The phrase “failing fast” gets thrown around a lot in the tech world, but how many of us really understand what it means? It’s not just about failing quickly—it’s about learning quickly and pivoting effectively. One of the best examples I’ve ever heard came from a conversation I had with Greg Stein almost 20 years ago in a bar in Portland. Over beers at an open-source conference, Greg shared an incredible story about his time at Ink Development Corporation. It’s a story of ambition, failure, reinvention, and (eventual) success.
The Bold Beginnings of Ink Development Corporation
Back in 1991, Greg and a group of friends founded Ink Development Corporation, dreaming of revolutionizing computing by creating applications for Microsoft’s Windows for Pen Computing platform. At the time, pen computing seemed poised to be the next big thing. Devices were being designed to enable handwriting, sketching, and other pen-based interactions—a precursor to today’s touchscreen interfaces.
The idea was bold, even futuristic: What if technology inside a pen could replace writing checks or completing forms? This was long before e-commerce or mobile computing as we know them today, but Greg and his team were convinced they were ahead of the curve.
Why the Early Pen Computing Market Failed
Despite the excitement, pen computing in the 1990s faced serious challenges:
Bulky devices: The hardware was too large and clunky for true portability.
Short battery life: The technology wasn’t yet mature enough for practical use.
High costs: Early devices were prohibitively expensive, limiting adoption.
Immature market: Critical infrastructure—like fast internet, cloud computing, and mobile connectivity—wasn’t yet in place to support widespread use.
Simply put, the world wasn’t ready for pen computing.
The Pivot to E-Commerce
Faced with limited adoption, the team at Ink Development Corporation made a tough decision in 1993: they pivoted. Renaming themselves eShop Inc., they shifted focus to the emerging world of e-commerce. It was a completely new direction, but one that proved to be transformational.
eShop became one of the first e-commerce platforms, creating software that allowed users to browse and shop online in a graphical, user-friendly interface. It leveraged the burgeoning internet in ways that were groundbreaking at the time. By 1996, eShop was acquired by Microsoft, and its technology became part of Microsoft’s early efforts in e-commerce, such as the Microsoft Merchant Server.
E-Commerce Today: The Market They Helped Shape
Looking back, that pivot to e-commerce wasn’t just a smart move—it was visionary. Consider the scale of e-commerce today:
Global sales are projected to hit $6.33 trillion in 2024.
E-commerce accounts for 20.1% of total retail sales globally.
2.71 billion people—about a third of the world’s population—shop online today.
It’s incredible to think that this massive industry partially owes its roots to a failed experiment in pen computing.
The Ink Alumni: From Failure to World-Changing Success
So, what happened to the Ink team? Well, here’s where the story gets really interesting. Greg—my friend who shared this tale over beers in Portland—went on to become one of the most influential open-source engineers in the world. He chaired the Apache Software Foundation, was a key figure in the Python programming language, and helped launch Google’s open-source programming platform. Total genius.
But here’s the real twist. One of Greg’s co-founders at eShop, Pierre, didn’t stop with their pivot into e-commerce. After Microsoft acquired eShop in 1996, Pierre kept thinking about how e-commerce could evolve. He was less interested in business-to-consumer and more interested in consumer-to-consumer. So in 1995, he started tinkering with the idea of people buying and selling things directly to one another. He coded up a little platform called AuctionWeb—sound familiar? That platform would later become eBay. By 1997, eBay had taken off, and by 1998, it went public. Today, Pierre Omidyar is worth over $10 billion and one of the world's richest people.
The Bezos Perspective: Long-Term Thinking
Jeff Bezos once said, “If everything you do needs to work on a three-year time horizon, then you’re competing against a lot of people. But if you’re willing to invest on a seven-year time horizon, you’re now competing against a fraction of those people.”
The story of Ink Development Corporation perfectly illustrates this. They were too early with their original vision, and they were wrong about pen computing. But that failure allowed them to be pioneers in e-commerce, a market that would forever change how we live, shop, and connect.
A Night in Portland: Reflecting on Failing Fast
That night in Portland, as Greg shared this story over beers, it struck me how much innovation depends on timing, perseverance, and the ability to pivot. Ink Development Corporation didn’t succeed with its original vision, but its willingness to fail fast and adapt led it straight into the heart of a revolution.
So, the next time someone tells you about “failing fast,” think of Greg, Pierre, and the Ink team. It’s not just about failing—it’s about learning. Sometimes, the wrong idea at the right time can lead you to something far bigger than you ever imagined.
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