100 Lessons from Sahil Lavingia
Welcome to 100 Lessons.
I’m Chris Harry (you can find me on Twitter @TheChrisHarry).
Here we explore the lessons learned from the greatest thinkers.
Sahil is the founder and CEO of Gumroad.
Gumroad exists to help every creative earn a living selling the stuff they make directly to their audience.
Previously, he was early at Pinterest — a service that lets users collect, organize, and share the things they are into — and worked on turntable’s mobile apps.
- Ship quickly
Sahil came up with idea for Gumroad. Built it over the weekend. And launched it Monday morning on Hacker News.
52,000 people saw it on the first day.
2. Making tough decisions
Gumroad wasn’t growing quickly enough to keep up with the demands of investors. To keep the company alive, he laid off most of it’s employees.
3. On helping your customers
Gumroad’s customers are the creators that sell on the platform. The better they do, the better Gumroad does. Sahil launched a small product lab to teach new creators how to grow and sell.
4. There’s always a business in helping others
Gumroad has sent over $178 million to it’s creators.
Plus there’s the impact those creators have had on there customers.
5. On Transparency
In 2018, Gumroad began sharing it’s numbers publicly.
Since then, a host of people have begun building in public.
6. Reassess your goals
Sahil wanted to build a billion-dollar company. Instead, he now focuses on building the best product for his customers.
7. On expectations
As a founder, know what investors expect from you.
8. You are the average of your five friends.
Sahil spent a lot of time with founders and people working in start-ups.
9. On hiring
Look for great communicators, strong writers, and people who know what they want.
10. On Tweeting
To write a great tweet, learn to be an observer.
If you’re enjoying this, I’d appreciate a retweet of this thread on Twitter.
11. The one thing
Focus on the one thing you are doing right now. Tell your brain, this is important.
12. You are what you consume
Whether that be food, news, books, tweets.
13. Your perception is your reality
When you go on your phone, you’re seeing the way that a certain group of people see certain things.
14. The most important skill
The most important skill is the ability to save other people time.
15. 2+2=5
Operate in a way that requires less of everybody for the same success.
16. Streamline your life
It shouldn’t take 35 emails to go for coffee.
17. Explore your interests
Don’t read what everyone else is reading. Read what you want to read.
18. Read for exploration
Read widely. Know a little about a lot.
19. Book recommendations
How to Win Friends and Influence People — Dale Carnegie
Thinking Fast and Slow — Daniel Kahneman
The Beginning of Infinity — David Deutsch
20. Get specific
Narrow down what you want. If you’re open to everything, you might do nothing.
21. Get committed
Be willing to do the work. Nothing worthwhile happens overnight.
22. Try again
Whatever you’re doing is going to take multiple tries.
23. Be realistic
You’re more average than you think.
24. Go public
Share you work early and often. The quickest way to improve is to get feedback.
25. Be prolific
No one is perfect first time. No one is perfect. Ship often and iterate.
26. Have an outlet
Sahil spends a lot of time when not working writing science fiction.
27. Keep going
No one knows what’s going to work. No one knows how long it will take. But one day, you hit on the right formula.
28. On monetising
Develop a skill.
Build an audience.
People will soon ask to give you money.
29. Monetising methods
Make a course.
Write a book.
Teach/train/consult.
30. On mentors
The number one thing you can do if you want to make a movie: talk to someone who’s made a movie before. Want to start a podcast? Talk to someone who started a podcast. They’ll show you the holes — where not to step.
31. Train, don’t exercise
A lot of people exercise; very few people train
- Exercise = doing something for the immediate, short-term calorie burn
- Training = doing something with a goal in mind
32. On mentors (2)
Do some research — find someone you want to be like in five years and ask, “How did this person get there?”
33.Focused learning
Don’t read books and listen to podcasts without a specific goal.
34. On growth
It’s incremental learning compiled on top of each other.
35. Building in public
By sharing your work, you’re more likely to discover the biggest step you could take at any given time.
36. Content appreciation
Good content appreciates over time. Some of the best selling books were written a long time ago and sell forever.
37. Build a library of content
You want a library of content so when your time comes, people have stuff to dive into.
38. Start now
No matter what journey you are on, you have a lot to learn. The earlier you start, the better.
39. When to monetise?
Wait until your audience asks how they can pay you.
40. Everyone sucks at the beginning
Start now and get better. No one is good when they start. Check out Joe Rogan’s first podcast and look at him now.
41. Get out of your bubble
When Donald Trump became President, Sahil moved from San Francisco to one of America’s most conservative areas.
42. Debate in person
Online arguments quickly become toxic. The main reason is people are not on the same page.
43. It can’t just be better
It’s not actually their product versus your product. It’s your product versus a brand that their customers are invested in. It’s your product versus a product that they have spent dozens of hours or thousands of dollars integrating into their workflow.
44. Make it a lot better
Making something 10% better is not enough. It needs to be 10X better.
45. Markets change gradually; not at once
Windows of opportunity don’t burst open but slowly expose themselves.
46. Timing matters
Attack a problem where decisions are already being reevaluated. Don’t force change, look for it. It’s much easier to push a boulder that’s already rolling.
47. Do weekend projects
Show your passion and ability by building something over a weekend.
48. Start small
Want to make something meaningful?
Start by making tiny things that become meaningful over time.
49. There’s no substitute for doing
Reading and talking are great, but don’t let it replace doing.
50. The paradox of remote work
You can work your job from anywhere. Anyone can do your job.
51. Don’t ghost
Saying no is a skill worth learning.
52. Hard problems
To have less competition, solve harder problems.
53. Feedback
Do the work, then ask for feedback. Don’t ask for advice on your ideas.
54. Hire inexperienced people
They have the optimism of people who haven’t done it before.
55. Growth
Do things you are not qualified to do.
56. Be interesting
Don’t copy people. Follow your own interests and go deep down the rabbit hole.
57. Don’t self-reject
Never rule yourself out of something without trying, whether that be a job or reaching out to someone.
58. Be reliable
You’d be surprised how far you’ll get by doing what you say you’ll do.
59. Skills > Degree
Having the skills is what matters.
60. On education
College has never been more expensive, education has never been cheaper.
61. Don’t idolise your heroes
The people who reach the top are all people who work hard, edit excessively, and copy constantly.
62. On customers
Your customers don’t care about your product, they care about their problems.
63. Invest your time before you invest your money.
Start running before you buy running shoes. Build something before you buy the domain. Learn via YouTube before paying for a course.
64. Don’t procrastinate
It’s better to fail than procrastinate.
65. Don’t quit your job
Don’t quit your job before starting your company. Make money first.
66. On startup ideas
The best startup ideas come from the intersection of new technology and an old human need.
67. On the outside view
Innovation rarely comes from inside the industry.
68. Create value
Help people and the money will follow.
69. Minimum Viable Product
Build the necessary first, then the useful, then the nice.
70.On school
Education is about problem-solving, school is about test-passing.
71. On feedback
Only give feedback if there’s a chance it will be implemented.
72. Overcommunicate
It’s better to give someone too much information than not enough.
73. On conversion
Find people who already have the belief, don’t try to convert.
74. Energy > money
People running startups run out of energy before money.
75. Other people’s problems
Everyone’s life is harder than it looks from the outside.
76. Don’t worry
Worried about what people think about you? Don’t worry, they don’t think about you.
77. Build for yourself
If you’d buy it, then others will too.
78. Repeat customers
Repeat customers are easier to get than new customers.
79. Help people
Once you’ve helped people, you can build a business doing that.
80. Start quickly
Don’t get stuck doing research and kill the enthusiasm for the idea.
81. How to get a job
Do the work the job requires before you get it.
82. Clear mind
Share you thoughts often to keep your thoughts clear.
83. On writing
If you can’t write about something, you don’t know it.
84. Don’t procrastinate
The longer you wait, the less likely you are to do it.
85. Read then write.
Read more to write better.
86. On listening
Listen as if you are wrong.
87. Competitive advantage
Find something you like doing that others don’t.
88. On the past
Forget the past, you can’t do anything about it.
89. Customers > competition
Keep your customers happy, don’t worry about the competition.
90. On startups
Start a company to automate your job. Your first customer can be your current employer.
91. Speak now
Hard conversations get harder the longer you wait to have them.
92. Discover what you want
Start working on something and you’ll soon discover what you actually want.
93. Get the ball rolling
Once you’ve started, it’s much easier to carry on.
94. Who to work for
Find someone you want to learn from and work for them.
95. Free marketing
Exhaust free options of marketing before spending on ads.
96. On learning
Don’t learn about doing. Learn by doing.
97. On questions
Don’t ask someone a question Google could answer.
98. On compounding
Success comes slowly, then all at once.
99. Start small
Failing to write a book? Write an article. Failing to write an article? Write a Twitter thread.
100. On experience
It takes years to get to the point where it takes an hour.
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