Over the last two weeks, I’ve been reflecting on why this moment feels so disorienting, even for the people who are excited about AI.
One answer is that the tools are evolving fast.
While that’s true, it doesn’t account for the deeper discomfort I sense.
I think the discomfort has to do with the fact that we are living through a structural shift, not just a technological one.
Most of us learned how to become valuable inside the structure of what I call the “execution economy.”
An execution economy creates value through efficiency, scale and repeatability.
We learned how to get good at something and build our reputation around that competence, performing inside that known structure.
There is comfort in that.
But that structure is starting to fall apart.
We are now moving from an execution economy to a regenerative one.
Instead of prioritizing scale and repetition, a regenerative economy creates value through continuous reinvention, judgment and the ability to originate new value.
In April 2025, Shopify CEO Tobi Lutke shared an internal memo in which he said that using AI effectively would now be “a fundamental expectation of everyone at Shopify.”
He went further than most CEOs would. Teams, Lutke said, should have to show why AI cannot do the job before asking for more headcount. AI usage would also be folded into performance and peer review.
But if you look back further, Lutke had actually started shaping the company for the regenerative economy years earlier.
In another widely-shared memo from 2021, he described Shopify as a “red-queen race,” like in Alice in Wonderland: you have to keep running just to stay still.
In that memo, he put it plainly:
“We all have to re-qualify for our jobs every year. The red-queen race of Shopify's historic 40% or better growth is that everyone has to show up at least 40% better every year to qualify for our current jobs.”
That kind of year-after-year improvement — that regeneration — seemed radical at the time.
But in 2025, AI suddenly made Lutke’s call-to-action a practical goal.
Because when AI speeds and commoditizes our execution, execution no longer gives any organization an edge.
Regeneration is our only remaining advantage.
Shopify built that regenerative structure into its DNA years ago.
Tomorrow’s economy will reward organizations that operate like Shopify.
Lutke saw the regeneration economy coming. That’s what makes him one of the best CEOs in the world.
What he understood early on is something that I’m seeing other organizations only begin to confront:
Yesterday’s company was built to harvest a known advantage.
Tomorrow’s company has to keep producing the next advantage — again and again.
In the execution economy, an organization’s value came from scale, repeatability and process, all built around a single advantageous idea.
Once you found product-market fit, the job was to extend it. Build the machine around it and keep it running. Maximize output.
In the regenerative economy, that structure is a cage. It holds us back.
Execution still matters, but AI makes it cheaper, faster and easier to replicate. The half-life of advantage gets shorter.
Product-market fit is now something you have to keep earning.
In the last edition of this newsletter, I wrote that AI is becoming middleware for human imagination. I meant that. It is starting to sit between what a person can conceive and what a company can make real.
If regeneration is the engine, human imagination is its fuel.
Companies must now put imagination at their center. It can no longer live at the margins.
Imagination is the primary economic driver of the regenerative era.
That means imagination is no longer a creative function. It is economic infrastructure.
The regenerative economy requires new infrastructure: a continuous loop of sensing what’s changing, imagining what new value might look like, acting on it — with AI as the translation layer — learning from what happened, and scaling what works.
I call this the Regenerative Loop. I’ll go deeper on this in a future edition.
While AI compresses this loop, we as people still have to do the hardest parts.
We have to notice what matters.
We have to decide what is worth pursuing.
We have to bear the consequences of getting it wrong.
That is where tomorrow’s value sits.
I’d note that this shift is not just organizational. Every individual also faces the same structural question: What are you regenerating ahead of what AI can consume? I'll come back to this soon.
In early February, I watched as the markets directly reacted to the rise of the regenerative economy, even if they didn’t have that name for it yet.
The SaaS sector lost roughly $1 trillion in market value in seven trading days.
Companies like Salesforce, ServiceNow, Adobe and HubSpot were down more than 30 percent from the year prior.
This “SaaS apocalypse” was evidence that AI is compressing software advantage. Product-market fit is losing its old durability. It has to be earned again and again.
Lutke of Shopify understood that years ago.
His AI memo made headlines, but it was really an extension of the same logic he laid out in 2021: keep improving, keep adapting, keep re-qualifying.
Yesterday
Yesterday, companies won by getting better at execution.
We built around efficiency, stable roles and known models of success.
People built careers by mastering a lane and performing inside a structure that changed slowly.
Tomorrow
Tomorrow, companies will win by regenerating faster than the market shifts beneath them.
They will need shorter feedback loops, looser boundaries, and more capacity to turn human imagination into real economic value.
People will still need a craft. But they will also need to keep evolving it.
Our advantage will not come from protecting the machine.
It will come from renewing what the machine makes possible.
The questions I'm putting to every leadership team I work with right now:
Where in your organization are you using AI to optimize an advantage that is quietly decaying underneath?
What is your organization getting faster at that will matter less by the time you've mastered it?
If product-market fit is no longer a destination but a practice, what does that demand of how you lead?
What are you protecting that is preventing regeneration?
That’s what I’m watching for Tomorrow.
– Nish
A gratitude P.S.
Every year on my birthday, I send a list of things I’m grateful for — one for each year. This year it’s 54.
AI makes it easier than ever to keep working. When the drudgery gets delegated, my creative flow is always available. I’m tempted to stay in it.
Which is why I've become protective of the pause.
Every afternoon, Tomen and I take a nap together. It's non-negotiable. Gloria joins when life allows.
This photo is from one of those moments.
Just the couch, the crew, and the reminder that the best thinking often happens when you’re not thinking.
Some things don't need to be optimized. Some things just need to be protected.
