Meeting Sahil Lavingia

PLUS: Tiny Radioactive battery, Levels of Wealth, Printing Money and many more...

Jan 22, 2024

hi 👋 Prado here

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Every Friday, I publish one essay & 10 interesting things that help readers become healthy, wealthy, and wise 👇

Essay of the week - Meeting Sahil Lavingia

Who’s Sahil Lavingia?

Sahil is the founder of Gumroad and one of the best writers on the internet. I had come across him on Twitter back in 2019. He’s one of the reasons why I got into writing.

I read Naval, Sahil, Julian, and many other interesting people who were successfully able to compress & simplify huge amounts of information into 280 characters.

It was a skill I wanted to learn and these people were the masters of it. Saying more with less.

Meeting Sahil

I’ve been a user of Gumroad for the past 5 years. Absolutely love that product. More importantly, Sahil has always been open about everything. One of the real entrepreneurs building in public and sharing his learnings. Providing value throughout.

When I heard Sahil was coming to BLR, I knew I had to meet him.

I joined the Telegram group and started making a list of questions for Sahil.

Now, I knew I wouldn’t be able to ask him lots of these questions, but I was prepared.

Just like I was when I had gone to meet Derek Sivers 👇

Meeting Derek Sivers

Prado 🔑

February 19, 2023

gm 👋 Prado here We are 3930 interesting people reading the newsletters every week. Every Friday, I publish one essay & 10 interesting things that will help you become healthy, wealthy and wise 👇

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I entered the place, and it was packed. Sahil probably had 50-60 people around him.

My friends and I met some new and old friends. It’s around 11 PM, and Sahil only has ten people around him. I knew he would be around for at least a couple more hours. It’s time. I opened Roam Research and had my questions ready.

I want to get to a place where I’m able to remember these questions without checking my phone. It’s awkward to ask questions while staring at a phone. It’s distracting.

Anyway, I’ll share some of the interesting answers he gave:

My very first question to him was:

How do you decide what to work on next?

Sahil shared that his goal is to become the president of the United States of America. Now, you reverse engineer from there. Interesting way to look at things.

The Gumroad Story

When Sahil was 18 or 19, he joined Pinterest as one of the first employees, and a few months later, he got an idea and started working on it.

He raised $8M as a 19yr old, went from 1 employee to 20 employees, and back to 1 employee in 2015 (I think you should check out Sahil reflecting and writing something called “My Failure to Build a Billion-Dollar Company”). Read it here

My prediction is that Gumroad will become a billion-dollar company in the next 5 years 👀

Few other info on Gumroad shared by Sahil:

He takes $400k as a salary from Gumroad and $400k from his VC firm.
Gumroad today is worth around 100-150M and wants to acquire Kickstarter, which is about 200M 👀)
Gumroad doesn’t have an office and only does one call every quarter. Sahil runs Gumroad in one of the most unorthodox ways possible. Read more here
He doesn’t like doing work retreats. He believes every year itself is too much.
It should be every 15 months or something. Because the moment you make something yearly, it becomes a thing. Around 9 month mark, everyone be like “ah, the yearly retreat will be happening.”

I understand this philosophy. Maybe you make this a pilgrim thing rather than the yearly summer holidays.
After Gumroad went from the Subscription model to 10% flat - a total of 7% creators left. But the profits doubled. I think it’s more.
He raised $5M through crowdfunding for Gumroad and can now raise up to $75M. Imagine every creator on Gumroad owns a part of Gumroad and gets dividends every year.
- Another interesting idea from this is to imagine a consumer-based product raising $75M from the crowd, and now the users are also owners of the product—one of the best ways to reach PMF and maximise network effects.
- He’s building Flexile, which can help you do this and more.
Gumroad might get an office this year in NYC. I joked and said, “Oh nice. It’ll be interesting to see Sahil doing a 9-5 around five days a week.” He said, “yeah maybe around 12-3PM or something like that”

Standard Salary for Everyone:

I asked this question to Sahil because he was one of the only business owners outside India who hired someone and paid them the standard salary. Another one I know is DHH and Jason Fried from 37signals & Basecamp. (read this)

I started the question with, India is known for being a country that has cheap labor and hard-working people. Everyone paid Indians 3 times less than the US and got the same amount of work done.

Sahil believes there should be a standard pricing worldwide and not just a country.

What’s the most expensive thing you own?

First, he said it was his Tesla, but then he said it’s probably the $7k/month rent of his place in NYC 👀

Who are his top 5 friends?

I asked Sahil this question, and he said no one. He just read books most of the time. He rarely goes out and prefers reading books.

Many people were still around at 12.30 AM, and everyone waswas asking questions. I was able to keep his attention for a little while as I had some banger questions with me. I asked a lot more questions, but I’m only sharing the most interesting ones.

this was the last group photo at 1AM (goatfish folks are in the picture)

The night took a weird turn

It was 1AM, we all had to leave the restaurant. The guy who was helping Sahil organise this event wanted to take Sahil to his place for an after party. I somehow got in and went with Sahil.

We chilled for about 20-25mins and then a guy said, Sahil can I ask you a question and then he asked… “If we kidnap you, how much money would you give us?”

I was sitting right behind Sahil and I was the only one who was an outsider. Everyone else in the room was his friends or roommates.

I looked at Sahil’s eyes and they lit up. There was an awkward silence around and some of the boys tried to diffuse it by laughing it out.

Sahil stood up and went to the washroom, and when he came out, he said he was leaving as he had a call in the morning. It was 2AM and it’s been a long evening + night.

I think I understand why he wanted to leave 👀

After leaving for home, I sent him a text to ask if he had taken the joke in the wrong way

when I met Sahil next time, he told me that if he ever does standup comedy, he’ll be talking about this story 😂
i’m glad he’s pretty chill about it.

I got an opportunity to meet him again before he leaves town.

I had slept at 3.30AM and woke up at 6.30AM. Took a shower and left to meet him at 7AM

I was able to have another amazing conversation with him.

I asked him these questions 👇

What are the three things you’ll do if you become the President of USA?

Flat tax slabs (Labourers pay the least amount of tax)
- He’s not saying tax the rich. He’s saying tax the poor less.
He believes in UBI (Universal Basic Income)
- Disagrees with Naval on this. (I would love to hear them have this conversation)
- He says everyone should get $1000
He never told us the third point. He had to leave.

Skyscrapers

Sahil wants to own a Skyscraper in NYC (which costs a minimum of $100M)

This reminded me of something he had written on the TG group - “I bet against the US and won - said no one ever (yet).”

I asked him if one of the people who was betting against the US was Balaji. Why do you think buying a skyscraper in the US is better when you can buy 10 skyscraper in India?

Then we went on a long rabbit hole talking about US innovation and the future.

He loves BLR, though. He said he’d shift to Bangalore before going back to San Francisco.

It was refreshing to have Sahil explore India and its future. I believe he’s one of the what I call a High Impact or High Value Individual, and it’s important to have some kind of dialogue with him.

I honestly believe he’ll become the president of US one day and there is a probability that someone he met in India becomes the PM of India. Imagine the odds.

Rough draft of this newsletter 👀 (wrote most of it from memory and during research of looking for questions)

I hope to meet and maybe work with Sahil in the future 🙌

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10 things from InterestingRoad.com 🙌

1. A tiny radioactive battery could keep your future phone running for 50 years (Blog)

2. Something from my Twitter👇

reply with your answer 👀 (might be writing about this in the next newsletter)

3. Interesting 👀

4. Mega list of 1 on 1 meeting questions (Blog)

5. Interesting website of the week:- Printing Money

6. Question of the week:- when was the last time you said “I don’t know”

7. Picture of the week:-

Source

8. Current game I’m playing: Fortnite

9. Meme of the week:-

10. Quotes of the week:

The pessimist complains about the wind; the optimist expects it to change. The realist adjusts the sails. - William Arthur Ward
(Tweet this quote)
“The person who writes for fools is always sure of a large audience.” ― Arthur Schopenhaue
(Tweet this quote)
“Death leaves a heartache no one can heal, love leaves a memory no one can steal.” ― Richard Puz
(Tweet this quote)