Antiportfolio

In venture investing, an antiportfolio is the most successful companies we could have invested in, but passed.

I was thinking about this topic more broadly. What are some life decisions that I contemplated but ultimately made the wrong choice.

It’s important to be aware of our errors of omission, especially the ones that form a pattern. So we can avoid similar mistakes in the future.

• Not being more involved with math and computer olympiads. I participated in various STEM olympiads, but never joined a team or sought formal preparation. I don’t think I’d have been a world champion, but I was among the best in my state without preparation so I would have done well.

• Not repeating my last year of high school when I came to America. The public school in Ashland, MA told me I wasn’t allowed to do my last year of high school again because I had already graduated. I should have lied, gone back to school, and integrated faster into American society. It would have also helped me in applying for college.

• Not applying to more colleges. I applied to UMass Amherst because it was a cheaper state school and my stepbrother Yuval was going there. UMass ended up being a great experience for me, but I should have applied to higher-ranking colleges, and would have probably been accepted. At the time, my mother and I didn’t understand that listed tuition is not the whole story. At least I had the foresight, after visiting a community college, that I wasn’t going to take that route.

• Not starting to invest earlier. I didn’t invest a meaningful portion of my assets until after I left Amazon in 2020. Because I had a retention package in stocks, I was involuntarily invested starting in 2017. Before that, I held $200k in cash for many years. I also missed investment opportunities around my graduation in 2009.

• Not applying to more than just Berkeley for transfer. At UMass, after being among the top in my class, I decided I should try to transfer to a better school. But for some reason, I decided it had to be Berkeley, which is harder to get into as an out-of-state transfer than Stanford. I have no idea what went through my mind. Maybe I was leaving too much of it to serendipity. Mistake.

• Not going to Stanford or Cornell for an MS/PhD. After Cisco, I applied for PhDs and I got accepted into Cornell and the University of California, Santa Barbara, where I eventually went. I also got admitted for an MS in Engineering Management at Stanford, but I would have to pay $30k or $40k per year. I should have probably gone to Stanford for a couple of years, if for nothing else than to give my future self an ego boost. I would have stayed in the Bay Area and increased the power of my network and the probability of my career bets.

• Not paying more attention to BTC in early 2011. In fact, I had several BTC, which my friend Alex sent me for free, and I lost them. I spent an entire week trying to convince colleagues to put $10k into BTC or build a mining rig and keep it in the office basement. My then-boss, Kevin, spent a lot of energy telling me I should stop wasting my time. My agentic spurt dissipated, and I didn’t do anything about it. At some point, I owned $5000 in BTC at $200 in Coinbase, which I should have just forgotten about.

• Not investing in NVIDIA when I first learned of CUDA in 2015 at $0.5 (split adjusted). I’ve talked about owning and have actually owned NVIDIA many times, and I understood its importance to AI. But I never bet with enough conviction or held my bets. My biggest mistake was while we were building Unwrap. I was having an incredibly difficult time getting access to GPUs in 2021 and still didn’t connect the dots and make a high-conviction bet.

• Not going all-in on AI when I learned of Word2Vec. I was an early peruser of AI when Word2Vec was launched. I found the research fascinating and played with the models for a bit. While I continued to develop myself in the field, at that moment I should have dropped everything and gone all in.

• Not making an aggressive push for director at Amazon. I had the scope, results, and leverage to become an L8 at Amazon in 2019-2020, but I was contemplating leaving and I thought it would be dishonorable to push my manager for a promotion and then leave. But the reality is that I had already earned the position, and that title is worth something in the open market. Besides, I didn’t know for sure I was going to leave. It makes sense to keep playing the game at the highest level, up until the second we leave.

• Not keeping a property in 2018 when buying another property. We sold the old house to buy the new one. In cash, because my wife didn’t love the idea of a mortgage and I didn’t love the idea of having renters. We should have kept both and dealt with the hassle of renting. The reality is that acquiring real estate at reasonable prices is only possible once in several years.

• Not keeping $50k of Tesla at $17 in 2018, instead of immediately selling because my wife thought Elon had a bad moral character and would bankrupt the company. I was recently married and felt I should consult my wife on every trade. These days I manage our investments more independently. This was the kind of high-conviction bet that only comes once in a while and for which we have to act assertively.

• Not waiting to buy the dip in 2021-2022. I was in the enviable position of holding most of my wealth in cash in 2020. I bought some S&P 500 in March 2020, at the perfect time, but not nearly enough. Then I waited, and waited, and when the tech stocks started pulling back I bought losers all the way down. I realized $400k in losses which could have been millions in gains.

• Not seeking advice before willingly and proactively giving ALL my equity in Unwrap to my co-founder, Ryan. I founded Unwrap in 2021 and approached the Allen Institute because I deeply believed that NLP would change the technology landscape. I thought NLP would have its ImageNet moment soon. After some founder dating, I partnered with Ryan, whom I knew and respected. I was “source” in driving the maze exploration and setting the foundation for the company. Six months into it, I started to feel confused and depressed. I don’t know if it was the isolation of the pandemic, my fear of failure, or something else. But I decided to leave Unwrap and join my former boss Kevin to found ScOp Venture Capital. I felt terribly guilty and depressed, and without consulting with anyone, I gifted all my equity to Ryan. There’s a nuance in that our vesting had a 12-month cliff, but at the same time, I controlled the company with 60% equity. I should have negotiated an arrangement where I kept 2%-5% as part of my important contribution, even if short-lived. Unwrap is doing very well, and I can’t take credit for any of the execution results, only for crafting its foundation.