21: Reinvent Yourself with James Altucher
8 Dec 2025 · 72 min
James Altucher and Jenny Blake discuss why reinvention is continuous, not a one-time event. They cover daily practices like writing ten ideas a day and building community, plus how to recover emotionally from setbacks and think in five-year horizons instead of chasing quick wins.
Questions this episode answers
January 1, 2016.
September 2016 (with Portfolio/Penguin).
5½ years.
More than 20 million readers since 2010 (as stated in the episode).
About 15 million downloads (host’s estimate mentioned in the intro).
Chapters
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Hi, I'm Jenny Blake, your host of the Pivot Podcast and author of the book Turn what's Working for your into what's Next, which comes out with Portfolio Penguin in September of 2016.
In this podcast I talk with peak performers to reverse engineer their most successful career. Pivots interview experts on what it takes to be agile in a rapidly evolving economy and open the kimono on what happens behind the scenes of my book and business. You can learn to capitalize on risk, fear and uncertainty as the doorways of opportunity. My promise is that you will leave every episode with practical tips, tools and tactics. For show notes from this episode, visit JennyBlake Me podcast.
If change is the only constant, then let's get better at it. Here we go.
Happy New Year everybody. Today is a very special day for two reasons. One, it's the start of 2016 and two, I have one of my superheroes, James Altucher. For today's Pivot podcast, one of my I have two words of the year this year, Magic and Serendipity. This is a little bit of magic because when I was a kid I was not into Marvel Comics. I would sit on the floor of the Green Apple bookstore reading books. Authors were my heroes growing up. I wanted to be them. I wanted to be like them. I wanted to know them. And James has been one of those people for me the last few years. I read his book Choose Yourself when I was having one of my most difficult times of my life and it was absolutely instrumental and the book I wish I would have written at that time. And then Serendipity. James and I ran into each other multiple times in the same month here in New York City and now we are recording together. Today we are going to share James Awesome Ultimate Cheat sheet for Reinventing yourself. We're going to give you some reinvention pointers for 2016 and first, a little bit of background about James. He is a successful entrepreneur, angel investor, chess master and prolific writer. One of my favorites. As you know. He is the author of 17 books including the Wall Street Journal bestsellers the Power of Know and choose yourself. He. His website, JamesAltucher.com has attracted more than 20 million readers since its launch in 2010. His three podcasts now ask Altucher, the James Altucher show, and Question of the Day with Stephen Dubner. And these shows have been downloaded at this point, it's probably 15 million times, I would estimate. And I just have to say I love James's writing because it is reverent, smart, funny, and above all, honest. And I feel like James, it's such a service to everyone reading and it is an absolute joy and an honor to have you here on the Pivot podcast.
Jenny, thanks so much for having me on the podcast. And it was so funny because literally everywhere I normally just like sit down, stay in my house and never move. And it seemed like every time I was going to like another location, you were. Oh, you were just outside like reading or at the party or here or there. So I'm glad we finally got together to do this podcast.
Me too.
And congratulations on the launch of this podcast.
Thank you so much. It's such a joy to have you here. And same. I don't really leave the house much. I work from home and yet for a couple weeks there, every time I did there you were. So I promise I'm not stalking you.
Vice versa.
Okay, awesome.
Good.
Glad we established that. So let's get into this reinvention chat. So I this by the way, everyone, this is a poster that we'll link to in the show notes. It's so awesome. The first principle letter a. And there's 51 items. We may not get to all of them today.
Wow. I wrote 51 items. 51 from a. I totally forget to double W. Okay. Yeah, maybe that's why I use letters. So I never know actually the number and I don't know how to count very well. So.
Right.
It's.
I know this is jam packed. So number one, reinvention never stops.
It's so true. Because think about it. I was just talking to someone yesterday and he was asking me, I was on another podcast and he was asking me, what are your goals for the next year? And I look back over the past year and maybe five or six major things happened to me this past year. I could not have predicted a single one of them. So like, new podcast, finishing another podcast, writing two books, starting another business. All sorts of things that have happened in my personal life. Nothing I could have predicted. So I sort of think the whole notion of trying to guide in advance every aspect of your reinvention is Kind of a fool's journey. Like, you can't really predict. All you can do is right now do what you can to make sure that whatever reinvention is in store for you is already happening right now in a good way, inside of you. Because whatever is inside is gonna manifest itself outside. And I don't mean that in this law of attraction sort of way, but it's just true. If you're healthy. Just as a basic example, if you're healthy, you're gonna have a better year than if you're sick in bed the whole year. So, you know, that's. And if you try to be healthy on every level, let's say physically, emotionally, creatively, you know, let's call it spiritually, but I also. You can replace that with gratitude, then you're going to have a better year, no matter what. Even if it's unpredictable, you're going to have a better year than you would have if all those things were not so good for you.
It's true. Because you've said if we don't reinvent, we die. And on some level, I think we know that. But why do you think it is that we also resist reinvention at the same time, even knowing how important it is?
I think people are afraid. They're like, okay, I got a job in a cubicle and it's stable, I better hold onto it and, and do everything I can. Like, even if it's horrible for me, I better hold onto it because otherwise I could be homeless. So people go to the worst case scenario, like, immediately, or at least I do. And I have done. And that's a very scary thought. Even though the whole notion of a stable salary is also not safe. Like, it's, it's like, it's like a Thanksgiving. It's like a turkey going into Thanksgiving. Like, oh my gosh, they're feeding me so great. They're treating me so good. And then the day before Thanksgiving, they, what? What's that knife? You know, they cut off my head. And so that's like the stable salary thing too. But let me ask you, like, you, you were. How long were you at Google?
5 and a half years.
So you worked at Google for five and a half years? The best company in the world for five and a half years. How did you know it was time to change?
Well, first, health. I was hitting points of burnout. I was juggling my side hustle, my blog, and my book. And I realized it wasn't sustainable. That when I asked myself, could I see myself doing, working this same way for the next 25 years. That 30, no way.
So you reach some point where, and this has happened to me too, you reach some point where almost physically, even though you were at the best company in the world, like heck, I want to work at Google right now. Like, I'd be the janitor at Google right now and I'd be happy with it. So, so many people want to, want to have the job you probably had and yet you just felt physically at some point after five and a half years, ugh, I can't get out of bed anymore. What's going to happen? Like, did you have a hard time getting out of bed?
You know, a little the more so. And I think the piece that really did it for me was I felt that during my days there and I did. I had the perfect on paper job. I was thrilled with it. I was doing coaching and career development, global manager training at Google. I was managing authors of Google.
You have to endoogle, right?
I was managing the authors of Google program. These are my heroes, you know. But in my day to day work, I would say I was operating in my zone of genius 20% of the time. And the rest was meetings and PowerPoint decks and things where when I looked, I said I could either impact 30,000 people within Google or I could try and leave and expand that influence. And ultimately my goal is to be as helpful as possible to as many people as possible. And I just kind of decided now or never to go all in on my business.
How did you decide what happened that day?
I realized that I would forever regret not trying. That I was, I was imagining the fear. I was thinking, am I crazy to leave Google? I joke that people say it's like the way they would act when I told them that was like breaking up with Brad Pitt. You really think you can do better than Google? How are you gonna feed yourself? How are you gonna earn such a good living? Also the reputation, my reputation was tied up. It was such a sexy brand.
Yeah. When you were at Google, I'm sure nobody ever not returned your phone calls. And if you're not at Google, people are like, who? Like, where is she from?
I was worried I wouldn't have value if I left. Would my author heroes want to talk to me anymore? Would they care? Because when I was at Google, I could get them in. But then the flip side of that coin was oftentimes when people emailed me, I didn't know if they cared who I was at all or wanted to form a relationship. Maybe they just Wanted to get in and speak at Google. So, yeah, for me, you know, I even say in my book, pivot or get pivoted.
That's a good quote. Yeah.
And maybe it's pivot or be pivoted.
But essentially I like, get though, because, you know, someone else, if you don't take charge of what's happening again, both inside and outside, someone else definitely will. Particularly the more talented you are, the more kind of special you are, the more healthy you are. Other people want that energy. And so they will get to you if you don't deal with yourself first.
Right. And that energy will start to diminish. And then part of one of my favorite quotes, David White, that which you can plan is too small for you to live. And it occurred to me when you said so many of the biggest things that happened to you this year, you could never have predicted many.
Never.
So in some ways, reinvention requires actively knowing we have to reinvent and also being open to the surprise of reinvention.
You have to, because if you try to control anything, you're just gonna end up being disappointed.
Yes.
A great example is if you write a book and you say, I really want this to be on the New York Times bestseller list. Well, you know, hundreds of thousands of books are published and 10 a week or whatever, I don't know what the number is. Get on the New York Times bestseller list. So chances are you're going to fail at your goal and you're going to be sad about it. So don't keep setting yourself up for sadness when actually great things are happening. Oh my God, I did a book and there's so many things that can come from that. I'm just using this as an example where there are many examples. I'm in a new relationship, I'm in a new job, you know, but again, focusing on what is making you internally have well being and contentment is so much stronger than trying to control outside, external things. Like, I can't say, well, I need to make $10 million this year or I'm going to be unhappy. Because then I'm almost certainly going to be unhappy. And yet so many people like, oh, I got to be a millionaire by 30 or my life is over, or I get questions all the time. I'm 28 years old and I don't know what my quote unquote passion is in life. You don't have to know. All you have to know is that today I'm doing the things required so, so that I can reinvent.
Well, you know, and often those milestones are a means to an end. The money is a means. Money itself is somewhat meaningless beyond what it can then help you do or achieve or how you want to feel. Yeah, even then it's not a guarantee.
But, you know, I don't want to. I don't want to discount too much. Like, you need money to pay the bills and you need money to do certain things. But a lot of people take another step and then they're unhappy. So, for instance, I've talked about this on other things, but I know of one guy who's worth about 2 or 3 billion and has 60,000 employees. You would consider him a success in every way. And yet the one major story I've heard about him is that he was really, really upset and depressed. That quote, unquote, that goddamn kid Larry Page has 18 billion and I only have 2 billion. You know what? You know, so. So again, a lot of people, like, they need to have. They need so many things that money is not going to satisfy. Now, it's important to pay the bills. But like, I'll just give you an example. Over the past three months or four months, I've only lived out of one bag. And I've lived from Airbnb to Airbnb, not so expensive. But.
I wanted to prove to myself I could live completely out of one bag and not have any other possessions that I needed. And, you know, as long as you need less, you can always. As long as you expect less, you can always exceed your expectations. And. And exceeding your expectations is much better than being disappointed by higher expectations.
That's so true. And I'm always. It's funny, our good friend Dorie Clark, our mutual friend, the other night we were walking home from a dinner and we talked about the agency paradox, which is that on the one hand, self help teaches you can be, do or have anything, manifest what you want, and then on the other, sometimes all that trying and manifesting and pushing, pushing the river, if you will, is futile. And I'm often blown away both by how much capacity we have and how intelligent our bodies are. Not just our mind, our whole system, but also how little we know that actually, when you let life surprise you, and I know we've talked about things like this, that even better things happen or even. I'm really fascinated by blessings in disguise and reinvention, things that in the moment might feel terrible but end up being the absolute catalyst that we need to go to the next phase.
Yeah, absolutely. And, you know, you mentioned how, you know, it's not just the brain that decides things. Like, you have more serotonin in your gut than in your brain. And serotonin is an important neurochemical for determining whether you're going to be happy or not, or in particular, whether you're feeling like you're about to achieve your goals. That's when serotonin sort of lights up. That's why it's in your gut, really, because what's your most important goal every day is to eat and keep. Keep, you know, keep alive. So serotonin, which is so important to our feelings of contentment and happiness or sadness on the downside, you know, that's in the gut. That's why people. And that's where the, you know, inadvertently, that's why we say trust your gut or, you know, I'm not feeling it, you know, as opposed to thinking it. Like when some bad situation happens to you. And I'm sure I don't know this for sure, but I'm sure the same thing happens with the heart. Like, there must be some neurochemical activity there because, you know, trust your heart is often said as. As opposed to trust your brain.
And I think that's really important. I know when I've had big reinvention points, it's not like my brain decides rationally. Okay, now you have to do X, Y, and Z. It's sort of like my stomach or my heart or physically, I might fall more or I might get sick. Bad things start to happen. When there's a fork in the road and you start to take the wrong fork, your body's gonna definitely tell you what it wants.
So true. I almost feel like reinvention benches the brain. Because the brain's usual tactics probably aren't going to work at 100% by definition.
Because your brain wants you to. Your brain, I'm going to treat it like.
Almost like a separate person. But your brain wants you to take care of yourself and to be safe. But it doesn't know what that means. It's not as strong as people think it is. So it just wants you to stay in what's familiar to it and not change. So if you start to do things that you've never done before, your brain's going to freak out. Like, what the heck are you doing? You were fine when you were sitting on that bench, and now you're running a marathon. Like, chill out for a while. But you might say, no, I really want the challenge of the marathon. And this is good for me to kind of exercise and get ready for it and so on. But the brain's not going to be happy with you if you do that. That's why you have to trust these other parts of your body. Now people will say also maybe trust the supernatural, but ultimately it's always gonna happen in your body, what's going on outside of you.
I agree that compass, one of the things, item B is you start from scratch. And I think that too really triggers fear in ourselves.
Well, again, I'm gonna throw it back at you. What happened to you? And I don't know the answer to this. What were you feeling the day after you left Google? Well, first of all, you were at scratch to some extent.
It took me about a month. The interesting thing was at that time, yeah, I gave myself six months to move to New York City and try and make it. And now I'm coming up, if you.
Can make it here, you can make it anywhere.
You know, I had ringing in my mind and there, there was again a soul calling to be here. And I thought, am I insane? I'm leaving Google. And now I'm trying to start a business in the most expensive place in the country. But in my mind, if I'm going to do this, I'm going all in. And I have to say that my moment of starting from scratch inspired Pivot, the book that's coming out. Because I got to zero. I had to put three months down in order to stay in New York. I had been here two years and I had to put three months security deposit down because I'm an entrepreneur and first month's rent. And so that wiped out my cash savings. And January was coming up, it was dark. I was eating power bars for dinner. I'm staring out my window feeling like, is it jig up? Like, am I delusional? Here, Here I've been running my own business. It had been three years at that point, and I thought, shoot, maybe I'm done and I need to leave New York and go find a job. And I had that. The voice was very strong in my brain saying, you're delusional. You're such a failure. And that's what really felt like from scratch. And I love books. I'm a total bookworm. I remember looking at my bookshelves, being angry that I've read hundreds of business and development and financial books since I was 15 and none of them were answering this question of how do I rebuild from scratch? And so there's a long answer to.
Your question that's interesting. Why? Because a lot of them are about empowerment. And I feel like a lot of those self help. But you know what the problem with a lot of those personal development books are, is that they're lectures as opposed to stories. So I would rather hear, like, you. Like, I won't say the person's name, but there's one great self, self help or personal development author, who describes, like, how he visualized one thing and then two years later, he had everything he had visualized. But he doesn't really tell the story of how he got there. Instead, he starts lecturing, he starts giving lessons about what you should do. I would rather hear about what he did because then maybe I'll follow what he did and get there as opposed to him telling me what I should do. Because if someone's lecturing me, it's just like in school, like, I hardly ever paid attention to the teacher I wanted. But if they told me a story just like people have for the past 5,000 years in humanity, I'm gonna listen to the story rather than listen to the lecture.
Right? And that's why I think your writing is so powerful and resonant. And I remember reading it when I was going through all of this feeling like, okay, this is. You really showed and wrote about how you rebuilt from scratch and how you face the problem one hour at a time, one day at a time, one set of daily practices at a time. And for me, I think sometimes we have to hit that moment. And this is what I didn't feel. The books I had read, there's two things. One, there's describing. What does it feel like? It's terrifying when you're in that starting from scratch feeling. And at that point I realized I needed to because I had some financial. I've always been sort of like, worried about not having enough. And it really forced me to confront that and also have more faith in just kind of surrender. I know that's something you and I have talked about, but then the second piece is on a practical, tactical level, how do you do it? How do you rebuild?
Right? So the surrender is key, right? Because else that's that delusional part of your. Without surrendering, that's that delusional part of your brain saying, oh, my God, the jig is up. What am I going to do? I'm going to have to get a job, that. That whole thing. So. So you got to surrender that and just say, okay, I'm doing this. I had given myself six months. I knew I had six months to, you know, time to do it in. So I got to just Surrender for a little while longer and maybe hopefully forever. But what were the practical things you did? Like, how did you. How do you do it?
This is.
You have a more interesting story than me, so I want to hear it.
Not even this is where the book is coming from because I thought nothing I've read is working. I. I'm now at zero. I don't know how I'm going to pay the rent in two weeks. And I just thought something's. What am I missing here? Like, I've read everything I can read. What I started to do was I looked and I had hired a business coach and that we spent so long looking so far outside myself. But I thought, I have to pay the rent in two weeks. What has worked in the past? I went back to all my former coaching clients. I interviewed them about what they would find helpful. I ended up creating a program called Brilliant Smarter that's now my momentum community. And I just thought, I just gotta start with what's already been working and people were hiring to speak. I had a book, I had a blog. I had to recognize that I wasn't starting from scratch.
Ah, that's great.
And there's another paradox. Like you are starting from scratch and you aren't. You bring stuff to the table.
But you know what? Another interesting thing you said is you went back to all of your old clients. People don't realize your best new clients are your old clients. So did your old clients start re upping with you as a coach or bringing you into other opportunities?
I created something custom for them. I had a hypothesis about what might be helpful and I realized I already had a relationship with these people. They were so joyful to work with. Why am I scratching my head trying to find these like invisible mythical customers?
Right. Why did you give up on them anyway? Not give up on them, but why were you trying to transfer away from them?
Anyway, we had finished our coaching engagement. Oh, this was over. I've been coaching for probably five years at that point. But then I kind of realized, well, what could I create that's an ongoing program? So it was lower level and it was lower cost than my typical one to one package. But it was a little more scalable and I would create a sense of community around it. The brilliance barter concept is what's brilliant? Okay, tell me, take a penny, leave a penny. So if you're gonna ask for help with something, give help or feedback. It could be promoting something. It could be weighing in on a logo.
And how have you seen it work for your the customers of this.
It's been so fun and I've used it for my book. Like, which author photo should I use for the back cover? I don't always know. So I love having a forum and for me, the take a penny, leave a penny is key because nobody, nobody. We've all probably been in those Facebook groups where it's just a bunch of like self promotion shouting.
No, when you have a face, when you find a good Facebook group, that's a real community. It's a real special thing. That sounds weird like, oh, social media, blah, blah, blah. But I actually am a member of a few Facebook groups where we become friends and it's great, but. So how many people are in your community now?
Now it's probably about 100.
So that's great.
Yeah.
And I. I'm gonna sign up. How can I get in your. Invite me into your community?
I would love that. MomentumCrew.com that'd be amazing. That kind of brings me to the next one.
So letter C. You're avoiding questions about yourself now. What? I just wanna.
You have so much wisdom to share.
No, but you just told me you started from like scratch. You were worried, you were nervous. That's like the primal American story now is, you know, and that's the story we all need to survive. And you've. That's why you wrote your book. You have value, you know, describing that.
Thank you for saying that for me. What I learned in that moment was a few things. I really clarified my known variables. It's kind of a technical term, but I found my grit. I found where my grit was hidden. I found that.
That's a great phrase. You found your grit.
Thank you.
Pivot or get pivoted. You've had two good quotes out of this.
I should write a book.
I'm going to write the post on this.
Yeah, perfect.
I felt like hell. No, I'm not leaving New York City. Like New York City is gonna have to drag me kicking and screaming out of this place because it is the love of my life. I'm not going anywhere. I love it here. I'm alive here. If I move anywhere else just to leave my money fears my soul. A piece of my soul will go with it. And so it really solidified what I did know about what I wanted. And it motivated me to work hard. So say more.
Well, in 2001, 2002, I went totally broke and lost my home and everything. And I got so scared, I let my brain take over in the way you didn't let Your brain take over. Not that New York you have to stay in to be successful. You could be successful from anywhere. But I moved. I didn't want to move out of New York, but I thought, okay, I'm gonna. If I don't move out of New York, I'm gonna go broke. So I moved 80 miles away or 70 miles away. The middle of winter was a blizzard. I didn't leave my new house. I moved into a much smaller house, which is hard to do when you're coming from New York City, because New York City, everything's already kind of cramped in. And I just really started from total scratch. But I was scared. And I wish I. In retrospect, the one thing I wish I could change that. I wish I hadn't been so scared. So.
So what would you do differently next time when you have that starting from scratch feeling?
I think I was depressed, so I think I would have done things to focus more on making myself better, and then I would have sought out more opportunities because pretty quickly I. I did actually come out of this depression and I focused. This is when I started focusing on my physical health, my relationships with friends and other people, my creativity. I focused on every day. I made sure I created something. And in particular, I would write down ten ideas a day. So that became the key to any success I had afterwards. Just that one simple activity, doing it every day because it compounds and multiplies, and then just making sure to be grateful every day as opposed to. I had so much regret over, like, losing all my money. This is, you know, 15 years ago or 14 years ago. I had so much regret over losing all of my money and losing my house and disappointing my family. I couldn't get out of that cycle of regret. But I call that time traveling, where I kept. I kept moving, moving. I kept time traveling to the past instead of, like, trying to make my present better. And once I started making my present better, all sorts of amazing things happened where I really didn't. I didn't need to have moved out of the city again. Not that the city is like the mandatory for success, but I really didn't need to make so many changes that I did. I had this scarcity complex, and I felt I really needed to, like, shut everything down immediately or I was going to die. And I succumbed to that feeling and took many years to get out of that scarcity complex.
It's interesting because. And there's a book called Scarcity where it really puts a grip. You're in the grip of scarcity, and it Changes how we think when time, money, or resources are scarce. But I'm curious, how do you. How do you walk that line of. Because there is also a very real fear we cost money to live.
Yeah, so. So that's true. That's why I wouldn't discount money at all. You really need to live. You really need money to live. You don't need money for anything else, though. So you just need money to, like, pay your basic bills. Everything else is a luxury and luxuries that you might not want or need. You might think you need it, but you don't really need it. I mean, for me, a much greater luxury is reading a good book than flying on a private jet or something. So. Because I don't even like to fly at all, so any flying at all is, like, bad for me. Not that I'm afraid of it. I just don't like it. It's a drag, but pun intended. Yeah, exactly. Sort of. I think you made a stretch there. But I think what happened, what I really noticed was when I was healthy and writing these 10 ideas a day down, I felt creative and that. And while I was doing that, I didn't think at all about money. And whenever I then started other businesses or engaged or I was engaged in other endeavors that were successful, like writing a book or writing, you know, post or doing a podcast, I never once thought about money during those times. And then the money magically. I don't want to say magically, but the money sort of took care of itself then. It's almost like the more I focused on things that were more important than money, the easier it was to make money. And that sounds almost trite, like, again, it sounds law of attraction ish. Which is not true. Because when I focused on things that were more important than money, like, let's say, coming up with ideas to help people, those were then just like you were interviewing your clients. How can I help you more? You then sort of very naturally build upon this creativity and these relationships to build something that almost trivially makes money. And it becomes much more real than a stable salary. Like now you've diversified your salary across, let's say, hundreds of people, hundreds of situations. Speaking, writing that your community, you know, and I did something similar. For me, it was like investing, starting businesses, writing books, speaking also. And now so many other things. Like maybe Now I have 10 to 15 different sources of, you know, how revenues in my life come in. And it's all a function, not of wanting money, but it's a function of being creative. And Wanting to help people and that, but. So you can focus on that. But you really also need gratitude to stop the time travel because that stops anxiety and regret and you need good relationships so that when you are creative, you have people you can talk to about it. And, and you need your physical health because again, if you're sick in bed, you're not going to help anybody, you're not going to be creative. So those things become so much more important than money. And then money is like, if you give yourself time, money is trivially a byproduct of it. And how do I know this? Now? I know this for myself, but I started writing about this in 2010, I swear to God. Now I get probably a thousand emails a day from people thanking me and they describe to me their stories. So I see the stories of what happened to them. Once they start writing down 10 ideas a day, it changes how your brain works and it changes everything else in your life and it just works. So that's like the most critical thing in all of this.
That's amazing. And it's directly within your control. I love that those are the bootstraps that sometimes people hyper focus on the money, but actually, as you're saying, making a list of ideas, making your gratitude list, focusing on the physical health, that, all of that, that's what ultimately just step by step gets you out of that place, that hole. Do you think that reinvention necessitates starting from scratch or can we get better at it so that we don't have to always wipe out to zero?
Well, a, I'm going to knock on glass here, but.
Hopefully you don't always have to start from scratch. I've been starting from scratch at least three or four times now. It's really ugly and painful. I never want to do it again. I mean, the first and second time was maybe that was painful enough. And then the third and fourth time I was like, what the heck, I can't go through this again. But now I hope never to go through that again. But at the same time, it's like I said in that very first thing, reinvention never stops. Like I'm always. This month has been maybe the biggest month of reinvention for myself in the past 10 years. So, you know, it's constantly happening, it's constantly unexpected where it brings you. When you set out on a journey, there are always forks in the road. You don't know where they're going to be because you don't necessarily have a map on your journey. And then you kind of have to decide, and that's reinvention. You have to make. And not all of your choices are going to be good, so you have to give yourself permission for chaos also. And so many people say, no, this, this, this, and this are going to happen. I mean, I remember in fifth grade, so fifth grade, I was 11 years old or 12, you know, whatever your age you are. And I remember saying to this girl that I had this crush on in fifth grade, okay, well, we're gonna go to. We're finish high school, then we're gonna go to college, and I'm gonna be a lawyer, which I never was. And then we're gonna get married, and we'll have two kids, and we'll have a house, like, right next to where, you know, our parents live. Because you're still, like, you know, your parents are still your universe then. And then we're gonna grow old and we'll get sick and die, and, you know, our kids and grandkids will be around. So I'm telling this to this girl, like, in fifth grade in a lunchroom cafeteria, and she was, like, looking at me like I was completely insane. Like, I don't know. Cause whatever, I was a dorky kid. But obviously none of that came through, and none of it ever comes through that you think is going to happen. Fortunately, that girl from fifth grade is still Facebook friends with me.
But that's awesome.
Yeah, but that's about it.
Wow. Well, it's really powerful to hear that even this month is a big focus of reinvention compared to the last 10 years. Have you learned anything new this time around that might not even be in the ultimate cheat sheet?
Yeah. I think when. Other times when I've had to reinvent, I was ashamed of it, and I was ashamed of telling people bad things had happened to me, or I was ashamed of telling people, well, now I'm going to try this, this, and this. Now I've been reaching out to friends and making new friends, and I realize what strong goodwill I've developed by being a good friend over the past few years. I've never kind of let myself, though, allow other people to be my friends. I've always been the one for people to come to, but now I've been kind of letting go of that myth for myself, and. And it's been amazingly powerful. Even. Even though maybe other areas have been like, whenever you're going through a weird time, you can't always be 100% in every area of your life. But I would say even while Other areas might have slipped a little. The friendships have built up this, like, solid steel safety net for myself, and that's been extremely valuable. And again, not only for me, just emotionally, but financially, creatively, and in every aspect of my life.
Wow, there's so much gold there.
1.
I love that this time around you're not ashamed of it, that you're proud to say you're owning your reinvention in a sense, and that must be a relief in itself.
Yeah. And again, reinvention does happen constantly, but sometimes it's more than others. Yeah. So, like, you know, in the six months earlier, too, I was maybe publishing a book I was reinventing in various ways, but there were kind of things that were sort of, you know, it wasn't. You know, sometimes things happens that you're expecting, and sometimes things happen that you're unexpecting. So if that's a word, but you kind of have to roll with it. And that's what I realized this time, when things happened that were unexpected to me.
I love what you said, too, about friends. We were talking before we hit record. This line from one of your recent posts, I absolutely love. And we'll put this in the show notes. It's from A post called 10 Steps to Avoid Giving Up. And you say, this is God. A prayer disappears into the air. A request to a friend saves you on the importance of friendship.
Yeah. Because think about it, like, when you're with a friend or a loved one or whatever, that's something that's very real, that's happening there, and you feel really good. You feel warm, like in your heart, and you feel warm all over. And then things can happen out of that, like, ideas can blossom and. Or you could have accountability on ideas and you can figure out how to get healthier. So a lot of things blossom from friendship if you're just in your head, like wishing for things or praying for things. I don't want to discount, like, anybody's religion or religious beliefs or faith or whatever. Faith could also give you a feeling of warmth. But I really find that more real to me than anything has been the connections I have between human beings. And that's, again, almost an evolutionary thing because, of course you feel better around people. That's how the human race has survived. If everybody was a hermit, you know, genetically, we would have died off as a species. So it's very primal to get a lot of strength and, you know, from your friendships and from your partnerships and from your team and from your tribe and from your group and whatever.
I never realized how utterly important it was and how primal and evolutionary that importance is. So, I mean, anybody listening to this, the one thing I could recommend, other than the 10 ideas a day, and, well, I recommend all these things that I'm saying, but just reach out to a friend. So you know what I. A typical thing I do is I'll look through my emails from like 2006 and I'll figure out, oh, someone sent me an email and I never responded to it. So I'll just respond like, someone might send me an email in 2006, hey, would you like a coffee? I never responded. So I'll just write back, sure. And right now. And you know, sometimes they're like, whoa, like it's nine years later. I'm glad you finally responded. And then I'll have coffee with that person. Suddenly, like an old friend turns into a new friend. And so many things like that happen. Just sort of the blessing of social media to some extent, because that's how like, look, I would never stay in touch with my fifth grade friends if it wasn't. It wouldn't be like I would call up my 5th grade friend and say, hey, what happened to you yesterday? What did your dessert look like? But unlike Facebook, I can see it and I still feel those feelings of friendship. And in some cases I can take it one step further and communicate. And if you think about it again, it's sort of primal. Humans started off as tribes, then we were kind of villages, then cities, then kingdoms, then empires. And now we're these huge empires which no other species has. It's very. Something very special about being human. And now social media kind of covers the Earth. Like it's this weird next step in our evolution in a weird way. And so I think taking advantage of that in positive ways as opposed to the negative ways people do often do, is very important.
Right. I think reinvention, too can be such a catalyst for letting old relationships dissolve, ones that aren't going to kind of fit again. It's sending people off with love and compassion, but I think it can clear older friendships or friendships that aren't maybe serving both people's highest interest. And then one thing I found really exciting about my most, like, let's say my biggest recent reinvention, because I'm with you, it's constant, but it's just what cool people come into your life. And in these moments of reinvention, in a way, for me, I find I'm more open in a sense. Well, once I process and can get out of My head and out of the house. And then it's so exciting that by us making these leaps in our growth and our consciousness and what we. What's true in our heart that I love the way that people kind of show up magically.
No, it's really true. And think about really how like you and I met, for instance. We met because, again, because of social media. Really, like we were sort of part of this extended period social media tribe in New York City to some extent, or I don't know if tribe's the right word, but scene might be the right word because it's not like we're in a tribe. Everybody sort of has their function and of what they should do and seen is more like kind of haphazard and like, oh, hey, I ran into you. But we know each other through X, Y, Z and abc. So we're able to kind of figure out like, okay, let's try something. Let's do a podcast together and stuff like that. So again, it's important to take advantage of what we have now in front of us and all the different ways we can bring in good people into our lives. And like you said, I think it's really important to send away, at least for now, the bad people, but with love, like, not with anger, because anger is really a form of fear and.
Attachment still to that person.
Right, Exactly. So you have to kind of sincerely wish people the best, but if they're bringing you down, you have to send them off. And now that sounds cruel. I don't mean to say if someone has cancer, they're bringing you down and you should send them on their way, like go have chemotherapy and see you when you're. When you're better. You kind of have to stick with the people who stuck with you, you know, to some extent and particularly it all, you know, in a loving sense. But if someone's just their only function is to drag you down emotionally and mentally and physically, then it's really important to protect yourself. Even if there's other positive things there. You have to protect yourself.
Absolutely. On the subject of people, let's talk about mentors because you have some really interesting thoughts and by the way, on the friend, I call them friend tours.
Friendors. I like that.
Just like your daily practice.
Another thing I gotta write down.
Yes, it's in the book too. You can write down 10 ideas a day, but you can also email one person a week and ask for coffee or two a week or set up. I used to have a call back when I started blogging. Back in 2007, 2008, people would make fun of me because I was always asking to have a call and I'm using air quotes for all of you listening. And they thought it was kind of cheesy, but it was how I connected in those early days. And I just, even now, I think it's kind of nice. Like you can make a daily practice out of connecting with people, especially if you're naturally more introverted or.
I think that's really important. So I'm really, you know, nobody believes me on this, but I'm like super shy. So I have to constantly challenge myself to be in situations where I'm gonna meet people and talk to people else. I'll stay in the house for six years in a row. And I think that's really important. But also, I want to add on the mentor thing. It's also important to read because when you read, like, let's say you read someone's autobiography now, you just got their entire curated life and their best thoughts about their lives in just a few days time. So that became. That person, just became a virtual mentor for you. And it's very important to read a lot, like, because every book is, every book is a curated life that becomes your mentor.
Yeah. Until you've kind of milked the wisdom from the book. I don't, I think people obsessed, obsess over asking for mentors or having to find the mentor, thinking that it needs to be this live, ongoing, super committed relationship. But I'm with you. And I love how many times in this reinvent yourself checklist you talk about, go back and read 200 books, read 500 books there. I put so many smileys where I left. And you're just like, go read more books. Like, oh, it's just, it's awesome.
Right? Like, one thing I think, if I remember correctly, I think I say in there, if you're trying to find what your passion is, go into a bookstore and see which section of the bookstore you're willing to read all of the books in that section. Because that's probably something you're passionate about. And I'll bet you even more it's something related to something you were passionate about as a kid.
Totally. This is a. It's a letter.
A, A.
You say, I can't read 500 books. What one book should I read for inspiration? And your answer is give up.
Yeah. Because one book is not going to change your life. I love it. I'm even saying that about my own books. You can read all my books. And it's not gonna, like, change your life. What? Change your life is an ongoing practice of reading. Now, I don't mean absorb everything you read because no one could retain. I retain 5% of maybe what I read in a book or 2%. But just having a practice of reading and, you know, not, you know, getting distracted too much while you read, which is really hard for people right now. It's hard for me, but it's just such an important practice.
I agree.
One of my.
The favorite things too that you wrote about mentors, you say, don't give them more homework by saying, how can I help you?
Yeah. So many times people write to me and say, hey, I really want to help you. How can I. What do you need help in? And I'm like, whoa, I don't. That's really great that you want to help me, but I don't know you in the first interaction you have with me is you gave me a homework assignment. I'm already.
Right.
I already have enough homework, you know, and when I don't have homework, I'll spend time with my kids or loved ones or whatever. But now you want me to return a message to you with an assignment.
And there's actually a cost of are they going to do? Well, you have to give the instructions, like, yeah. And I also kind of. There's two kind of pet peeves questions I have around mentor, and it's. I know people don't do this intentionally, but one, can I pick your brain? Because who wants their brain picked? It just sounds invasive.
Right.
And then the second, this thing of how can I help you? Sometimes I feel pressure. It's like a bait and switch. Then I'm going to have to say, well, how can I help you? And I actually don't know yet if I'm ready to how much I will want to give. I'm generous by nature, so I would rather that person, just as you've said, like, give your mentors ideas, don't make them do the work of now having to figure out how to help you.
Well, I would say it's that one technique that changed my life a lot, starting in 2002, then in 2006, then in 2010, 2011, every year now, which is do enough research about the person you're contacting so that you can come up with ideas about their lives or businesses that they would never have come up with. So that's really the challenge if you want a mentor or if you want even contact with somebody, because, you know, many people are busy so if you really want to make contact with somebody, really do the work and earn it, and that's very hard to do. But I started doing that in 2002, and the results were, like, so amazing. It defined entire careers for me. It made me, literally, that one technique made me millions of dollars. So, wow.
What was that opportunity?
Well, I'll tell you a couple opportunities. So one person. So I wrote like, well, first off, I wrote like 40 people and I said, can I take you out for a coffee? Like, you're. You're a great person. Can I take you out for coffee? Zero people responded. Because it's not like Warren Buffett, who I had the nerve to write. It's not like Warren Buffett's gonna say, you know, Gladys or whatever secretary's name is Gladys, like, stop everything. James Altucher wants to take me for a $50 cup of coffee. Like, he's never going to do that. Like, he doesn't need me. He doesn't need my coffee. So.
Nobody responded. So I figured out, okay, what's happening here. And that's what was happening, was I was offering nothing of value. And so Instead, the next 30 emails I sent out, I really, I, you know, listed 10 items, how I can. What they could do in here's ideas of what you could do that I would be willing to pay money for. So I thought I had to really think hard, like, what can this person do that I would actually pay for? And so with one person, I wrote, Here's 10 ideas of things you can write that I would read or even pay to read. Another person was a hedge fund manager. I said, here's 10 pieces of software that I wrote that I think aligns with your philosophy of investing and that model the stock markets and everything. So it's hard work that I put into this, you know. And so that was out of 30. Those two responded. Two out of 30 where I really put in the work. So it was, you know, maybe 100 hours worth of work or more. And two responded. One person ended up allocating money, so I started a whole hedge fund business. And then the other person said, wow, these ideas for articles are so great. How about you write them? And that's how I started getting paid to be a writer. So suddenly, out of just that batch of emails, I started two different careers that pretty much lasted forever. Like, I'm still ongoing in those careers. And, you know, and then the. The writing guy, he ended up buying a company I started for millions of dollars, like, four years later. So it all kind of Started from those seeds of, you know, sending out those emails.
Wow. It's like idea stocks.
Yeah.
Invest in a whole portfolio.
That's a great. I got to write. Where's my notepad? I got to write down all these things you're saying right now.
We'll put them in the show notes.
It's okay. Pivot, don't be pivoted.
Yeah.
Gosh. All right, we're gonna have to re listen to the podcast, the real gems.
Okay, so point F. I'm gonna skip three types of mentors for now. Point F is time it takes to reinvent yourself. And I love you have a kind of a five year outline now. I think this whole podcast should have the paradox attached, which is you're constantly reinventing and it might take five years, this certain incarnation. I'm curious to know, do you still think it's about five years or because the economy is changing so quickly, are we gonna have to kind of get. Make that cycle time even shorter in a sense?
Well, I think the five years. So I say it takes five years to reinvent. So if you're like a surgeon and you want to be a lawyer, you know it's gonna take you five years to become a lawyer. Or if you're, you know, professional accountant and you wanna be a stand up comedian, you probably not going to have like good paying jobs as a stand up comedian for at least five years or more. So just in general, you need to put in a certain amount of time and effort. And I think nothing's going to change that. It doesn't matter about the economy. But I do think just because you start reinventing doesn't mean you can't say, let's say you want to change from being an accountant to being a professional writer. You could start saying you're a writer from day one and you could start writing and you could publish a book in a year. It's just that you're going to keep learning and learning and learning and you won't be kind of an expert for those. You won't be like among the best in your area for five years. Because that's just. I feel like that's kind of like a law of the universe almost. So I've noticed that for myself it takes five years. So I've reinvented myself maybe seven times. And it's. And you know, sometimes they overlap, but it's five years seems to be kind of, at least for me, kind of a constant.
Would you say, because. Did you start blogging? Was it around 2010? That you.
Yes, around 2010. Yeah. In fact, I would say like this month in 2010. So it's like five years. So now I'm looking, now I feel tired, a little bit of it. So not that I want to completely stop, but I need to kind of think about, well, how am I reinventing what I'm doing? So. And it's important to recognize when you hit those points so that the reinvention can continue or else you die. Right. So you don't want to do that. It's no secret that when people retire, like with the. Within a year or two, their deaths spike up. So as soon as you stop kind of trying to improve and change and if you just sit in front of the TV and say, okay, well I could do this the rest of my life, you're gonna die in one way or the other. Maybe not physically dead, but some death will happen.
So many people I talk to, I call them high net growth. So there's high net worth individuals and high net growth. They often have a lot of money as well because they're so growth oriented like you're saying. But they don't really have plans to retire. I mean, yes, there's this location, independent dream work from anywhere, however many hours a week you want. Yes, people want freedom. But when I talk to these particular group of people, they don't. Retirement's not a thing they want to enjoy. They love their work and they want to continue in some capacity. Yeah, I have to read this quote so that I'll be listening in case. If you're not yet familiar with James's work, it just makes me laugh. I have smileys everywhere. This one is. Sometimes I get frustrated. In years one through four, I say, why isn't it happening yet? And I punch the floor and hurt my hand and throw a coconut on the floor in a weird ritual. That's okay, just keep going or stop and pick a new field. It doesn't matter. Eventually you're dead and then it's hard to reinvent yourself.
Right. And that's the whole thing, is that you kind of, you can be frustrated while you're reinventing. That's going. You actually, you have to be frustrated while you're reinventing because you'll always recognize a gap if you're really serious about what you're doing. There's always going to be a gap between where you are now and where the people you admire are. And so you're going to be frustrated until that gap starts to close. So, yeah, so it's good to feel frustrated. If you're not frustrated, you know, just. And again, like, eventually you're going to be dead, so it doesn't matter anyway. So you might as well just keep going. And, you know, if this is an area you love and you want to close that gap with the people you admire, you just have to keep going.
I feel like people sometimes obsess over that gap, but actually, I think the big secret is that we love that complexity. We love the challenge. We would be so bored without it.
And it's scary, too. It's really scary. I look at right now, how am I reinventing myself and what do I want to do? And I see how far away it could be. The ways I want to reinvent myself. It's always scary, like, oh, am I going to have to spend five years on this now? But it doesn't mean you're not going to get pleasure out of it for five years. You can get pleasure out of it, of it tomorrow. So that's what I've noticed also, is that every step of the way in reinvention, you can get pleasure out of it. It's just you're probably not going to be where you set out for five years.
So are there any, as you look ahead and what feels stretchy and edgy to you, any that you feel willing to share?
I'd like to. I've always wanted to do this for the past 25 years or more, write fiction. And I keep starting and stopping and starting and stopping. And I feel like each time I start, I get a little bit better. And I read fiction every single day. And I have many friends and mentors who are excellent novelists and fiction writers.
So that things like. But you always have to prioritize, too. And I like this one quote from Warren Buffett. He said, Write down the 25 things you'd most likely to. That you would most like to succeed at. And then take the first five and put them over here and take the next 20 and put them over here. And then. And then throw out the next 20 and never look at them again. Because he says every time you're going for that bottom 20, even though it's something you want to do, it's going to take away from that top five. So just throw out the 20. And so you have to really make sure you're only focusing on those top five things. So it's important.
That's really interesting.
So, for instance, wouldn't it be great if I could be a professional rapper? Well, that's definitely on my bottom 20, it's not in my top five, so I'm not going to think about it for another second.
I also feel like sometimes if those random quirky things are meant to happen, that life is not linear and that sometimes if we take our focus off, those things will come back. Maybe not in that exact way of.
You're so right. Yeah. But like, for instance, I do a podcast right now. I've had a ton of rappers on my podcast. Like, instead of just everybody thought I was gonna do this podcast and just have, like, entrepreneurs and whatever. And I've had plenty of entrepreneurs, billionaires, that whole thing. But, you know, then I've had. When I was a little kid, I wanted to be an astronaut. So I've had two astronauts on my podcast. I've had rappers, and, you know, my first business, my main clients were music labels that focused on rap. So I've had this interest since I was a kid. And I never, of course, became a rapper, but the thought of it is kind of just ludicrous to me. But it's kind of permeated everything I've done in life.
Even though you wouldn't think that, like, when you. You wouldn't associate that with me, so. Or I wouldn't even associate that with me because it's been far down in my bottom 20, but it's come. It's kind of manifested into my top five many times.
Well, that reminds me of one of the things in the reinvention list, which is you said, what if I'm passionate about two things? What if I can't decide? And you say, combine them and you'll be the best in the world. It's just fun. Maybe that's not one of your two best, but, yeah, it's a thread and it brings you joy and you get a kick out of it, and it makes you a more dimensional person to have these random, surprising interests.
Well, you look at. You look at all of these. You look at almost the invention of any movement in art or science or in any field really. And it's almost always like, if you look at, like, I don't know, like, the guys who discovered DNA, I don't think they were biologists. I think one was a chemist, the other was a physicist, and they knew biology, of course, but it was combining from different areas that how, you know, helped them model the double helix of DNA. And then they won the Nobel Prize because they were like, suddenly the experts at biophysics or biochemistry, whatever it was, they combined. And so it's always this combination.
I Remember thinking about this when I was considering graduate school in mathematics and I was looking into it, and the people I spoke to said, it's really, really hard because you have to go so deep down mathematics to come up with something new. So if you're only interested in one field, you have to go too deep into it to find something new. But if you combine two fields, you don't have to go as deep to be like, again, the best in the world at it. So nobody, for instance, was making websites for record labels at the time I started my business. So I was the best in the world at it. And we developed such a brand of being the entertainment website development company that the company had value and we got acquired. So that was a great thing.
That's so interesting. One question I always find fun is asking how three totally random seeming things, what they might have in common. So. Okay, humor me for a moment.
Okay, I'm gonna humor you.
What do you think that rap chess, because I know you're an avid chess player, rap chess and mathematics have in common.
Rap chess and mathematics? Well, chess and mathematics is almost an obvious thing because many great chess players were mathematicians. There's a strong interrelationship between, you know, you have to do some kind of abstract thinking. So a mathematician, before he comes up with his great mathematical theory, he has to. And just like Einstein had to picture, well, what would it be? Before Einstein came up with any theory at all, he was just sitting around as like a clerk in this patent office and he had to picture, what does it mean if there's a guy traveling the speed of light looking down at a guy standing still? And so then, so he was just picturing something abstract. And then he developed the entire mathematics to come up with his theory of relativity. So it's the same thing in chess. Well, here's my position now, you know, and I like to get into a position where I checkmate the other person's king. How do I get from here to there? It's again, you have to think, okay, what are the 10 steps needed, the 10 moves needed? So mathematics and chess, there's a strong relationship already. Rap. First off, a little trivial note. The Wu Tang Clan, one of my favorite rap groups, and I did all their websites, they were really into chess. So they were, in fact, their biggest album is the Mystery of Chess Boxing. They were into chess and boxing. And so they were all into chess playing and so on. So they saw this connection too, which is that when you do any kind of music, again, there's a strong connection between music and mathematics. You have an idea in your head of what you want, you think abstractly and then you have to fill it in. Well, here's the notes of how I can get there. Here's the beat of how I can get there. Let's pull in this old 1960s song and distort it a little bit and then say these lyrics on top of it and. And you'll. You'll get there. So all of them have in common, this kind of abstract thinking. And if you're good at one, chances are you're going to be good with a little bit of work at the others. So I think that's what attracted the Wu Tang Clan so much to strategic thinking. Also, like, they. They strategically manage their careers in a totally unique way where they never assigned themselves to one label. They signed them, they, they formed one kind of company and they, as a group, they worked with one label, but then as individuals, they worked with other labels. So no one label could ever control their company, which then dividended out all the profits to the members of the Wu Tang Clan. So that was a very strategic way of thinking that no other rap group had ever thought about. And that allowed them to make a lot more money than the average rap group. So. So again, chess is often you think of it as. Along with. It's like a war. You have to think strategically how you're going to win and protect yourself in case bad things happen. Like, what if your label hates you all of a sudden? No problem. We have 10 other labels we're associated with. So that's how they dominated the music industry for a decade.
So that's really interesting. I mean, that fits with your choose yourself.
Yeah, totally. The Wu Tang Clan and many rappers, actually. Because think about it, rap was sort of the rap and grunge were sort of like the last musical movements until pop sort of dominates everything right now. Although now there's a resurgence in all these things because of YouTube stars. But, you know, a lot of rappers now come out of YouTube because you could choose yourself again as opposed to being dependent on the labels, but trying to think of other connections between the two. Oh, well, one thing I was thinking is, you know, if you take any area, if you take anything in life that has resonated over time and combine it with something that hasn't, you're still going to create something good. So I'll just give as an example, let's say. So I'm not saying anything about Justin Bieber's talent, but many people don't like, his music. But what if Justin Bieber sang a cover of the Beatles song Yesterday? Then I know I would like it because the yesterday has resonated so much over time. I know Justin Bieber has some talent because he was discovered out of YouTube. He already had tens of millions of hundreds of millions of views. So I know if you combine those two things, you're going to create a massive hit no matter what. And again, that's happened in rap many of times. They sample songs from the past that have resonated over time. Like the Fuji singing a version of, you know, Saturday Night Fever. You know, Night Fever, you know, became a huge hit. So that's how you kind of create good things.
Yeah. And then you're tapping into what's already working. And there's a whole playlist on Spotify called Acoustic Covers.
And I love that stuff. Yeah. Like, I love. I listen all the time. I have a whole playlist for myself that I listen to. Acoustic covers of Coolio's Gangster's Paradise.
That's so cool.
So you have all these, like, women mostly singing just, like, the guitar really slowly in this folksy way, singing Gangster's Paradise. And it's great. Doesn't even matter how talented they are. It's just gonna be great to me because I love that song so much.
Some of those acoustic covers of rap songs, you're right. Those are some of the best.
Yeah.
Because it's so unexpected, right? Oh, I love it.
Which reminds me, some guy who lives uptown, but he's on tour right now. He's, like, an expert at the ukulele. And so he's on tour playing the ukulele, and he told me he would, like, come over and teach me how to play Gangsters paradise on the ukulele.
There's a party.
Yeah. Yeah. So he's. He. I think we're going to set that up sometime this month because he's back from tour. Okay.
You're going to have to do us all a favor and, like, play some ukulele on a future podcast show.
All right, I'll do that.
Okay.
Yeah. You'll come over and tell me if it's good or not? Yeah, I'm confident.
Perfect. Okay. So one of the last major themes I want to hit on is failure. And I think, again, on an intellectual level, people hear this as a very sexy thing to say now.
Like, it's so funny you say a sexy way to say. I call it failure porn. Because it actually is, like, too much. Like, everybody now thinks they're qualified if they fail. But failure is only. Failure sucks. Like, it really sucks to fail. Yeah, but you, you know, so you. It doesn't qualify you for anything other than saying, okay. Qualifies you for this one opportunity, which is to say, okay, what did I do wrong? And what can I do better? Really? Even not the what did I do wrong? Because, you know, really, you want to be able to do better the next time. So it qualifies you to say, what can I do better the next time? That's the only thing it does. Doesn't qualify you for anything else other than to say, what incremental new thing can I do? And so failure and even kind of almost going right to the edge of everything you do so you experience a little bit of failure will always make you better. I remember a funny thing. I was talking to Nassim Taleb, who, you know, wrote the Black Swan and Antifragile, and I said, so he came on my podcast and I said, I really don't want to talk about economics because I don't care, but I'm really scared about one thing. And he said, what? And I said, well, I've never been sick. I've never been to the doctor. Never been. I don't even know if I've ever had a cold. And not because I'm so healthy. At some point I'm going to have a cold, and I'm just. I feel like I'm going to die, like, the second I have a cold, because I won't know because I'll be just that whining guy who now gets sick and dies. And he said, well, I don't know if he was, like, joking or not. And so I asked him, well, how can I be antifragile so that when I get a cold, I'm not just resilient, I come back better, or not just cold, but, like, sick or anything. And he said, well, how about. And I don't know if he was kidding or not. Maybe he was kidding, maybe not. He said, well, how about you poison yourself a little bit every day? And he was kind of right in that whatever you do, you should figure out what's the poison. How can you take a little bit of poison, a little bit of hemlock every day so that you become immune to it, and so you become even stronger as a result of it? And I thought that was very wise advice, even if he was kidding.
Well, we talked about this at the party, the flavor pill everup event that we bumped into each other at. My theory on emotional vaccinations that when you go through something very challenging, you sort of get that vaccination or inoculation against that type of a problem or situation or, let's say failure. So then when you're about to experience the next time, you only need a small dose and you're like, oh, yep, there it is.
It's so true. And I can say this like. Cause this is a big thing happening to me this month that, you know, doing those little emotional vaccinations along the way helps considerably survive. Like a big, you know, not only survive because that's resilience and survival, but antifragility is when you bounce back stronger. And that's incredibly important.
And I think the way, for me, the Path to Antifragility, because that was a hugely helpful book for me as well. And concept. I just love the concept. And in a way, it's as old as time. What doesn't kill you makes you stronger. But the way Taleb talks about it was just brilliant.
Yeah. He's so smart, that guy.
I know, I know. And I just.
Wouldn't you say he's maybe like, in the top five smartest people out there?
100%. And reading his books, they're so dense, but they're joyful, they're funny. You know, he's kind of arrogant. I just love that. He's absolutely one of the smartest. He is someone who the gap will always exist, but I will always aspire to his level of thinking and explanation.
Yeah, no, I agree with that. I'll tell you a story. So I mentioned two people out of 30 responded to me. Out of emails I wrote, a third person responded to me. That third person was Nassim Taleb. And I never responded to it. So that was in 2002. So in 2014, I responded to it and I said, okay, I'm sorry I didn't respond earlier, but can you come on my podcast? And he said. He responded right away. And he said yes. And not only. That was the only interview he gave that year.
Yeah, he doesn't do a lot.
Yeah. And it was just great. We did it in person, and it was so fun. And he's such a smart guy. But again, that's an example of going back through the emails and like, okay, I didn't respond then, but I'm gonna respond now. I'm gonna take the chance.
What do you think got him to say yes, given that he. I know he does so few interviews like that.
I don't know. And I didn't ask. So I was just grateful. Exactly.
That's awesome. I know. Yeah. The failure thing is interesting and I think it's what you said. One thing that I have learned is when we fail, we often look at what we did wrong and exactly how to prevent it. But I find it very interesting to unpack a failure and say, well, what worked within that? Even if it was only 5% and the 95% failed, what was the 5? And how can you make that 10 or 15 and 20 the next time?
Well. Well, the best way. And I've known this. You know this. You learn this anytime you take lessons from a professional. So when I was a kid, I took chess lessons from the US Chess champion. And we. He didn't care. So I, every weekend I would play in a tournament and I would bring my games and then we'd analyze them. He didn't care at all about my wins. He only cared about my losses. And so we would really, like you say, unpack the loss. Like, where did I go wrong? And then just over and over again he'd set up similar positions and I'd have to kind of power through to find the right move in that situation as opposed to what I did in the game and in the game where I lost. And that really is like such a powerful way to get better. It's, you know, you learn a lot by, you know, you learn the language of mastery when you try to master one thing and then you kind of have to repeat that. You know, once you learn the language of mastery, you can sort of repeat it over and over again in other areas. And if you don't know the language of mastery, it's good to read about people who have mastered something to try to kind of get it from second hand at the very least. So, for instance, reading Robert Greene's book, another one of the smartest people ever reading his book. Mastery is Such a Valuable Thing.
Yes. Speaking of books, you're hosting an event soon. Must love books. What are one or two of your favorites that you want to recommend?
Well, I'll recommend some nonfiction ones. I find it easier to recommend nonfiction than fiction because fiction's so subjective. But okay, we just talked about them. Antifragile and Nassim Taleb. Mastery by Robert Greene. You might not know this one. Actually. It just came out. So Matt Ridley is another one of those guys who's like, super smart. So he wrote the Rational Optimist. But if you just read anything by him, your IQ is gonna go up. I like Outliers by Malcolm Gladwell. So I like Freakonomics by my good friend Stephen Dubner. And on the fiction side, again, it's very subjective. Some people like genre, some people like literary, some people like short stories, some people like novels. But one book that's sort of like the book that writers read is. And I know this because I was fascinated. So I've read this book, like, hundreds and hundreds of times. I probably read this book a little bit every day. But then I was reading an interview with Chuck Pal. I don't know how to say his name. Chuck Palaniaca, the guy who wrote Fight Club. And then I read in the interview, he's read this book 300 times. And then there's another book. So I haven't said the name of the book yet. Then there's another book called the Writer's Bookshelf. And it shows what's on the bookshelves of every writer. And this one book turned out to be on the bookshelf of, like, 90% of the writers. So it's like the writer's book to get better at writing. And the book is a collection of. A very small collection of short stories called Jesus Son by Dennis Johnson. It's about a drug addict and how he kind of gets through it, or not even how he gets through it. It's very. You'd have to read the book to understand. It's short stories, but it's all connected by this character. A movie was made out of it, but the movie kind of died fast because the book itself is so amazing. You can't make. It's about the writing, it's not about the story. And that's why I think, to be a good writer, this is a great book to read, and I highly recommend. In fact, I almost don't want people to read it because then they'll look at what I write and see how many times I like. Stolen from this book. But it's a great fiction book.
All right. That just moved to the top of my must read list.
Yeah, it's a good book.
That's awesome. And of course, I will personally recommend Choose Yourself and Choose Yourself Guide to Wealth. I could also see you writing a screenplay at some point.
You know, I had. I had a couple opportunities to do that in this past year, but then I made the conscious decision it was in my other 20 and not in my top five.
Yeah, well, maybe the fiction book you write.
Yeah, maybe the fiction. Yeah.
And someone else can turn it into a screenplay.
Yeah, that could be awesome.
This has been so much fun. I want to read One more passage from this recent post. It just. Your posts jump out of the computer into my brain, and I'm so grateful for them.
Thank you.
And so I want to share this piece with everyone. A reinvention might not be a radical change. You might not go from truck driver to pro basketball player. You might just go from good person to better person. From incompetent to competent. From a good friend to a great friend. From being a slave to being free. From letting others choose when you should be happy, to figuring out how to choose yourself for happiness every day. All of the above. It's a practice. You might one day be an astronaut and the next a painter. That's okay. It's your sliver of life between two giant infinities. Fill that sliver with cake and gold.
Round of applause. Standing ovation.
Thank you.
So awesome.
What a great podcast.
Thank you so much for being here.
And I got you to tell your story a little bit in the podcast. You did.
You're tricky, tricky.
I am tricky.
Thank you for asking. I cannot thank you enough for being here. And where can people keep in touch if they want to read more of your work?
I don't know. You'll put all the links?
I'll put them all in the show notes.
Yeah, you can go to jamesaltucher.com I'm.
Feeling a hankering to leave people with one inquiry, one question they can ask themselves about reinvention for 2016.
Well, I would say, are you checking the box? Are you checking the box every day on your physical, emotional, mental and spiritual health? You have to do that every day. And that makes reinvention a lot easier.
Love it. James, thank you so much.
You're amazing. Thank you.
Thank you for all that you do.
Thanks so much for listening to this episode of the Pivot podcast. To learn more and get in touch, visit Jennyblake Me, where I blog about systems at the intersection of mind, body and business. Or find me on Twitter @jennyblake. And remember, build first, then your courage will follow.
Hasn't it always Sam.
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218: We've Gone Over-Bored (Part 2) with Michael Karsouny (Listen at Your Own Risk!)