The Exchanges

Q working on now, the Modern Elder Academy. I actually want to start with the middle chapter. I'm going to talk about Airbnb, where we got to work together. Let's paint a picture of just what it was like for you to join Airbnb in your fifties, uh, surrounded by a bunch of twenty-something, thirty-somethings reporting to Brian Chesky, who is, I don't know, in his thirties. What was that like?

A So yeah, I, I wasn't planning on doing this. I, I got a call, uh, from a woman named Natalie Tucci who worked at Airbnb and said, Brian Chesky and I've been talking about having you come in and give a talk. Are you open to that? And I was like, well, what is Airbnb? This was, uh, 13 years ago. This was, I think it was the end of 2012. And then Brian called me and said, listen, we really want you to come in. And so I came in and gave a talk about innovation and hospitality. And, and I think I didn't realize it was sort of a, a dress rehearsal for Brian to sort of see whether the younger crowd there, um, I was 52, the average age was 26. Would, you know, feel good about, you know, uh, an old geezer like me with a bricks and mortar boutique hotel background, uh, talking about the industry that Airbnb was disrupting. Um, and as it turns out, people liked me. And, uh, so, uh, Brian said, I want you to come in for and work 15 hours a week, uh, as a consultant, I want you to be my in-house mentor for both me and Joe and, and Nate and. And I said, okay, you know, 15 hours a week is great. And then, uh, within three weeks, it was 15 hours a day. And Brian, and I was saying to Brian, you know, you're actually not paying me anything. Um, they gave me a little bit of stock that would, would invest in six months. And I said, like, I don't know that this deal is working for me. Um, this is y…

AI assessment note: “I was 52, the average age was 26. Would, you know, feel good about”

Q is a thing. Every founder is just like, I'm the founder. You gotta do what I tell you. It's founder mode. We're getting, this is how we win. We're in founder mode. You shared really good insight of building credibility. As a really good lever to work better with someone like that. Is there anything else you just think as, uh, tactics to be effective with founders and founder mode?

A So if I knowing what I know now, I would say Lenny, let's, let's do a little pep talk you and me before the meeting. I want you to start the meeting with the following, uh, as you present and Brian's in the room. So Brian, let's talk about what we're trying to accomplish here. Let's get really clear. And you probably did this, but let's get really clear on what, um, both what's the intention of this iteration that we're doing on the product, like what defines success and what do I want to get accomplished in this meeting? And you start with that because that actually helps to make sure there's alignment. And frankly, if there's not alignment, You might as well not have the meeting. Let's spend the rest of this meeting talking about alignment. That's what I would do because that's something you can come back to over and over again during the rest of the meeting. When Brian or the founder, whomever it is, is beating you up on something and saying like, well, let me tell you why it looks like that or why we're doing that. It goes back to that, you know, the three principles or the three key goals we're trying to do with this product update. And, um, Yeah. So, so try to set alignment on the front end.

AI assessment note: “try to set alignment on the front end”

Q Nailed it. Okay. I'm gonna zoom out and take us to a recurring segment on this podcast. I want to see if this goes anywhere. AI Corner. And with AI Corner, ask us just what's a way that you've found AI useful in your work or in your life? Any kind of trick you've learned, any workflow, anything you found useful?

A Yeah. You know, I, I have a daily blog and it's called Wisdom Well, and it's on the MEA website. And, um, when I'm looking for inspiration, You know, AI does it for me. And ultimately it gives me a first draft and that's good enough for me then to say like, okay, because there's times when I'm like missing the inspiration. I tend to write really well in the morning. If it's any other time of the day, I do not like writing creatively. Um, so if I have a deadline for tomorrow and it's five o'clock in the afternoon, it's like, okay, chat GBT, I'm on my way to you. And I tend to use chat GBT the most because I don't know. I mean, I like Claude as well, but, um, Yeah.

AI assessment note: “when I'm looking for inspiration, You know, AI does it for me.”

Q No big deal. So I don't know if you know this, I got married at Burning Man. We had an unofficial wedding there on bicycles. So it's really meaningful to us. I've been there four or five times. Uh, what's something about Burning Man that maybe people don't know some insight story or a really unexpected piece of the, the journey? I imagine there's a lot, but what comes to.

A I would say the best. Not well known thing about Burning Man is that Burning Man owns a place called Fly Ranch. And Fly Ranch is about 10 miles from Burning Man. Now, if, when you go to the burn, uh, the event in, you know, around Labor Day, uh, you cannot go over there. It's, it's, it's locked off. It's 3400 acres. But if you do, if you look at Fly Ranch, um, flyranch.org, I think it might even be Or it's on the Burning Man site. Fly Ranch is like the opposite of Burning Man. Burning Man is this alkaline desert. Like there's no, no living life there at all. It's very masculine. Fly Ranch is like porous and like, like lots of like desert grasses and hot springs and hot pools and it, and birds and wild horses. And it's one of my favorite hot springs places in the world. Um, so just check it out and you can go there. When it's not during the event, and, and it's quite beautiful.

AI assessment note: “the best. Not well known thing about Burning Man is that Burning Man owns a place called Fly Ranch.”

Q want to go to the flip side of companies looking to hire. Feels like there's this, uh, untapped supply of awesome people that companies with ageism in tech, uh, aren't finding and hiring. So to help hiring managers and companies take advantage of this, what's something you suggest they do? How do they shift their mindset or maybe shift the way they hire that might help them find these people?

A I think we're moving into, there's a, there's a book that David Epstein wrote called Range, and the whole premise of Range is that we're moving out of the era of the specialists and into the era of the generalists, and I think AI is just accelerating this. Um, As we are more reliant upon AI and AI can, can be exceptional at technical skills and solutions really expeditiously. I think generalists, people who can think broadly become all the more important. And I think that what I would say to someone in HR. Or recruiting, uh, is beyond what I already said before is, is the person passionate? Are they curious? Are they a learner? Um, do they have good energy? But I would also say, are they a generalist when they're a problem solver? Because I actually think that's going to be an increasingly important part of how effective companies think broadly. So I think that's a key one. I think also this idea of how do you create intergenerational collaboration in the form of mutual mentorships? Um, one of the things I, I loved at Airbnb that there are a few people I did this with where I had something to teach them and they had something to teach me. So, um, good example, my iPhone. So there's 97% of the utility of my iPhone that I probably don't use and don't know How to use this is, you know, back in, let's say, 2013, 2014. And so there are people in who knew iPhone or Google suites back…

AI assessment note: “how do you create intergenerational collaboration in the form of mutual mentorships?”

Q There's a couple threads here I want to actually follow. So this point you made about shifting your mindset to aging is a positive thing makes you, helps you live longer. That's such a powerful point. Can you just speak more to that? Just what does that look like?

A Yeah. There's a couple, there's lots of data points. I'm just gonna, I'll talk about two. One is this Becca Levy study, which has been going on for 15 to 20 years. If you sort of take, buy into the ageism of American society, Or Hallmark cards when you get a, a, a card at age, 40, 50 or beyond. There's a belief that life gets worse as you get older. And, um, and if you can survive your midlife crisis, all you have to look forward to is disease, decrepitude and death. And the bottom line is, uh, you know, there's a lot of things that get better with age. I wrote a book called learning to love midlife. The subtitle says it all, 12 reasons why life gets better with age. And what I really wanted to do with that book, which is really, it summarizes the MEA curriculum. I wanted to write a book that sort of helped people to see the upside of aging, the unexpected pleasures of aging. Uh, so they had a pro-aging, not just an anti-aging point of view, because when you actually have a pro-aging point of view and you see that the upside of aging, You take better care of yourself, both your mind and your body. You actually are willing to learn and try new things. One of my favorite MEA questions is, 10 years from now, what will you regret if you don't learn it or do it now? It's a powerful question. Really important question as we get older, when you're young, you know, you've got all, you …

AI assessment note: “when you actually have a pro-aging point of view... You take better care of yourself”