Pin Drop
Pin Drop began as a simple idea—a personal solution to a problem—that evolved into a transformative app, connecting people and businesses to the places that matter most. Originally launched as a portfolio project, it quickly gained global recognition, resonating with users who wanted a way to personalise and privately manage their locations.
The journey of Pin Drop has been one of both triumph and adversity. From early success and industry accolades to challenges that nearly ended its run, the app’s evolution is a testament to perseverance and creativity. After years of dormancy, it was revived with fresh purpose and has since grown into a powerful tool for collaboration and location management.
More than just an app, Pin Drop’s story is one of resilience and innovation, demonstrating the impact of solving meaningful problems in ways that truly matter.
How It All Started
Pin Drop began life as a portfolio project for my agency at the time, Caffeinehit. We were a small team of three, working out of an arch behind Cargo nightclub in Shoreditch. Back then, I had a clunky old Nokia phone and couldn’t fully grasp the potential of this new device from Apple. When Apple announced the App Store, which would allow businesses to build and distribute something called an ‘app’ to anyone with an iPhone, it seemed like an absolute no-brainer. But where to start? How do you even design for these things? There was practically no documentation, and Photoshop was the only design software available.
In January 2011, Tom joined the Caffeinehit crew, making us a trio and kickstarting our efforts to build some of the app ideas we’d been dreaming up—ideas I hoped would open up new business opportunities for us. I decided to invest in an iPhone (which I’m pretty sure I still have somewhere) and started experimenting with apps for my own use. One day, while using Apple Maps—powered by Google Maps at the time—I discovered its “Drop a Pin” feature. For someone with an appalling memory for places, this felt revolutionary.
I began dropping pins to save places I wanted to remember, but when I returned to check one of them a few days later, I realised something frustrating: the simple labels or names you could add to a location would overwrite the previous one. You could only ever have one pin. It could only have a name. There was no way to add notes or any personal information, and, crucially, no way to record anything privately. At the time, Foursquare and Gowalla allowed users to ‘check in’ to locations, but neither offered much personalisation, let alone the option to keep your information private.
And so, the idea for Pin Drop was born (and no, the name had nothing to do with the text on Apple Maps’ button!). Over the next few months, we designed and built the app, and Pin Drop launched on the App Store in April 2011. I decided to charge £1.99 for it—a steep price for apps back then, but the intention was more about showcasing our work and helping me stop forgetting places, rather than aiming for mass adoption.
A few months later, I made the decision to release it for free, and that’s when everything changed. Things. Went. Crazy! Within hours, the app was trending in the App Store and climbing the charts—not just in the Travel and Navigation categories, but across the entire store. It was unbelievable. The app found a particularly warm reception in Italy, Germany, and the UK, where users embraced it enthusiastically. It turned out I wasn’t the only one searching for a way to remember the world around me. Pin Drop had struck a chord.
The Rise and Fall
Over the next two years, Pin Drop gradually evolved into its own little world. Between client projects, we dedicated time to keep the app updated and running smoothly. The app began to gain traction, attracting press coverage and a steady stream of inbound work for clients like KFH, Alison Jackson, Mr & Mrs Smith, Top10, WIWT, and eventually, a project called Summly.
Summly was one of those projects that, in hindsight, tested every limit—nearly breaking both our spirits and the business itself. Over three to four gruelling months, our team built the app and backend infrastructure for Nick D’Aloisio’s ambitious startup. When the app launched, it shot to the top of the charts, featured globally, and gained the backing of prominent figures of the time, including Stephen Fry. That project introduced me to Stephen, who, after a number of conversations, offered to connect me with Jony Ive and Eddie Cue ahead of my first trip to California in 2013.
A few days before I travelled, Stephen made the introduction, and despite it being the launch week for iOS 7, Jony made time to meet. Sitting with him 1:1, sharing what we’d built and our vision for Pin Drop, was both inspiring and humbling. It also taught me a valuable lesson: never demo with flat PNGs when presenting to someone like Jony Ive!
After wrapping up Summly, we locked down the team and reimagined Pin Drop from the ground up, with plans to relaunch in November 2013. Launch day arrived, and I was up early, eagerly anticipating glowing reviews. Instead, I woke to a flood of one-star ratings. Those hours, waiting for the team to arrive at the office, were the longest of my life. We discovered that the app, featured globally by Apple that day, was crashing due to an issue with Facebook login. Later, Apple called to say they’d have to pull the UK feature to stem the tide of negative reviews. I was devastated.
Weeks later, Facebook invited us to their London office. They admitted that the crashes were caused by a bug in their SDK—something they never officially acknowledged but told us in person. While it explained the situation, it didn’t undo the damage or help us regain the momentum we had lost. As it turned out, Facebook had been considering acquiring us at the time, something I only learned years later in 2022.
Despite these struggles, Pin Drop was recognised as one of the world’s top apps by The Sunday Times in the UK and featured in Apple’s “Best of 2013.” Encouraged by this, I made the bold decision in 2014 to shut down the agency side of the business and focus solely on Pin Drop. We raised funding, hired a team, and were finally making progress towards monetising the platform. But six months later, as our runway ran out, promised follow-on funding fell through, forcing me to make the hardest decision of my career: closing the company.
I still vividly remember walking back to the office to let the team know. We had enough funds to pay everyone until the end of the month. They were given a choice: leave immediately to find new jobs or stay for two weeks to help make Pin Drop work offline, allowing the app to live on. All but two chose to stay. On our final day together, the team even bought me a bottle of champagne to say thank you—despite the fact they were the ones losing their jobs.
Before shutting the doors for the last time, I made a promise to support every remaining member of the team in their future endeavours. As a last throw of the dice, I emailed Apple, Google, and Facebook, saying, “hire us or buy us.” Apple responded, flying executives from China and California to London to meet us. By the end of the day, we were all Apple employees, working on Apple Maps.
While the team moved on to new challenges, it was time for Pin Drop to find its own way, quietly waiting for its next chapter.
The Rebirth
It was Christmas Eve when I found myself in a chilly North London solicitor’s office, closing down Caffeinehit with the liquidators. At the time, I had no idea what would come next. In the midst of this difficult chapter, I confided in a dear friend (PG) about the liquidation and suggested he might want to contact the liquidators about Pin Drop’s assets. To my surprise, he did—and he ended up acquiring everything related to Pin Drop. He assured me that whenever I was ready to bring it back to life, all I had to do was let him know.
For nearly seven years, Pin Drop sat in the App Store, untouched and gathering dust. By early 2020, I was ready to leave Meta, and Pin Drop was calling me back. Remarkably, no one else had pursued what we had originally identified as a way to monetise the app. Excited to restart the journey, I began meeting with VCs, but within three months, COVID hit. With a global pandemic raging and my second child on the way, it became clear that diving headfirst into a startup wasn’t the best idea at the time.
It wasn’t until a year later, after countless lockdowns, that an old friend reached out, looking for a side project to inspire him. We had always enjoyed working together during our agency days, and I jumped at the chance to collaborate on Pin Drop. On 9th March 2021—symbolically almost 10 years to the day since its first launch—we had our first kick-off call to discuss the project.
Reviving Pin Drop wasn’t easy. Dusting off the old code revealed an app that was one OS release away from breaking entirely. After six months of painstaking updates, we finally relaunched the app. Amazingly, as far as we know, no one lost their data during the transition. The feeling of being back was incredible.
For the next year, the two of us worked on Pin Drop in our spare time alongside our day jobs. Each release brought improvements and greater stability, even if there were plenty of bugs along the way. That’s part of the process when you’re shipping quickly as a team of two part-timers.
Now, in 2024, nearly 14 years since its original launch, Pin Drop is stronger than ever. We’ve finally begun monetising the app, and the strategies we identified all those years ago resonate more strongly today than ever. Companies around the world now use Pin Drop every day to collaborate with their teams and streamline the way they work with locations. Red Bull F1 used Pin Drop to manage a road race across California and Nevada, while Lupine Races tracked participants across Europe.
Even after all this time, it feels like we’re only scratching the surface of what Pin Drop can do. As we continue to grow globally, I’m more excited than ever to see what the future holds for the app—and the community it continues to inspire.