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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VENTURE DEALS

- Berry Street, a New York City-based dietary counseling platform, raised $50 million in funding from Northzone, Sofina, FJ Labs, and angel investors.

- Urban Sky, a Denver-based stratospheric balloons developer, raised $30 million in Series B funding. Altos Ventures led the round and was joined by New Legacy Ventures, Lerer Hippeau, Catapult Ventures.

- Lynx, a Boston-based healthcare payments platform, raised $27 million in Series A funding. Flare Capital Partners led the round and was joined by CVS Health Ventures, McKesson Ventures, and existing investors .406 Ventures, Obvious Ventures, and Frist Cressey Ventures.

- TrueFoundry, a San Francisco-based AI deployment and scalability solutions platform, raised $19 million in Series A funding. Intel Capital led the round and was joined by Jump Capital, existing investors Eniac Ventures and Peak XV’s Surge, and angel investors.

- Cognida.ai, a Lincolnshire, Ill.-based AI adoption solutions provider for enterprises, raised $15 million in Series A funding from Nexus Venture Partners.

- Presto, an Oakland-based electric vehicle charging platform, raised $15 million in seed funding from Union Square Ventures, Congruent Ventures, Powerhouse Ventures, and Jetstream.

- Tyba, a San Francisco-based energy storage optimization solutions provider, raised $13.9 million in Series A funding. Energize Capital led the round and was joined by Pear VC, Mobilize Climate Capital, Borusan Ventures, and existing investors Powerhouse, Wireframe, Virta, and Lorimer.

- Model ML, a New York City-based AI-automated financial research and due diligence platform, raised $12 million in funding. Y Combinator and LocalGlobe led the round and were joined by angel investors.

- Miist Therapeutics, an Alameda, Calif.-based inhaled therapies developer for smoking addiction and migraines, raised $7 million in seed funding from Refactor Capital, 1517 Fund, Freeflow Ventures, and others.

- &AI, a San Francisco-based AI agent developer for patent attorneys, raised $6.5 million in seed funding. First Round led the round and was joined by Y Combinator, SV Angel, BoxGroup, and angel investors.

- TaxGPT, a San Francisco-based AI-powered accounting co-pilot, raised $4.6 million in seed funding from Rebel Fund, Mangusta Capital, Y Combinator, angel investors, and others.

- Trace.Space, a Riga, Latvia-based AI-powered industrial and automotive product development requirements management platform, raised $4 million in seed funding. Cherry Ventures led the round and was joined by Outlast Fund and existing investors Nebular, Fiedler Capital, and Change Ventures.

PRIVATE EQUITY

- Family Resource Home Care, a portfolio company of Great Point Partners, acquired Beneficial In-Home Care, a Spokane, Wash.-based home care provider. Financial terms were not disclosed.

- Workwell Group, backed by Universal Partners, acquired the workforce management and workforce technology divisions of Eastridge, a San Diego-based staffing provider. Financial terms were not disclosed.

EXITS

- Rubicon Founders acquired a majority stake in Horizon Infusions, a Blue Ash, Ohio-based infusion centers network, from BroadOak Capital for around $130 million, per Axios.

- Warner Music Group acquired a majority stake in Tempo Music Investments, a New York City-based music rights investment platform, from Providence Equity Partners, which will maintain a minority stake. Financial terms were not disclosed.

OTHER

- Parler Cloud Technologies acquired Triton DataCenter, a Monroe, Mich.-based open-source cloud management platform. Financial terms were not disclosed.

- Phenom acquired EDGE, a Bangladesh, India-based resource management and talent mobility solutions provider. Financial terms were not disclosed.

- Rhino, a New York City-based security deposit insurance platform, merged with Jetty, a New York City-based security deposit insurance platform. Financial terms were not disclosed.

IPOS

- Karman Holdings, a Huntington Beach, Calif.-based defense and space systems developer, plans to raise $422 million in an offering of 21.1 million shares (60% secondary) priced between $18 and $20 on the NYSE. The company posted $331 million in revenue for the year ending Sept. 30, 2024. Trive Capital and Norman Carl Christensen back the company.

- Aardvark Therapeutics, a San Diego-based metabolic diseases therapies developer, plans to raise $106.2 million in an offering of 5.9 million shares priced between $16 and $18 on the Nasdaq. Decheng Capital and Vickers Venture Partners, and Jane Wu Lee back the company.

FUNDS + FUNDS OF FUNDS

- CF Private Equity, a Wilton, Conn.-based private equity firm and affiliate of Commonfund, raised $539 million for its 15th fund and $100 million for its second direct fund focused on venture capital.

- o15 Capital Partners, an Atlanta-based investment firm, raised approximately $370 million for its first fund focused on undercapitalized companies in the healthcare, business services, and education sectors.

PEOPLE

- PeakEquity Partners, a Philadelphia-based private equity firm, promoted Noah Ehrich to principal.