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The Playbook With David Meltzer

The Truth About Doing Business With Jerks

The Playbook With David Meltzer

David Meltzer, Entrepreneur.com

Entrepreneurship, Business, Careers

4.61.9K Ratings

🗓️ 24 July 2025

⏱️ 18 minutes

🧾️ Download transcript

Summary

In today’s episode, I sit down with Anthony Scaramucci, investor, author, and founder of SkyBridge Capital, for a conversation about decision making, resilience, and the value of kindness in business. Anthony shares how insecurity shaped his early career, why being decent to a server led to a $35 million opportunity, and how falling off the ladder revealed who was really in his corner. We talk about equity of opportunity, the pressures facing young men today, and what led him to co-create The Lost Boys podcast. He also gives a preview of what’s ahead at this year’s SALT Conference in Jackson Hole.

Transcript

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0:00.0

Welcome to Entrepreneurs the Playbook. I'm David Meltzer. And every once in a while in one of these

0:05.1

2400 episodes that I've done, I get somebody again that I'm just super excited to hang out with.

0:11.0

And it's close to Fourth of July when we're filming this. And I feel like I'm having fun with a friend

0:16.0

on different coasts. But this is someone who I share a frequency with, whether he was working with

0:22.4

Trump or working with Bitcoin. It doesn't matter what the guy does. He is a fantastic,

0:29.1

intelligent, positive person, and the world needs to know what makes him tick. That's why I

0:34.6

created the playbook. Anthony Scarmucci, welcome to the playbook.

0:39.9

Well, first of all, I'm flattered to be asked to come on. I am a fan of yours. And I've downloaded your,

0:50.4

you have a book about making decisions on the fly. and I'm trying to remember the name of it,

0:56.0

but I think it's game time decision making.

0:59.3

And I downloaded the book.

1:01.1

I think he wrote that book either in 2020 or 2019.

1:05.3

And so I'm going to tell you the story.

1:07.1

So, you know, I was in the airport, and I I saw the book and I was looking through the book

1:12.8

and I'm like all right I can't I don't really want to carry it so I downloaded the book

1:16.9

into my phone and then I got the audible and I thought it was a very thoughtful book about

1:23.3

you know the fluidity but one of the things you say in the book, which I want to emphasize here, which I learned from you, is you're going to make mistakes in your decision making and don't get so uptight. Like, you know, you should do OCD training for people, you know, because sometimes I overthink stuff. And, you know, I think the message of that book was, okay, you're at the line of scrimmage,

1:46.6

you're going to fumble the ball, throw an interception, get back to the line of scrimmage, you know, shut up. That was the message of the book. And so I remember the book and when I heard that you were going to invite me on, it was very flattered. Well, I'm very flattered that you came on and a fan of your podcast, Lost Boys Well with Scotty Galloway, which is awesome.

1:47.5

But, Lost Boys,

2:01.7

well with Scotty Galloway, which is awesome.

2:04.2

But, you know, speaking of books, my next book that's coming out Super Bowl with Simon

2:11.2

Schuster is called Don't Do Business with Dix.

...

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