It Always Takes Longer Than You Think

Guy Raz Newsletter – August 29, 2024

One of the reasons I enjoy interviewing late-stage entrepreneurs is that they have a perspective on time. It’s not only that they’re older…but they are also battle-tested. 

They have seen the ups and downs. They’ve experienced massive success and teetered on the brink of failure. They have believed and doubted.  They have seen it all… and lived to tell the tale.

And there’s a simple truth late-stage entrepreneurs know: it always takes longer than you think. 

This week, you’ll hear from Seth Berkowitz of Insomnia Cookies. He grew his fresh-baked cookie brand from his college apartment to hundreds of locations worldwide. 

What’s even more interesting is how long it took. 

Seth’s Insomnia story has a little bit of everything: skyrocketing success, near catastrophic failure, late nights, sweat, and tears. There were dozens of times when he almost – and maybe should have – given up. 

As you’ll hear Seth share, a tiny sliver of hope kept him going. He always felt like he was just around the corne…