The Rise of AI: A Technological Turning Point
Artificial Intelligence (AI) is shaping up to be the biggest technology craze of the century. 42% of U.S. venture capital was invested into AI companies in 2024, and generative AI is expected to reach a global market value of $51.8 billion by 2028.
If you haven’t already begun to drink the AI Kool-Aid within your own company, you’re likely wondering: Should I jump in, or should I wait?
To answer that question, let’s take a trip back to the emergence of another trending technology: the internet.
1995: Three Boardrooms and a Dilemma
Picture this: the year is 1995, and there are three concurrent board meetings being held. One at the headquarters of Borders Books, one at Domino’s Pizza, and one at Trader Joe’s.
At this point, the graveyard of revolutionary technologies peddled by fresh MBAs is already filling up nicely. There had been the promise of interactive cable eliminating the need for physical stores, and of videotex terminals transforming retail forever.
In light of these flash-in-the-pan trends, being skeptical of the latest crop of breathless graduates is proving to be a solid boardroom strategy.
And now, these boardrooms find themselves listening to another twenty-something, still breaking in their first Brooks Brothers suit, sweating through the biggest presentation of their career. “The internet changes everything! Sure, only 14% of Americans have it, and most of them are using CompuServe to argue about Star Trek, but we need to pivot our entire company right now!”
And in each of these boardrooms, wiser heads prevail. Seasoned executives point out that yes, the internet shows promise, but mass adoption is still years away.
Wait-and-See: A Seemingly Safe Strategy
All three companies are thriving in their lanes – selling books, pizzas, and groceries – and each has built its success on understanding their customers deeply. If you’d lined up those CEOs and asked them about online retail, you might have heard three thoughtful, nearly identical answers: “We’re studying it carefully. When the technology matures and our customers are ready, we’ll be ready too.”
Some of them would have, in fact, been right.
Domino’s: Patience Meets Innovation
The pizza makers had read the room perfectly. Domino’s watched the internet mature, waited for broadband to reach critical mass, then pounced. They didn’t just build a website – they rebuilt their entire operating system from the ground up.
Today, a college kid can order a pie by texting a cartoon emoji, watch their driver dodge frat houses on a digital map that looks lifted from Grand Theft Auto, and rate the whole experience with a smear of their now-greasy thumb. That emoji-to-doorstep revolution sent Domino’s stock up 2,442% – enough to turn $10,000 worth of pizza shares into Domino’s franchise of your own.
Borders: Strategic Thinking Gone Wrong
And now our eye turns to Borders, which made an equally sophisticated calculation.
While Amazon was incinerating their IPO cash on warehouses and servers – losing $1.4 billion in 2000 alone – Borders doubled down on what it did best: creating beautiful spaces where people could browse, read, and connect. They partnered with Amazon for online sales, a move that perfectly aligned with business school wisdom and nicely boosted the stock price.
Suckers like Barnes & Noble were spending hundreds of millions to build their own ecommerce platform, while Borders got instant digital presence without the infrastructure costs. It was textbook strategic thinking: leverage your core strengths, learn from the best, keep your options open. The logic was impeccable – exactly the kind of MBA-approved thinking that would lead a century-old business to hand its future to its executioner.
Trader Joe’s: The Art of Nonchalance
Finally there was Trader Joe’s, which took “wait and see” to its logical extreme: they’re still waiting. No Instacart. No delivery. No online ordering of any kind.
They sat out the internet with a smile. And since 1995, they’ve grown from 70 stores to nearly 600. Revenue has soared from $600 million to over $16 billion. They generate $1,750 in sales per square foot – double what Whole Foods manages with all of its Amazon-powered tech.
While other retailers chase digital transformation, Trader Joe’s keeps paying actual humans in Hawaiian shirts to ring actual bells to help you carry groceries to your actual car. You still can’t buy Everything But The Bagel seasoning from your couch, and that’s exactly the way everybody likes it.
The Internet Took Decades – AI Moves Faster
It took decades for these internet stories to play out. The next wave wouldn’t be so patient.
On November 30, 2022, while retail executives were still sorting through their Black Friday results, a small research lab released a demo. No press conference. No marketing campaign. Just a brief blog post: ‘We’ve trained a model which interacts in a conversational way.’
A few months later, hopeless romantics were using it to polish their profiles on Tinder, Methodist ministers were using it to scribe sermons, and lawyers were getting sanctioned by judges for submitting its work as their own. By the time most executives had finished reading their first memo about AI strategy, their teenagers were already using ChatGPT to write college essays.
The Acceleration of Adoption
Now time itself has compressed. In 1995, when those three boardrooms made their ‘wait and see’ decisions, the internet was barely two years old.
Only 14% of Americans had access. It would take six more years – until 2001 – before internet adoption hit 50%.
That’s when Borders made its fateful handshake with Amazon. By the time Domino’s went all-in on digital in 2007, three-quarters of Americans were online.
The whole transformation played out like a family sedan on a Sunday drive. You could see the infrastructure being built – the fiber getting laid, the warehouses rising up, the delivery trucks hitting the roads. Change had a physical shape, which meant you had time to study it, to wait for the right moment to merge into traffic.
ChatGPT went from launch to 50% adoption four times faster than the internet. Today’s executives are navigating prudently – quarterly board meetings, annual strategies – while technology is on lap 44 at Monaco.
Devja Vu in the Boardroom
Somewhere today, another 20-something in another Brooks Brothers suit is sweating through another career-making presentation. “All in on AI”. The executives listening have heard it all before – they waited out the metaverse and saved billions, they skipped crypto and dodged a bullet. Their skepticism has served them well.
And like those executives in 1995, many will probably make the perfectly rational decision to wait and see. After all, it worked for Domino’s. And Trader Joe’s. And Borders, right up until the moment it didn’t.
