What a Horseless Carriage in Greenwich Reveals About Innovation
I recently saw a 120-year-old lesson in innovation, patience, and reinvention. Here’s what Cadillac can teach us about lasting success.
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A few weeks ago, I spent the weekend in my former hometown of Greenwich, Connecticut—a place that, like a well-restored car, reveals different layers depending on how closely you look. If you know Greenwich, you know it has a reputation. Some people adore it; others resent it. It’s often cast as the capital of hedge fund America—the setting for shows like Billions, where ambition rules and power is a contact sport. But reputations are like exteriors—they rarely tell the full story of what’s under the hood.
My kids spent their first 15 years there. It was the backdrop to our family’s formative years—a decade and a half of change, growth, and no shortage of hard choices. If I had to distill those years into one lasting insight, it wouldn’t be about wealth or success. It would be about decisions: when to hold steady, when to rebuild, and when to completely reimagine what’s possible.
That idea came full circle that weekend when my wife and I stopped by the annual Greenwich Concours d’Elegance—a high-end car show that blends history and reinvention. Ferraris, Lamborghinis, Porsches, and BMWs lined a green overlooking the Long Island Sound. Some were lovingly preserved. Others had been dramatically re-engineered. One company, for example, takes Porsche 914s and rebuilds them from the ground up—new body, new mechanicals, bespoke everything. The process takes six months and costs $500,000—after you buy the car.
You don’t go down that road lightly. Like life, it demands clarity, commitment, and a willingness to rethink everything you thought was fixed. And maybe that’s the real legacy of a place like Greenwich. It’s not just the shine on the surface, but the deeper choices that shape what we become.
Here is the thing about many of the choices that shape our lives, careers, and businesses: they don’t give us immediate feedback. You don’t know right away whether that thing you selected to study, that job you accepted, that client you pursued, or the city you moved to was a good decision. Sometimes it takes years. Even decades.
Not every strategic choice lends itself well to the rapid test-and-learn, fail-fast feedback loops that Silicon Valley espouses.
Entrepreneurs know this especially well. You pick a customer segment, a pricing model, a go-to-market strategy, and you won’t always get immediate validation. In fact, you may get misleading signals. Things that look good can go sideways. Things that seem to be failing may just need time to click.
It’s critical to know if you are operating in a short or long feedback situation.
This idea of long feedback loops came into sharp focus when I saw a 1903 Cadillac at the show. A horseless carriage. Thin tires. No roof. No doors. It looked nothing like the sleek modern SUVs and electric sedans they produce today. But that humble buggy is where Cadillac began.
Cadillac: A Story in Chapters
The Cadillac we know today—makers of luxury electric vehicles, performance sedans, and high-end SUVs—was born from an obsession with precision. In 1902, Henry Leland founded Cadillac not to build just any automobile, but to build one that was exact. Parts were interchangeable. In an era when most cars were hand-fit together and broke down often, Cadillac was betting that consistency would be a winning edge. They were betting on “modularity” which is a fascinating and big topic I’ve started exploring and plan to dive deeper into soon.
But like many bold bets on innovation, the payoff didn’t come overnight. It took years of commitment to that core idea before the world took notice.
Six years after its founding, Cadillac entered a Royal Automobile Club contest by sending them five identical disassembled cars. The 721 parts were scrambled and randomly selected for reassembly. All five automobiles came together and ran perfectly, winning Cadillac the contest and demonstrating the interchangeability of its car parts.
But think about the timeline: it was six years of believing in a standard before the market really knew how to value it.
Long Feedback Loops and Quiet Conviction
That’s the thing about the decisions that shape our lives, careers, and businesses: they sometimes come with long feedback loops. Entrepreneurs and business leaders know this especially well. You pick a customer segment, a pricing model, a go-to-market strategy, and you won’t always get immediate validation. In fact, you may get misleading signals. Things that look good can go sideways. Things that seem to be failing may just need time to click.
We are constantly tempted to switch, to pivot, to try to accelerate the feedback. However, some of the most meaningful outcomes often come when you resist that temptation.
That’s the real insight from Cadillac: enduring success requires conviction long before results show up. It requires evaluating decisions based on more than just immediate feedback.
Success is like handling a car on a dark, winding road. Yank the wheel at every shadow, and you’ll swerve into a ditch. Ignore the curves entirely, and you’ll fly off the cliff. The key is steady hands, responsive but not reactive.
Just like in business, overreacting to every challenge can derail your progress, while ignoring shifting market conditions can lead to disaster. True leadership lies in navigating uncertainty with calm focus, adjusting when necessary, but always keeping your long-term direction in sight.
But life doesn’t let you make every decision slowly. Sometimes you only get one or two shots. In those cases, you need another method: theory, faith, or history.
Use theory when logic and reasoning suggest a decision will work—when the model or idea makes sense on paper.
Use faith when you have no hard data, but a deep belief in your vision or intuition.
Use history when you can learn from others who’ve made similar choices and see how those decisions played out.
Reinvention Doesn’t Mean Abandoning the Past
What’s equally fascinating is how Cadillac has continued to evolve while staying true to its core principles. After WWII, it became the aspirational car for the American middle and upper class. Tailfins, chrome, and spacious interiors weren’t just design choices—they were status statements.
But then came the 1980s and 90s. BMW and Mercedes began redefining luxury. Cadillac lost its edge.
Here’s where many brands would fade. But Cadillac chose to reinvent. The 2000s brought the CTS line, performance sedans with sharp lines and bolder identities. And now, in 2024, Cadillac is again redefining itself with the all-electric Lyriq and the upcoming Celestiq, a bespoke EV designed to compete with the best in the world.
And yet … the soul of that 1903 horseless carriage is still there: precision, elegance, and a belief that quality will win out in the long run.
What This Means for Leaders Like Us
If you’re reading this, chances are you’re responsible for building something. A business. A product. A team. At some point, you’ve had to answer the question: Is this working?
But Cadillac teaches us that sometimes the answer isn’t visible in the short term. Some ideas don’t work quickly, but that doesn’t mean they’re failing. Looking at the 1903 Cadillac, I realized three truths for long-term success:
The best ideas take time to reveal their value. Cadillac’s commitment to precision manufacturing didn’t get broad recognition until six years in. Can your idea withstand that kind of patience?
Stay committed, but not stubborn. Cadillac didn’t just wait—it evolved. It moved from single-cylinder engines to V8s, from chrome to composite, from gasoline to electric. Staying true to your core doesn’t mean refusing to adapt.
Reinvention is a skill, not a reaction. Reinvention shouldn’t happen only when you’re desperate. Cadillac began shifting toward electrification before regulations forced the issue. Great companies anticipate change—and act early.
Innovation Isn’t a Straight Line
There’s this myth that the most successful businesses have a steady, upward trajectory. But history shows us something different. Often, it’s a jagged climb—filled with quiet years, unexpected pivots, and bets that don’t pay off right away.
Cadillac didn’t know the 1903 model would one day be a museum piece—or a centerpiece at an exclusive car show. But someone back then believed enough in the idea to keep building.
And maybe that’s the real lesson here: when we create things with care, with thought, and with a long enough view, we’re not just reacting to today’s market—we’re shaping the future.
I walked away from the Greenwich show inspired. Not by speed. Not by horsepower. But by durability. In an age where we all want the next quick win, Cadillac is a reminder that true greatness often hides behind long timelines, small details, and unglamorous persistence.
If you're working on something that’s taking longer than expected, maybe that’s not a red flag. Maybe it’s a sign you’re actually onto something important.
For more insights into long-term feedback loops, enduring brand management, and strategy adaptability, visit Outthinker.com.