Josh Elman wants to fall in love. He wants to make this investment. But the startup founder sitting across from him—bland and too confident for his own good—is making it difficult. The founder is not so much playing hard to get as clueless.

Elman is a partner at one of the tech world’s top venture capital firms, Greylock Partners. These days Greylock maintains not one but two offices in the San Francisco Bay Area. One is on Sand Hill Road, in Menlo Park, long the Wall Street of venture capital and more or less in the middle of Silicon Valley. But these days the center of gravity in the tech world has shifted north to San Francisco, and Greylock, like most of the area’s leading venture firms, now leases space in the city.

Elman is working out of Greylock’s San Francisco offices on a sunny Wednesday in the fall of 2017. It’s there, in a factory-chic office in a part of town thick with startups and rival venture firms, that I join him for a lineup of meetings that starts with this less-than-inspiring founder of a mobile-app company that’s been around for several years. “This is someone I’ve known a long time,” Elman tells me. “From before I was a VC.”

From Becoming a Venture Capitalist by Gary Rivlin. COPYRIGHT © 2019 by Simon & Schuster, Inc. REPRINTED BY PERMISSION OF SIMON & SCHUSTER, INC. Simon & Schuster

The ground rules of this fly-on-the-wall session dictate that I can’t name the entrepreneur or his startup. But there’s no stopping me from describing the man as an odd duck. I’ve sat in on my share of pitch meetings over the years. I’ve witnessed awkward mumblers who can’t make eye contact. In the late 1990s, at the peak of the dot-com madness, I tried not to visibly roll my eyes over the hubris of the MBAs descending on Silicon Valley with their charts and projections but not much else beyond a smooth, practiced delivery and the promise of “ubiquity” for whatever they were selling.

But never had I come across an entrepreneur as buttoned-down-boring as this one. His background looked good on paper and included a stint on Wall Street. He was older than the typical founder. Yet he didn’t seem to have the personality to lead a growing tech startup.

Gary Rivlin (@grivlin) is a longtime WIRED contributor, a former New York Times reporter, and the author of seven books including Katrina: After the Flood

The founder, who also doubles as company CEO, claims that he isn’t at Greylock looking for money. “We’re not in fund-raising mode,” he says to me as we’re introducing ourselves to one another. As he tells it, he’s just an old colleague asking another for friendly advice as he preps himself to raise a large slug of money. This will shortly turn out to be bunk.

The founder takes a seat across a conference table from Elman and plugs in his laptop loaded with a multi-slide presentation aimed at convincing financiers to invest at least $50 million. To his right sits a top executive from his company: a wiry man with a shaved head, a deep r´´ésumé, and an intensity that suggests he would crash through a wall if that’s what it took to win. “We literally were making changes in the car a few minutes ago,” the founder tells Elman. He’s aiming for nonchalance, but it comes off as an obvious ploy to lower the stakes on a high-stakes meeting. He has no doubt been sweating this moment—and every slide—for weeks.

It might be overstating things some to say that pitching Greylock (as a Newsweek contributor wrote in 2014) “is a bit like being a rookie pitcher stepping onto the mound at Yankee Stadium—with Babe Ruth walking up to the plate.” But there was no doubting the firm’s supremacy. Greylock had been an early investor in both LinkedIn and Facebook, when $27.5 million bought nearly 6 percent of a company today worth more than $500 billion. (In other words if Greylock and its limited partners—those putting up the money that Elman and his partners invest—had never sold a share, that $27.5 million would be worth $30 billion today.)