Introduction Remember drugstore.com? That blue-and-white website where you could order everything from vitamins to makeup to cold medicine? It was one of the internet’s first big online pharmacies. Then, one day in 2016, it simply vanished from our screens. Poof! Gone. As someone who has
Introduction Remember when everyone thought crowdsourcing would change how we make things forever? I sure do. Back in 2009, a bright-eyed 24-year-old named Ben Kaufman launched Quirky with a simple but powerful idea: let regular folks submit their invention ideas, then have a community vote
The sudden collapse of Defy Media in 2018 sent shockwaves through the digital entertainment industry. What began as one of the most promising digital media companies quickly unraveled, leaving creators scrambling and millions of fans wondering what happened to their favorite content. As someone who’s
Beepi burst onto the scene with a bold vision: to revolutionize how we buy and sell used cars. As someone who watched this startup rocket to a $560 million valuation before crashing spectacularly, I’ve got some insights to share. The story of Beepi isn’t just
Introduction Remember Rdio? If you don’t, you’re not alone. Once a bright star in the streaming music galaxy, Rdio blazed a trail that others would follow before burning out too soon. As someone who rode the startup rollercoaster and now funds the next generation of
Introduction Remember Anki? That flashcard app everyone swore would revolutionize learning? The one medical students, language learners, and knowledge workers praised as the ultimate memory hack? Well, despite its cult following, Anki never truly broke into the mainstream. It remained stuck in a niche, failing
Introduction Have you ever watched a sandcastle wash away with the tide? One minute it’s there—magnificent, bold, ambitious—and the next, it’s gone. That’s what happened with Katerra, once valued at $4 billion. Katerra’s story is a cautionary tale about big dreams, bigger funding, and the
The story of Airlift’s rise and fall contains valuable lessons for entrepreneurs everywhere. As someone who’s built startups and now invests in them, I find Airlift’s journey particularly fascinating – a rocket ship that soared high before crashing back to earth. Introduction: Pakistan’s Shooting Star
Introduction Remember when getting your home cleaned was just a few clicks away? That was the promise of Homejoy. As someone who rode the startup rollercoaster myself before becoming an angel investor, Homejoy’s story hits close to home. This once-shining star raised $40 million, expanded
Introduction Remember when Google announced Stadia in 2019? The tech world buzzed with excitement. Cloud gaming seemed like the future—play anywhere, on any device, without expensive hardware. As someone who’s launched startups and now invests in them, I watched Stadia with particular interest. Here was
The story of Quiznos is fascinating – a once-thriving sandwich chain that pioneered toasted subs but ultimately crumbled under the weight of its own business model. As someone who’s been a part of the startup ecosystem for a long time, I’ve watched this saga unfold
Social media has transformed how we communicate and share information. Apps like Facebook, Twitter, and Instagram have become household names. However, some platforms have struggled to find lasting success. One such app was Yik Yak, an anonymous social media platform that allowed users to post
Once upon a time, there was a shiny new startup called PepperTap. It promised to revolutionize grocery delivery in India. With big dreams and even bigger funds, it burst onto the scene ready to take a bite out of the market. But alas, things didn’t
The Concorde was a technological marvel. This supersonic passenger jet could fly at over twice the speed of sound. It made the journey from New York to London in just three and a half hours! Pretty amazing, right? However, despite its amazing capabilities, the Concorde
Today, we’re going to do a deep dive into the curious case of Vine – the pioneering short-video app that took the world by storm, only to wither away almost as quickly as it arrived. Why did such a wildly popular app with a rabidly
Today we’re going to explore one of the most fascinating business puzzles of the modern era – why did YouTube become an absolute juggernaut in online video, while competitors like Vimeo languished in its shadow? As an entrepreneur and early investor in tech companies, I’ve
Frontrow was an ed-tech startup that offered live online classes for hobbies and extracurricular learning. It raised over $17 million from top Silicon Valley investors like Lightspeed Venture Partners and Elevation Capital. Yet, Frontrow shut down operations in 2023 after a four-year journey. Why did
Shyp was a pioneer in the on-demand shipping industry. It offered convenient pickup and delivery services for customers who needed to ship items. Despite its promising start and innovative business model, Shyp ultimately failed and shut down operations in 2018. This post will delve into
Failure sucks, doesn’t it? I mean, who actually wants to fail at something? Nobody starts a company thinking “Gee, I really hope this whole thing crashes and burns.” But sadly, most startups do fail. And when that happens, founders are left picking up the pieces.