Asheem Chandna has spent 22 years in venture capital, and he’s never lost money.
While you ponder that—a claim that on its face genuinely floored me—I’ll be precise about what that means: Since Chandna started at Greylock in 2003, he has never lost capital on an investment he’s led, always notching a gain or return, according to the firm. On some level, I was so surprised because this bumps up against Power Law conventions—that you have to lose a lot to find the runaway winners. And many of the most successful VCs I know have taken at least a few deals on the chin.
But Chandna appears to be an exception, backing some of the most pivotal startup successes in recent memory across cybersecurity and infrastructure software. He was an early check-writer for Palo Alto Networks (IPO in 2012 and now in the S&P 500), AppDynamics (acquired by Cisco for $3.7 billion), Skyhigh Networks (acquired by McAfee in 2017), Innovium (acquired by Marvell for $1.1 billion), and Rubrik (which went public just last year). His current portfolio includes cloud security mega-unicorn Wiz—valued at $12 billion—and AI-native email security force Abnormal Security, valued at $5.1 billion. Wiz is widely considered to be the fastest-growing cybersecurity company to date, Abnormal is the second, and both are generally viewed as heading towards IPOs.
When I ask Chandna about his no-lose track record, he’s sheepish, and says that his early career experiences as a product manager at Ethernet equipment pioneer SynOptics have paid dividends in his time as a VC.
"You’ve got to work with all these different constituents, and you have to make things happen through influence and not through any hierarchy or authority," Chandna said in an interview at Greylock’s San Francisco offices. "You have to have good people skills. If you’re in engineering or sales, if I can’t come to you and explain what the product does, you shouldn’t have any respect, liking, or time for me. The other piece of it is matching customers to technology, then understanding how to communicate that…So, if you showed up here as a founder, I’ve got some structured way of thinking: What problems are you guys solving? Who are you solving it for? Are there any alternatives to what you’re doing?...How can this be priced and packaged? Those are the elements and essence of a business, and are just things a product manager thinks through."
He added, with a good-natured shrug: "And luck plays a role, right?"
Luck is the sort of thing you can only set yourself up for, but never plan. Chandna—who is seed and Series A-focused—and I spent some time together, including one late afternoon in front of a whiteboard, as I asked him 100 questions. As Chandna systematically outlined how he thinks about founders, I thought about the thing that I have always believed to be true: that good process optimizes for good outcomes, come what may.
Parts of Chandna’s framework are intuitive to VC watchers like me. He’s a believer in founder-market fit, the idea that founders who deeply understand their target market and problem are poised to succeed. (This is a hot topic in VC, but Chandna’s in good company: Sequoia’s Alfred Lin told Fortune last year he believes in founder-market fit.) There are also criteria like the company’s stage appropriateness—are you actually ready for investment—the founder’s track record, and whether or not the founder has some inherent advantage in the sector they’re operating in.
What I found most unexpected was Chandna’s observational diligence. Would he want to go work for this founder, he wonders often. Chandna isn’t just looking for good communicators—he’s looking for precise communicators.
"If you email me and you’re a founder who wants a meeting, the first thing I’m going to ask you for are documents," he said. "I don’t always get it, but I probably get it 75% of the time. Then, if the document isn’t highly precise, it's highly unlikely you’re somebody we want to fund."
He’s also especially drawn to founders who are adaptable, and who improve across meetings.
"If we have three meetings over a period of two weeks, I should see that you’re getting better," Chandna told Fortune. "It's about the pace of learning. If after three meetings, there’s really no advancement, how can I know you’re a learner?"
I turned the kaleidoscope and asked Evan Reiser, CEO and cofounder at Abnormal, what it’s been like working with Chandna since 2018, when they began incubating the startup at Greylock. He tells me Chandna is as warm and agreeable as he seems, but he’ll also pipe up very quickly about problems.
"If he believes something is messed up in the business, he will tell you," Reiser told Fortune. "There have been some times where, frankly, I was like: 'Asheem, man, does this really matter right now?' We’ll just go do it because Asheem said it was important. Then, in hindsight, we’ll say: 'Wow, good thing we did that.' A year in, our gross margin was 0%, right? I told him: 'This doesn’t matter, we’re going to optimize over time.' And Asheem said: 'Do you know how many times I’ve heard that?'”
Talking to Reiser, it occurs to me that Chandna is someone directly engaged with uncertainty, not just risk. He looks to structured ways of thinking as guidelines, not gospel. Chandna’s frameworks are his way of ensuring he takes nothing for granted.
"Part of Asheem’s superpower is that he has a really high bar," said Reiser. "He’s fairly conservative about taking on risk, and he’s super open and willing to challenge you. I think if you talk to anyone that's been on a board with him, they'll say: 'Yeah, Asheem’s going to say the things no one else will.'"
When VCs chase deals, they’re hoping they’ll be lucky. But Chandna’s process is a reminder that so much of investing isn’t luck—that an ability to confront uncertainty is vital, and problems rarely solve themselves alone.
Because lasting luck is only possible with thoughtful process.
See you Monday,
Allie Garfinkle
X: @agarfinks
Email: alexandra.garfinkle@fortune.com
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