Serendipity Stories bring the practice of serendipity to life in real-world examples.
The origin story of Warby Parker goes like this: Founders Dave Gilboa and Neil Blumenthal met in the MBA program at the University of Pennsylvania’s Wharton School. Both had deliberately chosen Wharton for its entrepreneurial focus, and they spent their early days there constantly discussing potential business ideas with classmates (and additional co-founders) Andrew Hunt and Jeffrey Raider.
In the summer of 2008, before starting at Wharton, fate threw Dave what turned out to be a pivotal moment: he lost his glasses while on a backpacking trip. As he recalls: "I went most of the first semester without glasses because I was shocked at the cost [to replace them]. I could buy a new phone for $200, but a pair of [designer] glasses cost $700. I started complaining to anyone who'd listen that I couldn't believe glasses were so expensive."
This personal frustration inspired the team to do some research. They soon discovered that one company, Luxottica, had a near monopoly on the eyeglass and sunglass market, and it was ripe for disruption. Prices were too high, the products weren’t great, and the customers’ shopping experience was poor.
Dave and Neil’s backgrounds had primed them for opportunity: Dave was simultaneously pursuing an MBA and a master's degree in public health, envisioning himself as the engine behind another scientist’s great idea, while Neil had worked at VisionSpring, a nonprofit that trained women in developing countries to start their own eyeglass businesses.
The connections deepened as they examined their own values. Both men had been raised with strong commitments to community service and social impact. Dave's public health studies and Neil's nonprofit background weren't just coincidences — they were crucial elements that would shape their emerging business model.
The final piece clicked when they realized they could leverage the internet not just for sales but to revolutionize the entire eyewear shopping experience. They saw how vertical integration could solve the price problem while also reinventing a poor shopping experience that had long plagued the industry.
The team moved quickly from insight to action. They developed a direct-to-consumer model that would cut out middlemen and reduce costs. They created an innovative at-home try-on program to solve the online shopping barrier. Most importantly, they developed their signature "Buy a Pair, Give a Pair" program, integrating social impact directly into their business model.
They faced significant challenges early on. Traditional retailers were skeptical of their online model, and manufacturers were hesitant to work with a startup trying to unseat the industry giant. Yet they persisted, leveraging their combined backgrounds in healthcare, nonprofit work, and business to overcome these obstacles.
Their activation of these serendipitous connections paid off. Through their willingness to seek opportunities, recognize meaningful coincidences, connect disparate ideas, and take bold action, they created a company that has fundamentally changed the eyewear industry. Warby Parker has grown into an undeniable and influential success story, demonstrating how serendipity, when properly activated, can lead to transformative business innovation.
Warby Parker’s story shows how serendipity isn't just about luck — it's about being prepared to recognize and act upon meaningful encounters. Dave, Neil, Andrew, and Jeffrey weren't just passive beneficiaries of good fortune; they were practicing serendipitists who turned chance interactions into a revolutionary business.
Your Serendipity Practice Starts Now
The Warby Parker story reveals serendipity's secret: it's not passive luck, but active preparation meeting opportunity. Dave didn't just lose his glasses—he recognized the frustration as market research. The founders didn't just have diverse backgrounds—they connected the dots between them.
Three ways to cultivate your own serendipitous breakthroughs:
Stay curious about your frustrations. That problem everyone accepts might be your billion-dollar insight waiting to be discovered.
Seek intersections. Surround yourself with diverse thinkers and experiences. Serendipity loves when different worlds collide.
Act on the sparks. When you feel that meaningful connection forming, trust it enough to explore where it leads.
Your next breakthrough might be hiding in plain sight, waiting for you to pay attention. Start practicing serendipity today—because preparation plus opportunity equals transformation.
Learn more and join us at practiceofserendipity.com