I Read The Art of the Deal, So You Don't Need To

Rakhee had a knock to the head and decided to read Donald Trump’s The Art of the Deal. Interviewed by Heather, the hosts pull apart the book’s gold-plated bravado, missing negotiation strategy, and questionable legacy. Expect sharp takes, a few laughs, and some actually useful book recommendations along the way.

 Recommended Reads Mentioned in This Episode

• Getting to Yes – Roger Fisher & William Ury

• Pour Your Heart Into It: How Starbucks Built a Company One Cup at a Time – Howard Schultz

• Let My People Go Surfing – Yvon Chouinard (Patagonia founder)

• Nuts! – Kevin & Jackie Freiberg

• The Tesla Files – Investigative exposé on Tesla

• Patagonia: Founder’s Story – Shunsuke Chouinard / additional Patagonia insights

 

Episode Transcript

Heather DeLand (00:32):
Well, I don't know what I've let myself in for this episode. Rakhee has gone and done the thing that I still, to this day, swear I will never do, which is read the non-masterpiece that is The Art of the Deal. No way in hell would I ever go in, so this whole episode is actually just going to be a reveal for me—and for you, the listener—if you have also never read this wonderful, wonderful business book. Everyone says it's the best book. It's a bigly good book, I'm sure. Tremendous. It's huge. It's huge. It's huge.

Rakhee Verma (01:00):
Mmm. Tremendous, tremendous book.

Heather DeLand (01:23):
I mean, where do we start? There's a lot of unknown unknowns for me, right? I'm guessing if it's called The Art of the Deal, presumably there are deal examples, presumably there is a business philosophy. I just don't know where to start. Maybe if you give us a little overview. Did you read the whole thing, by the way?

Rakhee Verma (01:43):
I read the whole thing. I listened to it on audiobook and was worried that Trump was going to read the whole book.

Heather DeLand (01:51):
God, I would be. Was it him? He can't read? It wasn't him?

Rakhee Verma (01:54):
No, thankfully, somebody else reads it. One of the things I will say is every three or four chapters I had to up the speed on the audiobook, so by the last three chapters we were on 1.5x. This dude is speaking incredibly quickly, and when we talk more about the book you'll see why I just sped through it in the end. But I didn't want to do a disservice to anyone listening, or to you as the interviewer, by cheating and not finishing it. So I did read all of it. I just wanted to say a couple of things before we get started. One is I feel qualified to read and comment on and review this book because I have been previously in my life, a sales director, business development director. I'm a commercial mediator, which means I have advanced negotiation skills when it comes to making deals. So I did read it very much with that lens, but also you cannot divorce yourself from the fact that we know what we know about Donald Trump now—as a president and watching him particularly do these tariff deals in inverted commas. You just can't separate yourself from that. So I just wanted to say that upfront. The other thing I just wanted to say before we get going is for people that don't know, it was co-authored, i.e. written by Tony Schwartz, who subsequently has come out and said that he really regrets writing this book. He feels a deep sense of remorse, I think, with the exact words.

Heather DeLand (02:38):
Okay.

Rakhee Verma (03:56):
And he likened it to putting lipstick on a pig. And I think he feels he's helped to create this myth that Donald Trump is this amazing business person. To be fair to Trump, he sold over a million copies of this since 1987 when it was published. It became a best seller at the time. It has been a great marketing tool for him, and I think it is still regarded as one of the most commercially successful business books of its era. So that's me trying to be balanced. That's probably about it in terms of balance for the rest of this discussion. But anyway, over to you. Sorry, you did ask me a question I've forgotten.

Heather DeLand (04:43):
No, it's okay. I haven't read the book, so I almost don't know what to ask you. But I guess one of the things that comes to mind for me is here is a guy who's given himself permission to write a book about making deals. You know, you bothered at the start of this conversation to credentialise yourself as to why anyone should listen to your deal-making consultancy and energy because you've got experience doing it. This is a guy, I don't know if it has anything biographical to sort of set it up, but like, you know, this is a guy who came in with his dad's money to gamble in business. I know that much about him. You know, is there a moment at the start of the book where he actually credentialises himself to be like, this is why you should listen to me as a dealmaker? Or does he just assume we trust him?