Founded Gumroad, a platform for creators to sell digital products and memberships, and ran it as CEO for 14 years until late 2025; said in February 2026 that he was working at the US Internal Revenue Service.
7 articles · 49 books they recommend
A novel of a clerk who rewrites history under a totalitarian state that watches all.
Also recommended by: Richard Branson, David Heinemeier Hansson and 3 others
A novel of a future world where people are bred in hatcheries into contented castes.
Also recommended by: Stewart Brand, Matt Mullenweg, Sam Altman and 1 other
A novel of a feudal space empire fighting over a desert planet and its spice.
Also recommended by: Patrick Collison, Stewart Brand, Andrew Chen and 7 others
A novel: a mathematician foresees an empire's fall and plans to shorten the dark age.
Also recommended by: Balaji S. Srinivasan, Adam Gazzaley and 10 others
Also recommended by: Rana el Kaliouby
Also recommended by: Bill Gates, Elon Musk
Also recommended by: Patrick Collison, Mike Maples, Jr.
Also recommended by: Richard Branson, Elon Musk, Naval Ravikant
Also recommended by: Ali Abdaal, Melinda Gates, Reese Witherspoon
A journalist learns memory techniques and wins the US Memory Championship.
Also recommended by: Bill Gates, Mohnish Pabrai, Nat Eliason and 3 others
Kahneman's synthesis of behavioral economics is the cognitive science underpinning every negotiation tactic. Anchoring, loss aversion, framing effects, and the planning fallacy — understanding why these biases operate, not just that they exist, makes you harder to exploit and more honest about your own irrationality.
Also recommended by: Andrew Wilkinson, Charles de Vaulx and 31 others
A comedian's eighteen years building a stand-up act, and why he quit it.
Also recommended by: Bill Gurley, James Altucher, Jason Calacanis and 1 other
Management as production: a manager's output is the output of the team they lead.
Also recommended by: Nat Eliason, Tim Ferriss, Andrew Chen and 23 others
Five disciplines, led by systems thinking, that let an organisation learn.
Source: Know Your Team podcast ep. 38 — interview transcript with Sahil Lavingia
Also recommended by: Mohnish Pabrai
Techniques for handling people, being liked and winning others to your view.
Also recommended by: Mohnish Pabrai, Alex and Books and 12 others
Incerto volume 4
Also recommended by: Mohnish Pabrai, Nat Eliason and 24 others
Incerto volume 5
Also recommended by: Nat Eliason, Ana Fabrega, Ben Horowitz and 11 others
Also recommended by: Bill Gates, Mark Zuckerberg
Insider account by an early PayPal marketing hire; partisan but first-hand.
Lessons from building CD Baby from a side project to an $85 million business.
Also recommended by: Nat Eliason, Ali Abdaal, Paul Jarvis and 1 other
How shared fictions such as money, nations and gods let humans cooperate at scale.
Also recommended by: Andrew Wilkinson, Bill Gates, Mohnish Pabrai and 37 others
Also recommended by: Patrick Collison, Tim Ferriss
How to rate an organisation's tribal culture on five stages and raise it.
Also recommended by: Tony Hsieh, Graham Duncan
How a mind could arise from parts, traced through Godel, Escher and Bach.
Also recommended by: Nat Eliason, Naval Ravikant, Demis Hassabis and 2 others
The politics, financing and delivery of Singapore's healthcare over five decades.
1997 forecast of digital money weakening the nation state
Also recommended by: Balaji S. Srinivasan, Nat Eliason and 10 others
Also recommended by: Patrick Collison
A physicist's stories, from fixing radios as a boy to Los Alamos and beyond.
Also recommended by: Brian Armstrong, Matt Mullenweg and 18 others
What trails, from ant paths to continental hiking routes, show about the world.
Six traits of memorable ideas, from simple and unexpected to emotional stories.
Also recommended by: Andrew Wilkinson, Mohnish Pabrai and 9 others
| DOGE Days | sahillavingia.com | |
| GOD Mode | sahillavingia.com | |
| Paying Freelancers in Equity and Dividends | sahillavingia.com | |
| No Meetings, No Deadlines, No Full-Time Employees | sahillavingia.com | |
| Reflecting on My Failure to Build a Billion-Dollar Company | sahillavingia.com | |
| Across the Border | sahillavingia.com | |
| From Bubble to Bubble | sahillavingia.com |
| The Most Interesting Teenager in Silicon Valley Paywall | Business Insider | 2012 |