My Interview for a VC Internship Was an Epic Failure (But I’m Glad It Happened)
Last April, I saw a posting for a full-time associate role at a new venture capital fund, founded by two individuals whom I had respected for a long time. I was a freshman at Princeton, but VC is my dream career and I was convinced (and still am) that a college education does not teach you the critical reasoning skills one needs to succeed in VC. So I applied. One of the partners replied and said they were looking for someone more experienced for the role, but were willing to meet me in September to consider me for a future position. I was stoked.
In waiting for the summer to end, I read dozens of books on mental models, decision-making, and investment philosophies. I thought the most important thing I could do to prepare myself was to hone my high-level thinking skills. To put them into practice and demonstrate my passion, I made a 10-page analysis on one of their portfolio companies.
Finally, September rolled around and I met up with one of the partners. We had a great conversation for two hours, and afterwards he told me to reach back again in January if I was interested in a summer internship. He also mentioned that VCs should be market-focused, because good markets can uplift bad products and sub-par teams. So for the next three months, I put together a 15-page investment thesis on the fintech market in Singapore, Indonesia, and Malaysia, a topic on which I had no prior knowledge, but was genuinely curious about. Included was an analysis on the risks regarding all of the firm’s portfolio companies. I also continued spending all my free time trying to refine my decision-making processes. The Checklist Manifesto, Principles, and Seeking Wisdom were among my favorite books on this topic.
I walked into their office in early January ready to kill the interview, confident that after 8 months of preparation, I would finally be offered to join them. The meeting started off well enough; I told them about myself, why I wanted to do VC, etc. But then they asked for some specific opinions, and it all went sideways. Below are the five biggest mistakes I made:
My first mistake was that I knew very little about the first company I brought up. We were talking about AI, and I gave the car insurance company Root as an example of how AI is drastically improving the way risks are underwritten. The partners then asked for my opinions on Root’s business model, whether I had reached out to anyone working there, and whether I’d tried to intern for them. The extent of my knowledge about Root came from its YouTube commercials, and needless to say, my answers were bad. Life lesson here is to avoid talking about things you only have chauffeur knowledge of.
My second mistake was not having a clear idea of how my own experiences related to our conversation. When they asked me why I hadn’t tried to learn more about Root by reaching out, I should have outlined how I did that for two other startups, Titan and MindMeet. In the latter’s case, I actually ended up working as a PM intern for four months. But I was so busy trying to make my answers regarding Root sound less terrible that I forgot everything about myself. The interview was quickly spiraling out of control.
My third mistake was that I spoke in very high-level abstractions. Remember how I said I was focused on developing my critical thinking skills? Turns out I should’ve spent a lot more time reading about specific companies. My reasoning for not doing so was because I didn’t trust myself to develop opinions when I didn’t know how to do so effectively. Ideology is extremely dangerous, and I wanted to guard against potential confirmation bias in the future by avoiding developing opinions now with no one to stress-test them with. Instead of talking about Root’s business model (concrete), I likened the transition from insurance quotes being based on demographics to Root giving quotes based on individual driving abilities to the ongoing social struggle between group identity and individualism. I brought up some other points about how tech, society, and philosophy intersected to show I was a nuanced thinker across multiple dimensions. While I’d argue that’s an important skill for living a meaningful life, I’d also recommend not talking about that if you are interviewing for a low-level role in VC. You are there to filter deals, and to do that effectively one needs to have a concrete understanding of specific markets and players.
My fourth mistake was that I had prepared a bunch of questions to ask at the end about why they invested in specific companies, but the interview went so poorly that I should’ve asked what I should do to learn about specific companies while in college, what I could’ve done better, etc. But I was so disheartened at how terrible the interview went that I didn’t even think to ask those questions. And in doing so, I likely blew my chance at ever working for them again. I came off as a thoughtless fool who didn’t even care enough to ask how I could improve.
My fifth mistake was that I spent too much time worrying about what kind of person they would perceive me as instead of how I could specifically help them. One of the reasons I respected them so much was because I loved their contrarian-style thinking, so I read through their personal blogs, stalked them on YouTube, and followed them on Twitter so that during the interview I could reference things they’ve said and tie them to my own ideas to show I was a like-minded person (which I believe I am). Terrible idea. When they asked me to name three unique skills I would add to the firm, I had no solid answer. Life lesson here is to just be authentic and real will recognize real; there’s no need to force things.
I was dreadful. Wholly unprepared. Embarrassed beyond belief. The partners told me I had “no opinions of my own” and were clearly frustrated. After 8 months of working tirelessly to get the chance to sit across the table from the them, I choked it away in one quick hour.
It is not an exaggeration to say that the following week was the most mentally painful of my life. It’s not every day that you are told by two people you highly regard that your dream career might not be for you.
One of my most important life philosophies is stoicism, which basically states that it is irrational to feel negative emotions towards past events because nothing will change them; the only practical and logical path forward is to better prepare for the future. While to this day I’m still upset at myself for dropping the ball, I am also grateful for the experience. Since I put myself in the position to fail at age 19, this means if I can honestly internalize and learn these mistakes then I’ve saved my future self a lot of pain. In my all-time favorite book Principles, author Ray Dalio gives a very useful framework for thinking about mistakes:
“I learned that there is an incredible beauty to mistakes, because embedded in each mistake is a puzzle, and a gem that I could get if I solved it, i.e., a principle that I could use to reduce my mistakes in the future. I learned that each mistake was probably a reflection of something that I was (or others were) doing wrong, so if I could figure out what that was, I could learn how to be more effective. I learned that wrestling with my problems, mistakes, and weaknesses was the training that strengthened me.”
So what will I do differently heading into the future?
Firstly, I actually don’t think I was wrong to spend the majority of the past few months learning about mental models and psychological biases. Every day I see people, including myself, make bad decisions because of recency bias, commitment bias, ideological bias, etc etc etc, so I do not regret my decision to focus on how to think generally before pondering about specific companies. However, I should’ve spent far less time worrying about what they would think of me as a person and more time on showing what concrete value I could add to the firm. Although learning how to think is a never-ending journey, I finally feel ready to begin forming my own opinions, given my level of open-mindedness and awareness of my own biases. By the time I have another interview, I will have deep, concrete opinions that I am confident in, not just surface-level understandings.
Secondly, I never, ever, want to feel the pain of such a rejection again. This experience really made the phrase “It’s tough to break into VC” real, so I need to work harder than I ever have before. I mistakenly thought I would have some breathing room as a student in terms of what people expected from me. But with thousands of startup employees, bankers, MBAs, and fellow undergrads trying to break in with me, that is not a viable mentality for where I want to be, and it shouldn’t be for you, either. To break into VC and succeed once you’re in, you have to already be thinking and acting like one, so it’s time to accelerate my learning loops, take responsibility for what I know/don’t know, and become the person I want to be in 10 years in the next six months.
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