in which founders (and venture capitalists) earn mega-riches while everyone else ends up with crumbs, is a holdover from an era when starting a technology company was considerably more expensive and difficult. Without outsized incentives, no one would have done it. Since then, however, "the risk involved in being a founder has changed as the founder ecosystem and the tech entrepreneur ecosystem has evolved in a way that now there are tools that make it drastically easier to create a startup," he says. (Inc.'s April 2016 issue focuses on how companies like Indiegogo and Stripe have made it easier than ever to launch a startup.) 

"Plus on top of that, if you're a Google engineer, if you're coming out of Stanford CS [computer science], there's not that much risk in doing a startup," he adds. "It's a nice feather in the cap of your resume even if it fails. There's not that much opportunity cost. You can always go back and get that job at Google."

Mason open-sourced the paperwork he used to enact Progressive Equity at Detour in hopes that other entrepreneurs will follow his lead. So far, he says, he's had "a bunch of phone conversations" with interested parties but as far as he knows, no other startups have committed to the model. "The trouble is legally getting it set up. I posted the legal documents but everyone has their own lawyer and has to go through the process," he says. "It's sufficiently non-turnkey that I'm not sure people have gone through with implementing it."

Surprisingly, he's just fine with that. While he regards Progressive Equity as a worthwhile experiment, he's not at all certain that flattening out the distribution of startup payouts would be the best thing for society. "The thing I wonder about it is, okay, we're just redistributing wealth from the ultra-rich to the megarich," he says. "We're not doing anything to change the real problem, which is the disparity between people lucky enough to work in our industry and the rest of the world. One could make the argument that it would actually be better concentrating all that wealth in one or two founders who then do what Zuckerberg just did and give 99 percent of it away instead of just creating 100 early employees of a company who are all making $50 million they can all spend on artisanal whatever."

Published on: Apr 7, 2016