Failure is not the opposite of success, it is a stepping stone to achieving it. For many startups, the journey to success is paved with setbacks, false starts, and dramatic turns. Yet, some of the most iconic companies we know today did not achieve success by sticking to their original plans. Instead, they embraced failure, pivoted, and found a new path forward.
Here are six startups that, when faced with failure, redefined their vision, adapted, and ultimately turned their struggles into remarkable comebacks.
Slack
Before becoming the leading workplace communication tool, Slack began as an internal messaging platform developed within Stewart Butterfield’s company, Tiny Speck, during the development of their online video game, Glitch. Despite initial excitement, the creators discovered that the game was costly and difficult to manage. Consequently, in 2011, Glitch was temporarily “unlaunched” to enhance its core features. However, the following year, the game was permanently discontinued. During the game’s development, the team had developed an internal communication tool to coordinate their work. Realising that their communication tool had greater potential than the game itself, they pivoted away from gaming and launched Slack,derived from the phrase “Searchable Log of All Conversation and Knowledge” as a workplace messaging app in 2013. Fast forward to today, and Slack is one of the most popular business tools, used by millions of people worldwide.
Pinterest started as a mobile app called Tote, developed by Ben Silbermann and Paul Sciarra. Tote was designed to replace paper catalogues, allowing users to browse products and make purchases on the go. However, the app struggled, largely due to the limitations of mobile payment technology at the time. Users found it difficult to make purchases, but they were actively collecting and sharing their favourite products with others. Recognizing this emerging behaviour, Silbermann and his team shifted gears. Instead of focusing on mobile shopping, they pivoted toward creating Pinterest—a platform where users could curate and share collections of things they loved. Development of Pinterest began in December 2009, and by March 2010, the site launched as a closed beta. Despite a slow start, within nine months Pinterest had 10,000 users, thanks in part to Silbermann’s hands-on approach of personally reaching out to the first 5,000 users.Today, Pinterest remains a major player in visual search and online discovery, with millions of users worldwide collecting and sharing everything from home decor to recipes.
PayPal
PayPal’s journey began in December 1998 when Max Levchin, Peter Thiel, and Luke Nosek founded the company as Fieldlink, initially focusing on developing security software for handheld devices. The goal was to create robust cryptography technology to safeguard personal data. However, the concept did not resonate with customers, leading the founders to reconsider their business strategy. Recognizing the growing demand for digital financial solutions, the company shifted its focus to creating a digital wallet. In 1999, they launched the first version of the PayPal electronic payment system, allowing users to send money online easily and securely. This pivot proved to be a game-changer. The popularity of the digital wallet surpassed all expectations, prompting the company to abandon its original security software model entirely. As a result, PayPal quickly evolved into a leading global payment platform, facilitating transactions for millions of users around the world and reshaping the way people handle money online.
X (Twitter)
Twitter originated from a podcasting venture called Odeo, which was founded in 2004 by Evan Williams, Biz Stone, and Noah Glass. Williams and Stone, who previously worked at Google, had developed the popular blogging platform Blogger. However, Odeo faced a significant challenge in 2005 when Apple announced that it would integrate podcasts into iTunes, effectively overshadowing Odeo’s efforts in the podcasting space. Realising the futility of competing with a tech giant like Apple, the Odeo leadership sought a new direction. They invited employees to share any intriguing side projects, and engineer Jack Dorsey proposed a short messaging service (SMS) that would allow users to share brief, blog-like updates with their friends. Inspired by this idea, Glass suggested the name “Twttr,” and on March 21, 2006, Dorsey sent the first message, famously stating, “just setting up my twttr.” The fully realised version of Twitter was launched in July 2006. Seeing the potential of this new product, Williams, Stone, and Dorsey acquired Odeo and established Obvious Corp. in October 2006 to further develop Twitter. Interest in the platform surged following its presentation at the South by Southwest (SXSW) music and technology conference in Austin, Texas, in March 2007. This exposure led to significant venture capital investment and the creation of Twitter, Inc. as a corporate entity in April 2007, with Dorsey serving as its first CEO.
YouTube
When YouTube made its debut in 2005, it had a unique mission: to serve as a video-dating platform where users could upload videos introducing themselves to potential romantic partners. Co-founder Steve Chen shared at the 2016 South by Southwest (SXSW) conference that the idea was encapsulated in their slogan, “Tune in, Hook up.” The founders believed video would be a perfect medium for dating, yet users had other plans. As they observed user behaviour, it became clear that the dating aspect was not resonating with the audience. Instead, people were sharing a diverse range of content, from humorous clips to how-to tutorials. Realising that their original vision was misguided, Chen and his team decided to pivot away from dating, embracing a broader scope for content creation. In a desperate bid to attract dating videos, the founders even offered incentives, like $20 to women who would upload self-introductions. This effort went largely unreciprocated, leading to the conclusion that it was time to open the platform up to any video. The first official video, titled “Me At The Zoo,” featuring co-founder Jawed Karim at the San Diego Zoo, marked a new beginning for the platform. Within a year, YouTube became one of the internet’s most visited sites, transforming into a hub for diverse user-generated content.
Instagram was not always the photography sensation it is today. It began as Burbn, a check-in app created by Stanford graduate Kevin Systrom, who had previously worked at Google. The app, named after Systrom’s love for whiskey and bourbon, aimed to combine location-sharing features with photo uploads, inspired by the success of platforms like Foursquare. However, Burbn was cluttered with too many features, and users were primarily interested in the photo-sharing aspect. To streamline the app, Systrom partnered with fellow Stanford graduate Mike Krieger, who had experience with the social media platform Meebo. They decided to focus exclusively on mobile photography, renaming the app Instagram. In just a few months, they designed a simple interface that emphasised image sharing, comments, and the ability to add filters. Choosing to launch on iOS to capitalise on the iPhone 4’s superior camera, Instagram went live on October 6, 2010. The app quickly established a foothold, amassing 25,000 users on its first day and hitting one million users within three months.
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