Playbooks

Browse all 10 business playbooks. Deep-dive strategic breakdowns and tactical executions.

Free IssueNOTION PLAYBOOK•May 10, 2026

Notion: nearly went broke twice, now everyone's second brain

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.

14 min read

Read Playbook

Free IssueTiiny Host Playbook•Feb 22, 2026

How a JP Morgan Employee Built a Web Hosting Business Nobody Thought Could Win

How Elston went from JP Morgan to 40,000+ MRR — by ignoring the giants, building for the people they forgot, and finding the one distribution channel that compounded into 20 million Google impressions.

6 min read

Read Playbook

Free IssueMailchimp Playbook•Apr 16, 2026

He Was Tired of Formatting Other People's Newsletters. So He Built the Tool. Kept the Monkey.

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.

14 min read

Read Playbook

Premium IssueGumroad Playbook•Apr 9, 2026

He Built It in a Weekend. Raised $8 Million. Lost Almost Everything. Then Built It Again.

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.

14 min read

Subscriber access required

Read Playbook

Free IssueMinecraft Playbook•Mar 6, 2026

How a Swedish Developer Built Minecraft on His Lunch Breaks

How Markus Persson wrote Minecraft alone in Java, charged for it before it was finished, and watched community become the distribution engine that made $2.5 billion possible — without a publisher, an ad, or a single paid channel.

Read Playbook

Premium IssueNomad List Playbook•Mar 19, 2026

How a Dutch Developer Built a $3 Million Solo Business From a Google Spreadsheet He Posted on X/Twitter

How Pieter Levels turned a Google Spreadsheet he posted on Twitter into a portfolio generating $3 million annually — alone, from a backpack, with a 5% hit rate, and zero employees.

Subscriber access required

Read Playbook

Free IssueTwitch Playbook•Apr 2, 2026

How a 24-Year-Old Broadcast His Entire Life on the Internet From a Camera Strapped to His Head and Built the Company That Became Twitch

How Justin Kan strapped a camera to his head, live-streamed his entire life for 24 hours a day, and accidentally built Justin.tv — the platform that became Twitch, sold to Amazon in 2014 for $970 million.

Read Playbook

Free IssueSmall Bets Playbook•Mar 12, 2026

How an Amazon Engineer Earning $500k a Year Quit and Made $310,000 From 16 Hours of Work

How Daniel Vassallo walked away from $511,000 a year, failed at his first bet, and then made $310,000 from 16 hours of work — by treating expertise as a product and transparency as his distribution channel.

Read Playbook

Premium IssueShopify Playbook•Apr 23, 2026

He Needed Software to Sell Snowboards. Every Tool He Tried Was Wrong. So He Built the Right One.

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.

14 min read

Subscriber access required

Read Playbook

Premium IssueLynda.com Playbook•Mar 26, 2026

She Went to Find a Textbook. There Was None. So She Wrote It.

How Lynda Weinman turned an empty bookshelf, a free website, and $25 a month into a $1.5 billion company — without a pitch deck, a growth hack, or a single dollar of outside capital for 18 years.

13 min read

Subscriber access required

Read Playbook