Venture Capitalist Darian Shirazi ‘05 Talks Entrepreneurship, Kiteboarding, and Fatherhood

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This is the twenty-fifth article in Bears Doing Big Things, a weekly column celebrating the stories of notable M-A alumni. Read last week’s article here.

In the spring of 2005, eighteen-year-old Darian Shirazi was on the lookout for a local summer internship. At the same time, a new startup in Palo Alto with fewer than ten employees was seeking interns who knew how to code.

That young startup was Facebook. Shirazi joined as the company’s first intern, reporting directly to Mark Zuckerberg. He went on to start his own company, made the Forbes 30 Under 30 list in 2013, and currently works as a venture capitalist leading Gradient, Google’s AI-focused venture fund.

Looking back on high school, Shirazi remembered, “One of the things I loved about M-A was that my teachers really cared about me, and I thank them for that.”

“Mr. Florio, my history teacher, was a great guy,” he said. “I miss him a lot. He was very funny, and always super well-dressed when he came into class—he was very professional.”

Read: M-A Community Celebrates the Life of John Florio

For their senior prank, Shirazi and his classmates inflated hundreds of balloons, filled history teacher John Florio’s classroom with hundreds of balloons and then hid the door with a wall of stucco. Shirazi recalled, “Mr. Florio was like, ‘Where’s my classroom?’ He couldn’t find it because the wall was completely smoothed over. He eventually realized, broke it down, and opened the door. He took out a pencil and poked the balloons one by one, popping a path for himself. It was hilarious.”

Shirazi enjoyed taking calculus with Gregg Whitnah, English with Liane Strub, and biology with Patrick Roisen. He remembered, “Mr. Roisen was a tough teacher, and also quite a character. For our final project, Mr. Roisen challenged us to conduct a deep biological study. I convinced a local orthopedic center to let us borrow an expensive, state-of-the-art bone density measurement device. We were able to determine that Coca Cola consumption was significantly correlated with bone density amongst the students we tested it with. Mr. Roisen appeared—for the first time—impressed with me.”

Shirazi was also on M-A’s debate team. He remembered, “Debate was very intense. It was basically a sport without the school funding or facilities. I would say I learned just as much from speech and debate as I did from any other class. We had two upperclassmen on the team—John McKay ‘04 and Thomas Brugato ‘04—who were incredibly good and went to the Tournament of Champions multiple times. Most of my public speaking abilities and confidence on stage is a result of my time on M-A debate.”

After graduating from M-A, Shirazi worked at Facebook, and then went to UC Berkeley. He spent about 18 months studying there before dropping out to start his own company.

“In high school, I worked harder than I have ever worked,” he said. “I did everything I could to have a perfect resumé for my college applications. I took eleven AP tests, and I spent any spare time on debate. I think I was really burned out by the time I got to Berkeley, and college unfortunately felt like just more of the same. I thought to myself, ‘Well, I know how to code. I should just start building things and maybe start  a company, because I’m not happy working myself to the bone for a grade.’ I didn’t really have the desire to go and set the curve on some math or computer science test. There were people who wanted to do that, but I didn’t. I wanted to build something.”

Shirazi credits his education to his teachers at M-A and his experience interning at Facebook. “Facebook was sort of like my college experience,” he said. “I would work on all these new features, and then millions of people would use them—I learned so much there. I realized that if you have a good idea and you can build it, you might as well try; you might be pleasantly surprised with the results.”

That outlook empowered him to found his own company, Radius, a customer data platform. He explained, “At Radius, we built a solution that helped companies optimize their sales and marketing processes. We had many large customers like Comcast and American Express and scaled the team to about 150 employees.”

“Running a company is one of the most difficult things I have ever done,” he continued. “When you build a company, it is kind of an emotional exercise, because you’re raising something brand new that’s completely your own. It consumes your entire life, and you have to put all of your effort into it. There are so many different dynamics at play. Competitors want to beat you in the market. Sometimes employees don’t get along, or an acquirer decides not to buy your company after multiple rounds of conversations and signing legal documents. You always have to be on your toes and ready to deal with many different types of situations.”

“When you try to go out on your own, you quickly realize that the world is a very difficult place,” Shirazi said. “Once you’ve crossed about 50 employees, you’re just dealing with people’s problems all day. You’re trying to get everyone to row in the same direction, and people have different ideas and opinions. You have to figure out how to get everyone excited about your vision—to get them to unite around a common goal.”

“I love the early stages of starting a company when nothing is figured out yet and you’re starting from scratch. The whole process is quite fun because there are no rules—there is no instruction set, or manual, or roadmap that says how to build a company.”

Shirazi sold Radius in 2018 and joined Gradient, Google’s AI fund, in 2019. There, he invests in startup companies leveraging artificial intelligence and cutting-edge machine learning. “We invest in a lot of people early on in their careers—we take chances on people if they have good ideas,” he said. He was an early investor in many successful companies, including Lyft, Mural, Udemy, Carbon Health, and Palantir.

“I look for two key qualities in the founders of the companies I invest in: resilience and trustworthiness,” Shirazi explained. “In every company that you start, there are going to be obstacles, and it’s hard to predict what those will be. You always want a founder who is able to problem-solve their way out of catastrophic situations.”

“Trustworthiness is also really important,” he continued, “If I’m going to invest money into a company, I need to make sure that the founder is going to use the money wisely—that they’re going to invest it in the business and not just use it to enrich themselves.”

Shirazi’s advice to current M-A students:

I think that there’s so much pressure on students these days. I put a lot of pressure on myself when I was in high school. It wasn’t fun to live in my mind. And I feel like there are a lot of high school students who feel that way. It’s a tough time—you’re learning how to become an individual and pondering who you want to be in this world.

Looking back on high school, the things that I remember that make me smile are the study groups that I had with my friends, the ski trips that I went on with my friends, prom—things like that. The stuff that doesn’t make me smile is the amount of pressure I put on myself to always be the best and thinking that I had to get into top colleges to be ‘somebody’. I was so beaten down by the college admissions process; I poured so many years of my life into it. I was rejected from every Ivy League. I was rejected from Stanford. I was rejected from MIT, where my dad went. I ended up going to Berkeley and that’s a great school, but I’m also a college dropout, and I’m fine. We’re already so advantaged to be going to a place like M-A that it’ll work out. If you do what you like to do, if you follow what really makes you happy, it’ll work out. Don’t let the concept of having to get into the best school grind you down. It’s not worth it.

If I could go back, I probably would have taken fewer AP classes and I would have enjoyed the time a lot more. I don’t think it would have made a difference in my success or my future career. I think I stressed myself out to a fault. There’s a balance and finding that balance is part of the journey.

On his favorite books, Shirazi said, “I love Sapiens by Yuval Noah Harari. Superintelligence by Nick Bostrom is great—that’s one of Elon’s favorites. I love The Changing World Order: Why Nations Succeed or Fail by Ray Dalio. I love A Promised Land by Barack Obama, Shoe Dog by Phil Knight, which is about Nike, and also Only the Paranoid Survive by Andy Grove.”

In his free time, Shirazi is a “big kiteboarder.” He explained, “It’s kind of like windsurfing. You have a kite and then you’re on a board and the kite pulls you, and yeah, it’s pretty fun!”

Shirazi’s next big adventure is being a dad. He said, “I love spending time with my family, especially now that I have a four-month-old son. He’s just so awesome and fills my heart with love. I try to spend as much time with him as I can.”

Caroline Pecore is a senior in her first year of journalism. Her column, "Bears Doing Big Things," runs every Monday. She enjoys meeting new people through journalism and writing about the M-A community. Outside of school, she spends most of her time rowing for Norcal Crew and also enjoys reading, drawing, and exploring the outdoors.

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