The 'Wouldn't It Be Cool If...' Framework: How One Question Changed Everything
The simple question that turned curiosity into a 30+ year career building software companies—and why it matters more than ever in the age of AI.
I’ve started hundreds of conversations the same way over the past three decades: “Wouldn’t it be cool if...”
Not “Can we...” or “Should we...” or “Is it possible to...”
Just: “Wouldn’t it be cool if...”
That single question became the foundation of every software company I built, every product I launched, every problem I solved. It’s deceptively simple, almost childlike in its optimism. But that’s exactly why it works.
The Problem with How We Usually Think
Most business conversations start with constraints. Budget constraints. Technical constraints. Market constraints. Time constraints.
“We can’t do that because...” “The problem is...” “Our limitations are...”
We’re trained to be realistic, practical, and grounded. And there’s value in that—eventually. But when you lead with constraints, you kill possibility before it has a chance to breathe.
The “Wouldn’t it be cool if...” question does something different. It bypasses the immediate “no” reflex. It creates a moment of pure possibility before reality sets in. And in that moment, something magical happens, people start imagining instead of defending.
How the Framework Actually Works
Here’s what happens when you ask “Wouldn’t it be cool if...”:
First, you get permission to dream. The question itself signals that you’re not asking anyone to commit, budget, or build—yet. You’re just wondering aloud. That removes the pressure that normally shuts down creative thinking.
Second, you shift from problem-focused to possibility-focused. Instead of “How do we fix this broken process?” you ask “Wouldn’t it be cool if this process didn’t exist at all?” The reframe changes everything.
Third, you invite collaboration instead of criticism. When someone responds to “Wouldn’t it be cool if...”, they naturally start building on the idea rather than tearing it down. The question makes them a co-creator, not a gatekeeper.
Over thirty years, I watched this pattern repeat itself in boardrooms, product meetings, and late-night brainstorming sessions. The companies I built weren’t born from brilliant strategic plans. They were born by someone saying “Yeah, that would be cool” and then all of us figuring out how to make it real.
Why This Matters More Now Than Ever
Then AI arrived, and everything I thought I knew about this framework got amplified by a factor of ten.
Because here’s what I discovered: AI is the ultimate “Wouldn’t it be cool if...” partner.
When you ask a human “Wouldn’t it be cool if we could analyze ten years of customer data and spot patterns we’ve never seen?”, they might say yes, but they’re already thinking about the team you’d need, the time it would take, the cost involved.
When you ask AI the same question, it says “Let’s do it right now.”
AI doesn’t start with constraints. It starts with capability. It doesn’t ask “Should we?” before “Can we?” It just begins creating, building, exploring. And that changes the entire dynamic of what’s possible.
For the first time in my career, the gap between “Wouldn’t it be cool if...” and “Here’s how it works” has shrunk from months to minutes. From hypothesis to prototype. From idea to implementation.
The New Rules of Co-Creation
This is why I’m writing this now, why I’m stepping out after decades of building in the background. Because the “Wouldn’t it be cool if...” framework that guided my career has become exponentially more powerful—and more necessary.
In the age of AI, we don’t need more people asking, “What are the risks?” or “What could go wrong?” We have plenty of those voices, and they’re important.
What we need are more people asking “Wouldn’t it be cool if...”
People who can imagine possibility, then partner with AI to make it real.
People who understand that the question isn’t whether AI will change everything—it already is. The question is what we’re going to build together.
Try It Right Now
Here’s my challenge to you: Take whatever you’re working on right now—a project, a problem, a process that frustrates you—and ask yourself one question:
“Wouldn’t it be cool if...”
Don’t finish the sentence with something realistic or achievable. Finish it with something that makes you think “Yeah, that would be cool... but is it even possible?”
Then open up a conversation with AI and explore that possibility. Don’t ask permission. Don’t start with constraints. Just start with wonder.
You might be surprised by what happens next.
Because in my experience, the most powerful software, the most innovative solutions, the most transformative ideas—they all started the same way.
With someone wondering: “Wouldn’t it be cool if...”