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Uber's Legendary Investor Explains Who Will Thrive in the AI Era (And Who Won't)

Six out of ten people would restart their careers if given the chance, highlighting widespread career dissatisfaction. The solution isn't endless grinding—it's finding work that genuinely fascinates you. Stop asking 'Can I do this for 30 years?' and start asking 'Does this work come free to me?' Whe

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My First Million

Key Takeaway

Six out of ten people would restart their careers if given the chance, highlighting widespread career dissatisfaction. The solution isn't endless grinding—it's finding work that genuinely fascinates you. Stop asking 'Can I do this for 30 years?' and start asking 'Does this work come free to me?' When you're in the right space, continuous learning and improvement happen naturally because you're drawn to knowing more about your craft.

Episode Overview

Bestselling author and venture capitalist Bill Gurley discusses his new book on career development and finding professional fulfillment. The conversation covers the alarming statistic that 6-7 out of 10 people would restart their careers, the importance of chasing curiosity over traditional passion, and how to build a successful career through peer groups, mentorship, and continuous learning. Gurley shares insights from interviewing successful founders and provides practical frameworks for career navigation, including the critical difference between perseverance and passion, and why peer groups may be more valuable than traditional mentorship.

Main Insights

The Career Regret Crisis

Research shows 6 out of 10 people would restart their careers if given the chance, with 53% not engaged at work. This widespread dissatisfaction stems from prioritizing economic stability over fulfillment and teaching people to grind without passion, leading to inevitable burnout.

The 30-Year Question as a Career Filter

Ask yourself: 'Do I want to be doing this 30 years from now?' This simple question provides clarity about whether you're on the right path. Apply it every 2-3 years, even when performing well, to ensure you're not just successful but fulfilled in your chosen direction.

Passion Should Outweigh Perseverance

Angela Duckworth, author of Grit, revised her famous 50/50 passion-perseverance formula, now believing passion deserves more weight. Society has taught people to grind for grinding's sake, but without genuine fascination for your work, effort feels like work and leads to burnout. When you're in the right space, continuous learning and improvement come naturally.

Peer Groups Trump Individual Mentorship

While everyone discusses mentors, peer groups are the undervalued accelerator of career success. A group of 4-6 peers on the same journey—ideally outside your organization—provides diverse perspectives, shared learning, network multiplication, and emotional support through difficult times. They help you recognize whether your company culture is normal or toxic.

Breadth Creates Breakthrough Innovation

Nobel Prize-winning scientists are 22x more likely to participate in activities like acting or dance. Top performers across fields speak more languages and have broader hobbies. Once you've achieved initial success in your field, deliberately expand outside it—different mental models from adjacent fields enable innovations that pure specialists can't see.

Insane Determination as the Common Thread

Jeff Bezos looks for one thing in founders: 'insane determination'—the belief that someone will pursue their goal no matter what. This quality, combined with hyper-curiosity about emerging technology, separates successful founders from the rest. They'll do it regardless of circumstances or opposition.

The CEO's Emotional Counter-Programming

Being a CEO is America's loneliest job because you must run emotionally counter to your organization. When the company struggles, you must bring positive energy and belief. When it's running hot, you must bring people down to earth. This constant emotional opposition is exhausting and why leadership coaching matters even for brilliant founders.

Notable Quotes

"If you could start your career over again, would you do it differently? And seven out of 10 said yes."

Bill Gurley

"The path I never traveled, the door I never opened is heavier in their mind."

Bill Gurley

"We've taught children, young adults, how to grind. We've taught them to persevere for the sake of perseverance. And if you're stuck, you're stuck."

Bill Gurley

"The only thing he looks for is this insane determinism. He wanted to believe the person was going to go do this no matter what come hell or high water."

Bill Gurley (about Jeff Bezos)

"I don't ever remember wanting to quit."

Bill Gurley

"The CEO job's the loneliest job in America. You need to run culturally opposite what's happening at the company."

Bill Gurley

Action Items

Suggested exercises inspired by the conversation.

  • 1
    Apply the 30-Year Test to Your Current Role

    Ask yourself honestly: 'Do I see myself doing this 30 years from now?' Look at the 'lifers' in your field—people who've done it their whole career. If that vision doesn't excite you, it's time to explore alternatives. Don't wait for certainty; use this as a periodic checkpoint every 2-3 years.

  • 2
    Form a Cross-Company Peer Group

    Assemble 4-6 peers at your career stage from OUTSIDE your organization. Create a structured format (weekly/monthly meetings, shared Slack/WhatsApp group) with clear rules and rituals. Share learnings, challenges, and networks. Kick out anyone who's sharp-elbowed or treats it as competition rather than mutual support.

  • 3
    Battle Card Your Career Options

    Instead of agonizing over one path, create 3-5 potential career scenarios. For each, use AI or mentors to project what your life looks like 2 years out—what you'd like, what you wouldn't, who you'd become. Let your brain explore multiple futures simultaneously before committing.

  • 4
    Deliberately Expand Beyond Your Field

    Once you've achieved initial success and differentiation, actively pursue learning outside your domain. Find mentors from different industries, pick up diverse hobbies, learn new languages. This breadth provides mental models and perspectives that create breakthrough innovations impossible for pure specialists.

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Full Transcript

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If you're crafting your own personal If you're crafting your own personal career and your high agency, AI is like career and your high agency, AI is like career and your high agency, AI is like a jpack. We've taught children, young a jpack. We've taught children, young a jpack. We've taught children, young adults, how to grind. We've taught them adults, how to grind. We've taught them adults, how to grind. We've taught them to persevere for the sake of to persevere for the sake of to persevere for the sake of perseverance. And if you're stuck, perseverance. And if you're stuck, perseverance. And if you're stuck, you're stuck. you're stuck. you're stuck. >> In order to like do these exercises of >> In order to like do these exercises of >> In order to like do these exercises of finding your passion, you sort of have finding your passion, you sort of have finding your passion, you sort of have to be like a ruthless [ __ ] You think to be like a ruthless [ __ ] You think to be like a ruthless [ __ ] You think >> unless you're trying to find that edge, >> unless you're trying to find that edge, >> unless you're trying to find that edge, somebody else may be. somebody else may be. somebody else may be. >> You have to understand the difference >> You have to understand the difference >> You have to understand the difference between risk and uncertainty. People between risk and uncertainty. People between risk and uncertainty. People most at threat by AI are the ones that most at threat by AI are the ones that most at threat by AI are the ones that aren't continuously learning that are aren't continuously learning that are aren't continuously learning that are just doing the same thing they did 10 just doing the same thing they did 10 just doing the same thing they did 10 years ago. years ago. years ago. >> How many times when you were doing it >> How many times when you were doing it >> How many times when you were doing it did you want to quit? did you want to quit? did you want to quit? >> I don't ever remember wanting to quit. >> I don't ever remember wanting to quit. >> I don't ever remember wanting to quit. >> Really? >> Really? >> Really? >> Really? What did the voice say when it >> Really? What did the voice say when it >> Really? What did the voice say when it was like I found my calling? >> I want to talk about the book because >> I want to talk about the book because there was this there's a bunch of crazy there was this there's a bunch of crazy there was this there's a bunch of crazy stats in the book. I want to talk about stats in the book. I want to talk about stats in the book. I want to talk about the Noval laurate thing. That was the Noval laurate thing. That was the Noval laurate thing. That was interesting. But the craziest like one interesting. But the craziest like one interesting. But the craziest like one of the craziest things early in the book of the craziest things early in the book of the craziest things early in the book I think did you run this survey and it I think did you run this survey and it I think did you run this survey and it said that like six or seven out of 10 said that like six or seven out of 10 said that like six or seven out of 10 people hate their job. people hate their job. people hate their job. >> Yes. So I had a coowwriter >> Yes. So I had a coowwriter >> Yes. So I had a coowwriter co-ressearcher on the book and we spent co-ressearcher on the book and we spent co-ressearcher on the book and we spent a ton of time together on Zoom calls and a ton of time together on Zoom calls and a ton of time together on Zoom calls and someone encouraged us to dive into a someone encouraged us to dive into a someone encouraged us to dive into a bunch of academic literature. We came bunch of academic literature. We came bunch of academic literature. We came across this Gallup poll that said 53% of across this Gallup poll that said 53% of across this Gallup poll that said 53% of people aren't engaged at work. And so we people aren't engaged at work. And so we people aren't engaged at work. And so we had this idea to ask like a thousand had this idea to ask like a thousand had this idea to ask like a thousand people if you could start your career people if you could start your career people if you could start your career over again, would you do it differently? over again, would you do it differently? over again, would you do it differently? And and seven out of 10 said yes. And And and seven out of 10 said yes. And And and seven out of 10 said yes. And then we we took that to to Wharton then we we took that to to Wharton then we we took that to to Wharton People Analytics to do the official People Analytics to do the official People Analytics to do the official academic version so you make sure you academic version so you make sure you academic version so you make sure you get all the statistical data correct. get all the statistical data correct. get all the statistical data correct. And their number came back six out of And their number came back six out of And their number came back six out of 10. So still a really big number. And 10. So still a really big number. And 10. So still a really big number. And >> crazy. >> crazy. >> crazy. >> There's a great book by Daniel Pink >> There's a great book by Daniel Pink >> There's a great book by Daniel Pink called The Power of Regrets. and he has called The Power of Regrets. and he has called The Power of Regrets. and he has a somewhat similar survey data of a somewhat similar survey data of a somewhat similar survey data of longitudinal through people's lives. And longitudinal through people's lives. And longitudinal through people's lives. And as you get older, you your regrets of as you get older, you your regrets of as you get older, you your regrets of inaction start to really weigh on you inaction start to really weigh on you inaction start to really weigh on you and ruminate in your brain. And a regret and ruminate in your brain. And a regret and ruminate in your brain. And a regret of inaction is is choosing actively not of inaction is is choosing actively not of inaction is is choosing actively not doing something versus a regret of doing something versus a regret of doing something versus a regret of action is I made a mistake. And humans action is I made a mistake. And humans action is I made a mistake. And humans are really good at allowing themselves are really good at allowing themselves are really good at allowing themselves to make a mistake. But the path I never to make a mistake. But the path I never to make a mistake. But the path I never traveled, the door I never opened is traveled, the door I never opened is traveled, the door I never opened is heavier in their mind. And it the survey heavier in their mind. And it the survey heavier in their mind. And it the survey might have been getting at that like might have been getting at that like might have been getting at that like people thinking, "Wow, what if I had people thinking, "Wow, what if I had people thinking, "Wow, what if I had done something differently?" done something differently?" done something differently?" >> Well, the reason I was asking is like I >> Well, the reason I was asking is like I >> Well, the reason I was asking is like I kind of want this whole like I'm kind of kind of want this whole like I'm kind of kind of want this whole like I'm kind of obsessed with this idea of finding your obsessed with this idea of finding your obsessed with this idea of finding your passion. Not just because of your book, passion. Not just because of your book, passion. Not just because of your book, but like one of my favorite books is but like one of my favorite books is but like one of my favorite books is Mastery by Robert Green. Mastery by Robert Green. Mastery by Robert Green. >> Yes. >> Yes. >> Yes. >> Which changed my life. Uh that changed >> Which changed my life. Uh that changed >> Which changed my life. Uh that changed my life. But the reason I'm I'm my life. But the reason I'm I'm my life. But the reason I'm I'm interested in it is because like um I interested in it is because like um I interested in it is because like um I previously had a company that I sold and previously had a company that I sold and previously had a company that I sold and it was like very successful uh and all it was like very successful uh and all it was like very successful uh and all the traditional measurements. I have a the traditional measurements. I have a the traditional measurements. I have a company now that's quite successful and company now that's quite successful and company now that's quite successful and I like what I do. But in the back of my I like what I do. But in the back of my I like what I do. But in the back of my mind I think that it's normal and maybe mind I think that it's normal and maybe mind I think that it's normal and maybe you could tell me if I'm wrong that like you could tell me if I'm wrong that like you could tell me if I'm wrong that like even grown-ups like who are successful even grown-ups like who are successful even grown-ups like who are successful still are like do am I am I following still are like do am I am I following still are like do am I am I following like the right path? Like am I following like the right path? Like am I following like the right path? Like am I following am I going to be in that six out of 10 am I going to be in that six out of 10 am I going to be in that six out of 10 or the four out of 10? Do you find that or the four out of 10? Do you find that or the four out of 10? Do you find that like even when you were when you left like even when you were when you left like even when you were when you left compact and then eventually got into VC compact and then eventually got into VC compact and then eventually got into VC which I imagine that would be your which I imagine that would be your which I imagine that would be your calling that you still questioned it calling that you still questioned it calling that you still questioned it >> after the engineering degree I went to >> after the engineering degree I went to >> after the engineering degree I went to Wall Street for 3 years. So I Wall Street for 3 years. So I Wall Street for 3 years. So I >> you like in research? >> you like in research? >> you like in research? >> I was in a sellside research analyst. >> I was in a sellside research analyst. >> I was in a sellside research analyst. Yeah. So I had two stops before I made Yeah. So I had two stops before I made Yeah. So I had two stops before I made it to to venture. And um in both cases, it to to venture. And um in both cases, it to to venture. And um in both cases, I had a moment of reflection and I it's I had a moment of reflection and I it's I had a moment of reflection and I it's more clear to me now than it was then, more clear to me now than it was then, more clear to me now than it was then, but where I I ask, do I see myself doing but where I I ask, do I see myself doing but where I I ask, do I see myself doing this 30 years from now? And in many this 30 years from now? And in many this 30 years from now? And in many businesses, there's a lifer in the room, businesses, there's a lifer in the room, businesses, there's a lifer in the room, you know, that's that's done it their you know, that's that's done it their you know, that's that's done it their whole life. And I I don't that sounds a whole life. And I I don't that sounds a whole life. And I I don't that sounds a little judgmental. I don't mean it to be little judgmental. I don't mean it to be little judgmental. I don't mean it to be like, but it it gives you a way to like, but it it gives you a way to like, but it it gives you a way to reflect on whether that's the the place reflect on whether that's the the place reflect on whether that's the the place you want to be in. you want to be in. you want to be in. >> Yeah. >> Yeah. >> Yeah. >> Because they did it. And and in both >> Because they did it. And and in both >> Because they did it. And and in both cases it after about 2 or 3 years I got cases it after about 2 or 3 years I got cases it after about 2 or 3 years I got to a no even though I was doing well in to a no even though I was doing well in to a no even though I was doing well in those jobs but thinking do I want to be those jobs but thinking do I want to be those jobs but thinking do I want to be still be doing this 30 years from now still be doing this 30 years from now still be doing this 30 years from now was was clarifying for me. was was clarifying for me. was was clarifying for me. >> But you said something interesting. So >> But you said something interesting. So >> But you said something interesting. So like all right I thought the book was like all right I thought the book was like all right I thought the book was amazing. The best chapter the the best amazing. The best chapter the the best amazing. The best chapter the the best part was the early part about f finding part was the early part about f finding part was the early part about f finding your passion and you're like that's the your passion and you're like that's the your passion and you're like that's the hardest part. And like you said that u hardest part. And like you said that u hardest part. And like you said that u just now you're like it didn't seem just now you're like it didn't seem just now you're like it didn't seem clear to me then but it does seem clear clear to me then but it does seem clear clear to me then but it does seem clear to me now that I was questioning that. to me now that I was questioning that. to me now that I was questioning that. >> Well I did do that exercise in my brain >> Well I did do that exercise in my brain >> Well I did do that exercise in my brain and there's another exercise that Bezos and there's another exercise that Bezos and there's another exercise that Bezos is famous for what he calls the regret is famous for what he calls the regret is famous for what he calls the regret minimization framework where he said minimization framework where he said minimization framework where he said what would my 80year-old self advise me what would my 80year-old self advise me what would my 80year-old self advise me to do in this situation which is another to do in this situation which is another to do in this situation which is another way to get at what I was doing and to way to get at what I was doing and to way to get at what I was doing and to get at this uh this notion of you know get at this uh this notion of you know get at this uh this notion of you know you only have one life. like are you you only have one life. like are you you only have one life. like are you really thinking about this decision with really thinking about this decision with really thinking about this decision with a reflection of the whole life? And so a reflection of the whole life? And so a reflection of the whole life? And so your 80-year-old self is probably more your 80-year-old self is probably more your 80-year-old self is probably more risk-seeking than you are in that moment risk-seeking than you are in that moment risk-seeking than you are in that moment because he's trying to minimize that because he's trying to minimize that because he's trying to minimize that that regret. that regret. that regret. >> What was the exercise you did then? How >> What was the exercise you did then? How >> What was the exercise you did then? How old were you? old were you? old were you? >> I the the thing I did is what I already >> I the the thing I did is what I already >> I the the thing I did is what I already said. I asked myself, do I still want to said. I asked myself, do I still want to said. I asked myself, do I still want to be doing this 30 years from now? And I be doing this 30 years from now? And I be doing this 30 years from now? And I did it once when I was an engineer. So I did it once when I was an engineer. So I did it once when I was an engineer. So I was 23, was 23, was 23, 24. But was that voice loud? 24. But was that voice loud? 24. But was that voice loud? >> I think it was loud. I had no >> I think it was loud. I had no >> I think it was loud. I had no inhibitions whatsoever about walking inhibitions whatsoever about walking inhibitions whatsoever about walking away. Like it didn't bother me. And I I away. Like it didn't bother me. And I I away. Like it didn't bother me. And I I may have benefited in the back of my may have benefited in the back of my may have benefited in the back of my brain uh from the fact that my father brain uh from the fact that my father brain uh from the fact that my father went across the country. He he took a went across the country. He he took a went across the country. He he took a flyer on a job. He got recruited from uh flyer on a job. He got recruited from uh flyer on a job. He got recruited from uh Virginia to Houston to be one of the Virginia to Houston to be one of the Virginia to Houston to be one of the first employees at NASA. first employees at NASA. first employees at NASA. >> That's cool. >> That's cool. >> That's cool. >> And and I knew he had done that. And and >> And and I knew he had done that. And and >> And and I knew he had done that. And and so I I didn't come from I think if you so I I didn't come from I think if you so I I didn't come from I think if you come from a family where multiple come from a family where multiple come from a family where multiple generations have stayed in the same generations have stayed in the same generations have stayed in the same town, it may feel really wild to just town, it may feel really wild to just town, it may feel really wild to just take flyers. take flyers. take flyers. All right, so this episode is all about All right, so this episode is all about All right, so this episode is all about excellence. A while back, I shared my excellence. A while back, I shared my excellence. A while back, I shared my personal framework for building personal framework for building personal framework for building excellence in my own life, and the team excellence in my own life, and the team excellence in my own life, and the team at HubSpot turned it into a 30-day at HubSpot turned it into a 30-day at HubSpot turned it into a 30-day operating system you can check out right operating system you can check out right operating system you can check out right now. It breaks down the systems it took now. It breaks down the systems it took now. It breaks down the systems it took me 10 years to figure out and shows how me 10 years to figure out and shows how me 10 years to figure out and shows how I actually use them dayto-day. These are I actually use them dayto-day. These are I actually use them dayto-day. These are systems that genuinely changed my life. systems that genuinely changed my life. systems that genuinely changed my life. So, if you want to build a good life, So, if you want to build a good life, So, if you want to build a good life, scan the QR code or click the link in scan the QR code or click the link in scan the QR code or click the link in the description. Now, let's get back to the description. Now, let's get back to the description. Now, let's get back to the show. the show. the show. >> When I was um 21 years old, I'm from >> When I was um 21 years old, I'm from >> When I was um 21 years old, I'm from Missouri. I went to school in Nashville, Missouri. I went to school in Nashville, Missouri. I went to school in Nashville, Tennessee, I had a hot dog stand and Tennessee, I had a hot dog stand and Tennessee, I had a hot dog stand and that's how I paid my way through that's how I paid my way through that's how I paid my way through college. It was called Southern Sam's. college. It was called Southern Sam's. college. It was called Southern Sam's. Wieners as big as a baby's arm. And we Wieners as big as a baby's arm. And we Wieners as big as a baby's arm. And we had a bunch of locations at these hot had a bunch of locations at these hot had a bunch of locations at these hot dog stands. It was really fun. And I was dog stands. It was really fun. And I was dog stands. It was really fun. And I was like, "This is so hard to be out in like, "This is so hard to be out in like, "This is so hard to be out in Tennessee weather selling hot dogs." It Tennessee weather selling hot dogs." It Tennessee weather selling hot dogs." It was so hard. And so I Googled like, was so hard. And so I Googled like, was so hard. And so I Googled like, "Where do internet companies live?" Cuz "Where do internet companies live?" Cuz "Where do internet companies live?" Cuz I didn't even know cuz I was obsessed I didn't even know cuz I was obsessed I didn't even know cuz I was obsessed with the internet. And it said San with the internet. And it said San with the internet. And it said San Francisco and I was like, "What internet Francisco and I was like, "What internet Francisco and I was like, "What internet companies are cool?" Or like I don't companies are cool?" Or like I don't companies are cool?" Or like I don't know what like what's like the hot know what like what's like the hot know what like what's like the hot thing. Well, at the time it was Uber. At thing. Well, at the time it was Uber. At thing. Well, at the time it was Uber. At the time it was called Uber Cab still the time it was called Uber Cab still the time it was called Uber Cab still and Airbed and Breakfast. and Airbed and Breakfast. and Airbed and Breakfast. >> Yes. >> Yes. >> Yes. >> And so I started looking at this thing >> And so I started looking at this thing >> And so I started looking at this thing called Airbed and Breakfast. called Airbed and Breakfast. called Airbed and Breakfast. >> And I cold emailed this guy named Brian >> And I cold emailed this guy named Brian >> And I cold emailed this guy named Brian the CEO. the CEO. the CEO. >> And he didn't reply to me. But then I >> And he didn't reply to me. But then I >> And he didn't reply to me. But then I found like another employee to email found like another employee to email found like another employee to email named Justin. And I emailed him and I named Justin. And I emailed him and I named Justin. And I emailed him and I was like, "I'm going to be there on was like, "I'm going to be there on was like, "I'm going to be there on Monday. Can I interview for this Monday. Can I interview for this Monday. Can I interview for this company?" Obviously Airbnb breakfast was company?" Obviously Airbnb breakfast was company?" Obviously Airbnb breakfast was called Airbnb. And uh they're like, called Airbnb. And uh they're like, called Airbnb. And uh they're like, "Yeah, you live in the Bay Area." And I "Yeah, you live in the Bay Area." And I "Yeah, you live in the Bay Area." And I was like, "Yeah, yeah, I live there." was like, "Yeah, yeah, I live there." was like, "Yeah, yeah, I live there." Which of course I didn't. I was in Which of course I didn't. I was in Which of course I didn't. I was in college in Tennessee. And so I flew out college in Tennessee. And so I flew out college in Tennessee. And so I flew out there the next day, got the interview, there the next day, got the interview, there the next day, got the interview, got the job, went back to Tennessee, got the job, went back to Tennessee, got the job, went back to Tennessee, dropped out of college, sold everything dropped out of college, sold everything dropped out of college, sold everything I had. But my parents are entrepreneurs I had. But my parents are entrepreneurs I had. But my parents are entrepreneurs in Missouri. They started their in Missouri. They started their in Missouri. They started their entrepreneurial career owning a fruit entrepreneurial career owning a fruit entrepreneurial career owning a fruit stand. stand. stand. >> Y >> Y >> Y >> and I remember when I told them, I was >> and I remember when I told them, I was >> and I remember when I told them, I was like, I'm going to leave school. I'm like, I'm going to leave school. I'm like, I'm going to leave school. I'm going to join this thing. And they're going to join this thing. And they're going to join this thing. And they're like, what's a startup and does it have like, what's a startup and does it have like, what's a startup and does it have health insurance? I was like, it has health insurance? I was like, it has health insurance? I was like, it has health insurance and it's paying like health insurance and it's paying like health insurance and it's paying like $22 an hour. I think it's going to be $22 an hour. I think it's going to be $22 an hour. I think it's going to be fine. And they're like, okay, cool. fine. And they're like, okay, cool. fine. And they're like, okay, cool. We'll come pack up your stuff. And I We'll come pack up your stuff. And I We'll come pack up your stuff. And I remember at that moment like that remember at that moment like that remember at that moment like that emotional support and what's is one of emotional support and what's is one of emotional support and what's is one of the biggest things that separates what the biggest things that separates what the biggest things that separates what allows people to win versus allowed allows people to win versus allowed allows people to win versus allowed people to lose because I've met so many people to lose because I've met so many people to lose because I've met so many people. A lot of my friends are people. A lot of my friends are people. A lot of my friends are immigrants and like the immigrant immigrants and like the immigrant immigrants and like the immigrant experience is interesting because a lot experience is interesting because a lot experience is interesting because a lot of the immigrants it seems like they of the immigrants it seems like they of the immigrants it seems like they fall in two categories. One category is fall in two categories. One category is fall in two categories. One category is like they came here with nothing so like they came here with nothing so like they came here with nothing so there's they have they're willing to do there's they have they're willing to do there's they have they're willing to do anything to to win and they go down one anything to to win and they go down one anything to to win and they go down one path and then the other path is I came path and then the other path is I came path and then the other path is I came here to create a big life. Don't screw here to create a big life. Don't screw here to create a big life. Don't screw this up. Take the safe path. Right? this up. Take the safe path. Right? this up. Take the safe path. Right? >> And my parents were not the safe path. >> And my parents were not the safe path. >> And my parents were not the safe path. And that was like the most support that And that was like the most support that And that was like the most support that they could have for me and it was so they could have for me and it was so they could have for me and it was so amazing. I'm glad I'm so glad you told amazing. I'm glad I'm so glad you told amazing. I'm glad I'm so glad you told that story because um even though the that story because um even though the that story because um even though the person this book is written towards is person this book is written towards is person this book is written towards is the the person on the career path and the the person on the career path and the the person on the career path and and I mean that we don't have a chapter and I mean that we don't have a chapter and I mean that we don't have a chapter on how to advise people like it's not on how to advise people like it's not on how to advise people like it's not written for the adviser but I think it written for the adviser but I think it written for the adviser but I think it will be particularly interesting to will be particularly interesting to will be particularly interesting to parents and adviserss to test whether or parents and adviserss to test whether or parents and adviserss to test whether or not they're willing to help support not they're willing to help support not they're willing to help support people in the way that your parents did. people in the way that your parents did. people in the way that your parents did. Well, I think that's a big deal because Well, I think that's a big deal because Well, I think that's a big deal because like for example, you go to the doctor like for example, you go to the doctor like for example, you go to the doctor to get like your basic stuff checked. I to get like your basic stuff checked. I to get like your basic stuff checked. I go to college, I go to school to get go to college, I go to school to get go to college, I go to school to get good grades, but at no point do they ask good grades, but at no point do they ask good grades, but at no point do they ask like are you asked like are you happy like are you asked like are you happy like are you asked like are you happy doing this? And I think that that's like doing this? And I think that that's like doing this? And I think that that's like I think that's why I'm still I don't I think that's why I'm still I don't I think that's why I'm still I don't think I've ever formally I don't think think I've ever formally I don't think think I've ever formally I don't think we've ever formally learned how do you we've ever formally learned how do you we've ever formally learned how do you find I call it eeky guy which I'm sure find I call it eeky guy which I'm sure find I call it eeky guy which I'm sure you're very familiar with. It's this you're very familiar with. It's this you're very familiar with. It's this Japanese term where imagine like a ven Japanese term where imagine like a ven Japanese term where imagine like a ven diagram but there's four. It's what the diagram but there's four. It's what the diagram but there's four. It's what the world wants, what the world wants to pay world wants, what the world wants to pay world wants, what the world wants to pay for, what you're good at, and what for, what you're good at, and what for, what you're good at, and what you're passionate about. The goal is to you're passionate about. The goal is to you're passionate about. The goal is to find something right in the middle. But find something right in the middle. But find something right in the middle. But no one teaches that, right? It's and so no one teaches that, right? It's and so no one teaches that, right? It's and so it's interesting. The reason I like your it's interesting. The reason I like your it's interesting. The reason I like your book is because that's what it's about. book is because that's what it's about. book is because that's what it's about. And yeah, and in the uh chapter titled And yeah, and in the uh chapter titled And yeah, and in the uh chapter titled Chase Your Curiosity, I tried to borrow Chase Your Curiosity, I tried to borrow Chase Your Curiosity, I tried to borrow as many of those type of exercises as as many of those type of exercises as as many of those type of exercises as possible. before I even went out. I'm possible. before I even went out. I'm possible. before I even went out. I'm surprised I didn't find that one, but I surprised I didn't find that one, but I surprised I didn't find that one, but I found like 10 others and and I put them found like 10 others and and I put them found like 10 others and and I put them all in there. Like I'm I'm trying to all in there. Like I'm I'm trying to all in there. Like I'm I'm trying to give people as many of those pathways as give people as many of those pathways as give people as many of those pathways as possible cuz I think the very hardest possible cuz I think the very hardest possible cuz I think the very hardest part is to figure out actually what it part is to figure out actually what it part is to figure out actually what it is that drives you in this way that's is that drives you in this way that's is that drives you in this way that's going to make it very easy for you to going to make it very easy for you to going to make it very easy for you to differentiate yourself. And um it's differentiate yourself. And um it's differentiate yourself. And um it's funny, you know, you you you mentioned funny, you know, you you you mentioned funny, you know, you you you mentioned that one. There's a story in the book that one. There's a story in the book that one. There's a story in the book about this guy Bert Beverage in Austin, about this guy Bert Beverage in Austin, about this guy Bert Beverage in Austin, Texas who's 40 years old and he's Texas who's 40 years old and he's Texas who's 40 years old and he's watching a PBS show and they say to take watching a PBS show and they say to take watching a PBS show and they say to take a sheet of paper, put it horizontal, a sheet of paper, put it horizontal, a sheet of paper, put it horizontal, draw a line down the middle, write on draw a line down the middle, write on draw a line down the middle, write on the left what you love to do and on the the left what you love to do and on the the left what you love to do and on the right what you're good at and try and right what you're good at and try and right what you're good at and try and find something in the middle. And find something in the middle. And find something in the middle. And through that exercise, he quit being a through that exercise, he quit being a through that exercise, he quit being a mortgage broker. He had been a mortgage broker. He had been a mortgage broker. He had been a seismologist before that and launched a seismologist before that and launched a seismologist before that and launched a vodka company called Titos um at the age vodka company called Titos um at the age vodka company called Titos um at the age at the age of 40. at the age of 40. at the age of 40. >> I think there's this like famous Mosart >> I think there's this like famous Mosart >> I think there's this like famous Mosart quote where someone was like asking quote where someone was like asking quote where someone was like asking Mosart like how do I find my way or how Mosart like how do I find my way or how Mosart like how do I find my way or how do I like do I have what it takes to be do I like do I have what it takes to be do I like do I have what it takes to be the man? And Mosart was like dude if the man? And Mosart was like dude if the man? And Mosart was like dude if you're asking that question the answer you're asking that question the answer you're asking that question the answer is no because the conquerors just is no because the conquerors just is no because the conquerors just conquer. And I I hated his reply to that conquer. And I I hated his reply to that conquer. And I I hated his reply to that because I'm but I'm curious. So I don't because I'm but I'm curious. So I don't because I'm but I'm curious. So I don't even know all of the companies you've even know all of the companies you've even know all of the companies you've invested in because you've been doing it invested in because you've been doing it invested in because you've been doing it for so long. You've like I don't know for so long. You've like I don't know for so long. You've like I don't know how many unicorns have you invested in? how many unicorns have you invested in? how many unicorns have you invested in? >> I don't know. I don't >> I don't know. I don't >> I don't know. I don't >> dozens. >> dozens. >> dozens. >> Sure. >> Sure. >> Sure. >> A lot. >> A lot. >> A lot. >> Yeah. >> Yeah. >> Yeah. >> And you've been around all the movers >> And you've been around all the movers >> And you've been around all the movers and shakers. Um whether you invested in and shakers. Um whether you invested in and shakers. Um whether you invested in or you pass or not, you were somehow or you pass or not, you were somehow or you pass or not, you were somehow like touched all these amazing people. like touched all these amazing people. like touched all these amazing people. Did they follow a similar path? Did they follow a similar path? Did they follow a similar path? >> Um for the founders, I think you'd find >> Um for the founders, I think you'd find >> Um for the founders, I think you'd find a lot of different stories and different a lot of different stories and different a lot of different stories and different pathways that got them to where they pathways that got them to where they pathways that got them to where they are. I mean, if you the like the are. I mean, if you the like the are. I mean, if you the like the Zuckerberg story is pretty famous. he's Zuckerberg story is pretty famous. he's Zuckerberg story is pretty famous. he's at Harvard doing messing around and and at Harvard doing messing around and and at Harvard doing messing around and and that's very different from the path say that's very different from the path say that's very different from the path say Gates took or or even Bezos. So I don't Gates took or or even Bezos. So I don't Gates took or or even Bezos. So I don't know that there is a pathway to that know that there is a pathway to that know that there is a pathway to that place. Um I'll tell you I I once asked place. Um I'll tell you I I once asked place. Um I'll tell you I I once asked Jeff Bezos how he could possibly be good Jeff Bezos how he could possibly be good Jeff Bezos how he could possibly be good at angel investing while he's running at angel investing while he's running at angel investing while he's running this company. this company. this company. >> What did what did he do angel wise? >> What did what did he do angel wise? >> What did what did he do angel wise? >> Oh he did uh Google Uber like it's a >> Oh he did uh Google Uber like it's a >> Oh he did uh Google Uber like it's a murderous road. murderous road. murderous road. >> He was on the uh he was in the seed >> He was on the uh he was in the seed >> He was on the uh he was in the seed round of Google. round of Google. round of Google. >> Yes. >> Yes. >> Yes. >> Wow. That's amazing. What was the >> Wow. That's amazing. What was the >> Wow. That's amazing. What was the evaluation then? evaluation then? evaluation then? >> I think that first round was a 10 >> I think that first round was a 10 >> I think that first round was a 10 poster. But but but to get to the point, poster. But but but to get to the point, poster. But but but to get to the point, he said the only thing he looks for is he said the only thing he looks for is he said the only thing he looks for is this insane determinism. He like he he this insane determinism. He like he he this insane determinism. He like he he wanted to believe the person was going wanted to believe the person was going wanted to believe the person was going to go do this no matter what come hell to go do this no matter what come hell to go do this no matter what come hell or high water. And I think that may be a or high water. And I think that may be a or high water. And I think that may be a common trait of a lot of the founders. common trait of a lot of the founders. common trait of a lot of the founders. They're just really really determined um They're just really really determined um They're just really really determined um and pushing against this thing. The and pushing against this thing. The and pushing against this thing. The other thing that's true of any tech other thing that's true of any tech other thing that's true of any tech founder is they're hyper curious about founder is they're hyper curious about founder is they're hyper curious about the edge of what the technology can do. the edge of what the technology can do. the edge of what the technology can do. And anytime there's a big disruption, AI And anytime there's a big disruption, AI And anytime there's a big disruption, AI being the most recent, but before that being the most recent, but before that being the most recent, but before that there was social media and the mobile there was social media and the mobile there was social media and the mobile wave and the SAS wave and all these wave and the SAS wave and all these wave and the SAS wave and all these waves and they create opportunity waves and they create opportunity waves and they create opportunity because incumbents are usually slow to because incumbents are usually slow to because incumbents are usually slow to embrace them and so you can run at these embrace them and so you can run at these embrace them and so you can run at these things fast. But that requires you to be things fast. But that requires you to be things fast. But that requires you to be hyper curious about where the world's hyper curious about where the world's hyper curious about where the world's going and what's changing so that you going and what's changing so that you going and what's changing so that you can master it before anyone else does. can master it before anyone else does. can master it before anyone else does. >> You uh there's this cool book called >> You uh there's this cool book called >> You uh there's this cool book called Grit. We talked about it a ton here on Grit. We talked about it a ton here on Grit. We talked about it a ton here on this podcast and you cite it a bunch. this podcast and you cite it a bunch. this podcast and you cite it a bunch. Yeah. Yeah. Yeah. >> It's awesome. I forget the exact >> It's awesome. I forget the exact >> It's awesome. I forget the exact equation, but it's basically like she equation, but it's basically like she equation, but it's basically like she Angela Duckworth, she's like Angela Duckworth, she's like Angela Duckworth, she's like >> I think she started um the original book >> I think she started um the original book >> I think she started um the original book with 50% passion and 50% perseverance. with 50% passion and 50% perseverance. with 50% passion and 50% perseverance. And um one thing we highlight, we And um one thing we highlight, we And um one thing we highlight, we actually had a chance to talk to her, actually had a chance to talk to her, actually had a chance to talk to her, which I'm super grateful for, but we which I'm super grateful for, but we which I'm super grateful for, but we found this podcast she had done 10 years found this podcast she had done 10 years found this podcast she had done 10 years later where she said it probably later where she said it probably later where she said it probably shouldn't have been 50/50, that it shouldn't have been 50/50, that it shouldn't have been 50/50, that it needed to put more weight on passion. needed to put more weight on passion. needed to put more weight on passion. And her her fear is that we've taught And her her fear is that we've taught And her her fear is that we've taught children, young adults, how to grind. So children, young adults, how to grind. So children, young adults, how to grind. So the we've taught them to persevere for the we've taught them to persevere for the we've taught them to persevere for the sake of perseverance. And she the sake of perseverance. And she the sake of perseverance. And she believes that now that now she believes believes that now that now she believes believes that now that now she believes that leads to burnout. And so if you that leads to burnout. And so if you that leads to burnout. And so if you have like all this effort without the have like all this effort without the have like all this effort without the love for it, it it feels more like work. love for it, it it feels more like work. love for it, it it feels more like work. And one of the things, you know, my the And one of the things, you know, my the And one of the things, you know, my the second principle here after you chase second principle here after you chase second principle here after you chase your curiosity is to hone your craft. your curiosity is to hone your craft. your curiosity is to hone your craft. And that's a lifelong journey, always And that's a lifelong journey, always And that's a lifelong journey, always learning. And for people that are in the learning. And for people that are in the learning. And for people that are in the right space, that comes free. Like you right space, that comes free. Like you right space, that comes free. Like you just do it naturally. You wake up and just do it naturally. You wake up and just do it naturally. You wake up and want to do it. Like you're drawn to want to do it. Like you're drawn to want to do it. Like you're drawn to knowing more about the craft. And and I knowing more about the craft. And and I knowing more about the craft. And and I think that that correlates nicely with think that that correlates nicely with think that that correlates nicely with where where she came out, which is you where where she came out, which is you where where she came out, which is you it's hard to do all the things I it's hard to do all the things I it's hard to do all the things I recommend in this book if you don't recommend in this book if you don't recommend in this book if you don't truly love it. truly love it. truly love it. >> I didn't realize it, but passion I think >> I didn't realize it, but passion I think >> I didn't realize it, but passion I think is probably I think passion is kind of a is probably I think passion is kind of a is probably I think passion is kind of a bad word because like passion kind of bad word because like passion kind of bad word because like passion kind of implies that I'm going to like implies that I'm going to like implies that I'm going to like everything I do. And if you like talk to everything I do. And if you like talk to everything I do. And if you like talk to like a lot of athletes, they're like, like a lot of athletes, they're like, like a lot of athletes, they're like, "Well, I love competing. I do like "Well, I love competing. I do like "Well, I love competing. I do like practicing, but there's definitely days practicing, but there's definitely days practicing, but there's definitely days that I hate doing it, but I'm a pro and that I hate doing it, but I'm a pro and that I hate doing it, but I'm a pro and I'm going to do it no matter what." And I'm going to do it no matter what." And I'm going to do it no matter what." And like I love winning. like I love winning. like I love winning. >> We highlight in the book that that >> We highlight in the book that that >> We highlight in the book that that word's kind of clichéish and overused. word's kind of clichéish and overused. word's kind of clichéish and overused. Seinfeld gave a talk at Duke where he Seinfeld gave a talk at Duke where he Seinfeld gave a talk at Duke where he said fascination was a better word. I said fascination was a better word. I said fascination was a better word. I think obsession is a good word. Um we think obsession is a good word. Um we think obsession is a good word. Um we titled the chapter chase your curiosity. titled the chapter chase your curiosity. titled the chapter chase your curiosity. Like what just what is it that you you Like what just what is it that you you Like what just what is it that you you can't ignore? Like what is this thing can't ignore? Like what is this thing can't ignore? Like what is this thing that you love so much that you always that you love so much that you always that you love so much that you always want to know more about it? Yeah. want to know more about it? Yeah. want to know more about it? Yeah. >> What was your uh you did a good job of >> What was your uh you did a good job of >> What was your uh you did a good job of like listening all these exercises to like listening all these exercises to like listening all these exercises to like find it. What was the uh most like find it. What was the uh most like find it. What was the uh most productive one that you found? productive one that you found? productive one that you found? >> I mentioned the one that Tito had used. >> I mentioned the one that Tito had used. >> I mentioned the one that Tito had used. Um the the team that wrote Designing Um the the team that wrote Designing Um the the team that wrote Designing Your Life has has one that they say is Your Life has has one that they say is Your Life has has one that they say is most popular, which is is battle most popular, which is is battle most popular, which is is battle carding. So like come up with three to carding. So like come up with three to carding. So like come up with three to five potential career paths, not just five potential career paths, not just five potential career paths, not just one, and let your brain roll around in one, and let your brain roll around in one, and let your brain roll around in them for a while. So you you could do them for a while. So you you could do them for a while. So you you could do that, especially with AI today. You that, especially with AI today. You that, especially with AI today. You could imagine I'm going to do this. What could imagine I'm going to do this. What could imagine I'm going to do this. What does it look like two years from now? does it look like two years from now? does it look like two years from now? Like who are you know what might I like? Like who are you know what might I like? Like who are you know what might I like? What might I not like? You can you and What might I not like? You can you and What might I not like? You can you and then you know you could say well what if then you know you could say well what if then you know you could say well what if it were this or this. So that's an it were this or this. So that's an it were this or this. So that's an exercise. Um I think having the mental exercise. Um I think having the mental exercise. Um I think having the mental relaxation to not feel like some path relaxation to not feel like some path relaxation to not feel like some path you've been down is some cost like I'm you've been down is some cost like I'm you've been down is some cost like I'm going to go try this and if it works going to go try this and if it works going to go try this and if it works great. If not I'll do something else. great. If not I'll do something else. great. If not I'll do something else. Just as your parents said it's okay to Just as your parents said it's okay to Just as your parents said it's okay to quit college and go work there. Um, it's quit college and go work there. Um, it's quit college and go work there. Um, it's okay to quit the job you're in as well. okay to quit the job you're in as well. okay to quit the job you're in as well. And I just fear we've put so much weight And I just fear we've put so much weight And I just fear we've put so much weight on economic stability. You know, you on economic stability. You know, you on economic stability. You know, you mentioned some of those immigrants mentioned some of those immigrants mentioned some of those immigrants families and what they they push that families and what they they push that families and what they they push that that that there's this burden to do that that that there's this burden to do that that that there's this burden to do that above and beyond what might be above and beyond what might be above and beyond what might be fulfilling in your life. And I I think fulfilling in your life. And I I think fulfilling in your life. And I I think it'd be better if we got out of that. it'd be better if we got out of that. it'd be better if we got out of that. And and or or at least this way. Think And and or or at least this way. Think And and or or at least this way. Think of it as a an you know a gauge. We've of it as a an you know a gauge. We've of it as a an you know a gauge. We've gone pretty damn far to one side. Let's gone pretty damn far to one side. Let's gone pretty damn far to one side. Let's let's bring it back a little bit. let's bring it back a little bit. let's bring it back a little bit. >> Have you messed up with your like have >> Have you messed up with your like have >> Have you messed up with your like have you had to pull yourself back with your you had to pull yourself back with your you had to pull yourself back with your kids? kids? kids? >> Yeah. Yeah. Yeah. I think there is a and >> Yeah. Yeah. Yeah. I think there is a and >> Yeah. Yeah. Yeah. I think there is a and having um they're all in their early 20s having um they're all in their early 20s having um they're all in their early 20s so they're all trying to find it. like I so they're all trying to find it. like I so they're all trying to find it. like I don't know if they're all even there don't know if they're all even there don't know if they're all even there yet, but there is this intuition as a yet, but there is this intuition as a yet, but there is this intuition as a parent and I I think it's well parent and I I think it's well parent and I I think it's well intentioned to to to worry to feel like intentioned to to to worry to feel like intentioned to to to worry to feel like they're on a safe path and safe is they're on a safe path and safe is they're on a safe path and safe is usually economic, but it's also uh it's usually economic, but it's also uh it's usually economic, but it's also uh it's just risk feels like your risk like like just risk feels like your risk like like just risk feels like your risk like like and and I I love the story of what your and and I I love the story of what your and and I I love the story of what your parents did and I've got a few anecdotes parents did and I've got a few anecdotes parents did and I've got a few anecdotes I found since we finished the book that I found since we finished the book that I found since we finished the book that are great on that are very similar to are great on that are very similar to are great on that are very similar to what your parents did, but I think it's what your parents did, but I think it's what your parents did, but I think it's the exception. I don't think it's the the exception. I don't think it's the the exception. I don't think it's the rule. I think a lot of parents would rule. I think a lot of parents would rule. I think a lot of parents would have tried to convince you to finish out have tried to convince you to finish out have tried to convince you to finish out and get your degree. I think that's and get your degree. I think that's and get your degree. I think that's built into to most uh parents and and so built into to most uh parents and and so built into to most uh parents and and so there are other people other than myself there are other people other than myself there are other people other than myself that that have highlighted that the that that have highlighted that the that that have highlighted that the I'd call it like this industrial college I'd call it like this industrial college I'd call it like this industrial college metriculation path has gotten very rigid metriculation path has gotten very rigid metriculation path has gotten very rigid and and it's competitive and it's and and it's competitive and it's and and it's competitive and it's grindy, grindy, grindy, >> man. the the co like getting into >> man. the the co like getting into >> man. the the co like getting into college now is significantly harder. college now is significantly harder. college now is significantly harder. >> Yeah, they've not expanded they have not >> Yeah, they've not expanded they have not >> Yeah, they've not expanded they have not expanded the uh enrollment at these expanded the uh enrollment at these expanded the uh enrollment at these schools, but the number of people that schools, but the number of people that schools, but the number of people that want to go to college has gone way up. want to go to college has gone way up. want to go to college has gone way up. >> It's crazy. >> It's crazy. >> It's crazy. >> It's crazy. And and starting around >> It's crazy. And and starting around >> It's crazy. And and starting around sixth grade, once again, sixth grade, once again, sixth grade, once again, well-intentioned parents start building well-intentioned parents start building well-intentioned parents start building the resume to get into college. And so the resume to get into college. And so the resume to get into college. And so we overschedu children today compared to we overschedu children today compared to we overschedu children today compared to when I was young. when I was young. when I was young. >> For sure. And so they're they're >> For sure. And so they're they're >> For sure. And so they're they're scheduled from when they wake up to when scheduled from when they wake up to when scheduled from when they wake up to when and they go to bed. There's actually a and they go to bed. There's actually a and they go to bed. There's actually a chapter in Jonathan Height's book chapter in Jonathan Height's book chapter in Jonathan Height's book Codling of the American Mind called the Codling of the American Mind called the Codling of the American Mind called the decline of play where we've just we've decline of play where we've just we've decline of play where we've just we've we it's harder, I think, for a child to we it's harder, I think, for a child to we it's harder, I think, for a child to explore and try on different ideas um explore and try on different ideas um explore and try on different ideas um because they're caught up in this game because they're caught up in this game because they're caught up in this game to try and get into college. to try and get into college. to try and get into college. >> You had this crazy stat. You said um I >> You had this crazy stat. You said um I >> You had this crazy stat. You said um I think it was uh the people who won a think it was uh the people who won a think it was uh the people who won a Nobel Prize in science, the scientists Nobel Prize in science, the scientists Nobel Prize in science, the scientists who won Nobel prizes, correct me if I'm who won Nobel prizes, correct me if I'm who won Nobel prizes, correct me if I'm wrong, but they were 22 times more wrong, but they were 22 times more wrong, but they were 22 times more likely to participate in things like likely to participate in things like likely to participate in things like acting or dance class and things like acting or dance class and things like acting or dance class and things like that. What was that stat? So this was that. What was that stat? So this was that. What was that stat? So this was work that Keith Holio had done at UCLA work that Keith Holio had done at UCLA work that Keith Holio had done at UCLA and it relates to a lot of the concepts and it relates to a lot of the concepts and it relates to a lot of the concepts in the back of range the book by David in the back of range the book by David in the back of range the book by David Epstein but it it was the people at the Epstein but it it was the people at the Epstein but it it was the people at the top of their field um are like much more top of their field um are like much more top of their field um are like much more likely to have a a breadth of hobbies um likely to have a a breadth of hobbies um likely to have a a breadth of hobbies um speak more languages do more things um speak more languages do more things um speak more languages do more things um and and and and and and almost I think have a lens on the world almost I think have a lens on the world almost I think have a lens on the world that's broader because they were able to that's broader because they were able to that's broader because they were able to try so many different things. try so many different things. try so many different things. >> So I read this book uh mastery and like >> So I read this book uh mastery and like >> So I read this book uh mastery and like the premise is like being a generalist the premise is like being a generalist the premise is like being a generalist is kind of nonsense. You have to is kind of nonsense. You have to is kind of nonsense. You have to specialize in something but once you specialize in something but once you specialize in something but once you specialize then you become a generalist. specialize then you become a generalist. specialize then you become a generalist. I think that's the right pathway like I I think that's the right pathway like I I think that's the right pathway like I I do think you want to get started in an I do think you want to get started in an I do think you want to get started in an area where you can differentiate area where you can differentiate area where you can differentiate yourself and then and in many in both yourself and then and in many in both yourself and then and in many in both the principal chapter on mentors and the principal chapter on mentors and the principal chapter on mentors and peers in here and even in the learning peers in here and even in the learning peers in here and even in the learning uh principle I recommend you know as a uh principle I recommend you know as a uh principle I recommend you know as a more advanced level once you get you more advanced level once you get you more advanced level once you get you know up to this level then go broader know up to this level then go broader know up to this level then go broader like start to learn outside your field like start to learn outside your field like start to learn outside your field find mentors and peers outside your find mentors and peers outside your find mentors and peers outside your field and you'll get pulled in more field and you'll get pulled in more field and you'll get pulled in more innovative creative ways. innovative creative ways. innovative creative ways. >> So, tell tell me more about that. That >> So, tell tell me more about that. That >> So, tell tell me more about that. That like just kind of blew my mind. like just kind of blew my mind. like just kind of blew my mind. >> Well, I think what Keith's work um >> Well, I think what Keith's work um >> Well, I think what Keith's work um highlighted was that some of the people highlighted was that some of the people highlighted was that some of the people that are able to reach the top of their that are able to reach the top of their that are able to reach the top of their field are able to draw on mental models field are able to draw on mental models field are able to draw on mental models from much from a variety of different from much from a variety of different from much from a variety of different places and where a hypers specialist and places and where a hypers specialist and places and where a hypers specialist and and David Epstein's book range is all and David Epstein's book range is all and David Epstein's book range is all about this specialist versus broad about this specialist versus broad about this specialist versus broad thing. Like that's the really the the thing. Like that's the really the the thing. Like that's the really the the whole point of the book and he quotes whole point of the book and he quotes whole point of the book and he quotes Holio as well. But many different Holio as well. But many different Holio as well. But many different innovations in science have come from innovations in science have come from innovations in science have come from people who repotted from one place to people who repotted from one place to people who repotted from one place to another. A chemist who becomes a another. A chemist who becomes a another. A chemist who becomes a physicist. The person who's a lifelong physicist. The person who's a lifelong physicist. The person who's a lifelong physicist has mental models that are physicist has mental models that are physicist has mental models that are pretty rigid at that point in time pretty rigid at that point in time pretty rigid at that point in time because that's all they know. And so because that's all they know. And so because that's all they know. And so once again, I think this is an advanced once again, I think this is an advanced once again, I think this is an advanced skill. I don't I think after you're skill. I don't I think after you're skill. I don't I think after you're succeeding, you start to do this. I succeeding, you start to do this. I succeeding, you start to do this. I don't think it's the pathway to the don't think it's the pathway to the don't think it's the pathway to the beginning of success because I think beginning of success because I think beginning of success because I think you'd just be too broad. But some of the you'd just be too broad. But some of the you'd just be too broad. But some of the smartest people I know could like like smartest people I know could like like smartest people I know could like like one person profile in the book is Danny one person profile in the book is Danny one person profile in the book is Danny Meyer, the great restaurant tour. we Meyer, the great restaurant tour. we Meyer, the great restaurant tour. we were asking him about his mentors and were asking him about his mentors and were asking him about his mentors and one of the mentors that influenced him one of the mentors that influenced him one of the mentors that influenced him the most isn't from the restaurant the most isn't from the restaurant the most isn't from the restaurant industry you know and so it's uh it it industry you know and so it's uh it it industry you know and so it's uh it it is a more advanced skill but it is where is a more advanced skill but it is where is a more advanced skill but it is where you will look the whole goal I think is you will look the whole goal I think is you will look the whole goal I think is to differentiate yourself along the to differentiate yourself along the to differentiate yourself along the pathway and that is a great way more pathway and that is a great way more pathway and that is a great way more advanced way but a great way to to take advanced way but a great way to to take advanced way but a great way to to take yourself places you wouldn't have yourself places you wouldn't have yourself places you wouldn't have thought of thought of thought of >> you had this cool line you said there's >> you had this cool line you said there's >> you had this cool line you said there's if there's one takeaway that you should if there's one takeaway that you should if there's one takeaway that you should have from this book peer groups more so have from this book peer groups more so have from this book peer groups more so than coaching, consulting courses, than coaching, consulting courses, than coaching, consulting courses, whatever, is probably the most powerful whatever, is probably the most powerful whatever, is probably the most powerful thing that you could use. And it's under thing that you could use. And it's under thing that you could use. And it's under discussed because it doesn't feel discussed because it doesn't feel discussed because it doesn't feel intuitive to like want to be peers with intuitive to like want to be peers with intuitive to like want to be peers with someone who might take the same job as someone who might take the same job as someone who might take the same job as you, but it's really powerful. you, but it's really powerful. you, but it's really powerful. >> I think the way you describe it is right >> I think the way you describe it is right >> I think the way you describe it is right like everyone talks about mentors and no like everyone talks about mentors and no like everyone talks about mentors and no one talks about peers. So, I do have a one talks about peers. So, I do have a one talks about peers. So, I do have a chapter on mentors and I offer a ton of chapter on mentors and I offer a ton of chapter on mentors and I offer a ton of very practical advice about how to play very practical advice about how to play very practical advice about how to play that correctly. But the peer thing, the that correctly. But the peer thing, the that correctly. But the peer thing, the idea is that when you get on that first idea is that when you get on that first idea is that when you get on that first rung of the ladder and you're trying to rung of the ladder and you're trying to rung of the ladder and you're trying to climb it, if you could develop a friend climb it, if you could develop a friend climb it, if you could develop a friend group, it might be four, it might be six group, it might be four, it might be six group, it might be four, it might be six that are also on that same journey and that are also on that same journey and that are also on that same journey and hopefully I think outside your hopefully I think outside your hopefully I think outside your organization. I think you could start organization. I think you could start organization. I think you could start maybe with one person in your org, but maybe with one person in your org, but maybe with one person in your org, but for all the reasons we just talked about for all the reasons we just talked about for all the reasons we just talked about how breath of knowledge might give you how breath of knowledge might give you how breath of knowledge might give you insights you wouldn't have, if they're insights you wouldn't have, if they're insights you wouldn't have, if they're outside your org, they're going to see outside your org, they're going to see outside your org, they're going to see different cultures. They're going to see different cultures. They're going to see different cultures. They're going to see different management structures. They're different management structures. They're different management structures. They're going to bring a different viewpoint to going to bring a different viewpoint to going to bring a different viewpoint to you that you wouldn't have had if they you that you wouldn't have had if they you that you wouldn't have had if they were inside. Um, and then with today's were inside. Um, and then with today's were inside. Um, and then with today's modern tools, you know, created create modern tools, you know, created create modern tools, you know, created create if you're adventurous, create a Slack if you're adventurous, create a Slack if you're adventurous, create a Slack channel. If you're if you just want to channel. If you're if you just want to channel. If you're if you just want to do a WhatsApp group or a signal group do a WhatsApp group or a signal group do a WhatsApp group or a signal group and share, you know, share your and share, you know, share your and share, you know, share your learnings along the way. learnings along the way. learnings along the way. >> When I moved to San Francisco for >> When I moved to San Francisco for >> When I moved to San Francisco for Airbnb, it um I didn't actually end up Airbnb, it um I didn't actually end up Airbnb, it um I didn't actually end up getting the job, by the way. They getting the job, by the way. They getting the job, by the way. They offered me a job and I got it. And then offered me a job and I got it. And then offered me a job and I got it. And then when I was in college, I was like kind when I was in college, I was like kind when I was in college, I was like kind of crazy and I got arrested. I got DUI of crazy and I got arrested. I got DUI of crazy and I got arrested. I got DUI and I'm sober now. I don't do any drugs and I'm sober now. I don't do any drugs and I'm sober now. I don't do any drugs or alcohol. I'm completely clean and and or alcohol. I'm completely clean and and or alcohol. I'm completely clean and and by the book, but they were like, "You by the book, but they were like, "You by the book, but they were like, "You lied on your resume. You said you didn't lied on your resume. You said you didn't lied on your resume. You said you didn't have a a criminal record." And so I have a a criminal record." And so I have a a criminal record." And so I didn't end up getting to start. And so I didn't end up getting to start. And so I didn't end up getting to start. And so I was stuck out in San Francisco. I was was stuck out in San Francisco. I was was stuck out in San Francisco. I was like, "What the hell am I going to do?" like, "What the hell am I going to do?" like, "What the hell am I going to do?" So I ended up starting a company and it So I ended up starting a company and it So I ended up starting a company and it worked out well, but it was like super worked out well, but it was like super worked out well, but it was like super low point in my life. And when I got low point in my life. And when I got low point in my life. And when I got there, I created this thing called the there, I created this thing called the there, I created this thing called the antiMBA. antiMBA. antiMBA. It was my version of a book club. and we It was my version of a book club. and we It was my version of a book club. and we met once a week and we would get a book met once a week and we would get a book met once a week and we would get a book and we would read a book a month and and we would read a book a month and and we would read a book a month and talk about a quarter of the book every talk about a quarter of the book every talk about a quarter of the book every single week and it changed my life like single week and it changed my life like single week and it changed my life like having those group of guys to like and I having those group of guys to like and I having those group of guys to like and I think that like you need a few things to think that like you need a few things to think that like you need a few things to make a group like that work. I think you make a group like that work. I think you make a group like that work. I think you need like rules, you need like some need like rules, you need like some need like rules, you need like some rituals and you need to like take it rituals and you need to like take it rituals and you need to like take it serious. serious. serious. >> Yeah. And I think if there are people >> Yeah. And I think if there are people >> Yeah. And I think if there are people that are sharp elbowed or climbers that that are sharp elbowed or climbers that that are sharp elbowed or climbers that that step on other people, you kick them that step on other people, you kick them that step on other people, you kick them out. Like I I I think you need out. Like I I I think you need out. Like I I I think you need like-minded people who are equally like-minded people who are equally like-minded people who are equally gracious to one another. gracious to one another. gracious to one another. >> Who's in your group now? That's like uh >> Who's in your group now? That's like uh >> Who's in your group now? That's like uh shot now. shot now. shot now. >> Well, we >> Well, we >> Well, we one thing I've I've I've discovered one thing I've I've I've discovered one thing I've I've I've discovered lately is setting up different like lately is setting up different like lately is setting up different like WhatsApp or signal groups for different WhatsApp or signal groups for different WhatsApp or signal groups for different topics. I think for someone coming early topics. I think for someone coming early topics. I think for someone coming early into a career, it's better to have into a career, it's better to have into a career, it's better to have people that are on that exact journey. people that are on that exact journey. people that are on that exact journey. And I'm not in that place anymore. And I'm not in that place anymore. And I'm not in that place anymore. >> I have a company called Hampton. That's >> I have a company called Hampton. That's >> I have a company called Hampton. That's my main company. my main company. my main company. >> Are you familiar with YPO? >> Are you familiar with YPO? >> Are you familiar with YPO? >> Sure. >> Sure. >> Sure. >> That's like YPO. So, we have thousands >> That's like YPO. So, we have thousands >> That's like YPO. So, we have thousands of members all over the country and you of members all over the country and you of members all over the country and you >> It's creates peer group >> It's creates peer group >> It's creates peer group >> and then we have executive coaches who >> and then we have executive coaches who >> and then we have executive coaches who like lead the conversation. like lead the conversation. like lead the conversation. >> It's for CEOs. So, you have like the >> It's for CEOs. So, you have like the >> It's for CEOs. So, you have like the average person has like 30 million 20 average person has like 30 million 20 average person has like 30 million 20 million in revenue or so. And it's been million in revenue or so. And it's been million in revenue or so. And it's been really cool to like watch these members really cool to like watch these members really cool to like watch these members like team and I'm in a a peer uh core we like team and I'm in a a peer uh core we like team and I'm in a a peer uh core we call them core groups. I'm in one as call them core groups. I'm in one as call them core groups. I'm in one as well. And it like you have this uh a well. And it like you have this uh a well. And it like you have this uh a bunch of lines in there about peer bunch of lines in there about peer bunch of lines in there about peer groups and I'm like, "Oh, you're writing groups and I'm like, "Oh, you're writing groups and I'm like, "Oh, you're writing my ads for me." my ads for me." my ads for me." >> Yeah. But but but and those things exist >> Yeah. But but but and those things exist >> Yeah. But but but and those things exist with YPO and and your thing for CEOs, with YPO and and your thing for CEOs, with YPO and and your thing for CEOs, but it could be done by anybody but it could be done by anybody but it could be done by anybody >> for sure. I mean like my wife when she >> for sure. I mean like my wife when she >> for sure. I mean like my wife when she was pregnant, she had one for moms. was pregnant, she had one for moms. was pregnant, she had one for moms. >> Uh I've got a a buddy of mine has one >> Uh I've got a a buddy of mine has one >> Uh I've got a a buddy of mine has one for Jewish dads. Like like it could be for Jewish dads. Like like it could be for Jewish dads. Like like it could be anything. You know what I mean? But like anything. You know what I mean? But like anything. You know what I mean? But like it really does like change things. it really does like change things. it really does like change things. >> It does. It really does. I think it can. >> It does. It really does. I think it can. >> It does. It really does. I think it can. Uh and and almost all of the other Uh and and almost all of the other Uh and and almost all of the other principles are accelerated. So your principles are accelerated. So your principles are accelerated. So your learning is accelerated. There's a great learning is accelerated. There's a great learning is accelerated. There's a great story in the book about Mr. Beast that story in the book about Mr. Beast that story in the book about Mr. Beast that ties to that. There's uh your your your ties to that. There's uh your your your ties to that. There's uh your your your network is accelerated. So your network network is accelerated. So your network network is accelerated. So your network isn't just your network. It's now the isn't just your network. It's now the isn't just your network. It's now the network of the group if people are network of the group if people are network of the group if people are willing to share introductions and that willing to share introductions and that willing to share introductions and that kind of thing. You know, both for kind of thing. You know, both for kind of thing. You know, both for mentors and other peers and and then the mentors and other peers and and then the mentors and other peers and and then the group I think can be really helpful on group I think can be really helpful on group I think can be really helpful on bad days. And everyone's going to have bad days. And everyone's going to have bad days. And everyone's going to have bad days and there's a support element bad days and there's a support element bad days and there's a support element that comes in into play that I think is that comes in into play that I think is that comes in into play that I think is really useful. And then also you you may really useful. And then also you you may really useful. And then also you you may be at a shitty company. Like your your be at a shitty company. Like your your be at a shitty company. Like your your dream job may be the one you're in and dream job may be the one you're in and dream job may be the one you're in and you might be at a shitty company. And if you might be at a shitty company. And if you might be at a shitty company. And if you're alone, you have no way of knowing you're alone, you have no way of knowing you're alone, you have no way of knowing if that's normal or not. Like the the if that's normal or not. Like the the if that's normal or not. Like the the stuff you're exposed to. Whereas if you stuff you're exposed to. Whereas if you stuff you're exposed to. Whereas if you had a group of eight people that were had a group of eight people that were had a group of eight people that were all doing this in different companies, all doing this in different companies, all doing this in different companies, you'd get different perspectives on you'd get different perspectives on you'd get different perspectives on that. that. that. >> What did the voice to you say when it >> What did the voice to you say when it >> What did the voice to you say when it was like I found my calling? There was a was like I found my calling? There was a was like I found my calling? There was a lack of that voice that kept asking, "Is lack of that voice that kept asking, "Is lack of that voice that kept asking, "Is this what you want to be doing 30 years this what you want to be doing 30 years this what you want to be doing 30 years from now?" Like that that worry was from now?" Like that that worry was from now?" Like that that worry was gone. Like I I wasn't having those gone. Like I I wasn't having those gone. Like I I wasn't having those negative thoughts, if you will. negative thoughts, if you will. negative thoughts, if you will. >> And what was the thing that you're >> And what was the thing that you're >> And what was the thing that you're doing? Investing. doing? Investing. doing? Investing. >> Yeah. Once I became a VC, I just adored >> Yeah. Once I became a VC, I just adored >> Yeah. Once I became a VC, I just adored every minute of the job. It um but a lot every minute of the job. It um but a lot every minute of the job. It um but a lot of that fitting my individual of that fitting my individual of that fitting my individual personality. you know, there are people personality. you know, there are people personality. you know, there are people who, you know, are kind of they go, "Ah, who, you know, are kind of they go, "Ah, who, you know, are kind of they go, "Ah, you can't be a VC because you're not the you can't be a VC because you're not the you can't be a VC because you're not the one actually doing the work." That never one actually doing the work." That never one actually doing the work." That never bothered me. You know, I'm someone who's bothered me. You know, I'm someone who's bothered me. You know, I'm someone who's really drawn to intellectual breath. And really drawn to intellectual breath. And really drawn to intellectual breath. And so, a service job, whether it's working so, a service job, whether it's working so, a service job, whether it's working in banking or working as a VC, gives me in banking or working as a VC, gives me in banking or working as a VC, gives me a window across way more companies than a window across way more companies than a window across way more companies than if I were working in one. And I also I'm if I were working in one. And I also I'm if I were working in one. And I also I'm fairly certain I have ADD and like fairly certain I have ADD and like fairly certain I have ADD and like focusing on details is not something I'm focusing on details is not something I'm focusing on details is not something I'm good at. Man, whenever you when I've good at. Man, whenever you when I've good at. Man, whenever you when I've heard Jeff Bezos or Warren Buffet, heard Jeff Bezos or Warren Buffet, heard Jeff Bezos or Warren Buffet, someone was like, "I tap dance to work someone was like, "I tap dance to work someone was like, "I tap dance to work every day." And then you're you're every day." And then you're you're every day." And then you're you're saying you adored every minute of it. saying you adored every minute of it. saying you adored every minute of it. It's like I think I found my passion, It's like I think I found my passion, It's like I think I found my passion, but like I probably like running a but like I probably like running a but like I probably like running a company, it sucks like 85% of the time. company, it sucks like 85% of the time. company, it sucks like 85% of the time. And like my last company that sold it And like my last company that sold it And like my last company that sold it was great. Like if you talk to my wife, was great. Like if you talk to my wife, was great. Like if you talk to my wife, she was like, "You laid on the floor she was like, "You laid on the floor she was like, "You laid on the floor like all the time saying I can't do like all the time saying I can't do like all the time saying I can't do this. I want to quit. This sucks." this. I want to quit. This sucks." this. I want to quit. This sucks." >> Like is adored every second of it the >> Like is adored every second of it the >> Like is adored every second of it the right is that accurate? I I'm I'm right is that accurate? I I'm I'm right is that accurate? I I'm I'm telling you the expost kind of um telling you the expost kind of um telling you the expost kind of um summary of it all. summary of it all. summary of it all. >> But like how many times when you were >> But like how many times when you were >> But like how many times when you were doing it did you want to quit? doing it did you want to quit? doing it did you want to quit? >> I don't ever remember wanting to quit. >> I don't ever remember wanting to quit. >> I don't ever remember wanting to quit. >> Really? >> Really? >> Really? >> Really? >> Really? >> Really? >> That makes me feel horrible. >> That makes me feel horrible. >> That makes me feel horrible. >> I think the CEO jobs the loneliest job >> I think the CEO jobs the loneliest job >> I think the CEO jobs the loneliest job in America. I've said that many many in America. I've said that many many in America. I've said that many many times before. It's hard. And one of the times before. It's hard. And one of the times before. It's hard. And one of the things that makes it particularly hard, things that makes it particularly hard, things that makes it particularly hard, you need to run culturally opposite you need to run culturally opposite you need to run culturally opposite what's happening at the company. So if what's happening at the company. So if what's happening at the company. So if the company's doing poorly, you have to the company's doing poorly, you have to the company's doing poorly, you have to bring the positive energy and make bring the positive energy and make bring the positive energy and make people believe it's possible. And if the people believe it's possible. And if the people believe it's possible. And if the company's running hot, you want to bring company's running hot, you want to bring company's running hot, you want to bring them down to earth. And this is my this them down to earth. And this is my this them down to earth. And this is my this is my theory on why the CEO job so hard. is my theory on why the CEO job so hard. is my theory on why the CEO job so hard. So running counter emotionally to what So running counter emotionally to what So running counter emotionally to what everybody else in the organization feels everybody else in the organization feels everybody else in the organization feels is exhausting. is exhausting. is exhausting. >> It's exhausting in a world where like I >> It's exhausting in a world where like I >> It's exhausting in a world where like I I've I've grown to dislike the word and I've I've grown to dislike the word and I've I've grown to dislike the word and the idea of authenticity. It's sort of the idea of authenticity. It's sort of the idea of authenticity. It's sort of like when you're a young kid and you're like when you're a young kid and you're like when you're a young kid and you're trying to meet girls. People say just be trying to meet girls. People say just be trying to meet girls. People say just be yourself. And I'm like girls don't like yourself. And I'm like girls don't like yourself. And I'm like girls don't like myself. Like I want to be myself. Like I myself. Like I want to be myself. Like I myself. Like I want to be myself. Like I need to change and be better. need to change and be better. need to change and be better. And then people are like be authentic. And then people are like be authentic. And then people are like be authentic. And I'm like but I'm not a good leader. And I'm like but I'm not a good leader. And I'm like but I'm not a good leader. I need to be better. You know what I I need to be better. You know what I I need to be better. You know what I mean? And so they'll be like be mean? And so they'll be like be mean? And so they'll be like be authentic. Like be transparent with your authentic. Like be transparent with your authentic. Like be transparent with your team. Tell them that you're not feeling team. Tell them that you're not feeling team. Tell them that you're not feeling great. I'm like no lie. Like you have to great. I'm like no lie. Like you have to great. I'm like no lie. Like you have to like convince them that like we're going like convince them that like we're going like convince them that like we're going to figure this out and somehow you will to figure this out and somehow you will to figure this out and somehow you will you know what I mean? you know what I mean? you know what I mean? >> I do. Leadership's really really hard. I >> I do. Leadership's really really hard. I >> I do. Leadership's really really hard. I think one of the things that um is often think one of the things that um is often think one of the things that um is often not talked about enough in the the whole not talked about enough in the the whole not talked about enough in the the whole both Silicon Valley and just the the uh both Silicon Valley and just the the uh both Silicon Valley and just the the uh celebration of the founder is that that celebration of the founder is that that celebration of the founder is that that if you're successful and your company if you're successful and your company if you're successful and your company grows, you're going to go from 10 grows, you're going to go from 10 grows, you're going to go from 10 employees to 100 employees to a thousand employees to 100 employees to a thousand employees to 100 employees to a thousand employees and eventually leadership's employees and eventually leadership's employees and eventually leadership's going to be required and matter. And you going to be required and matter. And you going to be required and matter. And you don't have a place to learn that. You don't have a place to learn that. You don't have a place to learn that. You know, it's not there's no book that he know, it's not there's no book that he know, it's not there's no book that he teaches, oh, here you're a founder. You teaches, oh, here you're a founder. You teaches, oh, here you're a founder. You want to learn to lead people like and want to learn to lead people like and want to learn to lead people like and it's not discussed much, but but the it's not discussed much, but but the it's not discussed much, but but the Zuckerbergs of the world. I know for a Zuckerbergs of the world. I know for a Zuckerbergs of the world. I know for a fact that Larry and Sergey, there's this fact that Larry and Sergey, there's this fact that Larry and Sergey, there's this gentleman named Bill Campbell who gentleman named Bill Campbell who gentleman named Bill Campbell who unfortunately passed. He unfortunately passed. He unfortunately passed. He >> trillion dollar coach. >> trillion dollar coach. >> trillion dollar coach. >> Yes. Campbell was there 10 years after >> Yes. Campbell was there 10 years after >> Yes. Campbell was there 10 years after the IPO, he was still running the weekly the IPO, he was still running the weekly the IPO, he was still running the weekly team meetings with Larry and Sergey. team meetings with Larry and Sergey. team meetings with Larry and Sergey. >> Were they just bad leaders? I mean, what >> Were they just bad leaders? I mean, what >> Were they just bad leaders? I mean, what what what what >> I don't know. Steve Jobs used Bill also. >> I don't know. Steve Jobs used Bill also. >> I don't know. Steve Jobs used Bill also. So I I don't know that that makes him So I I don't know that that makes him So I I don't know that that makes him bad. I I'm just highlighting the fact bad. I I'm just highlighting the fact bad. I I'm just highlighting the fact that there's no reason from a DNA that there's no reason from a DNA that there's no reason from a DNA standpoint that a founder should standpoint that a founder should standpoint that a founder should naturally be able to lead a thousand naturally be able to lead a thousand naturally be able to lead a thousand people because there's a skill set people because there's a skill set people because there's a skill set required to lead a thousand people and required to lead a thousand people and required to lead a thousand people and no one's taught it to you. no one's taught it to you. no one's taught it to you. >> Can you learn it? >> Can you learn it? >> Can you learn it? >> Yeah, I think you can learn it. I think >> Yeah, I think you can learn it. I think >> Yeah, I think you can learn it. I think certain people have. I think certain people have. I think certain people have. I think Zuckerberg's learned it. I think Bezos Zuckerberg's learned it. I think Bezos Zuckerberg's learned it. I think Bezos didn't have any leadership skills going didn't have any leadership skills going didn't have any leadership skills going in. Like he had never run a large team in. Like he had never run a large team in. Like he had never run a large team before. What do you suggest to someone before. What do you suggest to someone before. What do you suggest to someone to learn how to be a better leader? to learn how to be a better leader? to learn how to be a better leader? >> Get to know Bill Campbell, but that is >> Get to know Bill Campbell, but that is >> Get to know Bill Campbell, but that is no longer with us. So, um, you know, I' no longer with us. So, um, you know, I' no longer with us. So, um, you know, I' I've often said, um, get two or three I've often said, um, get two or three I've often said, um, get two or three mentors that have ran large groups. They mentors that have ran large groups. They mentors that have ran large groups. They will all have their leadership will all have their leadership will all have their leadership philosophy and patterns and try those on philosophy and patterns and try those on philosophy and patterns and try those on and see which one fits you the best. So and see which one fits you the best. So and see which one fits you the best. So maybe that's maybe in the middle between maybe that's maybe in the middle between maybe that's maybe in the middle between between the authentic and not like you between the authentic and not like you between the authentic and not like you having a programming philosophy is having a programming philosophy is having a programming philosophy is better than none. I can't tell you how better than none. I can't tell you how better than none. I can't tell you how many founders have gotten to like 200 many founders have gotten to like 200 many founders have gotten to like 200 employees and they're not running a employees and they're not running a employees and they're not running a weekly meeting like they don't know to weekly meeting like they don't know to weekly meeting like they don't know to do it. So some structure is better than do it. So some structure is better than do it. So some structure is better than no structure. And therefore, rather than no structure. And therefore, rather than no structure. And therefore, rather than say one of those CEOs you talked to is say one of those CEOs you talked to is say one of those CEOs you talked to is absolutely right, find out what they're absolutely right, find out what they're absolutely right, find out what they're doing and see which one feels best for doing and see which one feels best for doing and see which one feels best for you and your or you and your or you and your or >> Well, you talked about that with with uh >> Well, you talked about that with with uh >> Well, you talked about that with with uh Danny Meyer. Uh Danny Meyer, I think Danny Meyer. Uh Danny Meyer, I think Danny Meyer. Uh Danny Meyer, I think probably most known outside of New York probably most known outside of New York probably most known outside of New York for running Shake Shack. You said that for running Shake Shack. You said that for running Shake Shack. You said that um I think he was going to be a lawyer um I think he was going to be a lawyer um I think he was going to be a lawyer or something and he and he and he hated or something and he and he and he hated or something and he and he and he hated it. But he went and toured a bunch his it. But he went and toured a bunch his it. But he went and toured a bunch his uncle was like, "Dude, what are you uncle was like, "Dude, what are you uncle was like, "Dude, what are you doing? You got to be you got to get in doing? You got to be you got to get in doing? You got to be you got to get in the restaurant business." And so what he the restaurant business." And so what he the restaurant business." And so what he did was he did like a field trip to like did was he did like a field trip to like did was he did like a field trip to like tour restaurants and then eventually got tour restaurants and then eventually got tour restaurants and then eventually got a part-time job as uh working at a a part-time job as uh working at a a part-time job as uh working at a restaurant before starting his restaurant before starting his restaurant before starting his restaurant. restaurant. restaurant. >> Yeah. He also did a tour through Europe >> Yeah. He also did a tour through Europe >> Yeah. He also did a tour through Europe as a stash which is a fancy word for as a stash which is a fancy word for as a stash which is a fancy word for work for free. work for free. work for free. >> But you in the book you're like he still >> But you in the book you're like he still >> But you in the book you're like he still does that. So like whenever like they're does that. So like whenever like they're does that. So like whenever like they're opening up a new restaurant he goes and opening up a new restaurant he goes and opening up a new restaurant he goes and like field trips and then you're like like field trips and then you're like like field trips and then you're like when he opened up I think a barbecue when he opened up I think a barbecue when he opened up I think a barbecue place he like went back to St. Louis and place he like went back to St. Louis and place he like went back to St. Louis and like tested stuff. Is there a world like tested stuff. Is there a world like tested stuff. Is there a world where like a white collar job uh person where like a white collar job uh person where like a white collar job uh person can take these field trips? Like can take these field trips? Like can take these field trips? Like >> I think so or or at least the notion of >> I think so or or at least the notion of >> I think so or or at least the notion of it I one of the arguments I make like it I one of the arguments I make like it I one of the arguments I make like pound the table in in the learning pound the table in in the learning pound the table in in the learning chapter is that most people don't think chapter is that most people don't think chapter is that most people don't think about continuous learning in their job. about continuous learning in their job. about continuous learning in their job. Now the the founders do because they're Now the the founders do because they're Now the the founders do because they're learning these new technologies and learning these new technologies and learning these new technologies and maybe doctors do because it's required maybe doctors do because it's required maybe doctors do because it's required by law, but most people that get into a by law, but most people that get into a by law, but most people that get into a field I think I think the college field I think I think the college field I think I think the college experience and the high school experience and the high school experience and the high school experience were so exhausting they're experience were so exhausting they're experience were so exhausting they're like worn out and they're like I'm glad like worn out and they're like I'm glad like worn out and they're like I'm glad I'm done learning and then they're going I'm done learning and then they're going I'm done learning and then they're going to go to work. But whatever you do, I to go to work. But whatever you do, I to go to work. But whatever you do, I guarantee you, especially with AI out guarantee you, especially with AI out guarantee you, especially with AI out there, there's some nuance of what you there, there's some nuance of what you there, there's some nuance of what you could be doing that's new. And and could be doing that's new. And and could be doing that's new. And and unless you're trying to find that edge, unless you're trying to find that edge, unless you're trying to find that edge, somebody else may be. And I think the somebody else may be. And I think the somebody else may be. And I think the people most at threat by AI are the ones people most at threat by AI are the ones people most at threat by AI are the ones that aren't continuously learning, that that aren't continuously learning, that that aren't continuously learning, that are just kind of doing the same thing are just kind of doing the same thing are just kind of doing the same thing they did 10 years ago because they're they did 10 years ago because they're they did 10 years ago because they're they're kind of a widget, you know, and they're kind of a widget, you know, and they're kind of a widget, you know, and that could be automated. And the people that could be automated. And the people that could be automated. And the people that that are curious about what's that that are curious about what's that that are curious about what's possible, they're naturally going to see possible, they're naturally going to see possible, they're naturally going to see this AI thing pop up and go, "Wow, this AI thing pop up and go, "Wow, this AI thing pop up and go, "Wow, that's a new tool. I better figure out that's a new tool. I better figure out that's a new tool. I better figure out what it can do for me." And those are what it can do for me." And those are what it can do for me." And those are the people that are hardest to replace. the people that are hardest to replace. the people that are hardest to replace. Like if your if your company's trying to Like if your if your company's trying to Like if your if your company's trying to figure out AI and one of your employees figure out AI and one of your employees figure out AI and one of your employees is spending more time on it than is spending more time on it than is spending more time on it than everybody else, they're the last person everybody else, they're the last person everybody else, they're the last person you're going to fire. I think that like you're going to fire. I think that like you're going to fire. I think that like what I've been trying to tell a lot of what I've been trying to tell a lot of what I've been trying to tell a lot of like we have a lot of young people like we have a lot of young people like we have a lot of young people listen particularly a lot of young men listen particularly a lot of young men listen particularly a lot of young men and I'm like you have to understand the and I'm like you have to understand the and I'm like you have to understand the difference between risk and uncertainty difference between risk and uncertainty difference between risk and uncertainty and that risk is often times a lot less and that risk is often times a lot less and that risk is often times a lot less than people think but uncertainty will than people think but uncertainty will than people think but uncertainty will always exist no matter what and you just always exist no matter what and you just always exist no matter what and you just have to get comfortable with that and I have to get comfortable with that and I have to get comfortable with that and I think that in order to reduce risk I think that in order to reduce risk I think that in order to reduce risk I don't think people realize how many don't think people realize how many don't think people realize how many things in life they can try before they things in life they can try before they things in life they can try before they buy for example I moved from Texas up buy for example I moved from Texas up buy for example I moved from Texas up here here here >> I rented an Airbnb for 2 weeks in a >> I rented an Airbnb for 2 weeks in a >> I rented an Airbnb for 2 weeks in a neighborhood ood that I wanted to see neighborhood ood that I wanted to see neighborhood ood that I wanted to see and like I tested it out and I actually and like I tested it out and I actually and like I tested it out and I actually realized I hated that neighborhood but I realized I hated that neighborhood but I realized I hated that neighborhood but I like this other area. like this other area. like this other area. >> Yeah. >> Yeah. >> Yeah. >> Or like you could do that. I remember >> Or like you could do that. I remember >> Or like you could do that. I remember before I wanted to at one time I wanted before I wanted to at one time I wanted before I wanted to at one time I wanted to buy a fancy car. I tested it on Toro to buy a fancy car. I tested it on Toro to buy a fancy car. I tested it on Toro >> and I was like I don't want to own this >> and I was like I don't want to own this >> and I was like I don't want to own this car. This is a pain in the ass. car. This is a pain in the ass. car. This is a pain in the ass. >> Uh and like you can email someone. You >> Uh and like you can email someone. You >> Uh and like you can email someone. You got to email probably 50 people and you got to email probably 50 people and you got to email probably 50 people and you could like actually shadow them for I could like actually shadow them for I could like actually shadow them for I mean most decisions are reversible and mean most decisions are reversible and mean most decisions are reversible and there are ways to like reduce risk. there are ways to like reduce risk. there are ways to like reduce risk. >> No doubt. And like like um when I was an >> No doubt. And like like um when I was an >> No doubt. And like like um when I was an engineer and before I went to Wall engineer and before I went to Wall engineer and before I went to Wall Street, it turns out I had read Peter Street, it turns out I had read Peter Street, it turns out I had read Peter Lince's One Up on Wall Street. I was Lince's One Up on Wall Street. I was Lince's One Up on Wall Street. I was trading stocks in my spare time. So trading stocks in my spare time. So trading stocks in my spare time. So unconsciously I was testing that in this unconsciously I was testing that in this unconsciously I was testing that in this field that I would eventually go field that I would eventually go field that I would eventually go towards. And so yes, like don't quit towards. And so yes, like don't quit towards. And so yes, like don't quit your job tomorrow just cuz you're your job tomorrow just cuz you're your job tomorrow just cuz you're unhappy. Start figuring out that you're unhappy. Start figuring out that you're unhappy. Start figuring out that you're what direction is the right direction to what direction is the right direction to what direction is the right direction to move towards. some of the people that move towards. some of the people that move towards. some of the people that you you talk about like for example in you you talk about like for example in you you talk about like for example in the book you talk about Robert Zimmerman the book you talk about Robert Zimmerman the book you talk about Robert Zimmerman aka Bob Dylan and you're like he um f aka Bob Dylan and you're like he um f aka Bob Dylan and you're like he um f found his fascination and he like found his fascination and he like found his fascination and he like followed it like pretty ruthlessly and followed it like pretty ruthlessly and followed it like pretty ruthlessly and and and became Bob Dylan and but then and and became Bob Dylan and but then and and became Bob Dylan and but then you also are like he's also like you you also are like he's also like you you also are like he's also like you barely mentioned this but you're like barely mentioned this but you're like barely mentioned this but you're like he's notoriously prickly like he's hard he's notoriously prickly like he's hard he's notoriously prickly like he's hard to like get close to but then like I to like get close to but then like I to like get close to but then like I know you've worked with Travis Kick know you've worked with Travis Kick know you've worked with Travis Kick who's like um a pretty wild guy the who's like um a pretty wild guy the who's like um a pretty wild guy the people who in order to like do these people who in order to like do these people who in order to like do these exercises of finding your passion And do exercises of finding your passion And do exercises of finding your passion And do you sort of have to be like a ruthless you sort of have to be like a ruthless you sort of have to be like a ruthless [ __ ] you think? [ __ ] you think? [ __ ] you think? >> I don't think so. I mean, Danny's one of >> I don't think so. I mean, Danny's one of >> I don't think so. I mean, Danny's one of the nicest humans I've ever met in my the nicest humans I've ever met in my the nicest humans I've ever met in my entire life. Um even though um someone entire life. Um even though um someone entire life. Um even though um someone like Bobby Knight, who we have in the like Bobby Knight, who we have in the like Bobby Knight, who we have in the book, is known as being that way. He's book, is known as being that way. He's book, is known as being that way. He's probably got the biggest coaching tree probably got the biggest coaching tree probably got the biggest coaching tree in the history of the sport, which means in the history of the sport, which means in the history of the sport, which means people have developed underneath him and people have developed underneath him and people have developed underneath him and both as coaches and players and become both as coaches and players and become both as coaches and players and become coaches. So even if you know this coaches. So even if you know this coaches. So even if you know this prickly guy you see throwing the chair prickly guy you see throwing the chair prickly guy you see throwing the chair is is not the one that developed all is is not the one that developed all is is not the one that developed all these humans you know and put them on these humans you know and put them on these humans you know and put them on their way and on their path. And one of their way and on their path. And one of their way and on their path. And one of the things I love about a lot of the the things I love about a lot of the the things I love about a lot of the stories in the in the book is that these stories in the in the book is that these stories in the in the book is that these people reach a place where they're people reach a place where they're people reach a place where they're touching so many people in their field. touching so many people in their field. touching so many people in their field. I think that's a more fulfilling test of I think that's a more fulfilling test of I think that's a more fulfilling test of were you successful than did you hit were you successful than did you hit were you successful than did you hit some milestone. some milestone. some milestone. >> Yeah. But it's a lot easier to do a >> Yeah. But it's a lot easier to do a >> Yeah. But it's a lot easier to do a bunch of stuff like following your bunch of stuff like following your bunch of stuff like following your passion when you have hit milestones. passion when you have hit milestones. passion when you have hit milestones. Like sometimes when people people say Like sometimes when people people say Like sometimes when people people say follow your passion. follow your passion. follow your passion. What I really want to tell people I'm What I really want to tell people I'm What I really want to tell people I'm like basically this sounds like crude like basically this sounds like crude like basically this sounds like crude but I'm like if you can get rich fast do but I'm like if you can get rich fast do but I'm like if you can get rich fast do that. that. that. >> Some people get in a position where they >> Some people get in a position where they >> Some people get in a position where they spend right up to what they earn and spend right up to what they earn and spend right up to what they earn and then they don't have they don't have then they don't have they don't have then they don't have they don't have flexibility. And so you move from one flexibility. And so you move from one flexibility. And so you move from one town to another. Um, a lot of the people town to another. Um, a lot of the people town to another. Um, a lot of the people in the book do that and if you're stuck, in the book do that and if you're stuck, in the book do that and if you're stuck, you're stuck. You know, you might be you're stuck. You know, you might be you're stuck. You know, you might be have to stay in a job because you've have to stay in a job because you've have to stay in a job because you've built a expense burden. It goes right up built a expense burden. It goes right up built a expense burden. It goes right up against the top of it. I saw a ton of against the top of it. I saw a ton of against the top of it. I saw a ton of those people when I came to New York. those people when I came to New York. those people when I came to New York. >> What did you see? >> What did you see? >> What did you see? >> I mean, we were getting paid decent >> I mean, we were getting paid decent >> I mean, we were getting paid decent money like for money like for money like for >> This was when you're a researcher. >> This was when you're a researcher. >> This was when you're a researcher. >> Yeah. Yeah. For entry- level jobs. But >> Yeah. Yeah. For entry- level jobs. But >> Yeah. Yeah. For entry- level jobs. But they would run and get they'd go get the they would run and get they'd go get the they would run and get they'd go get the place in the Hamptons and they'd join place in the Hamptons and they'd join place in the Hamptons and they'd join the private club and they'd run their the private club and they'd run their the private club and they'd run their budget right up to the top sometimes budget right up to the top sometimes budget right up to the top sometimes above it where if they don't get the above it where if they don't get the above it where if they don't get the bonus they're underwater. bonus they're underwater. bonus they're underwater. >> I know people that make seven figures a >> I know people that make seven figures a >> I know people that make seven figures a year, $1 million a year and will year, $1 million a year and will year, $1 million a year and will literally have $0 in savings. literally have $0 in savings. literally have $0 in savings. >> I understand >> I understand >> I understand >> when I early on uh I used to use this >> when I early on uh I used to use this >> when I early on uh I used to use this app called my weekly budget and I app called my weekly budget and I app called my weekly budget and I created a a budget and uh I had a created a a budget and uh I had a created a a budget and uh I had a spreadsheet that would track how much spreadsheet that would track how much spreadsheet that would track how much cash I had saved. So 10,000 to 20,000. cash I had saved. So 10,000 to 20,000. cash I had saved. So 10,000 to 20,000. It was like this is how long you could It was like this is how long you could It was like this is how long you could live without any income. So they the live without any income. So they the live without any income. So they the name of the game was to squirre away as name of the game was to squirre away as name of the game was to squirre away as much cash while keeping expenses low. much cash while keeping expenses low. much cash while keeping expenses low. And it was like anything above 6 months And it was like anything above 6 months And it was like anything above 6 months that's like your FU number. Meaning you that's like your FU number. Meaning you that's like your FU number. Meaning you could like go and like try and could like go and like try and could like go and like try and experiment. experiment. experiment. >> Yeah. It gives you flexibility. >> Yeah. It gives you flexibility. >> Yeah. It gives you flexibility. >> Yeah. And it was like but it was like >> Yeah. And it was like but it was like >> Yeah. And it was like but it was like ruthlessly disciplined to make that ruthlessly disciplined to make that ruthlessly disciplined to make that number bigger even though I didn't make number bigger even though I didn't make number bigger even though I didn't make a lot of money but I was like living a lot of money but I was like living a lot of money but I was like living very frugally and I don't think people very frugally and I don't think people very frugally and I don't think people understand that. And like things like understand that. And like things like understand that. And like things like college debt, which I'm very privileged college debt, which I'm very privileged college debt, which I'm very privileged I didn't have, completely ruins it. And I didn't have, completely ruins it. And I didn't have, completely ruins it. And so like there's a bunch of these like so like there's a bunch of these like so like there's a bunch of these like irreversible decisions that can really irreversible decisions that can really irreversible decisions that can really screw you up when it comes to like being screw you up when it comes to like being screw you up when it comes to like being able to like chase down some of these able to like chase down some of these able to like chase down some of these things. You know, things. You know, things. You know, >> I agree with that. >> I agree with that. >> I agree with that. >> Last night was special because I sat >> Last night was special because I sat >> Last night was special because I sat across from Jim Kramer across from Jim Kramer across from Jim Kramer >> and then next to him was Henry Bligget >> and then next to him was Henry Bligget >> and then next to him was Henry Bligget who founded Business Insider. Just a lot who founded Business Insider. Just a lot who founded Business Insider. Just a lot of like crazy people. When you knew of like crazy people. When you knew of like crazy people. When you knew these guys when they were younger, was these guys when they were younger, was these guys when they were younger, was it clear that you guys were all going to it clear that you guys were all going to it clear that you guys were all going to uh succeed or have you been surprised uh succeed or have you been surprised uh succeed or have you been surprised that someone has been as successful as that someone has been as successful as that someone has been as successful as they are? Well, I think it I think it they are? Well, I think it I think it they are? Well, I think it I think it goes back to our discussion on peer goes back to our discussion on peer goes back to our discussion on peer groups, like like connecting with I've groups, like like connecting with I've groups, like like connecting with I've just always found. Um, and and I think I just always found. Um, and and I think I just always found. Um, and and I think I got more attuned to this the older I got more attuned to this the older I got more attuned to this the older I got. Like have have a big tent got. Like have have a big tent got. Like have have a big tent mentality. Like have have as many mentality. Like have have as many mentality. Like have have as many friends as you can. Try not to judge friends as you can. Try not to judge friends as you can. Try not to judge people too much. Root for people to be people too much. Root for people to be people too much. Root for people to be successful when you can. And and it'll successful when you can. And and it'll successful when you can. And and it'll come back to you in spades, you know. come back to you in spades, you know. come back to you in spades, you know. And I guess I've never been surprised And I guess I've never been surprised And I guess I've never been surprised that the people that end up, you know, that the people that end up, you know, that the people that end up, you know, in s in in Silicon Valley in the middle in s in in Silicon Valley in the middle in s in in Silicon Valley in the middle of it all continue to move forward just of it all continue to move forward just of it all continue to move forward just because it attracts so many ambitious because it attracts so many ambitious because it attracts so many ambitious people, you know, and so I know I I I people, you know, and so I know I I I people, you know, and so I know I I I haven't I haven't been radically haven't I haven't been radically haven't I haven't been radically surprised by anybody's staying power. surprised by anybody's staying power. surprised by anybody's staying power. Keep in mind, I'm 59 years old, so I Keep in mind, I'm 59 years old, so I Keep in mind, I'm 59 years old, so I have the benefit of time to build that have the benefit of time to build that have the benefit of time to build that network. I had 25 years as a venture network. I had 25 years as a venture network. I had 25 years as a venture capitalist. capitalist. capitalist. >> But I think you were on the board of uh >> But I think you were on the board of uh >> But I think you were on the board of uh >> what's the one with you and Danny Meyer? >> what's the one with you and Danny Meyer? >> what's the one with you and Danny Meyer? You're on the board together. You're on the board together. You're on the board together. >> Open table. >> Open table. >> Open table. >> That was like 20 years ago. I mean it >> That was like 20 years ago. I mean it >> That was like 20 years ago. I mean it seems like you you kind of like hit seems like you you kind of like hit seems like you you kind of like hit right pretty early in into right. right pretty early in into right. right pretty early in into right. >> That's kind of key in venture. >> That's kind of key in venture. >> That's kind of key in venture. >> What do you mean? >> What do you mean? >> What do you mean? >> Oh just to be in front of the the the >> Oh just to be in front of the the the >> Oh just to be in front of the the the wave or whatever rolls out like you wave or whatever rolls out like you wave or whatever rolls out like you can't can't be late can't can't be late can't can't be late >> with AI going on right now. Is this does >> with AI going on right now. Is this does >> with AI going on right now. Is this does this remind you of a different period in this remind you of a different period in this remind you of a different period in venture? I've never seen it quite like venture? I've never seen it quite like venture? I've never seen it quite like this. this. this. >> Really? >> Really? >> Really? >> Really? I One thing I think throughout >> Really? I One thing I think throughout >> Really? I One thing I think throughout my career, venture's only gotten more my career, venture's only gotten more my career, venture's only gotten more competitive and now today it's, you competitive and now today it's, you competitive and now today it's, you know, as I've I'm hanging up my boots know, as I've I'm hanging up my boots know, as I've I'm hanging up my boots and watching the next generation, it's and watching the next generation, it's and watching the next generation, it's even more competitive. And the um the even more competitive. And the um the even more competitive. And the um the burn rates that the VCs are comfortable burn rates that the VCs are comfortable burn rates that the VCs are comfortable experimenting with are bigger and bigger experimenting with are bigger and bigger experimenting with are bigger and bigger than ever. Like I thought our 2 billion than ever. Like I thought our 2 billion than ever. Like I thought our 2 billion a year burn rate at Uber was pretty a year burn rate at Uber was pretty a year burn rate at Uber was pretty frightening. Open AI is burning way more frightening. Open AI is burning way more frightening. Open AI is burning way more than that. than that. than that. >> How much are they burning? >> How much are they burning? >> How much are they burning? >> I I don't I've seen different numbers. I >> I I don't I've seen different numbers. I >> I I don't I've seen different numbers. I don't have access to their financials, don't have access to their financials, don't have access to their financials, but like but like but like >> Uber was losing two billion a year. >> Uber was losing two billion a year. >> Uber was losing two billion a year. >> Yeah, but OpenAI is at like eight or 10. >> Yeah, but OpenAI is at like eight or 10. >> Yeah, but OpenAI is at like eight or 10. >> What did uh what does it make you feel >> What did uh what does it make you feel >> What did uh what does it make you feel when your company's losing $2 billion a when your company's losing $2 billion a when your company's losing $2 billion a year? year? year? >> Scared shitless. >> Scared shitless. >> Scared shitless. >> Really? >> Really? >> Really? >> Yeah. Oh, yeah. >> Yeah. Oh, yeah. >> Yeah. Oh, yeah. >> How did you map that out? Like how do >> How did you map that out? Like how do >> How did you map that out? Like how do you go to bed at night knowing that like you go to bed at night knowing that like you go to bed at night knowing that like are you like what do you tell yourself? are you like what do you tell yourself? are you like what do you tell yourself? You're like, "Well, You're like, "Well, You're like, "Well, >> why didn't I sleep much?" There was a >> why didn't I sleep much?" There was a >> why didn't I sleep much?" There was a piece of it that was that that I think piece of it that was that that I think piece of it that was that that I think is as the venture industry gets more is as the venture industry gets more is as the venture industry gets more industrialized was a problem which was I industrialized was a problem which was I industrialized was a problem which was I think the Lyft investors knew that they think the Lyft investors knew that they think the Lyft investors knew that they had to keep funding liquidity and for had to keep funding liquidity and for had to keep funding liquidity and for all bunch of reasons that relate to all bunch of reasons that relate to all bunch of reasons that relate to network effects. It was always supposed network effects. It was always supposed network effects. It was always supposed to be kind of a single marketplace that to be kind of a single marketplace that to be kind of a single marketplace that would win and but you if you don't have would win and but you if you don't have would win and but you if you don't have the constraint of financial viability, the constraint of financial viability, the constraint of financial viability, you can lose money to create to the you can lose money to create to the you can lose money to create to the perception of liquidity. You can pay perception of liquidity. You can pay perception of liquidity. You can pay drivers to be present when they wouldn't drivers to be present when they wouldn't drivers to be present when they wouldn't naturally be that. naturally be that. naturally be that. >> Yeah. I used to joke my last company in >> Yeah. I used to joke my last company in >> Yeah. I used to joke my last company in San Francisco, we didn't take venture San Francisco, we didn't take venture San Francisco, we didn't take venture capital, but we used to say we were capital, but we used to say we were capital, but we used to say we were still VC funded because uh Uber and all still VC funded because uh Uber and all still VC funded because uh Uber and all these companies would give like the these companies would give like the these companies would give like the craziest referrals. So like I remember craziest referrals. So like I remember craziest referrals. So like I remember like giving my referral to everyone like like giving my referral to everyone like like giving my referral to everyone like oh I drive on Uber for or I ride on Uber oh I drive on Uber for or I ride on Uber oh I drive on Uber for or I ride on Uber for free. for free. for free. >> I get it. And and and and it wasn't >> I get it. And and and and it wasn't >> I get it. And and and and it wasn't until Lyft went public first, which is until Lyft went public first, which is until Lyft went public first, which is probably the best thing that could have probably the best thing that could have probably the best thing that could have ever happened to Uber where Wall Street ever happened to Uber where Wall Street ever happened to Uber where Wall Street held them accountable for being held them accountable for being held them accountable for being profitable. And and it's it's at that profitable. And and it's it's at that profitable. And and it's it's at that point when things really tipped and and point when things really tipped and and point when things really tipped and and where Uber was able to then take where Uber was able to then take where Uber was able to then take advantage of the network effect and advantage of the network effect and advantage of the network effect and being larger and and now spits off well being larger and and now spits off well being larger and and now spits off well north of 10 billion a year in free cash north of 10 billion a year in free cash north of 10 billion a year in free cash flow. flow. flow. >> That's how big it is now. That's insane. >> That's how big it is now. That's insane. >> That's how big it is now. That's insane. Did you did that is that bigger than Did you did that is that bigger than Did you did that is that bigger than your prediction? your prediction? your prediction? >> Oh, and I made a prediction about the >> Oh, and I made a prediction about the >> Oh, and I made a prediction about the the uh market cap. It had a bunch of the uh market cap. It had a bunch of the uh market cap. It had a bunch of ranges. I I don't have it in front of ranges. I I don't have it in front of ranges. I I don't have it in front of me, but DAR got it to 200 billion market me, but DAR got it to 200 billion market me, but DAR got it to 200 billion market cap. And I don't know if that was in I I cap. And I don't know if that was in I I cap. And I don't know if that was in I I assume you're referring to the blog post assume you're referring to the blog post assume you're referring to the blog post I wrote. I wrote. I wrote. >> No, I haven't. >> No, I haven't. >> No, I haven't. >> Oh, okay. Yeah. >> Oh, okay. Yeah. >> Oh, okay. Yeah. >> What did you say? Or what was the >> What did you say? Or what was the >> What did you say? Or what was the >> There was a professor at NYU that wrote >> There was a professor at NYU that wrote >> There was a professor at NYU that wrote a blog post that said it would only be a blog post that said it would only be a blog post that said it would only be worth 4 billion and I pushed back. worth 4 billion and I pushed back. worth 4 billion and I pushed back. >> I remember that. We did talk about that. >> I remember that. We did talk about that. >> I remember that. We did talk about that. >> Yeah. Yeah. >> Yeah. Yeah. >> Yeah. Yeah. >> Do did you see the blog post the other >> Do did you see the blog post the other >> Do did you see the blog post the other day about on Substack where they're like day about on Substack where they're like day about on Substack where they're like AI is going to make uh the economy AI is going to make uh the economy AI is going to make uh the economy worse? worse? worse? >> Do you see how one blog post like >> Do you see how one blog post like >> Do you see how one blog post like brought down? brought down? brought down? >> It's pretty amazing. That's crazy, >> It's pretty amazing. That's crazy, >> It's pretty amazing. That's crazy, right? right? right? >> Yes. >> Yes. >> Yes. >> Did your blog ever do that? >> Did your blog ever do that? >> Did your blog ever do that? >> Not not of that scale. No. >> Not not of that scale. No. >> Not not of that scale. No. >> Yeah, that was that was insane. >> Yeah, that was that was insane. >> Yeah, that was that was insane. >> Insane. There's a lot of fear out there. >> Insane. There's a lot of fear out there. >> Insane. There's a lot of fear out there. Just remember uh Warren Buffett said be Just remember uh Warren Buffett said be Just remember uh Warren Buffett said be be greedy when others are fearful and be greedy when others are fearful and be greedy when others are fearful and fearful when others are greedy. So the fearful when others are greedy. So the fearful when others are greedy. So the first wave of AI was a lot of people first wave of AI was a lot of people first wave of AI was a lot of people being greedy. And now all of a sudden being greedy. And now all of a sudden being greedy. And now all of a sudden there's fear for the first time. So if there's fear for the first time. So if there's fear for the first time. So if you're a net buyer of stocks, this is you're a net buyer of stocks, this is you're a net buyer of stocks, this is when you this when you sharpen your when you this when you sharpen your when you this when you sharpen your pencil. you see all these interesting pencil. you see all these interesting pencil. you see all these interesting founders other than like I mean I don't founders other than like I mean I don't founders other than like I mean I don't want to hear like Travis or like some of want to hear like Travis or like some of want to hear like Travis or like some of the bigname ones who kind of have stuck the bigname ones who kind of have stuck the bigname ones who kind of have stuck out as like being like particularly out as like being like particularly out as like being like particularly sticky and uh formidable. sticky and uh formidable. sticky and uh formidable. >> Well, one of the most impressive people >> Well, one of the most impressive people >> Well, one of the most impressive people I know is a guy named Rich Barton. He I know is a guy named Rich Barton. He I know is a guy named Rich Barton. He founded Expedia and then Zillow. Expedia founded Expedia and then Zillow. Expedia founded Expedia and then Zillow. Expedia was acquired by Diller, so he knows was acquired by Diller, so he knows was acquired by Diller, so he knows Barry and all that, but but Rich has Barry and all that, but but Rich has Barry and all that, but but Rich has this remarkable ability to be top 1 this remarkable ability to be top 1 this remarkable ability to be top 1 percentile as a product technology percentile as a product technology percentile as a product technology disruptor, but also as a leader, that disruptor, but also as a leader, that disruptor, but also as a leader, that thing we were talking about before. And thing we were talking about before. And thing we were talking about before. And I I usually see people tilt one degree I I usually see people tilt one degree I I usually see people tilt one degree or the other and not both. And he's this or the other and not both. And he's this or the other and not both. And he's this rare person that that does it on both. rare person that that does it on both. rare person that that does it on both. Um, and so I frequently lean on him for Um, and so I frequently lean on him for Um, and so I frequently lean on him for advice. Do advice. Do advice. Do >> you have an example of like a story of >> you have an example of like a story of >> you have an example of like a story of like where good leadership changed like where good leadership changed like where good leadership changed >> getting companies to pivot fast when >> getting companies to pivot fast when >> getting companies to pivot fast when they need to? I mean, right now with AI, they need to? I mean, right now with AI, they need to? I mean, right now with AI, any companies out there, you mentioned any companies out there, you mentioned any companies out there, you mentioned what happened with this report like that what happened with this report like that what happened with this report like that that Door Dash is down 5% because the that Door Dash is down 5% because the that Door Dash is down 5% because the report said you could build Door Dash report said you could build Door Dash report said you could build Door Dash for free, which I don't believe, but you for free, which I don't believe, but you for free, which I don't believe, but you know, whatever. know, whatever. know, whatever. >> Yeah. And that report, by the way, for >> Yeah. And that report, by the way, for >> Yeah. And that report, by the way, for the listener, it was basically like what the listener, it was basically like what the listener, it was basically like what happens in the world if AI is so happens in the world if AI is so happens in the world if AI is so efficient that we don't have jobs. And efficient that we don't have jobs. And efficient that we don't have jobs. And if we don't have jobs and we're not if we don't have jobs and we're not if we don't have jobs and we're not buying stuff and it was just like a buying stuff and it was just like a buying stuff and it was just like a story. It was it was an idea. story. It was it was an idea. story. It was it was an idea. >> But how do you get So the the thing that >> But how do you get So the the thing that >> But how do you get So the the thing that I was going to mention is just how do I was going to mention is just how do I was going to mention is just how do you make sure your company is properly you make sure your company is properly you make sure your company is properly aware of this new wave? And how do you aware of this new wave? And how do you aware of this new wave? And how do you get everyone super excited about get everyone super excited about get everyone super excited about figuring out what it's going to mean for figuring out what it's going to mean for figuring out what it's going to mean for your company? And that that's not easy your company? And that that's not easy your company? And that that's not easy to do. And I, you know, I'm back on the to do. And I, you know, I'm back on the to do. And I, you know, I'm back on the board of Zillow, so I watched him do board of Zillow, so I watched him do board of Zillow, so I watched him do that recently. And it requires having that recently. And it requires having that recently. And it requires having both the conviction to make that kind of both the conviction to make that kind of both the conviction to make that kind of pivot and move and then the ability to pivot and move and then the ability to pivot and move and then the ability to get the people to follow you. get the people to follow you. get the people to follow you. >> That's funny that you said it was like >> That's funny that you said it was like >> That's funny that you said it was like being good at product and being a good being good at product and being a good being good at product and being a good leader. I think you also said, leader. I think you also said, leader. I think you also said, >> do you also say that like Jeff Bezos is >> do you also say that like Jeff Bezos is >> do you also say that like Jeff Bezos is one of those guys who does two things one of those guys who does two things one of those guys who does two things really well? It would be a good exercise really well? It would be a good exercise really well? It would be a good exercise to for someone to kind of write down the to for someone to kind of write down the to for someone to kind of write down the leadership techniques of Jeff Bezos leadership techniques of Jeff Bezos leadership techniques of Jeff Bezos because Amazon remained innovative after because Amazon remained innovative after because Amazon remained innovative after it got to like a 100,000 employees. And it got to like a 100,000 employees. And it got to like a 100,000 employees. And that's very hard to do. It's not one that's very hard to do. It's not one that's very hard to do. It's not one human. It's one human creating a system human. It's one human creating a system human. It's one human creating a system that reinforces whatever he thought. You that reinforces whatever he thought. You that reinforces whatever he thought. You see what I'm saying? And like how do you see what I'm saying? And like how do you see what I'm saying? And like how do you make that system keep doing that even make that system keep doing that even make that system keep doing that even after, you know, on days you're not after, you know, on days you're not after, you know, on days you're not there? and him and Elon, I just don't there? and him and Elon, I just don't there? and him and Elon, I just don't think people fully gro how they're able think people fully gro how they're able think people fully gro how they're able to lead. to lead. to lead. >> A lot of these people who are these like >> A lot of these people who are these like >> A lot of these people who are these like kind of the titans of industry that you kind of the titans of industry that you kind of the titans of industry that you know, do you think that there's any know, do you think that there's any know, do you think that there's any correlation or reverse correlation uh of correlation or reverse correlation uh of correlation or reverse correlation uh of uh happiness? uh happiness? uh happiness? >> I don't know anyone that laughs louder >> I don't know anyone that laughs louder >> I don't know anyone that laughs louder than Jeff Bezos. If you've been around than Jeff Bezos. If you've been around than Jeff Bezos. If you've been around him when he lets go one of his his kas, him when he lets go one of his his kas, him when he lets go one of his his kas, man, I and I and I think he really loves man, I and I and I think he really loves man, I and I and I think he really loves life. Um life. Um life. Um I'm just saying there I don't think I'm just saying there I don't think I'm just saying there I don't think there's a correlation. I mean I I every there's a correlation. I mean I I every there's a correlation. I mean I I every chance I get if Toby from Shopify does a chance I get if Toby from Shopify does a chance I get if Toby from Shopify does a podcast or something, I'm eating it up. podcast or something, I'm eating it up. podcast or something, I'm eating it up. And I find his attitude on leadership in And I find his attitude on leadership in And I find his attitude on leadership in life to be lighthearted. You know, life to be lighthearted. You know, life to be lighthearted. You know, >> he seems like another one of these >> he seems like another one of these >> he seems like another one of these product leadership guys. He's a very product leadership guys. He's a very product leadership guys. He's a very unique flavor of leadership. He has a unique flavor of leadership. He has a unique flavor of leadership. He has a very wise very wise very wise >> something, right? >> something, right? >> something, right? >> Yeah. There's something wise about him. >> Yeah. There's something wise about him. >> Yeah. There's something wise about him. Do you see where he took screenshots of Do you see where he took screenshots of Do you see where he took screenshots of his computer screen every 10 minutes for his computer screen every 10 minutes for his computer screen every 10 minutes for the last 20 years? And uh because he was the last 20 years? And uh because he was the last 20 years? And uh because he was just he's like I'm a nerd and I just just he's like I'm a nerd and I just just he's like I'm a nerd and I just love like having this diary of like what love like having this diary of like what love like having this diary of like what what was on my like he was tracking all what was on my like he was tracking all what was on my like he was tracking all of this. And uh he's like I didn't know of this. And uh he's like I didn't know of this. And uh he's like I didn't know what I was going to do with this. Now what I was going to do with this. Now what I was going to do with this. Now that AI exists, I can like upload this that AI exists, I can like upload this that AI exists, I can like upload this and like it could like teach me about and like it could like teach me about and like it could like teach me about myself. But he's got this like really myself. But he's got this like really myself. But he's got this like really cool I call it like nerd wisdom like um cool I call it like nerd wisdom like um cool I call it like nerd wisdom like um you know Darm at HubSpot. you know Darm at HubSpot. you know Darm at HubSpot. >> I have men but I don't know him as well. >> I have men but I don't know him as well. >> I have men but I don't know him as well. It's kind of the same thing where It's kind of the same thing where It's kind of the same thing where there's like there's these groups of there's like there's these groups of there's like there's these groups of group of guys who are like very like group of guys who are like very like group of guys who are like very like when you think of a leader sometimes you when you think of a leader sometimes you when you think of a leader sometimes you think of like a Napoleon like rah rah think of like a Napoleon like rah rah think of like a Napoleon like rah rah like rile people up but there's this like rile people up but there's this like rile people up but there's this other group of like fairly introverted other group of like fairly introverted other group of like fairly introverted people and they're quiet and when they people and they're quiet and when they people and they're quiet and when they talk you listen but I think they're talk you listen but I think they're talk you listen but I think they're they're both useful um for someone who's they're both useful um for someone who's they're both useful um for someone who's like 18 19 20 they're listening to this like 18 19 20 they're listening to this like 18 19 20 they're listening to this you did all this research for this book you did all this research for this book you did all this research for this book are there what biographies do you are there what biographies do you are there what biographies do you suggest they go read suggest they go read suggest they go read >> I mean I think it would be heavily >> I mean I think it would be heavily >> I mean I think it would be heavily dependent on what interests them dependent on what interests them dependent on what interests them >> or rather what made the biggest impact >> or rather what made the biggest impact >> or rather what made the biggest impact on I don't know if I was reading on I don't know if I was reading on I don't know if I was reading biographies at 17. I really got into biographies at 17. I really got into biographies at 17. I really got into reading when I got to business school. reading when I got to business school. reading when I got to business school. And I they're all listed in here. And I they're all listed in here. And I they're all listed in here. There's 35 books listed at the back of There's 35 books listed at the back of There's 35 books listed at the back of the book. So I But it I think the key is the book. So I But it I think the key is the book. So I But it I think the key is just to and I don't even know that it just to and I don't even know that it just to and I don't even know that it has to be reading. There's there's so has to be reading. There's there's so has to be reading. There's there's so many podcasts like the ones you do and many podcasts like the ones you do and many podcasts like the ones you do and and YouTube interviews with people. Like and YouTube interviews with people. Like and YouTube interviews with people. Like it's so easy to go learn about it's so easy to go learn about it's so easy to go learn about something. So, I'm just like whatever it something. So, I'm just like whatever it something. So, I'm just like whatever it is interest you, go learn more about it is interest you, go learn more about it is interest you, go learn more about it and see if that takes you somewhere. See and see if that takes you somewhere. See and see if that takes you somewhere. See if that makes you excited. See if it if that makes you excited. See if it if that makes you excited. See if it makes you want to pick up the next one. makes you want to pick up the next one. makes you want to pick up the next one. And if it is, I think you're probably in And if it is, I think you're probably in And if it is, I think you're probably in the right lane. If not, just pay the right lane. If not, just pay the right lane. If not, just pay attention to what fascinates you. You attention to what fascinates you. You attention to what fascinates you. You know, pay attention to what interests know, pay attention to what interests know, pay attention to what interests you. I'm uh a big believer that more you. I'm uh a big believer that more you. I'm uh a big believer that more people can chase careers in their hobby people can chase careers in their hobby people can chase careers in their hobby than someone else might say. like like than someone else might say. like like than someone else might say. like like if if if there's something you're just if if if there's something you're just if if if there's something you're just super passionate about, even if it's a super passionate about, even if it's a super passionate about, even if it's a hobby, you might be surprised. There hobby, you might be surprised. There hobby, you might be surprised. There might be there might be a way to make a might be there might be a way to make a might be there might be a way to make a career around it. career around it. career around it. >> Well, it's a lot easier now with the >> Well, it's a lot easier now with the >> Well, it's a lot easier now with the internet. internet. internet. >> It's this is But by the way, I would >> It's this is But by the way, I would >> It's this is But by the way, I would love to close with this point that you love to close with this point that you love to close with this point that you just made. Um, if you're a what, like I just made. Um, if you're a what, like I just made. Um, if you're a what, like I said, if you're someone who's disengaged said, if you're someone who's disengaged said, if you're someone who's disengaged at work that went through some process at work that went through some process at work that went through some process you didn't care about that much, I can you didn't care about that much, I can you didn't care about that much, I can understand why this AI thing would feel understand why this AI thing would feel understand why this AI thing would feel threatening to you. If you're crafting threatening to you. If you're crafting threatening to you. If you're crafting your own personal career and you're high your own personal career and you're high your own personal career and you're high agency, I think that's a word you used agency, I think that's a word you used agency, I think that's a word you used earlier. AI is like a jetpack. Like you earlier. AI is like a jetpack. Like you earlier. AI is like a jetpack. Like you can do more stuff than you ever could can do more stuff than you ever could can do more stuff than you ever could before. You can learn faster than you before. You can learn faster than you before. You can learn faster than you ever could before in the history of ever could before in the history of ever could before in the history of time. You can find people to connect time. You can find people to connect time. You can find people to connect with. You can network faster than than with. You can network faster than than with. You can network faster than than you ever could before. And so if you you ever could before. And so if you you ever could before. And so if you have agency and and a direction you're have agency and and a direction you're have agency and and a direction you're headed in, AI is going to make things headed in, AI is going to make things headed in, AI is going to make things way better. So, I think it's just this way better. So, I think it's just this way better. So, I think it's just this interesting paradox that there are interesting paradox that there are interesting paradox that there are people out there who fear that it's people out there who fear that it's people out there who fear that it's going to dismantle them and there's going to dismantle them and there's going to dismantle them and there's people out there who are like, "Oh my people out there who are like, "Oh my people out there who are like, "Oh my god, I can't I've met so many what I god, I can't I've met so many what I god, I can't I've met so many what I would call like SMB founders or regional would call like SMB founders or regional would call like SMB founders or regional founders running, you know, businesses founders running, you know, businesses founders running, you know, businesses that are mats or storage facilities and that are mats or storage facilities and that are mats or storage facilities and and they've discovered all the things and they've discovered all the things and they've discovered all the things they can do with AI and now they they they can do with AI and now they they they can do with AI and now they they feel super human. feel super human. feel super human. >> So, I I'll I'll wrap up with the story. >> So, I I'll I'll wrap up with the story. >> So, I I'll I'll wrap up with the story. You you'll dig this. So, my You you'll dig this. So, my You you'll dig this. So, my mother-in-law, her name's Smithy, she mother-in-law, her name's Smithy, she mother-in-law, her name's Smithy, she came here uh to to America from Haiti at came here uh to to America from Haiti at came here uh to to America from Haiti at like 14 years old, didn't speak English, like 14 years old, didn't speak English, like 14 years old, didn't speak English, um married my father-in-law, Jeff. Jeff um married my father-in-law, Jeff. Jeff um married my father-in-law, Jeff. Jeff owned a moving company. Smithy was a owned a moving company. Smithy was a owned a moving company. Smithy was a stay-at-home mom for a long time. The stay-at-home mom for a long time. The stay-at-home mom for a long time. The kids grew up, and she was like, "I'm kids grew up, and she was like, "I'm kids grew up, and she was like, "I'm kind of lost. I need to do something. kind of lost. I need to do something. kind of lost. I need to do something. What's going on?" So, about 5 years ago, What's going on?" So, about 5 years ago, What's going on?" So, about 5 years ago, she says to me, she goes, "Sam, I think she says to me, she goes, "Sam, I think she says to me, she goes, "Sam, I think I'm going to start an online store that I'm going to start an online store that I'm going to start an online store that sells pillows." Like, pillows or sells pillows." Like, pillows or sells pillows." Like, pillows or whatever sounds good. And I like I was whatever sounds good. And I like I was whatever sounds good. And I like I was like, "There's a thing called Shopify. like, "There's a thing called Shopify. like, "There's a thing called Shopify. Just start just start there." It's been Just start just start there." It's been Just start just start there." It's been 5 years since that. She now has a pillow 5 years since that. She now has a pillow 5 years since that. She now has a pillow company that sells over a million company that sells over a million company that sells over a million dollars a year in pillows. She has a dollars a year in pillows. She has a dollars a year in pillows. She has a warehouse in New Jersey with five warehouse in New Jersey with five warehouse in New Jersey with five full-time employees selling pillows. She full-time employees selling pillows. She full-time employees selling pillows. She was just on the pod. And she uses AI was just on the pod. And she uses AI was just on the pod. And she uses AI like all day to like she's like, "How do like all day to like she's like, "How do like all day to like she's like, "How do I buy an ad?" And like, you know, chat I buy an ad?" And like, you know, chat I buy an ad?" And like, you know, chat GBT like teaches her or she's like, "Uh, GBT like teaches her or she's like, "Uh, GBT like teaches her or she's like, "Uh, how do I whatever?" Like it's YouTube how do I whatever?" Like it's YouTube how do I whatever?" Like it's YouTube and chat GBT like telling her what to and chat GBT like telling her what to and chat GBT like telling her what to do. And she didn't know. She didn't know do. And she didn't know. She didn't know do. And she didn't know. She didn't know the word e-commerce. She didn't know the word e-commerce. She didn't know the word e-commerce. She didn't know what that meant. what that meant. what that meant. >> She basically just knew what Google was >> She basically just knew what Google was >> She basically just knew what Google was and that that was it. And now she in her and that that was it. And now she in her and that that was it. And now she in her late 50s started a e-commerce business late 50s started a e-commerce business late 50s started a e-commerce business that does millions of dollars a year. that does millions of dollars a year. that does millions of dollars a year. >> That's amazing. >> That's amazing. >> That's amazing. >> Crazy, right? >> Crazy, right? >> Crazy, right? >> Yeah. No, but there's never been a >> Yeah. No, but there's never been a >> Yeah. No, but there's never been a better time to propel yourself forward better time to propel yourself forward better time to propel yourself forward if that's if that's what you're prepared if that's if that's what you're prepared if that's if that's what you're prepared to do. to do. to do. >> Well, thank you for doing this, brother. >> Well, thank you for doing this, brother. >> Well, thank you for doing this, brother. All right. All right. God bless. Take All right. All right. God bless. Take All right. All right. God bless. Take care. Yeah.