I remember there was a girl that I worked with that was really pretty and could have been charging a lot more. But she had no self-esteem. She had no confidence. And she was charging like the bottom of the barrel. She was actually one of the girls we had a bit of an issue with. And we sat down with her and said, “Look, you know, you’re lowering the house value. You could be making more.” I think she got a little offended by that. So I sat down with her one-on-one. And I told her. “Look, if you ask for it and you’re confident, you will make it. You will make that money, you know?”

She said she felt bad asking for $1,000 or whatever it was. She didn’t feel confident enough to ask for more than $300 or $400, even if it was a longer party. And I told her, “You’re crazy. Double that. Triple that. You’ll find guys that’ll pay. And if they don’t, you negotiate. But if you start low, you have nowhere to go but lower. You know? So you have to start high, and then there’s room for negotiation and to go lower or upsell and go even higher.” But to start at the minimum is just not wise as a salesperson, in my opinion.

On telling her family:

Oh they are not happy. They’re not happy. I kept it from my dad for a long time. He knew what I was studying, and he thought I was just like living there and, like, going to visit. My mom knows me better than that. So she was a little suspicious and started asking a lot of questions. And I’m seeing more and more interviews and I had done some stuff on TV and I was like, ‘This was going to come out.’

So I told her first and, you know, she was just, “I’m Portuguese, my family is Catholic.” She was horrified. I’m so close to them. We still talk, you know, they haven’t cut me off or anything, but you know loving parents. They’re still happily married, but my mom freaked out and she said, “You must never tell your dad.”

You know, like hopefully he dies before this all gets published. I mean she was really adamant about not telling. So I kept it from him for almost a year and then finally I just, you know, got pissed off and I got into a fight. “I’m sick of lying to you and keeping up with the lies.”

You know, he’d call me…and I’d be living there and working and I’d say, “I’m just here for research.” I like it too much, so I just told him, and he was not happy, but he took it better than she did and just said, “Well I don’t understand that. I don’t agree with it.”

📬 Sign up for the Daily Brief

Our free, fast, and fun briefing on the global economy, delivered every weekday morning.