Wesley Chan is often seen in his signature buffalo hat; however, he may be even more well-known for his ability to spot unicorns.

Over the course of his career in venture capital, he’s invested in over 20 unicorns, including AngelList, Dialpad, Ring, Rocket Lawyer and Sourcegraph. Five of those went on to become decacorns: Canva, Flexport, Guild Education, Plaid and Robinhood. Chan’s was the first check into most of those.

After working at Google in its early days as an engineer, he became an investor. His venture capital pedigree started at Google Ventures and continued to Felicis Ventures. Now as the co-founder and managing partner of FPV Ventures, he leads the two-year-old firm’s $450 million venture capital fund with co-founder Pegah Ebrahimi. 

And while all of this success has been well-documented over the years, his personal journey … not so much. Chan spoke to TechCrunch about the ways his life impacts how he invests in startups.

His story started before he was born, when his family migrated to the U.S. from Hong Kong in the 1970s.

“They came here with no money, and in fact, growing up they didn’t have any money,” Chan said. “It’s just really fascinating to watch that journey. That they would leave a place where they didn’t speak a word of English and — they still don’t speak English very well — and build a new life because they felt that that was what was necessary.”

Chan admits that he wasn’t as appreciative of his parents’ fortitude when he was young. However, growing up in a hard-working, immigrant family that didn’t have much money ended up teaching him how to recognize nuances and be someone who can adapt.

“I’m in a business now where people judge you very quickly,” Chan said. “Among my LPs, a lot of them don’t have the background I do. I have to pick up all these tunes of things that they were trained on and be a bit of a chameleon. Then I have to signal to them that they can trust me.”

How he got into MIT even with bad grades 

Chan’s parents split up when he was a kid, and he was raised in a single-parent household by his mother. He worked three jobs in high school to help support his family, including as a parking lot attendant, a waiter and a dishwasher in a biology lab at the California Institute of Technology.

He landed the dishwashing job from an ad on Craigslist and remembers taking the No. 22 bus from his working-class Southern California town on a 42-minute ride to CalTech, where he would go and wash beakers.

One day, the lab manager, famed gene biologist Ellen Rothenberg, asked him if he would read a college-level book on biology and laboratory techniques. Not wanting to lose the job, he did it.

“I had barely taken high school biology,” Chan said. “I went to a high school that wasn’t great. It was like by hook or by crook that I wound up making my way through school. Other kids were doing after-school sports or going to PSAT prep classes. Not only did I not have that, I was having to make money for my family.”

Turns out, regardless of the high school experience, Rothenberg saw something in Chan. When one of the PhD students left, Chan was promoted to the lab bench. And for the next three years, as he went through high school, Chan was also doing research.

This was in the early 1990s, during the nascent days of stem cell research. Rothenberg’s team taught the teenaged Chan how to do research and he was later part of a group that discovered a protocol for changing stem cells into red blood cells. He also helped when the team published an academic paper on the protocol.

Then one day Rothenberg, who had gone to both Harvard and MIT, asked if Chan had thought about college.

“I’m like, oh man, I have to finish this job and make money for the parents, and she’s telling me I should go to school,” he said. “Little did I know that she called the admissions offices. When you’re like a poor immigrant student, you don’t understand all these things.”

Harvard ignored her, but MIT didn’t. And that’s how people get into school with terrible grades, Chan said. 

“Somebody took a chance on me,” he said. “So many people stumble through life, and I don’t think I would have had the opportunities that I did today if it wasn’t for someone who said, ‘He works hard. He wants to do research.’”

Business lessons from being lonely

That’s how Chan said he looks at venture capital, too. He doesn’t look for the person who was a member of the right country club. Instead, he looks for people who have grit and understand what it means to work hard.

“One of the lessons I learned, growing up that way, was that you have everything to gain and nothing to lose,” Chan said. “It’s hard work, plus a lot of luck. Plus, understanding that there’s people helping you ultimately open the door to anything.”

He credits that help from Rothenberg for everything that came after.

“If it wasn’t for MIT, I wouldn’t have found Google. If it wasn’t for Google, I wouldn’t have found Google Ventures. If it wasn’t for Google Ventures, I wouldn’t have found my team at Felicis,” he added. “And if it wasn’t for Felicis, I wouldn’t have had Canva and all these amazing companies, many of them run by immigrants or people that have lots of grit, who grew up in very non-traditional backgrounds like myself.”

To attend MIT, he had to leave everything he knew at home and move to the opposite coast. Once there, Chan also worked multiple jobs to pay his way through MIT, where he got his bachelor’s degree in computer science and later graduated with a Master’s of Engineering. 

What was it like to leave his family? In a word, hard. Due to having to support himself, Chan wasn’t able to take as many classes as he wanted to or be like his friends who would go on fun trips on breaks.

However, he looks back on that experience as another thing that set him up for life as a venture capitalist.

“When I led the Series A in Canva, which will ultimately return 40x plus for that fund, 111 people said no, which made it very lonely to do that deal,” Chan said. “When you’re the guy that can’t go to prom because you have to work, or you can’t go on the ski trip or to the graduation party, that’s what I’m dealing with.”

Being left out like that taught him: “Who cares if the rest of the world is laughing at us; you get this amazing amount of grit and the ability to like being lonely and be okay being lonely.” 

After graduation, Chan went back to California and got a job at HP Labs. Then the dot-com crash happened, and that job fizzled out. But all was not lost. There was one company hiring despite the disastrous environment. And they happened to like people from MIT. 

Spoiler, it was Google. Now, working for Google is not like the movie “The Internship” where Vince Vaughn and Owen Wilson lie their way into an internship and spend time competing with other teams on various projects. It was better … for those who liked dogs.

“Dogs were running around and would run into you and knock you over,” Chan said. “It wasn’t like that movie. You have to get to work.”

He was put on a project developing the ad system, “which was the most necessary at the time, so I got very lucky.”

Building something that founders want

This kicked off a 15-year Google career that included seven years building products and five years as chief of staff to Sergey Brin, who co-founded Google with Larry Page. Chan worked on projects, including the Google toolbar, which became Google Chrome. 

“When you’re one of the few companies that made it, it was great,” Chan said. “Larry and Sergey were very kind, always saying, ‘Hey, maybe Wesley brought us something and we should let him experiment this out.’ That would eventually become Google Analytics or Google Ventures.”

He was even one of the people who interviewed Sundar Pichai when he was up for a job at Google. Obviously, Pichai later became CEO of Alphabet and Google. 

In 2009, Chan told Google that he wanted to do a startup. He had joined the company when it was less than 100 people and stayed until it was over 35,000. He recalls them joking that when you go to a startup, you are the one buying the toilet paper. Chan’s reply was that he didn’t mind buying the toilet paper. Instead, they suggested he go help Bill Maris build Google Ventures.

“They told me to go build a product that founders want, rather than be a founder whose product that a company wants. And we did it,” Chan said. “Google Ventures is still a real firm today that people want to take money from.”

Beyond overcoming obstacles to get where he is today, Chan continues to face some odds, especially as a gay Asian man in tech. When he first started in venture capital, senior white men were running the firms, sharing deal flow on the soccer fields or during an African safari, he said.

When you’re someone looking to build your deal flow network but your background doesn’t fit the country club mold, it’s difficult, he said. And there is not much of a support group in venture capital for the LGBTQ+ community.

“That’s the challenge of being an outsider in this business,” Chan said. “You have to fight your way up or find different ways of working with founders so it doesn’t look like you’re being lazy or not making any progress. If you look at venture capital and the number of successful partners in the LGBTQ+, you can count on two hands. There aren’t many of them, and there’s probably 6,000 venture capitalists. Why is there such low representation? And the number of openly out ones like us is even lower.”

That’s why he and Pegah Ebrahimi started FPV Ventures two years ago — to provide the style of investing based on their unconventional backgrounds. (Ebrahimi cut her teeth as the youngest CIO at Morgan Stanley before doing a bunch of C-suite roles at various tech companies. She actually worked on Google’s IPO.)

And the managing partners are doing so with the support of charities and foundations. A lot of the founders the firm works with “care deeply that they’re making money for good people,” Chan said.

“Our founders happen to be underrepresented minorities or women, and the really fascinating theme that I keep hearing is that they feel people misunderstand them,” Chan said. “We find founders who have the drive to succeed and have this amazing combination of humility and success. They also make sure that all their people are taken care of.”