Sahil Lavingia: Observing the Present [The Knowledge Project Ep. #98]

Sahil Lavingia is the founder and CEO of Gumroad, an online marketplace for creators. In this conversation Sahil and Shane cover building a billion dollar business, the most critical skills for success, how he hires, his worst mistake, the patterns of success and failure and so much more.

Here are a few highlights from the conversation:

I think expectations cannot be underrated. I think your peer group also can’t be underrated. I think there’s so much emphasis on the system that you’re a part of, your set of teachers, etc. But honestly, I think the biggest thing is just you’re the average of your five friends.

When you go on your phone, you’re seeing the way that a certain group of people see certain things. I think this has actually been accelerated with COVID, because you don’t have maybe some of the back and forth. It’s this very asynchronous medium. So, you end up just absorbing all of this content. Your perception is your reality.

Before I even wanted to fundraise or thought about it as an idea, I felt like I wanted to be a founder. So, I spent a lot of time hanging out with founders, hanging out with early employees, working at an early stage startup. I think that’s the best thing that you could do.

I wish I knew earlier that my company was still my responsibility. No one was going to fix my problems. They were investing, because they believe in me and they believe in my potential, but it was up to me to still take that potential energy and turn it into kinetic energy. It wasn’t a handout. It wasn’t like you’re going to get these people to come into your office and help you solve problems day in, day out.

The skill that’s been really top of mind for me right now is the ability to save other people time. Basically, what I mean is there’s certain people that go about their lives, I try to be like this, but they just operate in a way that requires less of everybody else for the equivalent amount of success in that relationship, right?

Those are the people that I look for, the people who want something so badly that they just figure out how to do it. They’re okay with not maybe having their first thing be just the dream project. They just get started, and then they figure things out as they go.

The filter that I use is if you remove the social incentive, so much of this you’ve done because of the social incentive, it’s to comment, it’s to go to work and talk about something. The reason I think people don’t often read a lot of these old books is because the social incentive goes away. You read this book and then you’re smarter, but that’s it.

That’s what being present is to me, is just really focusing on the present moment and noticing as many things as possible, which sounds easy, right? It’s almost paradoxical. You’re obviously here. What does that mean? You’re obviously looking out through your eyes. You’re smelling things through your nose. But if I said, “Okay, how many times did you blink in the last three seconds?”, you wouldn’t even remember the last time you blinked.

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