Never Ready, Never Alone: Suneel Gupta on Playing the Game of Now

0:00The game of now and taking these actions, they do take effort, they do take energy, and it does require adaptability as well. Because when you take an action, it doesn't mean that you know what the rest of the roadmap is going to look like. One of the principles of playing the game of now in your life is to know that you don't have to know the last step in order to take the first step.

0:24What would happen if we just told the truth? Welcome to TruthWorks, where we dig into the nitty gritty of leadership and work. And what needs to change. I'm Jessica Neal. And I'm Patti McCord. Our journey together started in HR, but trust us, it's evolved into something wild, honest, and well, a bit rebellious. So throw out the handbook. We're here to redefine rules to work for us, not against us. Let's dive into another episode.

1:02Hello, everyone. Welcome to another episode of TruthWorks. I am Jessica Neal and I am your host. Patti McCord is coming back, y 'all, but not today. But more exciting than that because we're all very excited about Patti coming. I have an amazing guest that I'm so excited about today. I don't know. I was watching your videos this morning and can't wait to talk to Sunil. So we have Sunil Gupta on the show today. And many of you probably know Sunil's work, have read his books, or maybe you saw his show on Amazon Prime business class. But I don't want to tell everybody your whole story, Sunil. I want you to tell it.

1:43Like, I don't even know how you did all the things that you did and where you got to and like Harvard and Amazon Prime and books. And so tell me the whole story. How did this all start? Really, honestly, Jessica, by accident. I mean, we're on a show that tells the truth. I'll tell you the truth. Okay. This was all grounded in a series of failures. I had started two companies that did not work. I had joined another company, which you might be familiar with, called Groupon. And I was sort of their first head of product development. So very early on the team, and we went through this explosive growth period.

2:22Where Forbes magazine called us the fastest growing company of all time. And then we just kind of imploded. And so, you know, I had sort of not a great track record. And the New York Times was doing a story, this is 10 years ago, on failure, on people who fail. And they chose whose photo to be the cover of this article? My photo. Wow. My story. Did it ask your permission? Well, yeah. I mean, they sort of attended a talk that I had given. So it was out there publicly and I talked pretty openly with a group of entrepreneurs about my failures because I felt like it was an important story to share.

3:03Yeah. They didn't have to ask permission because I had already sort of shared it all. I was surprised to see that I had become the poster child for failure for the New York Times. And I was also surprised to see how viral that story went because you'll remember, you know, failure kind of went from one of these things that nobody was talking about to all of a sudden the thing that everybody was talking about. And this New York Times article was a big part of that sort of that transformation. So there was a point in time, I kid you not, where you could have Googled the word failure. That's it. Just the word failure.

3:34And my face most likely would have been your top search result. Your name was really like in the dictionary. Like, look it up. There's my name. I know that. There's my face. Well, I mean, kind of cool. Yeah, well, so, you know, in the beginning, I'd say it was kind of a bury my head in the sand kind of moment. You know, I, I did, I did, I did, I did because, um, yeah, I wanted to be perceived as successful. You know, I just, I, that was, that was, that was it. And, and, you know, I think that for me, even though I would sort of laugh about it with my friends at the bar, like, you know, it was, it was one of these moments where it's like, you know, this is how I'm going to be known now.

4:16But, you know, a mentor of mine gave me a piece of advice. And what she said to me is, hey, long-term success comes from short-term embarrassment. And if you can learn something from it, if you can do something with it. So one day I got the idea to start emailing all these people that I admired, people who had no idea who I was, this article. I would literally find their email address and I would send them a link to the article. And I'd say, hey, as you can see, I'm the poster child for failure. I don't know what I'm doing. Would you be willing to give me some advice. And the response rate, the response rate to that email was extraordinarily high.

4:51Who are these people who was on the list? From like, from like, from like Oscar winning filmmakers like Brian Grazer to, to leaders of large iconic companies like Reid Hoffman, to coaches of professional sports teams, to celebrity chefs. A lot of the people who I ended up including in my books later on, uh, said, sure, I'll chat with you. But the difference, and I think this is where it really relates to your podcast was that because the conversation was, I think, grounded in this idea of like, hey, it doesn't always work and life is full of mistakes and failures and setbacks. The conversations were a lot more truthful.

5:28They were a lot more open and honest. And I found myself all of a sudden sitting on insights that I hadn't learned. And I had been in the workforce at that point in time for close to 10 years. I had gone to business school. I had gone to law school. And I was like, wow, this is I've read plenty of business books, but I'm like, wow, this is new stuff. And really, if I had to sort of, you know, sort of think about what was it that I was sort of discovering, it was it was really this. When I was I was really trying to figure out what separates people who end up sort of, you know, being able to build momentum in their lives and in their careers versus those who don't.

6:07And what I kind of realized is that I think there are three words that tend to hold us back from what we want and that we're holding me back. And those three words are, I'm not ready. I'm not, I'm not ready. Right. I'm not, I'm not ready to speak my mind. I'm not ready to run with that idea. I'm not ready to step into that role. And the thing that I realized, here's the biggest sort of twist in my sort of thinking, was that I had been trying to figure out how people who exceed at a very high level get ready to go do what they do. And then I realized that I was asking the wrong question because the truth was that none of them were ready to do what they did.

6:47You know, like that was the thing. Yeah, you're never ready. Yeah. You're never ready. Like three friends from design school were not ready to start Airbnb. Two bagel shop owners were not ready to become Ben and Jerry. Malala Youssef Zai was 11 years old when she started speaking out against the Taliban. She was 11 years old. She wasn't ready. Not ready. Jessica, when you stepped into your role at Netflix, the explosive growth period that you were in, and all the things were changing, plus you were CHRO during COVID, were you ready for any of that? I blacked out. I blacked out. Right, right. No, I was not ready.

7:23Yeah. Yeah, I'm by any means. That answer is right now after after interviewing thousands, thousands of people who I think have excelled in their careers. I have gotten that same answer every single time. There's not one person who has said to me, yeah, no, I was absolutely ready. But if you look at the way that we sort of tend to operate our careers and sort of our moves, we hold us back. We hold ourselves back often from going at the next thing or the thing that we it's really calling to us because we feel like we have to heat at this moment of readiness before we act. And so if I have any call to action that has come out of, you know, being the poster child for failure, followed by 10 years of research of and studying extraordinary people, it's this.

8:08Play the game of now, not the game of someday. the game of someday is the game that most of us play which is that we wait for this idea of readiness in order to take action and the game of now flips that on its head instead of waiting for courage or readiness to take action we take action and we let courage catch up along the way that sounds so scary though but yeah it is but but it was scary for you when you when you when you step into your role it's scary for anybody so and that's and that's the thing is that that that that fear is actually quite normal it's actually part of the game and by the way it's always scariest before you start and that's not my line that's stephen king it's scariest and so and so that's the only antidote to that fear to that level of scariness is actually the action itself and that's sort of the mind twist because it doesn't quite add up you're looking to plan you're looking for skill you're looking for all these things that will sort of quell the fear and and make it go away so that you can take action and as it turns out the only thing that's going to take away the fear the only thing that's going to undo the fear is the very action itself yes so conceptually that all makes sense so but let's like yeah just take an action but let's talk about these extraordinary people that you studied and that you researched what what was it in terms of action that they were doing, you know, because I think about, you know, even my, my career, just, just like you, like, I don't even know.

9:42It's all by mistake. I don't even know how it happened. Right. But, but I, you know, I just, I didn't even like advocate for myself probably ever. I just worked hard and like kept my head down and did a good job. And then, and this is, I've mentioned this on the podcast before. It's partly my parents' fault because they were like, just work hard, just work hard. Don't ask for anything. And so I did that. And I think I got lucky too, you know, I don't know. But I, and I wouldn't, I don't want to put myself in like a category of being extraordinary, but I got, I got a lot of opportunities that a lot of people don't have the opportunity to get.

10:26Right. So I'm just curious with these extraordinary people, what were the commonalities of the actions that they were taking or what were what were they doing well i think it's a lot of yes i think it's a lot of mentioned hard work i think is an essential part of it and i think grit is a part of it and one of my favorite sort of i think topics that i think i didn't understand very well is that managing your energy is a big part of it as well because the game of now and taking these actions they do take effort they do take energy and it It does require adaptability as well, because when you take an action, it doesn't mean that you know what the rest of the roadmap is going to look like.

11:05And so one of the sort of one of the principles of playing the game of now in your life is to know that you don't have to know the last step in order to take the first step. But as soon as you take that first step, you know, things will start to emerge. And then you take the step after that and the step after that. And that's adaptability. And so that's a big part of it. And managing your energy along the way is another part of it as well. But I would say that, you know, I feel like you're probably being maybe a little bit too humble because I think that, you know, you probably, I know you worked hard, but there were also probably moments where you raised your hand or at least when people said, Hey, Jessica, are you ready for this?

11:46Even if you, I mean, I did, I was like, yes, you were like, yes. And maybe, and then maybe inside, I did not believe I was, but I, yeah, I wanted that job or I wanted, you know, whatever. Yeah. Yeah. And so, and so you take, you take the plunge and you let sort of all the stuff that you feel like is missing catch up along the way. And it, and it, and it, and it does. And I think that this is like you said, I think that this is scary for people, right? It really, it really is. But at the same time, it's also very exciting for people, you know, professor. Extraordinary people. Were they, did you see a lot of fear with them in what you researched?

12:21Really? Yeah, no, totally. That's, I think, the thing that sort of surprised me the most is I think what I saw them as in the beginning was fearless. And what I saw them as in the end was courageous. And courageous is different than fearless. You know, when we think about sort of that, what are the necessary ingredients for courage? You know, it's a lot of what we're talking about, but it's also fear. You actually need to have fear in order to be courageous. Otherwise, there's nothing that you were overcoming, right? Yeah, that's true. I was just thinking about, you know, I was always fearful.

13:01And I think failure was one of the things I was most fearful of. I did not want to fail. And also, I was very competitive. I didn't want to not win. Yeah. Yeah. And, and, and uncertainty, you know, the big part of it as well. Right. So I think a fear of failure was the obvious one for me, but the lack of certainty and how paralyzing that can be as well. So if I don't have a step by step map on how everything is going to work out, maybe I don't decide to take that first move until I figure out what the map is going to look like. And look, I think that's a reasonable way to think. It's just that it's very hard to draw a map these days, right?

13:47Because things are changing so quickly. So quickly. And way, way faster today than they were even five years ago, right? With AI refashioning the way that we do things, the geopolitical climate, the way that skill, like the skills that we need today are going to be different than the skills we need tomorrow. There's so many different ways that sort of that the chessboard keeps moving. And so the idea of being able to sort of plot your moves, I think, is becoming less reasonable. And I know I know you see this when I when I talk to you, one of the biggest things I hear now is that we used to have these three to five year plans that have now turned into six to 12 month plans.

14:23And even those are right. And even those even though I know I always hated the five year plan. I'm like, how do you have a five year plan? Like three years is even a push. Like, you know, like I don't even want to have it happen tomorrow, you know, like, especially if you're in like a high scaling business, it's really hard to predict what's going to happen a year from now. Yeah. Yeah, exactly. And especially if you're disrupting and, you know, you're sort of making it up as you go along. Wow. And I think that's a really interesting point, because as we start to kind of figure out these things along the way, that can be exhausting for people.

15:02I think that there's a real, like, there's, you know, we're in an exhaustion epidemic right now, right? I mean, 70 % of the workforce says they're exhausted. And we're also at a period of very, very high uncertainty. And I think those two are related, right? And so we know how to manage our time. I think most of us, I think most of the people who are listening to this have some type of time management tool. They've probably read an article or a book on time management or learned it in school. We don't know how to manage our energy. And one of the things that I've realized is that when we look at high performing, high momentum teams and leaders versus those who tend to sort of not reach their potential, the ones that don't reach their potential very rarely do, I think they run out of time.

15:45But I think they often run out of energy. They simply don't have enough. What's a good example? Tell us an example. Yeah. I mean, even when I was, so you're working in venture capital right now. I spent a year working inside Kleiner Perkins. And we would look at these startups that were sort of at the kind of borderline. Like they hadn't broken out. So they had not found product market fit. And we would look at two types of runway. One was their financial runway. But the second question that we would ask that was a little less measurable, but equally important was what's their emotional runway right now?

16:21You know, like literally how much energy do they have? Do we feel like the founders are getting tired? Do we feel like the team is sort of, we feel like they're still vitalized to be able to go out and do what they need to go do. And the mistake that I think investors, I think startup entrepreneurs, I think teams and leaders sometimes make is they pay attention to sort of, quote unquote, man hours, or they pay attention to, are we financially resourced? But you can have those things. And if the team is exhausted, then they don't perform at their level. And I hear this all the time. We've got the resources.

16:59We've got the time. The board is on board. all the stuff that we sort of need. But if the people are tired, then you're not operating at a capacity in which you need in order to go succeed. But it's a little bit sort of, I think, frustrating sometimes for leaders because it's like, I know how to manage time. That's something I can do. And I know how to manage a plan, at least as far as I can see. But I don't necessarily know how to manage my energy. And I don't necessarily know how to manage the energy of the people around me. Right. And that's what it's. Yes. I love this. So we're going to get back to like, how do you actually do that?

17:35Because I know that I know you have some, some tips, but I want to get back to your story for a second because we got off track. So you kind of stopped it. Like you started calling these extraordinary people and emailing them and they started talking to you. Then you started doing this research. Well, then I started to write. Writing is something that I started my career as a speechwriter. Yeah, I don't know if I knew that. Yeah, yeah. So my first ever job was in President Clinton's White House as an intern, and that turned into a job. How fun was that? Oh, it was fun. I mean, but it was a very strange time.

18:14This was 1998, dating myself. Did you have to write any speeches around the Monica issue? No, I didn't. But all that happened. But all that was happening. So by happening, I mean, you know, she was an intern in 1995. I came three years later, but the whole sort of the story. Yeah. Yeah. 1998. And so I was there when that was all happening, which was a was a while. It was a while. It was a while time. But looking at what's happening today, it was almost like that was a that was kind of a walk in the park. I know.

19:17very good at it. And I also sort of had this thirst for writing that I just never got back to until many years later. You know, I'd started a company called Rise. It was the first company that I ever built that worked. And we ended up selling it in a successful exit. It was one-on-one health coaching right over your mobile phone. I started the company because of my dad. You know, my dad, when he was right around my age, had an emergency triple bypass surgery. It was one of those situations where I literally, you know, I was like, you know, a kid, he dropped me off to school and he said, Hey, I've got this routine medical appointment and I'm going to pick you up after school right here by the flagpole and a school bell rings.

19:55And I go out there and he's not there. And the reason he's not is because right in the middle of the medical appointment, he collapsed, he had a heart attack and we were so lucky. He was at a medical appointment already in a hospital. He's already in a hospital. So they were able to take him right to the OR. emergency bypass surgery and saved his life and he was very young he was in his 40s he ended up turning his entire life around learned how to eat, learned how to exercise learned how to get a good night's sleep and you know it's been over 30 years at that time I remember doctors being like if he doesn't change his life he's got maybe another 10 years to live and it's been over 30 and I talked to him yesterday and he and my mom had just taken a two mile walk.

20:44So, uh, so amazing. It's amazing. And he had the help of doctors, he had the help of nurses and, and I wanted to make that type of care more affordable for, for people. So I started this company called rise, which is one-on-one health coaching right over your mobile phone. And, and when we were bought by a company called one medical that expanded into, to being able to connect with the PCP or connect with the nurse or even connect to mental health professional through these micro interactions. So, you know, we know. Congratulations. Well, thank you. Thanks so much. I'm proud of what we built. And I remember, I actually remember it.

21:20Yeah. Thank you. Yeah. Yeah. Well, you know, part of it was, I get back to your question. I was learning this. I was learning these lessons from these leaders as I was building the company. So, you know, the article on failure came out before that. So I was doing this kind of in parallel, but to help my company. I was like, what am I doing wrong? And how do I apply that to what I'm building now? How do I not make the mistakes I made before? But what I wasn't doing and I started to do was I started to write about it. So as I was learning lessons, I would journal. And then I found that the journal entries were starting to make enough sense that I could submit them as articles.

21:57And I did. I started to submit articles to Fast Company and to Fortune magazine. And some of them got rejected, but some of them got printed. And eventually, you know, enough of those articles were written where I said, you know, hey, maybe this could be a book. And so shortly after we sold the company, I joined the faculty at Harvard Medical School because that kind of was the area. It was the lane that was developing for me, which is the intersection of well-being and leadership and started to deepen that work. And eventually in 2021, I got my first book published. Oh, congratulations. I mean, what a wonderful story.

22:33You go from being like the Google face of failure and then, you know, you become this entrepreneur who is disrupting health and you're writing books and you're studying extraordinary people. I mean, who like to be part of Harvard? I mean, that's sort of. I don't know, a lot of people's dream. Yeah. Well, yeah. And I'm here to tell you, like, and I know it sounds cliche sometimes, but it's just true, which is like. These, these, these failures can be your stepping stones. They really can. And, and, and the, and the, but the catch is that you got to learn from it, you know, because I, I do, I do know people who are sort of failing over and over again, but they're not necessarily taking the time to reflect and learn, you know, and for me, it just, what it did is it just opened up this field of learning, you know, and that day, that is my world.

23:29time. I like things to be simple. I, you know, I'm a, I'm a dad, I've got two kids. They, you know, we, we are, we are sort of raising a family. My wife works full time. And so for me, like simple is really good and my world is pretty simple. And it's just on one, it's really a loop on one side of the loop is learn. And the other side of the loop is share. And that's what I do day in and day out. I learn from people who I think have been able to learn, been able to experience things in a really sort of, I think, visceral way through their work experience or through their research. I'm constantly learning.

24:04And then as quickly as possible, I'm sharing. And that sharing comes through my books. It comes through articles. It comes through the television show that I host. And I love it. Yeah, you host a television show. Yeah. Talk to us about this television show. Tell the listeners about it. So, okay, here's the funny story behind it. Is that, have you ever watched a show called Schitt's Creek. Yeah, love that show. Okay, alright, so... And every time I talk to somebody who are like, oh, I watch a couple episodes, I'm like, how can you just watch a couple episodes? It's like one of the best shows ever made.

24:41Okay, so Jessica, I'm one of those people who's only watched a couple episodes. I have to go back. I know, I know. I have to go back and really do this, but the son in the show, what's his name? Yeah, yeah, yeah. I don't know why you're making me forget. Yes. Father in real life. So his, he was basically going to host a show. And that show was going to be sponsored by American Express. It was basically like Anthony Bourdain for leadership. And what ended up happening was that they were going to start filming that in March of 2020. So obviously the world shuts down, doesn't happen. And so they indefinitely postponed it.

25:22and one year later they um they go back to say let's go get this thing started and he's not available anymore and so they kind of go back to the drawing board and like all right who's another actor who can play this role of host of this show and so they're you know they're they're throwing out ideas and one day one of the people from the casting agency is at the airport i believe she was at jfk and she sees my book that had just been published in the bookstore and she picks it up she takes it on her flight back to los angeles and on that flight she starts to read this book and this book as it turns out was all about my story which is about going out and meeting with all these leaders and trying to glean their insights and trying to make sense of it and share it out with others and so when she lands she sends an email to her team saying hey like this guy doesn't seem like he has any tv experience but it does seem like he is kind of doing what this host would be doing and so i get a call from the casting agency saying hey would you be willing to do a screen test and so i did yeah yeah of course next thing i know i got i got offered the role that's so cool so that's how it happened yeah i mean how cool okay so the son's name is david rose and it's played by dan levy and that's the father-son combo eugene levy and dan i don't know why it's me anyways they are hilarious yeah so you just get found your book gets read from the airport and then you just get a tv show it's just that easy well i mean yeah i mean other than i just like again rewinding the tape it's like it's like it all okay so so it's funny because one of the things we were talking about the qualities of the game of now right and the one that just struck me for you jessica is openness right do you do you feel like that's been a big part you mentioned hard work but do you feel like openness to new experiences also been yeah i was always open you know okay i'm a big believer that you never know what's around another corner name and that the person that says never you know like okay well i don't know maybe right so you know i um and i also believe that um you can manifest things that you okay i'm so glad you said that because i didn't want to be the one to sort of go woo-woo here but i will go there with you any day.

27:45I think when you have a posture of openness towards the world, these serendipitous opportunities do come to you. But I do think that the more closed off I have been, where it's like, no, no, no, I know the path here. I know exactly what steps I'm going to be taking. That's when the serendipity started to go away. So getting back to your point of like, oh, hey, all of a sudden somebody picked up a book and you got a TV show. Yes, that is true. And it is a funny story, But my posture towards the world had completely opened up at that point in time. You know, I had sort of a sense of what it is I enjoy doing.

28:22I knew I wanted to learn things. I knew I wanted to share them. I knew that I love to write. I knew I love to tell stories. But I no longer had this rigid plan of how all of that was going to take place. I was starting to open up. And the more that I opened up, the more these sort of surprising, beautiful things really just started to show up. Isn't it? I'm just thinking back on, you know, my life in general. And I think that's so true. It's like when you are open and you're curious, I think. Curious. And it is sort of serendipitous how things just kind of come right to you. And times where I've not been that way, things happen, you know.