The power of super communication with Charles Duhigg | E1938

26 Apr 2024 · 1 h 19 min

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In short

This Week in Startups: Episode E1938 Summary

Episode Overview

  • Title: The power of super communication with Charles Duhigg
  • Host: Jason Calacanis
  • Guest: Charles Duhigg, Pulitzer Prize-winning journalist and author of *Supercommunicators*.

In this episode, Jason and Charles delve into the nuances of communication, discussing various forms of conversation, the importance of humor, cultural differences in communication, and the dynamics that shift when someone has an ask.

Key Themes and Discussions

  1. Importance of Communication in Startups
  2. Core Message: Effective communication is crucial for success in startups.
  3. Transition from Technical to Communicative Skills: As startups evolve, the ability to communicate effectively becomes more valuable than technical skills (e.g., engineering).
  1. Types of Conversations
  2. Three Primary Types:
  3. Practical Conversations: Focus on problem-solving and decision-making.
  4. Emotional Conversations: Involve empathy and understanding without necessarily seeking solutions.
  5. Social Conversations: Relate to how individuals connect with each other and society.
  6. Dynamic Shifts: The dynamics in conversations change based on the context and the underlying purpose of the interaction.
  1. Role of Humor and Vulnerability
  2. Humor as Connection: Laughter often serves as a means of connecting with others, showcasing mutual understanding and empathy.
  3. Vulnerability in Conversations: Sharing personal experiences fosters trust and openness, enhancing communication effectiveness.
  1. Communication Across Cultures and Genders
  2. Cultural Nuances: Different cultures approach conversations differently, influencing comfort levels in emotional versus practical discussions.
  3. Gender Differences: While there are tendencies in communication styles based on gender, individuals are ultimately shaped by cultural upbringing and personal experiences.
  1. Anecdotes and Storytelling
  2. Power of Anecdotes: Stories encapsulate various conversation types and are memorable because they embed emotions and lessons.
  3. Self-Deprecation: Sharing flaws or embarrassing moments can create authenticity and make others feel more comfortable, fostering deeper connections.
  1. The “Ask” Dynamic
  2. Communication when Making Requests: When someone has an ask, the dynamics change. It's essential to ensure that both parties engage in a meaningful dialogue rather than a one-sided interaction.
  3. Effective Techniques: Asking questions and demonstrating active listening, such as through paraphrasing, helps in building rapport and understanding intentions.
  1. Insights from the Harvard Study of Adult Development
  2. Key Findings: Long-term happiness and health are closely tied to having close relationships, emphasizing the importance of effective communication in forming those bonds.

Conclusion In this engaging conversation, Charles Duhigg emphasizes that effective communication is not an inherent trait but rather a set of skills that can be cultivated. By understanding different types of conversations, leveraging humor, and fostering vulnerability, individuals can enhance their communication prowess in both personal and professional settings.

Additional Resources

  • Books Mentioned:
  • *Supercommunicators* by Charles Duhigg
  • *The Power of Habit* by Charles Duhigg
  • *On Writing* by Stephen King
  • *Bird by Bird* by Anne Lamott
  • *A Visit from the Goon Squad* by Jennifer Egan

Follow the Guests

  • Charles Duhigg:
  • [Twitter](https://twitter.com/cduhigg)
  • [Website](https://www.charlesduhigg.com/supercommunicators)
  • Jason Calacanis:
  • [Twitter](https://twitter.com/Jason)

Episode Links

  • [LinkedIn Jobs](https://www.linkedin.com/twist)
  • [Mantle](https://www.withmantle.com/twist)
  • [HubSpot Million Dollar Pitch](https://www.hubspot.com/milliondollarpitch)

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This summary captures the essence of Episode E1938 of *This Week in Startups*, highlighting key discussions and takeaways about communication and its impact on startups and personal relationships.

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Transcript

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0:03how about you what's the most embarrassing thing you can you can remember everybody's flying out from LA to Sundays but I said you know what guys I'm gonna 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 taxiing like now at this point i run to the bathroom.

0:56I 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 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 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.

1:48Apply 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 Duhigg is here. You, of course, know him. He's a writer at The New Yorker. He's got a new book out, Super Communicators. And his first book, he came on episode 751 of This Week in 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 so that's got to be a million seller hundreds of thousands oh yeah no um it's like i think it's like uh 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 which never happened in books yes no i was i was um yeah no it was great it was great it's really um i feel i'm very lucky to have had that happen and 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 book at exactly the right time in my life i've 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 in 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 and 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.

3:37I was hearing from a lot of managers saying, I have an MBA from Harvard Business School. I would hear from a lot of my classmates that say, 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 a hundred thousand a hundred percent communication is the wheelhouse and when you look back on the 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 if you pay attention to these cues and these rewards in your environment your habits almost change automatically yes and And so, and, and it, but it does mean focusing on those things that oftentimes it's easier for us not to focus on.

4:32Right. 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. And yet, you know, it doesn't matter what you eat today, but it does matter what you eat every single day. Yes. Yeah. yeah and this is where you know if you want to eat healthier uh you you have to create the systems process by which this will happen i did this i just taught my housekeeper how to make a french omelet because it happens to be one of my favorite things to eat for breakfast if not the my 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'll give it to the dogs three eggs but i I don't go look in the refrigerator for food, for breakfast food.

5:24I just get those free eggs. 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 unhealthy. Right? Because you're looking for something. You're in the flow. You're doing work. You're thinking about stuff. 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 um 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 um super forecasters i don't know if you know that yeah yeah yeah pretty uh it basically the premise there is um 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 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 uh 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 we can we meet with over zoom and sure enough we and then how do we qualified 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 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.

7:12And then the outcomes take care of themselves. If you eat the apple, you eat the omelet. 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? Like we tend to rely on our impressions.

7:43Like, 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 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.

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8:48Why? Because LinkedIn knows who might want your job. You know, they've got a lot of AI and machine learning going on over there. So even if they're not actively searching, they're going to see your role. And you know what? Those are some of the best candidates. And did you know that 70 % of LinkedIn users don't visit the other leading job sites? If you're not looking on LinkedIn, you're looking in the wrong place. And the best part is when you use LinkedIn jobs, 86 % of small businesses get a qualified candidate in 24 hours. So hire professionals like a professional on LinkedIn. LinkedIn jobs helps you get the right people faster.

9:17And guess what? The first one's on your boy, J-Cow. Post your first job for free, linkedin.com slash TWIST. That's right, linkedin.com slash twist to post your job for free. Terms and conditions do apply. tell me about the types of conversations um that you know you're going to confront in your life because you've really started to organize as you tell it through uh as you do in your books series of anecdotes and individuals and heroes who are involved in this process i won't give all that up because i want you to buy the book in fact 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 uh and if you if you have a power habit buy both um 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 really are oh my gosh yeah how many years you suffer for this book tell me three years i spent i spent three years writing this book and and like i think about this all the time i'll go buy a book for like 12 yeah 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 like writing this novel and i just it's a great it's the arbitrage there is for dollar is ridiculous in books because also you can give the book away then to somebody and get like a new 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 pay it's paying six bucks for six hours of listening or six hours of reading it's a dollar an hour pack with knowledge i mean it's shout out to books that are high quality and i mean i have 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 yeah turns out 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 out of 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 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.

11:45Yeah, absolutely. And it's not just FBI agents, right? There's this great story about Felix Sagala, 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?

12:16Right? 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, he's, he's, and so like, and he had wanted his whole life to be a CIA officer. He'd worked so hard to get this job. And eventually he meets this one woman, Yasmin, who is from a Middle Eastern nation.

12:49She works in 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, 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. You're terrible at this job. You've been here a year, you've recruited no one. And so he calls up he asked me and he's like, will 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 her up and it's not working.

13:20And 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 yeah 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 the 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 uh empathy deep listening there's a lot there and pacing there's a ton of skills yeah yeah and and super communicators the book is really about these skills, right?

14:31Because what we know is that no one is born a great communicator. There's no personality type that makes you a great communicator. It's just 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 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 like one thing, right?

15:11But actually 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.

15:49She 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 um 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 connections happening we have these mirror neurons there's a whole physiology to this absolutely 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 uh hero syndrome like the 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 is known as neural entrainment oh 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?

17:18Or I tell you about an idea, you experience that idea. Our brains are becoming entrained. And the goal of a conversation is to achieve that entrainment because we are hardwired to feel closer to each other, more 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 got to get the house clean you 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 uh 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 social the social which is about which is about how we relate to each other in the context of society right like so so and it's and not every conversation every discussion usually has a practical and an emotional part.

18:46Not 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 Blue Apron. Come on. You got to pay the bills. I know. when i said malcolm gladwell do a blue apron commercial 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 i convinced sam harris to do a podcast like years ago and my book agent uh 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 I'm podcasting.

19:38These 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, like you and I, we both live in the Bay area. And when we talk about San Francisco, right. And, and, and the problems that San Francisco has, I'm also, I'm still kind of bullish on San Francisco. Cause I just love it. The city so much. Like that's actually a social conversation. Cause one of the things we're talking about is how our, how our perceptions are a little bit different.

20:06and 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 and to speak in such a way that you can understand how I see the world.

20:43If 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?

21:19Or 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 well meet mantle this is the ai powered equity management platform for modern founders and operators it's going to simplify your strategy and save you a ton of time mantle's been built from the ground up by founders for founders and they've spent 12 years building and scaling successful companies themselves and they've seen every mistake in the book and they've solved for it.

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22:30Visit w i t h m a n t l e.com slash twist to get your first 12 months free and you're going to lock in an exclusive rate of$100 a month after your first 12 months. That's with mantle.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 the role of humor laughter and joking and there's different types of joking obviously but i'm curious where in our in these communications and these styles of conversations does the act of laughing about life and you know humor play a role because it's kind of my superpower, people tell me, is that I make the conversations funny and I drop a joke in once in a while and I get invited back to more dinner parties.

23:22Once 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.

23:49He'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 Catskills right now. Exactly. 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.

24:25And 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 um there are devices you and i use as writers you're a much more successful right than i am but uh you to your admission 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 did you how could this is perplexing to me i'm gonna ask a question on my behalf how could somebody be a transcendent top 0.1 percent writer and be horrible at communicating in person with words 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 yeah so you know the answer i know the answer to the question a lot of journalists are terrible at it right so so i found i what i think it was was that i was overconfident so i was 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.

26:02And 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.

26:29And 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 ask 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 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?

27:03Saying, 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 um i could yeah i could see i think i know the issue that you were also you were you had a blind side and i see this with a lot of people who go to a certain get a 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 hbs i hung out with hbsers i've spoken there three or four times this is the most confident yeah competitive problem-solving group of lunatics on the planet it's like taking the smartest kid in 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 telling them exactly right you're going to change the world yeah 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 solve problems they solve 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 to 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.

29:08You made those people feel like they weren't smart. And that sucks when your manager does that. Is that what happened? I think that that was an aspect of it, but I actually think the bigger thing is that it's, 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. Got it. 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.

29:44Or here's what you can do. 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? Because that's not. Men are from Mars. Women are from Venus or something. Let's get into it. let's let's let's let's talk about gender differences you do this massive research and uh 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 do the experts say well you and i've been married and have kids and yeah we have our own thoughts on gender differences i'll tell you what actually the data says what is the data set yeah so what the data says is that there's actually very few differences okay how genders communicate with a couple of exceptions okay the first of which is what do you feel comfortable in?

30:37So, 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, into problem solving. 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.

31:21It doesn't mean it's part of our character. It means simply that we've been inculcated with it, right? 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.

31:54ah whereas whereas in the u.s that actually might feel kind of like a betrayal right yeah yeah and so but that doesn't mean that like we have a different tolerance for intimacy it means that we are 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 uh 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 is 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 um you put those two things together those are the exact polar opposite conversations like 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 etc 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 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.

33:55It'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 which conversation you're in, your brain will actually make that into a habit very, very quickly. So you don't have to think about it.

34:28Back to the power of habit. Back to the power of habit. 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?

35:00And they say something like, oh, I went to go see my kid's graduation. It was great. Right? Now, the practical mindset 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. you, what did it feel like to watch your kid walk across that stage? Like, was that awesome? And 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, right? 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.

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35:38Then if we match them, if we ask a question, 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 uh 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 i 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 notice um 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 be telling stories the greeks do this particularly well as well uh 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 I mean, sort of was a funny comedic device.

37:03And 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 drunk Irish, you know, whatever I could cut you off with the pass, you know, during our insult battles, uh, in my youth, but maybe we touch on those two. Yeah, absolutely. So it's a great question. So, 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.

37:36You 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 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.

38:08I'm telling you about my emotional state. I'm telling you about 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. Yeah. And you ask them, what did people say? They will almost never be able to remember what anyone said.

38:38They 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. Good. Keep going. Well, a story gets around that, 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.

39:17Ah, it's fascinating. So 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. Applications are officially open for a limited time. Apply to be one of six founders flown out to HubSpot's flagship inbound conference taking place in Boston this September. When you get there, you're going to get a chance to pitch on stage in front of 1 ,000 folks and a panel of VCs and execs. Not only will you get invaluable feedback to help your business grow, but you also will be considered for an investment of up to$1 million.

39:56Again, you heard that right. Two commas,$1 million. Submissions are open until midnight Eastern time, May 17th, 2024. So let's get those applications in folks. This is a huge opportunity to showcase your startup's unicorn potential. So get your submission in and don't miss your shot. Here's the call to action. Super simple. Get ready to enter HubSpot for startups and HubSpot Ventures 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 recapped it because you know what 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 communicator it's like the best you know way to present the book um so i'll tell you i'll tell you um 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 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 talk to jim i looked forward to look talking to Jim.

41:46Every time I saw him it'd 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 was like, I am such a dick. Oh, I'm such an idiot. Wow. Yeah, that is. I was somewhat red-faced at that moment. How about you? What's the most embarrassing thing 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 uh i sold my second company weblogs inc which was the producers of engadget you probably remember that blog was the number one blog in the world for a while auto blog so i'm like in my early 30s 20 years ago and i sell the company we sold the company for 30 million dollars i i went from being broke to being rich overnight and uh it was just this incredible success story 18 months from start to finish mark cuban's the investor yeah it's incredible so i get the wires and everything my partner and i champagne boom we're rich my friend uh is going to sundance uh because his movie's premiering my friend david sachs is premiering the film thank you for smoking and my other friend just to 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 cameo and so david's also got a plane everybody's flying out from la to sundance i have to go to a closing dinner with all the bloggers who work there and and give everybody of 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 gonna meet you there so my wife my friends their wives everybody's flying out to go to sundance i'm gonna meet them there on southwest i go by the southwest ticket there's no flights left because it's sundance from la right right god damn it there's one flight 505 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 gotta get there a 405 for a 505 i am dead tired i get on the flight i got a middle seat um 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 i but the plane is taxiing 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 realized 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 but 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 was black coffee this woman's drink so i take 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 gotta get the temperature down i put that on i got that under my white tidy whities 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 lights i walk back to see the woman has her magazine book whatever like this she does not want to make eye contact with me for this does she ever does she apologize she says nothing for the rest of the flight nothing oh my gosh for her and i i said to her don't worry like it's like only first degree burns it's not like my ass isn't blistering whatever i get there to sundance i i'm freezing my ass off literally as you know it's cold i'm getting in my suv and uh my wife wants me to pick her up uh get back to the house whenever i 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 uh 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 technically true i did have an accident technically technically true technically true literally the most embarrassing twice twice embarrassed yeah yeah it's good times though right it's like 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 gotta take this 5 a.m flight yeah and i still burnt the out of my ass and you know what doesn't matter how much money you have you're gonna sit on a hot you're gonna get hot coffee as sometime it's gonna happen i life has a very it does a very good job of um of forcing us to 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 depreciation yeah so i think one of the things that the re 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 inauthenticity.

48:32Like we've all been at that party and someone asks us, you know, where'd you go on vacation? And we recognize like three seconds in, they don't care where we went 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 we tend it's a it's a way for us to be authentic right without without without having to um without having to fake it oftentimes like if the story is true and you genuinely kind of look like you know and that's the the butt of the the joke right if you have a so i speak like yeah exactly then 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.

49:26Because 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 on the line. You want to get your book signed. You want to get your book approved and you want to get a publisher. there's a there's an imbalance there there's an asker and there's the person who can give uh 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 like, if you're applying for a job or you're talking to a venture capitalists group, and I'm curious if you would think that this is good advice as a VC yourself.

50:23So 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 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 ask you interviews in the question to say like, look, do you mind if I ask you a question?

51:06Like, I'm wondering like, what do you think makes someone successful or not successful in this position? Like, 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 help someone succeed in this role? Right? Flip the script. Exactly. 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 uh yeah and you you do understand this having uh 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 um have you watched what's happening to management consultants since chat gpt came out no i haven't but it's probably like if you want gibberish we got you covered anything into chat gpt and we will put words on a page that seemingly are important that nobody will read anyway it's like my 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 and gibberish uh 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 two but tell me yeah yeah so you're dealing with these two groups that are both like so on the venture capital side um 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 journal previous journalist and myself would be like and not that i would ever compare myself to him as an investor but i both of us are journalists oh malik comes from that school where you're you're good at asking questions and 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 some more just completely arrogant lunatics um 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 um 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 um about their idea that they just cannot stop talking about it they cannot stop filling the air at 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 uh the founder of sequoia capital drew a four quadrant diagram agreeableness disagreeable ineffective effective competent incompetent whatever and they just said to the younger uh vcs at sequoia where do you think we make our money in those four quadrants agreeable people disagreeable people competent people incompetent people which one would you say is the big outliers in the power law well i i'm guessing that what the vcs the younger vcs 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 yeah 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 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 chutzpah 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 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.

55:41Right? So they walk into that room and they're not asking you a question just because they want to impress you that they're the kind of person to ask 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? It's, 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. Yeah. And so I don't. So for me, I love it. I think it's great. I love people. it's the brooklyn in me who just get right to the point and who asks 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 i like to go fast but um i do think asking a vc a couple of questions is a great idea um 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's jason calacanis 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 like and there's actually a technique for this known as looping for understanding uh 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 you're processing and then you ask them if you got it right so funny you say this i literally have in our training manual for new associates and the firm researchers make sure you ask people um 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 or startup name so i make sure i understand it completely and i wrote that language yeah and i make sure everybody says it every meeting because then that person when they leave we ask them to rate 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 i jason didn't understand my vision yeah i was like am i arrogant am yes okay sure uh 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 who to frame it as well they didn't understand they understood my brilliance exactly they would have green-lighted my movie they didn't hear what i was telling them telling them really listening yeah 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 evolution into our brain is that if I believe you are listening to me.

58:26I'm more likely to listen to you. Yeah. So my question to you is when, when you're evaluating a potential investment, how much do you care about whether that, that entrepreneur will listen to you? Like how much of that is a, is a factor in, in how you make decisions? That's interesting. Um, I think that you have to understand, um, if you want to be great at venture capital, that your returns which is how you'll be judged ultimately um 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 other great companies and it turns out missing a company omission is the is the big sin and so and the great founders do not need help from their venture capitalists this is the big secret that's interesting 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 overthink how much impact a vc themselves can have so i do like somebody who i can have a 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 um because we can make it enterprise i've literally had people change their business model in the room and i'm like uh 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?

1:00:44So 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, 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. And one way doesn't mean just that I'm monologuing and you're listening. It can also mean you're not bringing anything to the conversation.

1:01:19I'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 was done by harvard um 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 and they've 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 100 yeah and that the way we create those close relationships is not simply by calling people up and following their lead.

1:02:11It'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. And 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. But they are people who know how to connect with us despite the fact that we disagree about things. I think that study is so profound, by the way, the one you're bringing up.

1:02:42Yeah. 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 Hsieh, 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 realized 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 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 i was making people feel and i incorporated a lot more levity while still delivering hey we have a standard to hit we're in a competitive space you gotta you gotta work harder um and or you this product is not acceptable as delivered um 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 uh now i would just say hey this this is not the standard we're going for um please uh you know give it another shot and uh we're better than this aren't we because we're not going to do well totally if we produce this so i don't know if you need some help with this or 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 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 LA Times.

1:04:30Launch.com? Yeah, exactly. My venture firm is Launch.co, by the way. Oh, nice. Because I always love Launch and I always love that name, which I got from Golden. And 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, like it just, and feeling good myself, right? Like feeling, feeling like I was smart because, and that's the thing he super communicators are not the most charismatic people.

1:05:08They're not the biggest extroverts. They can, they can be charismatic and extroverts, but they can be curmudgeonly introverts. Yeah. Super communicators succeed because they show you that they want to connect with you. Yeah. And that, that feels special. Yeah. Yeah. Yeah. And he, and right. 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?

1:05:42And 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, if you get a seat in a rocket ship in Silicon Valley, take it. yeah because it's very rare that the rockets you know take off and you get out 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 you're doing in your life and uh they got a word for that uh mensch and he was a super mensch it turns out super communicator super mensch they're probably adjacent basically the same thing yeah yeah yeah it's not that could be the same thing listen i've kept you for over an hour it's been amazing everybody go buy the book charles you know we should just we should chew the fat and have you on the pot again like every year absolutely i would love that you should just talk shop because yeah you got a lot of great insights and i think we're both gen xers yes yes come down to you what are you sometime we'll go surfing together absolutely for sure you know i don't surf i ski and i 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 it is a way easier than people think it is not easy but like it's more approachable it's also so fun i it is i am not a graceful person i'm not an athletic person i feel like i am living poetry on a surfboard i never i don't look that way but i feel it that is uh what you're experiencing is flow right yeah 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 they said what do you do for fun you know i was because i was really depressed uh if i'm being honest about his death um 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 and they're like oh that's things you do for other people jacal i'm like okay uh i play poker with my friends like okay yeah that's something what else uh 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 gotta do three podcasts a week just your life as you become an adult it's filled up and you're not doing anything for yourself essentially you're just a mule uh this is what happens to men specifically of a certain age i think you become a mule and i think moms are 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 yeah 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 we did more skiing in two years incredible life-changing did it yeah did it feel like look were you happier on the days you weren't skiing like what did my happiness 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 skiing so i got to pick up surfing in the summer i think you got to come do it i need a slow experience because i i don't and i i had it the summer last summer i went um have you ever done an e-foil these uh boards are they cool yeah i've seen so i did the e-foil 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 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 like over 50 miles an hour on diamonds with really really great skis and just that feeling of you have to 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 it sounds amazing 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 yeah like when you are close to something natural like in a kind of intimate way like you have to pay attention to it then it actually feels very redemptive.

1:10:38I 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 book. Because you're going to bite it and you're going to destroy yourself. And biting at a 50 miles an hour on a diamond.

1:11:09No, when I'm good, especially not at 53, something's 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 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. Yeah. My favorite book on writing is probably actually this book by Jim Stewart. James Stewart, 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.

1:11:45It'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. It's a great book. I'm going to get it right now. I'm going to get it right now. 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 um so it's it's about it's it's a series of vignettes about these interconnected characters in the music industry it won the pulitzer prize a couple years ago it's a great book just so much fun looking at it right now oh so it's non-fiction 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 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 the easiest reading but it also there's something about the writing you and I do about business about you know non-fiction writing he was a non-fiction 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 people haven't read that But he really, like, and the story never stops.

1:13:05It just moves so fast. 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 cujo and other moments and so it's auto it's his autobiography but it's about writing and his love of writing and like doing cocaine while writing cujo nose bleeding like so evocative like he's like and i had two tissues up my nose because my nose was bleeding because i'm doing so much cocaine while writing cujo and we're like we've seen the movie it's definitely a cocaine driven movie yeah dogs are like chasing you everywhere we know steven we believe so great we believe you i'm gonna go buy that today and then ann 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 um born standing up oh i love that book it's so beautiful it's so he is and like have you watched the there's there's this documentary that just came out 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 a 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 like 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 i think you'll like that i can't wait to watch it i think that's just like for me on the biography tip those two are just so transcendent because the craftsmanship they both have in their work the care exactly and i just tell people like you you have to really want it but you also have to like want to learn the techniques yeah you know shout out malcolm gladwell we'll give him more time about his blue apron ads but also like the 10 000 hours which like is you have to love the activity like yeah like the thing is if you're doing it for the money you're 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 so jealous of you as a full-time writer it's fun so jealous i feel lucky i mean you must have this thing where you're drowning in 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 a lot of it's always like a balance right i talked to my wife about it a lot so during the pandemic i'm sure 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 that's two full months and and then the pandemic came in 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 into 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 a 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 you get also efficiency.

1:17:13How do you say, because 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. 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 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. 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?

1:17:50Is 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? Is this something where I can feel good about? I got an invitation to go talk to this about... 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-dei 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 but things like that that are mission driven are very that's a fascinating discussion the dei one yeah save that for when we do another episode i love it are pretty natural in conversation i like let's do another one i think the audience is going to want a part two of this i love it yeah listen uh everybody just go buy both books right now stop what you're doing uh 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 such a great guest thanks for sharing so much and putting yourself out there and i i think i gotta get down there santa cruz and get on a wave this summer anytime anytime we'll see you all next time on this bye bye

From the publisher

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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).

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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

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Check out Supercommunicators: https://www.charlesduhigg.com/supercommunicators

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