A Conversation about Sahil Lavingia
We love consuming books, podcasts and articles that are aligned to our manifesto. If you missed it, we had penned some thoughts on a recent podcast on Noah Kagan Presents, titled How to Run a $100M Company Without Meetings (w/ Sahil Lavingia). However, this interview with Sahil was so inspiring to both of us we decided it was worth having a longer conversation about.
The following is an excerpt of that conversation — hope you enjoy it!
Why this podcast was worth listening to?
Felix:
Sahil Lavingia was on the podcast Noah Kagan Presents. So he brought on Sahil Lavingia, who I've never heard of before. He founded Gumroad awhile ago now. Sounds like it's been a decently long journey. He was in Silicon Valley and he was Pinterest employee number TWO.
Howard:
I actually had to listen to it a couple times because there's SO MUCH packed in there. One was drawing! He wants to be one of the top 100 figure drawers in the world. And then his view on money, work, and free time where he took it to the next level.
Felix:
The title of the podcast was “How to run a $100M company without meetings.” So I thought, this is going to be interesting, about productivity tools and how you schedule your day.
But as soon as you got into the interview, it's just shock after shock of him breaking down status quo barriers. And what really struck me was just how committed he was to designing his life. Then just having an unrelenting and unapologetic attitude towards doing that, both at work and at life.
Becoming World Class at something - Flow State:
Howard:
He's so comfortable at defining his boundaries and is completely transparent. I really liked how he broke it down – if you spent 20 hours a week on something then you can be world class at anything in 10 years.
Felix:
I totally agree. The other part that resonated with me was tackling something that's really hard. And he admits it, he’s never done this before. When he was getting into figure drawing, he talked about how he could only do it for 10 minutes and then he was exhausted.
And one of the pieces that is really gratifying for him is that when he shows himself that he can conquer something hard, like figure drawing, he actually feels like he can conquer the world after that. When he goes back to work, he feels more confident. That practice and mastery of something hard is giving strength in other parts of his life.
Howard:
Just that focus time, really getting into the flow is awesome. Not only is there great work output, but your life becomes so much more fulfilling when you can spend more time in flow. That's definitely one of my goals - spending more time in flow!
Felix:
That's definitely one of my goals as well. And I love how he's just made such an intentional decision to do that for up to something like six hours a week now, and he wants to probably do more! He's designed his work life in a way that he can devote 20 hours a week to something specific – and imagine 20 hours a week in flow state. That's bliss, right?
Topic of Money
Howard:
Sahil talked about how he really didn’t see life costing a lot and he feels like he doesn't need a lot of money. And he was so transparent in saying that he actually just spends $4,000 a month and half of it is on his mortgage. Everything else is just eating out or a couple of small expenses.
Felix:
And he's been able to authentically find joy in those little things. He talks about his cat, which was like $50, and he expects it to live 15-20 years. And he says it's like a dopamine stress ball whenever he needs it. The ROI on that is immeasurable. And they talked about a Spend to Enjoyment Ratio where he gave tons of examples, like his drawing hobby. It's a hobby where the cost is paper and pens/pencils or whatever your choice of instrument is. I love that outlook and I love the point of view of looking for things that give you that value, and also looking for hobbies that are cheap and fun.
Howard:
He talks about how he'd much rather invest money than spend money. And as long as you have enough money to say no to stuff, you don't have to meet people you don't want to meet with, you don't have to take a job that you don't really want. That's pretty awesome! Being able to get to that point and have control over your own destiny.
Felix:
I heard about a related interesting term called “work optionality.” I love that. I love that independence part of it, because it's the freedom to say no, or the freedom to spend the time how you want. That's what he's really been shooting for and gotten there! And that's allowed him to chase a dream of being the best, the top figure drawer in the world, which is really cool.
Howard:
There's so much to aspire to here. I would love to hone some craft where I could be great at. And how do you build a company that is successful, and it’s solving a really relevant problem? Another really cool aspect was how he only spends 20 hours a week on being the CEO of a successful tech company. That’s so crazy!
Topic of Time
Felix:
That's insane. At the end of the podcast, Noah asked him what his schedule looked like. It goes back to him just being transparent about how he operates, which translates into how he operates Gumroad as the CEO. In this interview, he basically said “I'm a no meetings guy.”
And then with no meetings, compared to the next tech CEO, he’s literally freed up 20 hours of his week! I was nowhere close to being a CEO in my middle management role but even then I was easily pulling like 35+ hours a week in meetings. So I can completely see how even that one change that he's been very intentional about making has created that much time for him.
Howard:
Amazing. It’s so fun to hear that! And also how he is making sure he has time to go grocery shopping with his wife, and play video games. Just making sure there's fun time in their day as well, which is pretty awesome. So many fun ideas to aspire to!
Felix:
One of the themes that I really glommed onto, to encapsulate some of that: he's spent the time to audit his life and he’s basically said: I have a bucket here of activities and people, that gives me energy. And over here is a separate bucket of those things that take away my energy. And he's been super diligent about maximizing the ones that give him energy and eliminating or minimizing the ones that don't.
Howard:
It would be a great exercise to get crystal clear on things that you'll tolerate and things that you don't want to have in your life? And then essentially eliminating things that don't fit that mold for you. And then also being able to creatively solve for those things that take energy away from you. I would love to be able to think the same way! How do we find that creative solve rather than following the “proven approach?”
Felix:
Oh yeah, one example is how he says ”Oh, this investor thing is just going to take too long and that sucks. So I'm just gonna redesign that!” Or is there some audit process that he follows that we can all learn from? I'd be super interested in trying to figure that out.
Key Takeaways
Felix:
What a great podcast. I think it would be interesting to hear from you: Is there one lesson that you're going to take away and try to act on?
Howard:
I love what he said about getting into flow. He makes it sound so easy, in a way. Just spend 20 hours of your week in a flow state. So for me, how do I prioritize more of that? Equally loved how clear he was on his boundaries and knowing what he wants and doesn’t want in his life.
Felix:
That really resonates as well as how much time you spend in that flow state because that's when I feel you're solidifying those gains. Or really kind of building those neural pathways in your head around how those skills manifest. So I agree with you, spending more time in that flow state, and as much time as possible, is totally a noble goal.
Howard:
What was your biggest takeaway?
Felix:
I think there’s this whole thing around understanding what those buckets are for ourselves. Let's say you start finding that a woodworking project is just engulfing you and you love it. Then it’s about how we either build that into our business or not. If we don't, how do we continue to make time for us to pursue those things, and us to spend 20 hours a week doing those things that aren't related to the core business. So I think if I was going to sum it up in one thing, it's how we continue to design our journey to maintain those principles that we're making room for, for mastery.