TLDR: Could lived experience be one of the most overlooked signals for identifying underserved markets? This piece explores why poor customer experiences often become normalized, why some problems become difficult to discuss pragmatically once they are framed primarily through morality or regulation, and whether founders who have lived inside these tensions are uniquely positioned to build differentiated solutions.
The back story
Many years ago, on a rainy late night in the East Village, I was so excited to flag an empty yellow cab passing by. When the driver got closer to me, he quickly switched off the “available” light. Astonishingly, he stopped not so far along down the road and picked up a group of four young women who I had walked out of the restaurant behind and who had been having too much of a goof time 🙂
I was initially perplexed by the unfairness and briefly contemplated escalation, but I was tired and just desperate to get home. Looking back, what strikes me isn't the unfairness itself. It's how quickly I accepted that this was simply part of living in New York. A few moments later, commotion ensued, the man was yelling profusely. One of the women had vomited in the cab and the driver’s promising night had come to an unfortunate end. The schadenfreude was quickly interrupted when one of those unmarked black cars pulled over, and the driver, a Middle Eastern gentleman, asked me where I was headed and offered me a ride. On the way, I shared my experience with him and he explained that many drivers had developed strong preferences against passengers traveling to some outer boroughs. Some passengers did not pay. Some were abusive. Some created safety concerns. And because reverse trips were often empty, these destinations carried economic risk.
None of that justified unfair treatment, and none of the narrative applied to me. But it revealed something I had not considered: the driver was not only making a judgment about me. He was making a risk calculation with incomplete information. And in fact, I was concerned for having to put my safety in the hands of some unlicensed driver. And it was in that moment that I came up with the idea for Uber.
The Philosophy
Lived experience is one of the most underappreciated sources of commercial insight. While markets are typically analyzed through data, customer research, competitive dynamics, and financial models, these approaches largely observe markets from the outside in and with a “sanitized” perspective. They often miss what can only be learned from the inside: how people experience broken systems, why they tolerate them, and where the greatest frustrations have become so normalized that they are no longer questioned. Some of these markets are especially difficult because they sit at the uncomfortable intersection of economics, incentives, identity, and morality.
As access to knowledge, technical capability, talent, and capital becomes increasingly democratized, the ability to build is becoming less scarce. Perspective is becoming more scarce. Founders with lived experience possess a form of proprietary market intelligence that cannot be easily replicated, outsourced, or acquired. They see opportunities that remain invisible to others because they have lived them, thought about them deeply, and learned from them.
Many of today's most underserved markets persist not because technology is unavailable, but because poor service, poor products, and poor outcomes have become accepted as inevitable. The founders best positioned to rewire these systems are often those who never accepted them in the first place.
Why do markets stay underserved?
One of the strangest things about markets is how quickly we normalize poor experiences. What begins as frustration gradually becomes expectation and then the norm. Eventually, entire industries are built around workarounds. The most underserved markets are often hidden in plain sight because customers, incumbents, and policymakers have all designed band-aids, jargon, and coping mechanisms to accept the status quo.
Normalization: Poor experiences have an extraordinary ability to normalize. Poor service at the neighborhood bodega becomes a food desert. Difficulty getting a yellow cab becomes a transportation policy debate. Long waits at government offices become the bureaucracy. Poor weekend train schedules become budget constraints. Over time, people stop expecting better. We stop describing these as market failures and start describing them as facts of life. When Aldi opened its doors in my neighborhood, it became immediately obvious that people hadn't stopped wanting fresh produce at lower prices, and with a pleasant shopping experience. They had simply stopped believing those things were commercially available to them where they live.
Moralization: As problems become entrenched, they also become more morally charged. We begin debating fairness, responsibility, accountability, regulation, and enforcement. These conversations are important, but they also change the nature of the problem. The objective subtly shifts from building better alternatives to improving the behavior of participants within the existing system. The challenge with moralization is that it’s often determined at some institutional level, away from the input of the people experiencing the pain.
Entrepreneurship asks a different question: What if the system itself is producing the behavior we are trying to eliminate?
Founder Constraints: Founders with real lived experience often come from the very disadvantaged backgrounds that make it harder for them to take the risk to confront the problems they know so deeply.
It’s one thing to tell a taxi driver not to discriminate because it is wrong.
It’s another to incentivize him to not discriminate or to penalize him when he does.
It’s something entirely different to redesign the system so that information and incentives are available to enable broader risk-taking and participation from current and new participants who understand the market, have better solutions and believe they can succeed economically.
That is the work of entrepreneurship.
So what exactly was I thinking about on that day?
From my experience on this rainy evening, and after I was settled in the back of the unmarked car, I started to play scenarios in my head for how all this misunderstanding with the yellow cab driver could have been avoided. Here are three:
| My lived experience | The academic / commercial lens | What we don’t talk about |
|---|---|---|---|
Information asymmetry | The taxi driver assumed I was heading somewhere undesirable because he had no way of knowing otherwise. I knew I was just going a few blocks to Murray Hill and had the means to pay, but I had no way of communicating any of that before he made his decision. | Information asymmetry increases transaction costs because both parties make decisions with incomplete information. Better transparency improves market efficiency by enabling buyers and sellers to match based on actual risk rather than assumptions. | We often think dignity means not having to reveal personal information. But in many markets, thoughtful transparency can also create dignity by replacing assumptions with information and expanding access to opportunity. |
Elimination of friction | I was desperate to show I could pay. Once I entered the unmarked car, I worried about the fare, whether I had cash, and whether this interaction would become awkward. | Friction reduces market participation by increasing the cost and uncertainty of every transaction. Eliminating unnecessary steps increases velocity, expands participation, and improves customer experience. | We often think asking people to demonstrate their ability to pay is degrading. Yet uncertainty about payment excludes many customers before the transaction even begins. The question is not whether dignity matters. It is what kind of dignity creates broader participation. and what kind of tradeoffs the underserved consumers want to make for themselves. |
Tracking and feedback | Throughout the ride home I kept wondering whether the driver was simply trying to earn an honest living or taking advantage of someone who had run out of options. The uncertainty made an otherwise ordinary trip surprisingly stressful. | Reputation systems distribute trust across millions of transactions. Identity verification and feedback reduce perceived risk, reward good participants, and allow markets to function among strangers at scale. | Privacy is deeply important. So is accountability, safety, and getting home. The uncomfortable question is whether refusing to share any information leaves strangers with no choice but to rely on instinct, assumptions, or stereotypes instead. |
The deeper lesson for me wasn't about taxis. It was about markets. When legitimate information cannot flow, markets rarely become more equitable. They become more dependent on assumptions. Sometimes those assumptions are inefficient. Sometimes they are unfair. Often they are both.
The challenge for entrepreneurs is not to ignore the moral questions this creates, but to confront them honestly. We should ask not only how to protect dignity, but also how to expand it. Not only how to preserve privacy, but how to enable participation. The best business models don't avoid these tensions, they resolve them.
What’s changed in my investment process?
Initially, this experience taught me humility. It reminded me that the problems that seem least compelling to me are often the ones I understand the least. As an investor, I became much more careful about dismissing ideas simply because they did not resonate with my own experience. Sometimes what appears to be a niche frustration is actually evidence of a market that has been hiding in plain sight.
Over time, revisiting this experience has given me some profound insight on who to back. Lived and learned experience that are well articulated and analyzed can form robust underpinnings for a truly differentiated company. Today, I increasingly see lived experience not as biography, but as competitive advantage. I spend less time asking whether a founder has found a big market, and more time asking why they see that market differently than everyone else. What I enjoy most about my work is spending time to understanding founders, their view of the world, what they have lived through, what they have learned that is unconventional; observing their body language when they talk about what grinds their gears about a problem. These founders who take things personally have incredible gumption, resilience, and persistence. They also have the authority and confidence to build in ways that are original and unconventional.
So why did I NOT found Uber?
Looking back, people often ask me, "So why didn't you start Uber?"
The answer is surprisingly simple: I had the insight, but not the capability. I didn’t know how to put it all together.
I understood the problem because I had lived it. I could even imagine elements of the solution. What I didn't understand was how technology, capital, product design, regulation, and people could come together to redesign an entire market. I saw the opportunity through the eyes of a customer, not yet through the eyes of an entrepreneur.
Today, that translation bridge between insight and capability is becoming dramatically robust. Knowledge is more accessible. AI is lowering technical barriers. Capital, talent, and distribution are more available than at any point in history. The mechanics of building are becoming increasingly democratized.
If that's true, then the scarce resource is shifting. It is becoming less about who can build, and more about who sees something worth building. Perhaps the next generation of extraordinary companies won't be built by people with the most credentials. They'll be built by people with the most original perspective.
What are the market implications?
A few of our founders' stories are now well known: Avanlee Christine and Chris Monson, Raymond and Ema Rouf, David Henderson and Ashley Sherwin, and Gerald McRobbie are examples of founders whose journeys are deeply connected to the problems they are solving. Their work is personal, but more importantly, their experiences have given them a differentiated understanding of the markets they are entering.
At the same time, we believe lived experience alone is not enough. It may reveal the opportunity, but entrepreneurship is the discipline of assembling the capabilities needed to do something about it. The next generation of great companies will be built when unique perspectives are paired with exceptional execution, technical capability, and the ability to bring ideas to market at scale.
That is why we are excited to partner with exceptional founders with proprietary market intelligence and to help them assemble the alliances, capabilities, and resources required to convert that unique insight into enduring companies.
Join our Mission
Please share this post with builders, investors, catalysts, and policy people in your networks!
If you would like to explore collaborating on this topic and partnering with Fairbridge in our work for accelerating social progress, I'd love to hear from you. And if you are a founder, you can apply for funding.
And, finally, a big thanks to Oyster, our sponsoring partner this week!
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