Never Be Afraid to Look "Stupid": Why Founders Should Ask More Questions

"I don't know what that means. Can you explain it?"

I said this out loud in front of a room full of founders during a recent Black Youth Entrepreneur & Innovation Program (BYEI) workshop.

The topic? Palm Pilots and Weird Al.

Seasoned operators in the workshop, Jim and Marc, were referencing them with absolute nostalgia. I smiled and admitted, "I think I know what it is, but I can’t quite place it..."

The room had a good laugh over the generational gap. But it pointed to a lesson every founder needs:

Never be afraid to look stupid in the room.

Early in my career, in my 20s, I was terrified to ask questions. If someone used a term or acronym I didn't know, I stayed quiet.

Then two things shifted:

1. I watched hyper-accomplished, senior leaders casually stop meetings to say, "Hold on, what does that

mean?" They had zero ego about learning.

2. I launched my own business. With no mentor handing me answers, I had to learn everything on the fly.

Now, six years into full-time entrepreneurship (11th including side hustles), I ask "stupid" questions constantly:

"I’m sorry, I didn’t catch that term, could you explain it quickly?"

Nobody knows everything, whether they’ve been in business for 5 years or 30. We hold back because we fear ten seconds of embarrassment.

Ask the question. Clarify the acronym. Learn the lesson.