Details behind 30+ pivots, including how they knew it was time to pivot, how long it took them to pivot, and much more
From
The art of the pivot, part 1: The definitive list of successful pivots
Details behind 30+ pivots, including how they knew it was time to pivot, how long it took them to pivot, and much more
www.lennysnewsletter.com

Name | Current idea | How they found the new idea | Reason for pivot | Original idea |
|---|---|---|---|---|
Twitter | Social network | Internal hackathon: Jack Dorsey built a prototype at a hackathon; founders got excited about it. | Realized it was a bad idea after Apple launched a competitor | A podcasting company called Odeo, allowing users to create, record, and share podcasts online |
Lyft | On-demand ridesharing | Internal hackathon: Team built a prototype at a hackathon; founders got excited about it. | Growth plateaued | Peer-to-peer carpooling service called Zimride |
Loom | Video messaging and screen recording tool | Noticed one feature showing pull: Noticed one element of the product (video recording) that people were using and loving, and went all in. | Low retention | A subject-matter-expert marketplace |
Lattice | Performance management platform | Noticed an adjacent idea showing pull: HR leaders founder was talking to were all looking for a better performance management solution. | Low retention | OKR software |
Flickr | Online photo-sharing platform | Noticed one feature showing pull: Users were using and loving one feature of the game. | Growth plateaued | An online role-playing game called "Game Neverending" |
Sprig | User feedback platform | Noticed pull for internal tool: A internal survey tool they built for themselves was getting a lot of interest from other founders. | Lukewarm interest | A way to organize cloud files collaboratively |
Zip | Procurement SaaS platform | Following the pain: Nonstop ideation, prototyping, and talking to people in founder’s network looking for pain. | Saw a bigger market opportunity | Tried 5-6 ideas, including an accountant hiring marketplace |
WhatNot | Life video shopping | ? | Lukewarm interest | Auctions for Funko Pops |
Netflix | Online video-streaming service | Working backward from the future. | Market shifted to online streaming | DVD-by-mail service |
Headspace | Meditation app | Doing it manually, and seeing the need and opportunity to productize it. | Wanted to make their work more scalable | Meditation event business in London |
Uber | On-demand car | Lyft launched ridesharing. | Saw a bigger market opportunity | On-demand limo |
YouTube | Online video platform | Exploring an interesting piece of internal tech: Realized there wasn't value in the problem space (video dating), but the tech they built could be generalized. | Lukewarm interest | Dating site where people upload videos of themselves talking about the partner of their dreams |
Yelp | Online reviews of local businesses | Noticed one feature showing pull: Noticed people using the product in a surprising way (leaving reviews on their own), and went all in. | Lukewarm interest | Tool to automate emailing friends for recommendations |
WhatsApp | Messaging app | Exploring an interesting piece of tech: When Apple launched push notifications, founder explored it for sharing status more proactively | Lukewarm interest | App for showing statuses of your friends |
Vanta | Automated security and compliance | Following the pain: Nonstop ideation, prototyping, and talking to people in founder's network looking for pain. | Lukewarm interest | B2B Alexa |
Twitch | Live streaming platform for games | Noticed one market showing pull: Noticed a small % of users streaming games on the platform; founders got excited about it and doubled down. | Growth plateaued | A Big Brother-style show called Justin.tv streaming Justin Kan's life 24/7 |
Slack | Online enterprise communication platform | Noticed their internal tool showing pull: Realized employees loved using this one chat feature they built, and went all in. | Realized it wasn't ever going to become a big business | Massively multiplayer online game called Glitch |
Shopify | E-commerce platform | Noticed their internal tool showing pull: Their e-commerce infrastructure was seeing a lot of interest from other sellers. | Realized there's much bigger opportunity selling software | An online store for selling snowboards called Snowdevil |
Retool | No-code internal tool builder | Brainstorming and tinkering: Thinking about their past unique experience and problem they’ve run into personally. | Low retention | Venmo for the U.K. called Cashew |
Segment | Customer data platform | Exploring an interesting piece of internal tech: Co-founder spent weekend building out one piece of tech he thought was interesting; launched it and saw immediate interest. | Little to no interest | University classroom lecture tool |
Pinterest | Social platform to discover, save, and share visual content | Noticed one feature showing pull: Noticed one element of the product (collecting images) that people were using and loving, and went all in. | Low retention | Digital retail catalogs app called Tote |
Plaid | Financial services APIs | Exploring an interesting piece of internal tech: A customer (Venmo) asked about licensing their backend infrastructure. | Low retention | Tried 5-6 ideas, including an app that recommends ways to could spend less money |
PayPal | Online payments | Brainstorming and tinkering: Nonstop ideation and exploration looking for big opportunities. | Realized it was a bad idea | Encyption for handheld devices called Fieldlink, then beaming money between PalmPilots |
Notion | All-in-one productivity and collaboration platform | Noticed one feature showing pull: Noticed one element of the product (editor + collaboration) that people were using and loving, and went all in. | Low retention | No-code app/website builder, Webflow meets Figma |
Okta | Cloud identity management | Noticed one feature showing pull: Talked to 100 people and they kept asking about identity. | Lukewarm interest | Reliability monitoring and reporting tool for cloud services called SaaSure |
Instagram | Social photo-sharing app | Noticed one feature showing pull: Users were using and loving one element of the product (photo sharing). | Low retention | Location check-in app called Burbn |
Hugging Face | Collaborative hub for developing and sharing open-source machine learning models | Exploring an interesting piece of internal tech: Co-founder spent weekend building out a piece of tech he thought was interesting; launched it and saw immediate interest. | Lukewarm interest | AI Tamagotchi |
Coinbase | Cryptocurrency exchange platform | Noticed an adjacent idea showing pull: Talked to users churning asking if they'd use it if they could buy Bitcoin, and they all said yes, so they built it. | Low retention | Hosted Bitcoin wallet |
Discord | A group messaging app that integrates video, voice, and text | Exploring an interesting piece of internal tech: An engineer suggested building out one piece of tech he thought was interesting. | Realized it wasn't ever going to become a big business | A mobile multiplayer game called "Fates Forever" |
Box | Enterprise cloud-based content management platform | Noticed bigger market showing pull: They realized the business opportunity was much bigger if they pivot to the enterprise. | Realized there's much bigger opportunity in B2B | A consumer cloud-based file storage and sharing service called Box.net |
Brex | Business credit card | Brainstorming and tinkering: Thinking about their past unique experience, and problem they've run into personally. | Realized it was a bad idea | A virtual reality headset called Veyond |
Amplitude | Analytics platform | Noticed pull for internal tool: A internal analytics tool they built for themselves was getting a lot of interest from other founders. | Low retention | A hands-free texting app called Sonalight |