Casalena: Leaders consistently regret moving too slowly on decisions
Anthony Casalena · Advice Line with Anthony Casalena of Squarespace · Nov 20, 2025 · at 45:34
Squarespace founder Anthony Casalena shares founder reflections and lessons learned on decision-making speed with Guy Raz.
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“And I think that I would look back and go, you know, what decisions do I always delay on? And I'm always looking back and going, I wish I had done that faster. And I wonder why I've never gone to those decisions and gone, wow, I went too fast on that one. Right? Like, why does it always error in one direction? And what does that mean? And I think I try and watch out for that stuff now, and realize that sometimes I never move too quick on certain things, and just kind of keep that in mind, and it's like, you could have just gone faster. You knew what to do.”
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