Shamelessness Is a Superpower: Dan Cataldi on Learning as a Founder

5 hours ago

6 min read

Dan Cataldi, founder and CEO of Groove, wrote four words on his napkin. Shamelessness is a superpower. He means the willingness to look like a beginner in front of other people. For a founder who has already built something real, that gets harder with every win. You have a reputation for knowing. Asking the simple question starts to feel expensive. So you protect the appearance of knowing, and the learning slows down. Under the headline, Dan drew three small cartoons. Every expert started as a beginner. Admitting ignorance is how we become informed. And fear of looking stupid kills more dreams than failure ever will. He has tested those lines as an NCAA Division I wrestler, as a surfer who started at 30, and as a founder who set out to change how a foot is fitted to a shoe.

https://www.youtube.com/watch?v=fMLdzCnISqk

Inspired by Paper Napkin Wisdom Episode 377 with Dan Cataldi.

Why does the fear of looking stupid grow as you succeed?

After Brown, Dan worked on a small team that effectively served as chief of staff for the founder CEO of a Fortune 100 company. It was a prestigious job that looked good on paper. He found himself showing up with a kind of shame. He presumed so much expertise already existed around him that if he didn't understand something, he assumed he was the one missing it.

This is a person who, by his own description, does not usually hold his tongue. Even so, he was more scared of being wrong, or of looking like he didn't get something, than he was driven by the chance of being right. He couldn't bring his whole self to the work. Dan is careful to say it wasn't the fault of the job.

Notice the shape of that. A young person assumes everyone else knows. An established owner faces the mirror image. Everyone assumes you know. Both positions make the simple question feel dangerous, and both trade learning for looking competent.

How do you get better at something you are bad at?

Dan grew up with a brother three years older, a very good wrestler who is now a second degree black belt in Brazilian Jiu Jitsu. His point about wrestling is blunt. Beating people up doesn't make you better. "What you need is someone to beat you up." You need a mountain to climb, something that shows you what you currently can't do.

His mother tells a story about it. At a wrestling camp, a 12 year old Dan found the Olympic medalist instructor and went straight in to shoot on his leg. He was willing to get tossed around for the sake of being in it.

Surfing gave him the same thing as an adult. He started at 30, and he describes learning as getting beaten by water he has no control over. It let him be a novice again, play around, and set down the expectations his ego might have put on him as a surfer.

He calls this a continuous process of massaging the ego away, so he can focus on the task and not on himself as the hero doing the task. He talks about "embracing the climb and not just envisioning the pinnacle." Because he is not expecting it to be easy.

How to tell useful feedback from feedback that only feels good

Early in testing, Dan made a pair of Groove insoles for his mother, who had worn medical orthotics for years. She insisted on wearing one of each, one in each shoe. Then she was relieved. His insole felt better, and she had been worried it would be the other way around.

Dan thanked her and pointed out the problem. Her result gave him nothing to fix. Had the medical orthotic felt better, she could have told him why, and that would have helped him close the gap.

That is the habit he tries to keep. Run toward the feedback that shows you where you are behind. In his words, "the feeling of not knowing, of being ignorant, is the process of acquiring new knowledge." He compares it to exhaust, the thing that comes out the other side of moving forward.

He also keeps "a very broad top of the funnel" for feedback, and he makes himself the filter. Listen earnestly to an idea you might not end up agreeing with. Then synthesize your own view from what else you have heard and what you know.

What being wrong taught Dan about the business he was building

Groove started from something Dan watched. NBA stars were giving away their shoes and holding on to their custom insoles. His father had sold orthotics in his practice for years, and Dan had always seen that as lame and stale. Now he wondered if it was where footwear was going next.

His first hypothesis was simple. Make orthotics easier to get. Then he talked to people. Most of his peers had never tried orthotics and didn't think they needed them. So he changed the question. Could the personalization behind orthotics come to footwear more broadly, and could the concept of need disappear? The answer became a product meant to be easy to get, affordable and something people actually want.

Getting there meant asking a lot of questions he didn't know the answers to. Could the Face ID camera on an iPhone take a high precision 3D scan of a foot? Groove built that as its ShapeSense technology. Dan says he still gets things wrong more than he gets them right. He compares startups to baseball hitting, not free throws. Swing at the right pitches and three hits in ten is a Hall of Fame career.

He also broke a rule he was taught at Wharton. Don't build a product for yourself. He did, partly, and he names the condition that makes it work. "The most important thing you need to be able to do is identify where the things that apply to you don't apply to everyone else."

How to lead a team that is afraid to admit what it doesn't know

Dan is direct about his role. He is not a software engineer or an insole maker, and he doesn't manage the shipping. He describes his job as being "the conductor of a band that is filled with people who play instruments perhaps better than I do any individual thing." His work is shepherding the idea, telling it as a story, and finding the people who can bring it about.

He leads the learning by example. When he hands someone a hard problem, he says out loud that he doesn't have the answer and nobody does. They are doing this for the first time. He doesn't expect them to know exactly what to do. He trusts them to be thoughtful, diligent and rigorous, and to experiment.

That permission sits next to a hard standard. From a business lens, Dan is always looking for the outcome, not the effort. Once direction is set, he asks one question. "How can I be most helpful here?" Daily check-ins, a review that pokes holes, or some early ideas. The people he values most take real ownership, so his job becomes being additive to their work.

Shamelessness here is not recklessness or volume. It is permission to begin again, paired with someone who still cares whether it worked.

How to apply this in your business this week

Pick one place where you are protecting the appearance of knowing, and practice the opposite.

Ask the simple question in your next meeting, the one you assumed everyone else already understood.
Find someone who can beat you, a peer, an advisor or a customer, and ask them where your thinking is weakest.
When feedback is only encouraging, ask for the version that tells you where you are behind.
Open your next hard assignment by telling the team you don't have the answer either.
After setting direction, ask the owner how you can be most helpful, and let them choose.

Then take out a paper napkin. Write down one place where shamelessness could serve you this week. Act on it before your old identity talks you out of it.