The Pivot as a Design Decision
On prototyping a company, and designing yourself as a founder
A Wednesday night in February. Downtown San Francisco. I’m walking out of a friend’s office and the smart ring is on my finger and I feel nauseous. Not metaphorically. Physically nauseous. Three months of endless days behind me. Manufacturer quotes. Samples arriving from China. Multiple form factors tested. The iOS app rebuilt a hundred times. And here I am, standing on the street, wearing the thing, and I don’t want to use it. I don’t need it. It’s making me sick.
I called Kush, my cofounder. I told him I didn’t feel well. That this wasn’t the right thing. That something needed to change.
Startup culture gives you two stories for this moment. The failure story, or the redemption story. Both are borrowed narratives. Neither is mine.
I’m a designer. I have my own language for what happens when something isn’t working. I don’t call it failure. I call it iteration. I call it the moment a prototype reveals its own proportions are wrong, and you set it aside.
Jony Ive once said: “It is so important to be light on your feet, inquisitive and interested in being wrong.”
Interested in being wrong. Not tolerant of it. Drawn to it. Because wrongness is where the information lives. My cofounder would complain about me changing my mind all the time. But that mental agility, that willingness to turn the object in your hands and look at it from another angle, is not indecisiveness. It’s a design skill. Maybe the most important one.
A startup is a design process. But what you’re designing isn’t just a product. You’re designing the match between your strengths and the right problem. And that match doesn’t reveal itself through analysis. It reveals itself through building.
The prototype pile
Before the ring, there were other prototypes.
AR glasses with a haptic ring. Companion robots for kids. A robot vacuum with personality. A wearable for cognitive augmentation. We explored everything. Surveyed 1,500 potential users. Went to CES. Met manufacturers from Shenzhen. Conducted hundreds user research interviews. Partnered with a Belgian design studio. Ran ad campaigns. Each direction was real work, real conviction, real months of our lives. Real money from investors who believed in us.
None of it was casual. We weren’t dabbling. We were committed, every time, until the evidence told us to stop.
Don Norman writes in The Design of Everyday Things: “A brilliant solution to the wrong problem can be worse than no solution at all: solve the correct problem.”
But here’s what Norman doesn’t say: the hard part isn’t finding a problem. Problems are everywhere. The hard part is finding the problem that’s yours. The one you’re interested in enough, and have the capability to solve.
The problem we solved was never the same from one prototype to the next. The robot vacuum solved a utility problem. The companion robot solved a presence problem. The wearable solved a capture problem. Each was a real problem. None of them was our problem.
And you can’t figure that out from a spreadsheet. You figure it out through prototyping. Through the physical, visceral act of building something, living with it, and asking yourself: does this feel like mine?
No quantum leaps
I’m not the first person to iterate through years of wrong shapes.
Tony Fadell spent a decade building the same vision in different shells. Handheld communicators at General Magic. PDAs at Philips. A music player at his own startup Fuse, rejected by 80 VCs. None of it worked. Then Apple called, he built the iPod, then co-created the iPhone, which was, in his words, “General Magic all over again.” The vision never changed. He didn’t find a new problem. He found the right context for the problem he’d always cared about.
James Dyson built 5,127 prototypes of his vacuum. One variable at a time. “There is no such thing as a quantum leap. There is only dogged persistence, and in the end you make it look like a quantum leap.”
Super8 looks like a quantum leap from robotics to software. From the inside, it’s prototype 5,128. The robot work taught us to build with autonomous software and AI models, to think in terms of systems that perceive and act without human intervention. The connected wearable taught me to build beautiful companion apps, software that earns a place in someone’s daily life through craft and care. And having to sell products to people, pitching investors on things that didn’t exist yet, taught me to become an obsessive creative director. I had to stage products I hadn’t built into images and websites that made people believe. I got very good at it. I just didn’t realize that was the skill.
Nothing was wasted. Each prototype deposited something. It just compounded invisibly until it had a shape.
The night it turned
Stewart Butterfield, while Glitch was still a game that wasn’t working, described the bind every founder knows: “On the one hand you have the narrative of: good entrepreneurs are resilient; when everyone else thinks it’s a bad idea, it’s probably a really good idea; you have to dig in and prove people wrong; keep going even when times are dark. On the other hand, there was a morning when I woke up and was like ‘I can’t do this anymore.’”
I know that morning. Mine was a Wednesday night.
Three months in the ring. Manufacturer quotes. Samples from Shenzhen. Form factors tested until my eyes blurred. The app rebuilt over and over. Walking down the streets of downtown SF with this thing on my finger and feeling nothing but resistance. My body telling me what my mind hadn’t caught up to yet.
When a prototype is fighting you, it’s telling you something. A designer knows this. The material speaks. You just have to stop long enough to hear it.
The turn wasn’t a sudden revelation. It was a pattern I’d been ignoring for months. Every time I’d show images of a product I’d designed, people would compliment the product. But mostly they’d compliment the image. I’d send a website for something we were testing and people would say “Wow, the images are so good.” Not “I’d buy this.” The images. The staging. Friends kept telling me I should commercialize my taste. I kept brushing it off because I thought the point was the product, not the picture.
I was wrong. The taste wasn’t a means to an end. It was the end.
What I enjoy the most is not selling products to people. It’s making products look good. When you’re a consumer hardware company, you design the product once and then it’s all about manufacturing and distribution and sales. The design loop closes. You step out of it. You become an operator.
But what if you built software that let you stay in that loop forever? What if the design loop was the product?
Conviction is designed
Some people tell me I don’t have conviction. That I change my vision too often. VCs love the founder who’s been dreaming of the same product since they were nine years old. I don’t buy that. I think that story is almost always written backwards. People rewrite their origin stories once they know the ending. They compress years of confusion into a clean line and call it destiny.
Conviction isn’t an input. It’s an output. You build it through the process of designing the company. Each prototype, each wrong turn, each moment of nausea on a street in downtown SF, is a data point. And at some point the data points converge and you feel something lock into place. Not because you decided to believe. Because you’ve built enough to know.
Kush would complain about me changing my mind all the time. But each change was a rotation of the object. A new angle of observation. I’m someone who’s curious about everything. I can get passionate about any subject if I spend enough time inside it. Some people see that as a lack of focus. I see it as a wider search radius. Curiosity is the raw material. Conviction is what forms when curiosity meets the right problem, the right capabilities, the right moment.
Brian Chesky, who studied industrial design at RISD, said it at Figma’s Config: “I designed our business model. I designed our expense base. I helped design our organizational chart, our business, how we work, our story. Design is not just how something looks, it’s how it fundamentally works.”
I didn’t pivot my company. I redesigned it. And the conviction followed.
The prototype that mattered
David Kelley, the founder of IDEO, said: “Fail early to succeed sooner.” I’d rewrite it. My version isn’t fail fast. It’s prototype fast. Stay light on your feet. Stay interested in being wrong.
The companion robot taught me to design technology that earns its place in someone’s life. The connected wearable taught me to build beautiful companion apps. The ring taught me to trust my body when my mind was still rationalizing. And the months spent staging products into images and websites taught me that creative direction was the work I’d choose even if nobody was paying me.
The conviction I have now for Super8 didn’t come first. The prototypes did.
The ring is still in a drawer somewhere. I look at it sometimes. It’s not a failure. It’s a prototype. The one that taught me what I was actually looking for.