Author: MARIO GABRIELE. Translated by: Cointime.com
Actionable insights
If you only have a few minutes, here are the key points that investors, operators, and founders should know about Sam Lessin’s meditation.
Lessons from science fiction. Science fiction is often a source of inspiration for technologists. For Slow Ventures partner Sam Lessin, the parallels between the genre and investing may be the most interesting. Although through completely different mediums, both sci-fi world builders and venture capitalists are making arguments for what the world could be like.
The value of metrics. For many years of his career, Sam viewed metrics as limiting. He believed that focusing too much on certain numbers would "overconstrain" problems, hindering the ability to solve their root problems. But he has changed this perspective. Sam now sees metrics as opportunities, not constraints. Once team members are given a specific number to focus on, they are able to approach problems as they see best.
l Visionary and honesty. Founders are visionary by definition—at least in Sam’s opinion. It takes fruitful madness to change the world, disrupt incumbents, and reshape industries. Founders must balance ambitious idealism with inner honesty. For Sam, the ideal entrepreneur knows how to balance “strategic madness” with deep reflection.
l The hype of artificial intelligence. While Silicon Valley rushed to capitalize on AI startups, Sam largely stayed on the sidelines. Although he found the technology fascinating, the longtime venture capitalist saw that it was not a good area to invest in. Sam expected the value of the technology to accrue primarily to large, established businesses, with few new startups able to break through.
l Hit the jackpot. Throughout his investing career, Sam has had extraordinary success, investing in companies like Slack, Robinhood, Airtable, Nextdoor, and Solana. Despite these triumphs, he doesn’t consider himself a true investing craftsman. In his view, the best investors are not only right on the money, but bold enough to double down or even triple their investments. That’s how you get $10 billion back on a single, exceptional bet.
It’s no secret that investors in need of capital must portray themselves as bucking the herd. It’s a Silicon Valley way of doing things, and it makes sense. Venture capitalists, by definition, invest in companies that are almost doomed to fail, at least in the early stages. To counter the fact that small startups rarely outperform large, stable incumbents, and to tip the odds against them, the tech industry’s most adventurous financiers must ensure that, when they succeed, they succeed big. Barring some fluke or providence, the only way to pull off that “super grand slam” is to go against the herd.
There are different types of counter-trend thinking, some less common than others. The most common, undesirable version is the reflexive counter-trend. This investor cares less about the fundamental merits of a particular investment or position and more about where the market stands. Like a trader, this counter-trend person watches the opposing sides, calculates the odds, and chooses a position that suits them in hopes of generating financial or social capital. They are also willing to move positions as markets and sentiment change.
Sam Lessin is not one of those types of contrarians. As a partner at Slow Ventures and a former Facebook vice president, he can be called a true contrarian. He doesn't necessarily try to go against the grain; he just seems to see the world and the tech industry from a different perspective.
This talent has made him a very successful investor and a frequent spark for internet debate. In addition to backing teams like Solana, Nextdoor, Ro, Robinhood, and Slack, he also caused a stir by calling Calendly links “the most raw/naked display of social capital dynamics in business” and predicted the “end of venture capital.” Although he seems to enjoy being different, in conversation you quickly get the sense that his opinions on things big and small come from real thinking.
In this respect, he embodies Warren Buffett's famous quote about counter-trend thinking: "A business or a stock is not a wise purchase simply because it is unpopular; a counter-trend approach is as foolish as a strategy that goes with the flow. What is needed is thinking, not polls."
Sam's ability to authentically generate unique perspectives is something I greatly admire, and his willingness to share them, no matter how confusing they may cause, makes him an ideal subject for meditation.
If you weren’t in technology, what would you be doing?
If you asked twelve-year-old Sam what he would do, he would probably say make movies. The movie industry is a terrible industry, but it can be really fun. I particularly love science fiction as a genre, both in movies and books. In fact, when I worked at Facebook, I made every new product manager read Snow Crash.
I think there are a lot of parallels between science fiction and investing: You make a thesis about how the world might change.
Which modern or historical figure has most influenced your thinking?
I have two answers. The techie in me is Claude Shannon. Information theory is a really cool subject, especially when you consider how fundamental it is to our lives and minds. I actually have an original Bell Labs brochure that has Shannon's information theory paper in it.
My less obvious answer is Michel Foucault. At Harvard, I was in a program called Social Studies, which was a combination of history and economics. It was very useful for understanding the last 50 years of the internet. Philosophers like Foucault certainly didn't speak in technological terms, but they thought about a lot of social issues that were being dramatically accelerated by technology. Apparently, Foucault had some very dark theories about the world. But he seemed to be mostly right, right?
What is the most important thing you’ve changed your mind about in the past ten years?
When I started working in tech, I focused on what I thought were fundamental problems. I would get frustrated with people I considered “number optimizers.” These are the people who would spend their time saying, “Oh, we’re going to get X metric up,” or “We’re going to get Y metric up.” In the past, I thought that focusing too much on metrics was overly limiting in terms of problem solving.
I've changed my perspective. When you see how big companies work, you realize that for most people, metrics are very freeing. Without metrics, you're forced to micromanage everything, which is terrible for people working on projects.
It turns out that if you just say, "Hey, Bob, make that Z-index go up," Bob will feel better creatively.
That being said, if you are going to be metric driven, be sure to pick the right metric. If you give Bob a specific metric to increase, he will work to make it happen. You don’t want to find yourself in a paper clip optimization situation. Ultimately, focusing on metrics isn’t always the answer, but the mental shift from viewing it as a prison to viewing it as freedom was a personal progression for me.
What skill have you been honing throughout your life?
My first thought was about being a good dad. We have three young kids, and figuring that out has been a journey that has evolved over time.
Overall, I don't consider myself a craftsman. What I like is finding ways to learn things quickly - finding out what's really important.
When it comes to investing, I’m most proud of backing companies that others wouldn’t. When money is tight, that’s where you can make a real impact as a venture capitalist. No one wants to have “market participant” written on their tombstone. We’ve had some great returns over the years in the crypto space, backing companies like Solana. There are others that you may not have heard of, but that I’m very bullish on.
I’m also proud of companies that may not have had the biggest financial returns but were culturally significant. For example, I invested in the first and second rounds of funding at Venmo in its early days, and then had my dad invest in the third round because no one wanted to give them money. The financial returns were OK, but it was a great cultural investment.
For example, I was one of the earliest investors in Solana, but then other larger investors came in. The real craftsmanship is not just "let's just do the first round of investment", but to double, triple, quadruple the investment throughout the process, from the right direction to the right specifics.
What is the piece of art that you can't stop thinking about?
John Wick 4. It's going to be amazing. Honestly, I don't think there's any work of art that I can't stop thinking about, but I'm really looking forward to John Wick 4.
What qualities do you value most in others?
Be honest, with yourself and with others. Honesty with others is the most basic requirement. What's harder is to be honest with yourself and be introspective about reality. I think most people are very self-deceived. As an investor, I see this all the time. Entrepreneurs are almost crazy - almost by definition. If they were too introspective all the time, they probably wouldn't be doing what they're doing. You want to find people who can be crazy in strategy but also thoughtful and introspective in other ways. It's a fine line.
Of course, there are always exceptions, and some very successful people do not have this inherent honesty. One person I would name is Elon Musk. I think he is a complete fraud. Although obviously I missed the opportunity to invest in him, he does not have the honesty quality that I care about.
I keep myself honest by asking for feedback. I am perfectly willing to share bad ideas at high velocity and rely on others to vet me intellectually. I think this is a mindset worth cultivating: one where you are willing to admit your mistakes on almost anything all the time without dwelling on them. Trying to avoid mistakes is a path to being dishonest with yourself and others.
What is your most counter-trend and high-conviction opinion?
I have a lot of very contrarian views. That's my specialty. I pride myself on being contrarian. One of them is: I think artificial intelligence is a terrible place to invest. You have to separate the coolness of the technology from where the economic leverage is.
AI obviously has leverage, but it will almost certainly go to the big platforms. This isn't a PC or internet-level disruption. This is a simple add-on for cloud service providers or companies that already have attention or data. There will be exceptions. Someone will build a $10 billion AI company. There may be a few more. But 99% of the value will go to the big existing companies.
In this respect, AI may be more like the mobile revolution. Unlike the PC and Internet waves, the mobile revolution did not produce any $500 billion or $1 trillion companies. Sure, you had some new apps, like Instagram, but they were quickly swallowed up by bigger players. Uber is probably the only example of a pure mobile company that has managed to grow. And it wasn't that big - it was a $70 billion business that required a lot of capital. AI companies will need more.
Of which of our contemporary practices will our descendants be most likely to judge most harshly?
meat, but I fully intend to continue eating it.
What are the risks that we as a species have wildly underestimated? And what have we overestimated?
I think we have underestimated the risks with contemporary AI and overestimated superintelligence. Today’s AI has everything it takes to destroy trust between people and completely divide society. We don’t need anything more advanced than what we already have.
The thing about superintelligence is that everybody thinks we're almost there. But we're actually nowhere near there. It's like genomics all over again. We thought we were so close, we were going to get a copy of the genome. And then suddenly eighteen other problems pop up, and you find yourself just getting deeper into trouble. I think superintelligence is a really cool intellectual and philosophical problem, but I don't think we should think of it as a practical problem.
If you had the power to designate one book that everyone had to read and understand, which book would you choose?
The Lessons of History by Will and Ariel Durant. This is a great book and I regret not reading it sooner. If everyone read it, we would have a civilization that is more truthful about its history.
How will future historians describe our current era?
Imagine waking up in the morning and suddenly having superpowers. You could remember everything. You could communicate with everyone in the world for free. You could process unbelievable amounts of data.
We live in a teenage superhero movie where the hero gets super powers and doesn't know what to do with them. There's no Professor X to guide us.
In the first half of the 1700s, the British were crazy about gin. It was considered such a big deal that Parliament was forced to act. Through legislation and rising food prices, they eventually got it under control. I think the internet and AI are going to do the same for us. It changes everything about us biologically, so we’re going to be completely screwed for a while. But we’re going to work it out.
What do you consider to be your greatest achievement to date?
Without a doubt, my children.
From an investing perspective, I’m most proud of companies that no one else is willing to invest in. When money is scarce, you feel like you can have a real impact on the market as a venture capitalist. No one wants their epitaph to say “market participant.” We’ve had some great returns in crypto over the years, backing companies like Solana. There are also some that you may not have heard of that I’m very bullish on.
I’m also proud of companies that may not have had the biggest financial returns but were culturally significant. For example, I invested in the first and second rounds of funding at Venmo in its early days, and then I had my dad invest in the third round because no one else wanted to give them money. The financial returns were OK, but it was a great cultural investment.
As a product builder, I’m proud of some of the ideas I pushed early on that have become mainstream. I feel good when I hear that I’ve had an impact on someone else’s life, whether it’s through funding or ideas — knowing that I helped them move in a cool direction. I definitely like being right, especially when everyone thinks I’m wrong.