Ten Percent Happier with Dan Harris - 68: Jerry Colonna, 'CEO Whisperer' and Reboot.io Founder

Episode Date: March 29, 2017

Jerry Colonna was working as a venture capitalist in New York City during the 9/11 terrorist attacks, and as he walked by wreckage of the World Trade Center towers, he said he felt like his "world was falling apart." Colonna went on to become a practicing Buddhist and in 2014 he founded Reboot.io, a CEO-coaching company where he serves as a certified professional coach for the heads of some of the most dynamic start-ups in the United States. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

It kind of blows my mind to consider the fact that we're up to nearly 600 episodes of this podcast, the 10% happier podcast. That's a lot of conversations. I like to think of it as a great compendium of, and I know this is a bit of a grandiose term, but wisdom. The only downside of having this vast library of audio is that it can be hard to know where to start. So we're launching a new feature here, playlists, just like you put together a playlist of your favorite songs.

Back in the day, we used to call those mix tapes. Just like you do that with music, you can do it with podcasts. So if you're looking for episodes about anxiety, we've got a playlist of all of our anxiety episodes. Or if you're looking for how to sleep better, we've got a playlist of all of our anxiety episodes, or if you're looking for how to sleep better, we've got a playlist for that. We've even put together a playlist of some of my personal favorite episodes. That was a hard list to make. Check out our playlists at 10%.com slash playlist. That's 10% all one word spelled out..com slash playlist singular.

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See, today, I love the man I am, and I am a freaking mess. From ABC, this is the 10% happier podcast. I'm Dan Harris. So, I guess this week is a dude known sometimes as the CEO Whisperer. He's a one-on-one coach for people who run some of the most dynamic and interesting startup companies and even larger in the country. And he's of course got his own business background that is really interesting and also kind of tumultuous. Jerry Kallona is in business circles a legend and he also has a long-standing

meditation practice which infuses in many significant ways his work with these CEOs. So ladies and gentlemen here's Jerry Kallona. I'll just start with the question I always start with which is how did you start meditating? So my gateway drug yeah, Pamba Children. Oh, let me just jump and explain Pamba Children. They're quite famous Buddhist none and author. Her books include when things fall apart. That's one of her best-selling books. Right. So you found one of her books or you met or what happened was in February 2002 I Had left my previous venture firm in Actually September 10th 2001. Oh

agreed to join Jeffrey Walker at JP Morgan. So we'll explain who Jeffrey Walker is a Big venture figure and also very involved in the mindfulness world now. Right. At the time, he was vice chairman of the bank. Yeah. Oh, okay. And he headed up the private equity firm and they had been investors in our fund.

I started officially in 2002, January 2002, that fall, if you remember this New York history, right, Dan Docteroth was deputy mayor for, well, Dan Docteroth was running the New York City Olympic bid effort, and then Mike Bloomberg won the election. Dan got tapped to head first transition committee and then became deputy mayor. And Dan asked me to step in B.co chair of the NYC 2012 Olympic Committee. This is relevant to the point I'm going to make. Fast forward February 2, 2002. I leave the offices of MIC 2012, which was in free office space downtown. It was free because nobody wanted to be down. At which point nobody wanted. I'm walking past the pile. It's smoldering and I

want to kill myself. My depression, which goes back to my childhood, had been building and building and building and building. I had been with Fred, one of the lead venture investors here in the city. Fred Wilson. Fred Wilson. And my heart was broken. And my heart was broken by 9-11. No, my heart was broken because my world was falling apart.

And I was 38, and I was miserable, and everybody thought I was successful, and I was hollow inside. Sound familiar, Dan? Okay. And all of it was catching up with me. My therapist at the time said I went to her and I said put me in a hospital and I'm done. And she said, what do you want to go to a hospital for? You're rich. Go to Canyon Ranch. You'll get a massage every day. So I flew down to Canyon Ranch and my sister, Which is where? In Arizona. Okay. Spa, fancy spa.

Fancy spa. And my sister Anne gave me a book. She gave me two books. And I took a third with me. She gave me Let Your Life Speak by Parker Palmer. When things fall apart by Pembro children and Faith, but Sharon Salzburg. And I read those books and cried through every page. I have a million questions. Let me just get back to the day in February where you're walking by the pile,

which for those of us who, for anybody who, probably wasn't in New York at that time, and I remember the pile was the debris left behind by the crumpled world trade center towers. And it's molded for a long time. You said I wanted to kill myself. Now that was not a figure of speech. Correct. This was true suicidal ideation. This was I am going to jump in front of

every train. I am done. What was going on? My relationship with depression goes back to childhood. It's been a dance. This Churchill called it the black dog. The black dog would often visit me. I had been in therapy on and off from teenage years and I went back in at 30. And so at this point, it's about 38, about eight years later. And the best way I can describe it now, I think this will have some resonance with you.

So the inner me didn't match the outer me. And a prolonged state in which the inner and the outer are in conflict with one another Gizurized not only to things like that imposter syndrome voice. It says you're a piece of shit and no one's actually figured it out and Wait until they figure it out Your life is gonna fall apart Know what I'm talking about yes, I I do. Of course. Right. And the more success you have, the louder that voice gets. And so you live in this funny state where

everybody says, look at you, you did it. I remember in the months afterwards, so I, you know, I went down to Canyon Ranch and I began working on this, and it's like I think of that data as this sort of neater moment, and really climbing out from that point. And I remember it later on reading a quote attributed to Buzz Aldrin, who suffered a massive depression after becoming the second man to step on the surface of the moon. And he said something to the effect of, when you see the Earth from the vantage point of the moon, what else is there? And I remember going, fOOT! That's it.

It's like, I'd spent my 20s trying to chase, to run away from my childhood. And I spent my 30s constructing what I thought was the idea of life, for myself. And the whispering voices, just said, enough. You're done.

Can you tell me a little bit about the childhood you were trying to run away from? Sure. Mother who suffered from what's called Skitzoid Effective Disorder by Polarity by Polar. And a father was alcoholic. And alcoholic and fairly violent childhood. One of six, one of seven kids at number six. A sense year growing up in Brooklyn, being fairly regularly threatened as you walk down the street, being in the midst of this kind of urban upheaval that was going on in the 1960s and 1970s in New York. I think of myself and my family is not quite the same victims as, say, African Americans were redlining and blockbusting. Remember these terms? Redlining where you couldn't get a mortgage if you were African-American. And the negative implications of that kind of a construct

going on. But the tensions that existed led to this kind of existence where I just walked on the street and I was in fear all the time. Were you in fear in the home too? Oh sure, all the time. So it's a testament to you that you were able to become so successful in your 20s and 30s, although obviously you paid a price for it. Can you just describe a little when people said to you, hey look at you, you made it, you did it, you were successful. What were they thinking of?

What had you done that the outside world would have judged you to be such a big success? Well, I remember New York magazine did a profile in my partner at the time, Fred Wilson and I, with our first venture capital firm, Flatiron Partners. And they referred to us as princes of New York. And I remember, in fact, there was an estimate of our net worth, over individual net worth. And it was wrong, but it didn't matter. I mean, think about that.

What was the estimate? 50 million, which in real dollars now. Yeah. But it wasn't even close to that. What was the estimate? 50 million. Which in real dollars. Now. Yeah. But it wasn't even close to that. It wasn't that high. But that didn't matter. See, you live in New York. You know, we walk around and we're like looking at each other. How low should I bow to you? Well, how big is your bank account? Right. Right. Right. On my way here, we pass some of the most expensive real estate in the world. Right. What's the world in which we live in? And everybody in the outside would be like, I mean, there was this moment in 2000 when the market crashed, when the NASDAQ crashed, and the .com bubble burst.

Right? And boy, don't we wish we'd bought Amazon then, right? Or priceless, right? And as one friend put it in describing my experience, our experience, Fred and I, we went from the pinhouse to the outhouse, right? So you lost a lot of money during that period Not really we lost status And that added to the depression sure because Again, I you know as I often say, I outsourced my internal sense of self-worth to external

things. Right? A lot of us do that. A lot of us do that. Our economy depends upon you. Right, exactly. Right, drive the right car and then you'll feel good. Right? And so I outsourced it to the most seductive thing possible, fame and affirmation.

And when the worm turned, because the worm always turns, it hurt. Now what it revealed was the hollowness of a sense of self independent of all of that. In other words, if you take away the... Scaffolding. The Prince of the.com boom, the first one, there wasn't much there to Jerry himself. Well, what the fear was, what got revealed was the fuck from Brooklyn, who never really

escaped. Right, right. You thought you escaped. But we dragged you right back of course you were still by any measure rich and successful yeah but didn't feel right right right so it doesn't matter actually if you don't feel it does it matter why I know somebody unhappy successful people that's right that's right so you're at Canyon Ranch you're reading this book by Pema Chodron. Crying. Why were you crying when you read the book? Because it was so real and raw. What about it?

What about what was in the book that struck you so powerfully? That book in particular, it's the chapter called hopelessness and death. Fun reading. Fun reading, it's great to be a buddhist. And just to be clear, at this point, you were not a buddhist. No. No. I'm reading this thing and I remember her teaching about the sense of hope for a better world, being a seductive way in which we get drawn into this externalization, this outsourcing of happiness. Right?

If only, no, just feeling the blank on that sentence. If only such and such happens, I will feel better. Yeah, yeah, yeah, yeah. We're driven by these if only stuff. If only, yeah. Right? And it can be small. It's like, if only I could get to the bathroom and then I'd be able to pay attention

or if only I could get some lunch right now, then everything will be normal. I can learn how to meditate. Oh, yeah, yeah, yeah. Then those of you goes up, it scales up. All the way up to, you know, if I had enough money for a second home or if I had or more importantly if I just had more money than my neighbor or my brother-in-law whatever. Yes. If only I had enough money to create an impenetrable wall of security around me forever and ever so that nothing could ever hurt me again. If only, I remember one time sitting with my therapist laying on a couch because the psychoanalysis I'm still with

her, by the way, 24 years later. Laying on the couch, he said, at what point does it end and I'm exasperated is it as much money as Bill Gates Like what the fuck am I doing so you're reading this chapter and and all of a sudden your folly becomes clear and I'm just sitting And going oh well it was it began a process it began a process, you know, and I want to mention Parker Palmer's book as well. Because you've heard of Parker Palmer. You have to actually get Parker on the show. Parker is a brilliant quaker writer. I've actually had him on my show. The reboot podcast, which is any podcast. And he is 77, I think Parker how old you. And I consider him one of my core teachers. His first major book work was something to call the courage to teach. So he's known for his influence on education. But he's this beautiful man. Right now he's very fashionable because he has

a book called Healing the Heart of Democracy, Separate Topic. Anyway, in Let Your Life Speak, it was one of the first times I read something in which someone talked openly about their experience of being depressed. And I don't mean something like Williamster Ones, Darkness, Visible, or it felt like just another regular broken-hearted person. And it was that experience plus Pemis, plus Sharon's work, and the combination of those two. And then I go to Kenyan Ranch and I'm sitting for the first time.

They actually had you meditate there. They had me meditate and it was a simple guided visualization meditation that again I ended up in tears and I remember calling my sister Anne who had given me those books from there and Anne was always the kind of slightly weird one in the family because she would like to do things like yoga and I just remember crying her and saying, I'm so sorry, I would make fun of you. You're right. I'm a jerk. Because I would devalue any experience below the neck. You know? And I was just like treating my body like a meat bag to just carry around the real me. All those feelings, stuff them down. All that experience, all the somatic experience, stuff it down.

All of the sensory experience, ignore it. Because it was all in service to this construct of the mind and the ego. Indigo girls in, I think it's closer to fine, have a wonderful line where I think myself into a bag. I think that I'm going to somehow figure out how to get out of it. And I think what happened to me beginning that February day, and then over the next year, two years, I often think back to the Buddha and the story of the Buddha, where, you know, the story right, he grows up as a prince, he spies out the window for the first time

in old woman. He, in a flash, understands birth old age, sickness and death. He leaves his confines, he experiences the world, he becomes a student of these great teachers, but soon he outdoes them. And the way I think of him is like from Brooklyn where he just says, f**k it. It's not working. Like all of these methodologies, they're not, I'm just going to sit into this tree until I figure it out or I'll die. And that's what I feel like I was at. Like nothing worked anymore.

Not the falsity, not the personas, not money, nothing worked. And it's like my life reached up from inside my heart and grabbed me by the throw and said, are now you going to pay attention? Okay, so now if I'm myself at a juncture with another set of 1 million questions, so I have to make a decision about where I want to go. Let me stay on meditation for a second. What was it about meditation that was therapeutic for you at this rather desperate juncture

it sounds like was a combination of the practice and the theory that you were getting in the books but i'll let you the books it was the theory in the books first and um... so fast forward a year later i now have a chance to meet pema and it was a great moment. She's doing a teaching at Cooper Union,

downtown New York City, downtown New York City, and it's to raise money for a local Buddhist training center, Shambhala, New York Center. And a friend sends me a note and says, hey, I know you're interested in Pema. She's coming to town this weekend. And by this point, you're still in venture capital this morning. I'm still in venture capital, although I had made the decision to leave JP Morgan,

I didn't know what I was gonna do, but I knew that I was not renewing my contract at the end of 2002. So I literally walked away from everything and I had no job for the first time since I was 13. You were about to walk away from everything at this point. Well, by the time it's you now, you're a united, so February 20.

So at the end of 2002, I left JP Morgan. It's February 2003. I got no job. But I'm okay. I just have no identity. I have no business card. Right, right, right. So I'm going to this weekend,

and then just before they send a note to all the... Hey, there's a fundraiser on Friday night at Lou Reed in Laurie Anderson's apartment. Okay? So, hey, that's kind of cool. So I go to this place, and little did I know that it was like the cognizant of the whole Buddhist mafia in New York. It's like everybody who's anybody of cool. So I go to this place and little did I know that it was like the cognizant of the whole Buddhist mafia in New York.

It's like everybody who's had anybody was there. Like they're all walking around and all this stuff. And in walks this little nun, Pema, Ani Pema, and she tautles up to these questions. And then we all sit down like good little children and she starts teaching. She starts teaching on the nature of impermanence. All things fall apart. All the time, the fact that we're striving to maintain structure and permanence actually increases our suffering, our Dukha.

Dukha, but just as's the ancient Indian word for suffering. A word that's often, some people say suffering is a mistranslation of Dukas. Dukas could also be translated as just unsatisfactoryness. Yeah. That if you try to cling to things that will not last, you will suffer. Yeah. And for me, it evokes the suffering that we actually create ourselves. Yeah. Absolutely. It's not the suffering that we actually create ourselves.

Absolutely. It's not the suffering of a broken arm. It's the suffering of, my life is supposed to be this way. What's wrong with me that my life isn't this way? Well, and it also can be, it is often said by Buddhists that pain is inevitable, like you will break your arm at some point Suffering is option and so it's or the better the one analogy I love from the Buddhist Scripture is the analogy of the second arrow the Buddha talks about being you're walking through the woods So you get hit by an arrow and you're and that hurts like just in and of itself it hurts

But the second arrow is why am I always the guy gets hit by an arrow? Who did this to me? I'm not wrong with that. I'm not wrong with that. What did I do? It's all of that nonsense. That's the second arrow that we put in voluntarily. Right, so as it relates to impermanence,

all things fall apart all the time. All things fall apart when things fall apart, including our sense of self. So we're sitting there and we're doing exactly what's happening to me, what's happening with you and I right now, right? And this is classic, but it's teacher trick. So she's sitting there, she says, okay, so now some of you are sitting and thinking, I've got this one, I figured it out. Now you've just slipped permanent ground on the Nitha concept that itself is always falling apart. And I blurred out, that's not fair. And she looks at me, she goes, Catholic, right?

So later we have this sort of one-on-one moment and she says, you're always trying to figure out what the answer is, aren't you? You're always trying to get it right. When do you stop trying to get the A in the classroom? And I'm just like, it's like a classic, but as teacher, just like, sliced me open, takes out my organs, looks at them and goes, look at you. She tasked me on the hand and she says, honey, you think you're open. You haven't even begun to open. Just keep opening.

And to this day, now it's 14 years later. That's it. Just keep opening to the experiences as they are. So get a little granular with us about your meditation practice then and as it's changed up until now. What do you do in your mind when you're meditating or what was a technique you were taught and are you still doing it? Sounds like you entered into the Shambhala system.

I did. And did the Shambhala system. She's part of this Shambhala language. That's right. And my first teachers were from that tradition, even though I never met him, I would consider Trimper Rinpoche one of my teachers. He was her teacher. He was her teacher. Trotium Trumper Rinpoche.

Pretty controversial dude. We don't have to dive into that. Kind of a wacky dude. Yes. Yes. Absolutely. And his son, and that whole tradition, which is a powerful tradition. Today, though, I consider Sharon Salzburg, one of my teachers, on and that whole tradition, which is a powerful tradition. Today though I consider Sharon,

when Sharon Salisberg, one of my teachers who's from the Insight Meditation tradition, I consider Rochie Joan Halifax a teacher. She's from his own tradition. You are an ecumenical guy. Because wisdom traditions are powerful traditions and I will avail myself by any means necessary of alleviating suffering.

Yeah, you want to deal with that black dog with as many tools as are available. I want my allies. Yeah, no, smart. So my practice is for the most part of daily practice, although lately it's been a hard time for me to hold it. So you haven't been able to keep up the dailyness. Not in the last two or three months. Interesting. What's getting in the way?

Travel, holidays. Can't you do it on a plane? Sure, of course you can. And. But here's the difference. And this is really the point. When I sat down, I was saying this to your partner, Ben Rubin. Ben Rubin is the CEO of the 10% happier app, yes.

So when I sat down in New York for meditation instruction, the teacher gave us this guidance and we all sat for five minutes and at the end of five minutes they said, so who here in the room is driving to get an A and be a really good meditator in the room? Of course my hand went up, right? My mother got up too just so you know. Yeah but I would have been better than you. No question. No question. I am a killer meditator i have kind of released myself for them in that's amazing that is that's the game i'm working on

and it's a hard game it's been probably five six seventy years to just like oh wait wait wait wait wait wait, wait, wait, wait, wait, wait, wait, wait. The goal is not to get meditation right. The goal is not to turn meditation into yet another form of self-rerimination and self-punishment. Or self-aggrandizement. Or self-aggrandizement. Look at how proud I am, look at how good I am. The goal is to be happier

more than 10 percent, maybe even 12. Or 100 percent happy. Yeah. See today, I love the man I am and I am a freaking mess. And I can rent self-regulate. We need to put that on a quote card. That's great quote. That's going up on that's going up on my social media. Well, you know what I say? You know the whole Namaste thing right? So Namaste the God. The power to the light in you. Yes. Yeah. So the mess in me bows to the mess in you. Because there is no difference between the mess and the light. Okay, why is the Buddha called Lotus Born? You know this? No. How is a Lotus? Where are the Lotus? Yeah, the Lord is coming out of the Dung at the bottom of the earth. Out of the crap and the mock. Even the notion that the crap and the mock is something not to be loved. So I'm a mess.

There's another phrase that I like from Buddhist teachings that all the stuff that we're actually often struggling against in our meditation. It's often referred to as manure for enlightenment. Oh yeah. It's like I was struggling manure for enlightenment. Oh, yeah. It's like, I was struggling. My mom passed away in September. Oh, I'm sorry. That's recent.

Yeah. And it was a very complicated relationship. And the holiday period, which has always been a historically difficult time period, was really sharp in its poignancy. I have three adult children and they have the temerity of growing up and becoming independent adults. How dare they? And so this the pain of transition and separation and just it's life is hard. Life is hard. And I could sit in meditation and try to push all that away and, uh, mindfulness stress reduction, bullshit.

Okay, watch, watch, watch, watch, watch the biofeedback thing go to green. All right, all that's important. But, but, but, but, or I can, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, but, We are more in alignment. Whether or not I've actually put my ass on a cushion. Celebrity feuds are high stakes. You never know if you're just going to end up on Page Six or Du Moir or in court. I'm Matt Bellissi. And I'm Sydney Battle, and we're the host of Wonder E's new podcast, Dis and Tell, where each episode we unpack a different iconic celebrity feud.

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The object of my meditation is my breath. I will sit in a traditional posture, my butt raised on a cushion. I will sit anywhere from five minutes to an hour. Kind of depends on how I'm doing. I sit in the same spot. This is really important, because I'm a creature of habits. I sit in the morning, which is also really important.

The space is sacred. I actually have a room at my home in Boulder that is my meditation room, because intention is really powerful. I am going to meditate now. Okay, brain got it. And then I said, no, I will have a timer. And I have incense and I have a candle. And it creates a sense of sacredness. I'm also a former Catholic, so I like funny smells. And, you know, I like to bet in Buddhism, because I like men in funny hats.

I mean, I, right? But all of that is form. It's all, it is not the point. Right, emptiness is form, forms, and emptiness. It's from the heart sutra, for the Buddha. But, so actually making a good point, because when you were talking about incense, yeah.

All of a say, I'm, I'm, I have a strong, pronounced, perhaps undying, allergy to anything, touchy, feely, smells and bells. I'm not Catholic, grew up half Jewish, but both my parents are pretty ardent atheists. As I like to say, my mom sat me down when I was eight and told me that not only is there no Santa Claus,

but there's also no God. So that's the kind of vibe in my house. And I think a lot of folks who listen to this or like my book or whatever, they, the whole idea that you would light incense or light a candle, it's like they, they feel like they have permission to meditate because I tell them you don't have to do that stuff. You don't have to do anything. Right, but so I actually find it very interesting that, and, and a relief that I think people will too,

that you're saying doing this stuff, you know, works for you, but it's not the point. No, my God. I mean, to presume that it's the point is as much an attachment as, you ready for this, buddy? Because I'm gonna drop them. Lay it on me. As much as presuming that it's wrong to do that. Absolutely.

Neither one makes sense. They're both the dog, it's like I once had a teacher say to me, dog tied to stick. Dog runs two stick, dog still tied to stick. Dog runs away from stick, dog still tied to stick. The issue is the dog is tied to the stick. Right? It's not attachment, detachment, or revulsion, right?

Can stand candles, can stand all that form. It's too religious for me. Well, that's interesting. That's an interesting state. That's a really powerful line of inquiry when one is sitting with open mind, beginner's mind, get curious. Yeah. I mean, four squaring your camp on everything you've just said. I just have my inclination as a, I guess you could describe me. I sometimes describe myself tongue and cheek as an evangelist for, for, for, for a non-religious. No, just for meditation generally. I want

people to I think the headline for me out of all of my paragrenations through the worlds of neuroscience and meditation and Buddhism is that the mind is trainable. You're not stuck with what you got. And so in our brains are plastic. Correct. So I want people to wake up to that core fact and then what they do with that God bless. Go do it everyone. I agree with you. So but I'm thinking as to put it in business terms top of funnel. You know that the I'm going after the hardest people to reach you know and to

the skeptics. That's what I wrote my book for and that's that's my message is tuned to those people. And so I always get somewhat by proxy, nervous when people talk about incense and candles, but it is a little bit by proxy, because personally, I don't care if there's incense or candles in the room, but I'm in the tank already. It's as a evangelist that I get a little nervous, because I know that people wanna hear,

at least my folks, my tribe, wants to hear, you don't have to do that. Oh, if you use those things, if you use candles in incense, to not work with your mind, it's called spiritual bypassing. I love that term. So you can get into the candles in the incense, but you're not doing anything. You're not doing anything. You're not doing anything. Except for maybe smelling. Smelling, yeah, it's a Roman therapy. Smelling patchouli. Yeah, right.

All of that is nonsense. We can use anything to bypass the experience of being real in the moment. Anything. It's funny that you talk about being real in the moment. Now I'm just this interview is just going off the rail. We're just, I don't know, but I was doing this, I was meditating recently and I have my teacher Joseph Goldstein and who ironically has never been on the podcast. I have to fix that. But he has, I have three or four or five kind of different techniques I do

based on my work with him and. Do you do a good job with them? No, I do. I'm terrible. I'm the worst. And I was, I was kind of at the beginning of a sit. Sometimes I'll say, you know, what am I going to do now? And I said, you know what, today I'm just going to see what it's like to be me right now. And that was actually an interesting meditation, no technique. I think you gotta get lost and then,

and actually found that the moment of recrimination, because I do have it, when I get lost and wake up again, this usually tied to a whole boat load of, you know, you suck at this, you're an idiot, you're never gonna be good, blah, blah, blah. Was actually less severe when I just sat and investigated what it was like to be awake and existing.

Okay, so now I'm gonna say something really dangerous. Go for it. That's gonna go for like, it's really gonna like, like activate your high achievers side. Okay, good job. That is the most dangerous thing. I know, Nicely done. Usually.

But the truth is, what you vividly experienced is, you know, you know, this whole off-the-rails train part of the conversation began with you saying, asking me, what do I do when I meditate? Yeah. Right. What I strive to do is what you just described. Just be. Right. And if candle and incense help you get you there.

That's right. Abs. Go for it. That's right. Because, see, I don't sit on the meditation cushion so that my experience on the cushion is really cool. I sit on the cushion so that when I encounter the inevitable vagaries of day to day life,

I'm that much more resilient. That's also a great quote, by the way. Well, good for you. Good for you. I'm good. That's dangerous. Yes. Right back at you, but.

Yes. You know, I'm much more interested in resiliency than I am actually even in happiness. Yeah, because happiness is actually something that is much more fleeting And so go back to your moment So so there you are sitting in meditation and then you realize that you actually haven't quote been meditating You've been as one teacher said to me will gathering right now you have a choice in that moment. You have a choice.

And how you choose to experience that moment is whether it's gonna be just pain or suffering. Victor Frankl said, between stimulus and response is a gap and in that gap lies our choice and our freedom. How we interpret that moment. I'm sitting on the cushion. I have every intention.

Jerry said it's okay to use incense. Dan has been saying, no, you don't have to. Okay, so here I am. And I realize 20 minutes later, I have been off the rails talking about, but, but, but, but in my own head. Now you have a choice. If you want to cultivate resilience, come back to the breath, come back to the intention without judgment.

That's the tricky part. Without judgment. With loving kindness for yourself. Oh, there I did it again. Oh boy, guess I gotta sit some more. Well, I would add just one thing on top of that, which is because I've noticed that expecting the moment of waking up from distraction to be without judgment actually was a little too much for me

because actually there's a reflexive judgment in that moment of, oh, you suck at this. Yeah, or, oh, you're good at it. Oh, you're congratulations. Exactly. Great meditation. Exactly. So what I've trained myself to do sometimes is,

okay, I wake up from being distracted. Involuntarily, there's a certain, there's a self-flatulation there like you're terrible at this. Then the mindfulness kicks in. Oh, I'm judging myself. Right. Now back to the breath.

Now, imagine taking that entire experience that you just described and taking it out throughout your day. You would change your whole life. Right. I'm standing online at Starbucks. I noticed that I'm really pissed off at the person in front of me because you know when they show up

and they haven't actually figured out how they're gonna pay yet and then they get their order and like now you bring out your credit card! Okay, I got my credit card out when I'm at the door. Right. Okay, who's the crazy one now? Okay, who's contributing and feeding the wolf of my own suffering? All right?

Wake up, wake up, wake up. I have a friend who's, when he started down this path, would constantly ask the question, do you think this person is enlightened? I don't know about this. Do you think this person is enlightened? And finally one day I said,

I'll give a know about this. Do you think this person is enlightened? And finally one day I said I'll give a f**k about enlightenment. I care about not suffering. I just don't want to hurt any more. And I don't want to hurt other people because when I hurt other people I hurt. And when I hurt and when I hurt other people are hurt. I just don't want to hurt anymore. And every now and then I hurt people still. Now, I had another friend one said to me, you booted so like, you know, you sitting there on the cushion, what if everybody just sat there and said, yeah, what if everybody just said, I don't want to hurt anybody anymore? Wouldn't that be kind of cool? I do.

I do think it would be cool. Well, let me just go back to the Starbucks thing for a moment, because again, actually, this is a kind of interesting continuation of our discussion about the moment of waking up. Because I think we need to view the moment of anger at the person who doesn't know that you actually should pull your credit card out a few steps before the cashier, as not something to be angry at yourself about.

Right. To actually view that as like, I didn't order that. I didn't ask for that. It just came. So you view the curiosity with some terror, I say, use a little bit of a gooey word here, compassion. And humor. Yeah, humor. Absolutely. What could I have not yet? Yes. I am still a jerk. I've been doing this meditation thing for many, many years and I'm still a jerk. There you go.

Namaste, the mess in me. Yes. Honours the mess in me. Yes. Right. So, so now I'm going to attempt and you can, you can, there will be no hard feelings if you deflect my attempt to put the interview back on the rail slightly just because I'm curious. What is your life like now? We heard all about, you know, the, the messiness leading up to the discovery of meditation and a little bit about your meditation practice, but your life is pretty different now than it was in 2002. Yeah, so here's a vivid example of it, okay. In 2002, I weighed 250 pounds today. Really?

Yeah, he's surprised because I weighed 180. Yeah, you're a thin guy. I'm a thin man. I shed another human. That's what I wow. My I live in Boulder. I'm a coach primarily CEO coach. A CEO coach. I am called the CEO whisper. And we have a company called reboot, right? Which, so the podcast is just part of the whole set of services that we offer. But how is my life now? I still struggle to make sure that the inner and the outer or stay in alignment, I will often be caught by those who love me in those moments where

it's not. And shame will arise. And I can usually find my balance again and regulate. Even in hard times, you know, this past holiday season, someone, I was talking to someone and I said, well, what's going on for you?" And I said, I'm grieving. And they said, well, what, your mom? I said, time passing. It hurts.

And then the solstice pass, which was the anniversary of my father's passing, my father passed 24 years ago. And then Christmas and the nears. And the image I often think of is there's a story I heard when I was a boy that you know why birds sing in the morning. Because at night when the sun goes down they think that's it life is over. And they start to sing because hey it's the sun! It's come back! So January 1, sun came back. And I sit down and I talk to a client and I break out of my narcissistic bubble momentarily

and I am compassionate or empathetically there with someone who sits down across from me and they're 30 years old and they're overwhelmed and they're, they think they suck and they're overwhelmed, and they're, they think they suck, and they think that those voices in their head, and I say, I get you, I understand. And I haven't fixed anything, but they walk away feeling a little bit lighter. And so, I think today, I'm the luckiest human being on the face of the damn planet. Because I get to have conversations like that all day long.

How does your Buddhist practice impact your CEO whispering and in every way imaginable? Are there some because you are, I'm interested in how it goes down because you are unabashedly and I think in a cool way, a little wee gooey, you know, you light incense and you talk about the heart, things that I don't yet do. How does that go down with the CEO crowd? Because I would imagine some of these guys and women are pretty hard charging. So one of the things we do is we do something called a bootcamp.

And actually Sharon came to our last bootcamp. And this is a four or five day multi day experience and it's a immersive experience. And it was originally designed for CEOs and we expanded the co-founders. And then we introduced investor boot camps, VC boot camps. Our next VC boot camp is actually next week. We originally designed it for slots of 12 people. We have 24 people coming. 24 theoretically powerful people, they're not coming to hear quote Jerry to teach the Dharma. That's not what I'm there for. But what I try to do is I combine three

That's not what I'm there for. But what I try to do is I combine three overlapping circles. One is pragmatic, practical experience in this whole realm of our relationship to work. Like, what's that like? What's it like to be a CEO? What's it like to be an investor? What's it like to be a board member, for example, and feel incredibly responsible for this organization, but be the least informed person in the room? Try to manage your anxiety there. Yeah.

They're interesting because the board member isn't an interesting position. You are the least informed person in the room. The least informed person in the room, but you've only got four or five million dollars riding on this one and your entire reputation. Good luck. Try not to be aggressive, right? Then the psychological piece of that, what does that really mean? We've been focused on meditation, mindfulness, and spirituality because of your podcast,

but that's just a part of the larger picture. When I show up, I'm trying to bring all three of those realms in. I don't just show up and say meditate. In fact, most of my clients don't meditate. And I don't really care if they meditate. What I do care is, are you awake to the ways in which you're being complicit in creating the conditions you say you don't want? Are you creating... Here's a perfect example. A guy comes to our bootcamp last year. First night, he's like,

oh, Jerry, you're reading poetry. What does this have to do with any, I got a problem. My problem is my VP of sales is a greedy SOB. He's like, okay, that's interesting. All right, two days later, we're exploring what's known as the shadow qualities, Carl Jungin shadow qualities, the parts of ourselves that are denied, the ways in which we pretend we're not this or that, because there are things that are not acceptable.

This guy, and the campers are struggling, what to get this concept. And I said, well, look at the things you're ashamed of. And this guy breaks down and he starts crying. And he starts talking about his addiction to alcohol and how he ended up spending years living under an overpass. And while he was living under the overpass, he saw he would never, ever be without money again. Do you hear the greed?

And I turned to him and I said, who hired the greedy head of sales? Right? You don't like the organization because it's violent and greedy. You have to actually welcome in the mess of your own fear which you tried to push away by making a bargain with yourself.

Now is that Dharma? Damn right. It's two by four upside your skull, Dharma. It's okay, you're going to sit in the cushion? Great. Let's get real. Let's look at what you're really doing in your day to day life. Right? You want to lower your blood pressure? Be my guest. You want to create neuroplasticity in your brain. Fantastic. You wanna break your addiction to this or your God bless.

But what's the real source of suffering? Break through the delusion. We use a term in my company, radical self inquiry. Now you combine that with the Buddhist concept of radical self-acceptance. Now you're onto something. Yep, yeah, I mean, you hard to fix your problems if you can't see them clearly.

So that's the first step. Especially if you're the one who's hiding those problems. Right, right, exactly. And if you're at the head of an organization, then that pathology spread, metastasizes throughout the whole thing. Throughout the interrogation. Which may answer a question that arose for me as I was listening to your podcast, which

is this is big focus on the sort of well-being of CEOs. And I was thinking for you, Jerry, as a Buddhist, do you ever think to yourself, like, why am I focusing on this very small kind of affluent community of people to treat, as opposed to, like, aren't you more worried about the well-being of, I don't know, intercity children? One time I had the tea with Anipama children, and I went to her and I said, I was being invited to sit on the board of directors

of a meditation or retreat center. And I said, oh, Anipama, I don't wanna be on the board of directors I want to sit in the back of the classroom and all this stuff. And she went, yeah, bullshit. And I said, excuse me. I said, no, no, you don't understand. I'm not like, the ego grand, she goes, that's just your ego. Okay.

Your karma is to combine these worlds. When you pull away from your karma, you're not going to get happier. When you lean into your karma, so to go back to your question from moment, my karma created this very strange character who has this deep experience in the technology, venture back startup world, and the psychological experience that I had and the spirituality that I have. That's my karma. Now do I care?

Of course I care. I can't read a newspaper without crying. I mean, there are children suffering everywhere, and I grew up in violence. It breaks my heart, and I am proud that I cry. But that's not my karma. Now, I'll tell you, tactically, if I can make this particular CEO, if I can help that person feel marginally better, and they go home to her husband, and they are not in aggression there.

And then those children are sitting at the table. And mom, the startup CEO is a lot less stressed. And then their work environment is a lot less stressful. And then they each go home to their children. Isn't that important work? Yeah, I do think so. Which is why in some ways when I asked the question, I made reference to the fact that what you had said,

what we had been discussing just prior to my asking the question, may have answered the question, which is, these people are at the head of organizations, and their pathologies can spread throughout those organizations, and that can have knock on effects that are profound. And if you can go right to the top and make those people healthier, then actually you're having a big effect in the world.

But it was just a question that arose for me as I was listening to your to the podcast. And it says nothing about what you're doing, what you may be doing outside of your professional work. Right. So it's just an interesting, just an interesting idea. But I will say, I will say that I've observed the venture world, but I've never been in the business.

I've been an employee of major corporations. My whole I've worked here at ABC News for 17 years. So I'm a Disney cast member. So but now I'm a co-founder with the aforementioned Ben Rubin of this app company. And so the start of world is crazy. It's nuts. You're just always on the cusp of death. Yes, it's raw, it's primal, it's actually a great place to work with these sorts of issues because it's, it's, there's no place to hide. You can't hide. The experience is visceral and it's literally moment to moment, moment to moment. I mean, I did a podcast conversation with Ben prior to 10% happier in the previous incarnation, I think it was called Change Collective. And we talked about his experience then of his previous company collapsing and his fear of that company collapsing.

Now, you've been a practitioner and hanging around with with the mindfulness mafia for a while now. Can you see the application of this, right? Do you know, are you familiar with the notion of a charnel ground practice? Yes, yes, we stare at decomposing bodies. Right. And meditate while looking at it. Right, right. Now the point of staring at decomposing bodies

isn't to experience decomposition. The point is to go to the place that most scares you where your experience of life is so visceral and raw. Well, being the CEO of a startup is like a charnel ground practice. So I love hanging out with entrepreneurs because they're right on that edge. As a guy who likes bowing to the mess and other people, you got a lot to back. Well, I think our listeners will have gotten just a brief sense

of of your wizardry in this conversation. If people want to learn more about you, how and where can I do so? The best site is reboot.io, not.com.io, which of course stands for Indian Ocean, but it's kind of cool. Reboot.io, we've got a podcast. We also do these things called five day reboots,

which are free, and they're guided practices. They're not meditation practices, but hey, read this. Hey, listen to this. Hey, do this. We do peer support groups. We do my goals to make the conversation about our relationship, our existential relationship with work accessible to anybody. So that's what they can do. It's good to that site in Czechoslovakia. Sometimes I use an expression when we get a particularly good guest, which is that they came to play.

Like, you just went right for the raw stuff, so I appreciate it. Well, thank you. I mean, funny little story. I was doing a talk in Denver a few months ago with my friend Brad Feld and I'm standing online getting iced tea and this guy comes up to me and he you know we're both online and he's like, you know, right on line and I said I'm wearing my name tag right and I said, you know, I think this guy Jerry called on his full shit and he looks at me and he looks at me and he looks laugh because wait you're just like you are on the podcast And I said that's it the inner and the outer exactly match

So well great to see your inner and outer thank you sir. Thank you Okay, there's another edition of the 10% happier podcast if you liked it Please make sure to subscribe rate us and if you want to suggest topics We should cover or guess we should bring in hit me up on Twitter at Dan B Harris I also want to thank Hardly the people who produced this podcast and really do pretty much all the work Lauren F. Ron Josh Cohan Sarah Amos Andrew Calves Steve Jones and the head of ABC News Digital Dance Silver. I'll talk to you next Wednesday. Hey, hey, prime members. You can listen to 10% happier early and add free on Amazon Music. Download the Amazon Music app today.

Or you can listen early and add free with Wondery Plus in Apple Podcasts. Before you go, do us a solid and tell us all about yourself by completing a short survey at Wondery.com slash survey.