The Time I Loaned A Billionaire $20

Even though I spent seven years working for Ralph Lauren as his company’s in-house photographer in the early aughts, I didn’t actually interact with him all that often. I was usually one degree away, working with the people who worked with him. He would say hi when he saw me but I was pretty sure he didn’t know my name.

Around the same time I joined the company, so did Ralph’s son David. Word was that David resisted joining the company, preferring to make a name for himself without his father’s shadow looming. He had already launched a major venture on his own, founding a lifestyle magazine aimed at Gen X called Swing in the ‘90s.

Swing only lasted a few years, folding in 1998. It doesn’t even merit a Wikipedia entry. So perhaps it’s not surprising that David joined his father’s company a couple years later.

Even then, he wasn’t directly involved in the fashion design side of things like his father. His role was overseeing development of the company’s website into a proper e-commerce platform. And he was rather forward-looking. He had a whole section of the website dedicated to video — called RLTV — featuring not just runway shows but interviews with brand-friendly celebrities like Sheryl Crow and André 3000. He called this content “merchan-tainment.”

After the movie Minority Report came out, David developed the idea of turning a window at one of the flagship stores into a giant transparent touchscreen that could be used to shop merchandise without entering the store. It was a bit gimmicky, but creative use of technology for a brand whose marketing leans heavily on tradition.

At some point, David became the head of advertising, which is the department I fell under. He scheduled one-on-one meetings with every single person in the department. He wanted to know who you were, what you did, and what problems and pain points you had in how the department worked. That has always stuck with me as a good example of a manager showing interest in understanding how his team operates. From where I sat, he ended up being pretty good in his new role.

So, yeah. I generally liked David but I didn’t know him well. Just a little better than I knew his father.

All of this brings me to the point of the story: the time I loaned a billionaire $20. At the time of this incident, Ralph’s personal worth was reported to be around $4 billion. Admittedly, I don’t actually know what David’s personal worth was. But for the sake of a sensational title, I’m going to just assume that the father’s worth would be bestowed to the children and say that David was also a billionaire.

I was standing outside RL headquarters at 650 Madison trying to hail a cab. Finally a taxi pulled up and David Lauren got out. He saw me and he said, “David. I have no cash on me to pay the cab driver. Do you have twenty dollars I can borrow?”

This was in the days before taxis accepted credit cards.

I was a bit flummoxed. I mean, yeah, I had twenty dollars, but would I ever see it again? And can I say no to the eponymous CEO’s son, who also heads my department?

So I pulled twenty dollars out of my wallet and handed it over, pretty sure I would never get it back.

The next day, I was in my office and I got a phone call. It was David’s assistant. She sounded very confused.

“Hi, this is David Lauren’s assistant. David asked me to call you. Um, he says he owes you twenty dollars?”

I was impressed! “Yes. Yes, he does. He does owe me twenty dollars.”

“Huh. Okay. I’ll send it over.”

About a half hour later, a bike messenger showed up with my twenty dollars. The bike messenger probably cost more than that.

That’s where the story ends. But now as I write this, I can’t help wonder if David asked his assistant if she had twenty dollars she could send me, with a promise to pay her back.

Building A Better Pizza Box

The 25th inventor in my series was William Walsh, inventor of the GreenBox pizza box.

The GreenBox pizza box is perforated. The top breaks apart into four plates, and the bottom folds down into a small container to more easily store leftovers in the fridge. I first saw William in a video that went viral in 2009 demonstrating how the pizza box works:

I reached out to William, and photographed him at a pizzeria (naturally) and then later interviewed him in his tiny office. A lot of the entrepreneur inventors in my project were destined for failure, but William’s company was getting a lot of attention and seemed to be on the rise.

I was surprised to hear, just two years later, that William died suddenly at the age of 44. I wondered what was going to happen to the company. The pizza boxes were inspired by a practice he used to do in college, tearing a pizza box apart to make plates for everyone, and he was the passionate driver of the business. It seemed personal to him. But as it turned out, his business partners were determined to continue.

In 2014, the company went on Shark Tank and received a $300,000 investment from Kevin O’Leary.

Last year, GreenBox was acquired by the largest privately held 100% recycled paper and packaging company in the world. And if you look for them, you’ll start to notice GreenBox boxes everywhere.

Okay, now I’m hungry. Time to get some pizza. Thanks for reading the newsletter. Pass it on!

Until next week.

David