Blind to Disruption – The CEOs Who Missed the Future

How did you go bankrupt?”
Two ways. Gradually, then suddenly.”
Ernest Hemingway, The Sun Also Rises

Every disruptive technology since the fire and the wheel have forced leaders to adapt or die. This post tells the story of what happened when 4,000 companies faced a disruptive technology and why only one survived.


In the early 20th century, the United States was home to more than 4,000 carriage and wagon manufacturers. They were the backbone of mobility and the precursors of automobiles, used for personal transportation, goods delivery, military logistics, public transit, and more. These companies employed tens of thousands of workers and formed the heart of an ecosystem of blacksmiths, wheelwrights, saddle makers, stables, and feed suppliers.

And within two decades, they were gone. Only 1 company out of 4,000 carriage and wagon makers pivoted to automobiles.

Today, this story feels uncannily familiar. Just as the carriage industry watched the automobile evolve from curiosity to dominance, modern companies in SaaS, media, software, logistics, defense and education are watching AI emerge from novelty into existential threat.

A Comfortable Industry Misses the Turn
In 1900, the U.S. was the global leader in building carriages. South Bend, IN; Flint, MI; and Cincinnati, Ohio, were full of factories producing carriages, buggies, and wagons. On the high-end these companies made beautifully crafted vehicles, largely from wood and leather, hand-built by artisans. Others were more basic wagons for hauling goods.

When early automobiles began appearing in the 1890’s — first steam-powered, then electric, then gasoline –most carriage and wagon makers dismissed them. Why wouldn’t they? The first cars were:

  • Loud and unreliable
  • Expensive and hard to repair
  • Starved for fuel in a world with no gas stations
  • Unsuitable for the dirt roads of rural America

Early autos were worse on most key dimensions that mattered to customers. Clayton Christensen’s “Innovator’s Dilemma” described this perfectly – disruption begins with inferior products that incumbents don’t take seriously. But beneath that dismissiveness was something deeper: identity and hubris. Carriage manufacturers saw themselves not as transportation companies, but as craftsmen of elegant, horse-drawn vehicles. Cars weren’t an evolution—they were heresy. And so, they waited. And watched. And went out of business slowly and then all of a sudden.

Early Autos Were Niche and Experimental  (1890s–1905) The first cars (steam, electric, and early gas) were expensive, unreliable, and slow. They were built by 19th century mechanical nerds. And the few that were sold were considered toys for other nerds and the rich. (Carl Benz patented the first internal combustion engine in 1886. In 1893 Frank  Duryea drove the first car  in the U.S.)

These early cars coexisted with a massive horse-powered economy. Horses pulled wagons, delivered goods, powered streetcars, and people. The first automakers used the only design they knew: the carriage. Drivers sat up high like they did in a carriage when they had to see over the horses.

For the first 15 years carriage makers, teamsters, and stable owners saw no immediate threat. Like AI today: autos were powerful, new, buggy, unreliable and not yet mainstream.

 Disruption Begins (1905–1910) 10 years after their first appearance, gasoline cars became more practical, they had better engines, rubber tires, and municipalities had begun to pave roads. From 1903 to 1908 Ford shipped 9 different models of cars as they experimented with what we would call today minimum viable products. Ford (and General Motors) broke away from their carriage legacies and began designing cars from first principles, optimized for speed, safety, mass production, and modern materials. That’s the moment the car became its own species. Until then, it was still mostly a carriage with a motor. Urban elites switched from carriages to autos for status and speed, and taxis, delivery fleets, and wealthy commuters adopted cars in major cities.

Even with evidence staring them in the face, carriage companies still did not pivot, assuming cars were a fad. For carriage companies this was the “denial and drift” phase of disruption.

The Tipping Point: Ford’s Model T and Mass Production (1908–1925) The Ford Model T introduced in 1908 was affordable ($825 to as little as $260 by the 1920s), durable and easy to repair, and made using assembly line mass production. Within 15 years tens of millions of Americans owned cars. Horse-related businesses — not only the carriage makers, but the entire ecosystem of blacksmiths, stables, and feed suppliers — began collapsing. Cities banned horses from downtown areas due to waste, disease, and congestion.  This was like the arrival of Google, the iPhone or ChatGPT: a phase shift.     

Collapse of the Old Ecosystem (1920s–1930s) Between 1900 and 1930 U.S. horse population fell from 21 million to 10 million and the carriage and buggy production plummeted. New infrastructure—roads, gas stations, driver licensing, traffic laws—was built around the car, not the horse.

Early automakers borrowed heavily from carriage design (1885–1910). Cars emerged in a world dominated by horse-drawn vehicles and they inherited the materials and mechanical designs from the coach builders.

– Leaf springs were the dominant suspension in 19th-century carriages. Early cars used the same.
– There were no shock absorbers in carriages, and early autos. They both relied on leaf spring damping, making them bouncy and unstable at speed. Why? Roads were terrible. Speeds were low. Coachbuilders understood how to make wagons survive cobblestones and dirt.
– Carriages used solid steel or wooden axles; early cars did the same.

Body Construction and Design Borrowed from Carriages
– Car bodies were wood framed with steel or aluminum sheathing, like a carriage.
– Upholstery, leatherwork, and ornamentation were also carried over.
– Terms like roadster, phaeton, landaulet, and brougham are directly inherited from carriage types.
– High seating and narrow track: Early cars had tall wheels and high ground clearance, like buggies and carriages, since early roads were rutted and muddy.

Result: Early automobiles looked like carriages without the horse, because they were, functionally and structurally, carriages with engines bolted on.

What Changed Over Time
As speeds increased and roads improved, wood carriage design couldn’t handle the torsional stress of faster, heavier cars. Leaf-spring suspensions were too crude for speed and handling. Car builders began using pressed steel bodies (Fisher Body’s breakthrough), independent front suspension (introduced in the 1930s), finally integrating the car body and chassis into a single, unified structure, rather than having a separate body and frame (in the 1930s–40s). 

Studebaker: From Horses to Horsepower
The one carriage maker who did not go out of business and became an automobile company was Studebaker. Founded in 1852 in South Bend, IN, Studebaker began by building wagons for farmers and pioneers heading west. They supplied wagons to the Union Army during the Civil War and became the largest wagon manufacturer in the world by the late 19th century. But unlike its peers, Studebaker made a series of early, strategic bets on the future.

In 1902, they began producing electric vehicles—a cautious but forward-thinking move. Two years later, in 1904, they entered the gasoline car business, at first by contracting out the engine and chassis. Eventually, they began making the entire car themselves.

Studebaker understood two things the other 4,000 carriage companies ignored:

  1. The future wouldn’t be horse-drawn.
  2. The company’s core capability wasn’t in carriages—it was in mobility.

Studebaker made the painful shift in manufacturing, retooled their factories, and retrained their workforce. By the 1910s, they were a full-fledged car company.

Studebaker survived long into the auto age—longer than most of the early automakers—and only stopped making cars in 1966.

Fisher Body: A Coach Builder for the Machine Age
While Studebaker made a direct pivot of their entire company from carriage to cars, a case can be made that Fisher Body was a spinoff. Founded in 1908 in Detroit by brothers Fred and Charles Fisher, the Fishers had worked at a carriage firm before starting their own auto-body business.  They specialized in producing the car bodies, not an entire car. Their key innovation was making closed steel car bodies which was a major improvement over open carriages and wood frames. By 1919, Fisher was so successful that General Motors bought a controlling stake and in 1926, GM acquired them entirely. For decades, “Body by Fisher” was stamped into millions of GM cars.

Durant-Dort: The Origin of General Motors
While the Durant-Dort Carriage Company never made cars itself, its co-founder William C. (Billy) Durant saw what others didn’t.  See the blog posts on Durant’s adventures here and here.

Durant used the fortune he made in carriages to invest in the burgeoning auto industry. He founded Buick in 1904 and in 1908 set up General Motors. Acting like one of Silicon Valley’s crazy entrepreneurs, he rapidly acquired Oldsmobile, Cadillac, and 11 other car companies and 10 parts/accessory companies, creating the first auto conglomerate. (In 1910 Durant would be fired by his board. Undeterred, Durant founded Chevrolet, took it public and in 1916 did a hostile takeover of GM and fired the board. He got thrown out again by his new board in 1920 and died penniless managing a bowling alley.)

While his financial overreach eventually cost him control of GM, his vision reshaped American manufacturing. General Motors became the largest car company in the 20th century.

Why the Other 3,999 Carriage makers Didn’t Make It
Most carriage makers didn’t have a William Durant, a Fisher brother, or a Studebaker in the boardroom. Here’s why they failed:

  • Technological Discontinuity
    • Carriages were made of wood, leather, and iron; cars required steel, engines, electrical systems. The skills didn’t transfer easily.
  • Capital Requirements
    • Retooling for cars required huge investment. Most small and midsize carriage firms didn’t have the money—or couldn’t raise it in time.
  • Business Model Inertia
    • Carriage makers sold low-volume, high-margin products. The car business, especially after Ford’s Model T, was about high-volume, low-margin scale.
  • Cultural Identity
    • Carriage builders didn’t see themselves as engineers or industrialists. They were artisans. Cars were noisy, dirty machines—beneath them.
  • Managers versus visionary founders
    • In each of the three companies that survived, it was the founders, not hired CEOs that drove the transition.
  • Underestimating the adoption curve
    • Early cars were bad. But technological S-curves bend quickly. By the 1910s, cars were clearly better. And by the 1920s, the carriage was obsolete.
  • How did you go bankrupt? “Two ways. Gradually, then suddenly.”

By 1925, out of the 4,000+ carriage companies in operation around 1900, nearly all were gone.

The tragedy of the carriage era and lessons for today
What does an early 20th century disruption have to do with AI and today’s companies? Plenty. The lessons are timeless and relevant for today’s CEOs and boards.

It wasn’t just that carriage companies failed to pivot. It’s that they had time and customers—and still missed it. That same pattern happens at every disruptive transition; they were led by CEOs who simply couldn’t imagine a different world than the one they had mastered. (This happened when companies had to master the web, mobile and social media, and is repeating today with AI.)

Carriage company Presidents were tied to sales and increasing revenue. The threat to their business from cars seemed far in the future. That was true for two decades until the bottom dropped out of their market with the rapid adoption of autos, with the introduction of the Ford Model T. Today, CEO compensation is tied to quarterly earnings, not long-term reinvention. Most boards are packed with risk-averse fiduciaries, not builders or technologists. They reward share buybacks, not AI moonshots. The real problem isn’t that companies can’t see the future. It’s that they are structurally disincentivized to act on it. Meanwhile, disruption doesn’t wait for board approval.

If you’re a CEO, you’re not just managing a P&L. You are deciding whether your company will be the Studebaker—or one of the other 3,999.

Why Investors Don’t Care About Your Business

Founders with great businesses are often frustrated that they can’t raise money.
Here’s why.


I’ve been having coffee with lots of frustrated founders (my students and others) bemoaning most VCs won’t even meet with them unless they have AI in their fundraising pitch. And the AI startups they see are getting valuations that appear nonsensical. These conversations brought back a sense of Déjà vu from the Dot Com bubble (at the turn of this century), when if you didn’t have internet as part of your pitch you weren’t getting funded.

I realized that most of these founders were simply confused, thinking that a good business was of interest to VCs. When in fact VCs are looking for extraordinary businesses that can generate extraordinary returns.

In the U.S., startups raising money from venture capitalists are one of the engines that has driven multiple waves of innovation – from silicon, to life sciences, to the internet, and now to AI. However, one of the most frustrating things for founders who have companies with paying customers to see is other companies with no revenue or questionable technology raise enormous sums of cash from VCs.

Why is that? The short answer is that the business model for most venture capital firms is not to build profitable companies, nor is it to build companies in the national interest. VCs’ business model and financial incentives are to invest in companies and markets that will make the most money for their investors. (If they happen to do the former that’s a byproduct, not the goal.) At times that has them investing in companies and sectors that won’t produce useful products or may cause harm but will generate awesome returns (e.g. Juul, and some can argue social media.)

Founders looking to approach VCs for investment need to understand the four forces that influence how and where VCs invest:

1) how VCs make money, 2) the Lemming Effect, 3) the current economic climate and 4) Secondaries.

How VCs Make Money
Just a reminder of some of the basics of venture capital. Venture is a just another financial asset class – with riskier investments that potentially offer much greater returns. A small number of a VC investments will generate 10x to 100x return to make up for the losses or smaller returns from other companies. The key idea is that most VCs are looking for potential homeruns, not small (successful?) businesses.

Venture capital firms are run by general partners who raise money from limited partners (pension funds, endowments, sovereign wealth funds, high-net-worth individuals.) These limited partners expect a 3x net multiple on invested capital (MOIC) over 10 years, which translates to a 20–30% net internal rate of return (IRR). After 75 years of venture investing VC firms still can’t pick which individual company will succeed so they invest in a portfolio of startups.

VCs seesaw between believing that a winning investment strategy is access to the hottest deals (think social media a decade ago, AI today), versus others believing in the skill of finding and investing in non-obvious winners (Amazon, Airbnb, SpaceX, Palantir.) The ultimate goal of a VC investment is to achieve a successful “exit,” such as an Initial Public Offering (IPO) or acquisition, or today on a secondary, where they can sell their shares at a significant profit. Therefore, the metrics for their startups was to create the highest possible market cap(italization). A goal was to have a startup become a “unicorn” having a market cap of $1billion or more.

The Lemming Effect
VCs most often invest as a pack. Once a “brand-name” VC invests in a sector others tend to follow. Do they somehow all see a disruptive opportunity at the same time, or is it Fear Of Missing Out (FOMO)? (It was years after my company Rocket Science Games folded that my two investors admitted that they invested because they needed a multi-media game company in their portfolio.) Earlier in this century the VC play was fuel cells, climate, food delivery, scooters, social media, crypto, et al. Today, it’s defense and AI startups. Capital floods in when the sector is hot and dries up when the hype fades or a big failure occurs.

The current economic climate
In the 20th century the primary path for liquidity for a VC investment in a startup (the way they turned their stock ownership in a startup into dollars) meant having the company “go public” via an initial public offering (IPO) on a U.S. stock exchange. Back then underwriters required that the company had a track record of increasing revenue and profit, and a foreseeable path to do so in the next year. Having your company bought just before the IPO was a tactic for a quick exit but was most often the last resort at a fire sale price if an IPO wasn’t possible.

Beginning with the Netscape IPO in 1995 and through 2000, the public markets began to have an appetite for Internet startups with no revenue or profits. These promised the next wave of disruption. The focus in this area became eyeballs and clicks versus revenue. Most of these companies crashed and burned in the dotcom crash and nuclear winter of 2001-2003, but VC who sold at the IPO or shortly after made money.

For the last two decades IPO windows have briefly opened (although intermittently) for startups with no hope for meaningful revenue, profit or even deliverable products (fusion, quantum, etc. heavy, infrastructure-scale moonshots that require decades to fruition). Yet with company and investor PR, hype and the public’s naivete about deep technology these companies raised money, their investors sold out and the public was left hanging with stock of decreasing value.

Today, the public markets are mostly closed for startup IPOs. That means that venture capital firms have money tied up in startups that are illiquid. They have to think about other ways to get their money from their startup investments.

Secondaries
Today with the Initial Public Offering path for liquidity for VCs mostly closed, secondaries have emerged as a new way for venture firms and their limited partners to make money.

Secondaries allow existing investors (and employees) to sell stock they already own – almost always at a higher price than their purchase price. These are not new shares and don’t dilute the existing investors. (Some VC funds can sell a stake in their entire fund if they want an early exit.) Secondaries offer VC funds a way to take money off the table and reduce their exposure.

The game here is that startups and their investors need to continually hype/promote their startup to increase the company’s perceived value. The new investors – later stage funds, growth equity firms, hedge funds or dedicated secondary funds, now have to do the same to make money on the secondary shares they’ve purchased.

What Do These Forces Mean For Founders?

  • Most VCs care passionately about the industry they invest in. And if they invest in you they will do anything to help your company succeed.
    • However, you need to remember their firm is a business.
    • While they might like you, think you are extraordinarily talented, they are giving you money to make a lot more money for themselves and their investors (their limited partners.)
    • See my painful lesson here when I learned the difference between VC’s liking you, versus their fiduciary duty to make money.
  • The minute you take money from someone their business model becomes yours.
    • If you don’t understand the financial engineering model a VC firm is operating under, you’re going to be an ex CEO.
    • You need to understand the time horizon, size, scale of the returns they are looking for.
  • Some companies, while great businesses may not be venture fundable.
    • Can yours provide a 10 to 100x return? Is it in (or can it create) a large $1B market?
    • VC funds tend to look for a return in 7-10 years.
    • Is your team extraordinary and coachable?
  • VCs tend to be either followers into hot deals and sectors or are looking for undiscovered big ideas.
    • Understand which type of investor you are talking to. Some firms have a consistent strategy; in others there may be different partners with contrary opinions.
  • Storytelling matters. Not only does it matter, but it’s an integral part of the venture capital game.
    • If you cannot tell a great credible story that matches the criteria for a venture scale investment you’re not ready to be a venture funded CEO.
  • If you’re lucky enough to have an AI background, grab the golden ring. It won’t be there forever.