May 12, 2021

Suneel Gupta | The Surprising Truth About What Makes People Take a Chance on You

Suneel Gupta | The Surprising Truth About What Makes People Take a Chance on You

Suneel Gupta knows the secret behind what it is that makes people believe in you and your ideas. It's not about your charisma, who you know or where you went to school. Persuading others to take a chance on you is something you can learn and Sunee...

Suneel Gupta knows the secret behind what it is that makes people believe in you and your ideas. It's not about your charisma, who you know or where you went to school. Persuading others to take a chance on you is something you can learn and Suneel is about to teach you how.  


Suneel Gupta is the author of Backable, available now on his website |


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Suneel Gupta: The book that tells this great story to his disciples about, about a guy who is, you know, comes to a river. The river is very choppy. He cannot cross it. If he swims across , temps is from across it, he's going to die. So he spends months building a raft, right. Building a robust enough raft that will get him across the river.

And so he finally does, he builds, this really heavy, robust raft gets across the river, gets to the other side. And then the, the, the sort of almost parable or the riddle that, that puts to his disciples. It's like, okay, so now he's got this raft, but he knows the rest of his destination is on foot.

So what does he do? Does he leave the raft or does he pick this wrapped up and carry it on his head? And the disciples are all like, well, of course he leaves the rat behind. He doesn't need it anymore. And the book this whole point is yeah. But the way we live our lives is we all have the, a lot of them have this raft that we, that we've sort of built.

And now we feel like we need to carry it with us. And that raft doesn't necessarily need to represent. Bad things. It can, I mean, abusive relationships, you know, past situations where we felt really hurt and we just have a really tough time letting go. But oftentimes that raft and represent good things, you can represent a lot of grief and represent, you know, a success that we feel like now we have to build on top of that or that in some ways that linearly needs to connect to whatever we do next.

But in a lot of ways, what it's doing is, is shackling us down

Srini Rao: I'm Srini Rao. And this is the unmistakable creative podcast where you get a window into the stories and insights of the most innovative and creative minds who started movements, built thriving businesses, written

Suneel Gupta: best-selling books,

Srini Rao: and created insanely interesting art for more check out our 500 episode

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So Neil, welcome to the unmistakable. Creative. Thanks so much for taking the time to join us. It's

Suneel Gupta: great to be here. Thanks so much for that. Yeah, it is

Srini Rao: my pleasure to have you here. So I actually contacted you because I came across your book, backable, the surprising truth behind what makes people take a chance on you.

And I remember very distinctly seeing it on Amazon when it was ready for pre-order and was like, what the hell is this thing going to be available? And then I saw Neil Strauss put out a tweet about it and I bought it right away. And I think I tore through it and like maybe two less than two days. And I emailed you right away and said, you know, you have to come talk to our audience.

This is about more than venture capital. Like creatives need to hear this, but before we get into all of that I want to start by asking what I think is a very relevant question. Those, what did your parents do for work and how did that end up shaping and influencing the choices that you have made throughout your life and your career?

Suneel Gupta: Yeah. Yeah. So both my parents are in. They, they, they both worked at Ford motor company for over 35 years. My mom is really in a lot of ways, one of the foundational stories of why I decided to write backable. And I think in a lot of ways, just kind of what's defined, you know, her path is very much defined our career.

But when I say are my brother and my brother Sanjay and me, you know she grew up in a at a refugee camp run to the border of Pakistan, India. And she had this really unlikely dream, which is that she wanted to be an engineer with forward. And, you know, she read Henry Ford's biography and said, that's what I want to go do that.

And people laughed at her, but her parents got behind the dream. They saved every penny they had and got her on a boat. Or she came to the United States. She got a, she got a scholarship to Oklahoma state university. The day after she graduates, she heads to Detroit, Michigan to apply for her dream job.

So she gets into this room with a hiring manager and this guy looks at her resume and he says, wait a second, are you applying for the job of an engineer? And she says, yeah. And he says, well, you know, look, we actually don't have any female engineers working here right now because either was the 1960s and Ford motor company was in his heyday doing really well, thousands upon thousands of engineers on staff, but not a single one of them was a woman.

So she's, you know, deflated ridiculous projected in this moment. She gets up, she grabs her resume and except for a purse. And she's about to walk out of the room. And then in this last ditch effort, she turns around and she looks this hiring manager in the eyes and she tells them her story of all the struggle that she had to go through to get to this, this very room.

And then, and then she summons up all the courage she can, and she says, look, things are changing. And if you don't have any female engineers on staff, then do yourself a favor and hire me now. And so that's how in 1967, now , my mom becomes Ford motor company's first female engineer. Wow.

Srini Rao: So what the numerous questions come from?

Just that story alone. What is it that causes a person in a moment like that to turn around the way that your mom did versus the one who just walks out and accepts their fate? Like, what do you think is the difference between those two people? Yeah.

Suneel Gupta: Yeah. It's a great question. I, and I, and I asked my mom that all the time, you know, I think one thing that, you know, she has probably taught me more than anything else is that, you know, it's not, it's not that she wasn't stared in those moments, or if I talked to her about her full journey, right.

Like, I, I, somehow when I was young, I almost had this image of her as somebody who was just courageous by nature. Like that's what it was courage that led to. But what I realized over time and talking to her, and now, now that I'm older, it really understanding or edit to get deeper level. What I realized is that it was the reverse, it was action that led to courage.

She was just taking these moves. She was just taking these steps and then, and then just kind of letting courage sort of follow up. So there were all these moments that she was in her dorm room afraid because you know, she hadn't seen her family in years and can be, or communicated with them in any way, shape or form that, you know, they, they didn't have a phone back in their village.

So it was just literally just letters, many of which would never arrive. And, you know, those were, those were frightening moments. And so I just think that there's this, there's this sense of take action first that the rest catch up later, which to be honest with you, I'm still trying to do, like, I don't feel like I've ever been in a situation where I have felt like I.

I absolutely needed to do that. And the way that she felt like she needed to do this. So for that reason, maybe, you know, the, the, the, the actions that I've taken have been, I've been, I've had the luxury of, of letting courage catch up a little bit before I actually take action. Whereas I think in her case, she just, she didn't have that.


Srini Rao: I mean, so the other thing that I think is really interesting, and I think this is common with Indian immigrants and I slid to see this in my own parents' stories is there's a level of resourcefulness that they seem to just have, you know, innate to them. And Scott Belsky talks about this, you know, in, in a couple of his books where he talks about this sort of distinction between having resources versus resourcefulness.

And he, I remember very distinctly Jessica Livingston in the Paul com the interview book that she did is one of the, she said that one of the things she noticed is the moment founders raise money. They actually become less resourceful because they have an abundance of resources. So I wonder, you know, that sort of resourcefulness, how is that something that you develop in yourself?

Like how do people develop that within themselves? Because I think that that's such an invaluable thing because that's infinite, whereas your resources, no matter how much you have are fine,

Suneel Gupta: Yeah. Yeah. I mean, I, I think, I think I think what you're, what you're saying is super interesting to me because, you know, I noticed you know, when I was working in Silicon valley, we were talking to you and I are both talking about our time you know, out in the bay area.

And you know, when I was, when I was raising money for my first company rise, I mean, I was getting rejected by every investor that I, that I pitched. I was, I was, I was zero for over a dozen. And you know, there was a whole, there's a whole journey that took place where the company ended up moderately successful.

But what I was fascinated by was after I had sold the company, he same, a lot of the same investors who had, who had rejected me were now saying, Hey, what are you doing now? You know, and, and here, and here's a check and there was one investor who said, look, why don't we just, what do you, what do you, what do you want to do next?

I said, I don't know. I'm not sure. And, and, and the VC literally said, well, why don't we just form like a new co like a holding company right now, we'll fund it right now, off the bat. And then you can change it to whatever you want to. And I thought to myself, like, what is, you're basically saying you're going to fund a non idea, like a non idea.

And, and I, and I thought to myself based on what, like, it's not that I necessarily have like a Bulletproof track record in, in, in any way, shape or form. You know, and what I realized I did camp out inside a couple of DCS. And when I started to realize is that, you know, not only was that probably not the right sort of thing for them to offer me, which I never ended up taking, but like, what else, what happens to, and I'd be interested to hear if you see this as well, Second time founders or repeat founders.

Who've had some sort of success behind them, often underperform. They underperform compared to first-time founders. They certainly underperform compared to second time founders that are coming off of a failure. And I think a lot of it comes back to that resourcefulness that you're talking about or resources versus resourcefulness people who don't have the track record.

People don't have a wind underneath their belt, have to be restored. Versus, you know, the others that already have the resources and maybe just, it maybe just

Srini Rao: kills the hunger. Yeah, no, I definitely see that. Cause I, I remember my, my roommate who was the fifth employee at Yelp, he was telling me he went to work at a couple of other startups.

And there was a guy who came from another really well-known company that I won't mention by name. But he said, you know, the guy basically thought because the first startup was such a success that he had sort of a Midas touch and the next one was just a complete flop.

Suneel Gupta: Yeah. It happens all the time.

Right? Yeah.

Srini Rao: So, I guess, how do you actually prevent ego from getting in the way and resting on your laurels when you've already had a success? Cause I think this is something that I see with writers too. Right? So you can look at this sort of a Ryan holiday is a great example of somebody who really maintains a good, does a good job doing this because he said to me, once that, you know, what the editor wants told him was a success gives you the conditional opportunity to try again.

And that always stayed with me. And now Curie are eight, nine books later with Ryan and he's always working on the next book. Like he's never resting on his laurels. So how do you prevent that from happening when you've had a success? Because people tend to get confident, which is great, but they can also get overconfident.

Suneel Gupta: Yeah, yeah, yeah. I, I guess there's a difference between, you know, being competent in. Your process versus being confident in the outcome. Right? Like when I, when I now have I'm working on my second book now and, and, and what I, what I am confident about is like, I think I know how to write, and I think I'm, I'm familiar with how to write a book, you know, I know, I know, I know how to sit down in the mornings.

I know how to do deep work in a way that I didn't before I know how to keep banging my head against the desk, even though you know, nothing's coming out really like of use I know the importance of throwaway work, right? I, I, I remember I remember having a conversation with Selma and rusty.

When I was in law school, he was passing through town. He's one of my favorite authors and I asked him you know, what. You know, what inspires you to write? How do you get inspired every day to write? And it was like the worst. It was, it was like the worst possible question that I could have asked him because I mean, it just, it showed to him immediately, like, this is clearly not, not a writer or anybody who's trying to like go through the writing process because he's like, you know, I don't, I don't get inspired to write.

I, I sit down at my desk every day, just like anybody who's, you know, committed to their work. And I just write, I write he's like, I almost had like the, you know, in terms of hours, I almost, I almost seem like an accountant more than anything else. Like sit down at nine, I write for about eight hours until five o'clock and he's like, he's like the vast majority of what I write is unused.

It goes in the trash bin, but like every day there's like a Pearl, right? There's a Pearl, there's something that's usable. And what I do for a living is I take these little pearls and I string them together into paragraphs and eventually chapters and eventually books. That's what I do for a living.

Srini Rao: Yeah.

I mean, the reason I laugh is because I, I write a thousand words a day religiously. Like it's just something I've done for the better part of the last eight or nine years. I've written two books. And to your point, like you learn how to write a book. You don't necessarily learn how to write a bestseller.

But I, the reason I'm laughing is because I remember meeting some girl at a party once and she's tells me she'd been working on a book for five years and she looks at me and says, well, you can't just sit down and write. And for my friends who worked with me, he said, dude, you're the wrong person to say that.

And I literally looked at her, was. Yeah, that is the biggest bunch of bullshit I've ever heard, which is not a polite thing to say to somebody you've just met. So needless to say, I didn't rub her the right way, but it was fascinating, but you know, we looked at that, but let's actually, and go

Suneel Gupta: back, but I'm curious about that real quick though.

So you sit down and you said you write a thousand words every day. Yeah. And does that, is that take you just different amounts of time? Is it, or is

Srini Rao: it varies? I mean, there are days. Well, it depends on, you know, whether I can get into a flow, like if I'm doing deep work, if I'm not distracted some days I can do it in 30 minutes and I'll produce golden 30 minutes.

Other days I'll do it for an hour and a half and have nothing but garbage. Like I, I, the way I describe it as you're shoveling a mountain of shit for announcer

Suneel Gupta: gold. Yeah. Yeah. That's totally true. That's of, but I am fascinated because I, I T I, I have heard people saying, look, three hours, no matter what, or two hours, no matter what, but I liked the idea of like a thousand words, no matter what cause it does.

I think the whole.

Srini Rao: Well, Julian Smith was the one who turned me on to that idea. And Julian Smith had one of the most popular blogs on the internet when he told me about that. And I thought, okay, you know what? He's written two sellers. And he is one of the most popular blogs on the internet. I will do that.

And within six months of starting that, I ended up self publishing, a wall street journal bestseller. So when you get a result like that from a behavior, you kind of were like, okay, I'm never going to stop doing this.

Suneel Gupta: Do you ever do that? Or there are times just to fulfill the quota that you're just like, just continuously run the street and fuck

Srini Rao: it.

Doesn't get that bad. But a lot of it is just incoherent, psychobabble. It's exactly the way Rushdie described it to you, right? So you might write 800 words and one sentence might end up being the title of a blog post. And the next day you build on that and you suddenly have a lot more.

Suneel Gupta: That's a good question too.

Like I, I, I do you, do you leave yourself prompts to just get guns? So

Srini Rao: I don't read myself prompts, but what I do is I read for anywhere between 45 minutes to an hour before. So for example, if I'm reading your book, I'll take a quote from the book and that quote will be my prompt. And I, this is, you know, psychology for anybody who wants to know.

I learned this from Shawn ACOR, his book, the happiness advantage of all places. So there's a concept called success accelerant and where he talks about the fact that your brain makes progress towards a goal based on the perceived distance to that goal. And what happens when you use somebody else's quote, is it shortens that perceived distance?

So you're able to get some momentum going. Mm Hmm. And if you're reading, you're kind of making connections in your head and, you know, connecting dots and all that.

Suneel Gupta: Yeah, no, that, that that's that's fully right. Is there, are there, are there books that you kind of go to as like, you know, just, I mean, are you always reading new stuff or is there a book you kind of go to for,

Srini Rao: but there's definitely, there's definitely a few that I keep on get on the shelf, like at all times, and I'm looking at it right now, pretty much anything by 50 cent and Robert Greene Ryan holiday books, anything by Seth Goden Cal Newport stuff.

And then, you know, a few sort of life philosophy books. I don't even remember them. I, you know, I read the wealth of nations recently. Steven Pressfield, it's just kind of I think really what it is is it's kind of what I always describe it. I always say like, trying to write without reading is like trying to cook without any ingredients.


Suneel Gupta: yeah, no, it's so true. By the way Pressfield I've gotten, I mean, I've always admired his work. Like I love, I love the war of art we're on art or of art. But, but what I didn't realize is how connected. The legend of bagger Vance was to the Bhagavad Gita. Yeah. I remember that. I remember, I remember watching the movie and just, I mean, honestly not, not liking it all that much.

And then, and then someone told me that like the book is so much better and also just deeply connected to the Gita. And I'm like, no, no way. And I, and I went and read recently and it was like, it blew my mind. Have you read it?

Srini Rao: I, you don't want to adopt the legend of bagger Vance, but I actually did read the Gita and I read a bunch of books related to it.

It turns out the, the the lion king is also based loosely on the Bhagavad Gita and like some of the themes and none of them. The fun facts. Well, let's, let's get back to your growing up because I, you know, this is something I always have to ask. People are raised by immigrants, particularly Indian immigrants, because, you know, we haven't had a similar upbringing.

What was the narrative about careers around your house? I mean, you became a lawyer, obviously. So was it, Hey doctor, lawyer engineer, or did you actually get, you know, advice to go and do something different?

Suneel Gupta: I think it w I mean, it definitely was around lawyer doctor engineer, for sure. But there was always sort of a sense of I guess in my house, it was always because of my mom's story, a sense of like, it could be that and something else, like, it could be like, you know, go, go make your mark somehow.

Right. And don't, and don't, don't feel like you need to follow the norm. You know, like I, I have, so my older brothers is, is 10 and a half years older than me. And so you know, Sunday was a practicing physician in suburban Michigan when I was going to college and he knew was very good he's so, you know, his surgeon, he, he, you know, had gone on a great program and, and, you know, got, got a great role.

And he was inherently, I think just unhappy. I mean, unhappy with the idea of like, this is going to be it, this is what I'm going to be doing. And he was, he was very interested in the idea of like healthcare and news. And he was interested in the idea that you could tell stories in a way that was just, you know, much broader than what you was doing everyday inside, like the waiting rooms.

And so you know, I still remember one day he comes back to the house and we were all having breakfast and he's like, I wanna, I wanna go see if I can apply for a job at. Right. Zero on our experience, zero journalism experience, but he's like, I, I, this is what I want to die. This is something that I would like to do.

And I remember thinking to myself like, oh, how are my parents really gonna react to this? And, and I, and I think my dad was a little less, like he was, he was a little more uneasy about the whole thing, but my mom was like, go do it. Just, yeah, go, go, go, go give it a shot. And and, and, and not only that, like, it was like, I'm now going to hold you accountable for giving that a shot.

You just shared something with me. And now like, you're, you're like, I'm going to be on you about this. And so he does, and he becomes CNN's first chief medical correspondent, Dr. Sanjay Gupta. And so I, I don't, I think that that, that kind of mentality was sort of, I think you know, I think welcomed in our house more so maybe than I think some of my friends who grew up in, you know, immigrant households, which is like, stay the lane, stay.

Srini Rao: Totally. So I guess on that note, you know, a lot of parents are listening to this based on how your parents raised you. What would you tell parents who are listening to this about their own children? I mean, you're a father to, you mentioned, so like, you know, how has that impacted the way you're raising your kids?

Suneel Gupta: Yeah. I mean, you know, I, I play a little game with my daughters every, every, every morning we've been doing this really ever since the pandemic began and they're both like, you know, sort of homeschool. And so I, I asked them and one's eight and one's four. And I asked them, what is the meaning of life? And they say to me, and they say to me to find your gift.

And I say, what is the purpose of life? And they say to give it a. And it's all based on a quote from Picasso. One of my favorite quotes, but I love playing this whole book back and forth with them. You know, my father had, has had a headache emergency triple bypass surgery when he was not much older than me.

And, you know, it was like a knee caught it in the Nick of time and had we not, like, I just don't know. I mean, I don't think he would, he would be here with us right now. And so I think about that because like, what are you, especially now, like, you know, you can't take anything for granted, what do you want to leave them with?

And for me, it's like the answers to those two questions are the, are, is a very important thing for me to leave them with. I think when it comes to giving our gift away both finding our gift and giving it away I think that the advice that I try to give myself and try to stay true to is like, it's very tempting to want to give them.

Right. It's very, very tempting to want to say, if you do this, then you will get this from there you go. There, here are the steps. And here's what the first step looks like. And here's what the last step looks like. And instead I've tried to, you know, do what, what, what are, what are good common friend chase Jarvis says was to trade that trade that map in for a compass, right?

To give them, to give them a compass by which they can decide not what the last step is, but what the next right thing is. And I think that's very much a function of not just examining the way the world is, but, but, but being able to like tune into yourself and figure out what it is you want, and also a function of realizing that your last step may influence your next step.

It may inform your next step, but it doesn't have to determine your next.

Srini Rao: I love that. Yeah. I mean, we have this guy, Steven Shapiro here who wrote a book called Gulf free living, which literally flies in the face of everything I'd ever heard in personal development. And he said something that just stayed with me and he said, do you want to choose a direction rather than a destination?

And I thought about that. I was like, wow, that actually opens up so many more possibilities for where you could end up because I, you know, I remember you at Berkeley, you were kite. It was very clear. Like it was just sort of, Hey, here are your majors. Here are the potential career paths that each major leads to.

And I was like, wow. In the span of four years, we've narrowed down the possibilities for our life and to doctor lawyer engineer management consultant. Yes.

Suneel Gupta: Yes. Yes. And, and, and, and, you know, and I think, I think that it's to a certain degree, it's, it's, it's fine because you have to, you have to choose something at that at that age.

I think that like we are, you know, we, we, we are sort of in a position where we were asked to choose something. I think the tricky thing becomes, or at least where I've seen the real pain set in is when you then get five to 10 years down the line and you feel like what you've done in the past. You know, predetermined what you have to do in the future.

I mean, I I'm, you know, I, I I'm, I'm about 10 years out of law school. Now I went to my 10th year reunion and I, and I met some former classmates who, who seem perfectly happy with what they were doing, but I also met some who seem perfectly miserable with what they were doing. And there was a good friend of mine who, you know, we went and grabbed drinks afterwards and I was talking to him and he's like, man, I'm just not happy.

And I'm like, well, why don't you do something else? And it was one of these uncomfortable conversations where he's like, you know, I could just tell that he felt very anchored, almost shackled by the decision that he made when he was 23 years old to go get a law degree. Right. And now that decision is driving an influence is it's not just influencing, but it's been shackling what he's doing now, you know, in his, in his thirties.

And so I, you know, the book that tells, this, told this great story to his disciples about about a guy who. Is, you know, it comes to a river. The river is very choppy. He cannot cross it. If he swims across attempts to swim across it, he's going to die. So he spends months building a raft, right. Building a robust enough raft that will get him across the river.

And so he finally does. He builds those really heavy, robust raft gets across the river, gets to the other side. And then the, the, the sort of almost parable or the riddle that, that puts to his disciples is like, okay, so now he's got this raft, but he knows the rest of his destination is on foot. So what does he do?

Does he leave the raft or does he pick this wrapped up and carry it on his head? And the disciples are all like, well, of course he leaves the wrap behind. He doesn't need it anymore. And the book this whole point is that the way we live our lives is we all have the, a lot of them have this raft that we, that we've sort of built.

And now we feel like we need to carry it with us. And that raft doesn't necessarily need to represent. Bad things. It can, I mean, abusive relationships, you know, past situations where we felt really hurt and we just have a really tough time letting go. But oftentimes that raft and represent good things, it can represent a lot of grief and represent, you know, a success that we feel like now we have to build on top of that or that in some ways that linearly needs to connect to whatever we do next.

But in a lot of ways, what it's doing is just shackling the. Yeah.

Srini Rao: So I want to start talking about the book, but I have one other question. And this is about you and your brother. So 10 year, age gap, older brother, I'm the older sibling. And I feel like in any immigrant family, the older sibling is the experiment.

The second one is the one where parents fix everything. They fucked up on the first one and the younger one gets away with murder in comparison. So what I wonder is, was there any contrast in terms of the type of advice your parents gave each of you about making your way in the world? Because like, you're talking about 10 years later, your parents have had the experience of raising one kid.

So they've dealt with all this stupid bullshit, like teenagers do like, Hey, I need expensive shoes and nice clothes to fit in at school. So I wonder, like, what was the contrast, like in terms of, of, you know, your experiences when you were younger?

Suneel Gupta: Yeah, yeah, no, I mean, I think, I think I certainly had it much easier.

Certainly had a much easier than my brother. I think that like we, all, my parents were both you know I think it, you know, the immigrant story is, is an experiment, right? It's like, is this thing gonna work? You know, is this thing that we, that we sort of set out to do probably against the wishes of a lot of people who are sort of in our circles back home.

Is it going to work. And, and I think that there was a tremendous amount of pressure on Sunday to sort of make the answer to that. The yes. And by the time that I came along, you know, by the time that like, you know, I was in, I don't know, third, fourth grade where my parents were actually starting to pay attention to how I'm doing in school.

Like Sanjay was already like doing very, very well. Like he was, you know, he ended up being about tutorial at school. So I think it's certain to a certain degree, it sort of took the pressure off of me. And you know, I was not, I was definitely not as high performer, you know, academically as, as Sunday.

And I think that that always sort of like, you know, that always irked my parents, but I think there was also sort of. Well, the center is doing well and you know, and I, and I also, I think, you know, it's, it's Andre being 10 years older than me. He is like a third parent. So I always sort of had that, you know, where I had somebody who grew up here, who grew up in my situation, who I could turn to for advice.

Whereas he didn't really have that.

Srini Rao: Yeah. Yeah. Well, I even, it's funny because my sister got like astronomically better grades than I did at Berkeley. And I was like, yeah, that's because I taught her how to pat her GPA the first semester, like, because I screwed that up royally. But yeah, I mean, I, I remember very distinctly in high school, I had a friend whose mother told them, if you want me to go to my grave in peace, you'll become a doctor.

When I told my mom that she was actually thrilled about it and she more or less she'll deny this to the day she dies. But she told me once, if you don't become a doctor, I won't pay for you to go to college. My dad was like, look, you're going to get there and you do whatever the hell you want. Just tell her you'll become a doctor for now.

So, but you know, I joke with my sister at least satisfied our family quota for becoming a doctor. We need to at least, you know, every Indian family needs one.

Suneel Gupta: Totally.

Srini Rao: Well, so what has been the trajectory that led you from law school to startups,

Suneel Gupta: to writing backable? Yeah, when I was finishing up law school, I met, I met my now wife.

We were dating and the plan, the plan was pretty laid out for us. We were going to go, you know, w we were at, I was at Northwestern. So she, she was she was at the journalism program and we both had, we both had offers at, you know, from places in New York, she was going to go work at, she's going to go work at a you know, on air.

And, and I was going to go work at a big corporate law firm. And and at the last sort of, you know, a couple months before graduation, I basically had a panic attack about the whole plan. I said, you know, something's off here. I just, I don't feel like I'm going to be happy, practicing law. Like I have.

Feeling in my gut and or at least not going to like a big corporate law firm. And so I started to started to make trips out to Silicon valley. And I said, at this point in time, this is in 2008 and I was working on the Obama campaign. And you know, I I've worked in politics. My, for one of my first jobs out of, out of college four years before was working for the democratic national committee.

And I was backstage in 2004. When Barack Obama gave his big speech, his, his first big speech. And I saw, well, it seemed like the world was watching him. I was watching the world because I was, I was, I got this sort of backstage view and I watched this like tidal wave of energy ripped through the crowd.

And I thought to myself, I want to go, I want to go be on whatever that guy is doing next. I want to be a part of it. And that, that was in large part why I ended up in Chicago. And so I kind of use this idea that I was, I was working in politics to connect with other people who were excited about. This intersection of tech and politics.

And one of those people was read often. And, and I, and I, and I threw a few introductions. Finally got my way into a meeting with him where I, I, you know, I said to him, look, I don't want to go practice law. He's like, I don't, I don't, I don't blame you. And, and I said, I'd love to come out here and do whatever I'll, you know, tweak floors.

If I need to. Now at that time he was, he was working at most. I mean, he was, he was, he'd founded LinkedIn, but he was a chairman of Mozilla. And he's like, you know, I think based on sort of your political interests and your interest in tech, this might be a really cool place for you. And so I started to, yeah, I went and visited Mozilla and what I found was like a group of just active.

Programmers like people with this, just almost Renegade sort of attitude about like, Hey, we can change the world, even though we're completely understaffed over here. Even though we're a nonprofit, we can go head to head with companies like Microsoft. And, and I love that it was intoxicating to me. And so I begged them for a job.

And I ended up, I ended up landing something and it was, it was sort of on the legal, it was, it was skewed towards the legal side of the company. And at that point we had one lawyer in house and the idea was I would help him out. But I found myself just spending all my time on the other side of the small building, which was with the designers and engineers, like asking them what they were up to and asking questions.

And eventually that sort of led to me helping out with a feature that we, that we shipped and someone said, Hey, you know, maybe product management is your thing. And and so I took on another feature and I shipped that and eventually I just became a product manager inside and that's how I cut my.

Srini Rao: Wow. So I love the fact that you took the sort of lateral move. So a couple of questions come through about one. What parts of your legal background were you able to apply to being a product manager? Because I think people often tend to write off their skills. Cause I saw this with a woman in one of our coaching programs.

And when she told me she was like the, the marketing director for the American and working associate, I was like, wait a minute, you probably know more about marketing than all of us here. And we're teaching you, you should be teaching a workshop to us on this. But I think people often discount skills from their past because they think they're useless.

Yeah. So one, you know, how do people take inventory of, you know, tangible skills that are relevant to what they're doing, even though they might not realize? Cause it seems like that's exactly what you did.

Suneel Gupta: Yeah. You know, it's, it's a really good question. And I certainly do, and I certainly apply things that I learned in the past, even though I'm not, I didn't, they weren't, they weren't required.

They weren't sort of like, you know, to be a product manager at Mozilla, there was nowhere in the job description that you need to have a law degree. But, but, but you know you know, one, one thing that I learned in law school, I still remember I wrote a paper and it was my first year and I handed it into my professor and I got like, it was just, I got, it was returned to me and like ton of red ink, you know, I, it was, it was basically like I failed, I failed the assignment and I, and I thought I had, I'd argued sort of for my client, which is what the, the assignment, I thought it argued for my client very, very well.

It's like, what, what is going on? What what's, what's the meaning of all this? And I, and I went and asked her and she's like, yeah, but she did not argue the other side. You did not point out what the other side was, was likely going to say and what your answers to that word. This is basically 50% complete.

You've only thought you've only talked about like, why you're right. But you haven't talked about the arguments that other people are going to sort of pull out. And that was a very, very important lesson for me because it ultimately ended up being something that was really important for the book as well.

In the book, we talk about this idea of steering into objections, steering into the objections of your own idea. And I was in law school that I really learned that, which is like, you know, you can get really, really excited about your own point of view. And, and this is especially true for product management.

You excited about a featuring, et cetera, about an idea. You said about something that's creative, but to be able to take that hat off and put on the critical. And then think through, all right, objectively here, what are the, what are the top three reasons why people are going to think this is wrong? What are the top three reasons?

People aren't going to think this is, this is something worth investing in. And then, and then, and then answering those is how you actually get ready for a room. You know, it could be how you get ready for a courtroom, but it could also be how you get ready to rally your team around an idea on a zoom conversation is you can proactively yourself steer directly into those objections.

And then talk about what the answers to those objections.

Srini Rao: Yeah, well, let's, let's get into the concepts in the book and I, yeah, I think I emailed you and I told you right at the beginning, you know why I liked the book so much was because I felt like it was so relevant to my own story. I went from being the guy who got fired from every job to being a guy who raised around a venture funding.

And on my first attempt, which was, you know, a stroke of luck if there ever was one. But you know, so one of the things you say as you look at the opening of the book is that people who change the world around them, aren't just brilliant. They're backable. They have a seemingly mysterious, super power that lies at the intersection of creativity and persuasion.

When backable people express themselves, we feel moved when they share an idea, we take action. What moves people? Isn't charisma, but conviction, backable people earnestly, believe in what they're saying. And they simply let the belief shine through. Whatever style feels most natural. And what that reminded me of was something that Chris Saka said to Tim Ferriss on the Tim Ferriss podcast.

You might remember this, he says this in every speech that he ever give. And he said that when he invests in a founder, the one thing they all have in common is that they believe that their success is inevitable. And so I wonder, you know, and I felt there was a lot of overlap between what you said and, and you know what said there, and I've asked a handful of people this, do you think that that is something that is inherent or something that people can develop that belief that their successes in a battle

Suneel Gupta: inevitable?

I think that is something that can be developed for sure. There's no doubt that certain people just sort of come up with ideas and, and, and, and sort of have this feeling of inevitability and, you know, and I, and I think that, that, like that doesn't. And well, right. And I think, I think that we, I would, I would argue that that some of it ends badly.

I mean, we're, we're, we're thinking about sort of, you know, the fire festival we're thinking about we were right there and like, I think that there are, you know, Elizabeth Holmes talks a lot about conviction, you know, and, and, you know, but, but what's that conviction really based on, I think for those of us that don't have the ability to come up with an idea and have this almost ability to look others in the eyes and say, I hundred percent believe in that.

I think the vast majority is can't do that. The vast majority of people who are high integrity can't do that. And so you develop that conviction and I think you do that in different ways. We talk about a bunch of different ways in the book. I personally, I like to write my ideas. I like to, you know, one of the things we found is that when you, when you look at sort of the way that ideas are shared, even inside big companies and why great ideas, great ideas get killed inside companies, what we found is.

A lot of those ideas don't get killed inside formal conversations. They don't get killed inside conference rooms. You know, they typically get killed inside very casual conversations in the hallways in parking lots. When we tend to sort of blurt out the idea before we're actually ready it, we blurted out before we actually have conviction.

And then what ends up happening is we sort of look around and we don't get the reaction that we're necessarily looking for. And so we kind of dismiss it immediately. We put it in a mental drawer and we sort of walk away and it happens all the time because new ideas are fragile and we tend to be pretty fragile when we have new ideas.

So what backup, what people tend to do is they almost catch themselves in that moment. And they do a little decision tree on like, is this an idea that I have high conviction for, or not? Like one way to think about it is like, is this a peanut M and M or is this a chocolate. I got a peanut M and M you can squeeze on it and it's, it's not a piece of metal, but it's not going to crack immediately was talking.

I'm going to be squeeze it just a little bit. And then it cracks it. If it's a chocolate, M and M, then don't share it in that moment. Right? Like Jerry Seinfeld has, this, has this saying, I think he actually, I think he actually brought it up in the temper show recently. It was just like, don't share that day's material no matter what, right?

No matter what do not share what you wrote that day with anybody, because you don't, it's still very fragile backable. People tend to sort of take this incubation time to put the peanut inside. And again, getting back to like how I personally like to just write out my ideas. I like to like to start freeform writing and I try to follow a couple of ground rules that I've learned from, from, you know, backable people on like, what, what to do when I'm writing this out.

One is that you want to be able to wander. You want to let yourself wander, you know, one way to think about it is like when you're starting to come up with like a new idea, You, well, we want to fall in love with the problem, but you don't necessarily want to fall in love with the solution. Like let yourself wander in different areas.

And I think we get in trouble sometimes and we're like, here's the problem. And I know exactly the answer. And I'm just going to write that out. I'm going to start getting into almost like spec mode or it's like now I'm starting to like really get into the definition of the solution. Well, backup, what people tend to do is they tend to sort of allow themselves to meander and wander knowing that the vast majority of cases they're going to end up in somewhere that's better than, than, than, than where they started.

That's one thing the second is that like, give yourself some sort of end date to that wandering, right? Like give yourself some sort of timeline because we all know people who just like been hanging out, hanging on ideas for for years, and it's very easy to do. So one of the things I like to do is I like to just call a friend and say, Hey, you know, three weeks from now, I want to share an idea with you.

And typically the friend will be like, , what's this all about? And I'll say, you know, I can't share that with you right now, but, but like three weeks now I will promise. And what that, what that, what that gives me is something on my schedule now that I know I just don't have an infinite amount of time.

There's something, somebody I need to share it with. It's low stakes, but at the same time, it's there. But now I have enough time where I can actually start to wander a little bit and get to a place that I feel like it's true.

Srini Rao: Yeah, absolutely. Well, let's talk about the actual pitch process. Cause I think this is one of those things that really struck me and I, I, you know, I realized this was like identical to my entire experience of pitching the investors at pod fund.

You actually talk about your first, well, first off, tell me about your first experience. Pitching a venture capitalists.

Suneel Gupta: Yeah, I mean, well, it wasn't, it wasn't positive. I mean, I, I, I. You know, I'm trying to remember exactly what that first first meeting was, but I can tell you the first set of meetings were just, I mean, it was just awful.

I mean, I, I still remember that, you know, at best, at best the meetings were well, thank you. Thanks for coming in. It was almost like polite nodding and a few sort of questions that I feel like we're almost kind of just like very surface level, but there was one thing I, I got pretty good at, even before I started pitching was actually just gauging whether there was excitement in the room.

Like I that's something that I naturally know how to do. I think it comes from my days, working in working in politics, are people getting excited or not? And I could just tell very much that, that people were not, were not getting excited. And then I would, I would get the, I would get the follow-up email.

Thanks for coming in. And, and, and this, this is not, this is not for us. And that happened over a dozen times in a row.

Srini Rao: Well, so with that in mind, one of the things that you say is you know, I spent almost all of my time working to convince, convince investors in very little time, working to convince myself, reverse that spend 80% of your time convincing yourself, then the remainder pulling together, slides, business plans or whatever else you need to convince a backer.

So when you've been rejected a dozen times, how do you keep convincing yourself?

Suneel Gupta: Yeah, I mean, you know, so for me, I had not spent that time really convincing myself. I, you know, w w one of the things that I think I see founders do, and I certainly did this as well. It's like, I jumped straight from idea mode into presentation mode.

I literally said, wouldn't it be cool if, so the idea that I had was a one-on-one health coaching service. And, you know, so you get, you get matched up with a private, you know, personal nutritionist or whatever your mobile phone, and this is 2009. You had 12. When I came up with the idea 2000 early does 13 when I started sharing this around with investors.

So, you know, pretty early in, in sort of the telemedicine space. And so there wasn't, there wasn't a lot of precedent for what we were doing, but I was excited about the idea, but I wasn't convinced, like I hadn't done the work to really build conviction around the idea. I didn't, you know, I hadn't, I hadn't really taken it out to customers.

I hadn't really sort of figured out how this was going to work the nuts and bolts of it. Yeah. And just, it hadn't done the work to say, you know, I I'm iron clad on like, why I believe this is going to work instead. I kind of shifted from, Hey, like, I can totally see how this will look on a mobile screen.

Let's get some screenshots together. Let's, let's pull together a pretty pitch deck. And so I skipped a step, you know, which is again, like, I, I, I skipped straight from idea. Into presentation mode. I would have been much better off spending 80% of that time that I spent in presentation mode, building slides and getting, getting my narrative together, I would have been much better off than in the 8% really kind of convincing myself like asking myself the tough questions.

Well, why is this it's during into new the objections of like, well, how do you, how do you compete with like a weight Watchers? How do you compete? How do you compete when ad space is so expensive? When you talk about weight loss, things like that, asking questions like that, and coming up with answers to those, even if those answers weren't perfect, Zen then been shifting maybe 20% of my time into yeah.

Creating, you know, some, some, some decent looking slides and then, and then going in and pushing.

Srini Rao: Yeah, it was funny. Cause I remember when I went into pod fund, I, you know, I basically, I was like, this is what I'm going to do with your money. And the thing is everything that I said I was going to do, I'd already done because we'd been around for nine years at that point.

Right. So it was like, we're going to use your money to produce animated shorts. Here's an example. It was like, we're going to do this. Here's another example. And it was kind of, one of my friends said, he's like, you literally have done everything you said you would do

Suneel Gupta: already. Yeah. Yeah. You, so you had extremely high conviction that what you were going to do, the way you were going to use their money was going to work because you already had, you already had done it.

Right. I mean, and, and, and, you know, I think that, that, that, that, that's a, that's a high conviction. That's a high conviction moment for me. I had not, you know, I hadn't, I hadn't built anything. So I, I needed to do, I needed to compliment this with lots of research, with lots of customer discovery, you know, with, with just, we're just getting to the point where I could defend why it was going to work when I don't have evidence that it.


Srini Rao: well, so this actually makes a perfect segue to something else that you mentioned. And I want to spend some time talking about this, cause I think it's one of those subjects that we kind of brushed under the rug, or, you know, we wait for a suicide to talk about it, but you say in the startup world, one of the things we obsess about is financial runway, having enough money in the bank to keep making progress in payroll.

But what we don't talk about is emotional runway and Sam Altman talks about this. He says that managing your psychology is, you know, one of the hardest things about being a founder. So let's talk about this idea of an emotional runway, because I think it's, it's more than just about energy and passion.

It's also a mental health issue. So for example, when you go and tell your wife, Hey, I'm going to go do this thing where I'm not guaranteed an income or I'm not certain, how do you manage that emotionally? Like, because I think it definitely impacts everybody around you.

Suneel Gupta: Yeah, yeah, yeah, absolutely. I mean, I think you're right.

We don't, we don't talk about it enough. And I think that, you know, Th it's it's I think it's a huge discussion. I think one, one of the, one of the first things that I learned is to choose a, to choose a, an idea or choose a project where, you know, no matter what, no matter what the outcome really is win or lose, you're not going to look back on that time and feel like it was a waste because what it, what it was, what it was to you was was was something that just really truly lit you up.

Right. It was something that you felt so strongly about that, you know, of course the outcome matters, but you weren't doing it for the outcome. Yeah. I remember when I was leaving Groupon cause I was at Groupon for the three years before I started my own company. And you know, I w I, I joined Groupon before they had raised their series a and I left after it was a public company.

So I'd seen this insane sort of growth and ups and downs. And, but my whole world was focused on e-commerce and I knew leaving the company that I wanted to go be an entrepreneur, but all of my ideas were focused on e-commerce. I literally like this business school style spreadsheet of ideas. And I remember taking that spreadsheet to a mentor of mine, and she looked at the spreadsheet and then she asked me, okay, which of these ideas actually makes you come alive?

And I looked at the spreadsheet and I realized like, none of them really did. None of them really made me come alive. They made sense. Like from a, from an intellectual business point of view, you know, the, the spreadsheet had columns, like market size and competition. Like I, I done the analysis. And so from an intellectual point of view, yeah, they, they, they, they, they, they, they made sense, but did they really make me come alive?

Like, no, no, no, they did not. And the story that she shared with me in that moment that has never left me. And I'll, I'll share with you is, you know, Martin Luther king, when he was, when he was deciding whether or not to step into his leadership role, you know, it was, it was a very non-obvious choice for a lot of people, including him, because he was so young.

He was like in his twenties when, when, when, when all this was happening, when he was thinking about like the role that he was going to play. And so he went to a CIA mentor of his Howard Thurman and he asked him what he should do. And one of the things that Howard Thurman told him was, do not ask what the world needs, ask what makes you come alive, because what the world needs.

It's more people who have come alive. And so, and I love that because I, I run everything that I do now through that analysis. Cause there's so many things out there that just makes sense, right? They, they may, they may make money and they might achieve commercial access success. But, but the thing is that like, when you are running with this idea, it doesn't matter whether you're a founder or somebody trying to steer something internally within a company or, you know, doing something within your community.

You're going to be whenever you're trying to do anything new, trying to create any type of change, you're going to be on the receiving end of doubt. And rejection failure. And, and, and you need to have enough gas in the tank, enough emotional runway to go through that. And you're only going to have that.

If that idea makes you, makes you come alive, maybe it sounds obvious. I don't know. But like, what I find is that we do so much analysis upfront about whether this idea is good for the market. And we do very little analysis upfront about why this idea is really good for me. Is it good for you?

Srini Rao: Wow. I don't think I've ever heard it put that way before.

I love that. Well, speaking of is a good for me is that you, I think this is another line that really struck me. This is, you know, even when it comes to storytelling, which I think is really relevant to a lot of the people here, you say that I've discovered that founders often tell the story of me.

Occasionally tell the story of you and almost never tell the story of us. They tend to miss the opportunity to tell a backer why she's a specific fit for the idea more than any other backer. We miss this part of the story. We lose the chance to turn it outsider into an insider. So one, how do people make that shift from the story of me to the story of us?

Suneel Gupta: Yeah, well, you know that the first time the story of us came up was when I was. We're spending time with the book. You know, I spent time for the book across like all different walks of life, Oscar winning filmmakers, celebrity chefs, to founders of iconic companies. You know, one of my favorite interviews was the president of the MacArthur genius MacArthur foundation, which runs the genius brand.

And yeah, it's just a great, just a great, I mean, you know, it's a great, you know, grant to get, because you get like $650,000, no strings attached. Like there, you literally can take that 60. I mean, I was talking when I was talking to you, th th the, the, you know, the, the foundation, they were like, you could take that $650,000 and you could go buy a house.

It doesn't matter.

Srini Rao: Right. So that was on my list of things to do is to apply for a MacArthur grant. Will they fund a lot of podcasts? Like they do a lot of stuff with NPR. And I remember looking at that thinking, okay, I have it stored somewhere in my walling is one of those back-burner projects was MacArthur grant.

Yeah. You

Suneel Gupta: reminded me to push it up. No, Hey, I would go, go apply because it just sounds like such a phenomenal sort of thing. And I w I just, as a side note, I'm like buy a house. What do you mean? You'd be like, wouldn't you want them, like, if you're going to give somebody $650,000, because they have an idea, they have a passion wouldn't you want that money to be sunk into the pat, like put in the passion and they, and they said like, no, you know, if you, if you go, if you go buy a house, you know, maybe that takes sort of the mental load off where you can then focus on your passion.

We're not going to micromanage how you spend that money. Like go. It's yours, no strings attached. So it's a pretty phenomenal thing. You know, Lin Manuel Miranda creator of Hamilton is a, is a, is a genius award recipient. But one of the things that the, the president of the foundation said to me that I just, I can never forget is that if you're already on a clear path to success that might actually make you a weaker candidate or the grant, not a stronger candidate, but a weaker candidate, because, and I was like, why?

And he's like, well, because what we want to do is we want to, we want to be able to make a mark on your, on your journey. We want to know that we made a difference. And ultimately, I mean, you were speaking to me from the perspective of the foundation, but isn't that like as human beings, like if, if there were like, you know, just a couple of defining qualities of who we are and what we want, everybody isn't that one of them, which is to know that somehow we made a difference.

Somehow we made our mark and, and, you know, If you think about the way that we, that a lot of us sometimes we'll go into a room. Oftentimes we feel like we have to go into a room with an idea that feels Bulletproof, right? Where it's like, we have every answer. We have every, we have everything figured out.

We just want you to say yes or we just want you to write a check. But in doing that, we sort of miss out on this opportunity to tell the story of us or the story of me is my idea, my resume, my project, my vision, but the story of us is how my story and your story come together to tell this larger story.

So the story of us is, is, is, Hey, you know, I've got like 90% of this figured out, but I, but I, but there are a few missing ingredients. And as it turns out, you know, you have been doing this podcast tree tree where you've, you've done over a thousand episodes. You know how to, you know, exactly how this has done.

And that's exactly the piece that we're missing. And that's why we think we would make a great. Like having you join us, having you support us, having you be an advisor for us. That's the story. That's the story about us? You know, and like, this is, you know, this is a, a fundraising thing, but it's, it's, it's really a human thing.

I mean, if you, if you pay attention to like the way the neuroscience shakes out, you know, like the Ikea effect, for example, shows us that we value something that we build up to five times more than something that we simply buy off the shelf. And so, by going in with all the answers, you're making someone into a buyer, you're saying you are buying my thing, but if you go in with not all of the answers, but the opportunity to tell a story about us, you're turning them into a builder.

You're saying let's build things together. And I think you can trace literally every successful project, every successful company, every successful political movement, back to conversations where the person with the idea went into a room and treated people like builders and not by.

Srini Rao: Wow. Wow. Well, let's do this.

Let's get into what you call the four CS of a backable circle. Because I thought that was just invaluable. Like it's funny because w w until you put it that way, it didn't recognize that I had all of these people in my life. And you know, I had this woman yesterday who talked about how to change your life by, you know, writing it as a Hollywood screenplay.

And she actually walked me through one of her workshops and she literally had me list out allies and antagonists that at first, I didn't realize why she was doing that, but now I'm looking at this in the context of what you say here, and it makes sense, but you talk about the four CS and you say, you know, you end up playing, you know, most of your exhibition matches with individuals in the circles.

They will. There'll basically be the wind in your backable journey. And while each back-able circle is different, there are four specific types that are vital. And you mentioned the collaborator, the coach, the cheerleader, and the cheddar. Can you expand on those? Yeah.

Suneel Gupta: Yeah, definitely. And something that you said really stuck with me too, is like, we didn't realize the importance of our circle.

Cause I, I feel like you know, as I'm, as I'm out there talking about the book now, I, I I'm meeting a lot of people who say exactly that. Like, I didn't realize how important these relationships really were until all of a sudden I couldn't see them anymore on a, on a, you know, on a regular basis. I just a couple of years ago, I'll tell you this story real quick and we'll get into the four CS.

I took a trip to Butan. So this is before the pandemic and Butan measures its progress in a way that no other country does they look at what they call gross national happiness. Which, which, you know, they pay attention to GDP. They pay attention to economic growth, but they consider all that stuff to be a factor that leads up into a much broader, larger, more important metric, which is really the happiness of their people.

And they've spent the past 50 years trying to define that and iterate on, on how to measure that. And and, and some incredible things have happened as a result. Like for example, it's one of the only countries in the world that's carbon, carbon negative. They actually produce more oxygen than they consume.

I remember getting off the plane and feeling like I was breathing for the very first time. There is so fresh and they know that that, that, that contributes very much so to the happiness of their people. And so it's a, it becomes a very protecting the environment. Is it it's the top priority for that reason, but, but one of the things I just wanted to share with you real quick is when I was there, I had a chance to spend time with the research team, the people who collect all the data.

And I asked them when you're, when you're out there having conversations with people, is there one question that you could ask. That gives you a pretty good sense of someone's happiness. And they said, yeah. As a matter of fact there is, and the question is, if you were in trouble right now, who could you call and know with 100% certainty that that person would be there for you?

It would, it, would it be available for you? And they believe people who have a clear answer to that question have a much higher likelihood of being happy, but there's a twist. And the twist is whose list are you on? Who could call you? And they know with 100% certainty that you would be there for them.

And they believed that the, the answer to that question is just as important, if not more important. So in other words, it's not just a one-way line. It's. It's it's, it's, it's maybe perhaps what we've always known, which is it all comes back to community and people. And, and I, and I found that to be very much the case when I was writing the book, as well as I, as I studied the lives of these extraordinary people, what I realized is that they all had these trusted circles of people that they, they really, I mean, even the busiest people were spending time nurturing these relationships, because they know how important this small group of people that you can lean on.

They can lean on you. Maybe it is. And so, yeah, when I was, when I was, when I was trying to figure out like, okay, who are these people? What I realized is that some themes are beginning to emerge and that there were four different types of personalities that backable people tended to have in their circle.

And I call these the four CS. So the first is your collaborative. And your collaborator is, is, you know, you really, when you're with this person, you feel like you're in a second city jam session with them. Like they're using words like, yes, and they're building on top of your idea. It's very collaborative in spirit.

And so that's, that's your collaborator. The second is your coach and your coach is different than your collaborator because while your collaborator is thinking about whether your idea is good for the market or for the company or for the community, your coach is really the person who knows you intimately well enough to help you understand, is this idea good for you?

Like, is this idea something that you're going to want to go run with for the next three to five years, it gets back to this emotional runway that we talked about. Like, is it, is it that you, I bring my, I bring my wife ideas all the time and she's like, that's a great idea for someone else, right? Like, you're not going to want to run with this thing and just do this.

Isn't going to be something that you're going to have the juice for in three years. You're excited about it right now, but you won't be then. And so your coach is really important. The third is your true. And true leader. It's pretty self-explanatory, it might sound kind of sappy, but we all need somebody who we can call and no matter what they're going to give us that last bit of energy we need before we walk into a room.

Well, one of the people that I profiled for the book was Ellen levy, who fast company magazine named the most connected woman in Silicon valley. So she's got members of Congress and her Rolodex, and she's got fortune 500 CEOs, but I asked her like, who do you call right before you walk into a big moment to a big meeting, a big pitch.

And she said, that's easy. I call my mom before those moments. So your cheerleader and then the fourth, which I think is, is the least appreciated. But, but I think probably the most important is your critic, but I like to call this person, your cheddar. And the reason I call this person in your cheddar is because if you've ever seen the movie eight mile and then M is surrounded by a circle of friends throughout the film, and they're all kind of building him up for the most part, but there's one friend named Chuck.

Who's constantly sort of poking little holes and his ideas holes kind of like always pointing out the foil to the plan and what we, what we realized through the film is that it's really cheddar, that gets m&m ready for the stage. And it's so important because I think we all have a cheddar in our life.

This is somebody who has our best interest at heart. We know that, and yet they're not afraid to point out our blind spots. They're not afraid to tell us why something doesn't make sense. And I think the vast majority of us tend to sort of push that cheddar away. Right? Whether it's, it's kind of a new conversation, is it kind of annoying?

So we don't want to have them. But what I noticed amongst backable people is they tend to embrace their cheddar. They tend to pull that person in because they know that it's cheddar, that's really going to get them ready for that.

Srini Rao: Yeah. I mean, I worked with a writing coach to do my first two books with penguin and she had edited books for Seth Goden and her commentary was brutal.

It took me a month to stop taking it personally. And finally I clicked. I was like, this is a reason I chose her and she's doing their job. I hired her to do, which is to get me to write the best damn book that I could right then. So I finally realized this guy had to learn how to separate criticism, you know, on the work.

And this, I think is a real challenge for creative people. This is why I stopped coaching writers who wanted to write books, because I learned how to, you know, give feedback from this woman who gave brutal feedback. And so that was my way of doing it. It's like, I don't have time to deal with your emotional bullshit.

I will tell you what's wrong with this. But yeah, I mean that, yeah. And Ryan holiday is a really great quote in a perennial seller about this, where he says, you know, harsh and critical feedback is something you have to learn to take. And sometimes it comes from the people who care the most about.

Suneel Gupta: Yes, absolutely.

And I think that's the defining characteristic of cheddar as well. I mean, you taking harsh and critical feedback from someone who you don't know has your best interest at heart is probably going to fall flat, you know, for the most part. Right. But if, you know, like, Hey, this person is coming from a good place, right.

Like I think that that's, that's that's gold.

Srini Rao: Yeah, absolutely. I think I'm that person to my roommate. I was going through the Enneagram book and they were like, oh, you're a personality type six. And apparently personality type six is, tend to be cheddar.

Suneel Gupta: Wow. Check that out.

Srini Rao: So, if there's something you say about you, the two types, you said there are two types of people in the world.

There are those who play the game of someday, and those who play the game of now, every basketball person I've met at some point in their career, learns to play the game of now. And I want to tackle this question from a different perspective than maybe somebody has asked you before. So you and I come from relatively privileged circumstances.

I'm the son of a college professor, your son of engineers. And I think a message like that is really easy for people like us to embrace because of the circumstances and the context in which we're able to look at that message. But if somebody has barely survived, How do you, how do you account for that when they hear that message?

Because I think we tend to do that to people and say blanket across the board, this is universally true. And I know that this is something you think about given that you've spent time, you know, running for Congress. So I know for a fact this has to be on

Suneel Gupta: your mind. Yeah, yeah, yeah. Look, it is, it is, it is not a universal, it is not a universal message for sure.

Meaning that people who there, there, there are some people there, there are many people rather out there who and a lot of them live in my, in my, in my neighborhood where I am right now, where it's like, they don't have the luxury of necessarily dropping out, moving to Paris and becoming a painter or anything in between here and there.

Right? Like it's, it's, it's, it's, it's there's living month to month. Right now it is, it is, it is the way it is. Right. And I don't think a message of, Hey, like beef, what you're doing right now go take that risk is necessarily something that will, will resonate and nor, nor nor should it. I, I think though that there is, there are a tremendous, there are many, many people out there who are not in those situations who are afraid of taking that risk.

And I think that what we have to do is unpack what that risk really is. And it gets to what you just talked about, which is like, what really is at stake here. Like what's truly at stake for our parents, for your parents screening for my parents, had they failed? I, I mean, I mean, what, what what's best case scenario.

They have to go back to India, like worst case scenario, maybe they're homeless. Right. I, I, you know, I don't know, but like it's, it's there wasn't a lot of infrastructure around them at that point in time, I get a lot of credit that I know deserve for doing things like starting a company or, you know, attempting to start companies and for running for Congress and, you know, and, and it's like, wow, that, that, that takes a lot of risks, but not really though, because I would still have a roof over my head.

I am not going to start worst case scenario. I can move back with my parents. Like, they're there. I'm not like I'm nowhere near it. Like, I'm not, I'm not even close to the risk profile that, that they were. Right. So what, w what are we really talking about here? I think at the end of the day, what we're talking about is reputational risk, right?

We're talking about the idea that we're not going to have an explanation which ultimately, I think that's what a resume is. It's an explanation. That, that, that impresses people or, or that, that, you know, that, that will impress people if I take a safer path. Right. And so that's a very, very different type of risk.

And those are the people that I think we have to speak to when we think about sort of the game of someday versus the game of now. But at the end of the day, I have, I know people and I, and you do as well, or perfectly comfortable doing what they're doing right now. And it is isn't isn't to judge them in any way.

I have friends here in Michigan that work at auto companies they've been working at auto companies, their entire career. They will probably retire from these auto companies and they are happy and, and this message is not for them. It is for the people, however that are saying to themselves, Look, I'm going to do this for two to three more years, and then I'm going to go jump to this next thing.

Right? And then you ask them, well, why what's going to happen over the next two to three years? I, you know, I'm not, I'm not ready yet. I'm not ready. Right? Like this is the three sort of famous words. I'm not, I'm not ready. You know, why aren't you ready? And, and, and then it's like, you don't get the answer that I, you know, there's not, you're not going to build any type of capability over the next three years.

You're not going to have, you know, dramatically more money in the bank. And the thing that I realized is that like, if there was one common denominator amongst the hundreds of people that I studied for this book that have all done, I think extraordinary things is that none of them were really ready.

Like three friends from design school were not ready to start Airbnb angle, a, a mid-level talent manager, who was, it was living paycheck to paycheck. Wasn't ready to start SoulCycle, you know, a 15 year old from Stockholm. Sweden was not ready to build an environmental movement. But today Gretta Thornburg is time magazine is youngest person of the year.

If these people were not ready and there, and there were setbacks and there were failures and there were mistakes along the way, but I think they all attend. They all sort of adopted, you know what I call in the book, the game of now, and the defining characteristic of the game of now is that the opposite of success is not failure.

It's boring. Wow.

Srini Rao: Wow. Yeah. Yeah. It reminds me of that, that 50 cent quote from his book hustle harder. He says, don't look at the immediate payoff of something. Look at the long-term potential. And you know, like I remember sitting around at my parents' house for seven years building unmistakable and, you know, it was going nowhere.

Like I could have easily, not maybe easily considering a been fired from all of them, but I could have gotten a job. And I realized what was happening during that time. It was, you know, I wrote about this once I said, you know, there's a difference between your current earnings and your earning potential over time.

And where I learned this lesson, believe it or not was back in Silicon valley. I was, I think I was just, I was going to be, you know, I graduated in four and a half years, so I have one more semester left in school and I had two interviews. One was with some guy who ran an online gift registry and he told me, we'll pay you $25 an hour.

Another was with a young startup founder. And he said, look, I don't have any money barely any money he said, but you'll basically be my right hand person. You'll learn a lot. That guy ended up. If I remember correctly being Auryn Hoffman who went on to make hundreds of millions of dollars. And I always jokingly say $15 cost me a hundred million.

Suneel Gupta: It's funny. I know. Or yeah, like, I mean, yeah,

Srini Rao: I'm pretty sure it was him. I like, I don't know if exactly wasn't, but I very distinctly remember something along those lines, but I never forgot that experience. Yeah,

Suneel Gupta: yeah, yeah. No, I, I love, I love that. I love that quote. And you were asked me in the beginning of the interview, like, what do I want for my kids?

I think it's that right? I think it's, I think it's the, I think it's the, the ability to say, you know, like, let me look, let me look at the long-term and again, like, you know, it's pre. Th there's privileged to that, for sure. We're sure there's privileged to that because I hope that, you know, have I'm not going to have, you know, my, my, my goal is not to get to F-you money, but my goal is to be able to get them the ability to, to, to say, yeah, I can take, I can take some, I can take some risks and you know, go chase a couple of things that maybe I otherwise wouldn't have chased and, and go commit to those that that's, that's, that's, that's the goal.

And, and, you know, I would hate for them to feel like they can't take those risks or they want to take the saber path, even though the other path is one that just makes them come alive.

Srini Rao: Yeah. Well, I'm so glad you brought up the F-you money because I wanted to ask you, you know, and you've sold startups now.

You've been, you know, you've had this book come out. So by the most measures your successful, you know, financially probably I'm guessing you're doing pretty well. Has your definition of success and wealth changed as a by-product of that.

Suneel Gupta: Yeah. In a, in a, in a lot of ways, I think like, you know I guess I'm just no longer you know, I guess it's at a certain point in time, I started to think to myself, I have enough, you know, there was a feeling of enoughness and it wasn't a lie, but I'm just, you know, it wasn't, it wasn't a lot, like I, you know, like my, my start-up did fine, you know, we, we, we, I guess in baseball sort of, you know, we hit, like, you hit like a double, you know, and, and, and, and it gave me enough.

It gave me enough cushion to have the luxury, to be a writer. And to, you know, start making some money off of, you know, some slow money off of what comes off of writing books, which is not, which is not a lot, but that compliment to what we have is, you know, going to be going to be enough for us in a place like Michigan.

And so then the question is, can I, can I get over my FOMO of looking at my former colleagues who are out in Silicon valley, like just making like a lot of making a killing and if, you know, feeling like I'm being left out. Right. And, and, and I, and I guess the way that I I guess my mindset has shifted is no, I think that I have enough.

I have enough to be able to kind of just do what it is that I want to be able to do. I have enough to spend my day. The way that I want to spend my days. And that in of itself is, is the richest is just the richest reward. And it's, again, it's not the, it's not the judge because I think we all have to figure out what our own definition of success is.

Coming back to Butan. The reason I met, the reason that I Revere a country like Butan isn't because I think they have it all figured out, but it's because they had the courage to be able to say, well, I know every other country's defining success in a certain way. Let us define it the way that we want to define it.

And I think that we have to do that as, as, as individuals is to say, yeah, there's a lot of people who define success in that. I need to figure out how I define it. And for me, it's, it's, it's very much at the, at the, you know, as Seth Godin would say, it's very much at the verb level and not the noun level, right.

The verb level being, what are we actively doing every day? Like, what's the, what's the action that's happening at the day-to-day level, rather than the noun of saying something like, well, I'm a venture capitalist or you know, I'm a founder of a company that's doing really well. I want to write, like, I just want to write that's what I want to do.

And that, that, that to me,

Srini Rao: Yeah, I love this idea of enough because I, we had a woman named Venetia Tucker here who was a financial advisor, had had billionaire clients. And she said, that's the one thing we're lacking is the definition of enough. And I remember in brighter Carol's book, he talks about goals and he specifically talks about financial goals and he says, you know, if you don't know why you want a million dollars, he said, then it's an empty goal.

And I remember thinking about all the things that I needed money for. And when I actually came up with the number, I was like, wow, this is so much lower than I actually thought.

Suneel Gupta: Yeah, yeah, exactly. Yeah, no, I feel, I feel exactly the same way and I, and I have a family as well, you know, and I want, I want to make sure that they're taken care of, but I think if you, if you really sort of, you know, and I think that like, you know, for me being completely on the same page as, as, as with my, with my partner about this and just making sure that she, and I completely see eye to eye on what it is that we need and what it is, we don't need.

It's free, man. Like I, at the end of the day, like I, you know, I'm in my early forties now. And it's like the thing that I think about more than anything else is freedom, right? Just freedom to be able to do what you want to be able to do. That matters to me so much more than anything else.

Srini Rao: Yeah. Yeah, no, I, I absolutely love that.

So it's funny, you mentioned sort of the comparison, cause I was literally writing about this this morning about why getting everything you want won't ever make you as happy as you think it will because you, your reference groups keep changing. And I realized there was the only antidote to this hedonic treadmill was just being aware of it.

Like you actually are never going to get over. That is what I realized. I was thinking to myself because I mean, you know, this is an author, right? YubiKey, you get a book deal from being a blogger or having an online presence. And your reference group is now published authors. And if you're at an infant like mine, where everybody is like Seth Godin, Ryan holiday, you go from being a blogger who got a book deal to being the red-headed stepchild.

Suneel Gupta: Yeah, yeah, yeah. And then it just gets back to like, why do you, like, why do you want to be a writer? Right? Do you want to be a writer? Do you want to be a writer because you want to be known as a writer or do you want to be a writer? Cause you, cause you want to write, you know, like you're sitting down, you're writing a thousand words every day.

Like you would not be able to sustain that. If at the end of the day, what you were trying to do is create best. Right. Like one of the, one of the, one of the reframes that I had over the past couple of years is to turn my to-do list into a, to learn list. Like what do I really want to learn? Right. And, and, and for me, I really wanted to learn how to become a better writer.

I still, I think I could spend the rest of my career life, really trying to learn how to become a better writer. That's what I think about when I sit down at my desk every day. But if my goal, I can tell you this right now, if my goal was, I want to write a best-selling book. I never would have written backable.

I never would have written it because it, I would've, I would've everyday I would've sat down and I'd be like, this is terrible. This is terrible. This is terrible. I never would have published anything. I never would have shared anything out, but I was like, I want to learn how to be a better writer.

That's my goal. And so therefore I have to write and therefore I have to put it out there. And in order to get the feedback that I need in order to write.

Srini Rao: Absolutely. So I have two final questions for you. There's one question and one story I didn't want to get out of this interview without having your total listeners.

And it was about how your parents met. Paulie was one of my favorite parts of the book.

Suneel Gupta: Yeah. Yeah. Well, so the, the hanger, Ronnie becomes Ford motor company's first female engineer in 1967. And then ironically she's into her job and she she's she's driving around Ann Arbor, Michigan and her car writes down.

Okay. And so she, you know, she knows how to, she knows how to look at an engine. She pops the hood and she's looking at it, she's inspecting it herself. And she realizes like, she's missing a part, like one of the parts of shop. So she walks to a local, to a phone booth in town and she opens, you know, cause they had a phone boots back then and she opens up the phone book as I was phone books.

It's attached by that wire and she, and she looks. The most common, Indian name that she can think of and, and a guy answers the phone and she asked for that guy, and as it turns out that guy's not home, but the guy who answers the phone says like, that's my roommate. He's not home. And that guy was my father, the guy who answered the phone.

And and so he wasn't home. His roommate was home. And so my father and my mom strike up a conversation. He goes down, he helps her with her car. And as I say, you know, the rest is history. I love

Srini Rao: that. Well, I have one final question for you, which is how we finish all of our interviews with the unmistakable creative.

What do you think it is that makes somebody or something unmistakable?

Suneel Gupta: I think it's I think it's the gosh, that's such a good question. I think we all have our more of a finger. Than than we than we. And we think we are, I think we are all very unique. And, and I think that it takes a lot of self-reflection to understand what that is.

You know, I think, you know, I'm, I very much subscribed to the idea that we are sort of born with with, with certain gifts. And we have responsibilities to those gifts. We have to figure out what those are and we have to, we have to share those. And when we don't, we feel off and I think other people feel off around us because we're not sharing who it is that we, that we are.

And so I think somebody who is unmistakable is somebody who is stunned the work to really tune into what those gifts are. And then, and then is actively sharing those gifts with the world, giving them.

Srini Rao: Amazing. Well, I can't thank you enough for taking the time to join us and share your story and your wisdom and your insights with our listeners.

Where can people find out more about you your book and all the work that you're up to

Suneel Gupta: the you go to You'll see, you'll see some free stuff over there, some free content and, and and you know, I'd love to connect with you there.

Srini Rao: Awesome. And for everybody listening, we'll wrap the show with that.

Suneel Gupta: Thank you for listening to this episode of the unmistakable creative

Srini Rao: podcast while you were listening. Were there any moments you found fascinating,

Suneel Gupta: inspiring, instructive, maybe even

Srini Rao: heartwarming.

Suneel Gupta: Can you think of anyone, a friend or a family member who would appreciate this moment? If so, take a second and share today's episode with that one person because good ideas and messages are meant to be shared.

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Suneel Gupta

SUNEEL GUPTA is the author of the bestselling book "Backable". The book is rooted in Suneel’s journey from the "Face of Failure" for the New York Times to the "New Face of Innovation" for the New York Stock Exchange. Suneel is the founding CEO of RISE, which partnered with then first Lady Michelle Obama to deliver low-cost healthcare services to people in need. RISE was named "App of the Year" by Apple and sold in a successful exit to One Medical (NASDAQ: ONEM). Suneel later ran for U.S. Congress and now serves on faculty at Harvard University and as an emissary for Gross National Happiness between the United States and the Kingdom of Bhutan. When a reporter once asked Suneel about his purpose, his response was to “find good people, and inspire them to do what inspires them.”