If Mike Bloomberg was pitching a new startup, he’d concede that his latest venture—a long shot campaign for President of the United States—is a highly unconventional notion. The former mayor of New York is a late entrant in a crowded Democratic primary, a political iconoclast who rejects partisan groupthink, and a billionaire at a time of populist backlash. He’s 77 years old, and his Spanish has inspired a parody account . But cable news talkers and Twitter pundits are wrong to discount his chances in 2020. If you want a model for how Mike can win the presidency, don’t look at Washington. Look at Silicon Valley.

Mike made his fortune—all $55 billion of it—by changing the game, not following a script. When he first became mayor, people told him that he should tap political insiders, avoid third rails, keep voters in the dark, and for the love of god, don’t raise taxes. I was a policy adviser in the mayor’s office at the time, and, just months after 9/11, New York City was looking for continuity. So what did Mike do? He told the establishment to get bent.

He only hired people who were independent of local politics, putting merit before connections. The city was facing a crippling budget deficit, so he raised property taxes and closed underutilized firehouses to help balance the books—even though 9/11 had just happened and firefighters were sacrosanct. He told smokers they had to take it outside (not popular at the time) and told the New York Stock Exchange they weren’t getting any tax incentives to stay in New York. And he built an operation based on transparency. Every mayoral employee sat in the bullpen, anticipating our modern obsession with open offices. The status of every campaign promise—fulfilled or failed—was publicly reported; he created 311, a system to allow residents to get city services just by dialing three numbers; and he banned his employees from making calls using blocked numbers.

Should it have worked? No—he flouted every political norm on the books. Did it work? He was reelected by 20 points in 2005, the widest margin ever for a Republican in New York City. In 2009, I took charge of Mike’s reelection campaign, in which he made an unprecedented bid for a third term. He changed parties, running as an independent, and made history again. Mike always does things his way. And somehow, against all odds, things tend to work out.

Now that he’s running for President, can he pull it off again? Mike would concede that success requires major disruption of longstanding political norms, upon disproving that you need to compete and win in the early states like Iowa, South Carolina, Nevada, and New Hampshire, dispelling the belief that you need to start your campaign as early as possible, and disrupting entrenched interests like the DNC, hundreds of unions, and the high-octane machinery of the left. It means employing tactics that no one’s tried before—treating Super Tuesday as a national referendum rather than the conventional approach of treating each state as its own Rubik’s cube; focusing resources on the big, delegate rich states; reaching voters by using far more detailed data than any campaign ever has—and all of those ideas actually working.

Is he right? Personally, my bet is on Mike, which is one reason I’m helping out his presidential campaign. But let’s take a look at his campaign from the perspective of venture capital, which happens to be my day job. If Bloomberg 2020 were an early stage startup, here’s what I’d look at before investing:

What’s the total addressable market (TAM)?

In venture, if the company in question doesn’t have the potential to become a billion-dollar business, the opportunity usually isn’t worth pursuing. Here, the fate of the world is literally at stake: climate change, nuclear proliferation, keeping the country from splitting apart, and the health and well-being of hundreds of millions of people. The TAM doesn’t get any bigger than this.