People, Ideas, & Stories shaping how we work, live, and build the future.

Why it matters: One of the world’s best-run companies just changed how hiring works—and it signals a shift most leaders aren’t ready for.

The big picture: Shopify is forcing teams to prove AI can’t do the job before adding people. They’re not experimenting. They’re restructuring how work gets done.

Between the lines: This isn’t a Shopify story. Nearly 90% of CEOs already rely on AI every day—and the quiet risk isn’t replacement, it’s complacency.

What’s coming: History shows that leaders who mistrust automation fall behind—but those who trust it blindly crash even harder.

The question: Will AI make your team sharper—or slowly put them on autopilot?

Shopify CEO Tobi Lütke recently told staff they must “demonstrate why they cannot get what they want done using AI” before making new hires or resources. Forbes and WSJ called it a wake-up call for the rest of the business world.

If Shopify is betting on AI-first, the rest of us should be paying close attention.

But, Shopify isn’t alone. A new report shows nearly 9 out of 10 CEOs already use AI in daily operations. This isn’t about the future—it’s about right now.

Imagine finishing a project while you sleep. Not because you stayed up all night, but because AI handled it while you rested. That’s not fiction. That’s business in 2025.

That’s the key finding in a new report from international law firm Womble Bond Dickinson (US) LLP titled "The View From the Top: How Business Leaders Are Using AI." Based on interviews and surveys with CEOs and CTOs, the report reveals how deeply AI shapes business strategy, operations, and workforce design. The big idea is that AI isn’t replacing people but repositioning them.

Read the full report

A Look Back: Flying Without Touching the Controls

In the early 1930s, aviation entered a new era of automation. In 1933, the Boeing 247 debuted as one of the first modern airliners equipped with advanced instrumentation and autopilot capability, designed by Sperry Gyroscope Company. That same year, pilot Jimmy Doolittle publicly demonstrated "blind flying" using instruments and an early autopilot system—a milestone widely praised in the press. While some in the public remained wary of pilotless flight, news coverage generally emphasized the innovation.

Eddie Rickenbacker, a World War I ace who later led Eastern Air Lines, admired technological progress but maintained a conservative approach to adoption.

Eddie Rickenbacker, a World War I ace who later led Eastern Air Lines, admired technological progress but maintained a conservative approach to adoption.

As president, he was known for resisting rapid shifts to automation and delayed the airline’s move into the jet age, a decision that eventually put Eastern at a competitive disadvantage.

“I pay those guys to fly,” he said. “I’ll be damned if I’ll pay them to just sit there.”

Eastern Air Lines was one of the last airlines to start using autopilots. Eddie Rickenbacker, who ran the company for many years, believed pilots should rely on their own skills and didn’t fully trust machines to fly the plane.

As Rickenbacker got older, he became more set in his ways. For example, he didn’t want to switch to faster jet planes and insisted on using older turboprop planes. That decision hurt the company’s profits.

Eventually, Eastern’s top leaders decided it was time for a change, and Rickenbacker was removed as CEO on October 1, 1959.

Still, his way of thinking stuck around. One example came in 1972, when Eastern Flight 401 crashed. The National Transportation Safety Board (NTSB) said Eastern taught pilots how to use autopilot, but their rules made it hard to actually use it during flights. This showed how strict the airline still was about trusting new technology.

That cautious approach helped pilots stay alert, but it also kept Eastern from moving forward. By the time the airline went bankrupt in 1989, others had already passed it by.

The lesson? Ignoring or underusing smart tools is just as risky as overusing them.

Now, the same debate is playing out. Only this time, the cockpit is a conference room and the autopilot is generative AI.

The Cost of Complacency: Learning from the Skies

But there’s another side to the story. In 2009, a Northwest Airlines flight flew 150 miles past its destination in Minneapolis. The plane was on autopilot and flying safely—but the pilots weren’t paying attention. They were busy on their personal laptops and lost track of time.

This is called automation-induced complacency—when people trust the technology so much that they stop doing their jobs. The FAA took away both pilots’ licenses because they failed to do what they were supposed to: fly the plane.

The Flight Safety Foundation says this is a growing problem. Watching a machine isn't easy—most people would rather be doing something than just paying attention.

But that’s the new job in AI-heavy companies: watching the machine.

The problem is, what if the system makes a mistake and no one notices?

Aviation has learned this the hard way. Now it’s experimenting with adaptive automation—giving pilots more control during low workload periods to keep them sharp. Business should do the same. Keep people in the loop. Train them not just to trust the system, but to question it.

Last Time the Market Was This Expensive, Investors Waited 14 Years to Break Even

In 1999, the S&P 500 peaked. Then it took 14 years to gradually recover by 2013.

Today? Goldman Sachs sounds crazy forecasting 3% returns for 2024 to 2034.

But we’re currently seeing the highest price for the S&P 500 compared to earnings since the dot-com boom.

So, maybe that’s why they’re not alone; Vanguard projects about 5%.

In fact, now just about everything seems priced near all time highs. Equities, gold, crypto, etc.

But billionaires have long diversified a slice of their portfolios with one asset class that is poised to rebound.

It’s post war and contemporary art.

Sounds crazy, but over 70,000 investors have followed suit since 2019—with Masterworks.

You can invest in shares of artworks featuring Banksy, Basquiat, Picasso, and more.

24 exits later, results speak for themselves: net annualized returns like 14.6%, 17.6%, and 17.8%.*

My subscribers can skip the waitlist.

*Investing involves risk. Past performance is not indicative of future returns. Important Reg A disclosures: masterworks.com/cd.

AI Is Everywhere Now

According to the WBD report, 87% of CEOs and 97% of CTOs say AI is already integrated into their operations. It’s analyzing data, speeding up decisions, and cutting costs.

For example, at our Massif Studio & Production company, a portfolio company in Drive Phase Holding Co, we launched a new client website almost every other week in 2024. AI helped us go from whiteboard to prototype before launch. The tools handled the grunt work. AI isn’t replacing anyone; it’s elevating the work. Now, as we find ways to deploy it more than ever, I'm focused on developing taste among the team, which we think will be the differentiator. Additionally, our thought process is that AI in the hands of the extremely intelligent team members is a factorial advantage, where every new capability unlocked exponential combinations of ideas and output.

Early-generation AI tools helped us move faster from idea to mockup. This year, those tools are getting us even further down the road. Copywriting, layout variations, SEO setup—all done in seconds. We can give clients something sharper, faster, and more aligned.

It’s making space for more generalists while raising the ceiling for specialists. Industrial revolutions always remove drudgery so we can do more of the work that matters.

Jobs Will & Should Change

AI is reshaping roles. Some will vanish, and others will appear. WBD’s survey shows that 73% of CEOs think AI will replace certain roles, but 69% also expect entirely new ones to emerge.

Think of it like the calculator. It didn’t kill math. It made room for more complex thinking.

We’re already seeing new roles: designers who code, marketers who edit video, and project managers who build in 3D. Entire job categories—prompt engineers, AI ethicists, synthetic data trainers—now exist that didn’t exist two years ago.

The Hard Part? Staying Human

It’s easy to get excited about AI. But smart businesses also see the hard parts:

  • It’s expensive to implement.

  • It raises tough questions about bias and fairness.

  • It needs massive amounts of good data.

  • And it doesn’t work without clear policies.

Caroline Churchill, a partner at Womble Bond Dickinson, says it best: AI is helping companies manage complexity and risk—but only when integrated thoughtfully. Like cars in the early 20th century, AI changes how we move, work, and think. But we still need the roads, the rules, and the driver’s education.

So, What Should You Do?

If you’re building a business, managing a team, or launching your career:

  • Don’t fear AI. Lean into it and learn how to use it wisely.

  • Don’t ignore it. Find ways to integrate it into your workflows.

  • Don’t replace people. Retrain them for higher-value thinking.

Every industrial leap—steam, electricity, silicon—began with uncertainty and then unlocked transformation. AI is no different. It’s not just a tool for cost-cutting—it’s a lens to reimagine how we work.

The most forward-looking leaders will use AI to strip out the rote, the repetitive, and the draining—and reinvest that time in judgment, service, and creativity.

Read More:

Keep Reading

No posts found