It’s one thing to have an idea.

It’s another to get it anywhere that feels complete — even done, even beyond the fun exploration.

And this is even more of a challenge when the terrain — like AI today, “Internet” yesterday — keep shifting.

Ten years ago I found myself at the helm of OMATA. As most of you know, that was my hardware startup.

But this kind of startup was not starting up in today’s environment. It was 2015, and most everyone would say to me “dude, don’t do hardware..it’s hard!”

The world was still getting used to the idea of connected devices. The iPhone was only eight years old, and wearables were slipping in the mud trying to get some traction.

And sure enough, hardware *was hard.

And here I was, making what seemed at first an absurd proposition: a cycling computer that was analog, indexed more on soulful than instrumented data collection. It was as if what I was proposing was some kind of alien artifact from an alternate universe.

The world didn’t need another sports tracker device, everyone said. There were cheaper, faster, more “rational” options. Wahoo, Garmin, Hammerhead — these were all dominating a niche of a niche in the marketplace. Even as these were barely differentiated by features, it seems unlikely that an underfunded, earnest guy working in his backyard studio could compete.

But here’s the subtle but important “differentiator”: I wanted something into which I could pour a story..some kind of contrivance that would invite people into a different relationship with cycling, technology, and their own sense of movement.

What I learned along the way was that the real challenge wasn’t the engineering, although that was hard (and worth of a patent! I’m genuinely proud of having written that!) It’s making meaning, building a vision that people can see themselves in. There’s no instruction manual for this.

Some days, you’re sweating cash flow and supply chain. Others, you’re conjuring a future that doesn’t exist yet and doing fun (but hard) things like creating mock ads for features no one asked for, testing assumptions by writing fake reviews to capture perceived weaknesses, anticipated user needs that don’t yet exist, building internal decks full of possible upgrades, brand collabs, write-ups as they might appear in my favorite publications and blogs.

Was all of that make-believe? Sure, but a different kind of make-believe. The kind that helped me clarify not just what we could do, but what we should do.

When my co-founder left, it drove home another lesson: a team without shared imagination and a willingness to engage in “productive pretending” is just a group of operators, not a creative force. The future doesn’t reward the most efficient executors; it rewards those who can sense the next turn before the map gets drawn.

And this is where many product teams find themselves today. With AI accelerating change and roadmaps shrinking, the old playbooks are running out. Leaders can’t just optimize for efficiency anymore. They need teams who can sense what’s next, experiment bravely, and shape stories before the category exists.

There are many, many lessons I learned over the 10 years of running OMATA. Most of them are so embedded in who I’ve become as a creative, a product designer, engineer, and entrepreneur that they’ve just ended up in a kind of intuitive knowledge.

But, one bit of advice that stands out is this: Invest in your team’s imagination. Build a space for disciplined speculation and creative risk-taking. The organizations that do this aren’t just ready for the next shift because they will always-already be inventing it.

In the next post, I’ll share how making the future tangible through speculative design and prototyping helps product teams move beyond abstraction and into the kinds of breakthroughs that slide decks and roadmaps can’t deliver. This is beyond “thinking outside the box” — it’s about creating new boxes altogether. It’s about accepting that the AI future in particular is like a new expansive terrain for which the old ways of making sense of possibility are too small.

Whether or not you like AI, it’s here, and it’s changing everything: and the first thing it’s changing is our sense of what’s possible. Whether or not it turns out to be a big deal, or a passing fad, it’s already changing how we think about knowledge, work, creativity, and even what it means to be human. That shift in consciousness itself is a big deal — and it’s one that requires new ways of thinking, making, and imagining.