#20 — Chutzpah/Mensch

I’m hoping to get the Chutzpah-Mensch Matrix added to business school textbooks.

The idea came from a conversation Glenn Kelman. When talking about the importance of humility, he said:

Well, you have to have some chutzpah. […But] you have to subject your deepest held convictions to the possibility that you are totally wrong.”

I figured we could double down on the power of #BusinessYiddish and say: 1.) You need some chutzpah; 2.) But it’s more important to be a mensch. 

And since I’m obsessed with 2x2s, I think it works this way:

Built in Seattle Podcast


Galen Ward (co-founder & former CEO at Estately) talks about profitable growth, the story behind his acquisition, and finding the next idea.

On sticking with it:

“We really had no business starting Estately. Thankfully neither of us was employable at a tech company at that time. So we couldn't get a job and we had to just keep sticking with it, until it worked.”

On setting expectations:

“I had run a company that was good and was never a rocket ship long enough that I knew to keep my expectations reasonable. I'm not a golden child where everything just is perfect. So I didn't expect that this would go perfectly.”

Thank you for reading! Replies always welcome. 🙏

— Adam