- The Pursuit
- Posts
- The Pursuit, Vol. 10
Breakthrough
Being Interesting
Last week, my firm threw its annual Silicon Valley Summit, where we bring together portfolio company executives for two days to trade notes, share some good food, and commiserate about some of the loneliest work in the world (being a founder). The Summit was a great reminder of the best part of my job: I’m constantly surrounded by folks much more accomplished and experienced than I am, and they are eager to share their wisdom. Several CEOs of multi-billion dollar companies were in the room, sharing just as eagerly as the baby-faced founders of the $20M companies. I love my job because I’m always talking to interesting people.
Take, for example, one of our portfolio company COOs. Over the span of two days, we discussed the following: the exact grain of leather my bag was made out of, which he identified by sight; his complete reorganization of a sales team; his time as a project manager at a > $100B market cap company; his time writing software for another > $100B market cap company; his recruitment of a key salesperson from the latter > $100B company; his love of motorcycles (hence the knowledge of leather, for his jackets); and his Revolutionary War-era cannon, newly purchased.
Towards the end of the conference, he taps me on the shoulder. “Sam,” he says, “I just saw your newsletter. It’s awesome. We should talk more. I was an English major and still occassionally write articles in [publication].” Holy shit, what doesn’t this guy do?
I thought a lot about this executive and his career path. There’s no way he could have planned it, even if he had 100 tries. On top of that, it’s ridiculously interesting and still in progress. How the hell do I become that interesting? I thought.
A few days ago, it finally hit me: Being interesting is just being interested, compounded. You can’t fake interest in leather jackets and motorcycles and war cannons. You simply are interested and pursue those interests. The type of man who has these experiences is the same type of man who asks someone 20 years his junior about their newsletter.
Reading
Writing on the Internet
Human brains are wired such that we get rewarded for attending to surprisal. If we turn our attention toward things that surprise us we get excited—and our model of the world changes. It grows more complex.
…
The people you will be able to have deep conversations with have, like you, already been surprised by the simple, clear things. They need more to get high. And this “more” will be wildly idiosyncratic. It cannot be summarized in a list of writing rules.
So what do you do?
You ask yourself: What would have made me jump off my chair if I had read it six months ago (or a week ago, or however fast you write)? If you have figured out something that made you ecstatic, this is what you should write. And you do not dumb it down, because you were not stupid six months ago, you just knew less. You also write with as much useful detail and beauty as you can muster, because that is what you would have wanted.
I’d highly recommend subscribing to Henrik Karlsson on Substack. I don’t read every one of his essays (as they are, per the above, incredibly idiosyncratic), but I always remember they exist when I need them most. This is a really interesting post examining how the network effects of the internet work, from a writer with over 25,000 subscribers to his essays.
Karlsson goes on to describe the compounding effects of writing online:
As you start routing information and putting out blog posts, you will begin to accumulate connections. Useful information will start to stream toward you, turning you into a small hub yourself. This will allow you to collect and curate information and route it back out, which will allow even more people to connect to you, in a flywheel that lets you do increasingly useful and good work. I especially enjoy it when intelligent people attack me; I then invite them to comment on upcoming drafts.
This is largely why I write this newsletter and use Twitter. One of our portfolio company COOs jokingly asks me how Mark Andreessen and Garry Tan are doing every time we meet, because they both follow me on Twitter. It’s a good reminder of how inconsequential an Internet follow is, but it’s also cool. Writing on the internet made these guys go from a loose two degrees away to a loose one degree away. I’ve been able to banter with some of my favorite writers because they like a few of my 280-character thoughts. I’ve met about a dozen brilliant young people in person over the past year because I read their research papers and decided to DM them to learn more. Heck, my firm even invested in a company that I discovered after their summer intern tweeted about it.
The Internet is a really magical place. For some reason, there’s this odd section of the Internet where yappers, well-read writers, and tech/investment-curious people intersect that is particularly magical. I’m very glad to be a small part of it.
My Best,
Sam
1 See this article about “TPOT” (“this part of twitter”), which some have self-coined this corner of the algorithm. I’d define myself as “TPOT adjacent” in that I have enough mutuals (most of whom I’ve never met) to know what’s going on, but have not hung out with or self-defined myself within the community. For context on the cultural significance of this amorphous group, here’s an article from The San Francisco Standard that tries to associate Luigi Mangione with TPOT. This was largely rejected. But attempts to define something journalistically, even when its credibility relies heavily on the Gell-Mann Amnesia Effect, mean a concept has crossed the Rubicon in some important way, at least to me.