With nearly half a billion users, Gmail is the world's largest email service and considered an essential for many of us. This is the story about how Gmail almost never was.
In the early 2000s, Paul Buchheit took a naive approach to a big problem that previous, more experienced developers has tried to tackle—an effective web-based email platform. Trying to find operational software, Buchheit—Google employee No. 23—turned to an option that everyone else had written off.
Previous failures meant nothing to Buchheit, who pressed on and tried it anyway. He found the solution in the unlikely area of a browser capacity.
In his case, however, it wasn't extensive knowledge of browsers that helped him—in fact, it was the opposite. His naiveté saved him.
"Very often, if you do something new, the actual feedback people will say is, 'This is what we tried before and it doesn't and won't work,'" he says. "If you're naive, you may not even realize that it's been tried and didn't work," he says. "We tend to overlearn from the past. Just because something didn't work in the past, doesn't mean that it can't work in the future—especially in technology where things are constantly changing. Maybe the technology changed, the world has changed, or you're just simply taking a different approach. All these people [at Google] were telling me that it was a bad idea and it would fail," he says. "But I didn't really care, I thought they were all wrong and tried it anyway—and it worked."
Buchheit went on to prototype Google AdSense and FriendFeed—Facebook's largest acquisition at the time—and is now an investor and Y Combinator partner. But he says he's more naive today than ever. "If anything, I'd be more willing to do crazy things now," he says. "I'm told that I'm naive on a regular basis."
He says it's less about age and more about the environment. "If you spent too much time in the wrong environment—if you spend a lot of time in a very cautious environment—you begin to adapt to that environment," he says. "There's a difference between someone who has spent 20 years at IBM versus someone who has spent 20 years working at various startups."
But being naive has got the best of him such as a time when he failed to invest early in Dropbox when he had the chance. "It's the biggest mistake of my career," he says. "I didn't move fast enough and I work in the business where speed is really important. You can't spend a lot of time thinking it over because someone else will come and get it."
When looking at startups to invest in, Buchheit says he doesn't mind if entrepreneurs are young or naive as long as they keep the focus in the right place.
Hey says that too often companies get distracted by the startup scene or a lefty buyout. "At Y Combinator, we tell people that they should essentially be spending all of their time either talking to customers or working on the product, not at conferences or other things," he says. "The great entrepreneurs are focused on building a product that people will love and building a business."
He's always looking to invest in entrepreneurs with the same focused stupidity that Mark Zuckerberg had in Facebook's early days. "I think any reasonable person would have said, they should have sold to Yahoo for a billion dollars because it wasn't that big—just a college network—it had just a few million users, and they weren't worth that much money," he says. "But fortunately Facebook was not run by just anyone—it was run by Zuck, who had the internal conviction to turn down the billion-dollar offer and then actually grow it into a 170 billion-dollar company."