This Week in Startups - The power of super communication with Charles Duhigg | E1938

Episode Date: April 26, 2024

This Week in Startups is brought to you by… LinkedIn Jobs. A business is only as strong as its people, and every hire matters. Go to https://www.linkedin.com/twist to post your first job for free. Terms and conditions apply. Mantle. The AI-powered equity management platform designed for modern founders and operators. Get your first 12 months free at https://www.withmantle.com/twist HubSpot. If you’re fundraising, be sure to check out the Million Dollar pitch competition from Hubspot for Startups & HubSpot Ventures. Apply now at https://www.hubspot.com/milliondollarpitch * Todays show: Pulitzer Prize-winning journalist Charles Duhigg joins Jason to discuss the different types of conversations (9:29), the role of humor (22:48), and they way conversation dynamics can shift (49:30). * Timestamps (0:00) Charles Duhigg joins Jason to break down his latest publishing, Supercommunicators (4:01) The importance of communication in startups and lessons from "The Power of Habit” (8:06) LinkedIn Jobs - Post your first job for free at https://www.linkedin.com/twist (9:29) The role of communication in organizations and the different types of conversations (21:30) Mantle - Get your first 12 months free at https://withmantle.com/twist (22:48) Exploring the role of humor, laughter, and vulnerability in conversations (30:06) Understanding gender and cultural differences in communication (39:23) HubSpot - Be sure to check out the Million Dollar pitch competition from Hubspot for Startups & HubSpot Ventures. Apply now at ⁠https://www.hubspot.com/milliondollarpitch (40:34) The role anecdotes have in conversation (49:30) How the dynamic of the conversation shifts when someone has an ask (1:01:35) The Harvard Study of Adult Development (1:06:36) Closing remarks * Check out Supercommunicators: https://www.charlesduhigg.com/supercommunicators * Follow Charles: X: https://twitter.com/cduhigg LinkedIn: https://www.linkedin.com/in/charlesduhigg/ * Follow Jason: X: https://twitter.com/Jason LinkedIn: https://www.linkedin.com/in/jasoncalacanis * Subscribe to This Week in Startups on Apple: https://rb.gy/v19fcp * Thank you to our partners: (8:06) LinkedIn Jobs - Post your first job for free at https://www.linkedin.com/twist (21:30) Mantle - Get your first 12 months free at https://www.withmantle.com/twist (39:23) HubSpot - Be sure to check out Hubspot for Startups & HubSpot Ventures for their Million Dollar pitch competition. Apply now at https://www.hubspot.com/milliondollarpitch * Great 2023 interviews: Steve Huffman, Brian Chesky, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland * Check out Jason’s suite of newsletters: https://substack.com/@calacanis * Follow TWiST: Substack: https://twistartups.substack.com Twitter: https://twitter.com/TWiStartups YouTube: https://www.youtube.com/thisweekin Instagram: https://www.instagram.com/thisweekinstartups TikTok: https://www.tiktok.com/@thisweekinstartups * Subscribe to the Founder University Podcast: https://www.founder.university/podcast * Founder University: Cohort 8 begins May 9th. Apply here: https://www.founder.university

How about you? What's the most embarrassing thing you can remember? Everybody's flying out from L.A. to Sundays. But I said, you know what, guys? I'm going to meet you there. I get on the flight. I got a middle seat. I go.

I'm exhausted. My friends are already there, private jet, blah, blah, blah. Put my bag up. I sit down in my middle seat. And I feel a weird sensation, like a crunching sound. Then I feel wetness. And then I feel heat. And then I jump up and I look down.

And there is a giant Starbucks cup and black coffee steaming in my seat. Oh my God. And the woman in the window seat looks at me and goes, oh, were you sitting there? And I said, where your coffee was in my seat? And then I feel my ass is on fire. But the plane is taxying like now at this point. I run to the bathroom. I drop my draws.

I see out of the corner of my eye. my pasty white Irish ass is red. This is hot coffee ass is the name of this story. This Weekend Startups is brought to you by LinkedIn Jobs. A business is only as strong as its people and every hire matters. Go to LinkedIn.com slash twist to post your first job for free. Terms and conditions apply. Mantle.

The AI-powered equity management platform designed. for modern founders and operators. Get your first 12 months free at withmantle.com slash twist and HubSpot. If you're fundraising, be sure to check out the million dollar pitch competition from HubSpot for startups and HubSpot Ventures. Apply now at HubSpot.com slash million dollar pitch. All right, everybody, welcome to this week in startups. We've got a delightful guest back on the show Charles Doe Higg is here. you of course know him.

He's a writer at The New Yorker. He's got a new bookout Super Communicators. And his first book, he came on episode 7.51 of this week and startups a lifetime ago for the power of habit, right? That was the book we talked about back then. Yeah. Yeah, a while ago. How many, welcome back to the show. How many copies of that book sell?

That's got to be a million seller. Hundreds of thousands? Oh, yeah, no. It's like, I think it's like 12 million across. 12 mil. Yeah. Yeah. No, I've been very, very lucky.

It's been great. So you return in that case, you return the advance. Yes. It never happened in books. Yes. No, I was, I was, yeah, no, it was great. It was great. It's really, I'm very lucky to have had that happen.

And even bet more, like, I think the fact that that many, I'm sure you've experienced this as well, that when you, when you're lucky enough to sell that many copies, you just hear from a lot of readers who say things like, look, I found this. at exactly the right time in my life. I'd been drinking for years, and this helps me figure out how to get to AA and change my habits. And that's always, like, super satisfying and rewarding. And that was, it got picked up in the, in the startup and the business community in a major way,

because in the world I live in startups, people are addicted to efficiency. And if a book comes out about efficiency or communications, that's our wheelhouse. And so you've got a big audience, I think, in the startup community, yeah? Yeah, no, absolutely. That's actually one of the reasons I wrote about, I wanted to write about communication for super communicators is because, I was hearing from a lot of startup folks. I was hearing from a lot of managers saying, you know, I have an MBA from Harvard Business School. Like, I would hear from a lot of my classmates that would say, like, look, technical skills are no longer valuable to us. What makes all the difference is our ability

to communicate with other people. Because no matter how good an engineer you are, if you cannot communicate and manage other engineers, it doesn't matter. Yeah. 100,000, 100% communication is the wheelhouse. And when you look back on the power of habit, the core thing to take away from that is the systems you set up, the process is more important than your goals or your hopes and dreams and aspirations, correct? If I'm summarizing correctly. That's exactly right.

That's exactly right. That if you pay attention to these cues and these rewards in your environment, your habits almost change automatically. Yes. And so, and, and it, but it does mean focusing on those things that oftentimes it's easier for us not to focus on, right? Like, like, we get into the habit of having the same thing for lunch every day. We get into the habit of either exercising or not exercising. And it, and it can feel very pedantic to focus on these small things.

Yeah. And yet, you know, it doesn't matter what you eat today, but it does matter what you eat every single day. Yes. Yeah. And this is where, you know, if you want to eat healthier, you have to create the systems process by which this will happen. I did this. I just thought my housekeeper how to make a French omel

because it happens to be one of my favorite things to eat for breakfast, if not the favorite thing. And I just tell her, you know what? Just put it outside my office. It's three or four eggs. If I happen to skip it that day, it's not the end of the world. I give it to the dogs.

It's three eggs. But I don't go look in the refrigerator for food, for breakfast food. I just get those three eggs. Exactly. Exactly. And we actually have a bunch of apples. Like I love apples. And I find that as long as I have enough apples around me, I will never eat anything on health. Right? Because you're just, you're looking for something. You're in the flow. You're doing work. You're thinking about stuff. You don't, you don't want to interrupt that with having to make a decision. And so just make it easy to do the right thing. You know, I took a lot from the book in my venture capital firm.

So as but one example of this, I just said, you know, our business is based on how many founders we meet with. And then our decision-making process. And there's another book, Super Forecasters. I don't know if you know that, but... Yeah, yeah. Basically, the premise there is record how you make a decision

so you can make better decisions in the future. That's exactly right. It would be the equivalent of like, videotape Steph Curry shooting threes in a game, play the video back, and you can learn something from it, or Draymond Green,

setting screens, you get the idea. So I just went on a systems process inside my venture firm and said, how many applications for funding can we get, how detailed can those,

how many questions can we get founders to answer, and then how many of them can we meet with over Zoom? And sure enough, we, and then how do we qualify to make a decision-making process?

And what I found was, I'm now seeing many more of the highly qualified startups and founders that I want to meet with because I built a system to do it, not just a random, you know, I'm going to try to do more meetings today. I'm going to try to do more meetings this week. I hired, you know, three or four frontline people to just do the first meeting with these founders and qualify them across a couple of actually 13 variables. And so that's the system or process I set up. And then, you know, the outcomes take care of themselves if you eat the apple, you eat the omel.

That's exactly right. And what's interesting to me is that, so there are these things that we can assign metrics very easily, right? Like how many meetings are we taking? How many are we getting to the next step? How many are we investing in? And I think that's really, really useful and really important. But there are also a set of soft skills that we can systematize where the metrics are harder. And so as a result, what we tend to do is, and again, conversation is a great example of this, right?

We tend to rely on our impressions. Like, was it a good conversation? Was that not a good conversation? Did I get across what I wanted? do I understand them? And in many ways, when we press to squeeze that to give us a metric or to give us more information is when we start to learn. Because our own intuitions have to be trained against something objective, right?

Otherwise, we think that we're a genius. Hey, founders, hey startups. When you're hiring for your small business, you want to find quality of professionals who are right for the role. But I understand it can be tough to find the time and resources to find that perfect hire. That's why you want to check out? You guessed it, LinkedIn Jobs. LinkedIn Jobs gives you the tools to find the right professionals for your team faster and for free.

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pause right now and just go over to Audible and buy it or buy it over at Amazon or your local bookstore, whatever your jam is. We'll be here when you come back from the pause, super communicators. And if you have a ripower habit, buy both. Okay, got the plug out of the way. I love both of these books. So that's all you need to know. Go buy it. Books are the greatest deal ever, by the way. I just want to give a shout out. They really are. Oh my gosh. Man, how many years you suffer for this book? Tell me, it's three years. I spent three years writing this book. And I think about this all the time. I'll go buy a book for like $12.15. Yeah. And I'll read it in a day and a half. And I'm like, oh man, that author spent four or five years writing this novel. And I just, it's a great.

It's the arbitrage there. Value for dollar is ridiculous in books. Because also, you can give the book away then to somebody. And you tell them like, hey, I got a lot out of this book. And you give it to somebody. Now you get all that goodwill or you sell it, resell it for six or seven bucks. Now you're down to paying six bucks for six hours of listening or six hours of reading. It's a dollar an hour pack with knowledge. I mean, shout out to books that are high quality. And I mean, I've only written one and I'm working on two now. It is just such a large amount of work to get this. And you took the approach of finding people who studied the history of communications and who were some of the best communicators in the world. Turns out, the job I would. The job I

was going to go for. Little known fact, I was going to go in the police force, New York City police, uh, at a high school. But then I decided I wanted to be an FBI agent. So I was going to go to John Jay criminal justice and get my master's in psychology and forensic psychology. I wound up getting into the internet and I went the different direction. But FBI agents turn out to be super communicators. Um, so let's talk about, uh, you can take it either way you want, the type of conversations we have, or maybe a bit about what you learned about the history of people getting really good at communications and conversations. Yeah, absolutely.

And it's not just FBI agents, right? There's this great story about Felix Segalo, this FBI agent who is kind of a super negotiator. But it's also the CIA. One of my favorite stories is about this guy, Jim Lawler, who's a CIA officer. And when he goes to the farm to do his training, what he realizes is that it's basically a communication school, right? your job in the CIA is to communicate with other people in a way that you can create trust and empathy and that you might bring them something and say, hey, look, we're hearing this out of

Syria. Can you tell me if it's true or not? Right. It's basically a communications job. And so he goes and he does the training and then they send him over to Europe. And it turns out he is terrible, terrible recruiting spies. Like literally so bad that he'll go to parties and he'll start chatting someone up and they're like, I think you're trying to recruit me for the CIA.

If you don't stop right now, I'm going to report you to. the authorities and get you deported. And he's just, and so like, and he had wanted his whole life to be at CIA officer. He'd worked so hard to get this job. And eventually he meets this one woman, um, uh, Yasmin, who is from a Middle Eastern nation. She works in the foreign, the foreign minister's office and she's in town in Europe, where they all are. And he takes her to lunch and he gets to know her and he asks her like, would you consider

working for the CIA? And she just freaks out and says, absolutely not. And he tells his bosses and his bosses are like, you're going to get fired. Like, you're terrible at this job. Like, you've been here a year. You've recruited no one. And so he calls up, he asks me and he's like, well, you have one more dinner with me. And she says, yes.

And he goes and he has dinner with her and she's super glum. And he keeps trying to cheer up. And it's not working, right? And then at some point, he just gives up and he's like, look, this isn't going to happen. And he just starts being honest with her. He starts telling her about how disappointed he is in himself and how frustrated he is, that he's not good at this job. And that's when for the first time she could hear him and she says,

I want to help. I can do this. And she becomes the best asset in the Middle East over the next 20 years. And okay, so if we read into that interaction, there's a little bit of vulnerability. There's a little bit of pacing. So I happen to know a little bit about this from my psychology background and as

from being a journalist. Because as a journalist, our jobs like FBI agents or an interviewer on a podcast, is to get information out of the host. the subject, make them feel comfortable and even pace them, which I'm doing right now with you in this interview, trying to pace your level of energy. And I always tell people like, the person's slow, slow down. If the person's fast, go fast. So maybe you can talk about what the CIA FBI learned about vulnerability sharing, empathy, deep listening. There's a lot there

and pacing. There's a ton of skills. Yeah. And super communicators, the book, is really about these skills, right? Because what we... we know is that no one is born a great communicator. There's no personality type that makes you great communicator. She's a series of skills that you can practice and make into habits. And so one of the first things that happened when we look at that Jim Lawler, that CIA example, is you're exactly right. One of the things he did is match her. He matched. He matched this woman. She was feeling glum, and so he let himself match her emotional state. And what's interesting about this is that when researchers have looked at communication and we're kind of living

through this golden age of understanding the neurology of communication, they found that we tend to think of a discussion as being about whatever we're talking about, about one thing, right? But actually, every conversation is made, every discussion is made up of different kinds of conversations. And those kinds of conversations, they tend to fall in one of three buckets. There's these practical conversations when we're solving problems or making plans. Punchless conversation, right? Exactly.

Exactly. And then there's emotional conversations. where I might tell you how I'm feeling, and I don't want you to solve my feelings. I want you to empathize. And then finally, there's social conversations, which is about how we relate to each other and how we relate to society. And what I think Jim Lawler, the CIA officer, recognized during that meal, is she was feeling down and he was trying to solve her problem. She was in an emotional mindset, having an emotional conversation. And he was being super practical.

He was like, oh, no, you don't have to be worried. like let's just, you know, let's feel good. Let's remember all the places we went together. Yeah. And it's only when he matched her and he got emotional himself that they were able to hear each other. And within psychology, as you know, this is called the matching principle, that you have to have the same kind of conversation at the same moment to connect.

Yeah. And this is where connection's happening. We have these mirror neurons. There's a whole physiology to this. Absolutely. But all you really need to know is that as humans, primates, we mirror each other, we imitate each other and when we're in sync in some way, a connection is formed. When we experiencing things together, this is why, like, you can fall in love with, you know, there's

this hero syndrome, like the EMT who saves you or the firefighter who saves you from like the fire burning building, they fall in love kind of thing. It's a super intense moment in time you connect on a very high level, but it happens actually in every conversation. And every conversation is this moment to either deepen a relationship or to damage a relationship. That's exactly right. And it's known within neuroscience, it's known as neural entrainment. And what's interesting is that now what we can see is we can actually watch people's brains when they're having conversation.

And we can see that as people connect, they actually start to think alike. Their neural activity becomes more and more similar. Yes. Which actually makes sense when you think about it. Because if I tell you about something I'm feeling, you actually experience that emotion a little bit, right? Or I tell you about an idea, you experience that idea. Our brains are becoming entrained.

And the goal of a conversation is, you actually, you actually experience. is to achieve that entrainment because we are hardwired to feel closer to each other and we're trusting of each other. We're hardwired to feel happier when we achieve that entrainment. Because we're social animals. This is why we went to the top of the food chain and the species has done so well. We have this incredible desire need to connect and the way we do it is through conversation. So, okay, sometimes you and your spouse, you and your team at work, or you and a friend have a task list of things you got to get done. You've got to get the house clean.

You know, you've got college applications done. You're planning a trip with your friends. Whatever it is at work, you're going through whatever project X is. Then you have emotional conversations. Hey, you and I, we became friends and we're both Gen Xers and you're struggling with something with your kids, your teenagers, I'm struggling with one. And we rely on each other. We have this emotional conversation.

But I don't want you to solve my kids' problems. I just want you to put your hand on my shoulder and say, yeah. Exactly. Yeah. And acknowledge what you're. feeling, right? Be like, look, it's hard. It is hard to be a parent. You're going through like something that's tough and like, you're doing great, but like it's just hard, right? That feels so good. Yeah, what's the next one? You said there is your three times? The social,

the social, which is about, which is about how we relate to each other in the context of society, right? Like so, so, so it's, and not every conversation, every discussion usually has a practical in an emotional part. Not every single one has a social part, but actually there's a lot that do that we don't realize it. So if we're talking, for instance, about, if we're gossiping, about someone who's not here, right? Yeah. Malcolm Gladwell. Let's talk about Malcolm Gladwell.

Oh, that guy. Right, exactly. Malcolm. Look at him. He's doing blue apron commercials now. He's talking about blue apron on his podcast. Come on, Malcolm. Hey, man.

We know you're not doing a blue apron. You got to pay the bills. I know. When I said Malcolm Gladwell do a blue apron commercials, I was like, I love it. Podcasts are killing journalism. Yeah, that's exactly right. I mean, just think about what happened to our profession. I convince Sam Harris to do a podcast.

like years ago and my book agent, Brockman was like, what have you done? He hasn't, he won't submit a book. He's making too much money from this goddamn podcast. I was like,

Sam, the world needs you to publish a book. Stop with the goddamn podcasting. These are good problems to have. I mean, it's a high class problem. So when you're talking about Sam or when you're talking about like,

like how do we think about this issue? We talk about society all the time, right? Like you and I, we both live in the Bay Area. And when we talk about San Francisco, right? And the problems that San Francisco has, I'm also, I'm still kind of bullish on San Francisco because I just love it, the

city so much. Like, that's actually a social conversation because one of the things we're talking about is how our, how our perceptions are a little bit different. And the goal is not to convince each other, right? I don't want to convince you that I'm right and you convince me, but to share that, to acknowledge those differences and learn something from it, that's often a social

conversation. Got it. Not a debate where somebody has to win. No. And in fact, A good conversation is never a debate, right? Or very infrequently. Like, the goal of a conversation is not to convince the other person that I'm right and you're wrong or I'm smart and you're dumb or you should like me or you should respect me. The goal of the conversation is just to understand how you see the world a little bit, to speak in such a way that you can understand how I see the world.

If we've done that, we have succeeded. And the way to do that is to show people you're listening and to ask a follow-up question. That's exactly right. That's for me, without knowing how you rank them in the book, to be able to have the person feel like you've truly deeply listened to what they said. Yes. And then to ask a follow-up question. And this, which I do as an interviewer and I do it with friends or whatever, I will just repeat back to them something they said. And then I think, what is the most for the audience, I think?

What is the question the audience most wants to hear the answer to or that I can come up with a question. that they would be really interested in the answer. So it's either their question or it's my question, but they get some great value out of it. Yeah. And so in this case, I'm doing that right now. Look, business leaders face a maze of tasks today. We all know that creating and managing your company's ownership shouldn't add to your stress.

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That's withmantle.com slash twist for your first 12 months free. See why hundreds of founders are switching to Mantle right now. in a social situation, what is the role of humor, laughter, and joking? And there's different types of joking, obviously. But I'm curious,

where in these communications and these styles of conversations does the act of laughing about life and humor play a role? Because it's huge. It's kind of my superpower, people tell me, is that I make the conversations

is funny and I drop a joke in once or a while and I get invited back to more dinner parties. Once in a while, I get too far. I don't get invited back. We got to do some damage control, but I was wondering if you could tell me a little bit about the role of humor in all of this. Absolutely. And you're exactly right that proving that we're listening and asking questions and asking the right kinds of questions, and we can dig deeper into both of those because

there's a lot of science about how to do that, how to do that better and how to do it right. But to answer your question about humor, so one of the things we know, there's a guy named a researcher named Provine, who used to be at the University of Rhode Island, he's now passed away. He spent his whole career basically studying laughter. And one of the things that he discovered is that 80% of the time in conversations, when we laugh, it is not in response to something funny. Right. Both of us have laughed, and this gets to your superpower, is that both of us have laughed in this conversation. Neither of us have told a joke. No, we're not doing, this is not a, we're not in the cat skills right now. I might take my life. Exactly. Exactly. And

And so what's happening when we laugh? When we laugh, we're showing the other person that we want to connect with them. And when they laugh back, they're showing us that they want to return it, that they want to connect back. And that's neural entrainment is the fancy word for this. Exactly. Exactly. And so what's interesting is my guess is a lot of those times at those dinner parties, what you're doing is you're bringing levity to the conversation by laughing about something. Yes.

That someone else might say the same thing or hear the same thing and not like, but you're bringing this levity, you're showing everyone, hey, I want to connect with you. And then they laugh back and we all feel connected to each other. And that's really important. Now, if you actually tell a joke and it's genuinely funny, that's even better, right? Sure, absolutely. Or anecdotes. I mean, I think, you know, when I think about techniques, there are devices you and I use as

writers, you're a much more successful round than I am. But you, to your admissions suck at communications. You said the reason you wrote the book is because your conversations, suck and are falling flat in your life and in your business life. They totally were. They totally were. And that's exactly why I wrote the book. How could this is perplexing to me?

I'm going to ask a question on my behalf. How could somebody be a transcendent, top 0.1% writer and be horrible at communicating in person with words. You're good at words. You know a lot of journalists and you were a journalist and still are kind of a journalist. So you know that to answer that question. I know the answer to the question, but I'm going to ask it. A lot of journalists are terrible at it.

Right. So I found, what I think it was was that I was overconfident. So I was at working at the New York Times and they made me a manager. And I was really good at like strategy and planning and stuff like that. But then people who are working with me would come and talk to me about problems. And I would, instead of hearing them as emotional conversations, I would try and solve their problem right away. And they would get way disgruntled, right? Or they would bring to me something that was practical.

And I would think that they were just complaining about like some emotional thing. And then the same thing happened at home, right? I'd come home from work after a long day. I'd complain to my wife about my day. She would offer me some good advice. Like, why don't you take your boss out to lunch and get to know him better? And instead of being able to hear what she was saying, I would get even more upset. And then she would get upset because I was upset with her good advice.

And it's because we weren't having the same kind of conversations at the same moment. Right. Once we learn. And there's a couple of techniques for this. So one of them is asking questions. You brought this up, and this is a great one. Super communicators asked 10 to 20 times as many questions as the average person. And many of the questions they ask are a special kind of question that's known as a deep question,

which asks about our values or our beliefs or experiences, which can sound kind of intimidating. But it's as simple as if you meet someone who's a doctor instead of saying, where do you practice medicine, asking something like, what made you decide to go to medical school? What do you love about practicing medicine? Was there something in your childhood that led you to not be good at communication? Sorry. That is definitely a deep question. That is a deep question.

But putting it aside, I could, yeah, I could see, I think I know the issue that you were also, you had a blind side. And I see this with a lot of people who go to a certain, get a master's degree from a certain university with certain initials. HBS. You went to HBS. Now, for people who don't know, Harvard Business School is absurdly hard to get into. They accept people. You graduated 2000 or something? 2003.

Okay. I dated somebody who went to HBO. I hung out with HBOers. I've spoken there three or four times. This is the most confident, competitive, problem-solving group of lunatics on the planet. It's like taking the smartest kid. class who answers the question before the teacher finishes it and doesn't raise their hand, and then putting them all in the same building and then telling them, you're going to change the

world. And I went to- And by the way, whoever answers the question fastest is going to get super-duper rich. So you should definitely practice answering it as fast as you can. Correct. Whoever figures out general AI, whether it's Sam Altman or Elon, you know, or somebody else, they're going to win a big prize. So you were part of the fast problem-solving group.

the problem is you went into a group of people who don't um that's not how they saw problem they saw problems by discussing it meditating on it and brick by brick bird by bird you know building a mental framework and then they don't have the courage just go right to the answer it's as if you were a chess player with a 1600 rating playing with somebody who's learning the pieces you know or is an 800 rating you're just going way too fast for them And then that makes them feel small. You made those people feel like they weren't smart. And that sucks when your manager does that.

Is that what happened? I think that was an aspect of it. But I actually think the bigger thing is that it's like someone bringing you a checkers board or a backgammon board and insisting that we play chess. Where they would bring me a problem, an emotional problem. And I kept on insisting that it could be solved practically. And it just can't. That's what happens with my wife, right? Like when we get into this thing with her, when she mentions something that she's feeling to me and I try and solve her feelings, oh, you shouldn't feel that way or here's what you can do.

Yep. It's not so much that she feels little or scared. It's that she feels like, I'm actually not listening to her. And she wants to play backgammon. And I'm like, nope, we only play chess in this family. That's all we're going to do. And that's frustrating. Right.

There was a book. Men are from Mars, women are from Venus or something. Let's get into it. Let's talk about gender differences. You do this massive research, and we won't say these are our personal opinions. As far as we're going, we have no opinion on gender and communication differences. But what are the experts say? You and I've been married and have kids, and we have our own thoughts on gender differences.

I'll tell you what actually the data says. What is the data say? Yeah. So what the data says is that there's actually very few differences in how genders communicate, with a couple of exceptions. The first of which is, what do you feel comfortable in? So everybody has this need, everybody has this craving for neural entrainment. Everybody has deep questions proving that we're listening.

That works with everyone. But then the question is, from a cultural perspective, where are you comfortable? Where are you habituated? And for many men, we get habituated into practical conversations, right, into problem solving. Got it. And for a number of women, again, they get habituated. It's more acceptable or it's pressed on them to be more comfortable having emotional conversations. And so when we say men are from Mars, women are from Venus, it's actually not true.

It's that everyone's from Earth, but men might spend more time on Mars and women might spend more time on Venus. But that doesn't mean it's something about our brains. It doesn't mean it's part of our character. It means simply that we've been inculcated with it. The same thing is true across different cultures. So if you were to go to, you know, there's a question that I ask whenever I give speeches, which is turn to the person next to you and describe the ask and answer the last time you cried in front of another person. And people love this exercise. It's a famous exercise by this guy, Nicholas Epple at University of Chicago. In Asia, in Japan, that does not work. Like, people are not comfortable talking about the last time they cried. They are comfortable talking about the last time they saw their parent cry. Whereas in the U.S., that actually might feel. kind of like a betrayal, right? Yeah.

Yeah. And so that doesn't mean that like we have a different tolerance for intimacy. It means that these cultures teach us different norms. And part of being a good communicator is just recognizing those norms, just recognizing this is the norm I'm steeped in. This is the norm you're steeped in. But we're not bound by them. Fascinating.

So, and I wonder, because I've heard this from some enlightened friends of mine who've had long lasting marriages, is that. The style difference that we're referring to here, men are sent to Mars, women are sent to Venus, but we both could go to either planet, which just maybe society pushes us there in America. Now we're forced to be constantly in problem-solving mode as men. And women are being told or pushed into or subtly navigated towards emotional or conversations with more resonance. You put those two things together.

Those are the exact polar opposite conversations. The techniques that work in one, the styles that work in one, and the goals of each of those is completely different. As you've just explained, the goal of the emotional one, I think, is to feel heard, to know you're not alone and to experience in this, you know, mirroring, et cetera. The goal of the punch list one is to feel like you made forward progress. And that one, I guess, being shorter would be better. And for the emotional one, longer would be better.

Is the duration of the conversation matter? No, it really doesn't. Because if you think about it, like, I'm sure you, in your VC firm, you guys have practical conversations that go on for weeks, right? Should we make this investment? Should we not? Like, that's not, and there might be some emotional aspects to it, but it's primarily practical conversation.

So the duration doesn't matter quite as much as just once we are aware of these three conversations and we learn to look for the signals of what kind of conversation we're in, we can almost automatically overcome the challenges that it presents. It's just in a matter of awareness. And the reason why is because if you think about it, and you mentioned this before, communication is homo sapiens superpower, right? Yes. It's the thing that has allowed our species to be so successful.

So as a result, our brains have evolved to be really, really good at communication if it's given the right inputs. So what happens is that when you hear, there's three kinds of conversations, here's some ways to try and recognize what conversation you're in, your brain will actually make that into a habit very, very quickly. So back to the power of habit. Back to the power of habit. When you get into a communication, when you get into a conversation, step one, this is a social conversation. We're chewing the fat.

Everybody's looking to explore ideas, get to know each other. Are we having an emotional conversation? Hey, I need to give you empathy. I need to understand what you're feeling. Or are we doing the punch list? Are we doing a practical conversation here? And then you can come into it with a different expectation and technique. And here's my favorite example.

So you're sitting in a meeting, right? And you're waiting for the meeting to start. And the guy next to you, you just turn to him and you're like, hey, how was your weekend? And they say something like, oh, I went to go see my kid's graduation. It was great. Right. Now, the practical mindset, you could be like, oh, congratulations. Okay, let's get down to the agenda.

But the super communicator is going to say, oh, man, that sounds amazing. What did it feel like to watch your kid walk across that stage? Like, was that awesome? And he's going to that your friend is going to answer. for 15 seconds, and then you can be like, oh, man, that sounds really cool. Thank you for sharing that. Okay, let's get down to the agenda. When somebody signals to you, what kind of mindset they're in, and they might do it subtly just by saying, like, I went to my kid's graduation. It was great. Then if we match them, if we ask a question, particularly a deep question, how did you feel about that?

What we're doing is we're giving them an opportunity to align with us and for us to entrain with them. And it doesn't have to be super time consuming. It doesn't have to be super intimate. We don't have to be weeping on each other's shoulders. But when we do that, we both feel connected to each other. And that's going to make that practical conversation a lot easier to have. Yeah. What role, you know, this is like so great to have you on here because I get to ask my own personal questions here.

What role do anecdotes, storytelling, I mean, understand metaphors, analogies have a certain importance in communication. It's pretty obvious what they are. They help you understand something faster. or in a deeper way. But I noticed, and I noticed in my life, when I,

for some reason, maybe it's the Irish and the Greek in me, storytellers both, I would, and I grew up listening to anecdotes, right? I'd sit around the table, my Irish uncles,

aunts, grandparents, cousins, everybody would be telling stories. The Greeks do this particularly well as well, just over different beverages and libations. What role did,

like, telling anecdotes and sharing these, like, stories, have and then self-deprecation, same question. What are the roles of anecdotes and self-being self-deprecating? Because I've been self-deprecating for a long time, and sort of was a funny comedic device. And also it was something I learned on the stoops of Brooklyn

because we used to break each other's chops. And so if I could tell you I was a fat Greek bastard, before you could tell me I was a fat Greek bastard or, you know, as a drug Irish, you know, whatever, I could cut you off at the pass, you know, during our insult battles in my youth. But maybe we'd touch on those too. Yeah, absolutely. So it's a great question.

So anecdotes, I think anecdotes are important for two reasons. Number one is, if you think about what I was saying before, so every conversation is made, every discussion is made about different kinds of conversations. You might start emotional, go to practical, go to social, go back to emotional. The great thing about a story, a story is like a little package of all those different kinds of conversations, right? I'm going to tell you, I'm going to set up something and then I'm going to tell you, like, man, I got to the party and I was feeling really, really down.

But then Jim came up and he handed me this drink and I didn't know what was in it. And then later on that night, like, I found myself in bed with Susie, right? When I'm telling you that story, what I'm actually doing is I'm helping you through all these different kinds of conversations. I'm telling you about my emotional state. I'm telling you some practical stuff. There's probably a lesson that I'm expecting or that you'll carry away from this, which just might be like don't drink stuff that people hand to you.

There's a social element because we're talking about other people. So a story is a perfect little way of having these three little conversations in a very clear manner. But in addition, what we know is that if you ask people, tell me about a conversation you had a week ago. And you ask them, what did people say? They will almost never be able to remember what anyone said. They will remember the topics that were discussed, kind of. They'll remember who was in it. And they'll remember kind of how some people were positioned in it.

But they won't remember anything specific. But if you ask them, tell me how you felt during that conversation. They'll be able to tell you the emotional journey they were on. We remember. Fascinating. We remember how other people make us feel. We don't remember what they say quite as well. This is something I have.

Yeah. Go ahead. Well, a story gets around them, right? A story is a way of taking an idea and embedding it in some emotion so that you remember that story and therefore you remember the idea. Ah, see, it's fascinating. See, this is why I think storytelling and anecdotes are so much fun. Calling all seed in Series A startups, be sure to check out. HubSpot for startups and HubSpot Ventures for their million dollar pitch competition. Wait, what? A million dollars? Yes, that's right.

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super simple. Get ready to enter HubSpot for startups and HubSpot Venture. million dollar pitch competition, apply now at HubSpot.com slash million dollar pitch. HubSpot.com slash million dollar pitch, all one word, no spaces, no dashes. The link will be in the show notes. And good luck. I hope you win a million dollar investment at the million dollar pitch competition. What's the most embarrassing thing that ever had to? To me? Yeah. I'm genuinely asking you this story. Yeah, yeah. I did, by the way, when you told the story about how much you sucked as a manager. I think you sell 10 times as many books right there because you're being honest.

Like, you wrote this book because you're struggling with how you speak to your wife and emotional conversations. I think you just sell 10 times as many books when I just said that and recap it. Because you know what? Because it's authentic, right? It's authentic. And an HBS guy who sold 12 million copies of a book has got a problem.

I mean. Many, many problems, my friend. I know. But for somebody who's a great writer to, be a shi-communicator. It's like the best, you know, way to present the book. So I'll tell you, I'll tell you, I'll tell you when I was most embarrassed. And then I want to ask you the same question. Oh, no. So there was a, so I went to like this thing with my kids. I was taking them to like a game. And I had been, there was another dad there. I really liked

this dad. We would talk on the sidelines as the game was going on. And I was like, Jim, you know, this is like, I love looking forward. I always talked to Jim. I looked forward. to look talking to Jim. Every time I saw him, it would be, hey, Jim, what's up? And five games in, he was like, by the way, I just needed to let you know, my name is Steve.

I am such a dick. Wow. Yeah, that is. That was, I was somewhat red-faced at that moment. How about you? What's the most embarrassing thing you can, you can remember? It's not just the most embarrassing.

It's the most painful. Yeah. Yeah. It was physically the most painful I think I've ever been in and the most embarrassing. So I sold my second company, Weblogs, Inc, which was the producers of Engadget. You probably remember that blog. It was the number of blog in the world for a while, auto blog. So I'm like in my early 30 years ago, and I sell the company. We sold the company for $30 million.

I went from being broke to being rich overnight. And it was just this incredible success story, 18 months from start to finish, market. Humans, the investors. It's incredible. So I get the wires and everything. My partner and I, champagne, boom, we're rich. My friend is going to Sundance because his movies premiering. My friend, David Sachs, is premiering the film.

Thank you for smoking. And my other friend, just make this a complete crazy name drop. Elon Musk is a producer of that film, and he has a cameo in it. And his plane, at the time, the Falcon, has a camera. him. And so, David's also got a plane. Everybody's flying out from L.A. to Sundance. I have to go to a closing dinner with all the bloggers who work there and give everybody their bonus checks. But I really wanted to fly on the private jet. That would have been great, right, to fly to Sundance on a private jet. But I said, you know what, guys? I'm going to meet you there. So my wife, my friends, their wives, everybody's flying out to go to Sundance.

I'm going to meet them there on Southwest. I go buy the Southwest ticket. There's no flights left because it's Sundance from L.A. Right, right. I'm like, God damn it. There's one flight. 5.05 a.m. I'm like, I didn't know they had flights before 6 a.m.

5 a.m., you might as well stay out. I mean, so I got to get there a 405 for a 505. I am dead tired. I get on the flight. I got a middle seat. I go, I'm exhausted, my friends are already there, private jet, blah, blah, blah, put my bag up, I sit down in my middle seat, and I feel a weird sensation, like a crunching sound. Then I feel wetness, and then I feel heat, and then I jump up and I look down, and there is a giant

Starbucks cup and black coffee steaming in my seat. Oh, my God. And the woman in the window seat looks at me and goes, oh, were you sitting there? And I said, where your coffee was in my seat? And then I feel my ass is on fire, girls. But the plane is taxying like now at this point. And like the woman's trying to, or the plane's about to taxi, everybody's seated. I run to the bathroom.

I drop my draws. I see out of the corner of my eye my pasty, white Irish ass. is red. And I realize I may have to go to the hospital. So I start pouring, this is hot coffee ass. There's the name of this story. I start, you know how you can get like a little bit of water out of that? Yeah, yeah.

I start putting that on my ass. Little scoops of water. And they're banging on the door. Sir, we have to take off. You have to come out of the bathroom. I'm like, my ass is on fire. I can't get out of this bathroom. So I start taking my pants off.

I take my underwear off. I cool my ass down. Now there's like three or four people around the back of the air. Do you need an ambulance? Do you need whatever? Because now the flight attendants know what's happened. I mean, Starbucks coffee's hot. Yeah.

It's very hot, especially when you don't have milk. This is black coffee. This is one of my underwear off. I put my khakis back on. My khakis are destroyed. My ass is steam. I take, but my ass is still burning. So I take some of the seafold napkins and I wet them.

And I paste them to my. butt so I have coolness on my butt because I know I got to get the temperature down. I put that up. I got that under my white, tidy whitties are black, but I can't put them on. And so I get out of the thing and I'm holding it and I look. The whole plane is looking. Looking at you. I got the white.

I walk back to see the woman has her magazine or whatever like this. She does not want to make eye contact with me for this next? Does she apologize? She says nothing for the rest of the flight. Nothing. And I felt back for her. And I said to her, don't worry. It's like only first degree burns.

It's not like my ass isn't blistering, whatever. I get there to Sundance. I'm freezing my ass off literally as, you know, it's cold. I'm getting in my SUV. And my wife wants me to pick her up. Get back to the house, whatever, get changed. So I got this underwear. So I just tuck it into the side of the console, you know, between the seat.

I go pick everybody up. I got everybody in the car now. David Sachs, everybody. And like, my wife pulls the underwear out in front of everyone. What's this? Oh, my God. And I said, I had an accident on the plane. It's technically true.

I didn't have an accident. Technically, technically true. Technically true. Literally the most embarrassing, twice, twice embarrassed. Yeah. Yeah. It's brutal. It's good times though, right?

It's like, you know. It's a great memory. Yeah. I also thought there's something humbling about this. Like, you've finally, the kid from Brooklyn became a millionaire. Always feared being poor. And now I'm a millionaire, finally. I got my dream. And I still got to take this 5 a.m. flight.

Yeah. And I still burnt the shit out of my ass. And you know what? It doesn't matter how much money you have. You're going to sit on a hot, you're going to get hot coffee as sometime. It's going to happen. Life has a very, does a very good job of, of forcing us to recognize. recognize our limitations and keeping us humble if we're not.

So you had asked about self depreciation. So I think one of the things. Yeah, yeah. Depreciating. Yeah. So I think one of the things that what the, I think one of the reasons why that's so successful is because, because it's very authentic, right?

So one of the things that we know is that people's brains are very good at detecting in authenticity. Like we've always, we've all been at that party and someone asks us, you know, where, uh, where'd you go on vacation? And we recognize like three seconds in, they don't care where we're on vacation, they just want to tell us about where they went on vacation, right? Tell us about the yacht they rented.

So our brains have evolved to be very good at detecting this. And I think one of the things that happens with self-depreciating stories is that, is that we tend, it's a way for us to be authentic, right? Without without having to, without having to fake it. Oftentimes, like, if the story is true and you genuinely kind of look like, you know, the butt of the joke, right? If you have a... Yeah, exactly.

Then I think what it does is it, it conveys that authenticity. And it makes other people trust that everything we're going to say might be authentic. Because we've been willing to share something vulnerable. When people have an ask, they want something from the other person. This is a certain dynamic of conversation. You want the job. You want the promotion. you want the investment from the venture capitalist,

you want the customer to sign of the dot line, you want to get your book signed, you want to get your book approved, and you want to get a publisher. There's an imbalance there. There's an asker and there's the person who can give. It's not a sorry negotiation. That's a separate category.

But in those conversations, are there best practices there that you learned about how to frame them and how they should go down? for the goal of getting what you want, the investment, the book deal, etc. Yeah. So let's talk about if you're applying for a job or you're talking to a venture capital's group. And I'm curious if you would think that this is good advice as a VC yourself. So oftentimes we go in thinking, our job is to impress this person, right? My job is to impress

them that I'm a great hire or my job is to impress them that I'm a great investment. But again, a conversation is successful if we understand each other at the first outset. And so if I go in and I say like, here's why you should hire me, I'm fantastic. And I never ask you a question. And I never get a sense of like what you're actually looking for, how you're thinking about this problem. Then that I'm not trying to understand you. I'm just trying to force you to understand me. And so I think one of the best things you can do during job interviews, for instance,

is to go in and say, you know, they, they ask you interviews in the question to say like, look, do you mind if I ask you a question? Like I'm wondering, like, what do you think makes someone successful? or not successful in this position. Beyond what you've written down, what is it that you've seen that, what are you looking for that you've seen in the past helps someone succeed in this role?

Right? At that point, at that point, it becomes a conversation. And I think that you can tell me, I'm assuming during pitches, that the folks you end up investing in, they probably ask you questions, right?

They're trying to understand how you see the world, not so much. You would think. That's interesting. Yeah. But you have to understand you're dealing with two of the, and you do understand this having gone to HBS, which produces a lot of venture capitalists and a lot of entrepreneurs

and a lot of management consultants, sadly. Also known as a wasted life. Have you watched what's happening to management consultants since Chad GPT came out? No, I haven't, but it's probably not good. It's like, if you want gibberish, we got you covered. Type anything into chat GPT, and we will put words on a page

that seemingly are important that nobody will read anyway. My premise is chat GPT is basically like a McKinsey consultant. They're buying people out. They're like, please let us buy you out because people are not hiring them

because if you want a bunch of words in gibberish to give you some strategy, it actually turns out chat GPT any of these are really good at that, but you're just dealing with too good. Yeah. Yeah. Yeah, so you're dealing with these two groups that are both like...

So on the venture capital side, you have like a range of people who are, some of them are very thoughtful and ask a lot of questions who are in the Michael Moritz from Sequoia, previous journalist, and myself would be like, and not that I would ever compare myself to him as an investor, but both of us are journalists. Oh, Malik comes from that school where you're good at asking questions of reading people and understanding the next question to ask. you know, and seeing if the person's thoughtful. On the other side, and then you might have someone just completely arrogant lunatics who, just because they're the ones writing it, they're kind of like studio heads or something, giving a green light to a picture, right? So they're just high on their own supply lunatics and who knows why they invest. You know, there's a whole bunch of reasons, FOMO, you know, whatever.

And then on the other side, you have entrepreneurs who have so much enthusiasm and they're so effervescent. they're so maniacal. You can describe it positively or negatively about their idea that they just cannot stop talking about it. They cannot stop filling the air in every moment with everything they're so contained about, right? And if they did ask more questions, I think they would do better. But since I know that this is the group you're dealing with, which are people who, if they're going to be successful, are difficult. people, cantankerous people, but effective people. So there was a famous moment where the founder of Sequoia Capital drew a four-quadrant

diagram, agreeableness, disagreeable, ineffective, effective, competent, incompetent, whatever. And they just said to the younger VCs at Sequoia, where do you think we make our money in those four quadrant? Agreeable people, disagreeable people, competent people, incompetent people, competent people. Which one would you say is the big outliers and the power law? Well, I'm guessing that what the VCs, the YereVC said is they said agreeable competent and it's actually disagreeable continent. Correct. 100% correct. It turns out like, you know, Steve Jobs, yeah, Bill Gates, like

Zuckerberg, these people are not easy to get along with at times. And, you know, Travis from Uber, you know, he's got his own vision of how this is going to go, but highly competent. You make money on competent, agreeable people too. Just not, probably not going to be the outliers. So when confronted with a disagreeable person, like a founder who might say, like, why should I have you on the cap table or that's a stupid question? Like, I've had a founder say that's a stupid question. Think about the level of hootspah that takes.

Totally, totally. But it's actually, what's interesting about that is that that doesn't mean it's a bad question. So like someone who said or something to say, right? Because I think what I'm hearing you say, and tell me if I'm getting this wrong, is when someone is a disagreeable person, what they're also doing is they're being very authentic to themselves. Right. So they walk into that room and they're not asking you a question just because they want to impress you that the kind of person asks questions. Rather, they're telling you, like, if you ask me a dumb question, I'm going to let you know it's a dumb question.

Yeah. And if I ask you something like, why do you belong on this cap table? I'm actually asking you why you belong on this cap table. I'm asking you the most authentic thing that I can, that I'm curious about at this moment. So for me, I love it. I think it's great. I love people,

it's the Brooklyn and me who just get right to the point and who ask the hardest question because life is short. Everybody has options. So let's just get to it. Let's see if this is going to work or not. I like to go fast. But I do think asking a VC a couple of questions. is a great idea.

And I always tell them, like, go ask other founders what they think of the VC. Tell me about a difficult conversation you've had with them. Like, we call them dark references or backdoor references. There's a bunch of different terms for it. But don't tell the VC you're doing it. Just go look at people they've invested in and say, hey, how is Jason Calacados as an investor? Can I ask you another question? So one of the other things that super communicators do in addition asking questions that's really

important is they prove that they're listening. And there's actually a technique for this known as looping for understanding. which is that you ask a question, preferably a deep question, you repeat what the person said in your own words to prove to them that you're processing, and then you ask them if you got it right. So funny, you say this. I literally have an our training manual for new associates

and the firm researchers. Make sure you ask people, can I repeat your vision? This isn't a 20-minute meeting. The last thing they have to say to the founders, may I repeat back to you your vision for startup name? so I make sure I understand it completely. And I wrote that language.

And I make sure everybody says it every meeting because then that person, when they leave, we asked them to raid our firm with the NPS score, you know, how likely are you to recommend launch to another founder? We get incredibly high scores because when I started getting reviews back from founders, the number one criticism was Jason didn't understand my vision. Yeah. And I was like, am I arrogant?

Yes, okay, sure. Am I not listening? No, I'm listening. Well, why do people feel that way? And then when I realized, we say no to $199 out of 200 meetings. If somebody says no, it's very easy for the person to frame it as, well, they didn't understand. They understood my brilliance.

Exactly. They would have greenlighted my movie. They didn't hear what I was telling them. They didn't hear what I was telling them. They didn't hear what I was telling. So I created a device to cut them off at the past. Yeah. I think it's really, really smart.

And what we know is that, again, hardwired by a. evolution into our brain is that if I believe you are listening to me, I'm more likely to listen to you. So my question to you is, when you're evaluating a potential investment, how much do you care about whether that entrepreneur will listen to you? Like, how much of that is a factor in how you make decisions? That's interesting. I think that you have to understand if you want to be great at venture capital.

capital, that your returns, which is how you'll be judged ultimately, are completely dependent on you hitting a company in the power law, a great outlier. I was lucky enough to be the third or fourth investor at Uber, made my career, but then I did it with Robin Hood and a couple of other companies, com, other great companies. And it turns out missing a company, omission is the big in. And so, and that great founders do not need help from their venture capitalist. This is the big secret. The whole venture capital industry is predicated on this patina of we're here to help you. And, you know, it's going to be like this mentorship and this, you're going to be there by your side. And it turns out a lot of times the founders just run off with it. And you're lucky along

to be on the rocket ship. Like, you literally got on the rocket ship. What is the passenger on the rocket ship. What is their impact? Nothing. They lit the candle. The candle went to the moon. That's it. It got to escape velocity. So people kind of over-index or maybe overth think how much impact of VC themselves can have. So I do like somebody who I can have a vibrant discussion with, but they don't, I don't like somebody who changes their vision based on a question I ask. So sometimes I'll ask people a question. So should this be a consumer product or should you be selling to enterprises? And they're like, well, I just presented a consumer product to you, but do you think it should be enterprise? Because we can make an enterprise. I've literally had people change their business model in the room.

And I'm like, I was asking you to get your opinion on why it's not enterprise, but I don't want you to switch it. I actually asked that question in good faith. Like, I don't know the answer. Like, how did you come to consumer versus enterprise, right? So I guess I like somebody who can battle it out and debate stuff. I don't care if it's quietly over SMS, over email, you know, doing a walk and talk or on the phone or screaming. I don't care. I care about the outcome.

But I don't like somebody who is willy-nilly and will flip their vision based on a question I ask. Well, and I think that's exactly, that gets at the heart of like why conversations work, right? Because if a conversation is one way, then it's not a conversation. It's, and in one way doesn't mean just that I'm monologuing and you're listening. It can also mean you're not bringing into anything to the conversation. I'm asking you a question and you're assuming that I've already made up my mind. You're not actually listening to what I'm asking you and showing me that you're listening by responding and saying, actually, let me tell you why we're going consumer rather than Enterprise

because Enterprise is the stupidest thing on the face of the planet, right? Yeah. And that is that authenticity is that at the end of the day, there's a study that there's a study it was done by Harvard, called the Harvard Study of Adult Development, I'm sure you've heard of it. It's like one of the largest and longest studies. Yeah, they followed people around for 80 years now, thousands of people trying to figure out what makes you happy and healthy and successful, however you define success at age 65. What they found is that the only thing that basically predicts that is having a handful of close relationships at age 40. Yeah. And that the way we create

those close relationships is not simply by calling people up and following their lead. It's by leading together, right? That if you say something authentic, I'm going to say something authentic, too. If you say something revealing, I'm going to reveal something about myself. That doesn't mean I'm going to agree with you. It doesn't mean that we're like the same person, but it does mean that we're going to feel connected, right? And the people you love and the people I love are people we don't agree with all the time.

Yeah. They are, but they are people who know how to connect with us despite the fact that we disagree about that. I think that study is so profound, by the way, the one you're bringing up. Yeah. Because at the end of the day, the conclusion I've come to, and I lost a couple of friends over the last couple of years, Tony Shea, you know, from delivering happiness and Zappos died tragically. And Dave Goldberg, Goldie died as well. You know, there's two guys I play poker with all the time.

And I realize, wow, you know, I have a collection of memories, fossil conversation with those two gentlemen. And at the end of our lives, what do we actually have? we have a collection of memory. Yeah. With certain people. And to your point earlier in our conversation and how those conversations and moments made us feel, we may not remember the entirety of those, but we remember how they made us feel. And this is why when I was a young buck editor, I made people feel terrible.

I was like a hardcore person. And I then started to think about how it's making people feel. And I incorporated a lot more of levity while still deliver. bring, hey, we have a standard to head. We're in a competitive space. You got to work harder. And or you, this product is not acceptable as delivered. Where I used to just kick people out of a meeting.

Like, my God, this is garbage. Get the fuck out of the meeting. You know, literally would kick people out of an editorial meeting. Come back when you have something to contribute. You know, now I would just say, hey, this is not the standard we're going for. Please, you know, give it another shot. And we're better than this, aren't we? because we're not going to do well if we produce this.

So I don't know if you need some help with this or who you can run it by, but let's give it another shot and try to level this up. Well, and Goldie, I think, is a really good example of a super communicator because when I was covering, so I met him when I was covering the music industry for the LA Times before I went to the launch.com. Yeah, exactly. Exactly. My venture firm is launch.

com, by the way. Oh, nice. Because I always love launch and I always love that name, which I got from Gold. So we would go to breakfast and lunch pretty regularly. And I honestly don't remember anything we talked about, but I remember how humble he was, how genuinely he cared about my success and other people's success, how honest he was.

And I remember walking away from those conversations, feeling like this is one of the greatest guys, and feeling good myself, right? Like feeling like I was smart because, and that's the thing. He super communicators are not the most charismatic people. They're not the biggest extroverts. They can be charismatic and extroverts, but they can be permudgeonly introverts.

Yeah. Super communicators succeed because they show you that they want to connect with you. Yeah. And that defines is. Yeah. Yeah. Yeah. And he wanted to connect.

If he was having a conversation with you, he was genuinely present in that conversation. He wanted to connect with you. He did not want to impress you that he was the, I actually didn't even find out who his wife was until like I had known him for three months. Yeah. And I was like, how do you, how do you afford this life of yours? And he's like, well, you know, my wife works. She got on the right rocket ship as well.

Yeah, exactly. The actual rocket ship quote is from Cheryl. Oh, is it really? Yeah, she said to be get a seat in a rocket ship in Silicon Valley, take it. Yeah. Because it's just very rare that the rockets, you know, take off and you get to be on one. But yeah, Goldie, you know, in our poker group, you know, with me and Chamath and other folks, You know, we were all these crazy narcissistic lunatic, you know, trying to impress everybody and hit certain goals.

And he was just the most thoughtful guy who would talk to you about how you were doing and mentor you, how are you doing in your life? And they got a word for that, uh, mench. And he was a super mench. And it turns out, super communicator, super mench. They're probably adjacent. Basically the same thing. Yeah. Yeah.

It could be the same thing. Listen, I've kept you for over an hour. It's been amazing. Everybody go by the book. Charles, you know, we should, just, we should chew the fat and have you on the pot again. Like, every year, just come on. I would love that.

You should just talk shop because you got a lot of great insights. And I think we're both Gen Xers. Yes, yes. Come down to Santa Cruz sometime. We'll go surfing together. Absolutely, for sure. You know, I don't surf. I ski and I've gotten more into skiing, but you surf out down there with the shark?

You got it. So I didn't, I didn't start surfing until like 10 years ago when I was 40. It is a way easier than people think it is. Not easy, but it's more approachable. It's also so fun. I am not a graceful person. I'm not an athletic person. I feel like I am living poetry on a surfboard.

I don't look that way, but I feel it. That is what you're experiencing is flow, right? Where the whole world disappears when you get up on that board and you are connecting with that wave. there is nothing else in your mind. And that's what I get from downhill skiing. I got a place in Tahoe. After Tony, I never shared this,

but since we're having this like super communication moment, when Tony Shea died, I was like, I was talking to a friend that said, what do you do for fun? You know, and I was really depressed, uh,

I'm being honest about his death. Um, and I was like, we're talking about happiness and how much happiness he brought people. And so I said, uh, you know,

like I work, I invest and, you know, I take my girls over here, you know, da, things you do for other people, Jay Cowell. I'm like, okay, I play poker with my friends. Like, okay, yeah, that's something. What else? I was like, I couldn't come up with anything I did for

myself. You know, when you become a dad and you've got 400 investments and you got to do three podcasts a week, just your life as you become an adult gets filled up and you're not doing anything for yourself, essentially. You're just a mule. This is what happens to men, specifically of a certain age, I think. You become a mule. And I think moms have a different type of experience they have. And yeah, they also can become mules. And so I said, you know, I like skiing. How often do you ski?

I was like, I go like three or four days every other year or something. And then I did two years, two seasons back to back, 40 and 39 days. Oh my gosh. Yeah. And we did more skiing in two years. Incredible. Life changing. Did it, yeah.

Did it feel like, were you happier on the days you weren't skiing? Like, what did that do for you? and my brain chemistry went 5x in terms of my happiness when I wasn't. And when I don't ski for an extended period of time, I get sad. I'm sad in the summer because of the skiing. So I got to pick up surfing in the summer, I think. Surfing? You got to come do it, man.

I need a flow experience because I don't, and I had it the summer. Last summer I went, um, have you ever done an efoil? These, uh, boards. Are they cool? Yeah, I've seen them. So I did the efoil. I had an instructor. I was on a lake, which makes it super easy.

and you climb on the board and then when you get your balance first you ride the board just like laying on it and you have a remote control and you just hit the button and then you lean back a little bit and the foil that's under the water

with the blade when it angles up it lifts the board up out of the water so now you're, the board comes off the water and you're just on the foil and it's the closest thing to flying I've experienced

but it's very analogous to skiing and I've skied very fast the last couple years It's like over 50 miles an hour on diamonds with really, really great skis and just that feeling of, shh. You start to have this flow experience. And then you're popped up on the board. And then you lean back and the board pops out of the water and you lean forward and it goes down. And you lean a little left, right?

It is the most magical experience when you figure it out. And I think it's what happens to people when they catch a wave. Yeah. That's exactly the same thing. Yeah. Because it's so hard. And it's also like you're so in touch with nature, right? you have to pay attention to the ocean.

And as somebody who like spends most of his time on a screen, like when you are close to something natural, like in a kind of intimate way, like you have to pay attention to it. Yes. And it actually feels very redemptive. I think it's the same thing going down the mountain, right? Yes.

It's not just the speed. It's the snow. It's the sound. It's the quiet around you. It's the gravity of it, right? Like, I think it's magical. And there's something also about speed. and being in the moment where it requires 100% focus

because I've had moments where I'm drifting off and I was like, oh, just listen to a podcast while I'm skiing. Nope. I can listen to music while I'm skiing and I'll listen to a podcast or an audio box. Because you're going to bite it and you're going to destroy yourself. And biting it at 50 miles an hour and a diamond, no bueno. Not good. Especially not of 53.

Something is not going to go well. Season over. And man, I had so many profound moments. And it's great for writing too, I suspect. When you get off at surfing, a writing session must be great. Yeah, yeah. No, it's definitely, it's definitely like, I love it. Anyways, come down.

Come down. What's your favorite book on writing, by the way? I'll end on that because I know writers like books on writing. My favorite book on writing is probably actually this book by Jim Stewart, James Stewart, who's at the, he's a columnist of the New York Times now, but he also used to write for the New Yorker and still kind of does. It's called Follow the Story. If anyone wants to learn how to write, Jim Stewart's Follow the Story is a,

great, great book. I don't know this. Oh, it's a great book. I'm going to get it right now. Like, a non-writing book that I think teaches you a lot about writing is a visit from the Goon Squad by Jenny Egan. What's the premise? So it's about, it's a series of vignettes about these interconnected characters in the music

industry. It won the Pulitzer Prize a couple of years ago. It's a great book, just so much fun to read it right now. Oh, so it's nonfiction. It's fiction. It's fiction. It's fiction. Yeah, yeah. Visit from the Gun Squad is fiction. And the thing is that like when you read really good writers, one of the things that they're doing is they're teaching you how to write.

100%. Yeah. This is why I, you know, I always loved Michael Crichton. I don't know if you've read Michael Crichton. Oh my God. I love Michael Crichton. It's great. It's the easiest reading, but it also, there's something about the writing you and I do about business, about, you know, nonfiction writing. He was a nonfiction writer putting a layer of fiction on it where he's like, hey, you want to understand DNA? Let's talk about Jurassic Park. Oh, you want to understand aviation, airframe. Most of people haven't read that. But he really, like, and the story never stops. It just moves so fast. He's so great. He's respecting you as a reader. He's taking care of you, right? He's like, I want to teach you something, but I promise I'm not going to make it spinach. I'm going to, like, I'm going to reward you for learning. It's great. My two favorite on writing, Stephen King's

on writing. Have you read? No, I haven't read it, but people have recommended it to me. I should go read it. Just listen to it or read it. It's a great, like, if you're just going for a walk to listen to. He really talks about, like, writing Kujo and other moments. And so it's his autobiography, but it's about writing and his love of writing and, like, doing cocaine while writing Kujo, nose bleeding, like, so evocative. Like, he's like, and I had two tissues up my nose, because my I know he's believing because I'm doing so much cocaine while writing Kudjohn. We're like, we've seen the movie.

It's definitely a cocaine-driven movie. Dogs are like chasing you ever. We know, Stephen. We believe you. It's so great. We believe you. I'm going to go by that today. And then Anne Lamont has a book, Bird by Bird.

Yeah. Which is a bit more of like a practical, warm you up to writing book. So I always just tell people like, and then if you just want to get inspired, born standing up. I love that book. It's so beautiful. It's so, he is, and like, have you watched that there's this documentary that just came out on Apple? There's a Netflix documentary out now.

Yeah. Or I think it's Apple. I think it's Apple TV. Yeah. The first episode is better than the second one because the first episode is about how, when he was young. And like the thing is that none of us realize is that Steve Martin was the biggest celebrity in the world. Like, this is before we were born, right? In the 70s.

He was, he was like Bono. He was, like, he was bigger than Robin Williams. He was bigger than everyone. He was selling out not arenas like Dave Chappelle, not like the Staples Center. He was selling a giant stadium. He was selling out football arenas. And people were crazy about him. There were contests all over America to imitate Steve Martin.

So just watching that and being like, wow, because we all have a relationship to Steve Martin, but to see him before we were born is actually really interesting. And, you know, he wanted to do other things too, which is the thing I really respect about him. He got into banjo. He got into plays. He got into writing novellas, which I think means a short novel. And collecting art, right? And like, I didn't know that. Yeah. He's a huge art collector. I didn't know that. Yeah. Watch it. I think you'll like the document. I can't wait to watch. I think that's just like for me on the biography tip. Those two are just so transcended because the craftsmanship they

both have in their work, the care. Exactly. And I just tell people like, you have to really want which you also have to like want to learn the techniques. Yeah. You know, shout out Malcolm Gladwell, we'll give him hard time about his blue apron ads. But also like the 10,000 hours, which like is. You have to love the activity.

Like the thing is, if you're doing it for the money, you're never going to be great at it. Like, but if you're doing it because like, this is what you would do, because you're just obsessed with it, which is how I feel about writing,

honestly. Like, that's when you get good. It's fun. So jealous. I feel really lucky. I mean, you must have this thing where you're drowning an opportunity because people must want you

to write screenplays or do TV shows or do journalism. How do you say no to all the inbound speaking? You must get like crazy speaking fees and everything. How do you say no to a lot? It's always like a balance, right? I talked to my wife about it a lot. So during the pandemic, I'm sure you had a similar experience. Like, I was probably doing 30 speeches a year before the pandemic.

And that's like 60 days away from home, right? Yeah. It's two full months. And then the pandemic came in and it all shut down. and my life got so much better. I would like the level of stress went down by 20%. Absolutely. I said to my wife,

I had no idea that traveling was bringing this much stress in my life. So it's something we think about a lot. Like how do you balance? Because it's not just the money. It's also like the, like you want, if you're public intellectual, you like you want to,

you want your ideas out there. You want to be talking about them. Yeah. But I mean, and so efficiency. How do you say, because I, I'm getting these like,

your fees must be higher than mine, but I regularly get 50, 75K one-hour speech gigs. And I'm like, whoa, whoa, whoa, that's like a year salary for everybody else. Totally. How do I say no to that? And I'm saying no to them now. Yeah.

I think you have to. I think you have to. You have to say like at some point, I'm making decisions. Every time I've made a decision just for money, I've ended up usually thinking like it wasn't a great decision. Right. And so I think part of it is that you have to be able to have a criteria beyond those dollars to say like, does this bring?

me into a town, is it an audience that I'm really interested in and I want to talk to? Does this bring me into town where I have a friend who I haven't seen in a long time? Yep. Is this, right? Is this something where I can feel good about? I got an invitation to go talk to this about, I'm not, I actually ended up saying no, because I'm not an expert on this, but it was like DEI in a community that's very anti-D-EI.

And I was like, I'm not a DEI expert. I can't, I don't know that I'm going to add much. But things like that that are mission-driven are very, That's a fascinating discussion, the DEI one, yeah. Save that for it when we do another episode. You and I are pretty natural in conversation. I like fucking Gagin. Let's do it.

Let's do it more. Let's do another one. I think the audience is going to want a part two of this. I love it. Yeah, listen, everybody, just go buy both books right now. Stop what you're doing. I mean, books are like, honestly, books are the best deal in town, just like podcasts, you know. And some authors can do both.

Charles, you're just such a great guest. Thanks for sharing so much. putting yourself out there. And I think I got to get down there Santa Cruz and get on a wave this summer. Anytime. All right. We'll see you all next time on this week. Bye-bye.