How a spur-of-the-moment trip made GV the lead investor in Cribl’s summer Series E

Michael McBride was the new guy at Google Ventures, but that didn’t stop him from chasing a deal across the world.

It was less than six months after McBride, previously the CRO of GitLab, had joined GV as a general partner. He (like many other investors) was pursuing IT and security data startup Cribl. Despite the competition, McBride believed that the hype around the company was justified and that he was uniquely qualified to be helpful.

Cribl CEO and cofounder Clint Sharp told McBride that, theoretically, he could meet him and the Cribl team in Portugal, where the startup was holding an event for customers and employees.

"I was like: ‘No problem, I'll come to Portugal,’" said McBride, who got on an 11-hour flight to Lisbon.

It was the sort of thing Sharp didn’t believe actually happens.

"Even in the realm of investor stories, I thought that was a pretty zany one," said Sharp. "I heard that people do this sort of stuff all the time to win deals, but it never happened to me."

The two walked around the resort town Sintra for hours, tooling around pastel castles that served as summer homes to Portuguese princes of the 1800s. As tourists, getting to know each other and their surroundings, Sharp and McBride connected.

"He had, from the outside-in, done all of this research on us," said Sharp. "He’d talked to our customers…and he was very, very excited about us. I think it was because in a lot of ways we pattern match with what GitLab has done, right? We’re a quickly growing enterprise software company. It's something that he can really easily wrap his head around, because it's squarely in his wheelhouse."

Sharp was (and is) charmingly amused by the idea of being the belle of any fundraising ball: "The people that we sell to are the IT and security people, the sort of grizzly-haired admins in the basement. The people that keep all the lights on and the doors open—I was one of those people."

But nevertheless, the encounter kicked off Cribl’s oversubscribed $319 million Series E, raised at a $3.5 billion valuation and announced in August. McBride and GV led the round, marking the firm’s second-largest investment ever, surpassed only by the firm’s 2013 investment in Uber.

"I have not lost a wink of sleep since we did the investment, because I'm so confident in that team," said McBride.

GV, as it has done many times before, "pressed the believe button"—a GV-specific phrase that CEO and managing partner David Krane taught me.

Cribl’s is one of many stories I heard when I spent two days with GV, as the firm commemorated its 15th anniversary. Read the whole story here, for Fortune’s exclusive look inside GV.

ICYMI…Rebelstork, a Toronto-based discount online retailer of overstock and returned baby gear, raised $18 million in Series A funding. Maveron led the round and was joined by Serena Williams’ Serena Ventures, Jay-Z’s Marcy Venture Partners, and existing investor Golden Ventures. Read the story by Fortune’s Jason Del Rey here.

See you tomorrow,

Allie Garfinkle
Twitter: @agarfinks
Email: alexandra.garfinkle@fortune.com
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Nina Ajemian curated the deals section of today’s newsletter.

This story was originally featured on Fortune.com