The School of Greatness - Building Wealth, Overcoming Failure & Rethinking Risk Taking w/ Sukhinder Singh Cassidy EP 1150

Episode Date: August 16, 2021

Today's guest is Sukhinder Singh Cassidy. For more than 25 years, she’s been a leading tech entrepreneur and CEO who’s grown, scaled, and advised for companies like StubHub, Google, Amazon, and more. She’s currently the Founder and Chairman of theBoardlist, a talent marketplace focused on putting diverse leaders into key executive positions -- and also serves on the board of directors at Urban Outfitters and Upstart.She just wrote a new book called, Choose Possibility: Take Risks and Thrive (Even When You Fail), where she shares the most valuable lessons she’s learned over her years of experience in leadership roles at some of Silicon Valley’s most well-known companies.In this episode Lewis and Sukhinder discuss the life-changing lessons Sukhinder learned from her father, why most businesses fail and how to make sure your business isn’t one of them, why we all need to change our mindset around failure & risk taking, and what to do instead, the best ways to start building wealth today, what Sukhinder considers the most rewarding experiences she’s had over the course of her career, and so much more!For more go to: www.lewishowes.com/1150Check out The Boardlist: site.theboardlist.comThe Wim Hof Experience: Mindset Training, Power Breathing, and Brotherhood: https://link.chtbl.com/910-podA Scientific Guide to Living Longer, Feeling Happier & Eating Healthier with Dr. Rhonda Patrick: https://link.chtbl.com/967-podThe Science of Sleep for Ultimate Success with Shawn Stevenson: https://link.chtbl.com/896-pod 

This is episode number 1150 with Sukhinder Singh Cassidy. Welcome to the School of Greatness. My name is Lewis Howes, former pro athlete turned lifestyle entrepreneur. And each week we bring you an inspiring person or message to help you discover how to unlock your inner greatness. Thanks for spending some time with me today. Now let the class begin. T.S. Eliot said,

only those who will risk going too far can possibly find out how far one can go. And Jim Rohn said, it doesn't matter which side of the fence you get off on sometimes. What matters most is getting off. You cannot make progress without making decisions. My guest today is Sukinder Singh Cassidy, and for more than 25 years, she's been a leading

tech entrepreneur and CEO who's grown, scaled, and advised for companies like StubHub, Google, Amazon, and more. And she's currently the founder and chairman of The Board List, a talent marketplace focused on putting diverse leaders into key executive positions and also serves on the board of directors at Urban Outfitters and Upstart. And she just wrote a new book called Choose Possibility, Take Risks and Thrive Even When You Fail, where she shares the most valuable lessons she's learned over her years of experience in leadership roles at some of Silicon Valley's most well-known companies. And her insight when it comes to business and life is something I hope you find as much value in as I did. And it was a real treat getting to speak with her and I'm already looking forward to connecting with her again soon. And in this episode, we discuss the life-changing lessons she learned from her father, why most businesses fail and how to make sure your business isn't one of them, why we all need to change our mindset around failure and risk-taking and what

to do instead, the best ways to start building wealth today, what Sue Kinder considers the most rewarding experiences she's had over the course of her career and so much more. Again, I'm so excited about this and if you're enjoying this, make sure to share this with someone that you think would be inspired as well. And a quick reminder to subscribe to the School of Greatness, as well as giving us a rating and review. And I wanted to take a quick moment

to share one of my favorite reviews from last week. And this is from Michael, who's from the Philippines, who says, I just wanted to take a moment and say, thank you so much for creating an impactful podcast. I believe that we all have a voice that deserves to be heard. Thank you for putting this into the world. And this is from Andrea, who's from Croatia. And she says, love listening to this podcast.

Whenever I listen to an episode, it's like you're talking to me. And even though you don't see your listeners, you talk to them individually. So thank you for inspiring me to do great things. So big shout out to those fans of the week. And again, if you want to leave a review and have a chance to be shouted out on the podcast, make sure to go to Apple Podcasts right now and leave a review. Okay, in just a moment, the one and only Sukhinder Singh Cassidy. What would make this the most powerful interview you've ever done?

That's a really hard question. I'm thinking about the answer and very rarely do I say don't have an answer. I could say candor, we're going to have candor. I could say engagement, we're going to have engagement. I'm trying to think about like what message, maybe the most powerful thing would be like the whole reason I wrote the book is not for money, right? It's to land the idea that people have just a total misconception about how risk and reward work. So like maybe if you and I landed an interview that sort of brings that home, that kind of singular message and people take it, maybe.

I don't know. It's a really high bar. You've done 1,100 plus interviews. What would make this a home run for you? Let's ask that question. It's probably the same challenge. hundred plus interviews what would make this a home run for you let's ask probably the same challenge uh that we we go deep on things that maybe uh we wouldn't actually go deep on that we get vulnerable that we reveal things both of us that that connect to people's hearts okay that

would get out of our heads awesome and tap into the soul okay um If you want to tap into the soul, you have to ask me about my father. Okay. Yeah, yeah. If you want to go like straight there. I'm watching stuff about your dad. Yeah, yeah. It's fascinating.

Because I think like the book is a business book that has an undercurrent of how I was raised. But if you flipped it, I would say like Sea of the Soul is more my book.

I just had Gary. Gary Zukav, I know. Yeah, yeah. So if you think about the messages in Sea of the Soul, I remember I went to an event that Sheryl Sandberg hosted with Oprah at our house back in the Valley Winter. She used to do these events that were like 25 women and Oprah came. And Oprah was talking about Gary Zukav's book. And that was the first time I heard of it.

You know, she was talking. And so I read See the Soul. And I just remember reading it. I was like, wow, like this book book, this is the way I was raised. So if you want to talk about soulful stuff, that's the stuff I talk about with my coach and my- That's what's going to move my audience. The analytical, heady stuff, they're going to be, they don't come here for that.

Then let's talk about the soulful stuff, how you live your life. Because I am totally down for that conversation. So if you said, what's the deepest we can get the deepest we can get is like why are we all here what are the experiences you have that like convince you that there's something more like okay or something like and for me just to be clear now you're gonna get me terry like i fundamentally believe that the reason i'm on like the way i'm going to express all my gifts or impact on the world is through business a hundred percent yeah a hundred percent. And my father definitely saw that in me.

He was like, that will be the way. And he was the most religious, spiritual person I know. And also impactful and also the most entrepreneurial. So like I just look at it. I'm like, yeah, yeah, that's the standard. So if you read my book, you'd be like, I don't like that. I don't like to be like, oh, my, you know, my hero is richard branson like of course like of course i admire all these you know but i'm like no here's my dad like his life and his purpose and his vocation and his impact with

all the exact same thing wow right completely integrated that's cool aligned aligned completely integrated and aligned that's cool yeah which is not a conversation i have with most people i have it with my coach i have it with people. I have it with my coach. I have it with my priest. I have it with my mom. My mom read the book, and she said, because I hadn't told her I wrote the book. I was like, you know what? I need to tell her.

And then she's like, what are you so busy with? I was like, Mom, I'm writing a book. I wrote a book, and I want to give it to her for Mother's Day. So I gave it to her. And she called me yesterday. And she's like, I finished the book. I was like, great. What do you think? And then she started sobbing. And she's like, I finished the book. I was like, great. What did you think?

And then she started sobbing. And she said, I read the acknowledgments. I'm like, well, hopefully you feel acknowledged. And she said, but I also read the last chapter in the book, which is all about your father. And she just was like bawling her eyes out. And she's like, you never talk about this stuff. But she's like, I read it and I think like, sorry, you're going to get me teary. I read it and I think like, you can get me teary i read i think like

you must think about him all the time i'm like all the time wow and she said and she said she said and then she was crying she's like you know he was loved my life i told you he was a special person and the whole world saw him as a special person i was like yeah of course i'm like that last chapter is exactly what i believe and i think about my dad all the time and she said and she said like she's just like and she she's just like, and she's like, like, it was beautiful. She's like, but I, it just made me remember how much I miss him. And that's right. Anyway, so like, you want to get deep? That'll be deep. When you think about your dad, what do you think about? I think about the integration, as we talked about. I think about, and I write about it in the book. I think about

the fact that like, most people move through this world, including all the people you and I know, and they really think that power is to be harnessed, right? Like power is to be harnessed. And my dad, my dad, like he just gave, like I call the concept in the book power flow. Most people like dream of being powerful. I'm like, my father was the most powerful person I know. I'm like, but it's because he had power flow. He was like this abundant source of energy, right? So you bring it like, he could just give energy away to people. You know what I mean? He never said I, ever. Like I say I all the time. He just never said I. What do you say? He would just be like, well, what do you want? Like, I just don't know how to describe it. He talked about like, he just helped people connect with their purpose and he

made them feel really good. And you know those people who are like when you're with them they make you they're so present that they make you feel like your their time with you is like a gift to you so my father was that person right you could have a conversation and there was nobody who didn't leave a conversation with him just totally energized like a hundred percent nobody would feel bad about themselves they just left people say to me like oh my god you like have so much energy, you make me feel anxious or nervous or whatever. My dad just made everybody feel more full of themselves. That was his gift. And so I call that power flow. Once you understand that energy that you have is to be given away, because you know it's pretty abundant. If you can generate it for yourself, you can just keep

giving energy to other people. So that was. Right? So that was his gift. Power flow. I call it power flow, not powerful. Interesting. Yeah, I'm like, so why you all want to harness power? People think you're powerful. I'm like, people would say my dad was the most powerful person they knew. He could give a f*** about holding power.

Right. I don't even think he would think about it that way. I'd just be like, you know, just keep flowing from him. And the more that flow from him, the more that would like, yeah, amass to him, right? But he didn't care about being powerful. I'm just saying that was his impact, right? If you can make other people impactful, like think about that gift. What was the, or the three biggest lessons he taught you growing up?

Possibilities in small acts as well as big acts. Possibilities in small acts. As well as big acts. We tend to small acts? As well as big acts. We tend to think of like risk-taking and possibility as like, if you can't do something big, don't do it at all, right? But what if possibility is like, you know, and I'm for sure he was an entrepreneur. So I think that you would say possibilities in little acts. Like it might be in doing your taxes.

It might be in, you know, trying to come up with a creative name for your medical practice, which he did. It might be like helping your daughter build like, you know, a working model of the human eye in the second grade, which he did with me. So I just felt like he was always striving for possibility in little and big things. So like possibility had all these dimensions, little and big, little, big, little, big. Yeah. As opposed to like waiting for one big act, right? That was one big lesson. Yeah, one big lesson.

Like number two, probably, that we're all meant to express some sort of, like you're here to give purpose and service to other people, right? So he wouldn't have said like, what does that need to be? You know, he just like exemplified it. I don't know how to-

It's his way of being. It's his way of being. Like when somebody- He didn't say it, he just wasn't. Yeah, he just wasn't. Like, you know, there's like conversations about these things, right? It's just like you see this living embod way of being. He didn't say it, he just wasn't. Yeah, he just wasn't. Like, you know, there's like conversations about these things, right? It's just like you see this living embodiment of it.

So I'd say that his second lesson was probably about just like you're here to be of service and to have impact, right? So I think that's probably second lesson. Maybe the third. Yeah, maybe the third is something much more simple. I mean, my parents just told me that like you think it's all about you, you're totally mistaken. It's not quite destiny, but you live in a universe that's far more powerful than you. You think you're in control of everything, you're in control of nothing. It's weird because you can say, how can you live with somebody who says, well, the whole

universe is moving around you. If you think it's all about you, you're wildly mistaken. So my dad had this way of understanding that like, we're small in a very big universe, yet still making you feel empowered, right? So that's an interesting lesson. You're insignificant, but you're significant. Yes, you're insignificant, but everything is possible.

You understand? And so I understand both those things. I'm like, I can both say like, hey, I feel completely empowered, yet I realize like, if I think this act is all about me, like, that's a totally ridiculous thing. So that's why I feel like, I mean, I love leaders like that, right? They're very confident, and yet they're very humble. Yes.

And my father was that. Like, he was, like, the most confident, like, grounded in himself person I could ever imagine, yet complete humility. Right. Because he's just like, yeah, I'm a speck on the back of a universe for a period of time. Yet, while you're here, do something useful. So both can be true, right? You can both be insignificant, yet while you're here,

you're meant to do something totally, totally significant. Is there a conversation that you really repeat in your mind over and over that he either shared with you, whether it was an intentional conversation or something he said, you know, off the cuff that really resonates and sticks with you still? No, it's interesting. I honestly can say it's not a single conversation because, like I said, like there were no lectures at our table.

You know, it was like my dad was like, you must do this or whatever. Like he would say it constantly, and i think i'm very guilty of this so he would literally say like why you ever begin sentences with it like i like you know what i mean like he wouldn't say that he wasn't scolding me he was just like this just reminder that like i do it all the time we do it like i am so you know i mean but he's like he just kind of had the absence of ego so no i honestly there was no big talk conversation it was just no like seminal moment where he sat me down and told me these things it was just like it's just like like just watching him be but like there's a story in the book that i tell that um is very emblematic of my father this is

what i mean when i say small acts of possibility for other people, right? So my dad was a doctor. He loved being a doctor. What type of doctor? He was a general practitioner. But he also loved being an entrepreneur. Like, he loved both. And we had, and he grew up in Africa and immigrated to Canada late in his life.

And so one of his dear friends passed away, but his son was like my age, like a teenager, and came to stay with us for like one summer. He lived in England and came to stay with us. So we get, you know, family friend's son comes to stay with us, we become close to him, this kid Bobby. And Bobby went on and became a surgeon. And my-

Your dad's son or your dad's friend's son? My dad's friend's son. Just friend of family, you know, so I got to know Bobby. And my dad's son or your dad's friend's son? My dad's friend's son. Just friend of family, you know, so I got to know Bobby. And my dad's funeral, you can probably tell my dad was pretty religious. So the church we follow, believe it or not, is in England. So multiple times a year we would go to England. Really? Yeah, and literally live in the church and do service like twice a year.

So like when other people went to Disneyland, I mean like literally Christmas vacation. You were there for a year. So like when other people went to Disneyland, I mean like literally Christmas vacation. You were there for a week. And summer, we would go to England, live at this church, because my dad was like not atheist, but agnostic, but then he had this like spiritual awakening in his early 40s.

So he didn't follow a specific religion, but he followed. No, we're Sikh. He was curious about all religions and believed generally in God. Yeah. But like, I mean, this is why I'm like getting way deep here. So maybe you want, like, I mean, this is why I'm, like, getting way deep here.

So maybe you want to tell me. No, this is great. This is fascinating. So he was interested in all religions. Interested in all religions, but Sikh. Like, you know, I'm Sikh. You know, turbans, what have you. But I think sometime in his early 40s, before I was born, met a man who he became his physician, who was the head of a Sikh church.

And he literally thought he met the embodiment of God. So like overnight, my mom says like he came home and he was a changed man. He stopped drinking. He stopped gambling. He became like, he got baptized in the Sikh religion. And he began following this person. Before he wasn't Sikh though. He was Sikh, but he wasn't Orthodox.

He wasn't all in. Yeah, he wasn't all in. Like he was turban, he was cultural. He was Sikh. But you know, like loosely Sikh. He didn't want to get baptized. It's like becoming the equivalent of like, you're Jewish and then you're Orthodox. Right.

So he was generally interested in religion and curious about the world and all those things. But then he literally met a man who changed his life. And so he became his physician. He started following him. My mom was like, overnight, he just became uninterested in all sorts of material things and became much more spiritual. What do you think that was? That he saw or witnessed or that he said to him that just woke him up?

He literally said he felt like he was a saintly person. He literally said, I feel like I met a saint. Wow. And so that saint founded a specific Sikh church. There's Sikhs all over the world. And in England.

He moved from Africa to England. And he has a church that has thousands of people. So my dad subscribed to that church. So we all did. We still do. And so anyway, my point overall is that you said sort of, so we all subscribed to this church. Bobby's dad was at this church. So my dad literally passed away in an airport in England because he had a heart attack. Oh, man. Bobby's dad was, you know, at this church. So my dad literally passed away in an

airport in England because he had a heart attack. Oh, man. It's okay. It's okay. It was 20 years ago. 20 years ago. Yeah. Like I said, he would go to the church two times a year, right? So even after we grew up, my dad and my mom- Was this on the way to the church? No, he was at the church. The church had rented a plane at Heathrow Airport. Not rented a plane. They were all on the same plane flying to Kenya and Africa to do service. To do service. Literally, our church does service in India and Africa. So they were all flying to Africa together. And my dad and my mom were going. And I was in my 20s. And my dad was in the airport and he had a heart attack. Because he was just trying to get to the gate too fast. And he passed. And he passed away at Heathrow. Oh man. And passed away like in the airport.

Anyway, but the benefit of that whole thing is my dad was in England at the church that he loved when he passed. Wow. So we flew there for the funeral. Oh wow. So at his funeral, Bobby, who I saw after many years. The saint. No, Bobby, the son, the son of a friend. The saint is like, the saint had long passed and you know, successor saints run the church. Bobby, the son of a friend. The saint had long passed, and successor saints run the church. Bobby, the son of my dad's good friend, who became a surgeon, who had come to visit us. So I knew Bobby. We're in our teens. He comes, hangs out. I go on and have my grown-up life. Bobby has his grown-up life, but my dad sees Bobby all the time because he visits England twice a year, and Bobby's at the same church. he knows Bobby's story Bobby goes on to medical school becomes a

surgeon what have you anyway I see Bobby at my dad's funeral he's like did I ever tell you this story about my your dad I was like what story Bobby no he didn't he's like he's like you know well you remember I visited you in Canada and then I was thinking about what to do with my career and I was thinking about you know becoming a doctor and becoming a surgeon and so I sought out your dad one year when he was like visiting the church in England. I was like, what do you think? And he said, he said, you know what your dad did for me? I was like, no, what did he do? He's like, he took both my hands.

He turned them up and down. He looked at me. He's like, and he just like said to me with this like big, deep smile. He's like, Bobby, these are, these are the hands of a surgeon. You know, and like, like, like just on me, like a little lack, like nothing to him. Bobby's like, I always remember it. Cause he he, like he looked me in the eye and he gave me this big smile and he's like, Bobby, and he turned my hands over and he's like, these are the hands of a surgeon.

He's like, and then I went to medical school and I became a surgeon. And he's like, he's like, I always remember that point with your dad. Wow, that's beautiful. That was my dad. So like, you know, it's no like, it's no like sit down, big lecture, like just lots of conversations and like gems like this everywhere. So like, clearly like something for Bobby triggered, right? sit down, big lecture, like just lots of conversations and like gems like this everywhere. So like clearly like something for Bobby triggered, right?

He's like, oh, like he just told me I should go become a surgeon or like he gave me a blessing or something. Wow, that's beautiful. Dude, what are we doing? Like we're supposed to talk about the book. This is the book. It is. It is. But it is the undertone of the book.

Of course. Like this book is like the business. This is what's made you who you are. Yeah. It's part of you. But this book is the business. It is. It is. But it is the undertone of the book. Of course. Like this book is like the business. This is what's made you who you are. Yeah. It's part of you. This book is the business manifestation. Yeah. I'm fascinated by your story. And obviously the story of your father has made a massive impact on who you've become

as a human being. And it seems like without his presence and his being, you wouldn't be the successful person you are. You wouldn't be the caring mother, partner, executive, all these things that's driven you here. No. And look, I appreciate you're getting to the heart of it. But the reality is, as we discussed, the reality is just that I think if we can come to a place in our lives where what we do and who we are integrated,

that's the highest. That's authentic power. That's authentic power. It's what we talked about. And so whenever people ask me about these lessons, they're so intertwined. Yes. Yeah. I mean, I know that most people, I see a lot of people who think about what I do is different from who I am.

And I have a very hard time separating the two, obviously. As you can tell. Explain that more. Like your job is not who you are. Yes, your job is not who you are, right? So if you think about like you spend, and by the way, I'm not saying like have a job with like that leaves you with like no perspective on, you know, what's important in your life, right? But I'm saying that who you are at work and how you express your gift is as important. Think about spending 10, 12 hours a day at something, finding a passion at work that expresses who you are. And as I keep coming back to your unique gift and strength for impact,

yeah, I think that's very purposeful. And I think a lot of people think like, oh, there's my day job and how I make money. And then there's what I care about. And I'm like, well, my's my day job and how I make money. And then there's, you know, what I care about. And I'm like, well, my example, my lifetime, not just my dad, by the way. We give him a lot of credit, but my mom. She was a doctor as well. She didn't love entrepreneurship the way my dad did, but she loved serving people.

I'm like, why can't they be integrated? Why shouldn't they be integrated? Right. So, yeah. So, obviously, I'm somebody who takes work too personally. Well, I think other people maybe have more distance from it, but I think it's all a reflection of how I grew up. Well, this is my job and then I come home and I live my authentic life.

Yes, exactly. But what if you could live your authentic life all the time? All the time. And by the way, we all, look, look. And there's going to be things you don't enjoy doing about your work or your job. Yeah, absolutely. Just like everyone. But if you could be yourself and use most of your gifts in that

role, that's powerful. It would be great, right? Yeah. And of course, and you know, we live in an era where most people want to go to work and feel even more so than ever that who they are is welcome and that they are included and what their values are fit. And I want the same thing. But this is not to suggest, by the way, I live some perfectly integrated life. I'm like, this is making, you know, this has a risk of people thinking that I'm really good at this. What I would say is this is my, to your point, this is my intention and this is my worldview. So, as I said, I'm pretty convinced that the way I'm meant to express my gifts is through business. And that that's totally okay and more than okay.

Yes. How do you express your gifts in business? Well, I think you do it a few, I think okay. Yes. How do you express your gifts in business? Well, I think you do it a few, I think. How do you personally do it? How do I personally do it? Like when you're leading a company, how are you expressing your gifts? Well, two things. I try and bring three things to any situation in business. Number one, I wake up most days feeling pretty grateful for the amazingly talented people I get to work with. Yes, your team. And so I guess whatever, when I'm at work as CEO, I think of like both leverage and my gift is making other people able to be even more successful and think of themselves

and accelerate their journey. Yes. Right? So I think I have that gift because I don't think I wake up every day thinking I'm the best person in the room. I think I wake up every day going like, wow, these are really talented people. And so what I know I can do for people is give them energy and excitement and passion and help them maybe drive faster than they thought they could go. So I think that's

one of my unique gifts. That's great. Number two, again, not that I think I'm so smart, but I love consuming information. I like thinking fast and acting fast. And so I like to think that, you know, maybe a conversation, you know, with me is one where people learn faster and where I learn faster. Like that's a very, so it's not just my gift, right? It's what I enjoy. So I love interactions where you and I, like we have this interaction, we both leave and it's like a super rewarding interaction, right? I consume a lot of information. I can give you insight. You can give me insight. And off we both go. And so I think I'm pretty good at consuming information and helping people give insight and gain insight by just asking lots of questions. So I think I process information. That's a gift, I think. But it's a gift to be used,

right, to help accelerate outcomes for people and for businesses right um those are probably the two big ones just processing power and you know passion energy ability to get people excited um and make them realize that they're capable of more what are the three most interesting questions you think we should be asking other human beings whether it be whether it be in business or life in general what do you think are three most fascinating questions? Yeah. I think these are, well, I think the questions to ask yourself, first and foremost, I think everybody should ask themselves, what are my unique gifts? As we talked about, I think that these, this is a question I would ask you, but it's a question I

think you should ask yourself, right? What are my unique gifts? Because I think that when we can articulate what those are, it's not like we're full of ourselves in a bad way. We understand how maybe we can have the most impact. And we seek out environments where that impact can be kind of known, seen, practiced, and realized. So I think that is the number one question people should ask themselves is, you know, what are my most authentic gifts? Number two, and of course, I know about others, I feel like I also, I believe people should deeply know what they're not great at. And not just like what are my unique vulnerabilities, not in like the areas I have, like that will always be my work to improve. Like this is what I would point.

Like I sound like, like I'm sitting on some pedestal. I'm not. I can tell you. Like my kids, I drive them crazy. Like all of these same things that are gifts, as you know, have an edge to them that are pretty brutal, right? My kids would be like, Mom. What are your unique vulnerabilities? Well, they all are the downsides of my edges, right?

I would wish that like my father, I could make people feel, I know I can make people feel energized, but that same energy makes people feel pretty nervous, right? It has a dark side where it's like people can feel like, well, am I not enough? Like, what do I do to keep up with Sukhinder? Like, that's not really the point, right? I'm not here to make you feel less of yourself. Right. I'm here, like, so I speed people up. Do you know what I mean?

Like, you start talking, I start talking, people are going faster and faster. So I'm here like so I speed people up do you know what I mean like you start talking I start talking people are going faster faster so I'm pretty impatient so like if you have high energy and it's always trying to be deployed you're pretty impatient right you may not wait for someone to finish their sentence you make some make somebody else feel nervous so like that will always be my work right and that is the downside of being like a highly energized person like controlling that energy and that passion, right? So it's always at its most productive edge. That is it by a mile. That is like, that will be my work.

And I have lots of other vulnerabilities, but, and lots of like, well, you and I both agree, vulnerability is a good word. So I hate using that word. I have lots of other areas for development. Areas for growth. Areas for growth, like tons, like tons, right? But I would say like what I'm aware of in myself is that one vein sprouts so many, you know. Sure. It's like the root of a lot of evils, right?

So that's probably my biggest by far. Okay. And then the third question we should all be asking. The third question I would say that people should ask themselves. I think it's maybe not a question you ask once. It's a question you ask several. It's a question you ask several. It's a question you ask many, many times, which is what's possible now? In just any area of life.

In any area. If you stopped and said, like, what's possible now that I'm not doing? Because I think that people, remember when we started this conversation, I said people think the possibility is in big acts. Right. And I think possibility is in small acts. So if I see it, it's like, what's possible today? Maybe that's the question. What's possible today? If I wanted to find more joy in a certain area, if I want to find more joy at work,

what's possible today? And by the way, again, make no mistake, it's not like I'm perfect at this practice, right? I'm sure there's lots of things I should do. And I'm like, oh, what's possible at home that I'm not doing today? But I do think that, you know, there's a lot of power in small acts. Yeah. And starting now, right, and to your point, getting in that imperfect motion, right, versus waiting for the day where every possibility will be perfect. That day never comes. Never, yeah.

It never comes. So I think, like, if you ask yourself what's possible today, you probably unlock something today, right? And I'm not saying any of us are going to be able to unlock it. Like I live no perfect day where I unlock all the possibilities in my life. But, yeah, I do know, you know, I do know the power that comes from unlocking even one possibility. Right. Right.

That sounds like, well, that's a lesson your dad, you said from your dad as well. Small and big possibilities. Yeah. When do you feel the most loved? When do I feel the most loved loved when you're doing or receiving what it's a yeah we all feel I guess love differently well first and foremost for me I feel the most loved when I feel accepted for who I am gosh I was having this conversation this morning with someone you were literally an hour ago was like, I'm so grateful and appreciative to be

around people that fully accept me for who I am. Don't judge me. Don't try to change me. Yeah. But accept my authentic power. Yes, that's totally right. And I would say I feel like I feel completely loved when people accept me for who I am, including my imperfections. Yes. And maybe also I feel loved when people see who I am. Right. So like we'll leave this conversation and I'll reflect on it. It's like, oh, that person saw a lot more of me. Right? Yes. So I think when people see us fully, we feel loved.

Gosh, it's so true. And what does it seem like in general, there are a lot of us who surround ourselves with people who don't accept us fully. What does that happen? Well, first of all. In like friendships or relationships where someone doesn't fully accept the

other person. Yeah. It's a good question. Well, first of all, remember that on the other side of that equation is somebody else who's also looking for acceptance. So it's never like a one way,

right? So while we're all going through our own journeys, looking for to be seen and loved, so was the other person. So, so I think part of the reason, like it's sort of like ships in the night, right? Everybody is looking to be seen. So maybe what that means is when we stay in relationships, yes, we're hoping to be seen, but the other person is hoping the same thing.

And maybe neither of us are engaging in like an authentic enough conversation with the other, or, you know, like we're so used to looking for it ourselves and you're right so it's a surprise that we don't stop to give it to the other person and maybe it's a two-way relationship i don't know it's a good question oh yeah i mean you could you know you could give the i don't i'm sure you have many more capable people on this podcast on this question than me i'm not a psychologist i am not you know all i can come to is you know know, when we love ourselves, obviously, two things happen. Number one, maybe we have our own renewable source of energy. That's enough.

So while we want to be seen by other people when we love ourselves, right, we come to any relationship able to do two things more. Number one, see other people. You know what I mean? You're not so starved yourself that all you want to do from that relationship is take. You know, but you can see other people ask them the questions about how they want to be seen. But yeah, we all still want to be seen as well. So I don't, I think I'm just rambling.

I don't think I have a good answer to your question. I like this. Was there a moment when you fully fell in love with yourself? I don't think I'm fully in love with myself even now. Really? Yeah, I mean, I think that I'm very... Like fully love and accepted yourself.

Not from like an ego standpoint. Yeah, yeah, no, I understand. No, I mean, look, I still have all the same work everybody else does. I still wake up with imposter syndrome. I still wake up... Really? Of course. I still wake up ashamed of some of the things I have, you know...

Not ashamed. Not shame in the best... Like ashamed of the things I haven't achieved or, not shame, not shame in the past, like a shame to the things I haven't achieved or, you know, the impact I still haven't had. Like, look, the book is an attempted impact, right? So clearly I'm still striving to do something. So, but I would say, so I don't consider myself all the way there by any stretch. What do you feel an imposter about? I feel like an imposter in a good way, like lots of people do. Every time,

look, I think if you're somebody who wakes up and says, job is to have impact right it's never finished no it's never finished and if you have the humility to understand that you are like you know like as we talked about like you're a speck in this universe right yeah most days i just want to wake up and make the most of the time i have i realize it's's finite and that I think I'm here for some purpose. That's what I was trained to believe in my own family spiritually. Like we're all here for some purpose to give. Then mostly I'm just like constantly worried that I'm not fulfilling that promise. So yeah. So it's not like a bad kind of like, right. It's not like I wake up and say, I don't accept myself. It's more like, wow, if I'm not pushing myself to do more and to have more impact,

then I'm not really taking full advantage of why I'm here. So that's the kind of – and so by that definition, you're always putting yourself in situations where it may not be enough. But you realize the only way you're going to have the impact you want is if you put yourself at risk. And so if you put yourself at risk, you feel like an imposter. You're like, oh, because you're practicing some act you've never done yet, right? So anyway, it's like, I'm good with it. Like, I'm good with it. So to your point, I don't fully beat myself up. I don't beat myself up. I've mostly accepted that I have a worldview that says it's okay to be imperfect. It's okay that I never feel fully, you know, capable. I'm pretty comfortable with being personally uncomfortable. And I feel

like that's okay. I feel like that's a way to pursue impact. And so if I'm uncomfortable, but I get the chances and more impact, isn't that worth it? Absolutely. What are your thoughts on the culture of like, I consider you a high achiever, high performer, you're in high executive positions running big companies. And you mentioned something about like, am I creating more? Am I doing enough or creating more impact? What about the people that say, you know, I want to do less. I want to have like less stress, less worry. How can I, how can I create more without the pressure and the stress or anxiety that might seem to come with it. How can I create it and also have inner peace? Is that possible as someone in your position as a high-level CEO and executive

and running billion-dollar companies? Is it possible to have inner peace while also creating massive impact? Sure. So as an example, I identified for you, first of all, this is why I think it is possible. You talked about this idea of self-love and acceptance and understanding what drives you and who you are and why you're here. I may not be peaceful every day, but I am at peace. Does that make sense? Yeah, of course.

Yeah. So I think it's different for different people. I just want to be clear. I'm good with being a CEO. I'm good that that's my path of impact. I am good that there is a higher universe, that I may or may not achieve everything I want. Like, I am, like, totally good with it. So I consider myself at peace because I know that anything may come my way and it will be okay.

Like, look, I could fail miserably and I'll be okay because I have a very good sense of, like, my sense in the universe that I am loved by God. Like, literally, that I am loved, that I am, you know, I'm a full human being, that I am, yeah. Anyway, so I think that if you say, how do you find peace? Look, peace means different things for different people. peace. Look, peace means different things for different people. For me, peace means that I, like, I am in a role and every day waking up and have a way to express my gifts. That for me is peaceful. You know, when I don't feel peaceful, I feel, I don't feel at peace when I don't know what it is. So does that make sense? So like my zone may be a zone of anxiety because every day I think I'm pushing myself to express my gifts. But I'm at peace with that.

So I don't know, like, oh, it depends what you mean by peace. There are people for whom being present in the moment, expressing who they fully authentically are is completely different. And so I think peace means different things to different people. For me, I'm at peace when I'm, like, going 100 miles an hour. Right, right, right. Because that to me is… Chaos is ensuing. And not even chaos, but, like, I'm in hour. Right, right, right. Because that to me- Chaos is ensuing.

And not even chaos, but like I'm in pursuit of impact and purpose, right? Yeah, yeah, yeah. Fully. And I'm fully functioning. And that can be messy. And it's messy, but like maybe part of my gift is I can deal with mess.

If you're a CEO, you deal with mess all the time. You deal with grit. You deal with big possibility and small possibility. You deal with problems. You deal with people being upset. Like, so maybe that's part of my gift, right? That I can handle all those things. You can hold the space for thousands of employees, problems and ups and downs and challenges. That's right. And maybe that's part of what I meant to

do, right? In the world to help people. And by the way, there are many different ways to express your gifts as we come back to. So is it possible to be a CEO and be at peace? Yes. It depends on what you're pursuing. And I think to be at peace with yourself, you just need to know what makes you happy, what makes you fulfilled. What gives you fulfillment? And for me, the pursuit of impact gives me fulfillment. How does someone discover what the unique gift is if they don't know what it is? I would say to people, if you don't know what it is, ask. Ask someone else. Ask the people who know you the best ask what um what's my gift no it's interesting so i'll give you an example like people are like i i so when i give business

talks people you know i start any conversation with like do you know your superpowers and you know like whether it's mbas or like new grads or ceos like a third of the room puts up their hand which i find annoying annoying and like i'm not annoying in a bad way but kind of i'm like annoying annoying for the older people, not the young people. I'm like, okay, if you're telling me that you've gone this far in your career, and you're being falsely modest, that's not that helpful. Because if you're a leader and you don't know what your gifts are, or your areas of vulnerability, how do you ever-

You need to know. You need to know, right? So that's false modesty. And if you're younger, I say, if you don't know, ask the people around you. Like, what do you think I'm uniquely gifted at? And I think sometimes the answers will surprise you, but you'll find the threads of who you are. So I don't think that we're really good at getting, when we're younger, at getting feedback on who we are and what makes us shine. What we get feedback on is, are we good in school or are we smart or what have you? But like what your unique gifts

are, I think your friends and family and even your colleagues will use two or three words to describe you. So you may not say, what's my unique gifts? You're just like, you know, like, what do you think I'm great at? You know, or what do you think, where do you think I shine? And I think you'll hear words that come up again and again and again from all the people in your life that know you professionally and personally. That's interesting. And I just don't think people move through the world with that, you know, with that understanding. Yeah. And I just don't think people move through the world with that understanding.

Do you think we should be pursuing fulfillment then in our gifts over happiness? I guess I believe that fulfillment can lead to happiness. And they think that an impact can lead to happiness. And I know there are other people who are like, hey, just be happy in what you're doing every day and the tasks of what you do. And that leads to fulfillment. And I think it's bi-directional. Like if you want to pursue happiness and happiness gives you fulfillment, great. If you want to pursue fulfillment and fulfillment gives you happiness, great. They're two sides of the same coin. So yeah, I don't know that. I think that there's something ethereal about when you say to people like happiness, like be happy today. I'm like, okay, you can be happy today, but you still need to have bifocals on, right?

Like happy today, maybe some people, their best life is they'd maximize happiness every day. And for other people, their best life is they might minimize happiness on a given day, but maximize happiness over a cycle. Both are possible. It's not an either or or but if somebody says to me pursue happiness every day i'd be like well actually by by virtue being a ceo like every day is not happy you deal with a lot of like messy problems that are very stressful right but over the course of your you know of your career you find fulfillment and you look back and you're like I wouldn't have it any other way so is that happiness too right so but I but I see both like my my husband is a very different

person for me we're kind of very complimentary and I think my husband in a good way perceive you know um like pursues happiness every day that's a great way to be there are days I wake up and I wish I could pursue happiness every day right like so I'm saying the two sides of the same coin. So it's just like better than mine or worse than mine. No, they're just different. He maximizes his happiness, I think, every day or every week. And I maximize mine over maybe two years, five years or a month. It doesn't matter. We're both in pursuit of the same thing. What about you? Do you pursue happiness every day? Or do you pursue, do you have this arc and you're willing to take a lot of unhappiness every day to be? I pursue growth and impact every day.

Yes, you pursue fulfillment leading to happiness. Yeah. Unhappiness leading to fulfillment. But I'm also, I pursue delayed gratification as well. Yeah. I pursue pain. Yeah. So that I can stay healthy. Yeah.

You know what I mean? It's like I do things that are uncomfortable consistently so that I live a happier, healthier life long-term as opposed to short-term like happiness or relief or... Oh yes. And by the way, like I would say, my husband is like that. He's a former athlete or professional athlete. So to your point, on the physical front and so on, he will pursue good health every day. And actually I make poorer choices every day. You know, but we're probably both trying to optimize for delayed gratification in different ways. Yeah, that's great.

Okay, I want to shift the conversation. There's a stat that I saw. Around 65% of businesses failed during the first 10 years. And you worked with a lot of multi-billion dollar companies as well as some failed startups. Yes, yes, there could be both. Why do you think most businesses fail and what can we do to build stronger businesses?

I think a lot of businesses fail for two or three different reasons, but I'm gonna outline the couple that are most important. Okay. And it comes back to what I believe about people too. First and foremost, in anything we execute as entrepreneurs, you know, let's take the example of being an entrepreneur because it's totally related to running a startup. We tend to believe that it's all about us. Remember that worldview I just talked about?

We think it's all about us. Right, right. But most times when you look at businesses, there's like macro and micro. Businesses, like I would say, if you want to understand why you're failing and succeeding, you can say it all comes down to my execution. What could I be doing better? Right. And that's true. You should go take the feedback on what you can be doing and optimizing.

We're going to talk about it in a moment. But first, I'm like, lift your head up. What's going on around you that's impacting your success or failure? So when you look at businesses that thrive, I'm always like, okay, look at the tailwinds that they're riding, you know, or tailwinds that they might be riding or the headwinds they're facing. So I'm like, so I think the first reason that businesses might succeed or fail is they are overly attuned to their execution and maybe not as attuned to the macro tailwinds and headwinds. In the book, I give the story of my sister who ran an optometry practice. And for many years, it was going really well. Yes.

By the way, much more than 10. Like probably ran that practice for 12, 15 years, always growing, right? Growing, and she had employees, had self-fulfilled at work, all of those things, her own boss, all those things. And then it started going to decline. Why? And it started a steady decline. And every year she was eating into more of her savings. And I said, well, Nikki is like, okay, so let's step back.

So let's step back and understand why your business is in decline. By the way, she knows. She's very smart. She's like, well, I'm in a mall. This mall has less foot traffic. There are now three optometrists in this mall. So more competition. The mall itself has less foot traffic because more people are shopping online. Oh, and wait, there's also a

lot of companies that are starting to sell you glasses online. So an optometrist makes their money, not just by doing eye exams, but the most lucrative part of the practice is, guess what? Selling product. Selling products. Okay. So now you look at those macro trends. So Nikki's business is starting to decline. And I'm like, Nikki, let's look at your choices. She's like, well, this is all I know. This is what I know. Like I am doing this for 20 years. And it's mine. And you know, I know it. So let's look at this. Right. So a business that's doing well, then turns into decline. So you could say, Nikki, run faster. Keep, keep your, you know, hours up later. Like, you know, spend more, right? Get

better inventory. Okay. Let's stop a moment. Your location is in decline. You have more competition. This trend is not going anywhere. And by the way, the mall charges you fixed rent and wants to increase the rent. Okay. So at the macro level, is this scenario going to work? You can try and execute your way out of this mousetrap. Is it going to work? And so then we charted a course and she, you know, we laid out five new options. And ultimately my sister ended up taking one after five or six years and sold her practice and moved to a new location and worked for a growing franchise of optometry practices that bought her practice and that's closer to her home and, you know, are able to compete because they have the dollars and capital

to go figure out how they're gonna drive people to their own location. It's not all on her making all the decisions. It's not on her, right? So that's a perfect example of when I say macro versus micro you have to lift your head up and assess the tailwinds and headwinds of your macro situation.

So the first flaw is many people think it's all about them. It's not all about them. Okay, that's piece one. Now let's come to the part that is all about you, which is we sort of want to make one decision and stick with it. And I think this is sort of a big part of the thesis for why I wrote the book. We think it's one decision to success. We think it's one choice to success. And I'm like, okay, well, whether you want to or not, the conditions around you keep changing. You may want them to stay static, but they're not. And so what if I told you that for you to keep succeeding, you need to keep choosing?

It's like actively keep choosing. You have to keep choosing. Choosing new decisions. Choosing new decisions, taking new risks. Yes. Getting in tighter feedback loops, adjusting, adjusting, adjusting, right? Always. Always. So obviously tech is very good at this, right? But we're not this good at this in small businesses or in our own careers. You say, you know how like you want to just do something and set it, right?

Life doesn't work that way. Set it and forget it. Exactly. Life doesn't work that way. Right? So like businesses don't work that way. So like you want to set it and forget it. But as my old CTO at StubHub would say, like product market fit is elusive.

You think that you do something and then you have it. But then something adjusts and then you need to adjust and then you need to keep adjusting. So, like, this is the way our lives unfold. This is the way businesses unfold. So if you said to me, like, you know, why do you, and I think Paul Graham at YC talks about this, like, sometimes to make it, you have to survive.

And surviving is about pivoting, pivoting, pivoting, pivoting, pivoting. Constantly. Constantly. And so I think if you want to set it and forget it, I don't know of many businesses now that work that way because every single business is being disrupted. And by the way, they're not being disrupted by technology, even small businesses. Being disrupted by the pandemic or politics or this, whatever. Local politics.

Everything. A competitor down the street, right? So you have to keep adjusting. Some new innovation that comes out or some new technology. So whether it's micro or macro, remember we said life lives in possibility. So you have to keep pursuing the next possibility because at the minute you're like at stasis, whether you're a small business or whether you're a gigantic startup, you know, with plenty of money, you have to keep adjusting. So first of all, I think people are not nearly heads down enough when it comes to adjustments,

adjusting. They're not willing to adjust? Yeah, not willing to adjust. I think, like, you know, it's like, as I said, they want to set it and forget it. And I think number two, so you have to keep pivoting to keep producting to fit. And then number two, so I'm like, you have to be heads down, but heads down to pivoting. And then you have to be heads up to, like, the environment around you and the stuff that's not all about you and then find your responses. So I know that sounds like a very simplistic thing

for like, why do some businesses, you know, take 10 years to, you know, just like, look, the board list is five years old. It's my own startup, right? It just raised season funding. The board list is always adjusting. Like, I can't tell you what it'll be in five years. It's not the same thing now as it was when it started.

It wasn't. And by the way, if we want to be there in five years, like we're going to have to keep adjusting as we go. And like there's going to be new entrants and new competition and new legislation. And like, and so sometimes I understand that that's like tiring, but that's the way the world works, right? That's the way business will thrive. The only way it'll thrive.

The only way it'll thrive is if you're willing to keep adjusting. Now, the good news is like, if it's a small business, that doesn't mean you have to go, you know, like your adjustments might be micro adjustments, right? But it's like this. You have to change your whole product line and everything. Yeah, exactly, right? And maybe you're going to make a thousand adjustments and one day you'll end up in an entirely new business.

Or maybe you'll make a thousand adjustments and your business will be just a better version of what it is today. I don't know the answer. But if you say to me, like, why do startups fail? And I know that's like a long question, a long answer to your question. I'm sort of like, first of all, it's not all about you. Heads up. And then the part that is about you is about adjusting and pivoting. So, like, heads down, keep pivoting.

How do you learn to keep pivoting when, you know, part of business success and growth and scale is, like, automating systems, having processes in place, having procedures that are constantly then, okay, we've got to constantly shift these processes and shift the software and change these things. Yeah, I should have used a better word than pivoting. Let's call it iterating. So businesses are iterative cycles of focus. So that's sort of my point. So like, let's say you're in your company and competition is like, you know, is increasing. You know, as I said,

there's like 10 painting companies down the road that have just emerged and you run an exterior paint company. I'm like, okay, this is when I, I shouldn't say pivoting. What I mean is like constantly iterating on the part that needs it, right? So you have to sequentially say like, okay, hold the rest of this part.

I now need to go figure out what my marketing strategy is. Okay, when that's done, there will be yet another thing to iterate on. So I think pivoting probably has a higher connotation, as if you're not focused. What I'm suggesting is you have to serially iterate and focus. It's going full way around a circle and then maybe coming all the way back. So that's what I mean more. It's like iterating.

This is good stuff. I mean, I feel like a lot of people had to learn that lesson the hard way during the pandemic. Because if you didn't pivot or iterate, then you're failing. Yeah, yeah. Like it forced you to fail if you weren't willing to evolve.

Right. Well, don't you think, so again, just of like, this is the whole reason this is a good time to have a conversation about risk-taking and how to evolve and grow yourself, right? Because I feel like in the pandemic, people really learned a lot more about their risk-taking ability when times were tough. They either held back or they went all in on something, right? You got it, right. But either way, don't you believe in the pandemic?

People learned a lot more about their agility and resilience and ability to pivot fast than they learned when times were good. Absolutely. Right? So when we're trying to avoid harm, active harm, we often are actually more risk-taking than we are like in our daily safe lives. And you're like, what's that all about? This is a good time to ask that question. Which is why I think that the pandemic should have given us all confidence that we're much more capable of

response than we think you are. Agile response, right? And so your opportunity is, okay, if you know that about yourself, what holds you back when times are good? And it's often things like ego, right? Like personal fear of personal failure, right? And that's why I'm like, okay, believe in like what's possible today and try it. And if it's not, you iterate your way out of it. Like I sort of am believer that you can, if this book's bad, I'm going to iterate my way out of it. If this podcast, you know, if like people are like, oh my God, she's a crier. Like this podcast gets a two rating, I'm going to iterate my way out of it, right?

So I just believe that people learned a lot more about their capacity to respond. And so it gives us all a lot more choice than we think we have. Do you feel like you took bigger risks during the pandemic? Or did you? Oh, for sure. Yeah. I mean, look, I took big risks and small risks. At work, as you know, I was running StubHub and we had just sold the company. A month before you sold it, right? At work, as you know, I was running StubHub, and we had just sold the company. A month before you sold it, right? Yeah, we sold it on February 13th, and on March 13th, our business collapsed.

Like everybody in live events. And it's really interesting because I was running StubHub. I'd been bought in to run StubHub by eBay, which was the parent company of StubHub. And I would say eBay was attracted to me as StubHub CEO because I had just come from being an entrepreneur. I'd been at Google early in my career and scaled, and then I'd been an entrepreneur for seven years. And so I think eBay wanted that entrepreneurial energy back at StubHub because StubHub had been, at that point, was owned by almost ten years by eBay.

And its growth was slowing and costs were maybe higher than they should be. Margin was declining. And so I think I was bought in to bring, you know, maybe higher than they should be. Margin was declining. And so I think I was bought in to bring that entrepreneurial energy, right, and help StubHub pivot. So, and find new services and all sorts of things. So I felt like I spent, and we had, I love the team we had at StubHub. They're just a great group of humans. But I still felt like we spent, I spent one and a half, 1.9 months out of my two years of tenure trying to train people to be more agile. I'm like, okay, guys, you have to make multiple moves. And we can come there next if you want. I have a thesis on what it takes for businesses to really succeed.

And the research would say it doesn't take one move. It takes multiple moves for you to be an outperformer. So we'll talk about that. So I'm trying to train you to be agile. It's like, look, over here we need to cut costs. Over here we need to get international going. Over, we need to get international going. Over here, we need to try new services. Over here, we need to reinvest in the core. You're trying to create a portfolio strategy, but teaching people to be more agile, right? And so here we are,

and for nine months, working to change in the culture and getting people to take more risks at work and all those things. And we're making progress. Leadership development. All those things, right? And then what happens? The pandemic happens and the entire company goes into crisis mode. Really? And within a month, we restructured the business. We changed policies overnight. We took risks to make sure we survived. And we took them rapidly.

And 100% of our employee base was on board, hands on deck, just figuring it out in real time. And it was one of my proudest moments, those most stressful moments as a CEO, because people all learned about their agility. So we made more decisions and pivoted. Think about running a company for EBITDA and gross margin points of growth and revenue growth for 99% of your tenure. And then all of a sudden, you move to a cash flow business. Literally, do we have enough cash? To pay this month's salaries.

Yeah, yeah. Literally. And by the way, we're no longer owned by eBay. We're owned by another private startup whose cash constrained themselves. Like, do we have enough money? Oh my God, customers are asking for hundreds of millions of dollars in refunds. Like, where is the money? I mean, like literally you go to managing on cash. Like you go to manage daily, weekly, monthly cash for a company that hasn't been used to that for like the entirety of its last 10 to 15 years, right? So 10 years at least under eBay. So anyway, long-winded way of saying I think that we learn more in crisis. I learned more certainly as a CEO was the most intense period I've ever been through.

What did you learn about yourself? What did I learn about myself? Honestly, in the pandemic, I don't think that I learned that much about myself. I don't mean that in a bad way on the business side. Remember, I've been a startup CEO and I've been through crises. I have been through crises. So what I learned about myself is, thank God, I have lived a life of cyclicality and entrepreneurship that maybe makes me well positioned for this moment. It's not like in the time I was like, I'm well positioned. It's more like I felt stable and secure and capable.

I felt capable. I felt the same thing during the pandemic. Yeah. Like, I mean, I felt nervous. Don't get me wrong. Like on edge. Yeah. Scared a little bit.

Yeah. But capable. Yeah. Scared, but capable. Responsible, scared a little bit, yeah. But capable, yeah, scared, but capable. Responsible, but capable. Like, do you know what I mean? So I felt assured of myself in the moment, but I felt obviously a lot of anxiety for our team. So what I learned about myself in the pandemic,

that I felt grateful that I'd had this set of experiences before. But in that moment of responsibility, I was like, I can do it. What I felt like I learned most is what I already knew about our people, which is you are capable. Okay, so what I learned in the pandemic is,

I felt like saying, I know you're capable. Look what you just did. So that was the gift of the pandemic, helping other people understand that they are capable too and being a leader in that moment, which is like, look what we just did. We were able to do this. You would never have guessed that you would see this situation.

Neither did I. You are capable. By the way, it's not that we handled it perfectly. It's not we didn't have pissed off customers, whatever, but we needed to deliver and make sure, and make sure the company survived. And we did. And that was 2,000 people. That wasn't me, right?

That was 2,000 people coming together, cutting their own jobs. Like, think about this for a moment. People who are, like, understand that they're going to have to make sacrifices to give up their own security. I mean, it was painful, but people understood they were capable. So I think that's what I learned. And then on the personal side, what did I learn through COVID? I learned the importance of all the things my husband was always telling me. He's like, why are you commuting for God's sake?

You have hours a day. And I'm like, I have to. So I have to. I have to be present for my employees. I have to commute. Like the only jobs are in San Francisco. You know, my husband. Where are we living?

I live in Silicon Valley. So I mean, keep in mind. So like an hour commuting. An hour each way. I mean, so for 20 years, right? I live in Silicon Valley. So, I mean, keep in mind. So, like an hour community. An hour each way. I mean, so for 20 years, right, I've said to my family, you know, I have to do this. Like, right? And my husband's like, really? Do you have to?

And so, I would just say, what else did I learn? I was pretty schooled on all the things we think we have to do. You know, that your family tells you, do you have to do this? So, for all of us who are CEOs who make our families sacrifice a ton for our careers and our ambitions, like I felt like I learned that, in fact, the commute has cost me a lot. Really? In terms of my, you know, just in terms of like my productivity, my time, my energy, being home for dinner, you know, all of those things. And then I felt like many people, the COVID learning for me was like man look at all that we

you know we miss of like our families and each other and again like this is not like some saintly view I'm sure I'm going to be capable of many sins as like hybrid works comes back but you know just the joy of like seeing your kids every day you know having them all home for a moment like all of those

things like yeah I saw all those moments too and I was like wow what have I missed and of course, as I go back to being a CEO again, I'm inevitably going to screw it up. But I said to my, I said to my family, I was like, can we just keep like one or two COVID rituals as everybody goes back to their thing? You know what I mean? The kids go back to practices. And so I, like everybody else, there's less to make for it. Like maybe I can hang on to one or two of these things. I'm pretty sure I'm gonna like screw it up on a bunch of other things

because I just love work too much and I sacrifice a lot of my personal life to it. But hopefully we keep a few things, a few COVID practices. I wanna talk about wealth creation and wealth building. Sure. What do you think are the three most important steps to building wealth for an individual?

Ownership. Like literally equity ownership. Like you look at the most wealthy people in the world and if you want to be wealthy, you need to be an owner. They have equity in something. They have equity in something. You have equity in your small business. You know, you're like my sister. You have equity in your practice and you sell your patient files, you know, to a bigger partnership.

Or you're like me and you have equity in a big company or small company, whether you started it or not. Equity ownership is the key to wealth creation. That's why people own their homes. The biggest source of wealth for people, home ownership, right? You have to be an owner. Okay. That's one. So, yeah.

For sure, that's a big one. Number two, you know this. Everybody knows it, but we need to do it. Saving. Just like saving early but we need to do it. Saving. Just like saving early and compounding returns. Yeah. I think is the second. A lot of people don't do that.

A lot of people don't do it. I started doing that years ago. Most people don't do it. Even when I didn't have that much money, I was like, even 500 bucks a year, 1,000 bucks. You know, when I was broke. I know, right? It's just something. It's amazing.

I remember I started at like 27, maybe, starting to like my IRA and then just other investments. And I was like, but I don't have that much to invest to save in. Yeah. I wasn't making that much. But now, 11 years later, I'm like, oh, look what I've accumulated. Well, more importantly, saving allows you to do what? Become an owner. Right.

You can buy something with it. You got it. These are inherently related, right? So if you say, like, if you don't save, guess what? The day that equity ownership comes up to buy a piece of a home or these days a piece of a home or land or stock market, you know, equity in the stock market. Collectibles, art, whatever you want to, yeah. If you don't have savings, how do you become an owner? It's impossible.

So these two things are inherently related, right? So even though it's fractional ownership, which we all have opportunities for now. So I think in order to become an owner, you need to accumulate savings. So I think that's the, I think that is, those are my two. I don't have a third. Those are it. Those are the two. What about the mindset around wealth and creating more financial abundance? How do we shift the narrative from thinking money's bad or I don't understand money or I'm not educated on it so that I'm not going to receive it? How do we change the mindset of the conversation we have around money? Because I feel like a lot of people don't talk about it enough. Yeah, I know. And I don't know. There's no shame in wealth creation, right? But I think

there are two things. First of all, financial literacy is so key. You know this. I mean, if you don't have financial literacy, it's hard, right? So I was lucky that I give my dad so much credit. My dad owned equities. He literally owned stocks. He would call his broker and buy them every day. So I saw stock ownership as a thing, right? And then I ended up becoming a financial analyst.

So of course, I got financially literate. But my point is if you're not literate, getting literate about is how you understand savings and ownership, what have you. So I think that literacy is sort of one way and not to be afraid of these conversations. What are two books you'd recommend to someone on becoming more financially literate? So to be honest, I've never read a book in my life

because I did it all on the job. Yeah, yeah. So I think I'm a poor person to answer that. Just kidding. If you said, like, have you read a book on financial literacy? I did it all on the job. So I think I'm a poor person to answer that. Just down. If you said, can you write a book on financial analysis? I'd be like, I had mentors and my first job was as a financial analyst. So I went to undergraduate business school. So I did my dad's taxes. Understand, I did his taxes. I started teaching us to do his ledgers, to literally write numbers in a ledger when we were seven or eight. Yeah, wow. Doing his taxes was a family affair.

That's crazy. No joke. So when I say I was grown financially literate, that's actually true. So I don't think I'm a good person to recommend a book. But you could probably have a client of yours who would give people the best recommendations. So I think literacy is one. the best recommendation. So I think literacy is one. Number two, I think if we are a female and in a relationship, we tend to think that there's some shame in asking the other, you know, like your husband or, you know, whatever, whoever is the wealth store,

like you have to, to your point, you have to ask. Ask what questions? Well, you have to ask like, where are our bank accounts? What do we have? Like if you just, it's not just a question of being literate. It's a question of being literate. It's a question of being informed and not just trusting your financial decisions to other people. Yes. Some people, if they're not literate, they won't ask. I'd say the converse is true.

You can be literate and ask at the same time. So if somebody is managing your money, you better fricking know where it is. And part of getting literate is being comfortable with asking questions. So I think there's literacy and there's information, and they're very highly correlated. So I know people who their husbands or manage all their money. I know people who give money to their broker and they don't know what their broker is investing in. I'm like, okay, so one is literacy, but one is sheer information. So I see a lot of people who are like, this is an uncomfortable topic, so I'm just going

to also outsource not just literacy, I'm just going to outsource information. Somebody else has information on my financial well-being. That's a little crazy to me, but I see a lot of people who just don't want to have the conversation. More often women than men. This is why platforms like Ellevest and others that are driving women to manage their own wealth, I think, is disproportionately important. So I think that's very key.

How can women change the mindset around earning, saving, investing, and becoming more, having more ownership of their money mind? Well, first of all, I think many women are. But I just think that platforms that do it, I think anything that gives you education without it being intimidating is very critical. So I think women are doing it more and more, but I think that platforms that can accelerate your knowledge or your management of your own money is key. The third thing you can do, as we talked about, take a little risk. If you're too afraid to manage all your money, take 10% of it and say, I'm gonna manage this directly.

And then the third thing I say to people is, if you wanna start creating wealth, invest in what you know, okay? So people think that- Don't invest in crypto if you don't understand it. Yeah, yeah, exactly. So it's not just like literate about like how financial systems work,

it's like literally invest in what you know. So I've become an e-commerce investor over the last 10 years and a pretty good one. But that's because I was the e-commerce CEO. And so while I understand the business. And so I was practicing every day. I thought like, God, like I know enough about these numbers to know where our numbers look good or bad. But that gives me pattern recognition and becoming an angel investor.

So as opposed to like, yes, I had diversification of wealth across different sectors or diversification of angel investments across different sectors of e-commerce, but literally I doubled down on e-commerce because I understood that business. When I was an analyst, I was at Merrill Lynch early in my career and I worked on the financial services industry, the savings and loan industry, which is the most, you know, I learned about savings and loans, balance sheet and loan industry, which is the most, you know, I learned about savings and loans balance sheet and income statements. And the first stocks I ever bought were in the savings and loan industry because I was like, I understand what good looks like. So I think if you want to create wealth, you know, you need to understand what you're investing in.

Let's say you're going to buy real estate. Okay. Well, you need to understand the neighborhood. You need to understand the comps. You can't just fall in love with a house and say like, you know, is this a good investment? It looks good. I'm just going to buy it. Yeah. Yeah, yeah. But I mean this, like, one and done. Somebody shows you something, you know. Right.

So I think there's generally literate asking about your own money and understanding, like, where it is, who's managing it, like, what's there. If you're shy about it, like, I think that's – and then I think number three, very specifically literate when you want to invest in something. Yeah, yeah. Someone feels like a failure, like they have these failure conversations with themselves. They feel like they have a lot of negative thoughts. How can we overcome these negative thoughts and help us get out of a rut if we kind of feel like we're always stuck in that failure mindset? Yeah, look, I think that when people are looking at failure, one of the reasons I think failure is so daunting for people is because they think that a choice is binary. So I think there are two things that you need to do if you want to get out of failure mindset.

First of all, you have to get out of this idea that you have one shot at glory. So we fear failure because we think whatever decision we make is what Jeff Bezos calls a one-way door. I go through this door, there's no coming back. It's going to define me forever. It's going to define me forever, right? When Jeff Bezos in the shareholder letter to Amazon shareholders said, very clearly said, most of the decisions we make at Amazon are two-way doors.

You go through, it doesn't work out, you come back. So I think that most people have the perception that failure is the result of a binary choice. You know, you make one choice, it fails or succeeds. Now, if you believe like I believe that actually between you and a reward is probably not one decision, but 30, 40, 100, should you really overweight the importance of the first decision? I would say you should overweight your ability to keep choosing. If you can keep choosing, you will find a path. You may not end up where you started, but you know, where you wanted when you started,

but there will be a path. But you have to dismiss this myth that failure is a bimodal binary one-way door. It isn't. It's just the first choice in a series of choices you will inevitably have to make. So first of all, stop thinking about failure as a one-choice circumstance. It's just not. Then number two, and I will say this, supposing the decision you're contemplating is in fact bigger, and it is a one-way door.

I make it up. You mortgage your house. You're starting a company. You can't take make it up. You mortgage your house. You're starting a company. Like, you know, you can't take back the mortgage. You quit your day job. You go to zero salary and you mortgage your house. Okay. We can agree that's a big risk.

In that mode, I always say to people, like, okay, well, if it's a big risk, then as opposed to planning for all the upside that's going to happen, I said, plan for the failure mode. Plan for the failure mode in order to get yourself to act. And people are like, what do you mean? I'm like, okay. If something's really, you know, a big and scary risk, I want you to tell me the five choices you'd make after the choice. Tell me. Like, what are they?

Like, what are the two? What are the three? What are the four? If it fails. If it fails, play through the failure. Tell me the five choices. And then I bet that you will find two, three, four recovery paths. But actively think about that now. Park two, three, four recovery paths. But actively think

about that now. Park all of your magic of the upside. Okay, that's great to get what I call your FOMO going. You'll get really excited. Fear of missing out is like, you know, you want to act, you visualize the positive. But when you're trying to overcome failure, I'm like, visualize a failure, work it through, understand all your contingencies, and then you're probably far more likely to get into action because what you've done is reduce your fear of failure because you're actively imagining the choices after the choice when it fails. It's interesting you say that because I was interviewing a UFC fighter, George St. Pierre, and it was one of the greatest of all time.

And he was talking, I think it was him or another UFC fighter that I heard, I can't remember which one it was, but talking about how they train to be in the most uncomfortable situations. Like I'm on my back, my arm is behind my back. I've got a hand here and a guy's just punching me in the face. How do I get out of this? Yes, that's exactly right. How do I get out of it? How do I stay calm? How do I not like pass out? How do I, you know, if I'm in the worst position possible, like every bad position I train for and I train to get out of it yeah so that when it does happen yes i'm like this sucks and it's uncomfortable but i know i can get out of it yeah and if i can just get back on my feet and stand up again then i can take the next step right exactly and then and and i think for

people who are like i fail let's say you pick a new job and you left your old job and you cut your ties and it fails i'm like okay what that what pick a new job and you left your old job and you cut your ties and it fails. I'm like, okay, what then? So play through. You lose your relationship. You lose your kid, everything you lose. Yeah. Yeah. Then you're like, okay, well then what would you do? Because I think that on small failures, it's tough to know that if you act once, you still have 10 more choices. On something that is like truly a one-way door, there are very few decisions that truly you can come back from. And those things you're like, okay, then what are my contingencies? What do I do? So I believe that this risk-taking equation guides all of us, which is fear of missing out is worn with fear of failure.

Whichever one is, fear of missing out is greater than fear of failure, you'll take action. If fear of failure is greater than fear of missing out, you won't. But most people only want to work one side of that equation, which is think about the positive. And I'm like, no, you got to think about both. Yeah. It's really, it's yeah. One of my coaches, Chris Lee, years ago, probably like seven years ago, I had been training for years already to overcome the fear of public speaking. Oh, really? And I'd been speaking for, I don't know, at this point, 10 years professionally, and I'd made good money on stages and spoken in front of 20,000 people. And I remember saying to him, I was like, gosh, I don't know why, but I still feel like kind of

scared and nervous. Yes. Like the day before I go on. And I don't know why. And I remember calling him like hours before and I go, I don't know why I'm still nervous and a little afraid. And he said, because one of the things is you're afraid of how you're going to look. You're afraid of like being embarrassed or not like saying the right thing or messing up you're still afraid of that as opposed to being of service to the audience and knowing you're going to mess not it's not going to be perfect and he put me through an exercise like what well like a what if or what happens next exercise just go okay what if you what if you forget your words what if you forget that story then what then what then what? Then what? Then what? I call that the choice after the choice. Then what? Then what?

Well, then I'll be embarrassed. Well, then what? Well, then what's the worst that could happen? I don't know. Then I just walk off stage and I forget the whole thing. And then what? And then what? Well, everyone laughs at me. Okay. And then what? And then I don't want to come out for a week because I'm so embarrassed. And then what? It's like eventually you're like, okay, I'm down here and I'll pick myself back up and I'll be okay and I'll start again. Yeah, I think that that's sort of the point. Like the then what, then what, then what. We sort of have trained ourselves to think that it has to be, you know, that like I said, it's bimodal. I'm like, it's not bimodal.

It's like what will happen is you'll discover there are five choices after choice. So think those through now. Yes. Because in there is comfort. That's so good. That's so good. What is the thing that you're most proud of that most people don't know about you? What I'm most proud of career-wise is I have had a career of working with exceptionally talented people where I feel like I got to be part of accelerating their journey.

That is what I'm most proud of. Like I'll look back on my life and say, regardless of the countries or whatever, I just look, I always say to people, do you know how amazing it is to work with tribes of great people who are by and large great human beings as well? And then be like, oh, yeah, I will look at my journey and be like, I got to intersect with these amazing people. And maybe for a few of them or hopefully some meaningful number

of them I was an accelerant so that's what I'm most proud of kind of business wise what am I most proud of that people wouldn't know about me maybe that I think I wake up every day both fully empowered and also pretty clear that I'm like pretty far from the center of the universe. Like I'm proud of the fact that I think that most people would think that I wake up thinking I sort of must rule the roost. And most days I'm like, no, I wake up pretty empowered, but I'm really grounded and clear that, you know, life is a blessing. I'm here for a reason. I'm living my impact. The world is a much, much bigger place than just me.

Yet I feel very stable within it. Like I don't feel like many things. Nothing's going to shake me. Yeah, because I have a sense for why I'm here and what I'm meant to do without thinking that it's all about me. So I'm proud of that. That's cool. I'm proud of that. That's great. I'm like, I'm good with it. all about me. So I'm proud of that. I'm proud of that. I'm like, I'm good with

it. That's great. The book is about risks and you said most things won't shake you, but when people take big risks, sometimes it shakes them a lot. What's the biggest myths around risk-taking that we tell ourselves? Yeah. And by the way, of course, if you read the book, you'll know that many risks I took shook me, which is the whole reason for writing the book. Because I'm like, don't let it shake you. This is what happened to me. So I can't say I've never been shaken by risk. But I think I keep coming back to that singular point. Like, I know it sounds so simple, but it is the point of the entire freaking book.

The book is about how, but the point of the book is about, you know, let go of this myth of the single choice. Stop believing that outcomes are binary, that risk and reward is a singular linear game. Like, hey, I take a big risk, I get a big reward, you know, or I have an epic fail. Like, it's just not like that. Yeah. It's either I win big or I lose it all. Exactly. That is this bimodal issue. I think that is the biggest myth around risk-taking Yeah, it's either I win big or I lose it all. Exactly. That is this bimodal issue. I think that is the biggest myth around risk-taking. And it's the whole reason I wrote the book. I'm like, you have to keep choosing.

Stop over-weighting the first choice. If you are willing to keep choosing, there are a thousand choices between you and success. And I cannot promise you that the success you'll get at the end is the one you originally thought. It may or may not be. But I can tell you that if you keep aiming for impact in every single choice, cumulatively you will have an outsized career and you will have an outsized life, cumulatively.

But if you wanna measure yourself on every single choice, I can tell you that the people I know who succeed greatly are pretty freaking imperfect. They're master risk takers as measured by small and big acts of possibility, right? As opposed to this one big act of possibility for which they're famous. Like, no, they roll by becoming a master at the process of risk taking and constantly choosing. They're just, right? They're very skilled at continuing to choose. Yeah. I'm curious, do you believe that it's harder to go from zero to 10 million?

Like in startup, like here's my idea. I'm launching the business. Zero revenue coming in to 10 million for the business. Or taking over a company from 100 million and taking it to a billion. Which one is harder and why? Interestingly, I think zero to 10 is exactly hard. It's hard, right? It's hard. It's hard. It's hard, my friend, because as we talked about, you're trying to find essential product market fit. And so I think it's

just really hard. And when you have momentum, everybody wants to work with you, right? So things unlock fast. Creating momentum is really frigging hard. It takes so much energy. A venture capitalist who was on my board once described, and I think he said it the best, but I'm not going to do it justice. He said, when you're in a startup, you have your hand on this gigantic wheel and you're trying to turn it once, one big wheel to get momentum. One revolution of the wheel takes so much energy right and these like and then when you have like a bigger company and you have product market fit it's like one revolution first of all you can get through one revolution very quickly and just like it creates so like and you have many many more turns each of which are producing more energy does that make

sense yeah so it's like it's like trying to get that first revolution to create any momentum. Because if you can't even get the wheel to turn once, there's no momentum or energy, like net energy output. But once you have energy in a system, then turning the wheel is easier. And every time you turn the wheel, more energy spits out, right? Yeah, I think Jim Collins in Good to Great, I think, calls that the flywheel. It's like just like keep the flywheel going. You know, that's one of my favorite books. Is that one of your favorite books? I love that book.

It's a classic. It's very like heady for me, but yeah. Oh, really? It's very heady for you? Well, I'll tell you the part of it just coming back to our previous conversation. It's a great book, though. It's a great business book. I understand that it's a little very analytical for you.

But come back to it. There's a point he makes in that book, another point which we didn't, which I should have brought up, but I didn't. We were chatting about the choice after the choice and the then what, and the then what, and the then what. You probably remember from the book

his story about Jim Stockdale and the Vietnam War veteran who talked about like, who was a prisoner of war in Vietnam and ended up being, do you remember this story from the book? Go ahead. He basically,

like Jim Stockdale, I think it's Stockdale, was a decorated Vietnam veteran, prisoner of war, who helped send Morse codes out and get his whole cohort rescued before the war ended. But he made the point that the people who were pure optimists were the first to get really depressed in camp because they thought they were being rescued tomorrow. And then the pure pessimist... Someone's coming. Someone's coming every day. And then when they didn't come, they didn't know how to handle that failure. Right. So they got very depressed. And then there were other people who were like, nobody's ever coming. And they were also depressed. But he said the people who did best in the, you know, in the POW camp were really like

realistic optimists. They understood that it was unlikely that somebody was coming next day, but they had faith that somebody was coming, right? And so your job was to survive every day until somebody came. So I love that mentality. I'm like, yes, you can be paranoid every day about what it takes to run your business and iterate and pivot and what have you, while having faith that if you like go through this process and keep doing it, you will survive and you will thrive. Right?

So that's what I mean about being bimodal. You can be paranoid every day and be like, I have to iterate and I have to pivot while still being fundamentally an optimist over the long term. But it's that ability to pivot that actually makes you the optimist, right? It's not like you have to go into it being like, everything's going to be perfect. Everything's going to be perfect or everything's going to be terrible. I'm like, no, no. You need to be a long term optim optimist and a short-term realist.

What's a question you wish more people asked you they don't ask? I think most people ask me, Sukhinder, what would you do? Let's say we're in a leader. Like, Sukhinder, what would you do? And I think most people should ask me, what do you think I should do given who I am? Right? Everybody comes to a leader and they want the answer. And I think I would love more people to say to me, okay, it's not about what I would do, it's about here's who I am, here's my goal set, here's my vision, what do you, given this. Based on that, here's what is the best solution.

Because I think it's not about me giving somebody an answer, right? It's about I want to know who are you and what do you think the answer is? What's your thesis to which I can respond and try and give you some insight that fits with who you are and what you want and what you believe, where you have conviction? So mostly I think that people should ask me that question. Like, what would you do? It's not about what I would do, it's about what would you do? When I call you, I'm like, I should ask that question.

You'd be like, Sukendra, here's what I'm thinking. Yeah, yeah. You know, what do you think? Here's whoendra, here's what I'm thinking. Yeah, yeah. Here's what I am. Here's my unique gifts. Yeah, yeah. Here's my thesis. What do you think I should do given that information? I'd be like, oh, okay, well, this is what I would reflect to you. Right.

And don't get me wrong. The problem is if you ask me, like, what should I do? Like, I'm going to give you a straight-up answer. Then you're going to think that that's what you should do. And that's not always the right answer, right? Maybe it is, but it's... Maybe it is. Maybe it isn't.

But, like, you know, it's the wrong question. And then if you're taking action based on what someone else would choose to do, it might ruin the whole thing or it might go in my direction. I think we like go through the world asking people who know us, like, what would you do?

They might be like, well, here's my reflections. That's interesting. What do you know about me? What do you think I should do given my own awareness? And like, what do you think? What am I missing about,

you know, in this equation about who I am in this situation? And what do you think? What am I missing in this equation about who I am in this situation? And most people probably have a better reflection for you based on who you are and your unique gifts and capabilities and capacity. But you have to show some self-awareness first. You got to be self-aware. Excited about your book, Choose Possibility, Take Risks and Thrive. Even when you fail, and I think a lot of people, it's hard for people to have this mindset of failing, but I've always been told that failure is just feedback as an athlete. It's just like, I failed every day in practice and games.

It's like, you never made a hundred percent of your shots. You never caught the ball a hundred percent of the time. And it's like, okay, that's information. How do I use that to become better and not get down to myself, but to improve myself.

And so failure has always been a part of my life. Cause it teaches me something. Right. So take risks and thrive even when you fail. But I think a lot of people are just afraid to take the risk because they don't want to fail. They don't want to have that. Even a micro failure, it's like, well. Yeah. And I don't think they think of, I mean, look, I think there's a couple of things that are going on. First of all, if you're an athlete or you're, let's say, in a startup or what have you, you're used to this idea that iterating, every iteration is feedback, right, in a feedback loop. You're also used to probabilities. You know that in baseball, a 300 batting average is actually amazing, right,

whereas in the NBA it might be, I don't know, maybe the top shooters are 76% or whatever. I mean, it depends, like, what the, you know, from the field or what have you position, right? Or you might know that if you're a trader or a hedge fund manager, but you know that it's a game of probabilities. So why do we tell ourselves it's like one shot? Like, why do we think a winning season is like one shot? And then we put all of the weight on that choice.

I, you know, it's so, I think that is that is actually the key for all of us. It's that risk-taking is a muscle. It can be developed. The book is more about the how than the what, but it's both. It's like, yes, this is the principle, but I think when people say have a growth mindset, I think people need tactics. They need a structure.

They need tools. So hopefully the book gives you some of that. But yeah, it's always amazing to me. I'm like, we don't pick in probabilities of our own life. We think that every single choice is the one that makes or breaks us. Right. That's not true. That's not true.

Isn't it? It should be freeing for people. There are many shots on goal. Absolutely. Many shots on goal. Yeah, you've got a lot of different like equations in here and different examples. Frameworks. Yeah, it's really cool.

I know. Maybe it's a little too heady for you. No, it's all right. I'm always impressed with people who can do like frameworks and equations and formulas and make it, map it out because I never know how to explain it and position it that way. I'm always just like, well, this is how I do it. I don't know how to, but like when someone could do this, I'm like, I really appreciate it. Uh, even like the self-awareness sandwich, you know, it's like the framework, it's okay. I would just try to like explain it in my mind. Well, this is how I feel. But you put it into a diagram. It's like, okay, that makes more sense. So I'm always appreciative of this.

People should get the book. It's called Choose Possibility, Take Risks and Thrive Even When You Fail. So Kendra, I want to acknowledge you for a moment. I've got a couple of final questions for you. But I want to acknowledge you, Kendrainder for your vulnerability and your unique gifts it's it's um it's really been a pleasure to connect with you and to hear your stories and hear your connection to your gifts the lessons from your father the lessons from your experiences as an executive at a high level being a female executive and founder the mindset around wealth which I think a lot of people are afraid of so I I acknowledge you for opening up, for sharing, for being real. And I think we were able to create something inspiring today. So I really acknowledge you for your gift and hopefully we can stay connected and I can help

in any way possible. This is a question I ask everyone towards the end called the three truths. So I'd like you to imagine a hypothetical scenario. It's your last day on earth many years away. Live as long as you want, but eventually you got to go to the next place. You got to go. Yeah, we talked about this. We're all going to go. Yeah. And for whatever reason, you've accomplished all your greatest dreams. Everything you want to accomplish has happened, personally, professionally, everything. But you've got to take your work with you. The book, this message, all your conversations got to go somewhere else, whether with you or not here on this earth. So no one has access to your information anymore. But you have a piece of

paper and a pen and you get to write down the three biggest lessons you've learned from your life that you would leave behind. And this is all we would have to remember you by. I call it the three truths. What would you say are yours? Number one, possibility lives in acts big and small, for sure. So I always say to people, you don't know if you don't try, right? So that is just embodied, I think, that just remember possibility is in acts big and small. So get started now. You'll never know if you don't try. I think that's one.

I think number two, I would say we're all here to maximize our gifts and have impact. So discover yours. And I'd say number three, and maybe this is unique to me given how I was raised, is put it in perspective. It'll all be okay. We're all here as part of something much bigger. You're loved. You're seen.

Regardless of what happens, you will be okay. Yeah, that's cool. That's a good truth. I'm curious, not to get too emotional here, but what do you think your father would say if he saw you now of everything you've created in the last couple of decades? First of all, I think he would say,

remember that all that you've been given is like a gift. Just remember that. Remember where it comes from. Of course he would acknowledge it and acknowledge my things I've achieved, but mostly I think he would acknowledge the universe. And he would be like, I think he would just say, you know, feel grateful. Feel grateful and understand where it all comes from. Yeah.

So, of course, he would make me feel great. But he would also remind me, which I'm very clear on. Like, I feel just grateful for my, you know, for everything I've been given. Right. Yeah. Gratitude is key for sure. Final question before I ask. I want to make sure everyone gets the book,

Choose Possibility. Where can they go? So can you sing on Twitter? You're not on Instagram. I tried to look for you. Oh, I hide on Instagram. Okay, cool. You know what?

It's just another, you can find me on LinkedIn. I'm most present on LinkedIn and Twitter. I do have an Instagram account. I never post. I just follow. Because it's just another place to be responsible, right? And like in a world where like, that's where I'm like, oh my gosh,

it's like one more thing to like take care of. And my life is so full right now. I know. So Twitter and LinkedIn. Choosepossibility.com. We can get information there. Is there a personal website for you as well? Or is that?

You know, my personal website is a book website. I don't have a book website. But the best and most active place to find me is LinkedIn. LinkedIn. Yeah, that's where you can just find me at Atsi Kindersen. You can find me at, you can actually on LinkedIn might be Atsi Kindersen-Castey. Okay. I guarantee if you put my name in the LinkedIn, you're going to pop up on my handle. You'll pop up right away, yes. And you can follow me there. You can certainly follow me on Twitter. Most importantly, you can buy the book wherever you want to buy books. Awesome. I mean, wherever you buy them, there's

an audio book, Amazon, all the usual places. Inspiring stories, inspiring frameworks, lessons. I love it all. Final question is what's your definition of greatness? It's what we talked about earlier. I think it's people who not only create impact in their own lives, but they create impact and possibility for others. Powerful, my friend. If you want to be great, stop just generating possibility for yourself or stop thinking of it as like, I have more possibility, you have less. If you have possibility,

your opportunity is to generate it for other people. Right? So that's greatness. So Kendra, thank you so much. Appreciate you very much. Appreciate it. Amazing. Thank you so much for listening to this episode.

If you enjoyed it, make sure to share this with a friend, someone that you think would be inspired by this as well. Or you can post this over on social media, just copy and paste the link lewishouse.com slash 1150 or whatever link you're listening to on your podcast platform of choice. Just share that over on your stories or on social media and make sure to tag me as well over there. I'm at Lewis House. And again, make sure to click the subscribe button right now over on Apple podcast or Spotify and leave us a review as well of the part you enjoyed the most about this episode. And I want to leave you with this quote from James Cameron, who said, there are many

talented people who haven't fulfilled their dreams because they overthought it, or they were too cautious or were unwilling to make the leap of faith. I want to make sure that you are willing to overcome that insecurity, that doubt, that fear that holds you back from going after or pursuing the thing that you were called to do. Whatever that thing is inside of you right now, go do that thing. I don't care if you take baby steps or big leaps going after it, but just moving in the direction. It's going to make you feel more alive, make you feel more confident,

make you feel more aligned to your greater purpose right now in the direction. It's going to make you feel more alive, make you feel more confident, make you feel more aligned to your greater purpose right now in your life. I hope you enjoyed this episode and I want to remind you if no one's told you lately that you are loved, you are worthy, and you matter.

And you know what time it is. It's time to go out there and do something great.