2. GET INSIDE THE RIGHT PEOPLE’S HEADS (NOT JUST THE EXPERTS')

Jules Maltz gives away hundreds of millions of dollars for a living. The 36-year-old partner at Institutional Venture Partners has helped make bets on some of the hottest tech companies of the past decade, including Twitter, Snapchat, Slack, and Dropbox.

But writing big checks isn’t as easy as it sounds. If he takes too long, a hot startup will find other investors. If he rushes in, he risks getting caught in a bad deal. "I see all sorts of companies in different industries," Maltz tells me. "If I don’t make the right call quickly, I risk missing out on the next big deal."

When the pressure is on, how does he decide which companies to back and which to let go? Maltz’s secret isn’t just talking to smart people. It’s "talking to the rightpeople."

When Maltz led his firm’s investment in Oportun, a financial services company primarily serving Hispanic communities, he had to figure out what mattered most in retail banking—not his professional forte. "I picked up the phone," Maltz says. "We talk to 10 to 20 people before we make any investment."

The most valuable insights often come from people who are are closest to a product, policy, or service but outside your sphere.That's more than just a venture capitalist doing his due diligence—it's a way of efficiently circumventing a lot of bad (or just superficial) information and getting straight to the heart of the matter. Maltz believes there’s never a shortage of Googleable experts and industry analysts willing to share their knowledge. Once you find a few, Maltz recommends "letting people ramble a bit" before asking the most important question of all: "The best thing you can ask is, ‘What questions should I be asking?’"

When Maltz posed that question about Oportun, he learned that, above all else, success in retail banking hinged largely on customer enthusiasm. And, as smart as the industry analysts might be, there was no way they could tell him how much Oportun’s customers loved the bank; it was time for Maltz to get outside his office and inside customers’ heads.

"I had to learn about a customer who wasn’t me," the red-headed, half-Jewish, native Oregonian told me. Maltz stalked retail locations to find customers willing to talk about their experience. Call it old-school market research if you like, but it was also the most efficient and reliable way for Maltz to brush up. Only by collecting insights straight from customers’ mouths could he understand if the bank was a company people would stick with over the long term.

Guided by questions from industry experts, the insights Maltz collected helped him make the case for a $47 million investment. However, without the firsthand information Maltz heard from Oportun’s customers, the deal would never have happened.