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Notion nearly shut down twice. Once in 2015 with two weeks of cash left, once in 2022 when the product started cracking under its own growth. Here is the full story — the two years in Kyoto, the free-plan gamble that changed everything, and the one operating philosophy worth stealing.
How Tobias Lütke built Shopify in two and a half months to run a snowboard store that no longer exists — and turned the infrastructure he built for it into a platform processing $292 billion in annual transactions.
How Ben Chestnut built Mailchimp as a side project to automate his most annoying freelance work, bootstrapped it for 20 years without answering to a single investor, and sold it to Intuit for $12 billion — the largest acquisition of a bootstrapped company in history.
How Sahil Lavingia built Gumroad in 48 hours, chased the wrong game for five years, published his failure to the world before he had recovered, and rebuilt a platform that has now paid creators over $1 billion.