Venture Capitalist Firm Partner Discusses Qualities of a Successful CEO

Ajay Kamat is a partner at Pear VC, a venture capitalist firm, which was one of the earliest investors into the food-delivery business. On Wednesday, Kamat was invited to give a talk about his career and experience as an entrepreneur by Corner Office. Corner Office is a new club on campus dedicated to bringing in speakers that talk about “real life skills” with a focus on business and finance, according to Isaac Hershenson ’20, Co-Head of Corner Office.

During the talk, Kamat talked about his past experience working as an entrepreneur and CEO and his current job at a venture capitalist investment firm. Some of the companies that Pear VC, Kamat’s current firm, has invested in have been Doordash, the audio exercise software Aaptiv, and many others. Among other topics, Kamat spoke about how his career influenced his growth as a person, making him more resilient and encouraging him to constantly be improving.

“Being an entrepreneur, you really learn to have thick skin. I pitched almost one hundred investors, ninety-five of them said no. And you know, that was the first time in my life I faced a lot of rejection and learning how to take that rejection is a huge life experience for me, which I’ve gained from a lot. And so kind of along the way, and all the jobs that I’ve had being an entrepreneur, being a founder, being an investor, if I’m not learning and I’m not growing, and I reflect back every year on if I am, then you know, I know that it’s time to do something else.” said Kamat.

Kamat discussed his day-to-day interactions with companies as a prospective investor, and how he’s picked up on indicators throughout his career on the CEOs that will make or break a company. In his talk, Kamat laid out two characteristics of successful CEO: one that is passionate about their company and its mission and one that is incredibly resilient.

“There are obviously some traits of the founders that end up being successful that I’ve noticed. Number one is, they really know their space really well, like they’re a PhD in it. And if we ever know more about an industry or the company than the founder…it’s a really really bad sign, and it happens way more often than you’d think. So some of them spend months, years, just thinking and meditating over how the industry works and why their product is, what the strategy should be for their product, they really know the ins and outs of it.” said Kamat.

Kamat continued, emphasizing how often successful CEOs are produced through having been rejected, and not babied, “The second thing is that they have a ton of grit. You know, we work with a lot of founders that are coming out of top universities. Many of these people have privileged backgrounds and you find that sometimes people who have never heard no, like everything in their life has been a yes…when you start a company, you know, reality is going to slap you in the face. Companies are really hard to build. And when things get hard, sometimes people quit. And way more people than I thought actually quit when things get hard. And so if we can see any indication of a person’s background that they don’t give up and they’re going to see this thing all the way through, That’s a really, really important sign for us.”

The element of open-mindedness and passion within finance and specifically investment were reoccuring themes during the talk. Kamat stressed the importance of not trying to focus specifically on one end goal, but instead to invest time in what you care about.

“I really believe strongly in nonlinear paths. So like, sure, there are some ways that there can be a straight line into being an entrepreneur. And typically, those are if you could be a builder. So computer science, any sort of engineering, but that’s definitely not the only way…So I do think that the most important part is to focus on something that you really care about and you’re willing to put in more effort learning that than anyone else. And so you can only put in a lot of effort for something you generally care about.” said Kamat in his talk.

Max Levi ’19, Co-Head of Corner Office, echoed Kamat, explaining how he agreed that an academic path towards entrepreneurship was often misguided.

“I think Ajay did a great job at dismantling the argument for ‘go study entrepreneurship’. He explained there’s not a linear path. And for me personally, that was really important to hear. Because I think a lot of the time, students think it’s just, you’re just going one way, but life takes you in multiple directions. And I think he did a really good job at explaining that.” said Levy

Isaac Hershenson, the other co-head of Corner Office, laid out the mission of the club, which is only in its first year as a club, having been formed by Levy and Hershenson at the beginning of the fall term. Hershenson explained how they had felt that there was a lack of “real life” material being taught and exposed to students at Andover, especially at All-School Meeting (ASM).

“We’re just the club that wants to help teach kids at Andover some real life skills…things that we think that ASM doesn’t do a great job of doing, I really think it’s great what they’re doing but I think the school is losing a lot of value that they could be using without time. Kids here, just go into college and not really knowing what they’re doing. I think a little bit of the blame has to be on the school and we’re trying to fix that.” said Hershenson.

Levi elaborated on the goals of Corner Office, noting how they strive for every speaker to bring a sense of originality and individualism along with an in-depth, firsthand knowledge of their subject matter.

“Isaac and I came up with this idea in the fall and implemented it come the new year in January, on January 6, I think we brought in our first speaker. And now we’re on, this is our fifth speaker now. And we are monthly, month to month and we just look for people who we think would be interesting, people would like to see and can really teach the rest of us something that you haven’t heard or you haven’t thought about or just push you to actually expand upon your knowledge,” said Levi.