Ravi’s Story: Demanding and Supportive - [Glue Guys, EP.11]

One of our investors had this CEO summit. I went and I gave, like, a fireside chat there, and the person right after me who was gonna be talking was Jeff Bezos. And I was like, whoa. I mean, you know, that's not my typical follow up, you know, guest. So anyway, I go and I give my talk, and I'm kind of like, going to go into, like, the little. What I actually thought was gonna happen is they had this little, like, room in the back for, like, the speakers, and I was kinda like, oh, man. I'm like, you know, like, give Bezos a little fist bump as we go by, you know, like, that kind of thing. And then the founder of the comes up to me as I'm walking off, and he's like, hey, man. Like, Jeff and his team are not comfortable with you staying here for his talk. What? I mean, it's so absurd. You're like, what? What are you talking about? Welcome to Glue, guys. We're your hosts, Shane Battier, Ravi Gupta, and Alex Smith.

And we're bringing you behind the scenes.

Of the locker rooms, the boardroom, and.

The living rooms that taught us everything.

We know about what it takes to.

Be great leaders and even better teammates and friends.

We hope the conversation helps you bring more ambition and more joy to your own work life and relationships. It certainly has for us. Okay, we ready for the Ravi show? Yeah.

We want to get to know Ravi Gupta. Ravinder. Jamal Gupta. Better today if Ravi and I went to school together at Duke. Although we were not friends at the time, we crossed paths at a few fraternity parties a few times. Not for lack of. Of not wanting to hang out with him. I just didn't. Didn't run with him. Yeah, but we got to know each other at a wedding. A buddy of ours got married, and, you know, magical things happen when you go to Santa Barbara county and you drink a lot of wine.

This all starts with the napkin story.

Yeah. It starts with Chain tying a napkin around his head at a wedding. Yeah.

Explains a lot.

That's my. My. My go to party trick. It brings people together because nothing says family in love like taking the linens from the table and wrapping them around your head. And it's a. It's a party game. I highly recommend. It's. It's great for grandparents. It's great for kids. It's great for the bride and groom. It's ridiculous. And so we're hanging out at our friend's wedding, and I tie a napkin on. On Ravi's head, and it was. It was love. After that.

That's right. That's right. Ten years ago, Alec, you've never tied a napkin on my head. You know, we had a new stage of our relationship.

That's right.

Yeah. That we gotta reach.

That's right.

Well, I just wanna prep, you know, everyone for. I. I think that this is probably more interesting and more exciting than the Alex Smith story that we bored you with. You know what I'm saying? So I'm glad that we finally get together.

I can't wait for this.

A good story, you know, like a real life story. All right, where do you want me to start? You want me to start? You tell me.

Well, I think you talk so much about your dad. Just talk about your parents.

Yeah. All right, so I'm just actually going to go even one further. I'm going to start. My grandfather.

Yep.

Okay. So my grandfather born in India, 1922. They. He and my grandmother had five kids. And at 35, my grandfather was like, you know what? I don't. I don't want to do this the way we're doing it. And they didn't have, like, much at all. But you gotta remember, like, in 1957, they don't really know anything. You're not like, Googling how things are. So at that point, he just hears, like, America, streets paved in gold, land of opportunity, whatever. So he just like comes 35 years old, comes, and he comes by himself and he leaves my grandmother and the five kids there. And I bring that up only because, like, it's like a crazy thing, you know, like coming to a different country, leaving everybody there. And at that point, I guess this was like something that would happen in India where the person would just leave and they would never come back, you know? And so people were telling my dad and his brothers and my aunt and my grandmother, like, this dude's gone. He's never coming back. You know, and so they just like, you know, they thought they were gonna see him again, but you don't really know. I mean, you know, there's not like, FaceTiming with them, you know. And so anyway, he goes by himself three years, and he's just like, in America, 1957, 1960, you know, and strange.

Time to be brown in America.

Totally. It's super strange, right? And like, he. My grandfather went to Auburn, so it's like he was like in the south, you know, and he'd already done all of his degrees, all of his work, but he had to redo it because America didn't recognize, like, what are we supposed to look at here to know that you actually did what you said you did.

Right?

There's no, like, you know, system that they can rely on. So anyway, he, like, you know, goes and redoes his degrees. He's working all the time, whatever. 1960, comes back and brings back my grandmother and the. My dad's youngest sister and leaves the four boys there. So he, like, just goes back, sees them, brings back my grandmother and the daughter, and leaves the other four boys there again. So 1960, 1963, my dad and his brothers are just alone in India at, like, this boarding school. Now, boarding school sounds fancy. Like, not fancy. Like, literally just some school that will, like, allow them to live there, you know? And so 19 again, 1960, 1963, by himself. So my dad, at this time. How old are.

How old your dad? How old are the boys? Like, approximately. Yeah.

I mean, My dad was 8 when my grandfather left and 14 when he came to America. So 8 to 14. So it's kind of like the age of, like, our kids, you know, roughly speaking. And like, that period, he's gone. My grandfather, like, my dad and his brothers are just, like, there. So then they come and. I'll get to me in a second, but you asked about, like, my parents, right? Like, they come and they come to Harvey, Illinois, right? And again, like, it's weird, 1963, to be a bunch of brown people in Harvey, Illinois. And they come and they go to school, and my dad tells this great story of, like, they were playing baseball in the yard. And he's never seen baseball. He doesn't know any of this. So he's holding it like a cricket.

Bat, you know, there.

And you can just imagine these guys just getting crushed, I'm sure, by people, like, making fun of them. They have accents, you know, all this stuff. But they were smart. And my grandfather, to his credit, he went to the principal and was like, these guys are ahead, you know. So my dad graduated high school at 15 years old, and he went to college at 15. And then they ended up in Louisiana. And they went to Louisiana because it was the cheapest public school in the country. LSU at that time was $85 a semester, okay? So my dad always says he gets us. He's like, I got a scholarship to college. I'm like, yeah, dude, it was 85 semester.

Like, you know, you get what you pay for.

Yeah, exactly. And so they all went to all my dad and his brothers. Most of them, they went to LSU. My dad went there. He graduated 18. My dad graduated college, 18 years old. He's a bright dude. Anyway, he went to duke for his PhD and then ultimately came after that, got married to my mom and. And then my brother and I came along and, you know, that's there. So, like, I'd say the thing I would tell you about them is like, my dad is. He's smart, he's funny, he's demanding, he's very high expectations and he's very like, willing to tell you the truth even if it doesn't feel great. But he, but he does it because he thinks that's the way to show his respect. And I've like, really taken that from him, I hope. And the other thing about my dad, he's an amazing advice giver and he is like a vault. If you tell him something like, it is like people tell him all sorts of shit. Yeah. You know, but it's never going anywhere. And then my mom is like, just full of love. My mom stayed home with us. We were like her world, you know, like, and everything was revolved around us. And to this day, like, if I. My mom thinks I do no wrong, like, none whatsoever. Now I definitely think she liked my brother better growing up.

Yeah.

So I've like, worked hard to like, make sure that she likes me. Now. She don't like when I say that. But then, like, you know, one thing about my mom that she's like, really worked on is like, when my brother and I went to college, my mom was, you know, like in her early 40s when I went to college and she was a stay at home mom. And all of a sudden, like, both kids are gone and early 40s, like, I got to like, figure out a new thing. And so I admire that a lot about her too, that she like did that. So yeah, they were like, very devoted parents and very like classic Indian parents in the sense of like, very high academic expectations. And, you know, that's probably why they.

Liked your older brother better too, for firstborn.

So.

Sure. Firstborn son. My brother, like, you know, you know, you guys know him. He's handsome, he's a doctor.

It's totally understandable.

So, like. So do your parents ever talk about the civil rights period in America when they first got here? I mean, you. Throughout history, you know, the black experience, it's very well documented. I have never heard. Heard anyone talk about another type of brown person's experience in the 60s in America. Do they talk about that or is it, you know.

So my mom, My mom came here after that. My mom came here in like the mid-70s and my mom's experience was much more like, my mom didn't know how to drive, you know, and she would, like, wear like a. Sorry. And so, like, I think that my mom is just, like, not her style to talk about that. My dad, for sure, like, he was, like, in it, you know, and, like, I think his experience was actually less about the 60s than it was, like, when he started working. And when he started working, he showed me this letter one time that somebody wrote to suggest him for a promotion. And in the letter, which is supporting my dad, it's like, he's not like other foreigners. And this isn't a real letter. That is, whatever. And so I think that the biggest thing, you know, a shame what it is. Like, when I was growing up, 99.9% of my parents. Friends were Indian.

Yeah.

So I actually think what really happened was they just, like, had shared experience with other Indian immigrants.

Yeah.

And like, the way that they dealt with it was they kind of, like, avoided it other than, like, you know what I'm saying? Like, the entire circle of, like, very close friends was just other people who had come.

Yeah.

And all you needed for, like, a ticket to be in the group was to have come from India.

Yeah.

Like. And all of a sudden there was, like, kinship and, you know, all that.

Did you know your grandpa?

Yeah, yeah. My grandfather was my grandfather. Only he passed away during COVID He was 98. And my grandfather was, like, an amazing dude, but, like, not. Not at all, like, a perfect guy. Like, he was my grandfather. Like, he. I think, let's see, he was obsessed with education. Obsessed with education. So there's 17 cousins on my dad's side. Okay. I'm the only one without a graduate degree out of all seven.

Slacker.

Slacker. Like my grandfather, when I told him, well, we've.

We've discussed your, you know, your structured studies at Duke.

Yes, we'll get to that. Yeah, exactly. Exactly. Hey, hey, hey, hey. But my grandfather, when I told him I wasn't going to go to business school, you know what he told me? And this is not to knock anybody else's profession, but he, like, pulled me aside, dead serious. Okay. Now at the time, I'm working at kkr, like, this is like a real firm. And I told him, I was like, he's like, you know, your dad tells me you're not going to go to business school. And I was like, you know, they told me I could stay and I'll get promoted without going. And he's like, you know, can I talk to you? I'm like, sure. And he's like, this reminds me of the high school kid who's a plumber and he doesn't go to college. Cause he's making money as a plumber. And he's like, you shouldn't be a plumber. And I'm like, oh, gosh. Well, like, I don't think that's a great analogy, Baji, you know, but yeah, so, like, very demanding. In his speech at our wedding, first thing he said, he's like, I'd like to propose a toast to my least educated grandson.

Oh, wow.

Yeah.

Shots fire.

But he was funny too, you know, like, he. But he was. He was tough.

There seems to be a theme of direct feedback in the.

A lot of direct feedback. Demanding and demanding and supportive right there. And always sure. You know, the other thing about the good is always sure. Even if they're wrong, you know, so a lot of conflict, a lot of conviction.

Conviction.

But yeah, most of my family, based on his experience, most of my family's in medicine because basically, like, he had come here and he was not a doctor, and he basically saw these doctors doing well and he was like, okay, all of my grandchildren are going to be educated. And he basically wanted all of us to be doctors because he was sort of like, that, like, eliminates risk, you know, and like, you're good. You have, like, bought an insurance policy that pays for the rest of your life. And like most of my loves of me, he loves. He loved my brother. He loves all the other kids. And it took a while for him to kind of come around to me.

You know, you and I have talked about this before, but, like, when you went to Duke, you didn't necessarily know what you wanted to do at that point.

No idea.

Right. Like, I mean, obviously you're going there. You love Duke because your dad and you know.

Yeah.

You're going for like an education, but a good time.

Yeah, like, for sure. Talk about your college choice.

Yeah, talk about your college choice. I mean, it's interesting how you got to Duke.

Yeah. Yeah. So I mentioned my dad went there for his PhD. All of my family, all the extended family had all stayed in state for college. So all I wanted to do was go to an out of state college. That's all I want to do, just to be different. I was just like, I can't be like everybody else, whether or not that was good or bad. And same thing of like, I can't be a doctor. Everybody else can be a doctor. My brother is going to be a doctor. Like every. My brother Got into this seven year med program. So it was like, sure that he was going to be a doctor at 17 years old, you know, he's already admitted to medical school. It's crazy. So I was like, I cannot be a doctor and I have to go to an out of state college so I can go to my parents. I'm like, can I go to an out of state college? Because they were going to pay for it. And they're like, well, it depends on which college. And I didn't even ask about Harvard because I knew I wouldn't get in, right? So I was like, what if I got into Stanford? And they're like, yeah, if you get into Stanford, like you can go. And I'm like, cool. So I applied early decision Stanford. I've never been there. I've never been. I'd never seen it, but I just, it was like they said I could go to school. So I applied early decision. I'm waiting, waiting, waiting. And I was summarily dismissed. Like, not defer. I was like, you guys don't want to defer. You're sure? And they were like, we're very sure, you know, like, we do not want you here. And so anyway, I was lucky enough to get into Duke and obviously it was the best thing ever. I met Avni, like, you know, such a wonderful time. But like, originally I want to go to Stanford just because I knew my parents would let me go. So anyway, I go to Duke and I should have mentioned this, but like, I was able to do okay in high school without doing a ton of work. Okay. And so I kind of thought that was going to continue at Duke. And so my first year I was just like messing around. And it's crazy to do this because I didn't even drink. Like, to mess around as much as I was messing around is hard because I was dead sober all the time. But you guys were joking. We were joking one time about like your college commitments. I mean, I had 10 hours of class a week aggregate, okay? And I probably went to like two and a half hours the first year per week. I mean, like, and I was like, man, like, you know, like, think about how absurd that is. There's 168 hours in a week. What.

What is farting around for Rev Guppy look, like in college, I mean, a lot, a lot of goldeneye, you know?

No, dude, this. I'm saying, it's so dumb. Like I. Okay, so Shane, Alex, you don't know some of these places?

I used to crush goldeneye by the Way.

Such a good game.

Yes.

I have no excuse. I would just hang out in the Alpine bagel. You know, I just like hang out. People come back from their classes and then they go to class. I would just still be there. I'll just hang out with everybody, right? I. You know that McDonald's with the comfy couches in the Bryan Center. I just. Just hang there. Those couches. I would hang there for hours. You know, I'd like, read my book. I just like, just hang it whenever someone want to hang. I was available and. And so after the freshman year, I came home and my parents sat me down and like, I know, like a terrible gpa, but I know I have a great gpa. And they're kind of like, look, you have three options, okay? Option one is you can go to a college and pay for it yourself. Like, you can go to. Come back to and go to University of Illinois and go pay for it yourself, right? Okay. Option two is you can live at home and you will. You can transfer to Northwestern and we'll like, be on your ass because obviously you're not capable of, like, doing things on your own. Option three, you can, like, pull it together and go back to Duke. But, like, you got one semester to, like, show us that you're going to take this seriously. And I was like, damn. Like, I like Duke. I don't want to come home.

I don't wanna.

Exactly. And I was like, man, maybe if I, like, just did a little more, like, Duke is not like, it's not that crazy. Like, there's grade inflation. There's all sorts of things that you can, like, you know. So anyway, so I just like went back and kind of like pulled it together and started doing much better in school. But like, yeah, like, it was a different college experience than you guys had.

Okay, so is that the moment that, like, kickstarted?

No. You think that kick started for me? That was like a little kickstarter. The real moment that Kickstarter for me was I didn't have an internship after junior year. And I was like, looking, looking, looking, and I couldn't. I just like, couldn't get one. Okay. And so I went home and I was like, hey, dad, like, I googled this thing. Like, you know, you know this guy. Can you introduce me to this guy? And my dad looked me and he's like, no, I'm not going to do that. I'm like, why not? And he's like, because I don't know if you're going to take it seriously. I Don't know if you're going to go do this. So, no, I'm not going to introduce you to this guy. I'm not going to go and like, tell somebody that they should talk to you because you're not demonstrating any seriousness. And I remember being like, that was like, kick yourself into gear. And like, I was very lucky because, like, you know, you have an option to ask your dad to introduce you to somebody or whatever for an internship. But, like, that was a real alarming moment of like, even my parents don't believe in me. Like, I've, like, messed around. I, like, done this in a way where even my dad is like, I'm not doing this. And I was like, listen, if you introduce me to this guy, like, I will work. I will work. And like, I kind of like begged. And then he did it. In that, that summer, I like, I like, balled out. I, like, really worked.

What was the internship?

It was at a consulting firm in Chicago called ZS Associates. And I was working all the fucking time. I would. I would stay there at night. I would like, just work. I would just work. Cause I was like, I cannot let these guys down. And, you know, I was embarrassed. I mean, I'd gotten there through a connection, you know, So I was like, I gotta. At the end of this, I have to be like the best one that they've ever seen. And I'm never going. I'm never. Honestly, I never thought about this, but I was kind of like, I'm never relying on somebody else needing to do something for me again, like, because it's such a terrible feeling. You walk in, everyone's like, you know, you kind of know that. Everyone's like, oh, this guy, the shithead, right? And so I was like, I'm never ever going back there. You know, I'm never. I'm never going to be the one who's like, reliant on something like that. And so that was what. That was what kickstarted.

And talk about Dr. Rajan. All right, so we always talk about the experiences that shape us before we turn 18.

Right.

And so you had Mr. Perfect, literally. Yeah, as a brother. Oh, you know, so you're. You're mess. You're farting around.

Yes.

All right. You almost found out.

Yeah, yeah, we call it farting around.

Find out.

Yeah, almost found out.

So you. You almost found out. And so, you know, you always talk about Mr. Perfect. And yeah, Raj is. He's unbelievable guy, good looking, unbelievable family.

Beautiful girl, super successful. We got it.

Much better golf game Than you.

I know, I know. We go down the list.

Let's talk about growing up in the shadow of Mr. Perfect.

My brother's three years older than me. His perfection extends to. He was even really nice. He didn't even believe me. He beat me up. Like, that's the thing that's so crazy is like, it made me even matter because he was so nice to me. Like, he was such a good big brother too. You know what I'm saying? Like, you couldn't even be mad if that makes any sense, right? Like, but he was so. Yeah, like, my brother. He was studious. He was, he was, he was fun, you know, like, he. And you could just tell my parents, like, they were very proud of both of us, obviously. Like, I exaggerated, but like, they, you could just tell like the way that anybody would be. They're like, gosh, like, we really did it, you know, Like. Like, this guy, he's so good, you know? And like, they were just, they were just happy. And like, the other thing I remember is like, adults, all my parents, friends, they loved my brother because he would chat with them. He could, like, I mean, I didn't, I couldn't interact with a grown up when I was a kid. Like, they'd ask me something, I'm just super awkward, right? Like, I had acne. Like, my brother, he would pass through all that stuff and like, they would talk to me. He would just be chatting it up with them with the aunties, you know, just like, you know, and so that was very impacting because one, like, I was just like, I gotta be different. I can't do the things that he does. Like, and so he was great at science. I was like, I can't do that. And he was like, my brother. Like, I told you I couldn't get an internship after junior year. My brother was like, working in the hospital in high school. Like, it just like. So he had like a job at the pharmacy, like when he was like 15 years old or something. Like, you just like, so obviously, you know, like, good.

Yeah.

And so everything, so much of my life is like a reaction to him, you know, of like, my brother played baseball, I wanted to play basketball, you know, like, he was gonna be a doctor. I wouldn't be anything but a doctor. He went to in state, I gotta go out of state. Like, just so much. And in fact, we weren't all that close until finally when he went away. Then like, when he went away and I went to Duke, then we finally got closer. Because I think that two things, one I, like, appreciated. You know, like, wow. Like, he was so good. He was good to me. But the other thing that happened. And my brother deserves all the credit for this. Like, I don't like being big brothered. I don't like people telling me what to do.

Yeah.

You know, and so I. Even though that's a completely reasonable relationship for him to have when he's three years older than me and to kind of, like, be the. The voice of reason, all that stuff, like, I don't like that at all. And so my brother, to his credit, like, he didn't do that.

Do you think he thought he was gonna have to, like, have a room in the basement of his house for you to live in?

You know, my brother's so good. He would do it. He definitely would do it.

He totally would.

He would totally do it. He wouldn't think anything of it. You would be like, my brother's more talented, and he'd be like, kind of one of those guys. Um, Yeah. I mean, it probably wasn't a. It was probably a remote possibility, but not zero, you know, but, like, I think that he viewed me as, like, a little lazy and, like, not going to. I think he thought I had a lot of potential, like, in, like, for real. I think he actually thought I had a lot of potential. And I also think, to be fair to him, I think what he wanted at some point was to be able to tell me, like, yo, man, like. Like to be another older figure. Yeah. And to have me, like, listen to that and to have me, like, be inspired by how good he was doing and all that. And I just, like, was not into that until when he started treating me more like a peer. Then all of a sudden. I want to hear all the advice.

Yeah.

Because I love getting, you know, perspective from friends and peers, but I don't like being told what to do. So anyway, that. That. I think he's. I think he saw me like that. And now we're, like, ultra close, as you guys know. Right. But, like, it. He deserves a lot of credit for that. Yeah.

So this has shaped you. You go through Duke graduate. Turn it around. Turn the ship around.

Turn the ship around.

Okay, now, you know, I think our audience wants to hear how the great Ravi Gupta started. Started his. His road to. To superstardom in the. In the C suite.

Yeah.

Out of school, though, You. You immediately go to KKR. You went. Okay, first.

Yeah, I went to McKinsey. And I went to McKinsey. Two years there. Basically. McKinsey is like a. Especially then it's like a socially acceptable way to not know what you want to do. Right. It's like you have no idea what you want to do. So it's just like a general business education that they pay you for. And I should have paid them, you know, because like, you just get to learn on their dime as a young person. It was amazing. Amazing. I did that for two years. Basically. I got to kkr, Alex, because the smartest guy or the best guy in the McKinsey class, two classes above me, had gone to KKR and I didn't know anything. Again, like, your world is so narrow. Like, I meet kids now and they're like, I want, I want to do this. I want to found a company. I want to do this. I didn't know anything. I just like, knew what the best person in the class had done. I was like, okay, I should try to get that job. And so then I went and I got that job. And so I went to kkr, moved to New York, and then I was at KKR for 10 years. But I did two different things at KKR. And the only reason that's relevant is I joined as part of like the consulting team. Okay. And KKR is an investment firm. So the big thing that KKR does is invest. The consulting team is called Capstone, effectively helps with diligence and then helps once KKR buys the companies. So I was on that side. Okay. And like, that's not the main thing KKR does. And so there are moments at least, you know, years and years and years, they've done a much better job of this now. But like, there are moments where you kind of felt like a second class citizen doing that, even though it was a great job. Yeah. And this does tell you something about my personality, good or bad. Like, I didn't like that, you know, like.

And you knew at this point, though that, I mean, you said it at least with your talk with your grandpa, like you could. There was room to move up to get over to the other side.

This ain't it.

Yeah, yeah, basically, exactly. This ain't it. And the. And so at some point I was going to leave and just because I was like, yeah, I don't want to do that. And then they were like, why don't you come and be on the investment side? And I didn't know how to do that. And this is when I've told you some of the times, like, I really was struggling, but I knew I wanted to be on the better side or the more like central side at the time, but I didn't know how to do it. And so I moved over and I was the. I was one of the first people to move over and do that. And I almost got fired. You know that. That's like an interesting part of this thing because I had gone over and I was like somewhat like senior on the consulting side. And then I thought I should be senior on the investing side, but I had no idea what I was doing. So this is the time I told you guys. I was like crying at my desk and sitting there just like, what am I going to do? 11 o', clock, open model. You know, Alex is laughing at me. But it's true, you know, and like just sitting there and you're just like, oh, my God, I don't know what to do, you know? And you just had to like. I remember one of my bosses kind of like sat me down and was like, you gotta kind of eat some shit, you know, like, you gotta go all the way back. And so I had to act like the junior most person on the investing side. All these things are tiny, like, tiny things in retrospect. But at the time, it feels like such a big deal. All of a sudden your peer group is five years younger. Right. You had gone from being somewhat good to. To like just not knowing anything. You're asking all these questions to people that, you know, you supposedly have more experience than. My title was higher than theirs, but I was like worse than them at the job. So it's very, like a very humbling.

Who was, who was that manager?

So it's a guy named Raj Agarwal who like, had, you know, I owe him a lot for this of kind of like sitting me down. And I still remember he called and he was just kind of like, this is not going to work the way you're doing it. You know, like, you're. This is not going to happen. And thank goodness he did that because otherwise you can continue. You lie to yourself. I mean, I was definitely lying to myself on like, oh, I got it, it's fine. And like, it's such a different scale, Alex, than what you were talking about for like yours, you know, but it was the same thing of like pretending like it was okay, you know, when in fact it wasn't. Yeah. And like, to his credit, he kind of told me, like, is not. And at that point you kind of either have to go back to the other side or you have to like, learn how to do this one. And I tried to learn how to do this one.

The good news Is you're used to being sat down. Stop taking nothing away.

Sat down a few times.

I sense a theme.

You're not afraid to be sat down. That's right. And you know, funny enough, Raj, my dad's name is Raj, so was my brother. So people named Raj tend to sit me down.

I want to hear about two lions that, that influence you. Henry Kravis, George Roberts. Yeah, I mean.

Oh, yeah.

Two of the OGs of OGs.

Yeah.

Right. And so I'm sure they also sat you down.

Oh, yeah.

At some point. And imparted some wisdom. So tell us about your relationship with, with those two gentlemen.

And so Henry Krause, George Roberts are the founders at kkr. The founders of private equity, basically. Right. And they're just incredible, right? So when I went to KKR was only 250 people, very small. And so everybody got to like spend time with them, you know, and like, what a treat, you know, like what a treat to like spend time with them. And actually you guys both know them, you know, and like, I understand, right?

Like the New York office is Henry's, right. And the Barry office is George's. And they have kind of a little different vibe, right?

Oh, yeah. I mean, at the time, New York, all suit and tie, okay. Like, it's like you're in a museum when you're in there, like, crazy, crazy, like old art. It's like very ornate, incredible view of Central Park. I mean, there was like a wait staff, like a full time wait staff in the office where like, if you press a button, people would come and like bring you like, I'm talking like, literally food on a silver platter. Okay? That's what New York was like. Like, it is the craziest experience ever. And like, it's funny because, like, if you were. I wasn't a partner when I was in New York and so the partners had like the real, like the real setup. You still had an amazing setup if you weren't. But you try to like be in their offices around lunchtime so that they could like press a button and be like, do you want something? But yeah, I do. But Henry was always, he was always very good to me. And honestly, I'm not really sure why. Like, I don't really know what made him take a liking to me or not, but he always had time for me, which is crazy, right? Cause like, I was a nobody. Like, and still a nobody, but particularly a nobody. Like, I had just gotten there. But if I ever was, like, can I come see you? He'd be like, yeah, he would have lunch with me. He would talk to me. And if you were curious, that was like. He was just, like, so ready to spend time, you know? And that is, like, such a cool trait. You know, Henry Carter's on top of the world, like, multi billionaire. Everyone wants his time. But if you were, like, sincerely curious, he was willing to hang. And so I'd say what Henry taught me in that time is, like, looking back, he taught me to be gracious to young people. He really seeks out young people, you know, you and I talked about this for George. Like, they both do that. And then the other thing was, when I left, he gave me probably one of the coolest speeches that I've ever heard, right? And he basically, like, I thought he was gonna try and convince me to stay, and he didn't. He, in fact, was sort of like, I respect that you want to go do something, like, more entrepreneurial, you know? And he. What he said was, he was like, look, like you're going to have these moments where you want to come back because it's going to be hard. And he's like, just remember, your job is not to, like, do the easy thing. Your job is like, get on the boat and get the boat to the other side. This is like, before I left, you know? And I remember, like, whoa. And then the other thing he said, which is crazy. Like, all of us are working to get to a career that's a hundredth of Henry's, right? And in his office. And Henry's office, comically big, like, is huge. It's a huge office, okay? And it has, like, the most sprawling view of Central park you've ever seen in your life. It's insane. He's got, like, pictures of him with presidents everywhere. It's just crazy. So, like, it's like, such, like a. You're never gonna get here office, okay? And at that point, though, he says to me, he's like, hey, as I'm walking, I said, how old are you? At the time, I was 33. So I'm 33. And he, like, put his head back, and he goes, oh, I would do anything to be 33. And you just think about it. It's like, such, like, a life lesson of, like, this guy who has the, like, the business career, the most hall of fame business career, like, you could imagine. And all he's saying is, like, man, it'd be cool to be younger again. And he would just, like, do it again. And what an amazing. That was, like, very affecting. You know, I'M like, I'm, you know, chills right now. Talking about. George is different. George is amazing, too, but George is more like, you got to work for it a little bit more with George, you know? And so George was always, like, the one who made a lot of the investment decisions at kkr, like, kind of like, final say, you know? And you think about, like, the size of that firm and, like, how much he was doing, it's crazy. And George a little bit more like, he's quieter. Henry's gregarious. George is quieter, you know, and if you ask a dumb question, he doesn't quite let you know about it, but you kind of know that he's like, what are we talking about?

You know?

But the thing that he was is, like, he was he actually funny enough. He was he. Same thing. He's very. He's very honest, but he was willing to give you tough news. Like, he actually didn't think Instacart was a good business. So he's sort of like, yeah, like, I get it that you want to go do this, but, like, I don't think that's very good business. And you know what? He was right at the time. It was not a good business, and, like, it turned into a great business, and it is amazing business now. But it was a little bit like, look, if you're gonna do it, why do it there?

Yeah.

And, like, you know, again, like, I didn't want to hear that then, but I learned, like, that's a hard thing to tell somebody who's, like, already decided they're leaving, whatever. But he was like, that's the way he shows that he cares. He, like, actually will tell you. But the thing that I pair that with is when I left and I asked him, like, six, nine months later if I could come back and talk to him about it. He was like, yeah, of course. Just come on back. And then he, like, gave me advice.

Wow.

And even though he didn't think that it was a good business at the time and any of that and, like, how cool is that?

How long have you been curious about going and, you know, jumping over to the startup side?

Totally. A long time. Not just startups, but, like, I always thought I wanted to help run a company, you know, like, ever since I got to McKinsey.

On that note, the. Did you go initially CFO? I don't even know.

Yeah.

Or both titles?

No, just cfo.

Okay. And, like, did one of those, like.

Oh, yeah, I'll tell you guys now, like, yeah, this is. So this was Funny. So the relevance here is we lived in New York for nine of the 10 years I was a KKR, okay? And we moved when Avni finished her fellowship. We actually moved to California mainly because she got her, like, physician job she still has in California. And KKR offices in New York and California, we're like, let's go, like, settle there. So we moved. Not for Instacart, we moved, like, for Avni's job. And then, like, I was still at kkr, and basically, you get to California, and tech is just, like, so central, right? Like, you know, in New York, finance is really central. In California, tech is so central. And again, like, on. Like, some things are not great. Like, I didn't. I noticed that, like, I had a job that was, like, not interesting relative to, like, the community, you know? And, like, look, man, this is real. Like, you know, this is true, you.

Know, You're a banker.

Exactly. You're one of those. And I'm like, okay. You know, like, and. And I'm sure I was overthinking that because, like, you know, it's so dumb when you say things for, like, a cocktail party, because I'm like, I don't think I've been to a cocktail party in years. You know what I'm saying? Like, so dumb. But I think she think the good part of it was, like, I think I just was a lot of, like, man, like, I don't think I'll like, living in Silicon Valley and not seeing what tech is like, you know, like, it was so Central. It was 2015, so it's funny. So we can't hear you all have lunch together, okay? Every day. So George's office in Menlo. So, I mean, lunch. And one of the guys, one of the senior capstone guys, had come to lunch, and as he's walking out, he's like, oh, you know, I got this call from Instacart, and I was like, what do you mean? I knew Instacart would use it as a customer. He's like, oh, they called me. A recruiter called me to interview for their CFO position. And at this point, like, I should be happy for the guy because it's, like, cool. I'm just pissed, you know, I'm like, man, nobody called me. And, like, I'm not getting any calls. Like, you know, like, people have these stories. Like, recruiters call me all the time. Like, I had no recruiters calling. Like, none. It's like, maybe my phone number was not in the directory. Like, nobody. And I'm kind Of like, what is going on? Where, like, he's getting a call for like a C level title, and I'm not getting calls for anything.

You know, Some of us don't get the D1 offers.

All the offers, you know.

That's right.

That's right. Shane doesn't understand because he was the third.

No, yeah.

Fourth highest rated seventh grader. Is that right?

I went into the front door.

Some of us are, you know.

Yeah, exactly. So anyway, so. So I. I followed this guy back to his office, Derek. And I'm like, yo, man, like, are you going to take it? And he's like, I don't know if I'm going to get it. I'm like, no, no, no, but if you get it, are you going to take it? And he's like, you know what? I don't think so. There's too much risk. And I was like, okay, cool. Can you tell him to call me? And he's like, do you want to take it? And I'm like, I just know I want them to want me. I don't know if I want to take it, but I want them to want me. Cool. So he's like, I'll call the recruiter. So anyway, one day goes by, two days go by, three days go by, no call from the recruiter. So I called Derek again. I'm like, hey, man, did you tell the recruiters? Like, yeah, I did. He's like, they're actually not going to call you. I'm like, why not? Like, what? They called you? Why? Why would they not call me? Like, what? What could possibly. We have, like, such similar backgrounds. He's like, I was kind of like the weird candidate. He's like. And like, because I'm not going to do it, the surgeon not going that great. Like, they're not going to send another weird candidate. And I'm like, Because, I mean, I have no experience, remember? Like, I'm like, I was just like.

At this point, do you know you could go crush this job?

Or I would say one thing. You know, you talked about, like, being sat down. I think I had some like, Vernon Maxwell irrational confidence of like, yeah, I could do this. No, it's funny, like, literally the job description, Alex, I hadn't seen it, but if you looked at it, like, I don't think I have met any of the criteria. It was like, you know, 10 years of operating experience, probably wanted a graduate degree, probably CFO experience, maybe having taken a company public. I haven't. I've never worked at a company. I'VE never worked anywhere. You know what I'm saying?

This is an insane hire. This is an insane hire. You know this.

I agree. I agree, I agree, I agree. So this is why. But I'm pissed that they're not calling me. That, like, tells you something, you know? And so I go. And so he's like, they're not gonna call you. So I go and look up this recruiter's name, okay? And I don't have any mutual connection with him on LinkedIn. I look up his boss, the guy whose name's on the door. I have one mutual connection with him, okay? So I call that guy and I'm like, yo, can you call this recruiter and tell him I'm smart? And he's like, why? I'm like, because he's doing this search and they won't call me. And he's like, do you want to do. I'm like, no, but I want them to want me, okay? So he calls his recruiter. Great. The boss. Boss meets me at the Sharon Heights Starbucks. Okay, cool. Sits down with me. And he's like, I'm not going to put you in front of this job. I'm like, what is going on? You know? And he's like, look, people never leave these jobs. Like, they never leave the private. They all think they want to go work somewhere, but they never leave. So he doesn't put me in touch. I'm like, man, I'm really. I have no path. So I go. Go look up Instacart's investors. Mind you, I have no idea. There's not no other company, just one company, okay? I look up all of Instacart's investors, and I'm not like, in the tech world, I don't know anybody, but I know one guy at one firm in New York, okay? So I email this guy, hey, man, I'll be in New York next week. You want to get coffee? And he's like, I was no plans to be in New York. He's like, yeah, why don't we get together on Wednesday? I'm like, cool, book my travel. I go see him. Okay. And so we go and, like, probably 50 minutes into the meeting, I'm just waiting to kind of wait to talk about Instacart. Finally. He's like, when are you finally going to leave kkr? This is some dude I just met in New York. And I was like, when are you going to get me a job? One of these portfolio companies of yours? And he's like, oh. Huh. And he's like, he brings up one company, and he's like, not Instacart. And I'm like, I don't know. And then I'm like, I heard Instacart's looking for a cfo. And he, like, long pause. He's like, oh, actually, he's like, yeah. Huh. And, like, then he goes, why don't I put you in touch with the recruiter? And I'm like, I don't know if that's gonna work. And so then I had to, like, am I gonna come clean? Am I not? And I was kinda like, well, I met with him, and, you know, and then at this point, it's like a big moment. Cause it's like, does he throw it away or not? And to his credit, on this insane hire, this guy who was an investor in the company, he's like, what if I email the founder directly? I'm like, you know, I think that might work. And he what? He emailed the founder, which is such so much. So lucky for me was, hey, I've been trying to recruit Revi for a long time. I don't think you'll be able to get him, but you should talk to him. Which, by the way, that is so nice to me, right? Like, I've been begging to get an interview at this place, and now I get positioned as, like, somebody who's hard to get. All of a sudden, meeting with the founder. Two days later, a couple weeks go by, I get the offer, right, as cfo. And it was same kind of thing of, like, Alex, to your point, I'm like, did you know you could do it any of that? Like, I was bold. I mean, you know, when he was talking to me, he's like, do you want to do this? I'm like, well, I don't want to be, like, a bean counter, you know, Like, I want to help you, like, run this thing. And so if you're looking for somebody to, like, be a strategic partner, like, I'm interested. If you're looking for someone to, like, take you public and count the beans, like, I'm not. I don't even know how to do that. Like, you know, I told him, I was like, if you're looking for something, like, close the books, like, I don't know how to do that. I'm like, I literally don't even quite know what that means to close the books. Like, because, you know, you know, like, and so. And my. My wife, you know, so funny.

And there's kind of two style of cfo, right? Like, like, for sure. One or the other.

Yeah, exactly. And, like, you know, so I was trying to position myself more as, like, a business partner CFO rather than, like, you know, keep score. Cfo. Yeah. So anyway, he ended up giving me the offer, and I took it and I joined a CFO in September of 2015. And that is, like, a fun journey and all that stuff, but, like, yeah, it was crazy to even get there.

And things aren't going great when you join the team.

Right.

Real quick, I just.

Where do you think this. Like, where did the spark come from for this? Like, this determination?

Yeah.

Right. Like, that's what I. Like, you're at. You're at this great job. Right. KKR Private Equity. Things are going smoothly. You moved over to the. The A team on the investing side, and, you know, you're cruising along like. Yeah, you talked about. I mean, it's a. It's a great place to work. Like, it's. It's awesome. Tons of people kill for that job.

Totally.

And yet something.

Yes.

Right. Like, sparked this.

Yeah.

You move out to. You kind of talked about, like, but what do you think that thing was where you freaking flew? You booked a ticket to New York to have coffee to hunt this job.

Down, and then, you know, you didn't.

Even know if you really wanted. But, like, something total here pissed you off.

Yes.

Right. Like, we talk about edge all the time.

Yes.

Like, where did that. Yeah, where do you think this. Like, where did it start?

Yeah. So when I was growing up, my dad used to talk, like, positively about people that ran companies. So I just think those words were something that, like, there was respect from the person I respected the most for that, you know? So I think that was always in my head of, like, that would be something that'd be cool. I think the thing that pissed me off, Alex, was like, I knew people at companies. You asked, like, where the conference come from, and I was kind of like, I can do that. You know, but then there was no opportunity coming. Zero. Zero. And I think that that did piss me off. And then I'm. In retrospect, I'm happy. I'm like, let me go do something about it. Rather than kind of like, just being mad. But also, like, people lie about the way these things work. Like, I thought that you just, like, sit at your desk and then, like, Sundar Pichai calls you and he's like, yeah, maybe you want to run, like, a big part of Google. Like, that's the way everybody tells their stories. You know, you always talk about people do what you love. Follow your passion. People are always like, oh, yeah, no, I wasn't thinking about it. And then, you know, they then, yeah, totally. Yeah. Seth Anadella called me and was like, why don't you be the president of Microsoft? And it's like, well, I don't know anything about technology. It's like, no, that's not how it works at all. But I think what pissed me off was just that, like, I wasn't getting any of these opportunities, and I thought I could do it. I still think to this day, job descriptions are the dumbest things in the world. They have nothing to do with what actually matters in the job, Right? And so they just, like, fill out this boilerplate language. So I truly was just like, I don't. I don't accept that that is actually, like, the requirements for this job. But I think that, yeah, like, that's what pissed me off. And then the other thing is Avni, to her extreme credit, like, when I got the offer, I mean, it was a 90% pay cut. It was like a. That's a big deal, you know? And I was like, oh, man, I don't know if I can do that. You know? And Avni was like, listen, like, I think you're a crazy person for wanting to go do this job. Like, to be clear, like, I don't. I don't understand why you would want to do it, because you have this good thing. We have this thing. She's like, but I do think you want it, and I do think that you're going to regret if you don't do it. So I think you got to do it. And so just, like, the separation, you know, for that and like, the kind of, gosh, you're lucky I sat down again.

She sat you down.

But the. Like, I think that the. Try to live without regret. That was a big part. And then another thing that was a big deal was I think people massively overestimate risk. Realistically, if the instacart thing didn't work out, I'm probably not gonna, like, go live in a box, you know? Like, there's probably some job I could go do. So, like, when I was, like, evaluating, like, what is the cost of leaving? The cost. Leaving is leaving kkr. It's amazing job, all that stuff. But it's probably not that you can't, like, recreate any job. You know what I'm saying? And so I think that that was something that I realized later. But I do think people dramatically overestimate, you know, risk.

Do you Think your time at KKR dealing with a bunch of companies that you guys had, like, obviously invested and taken, you know, over or whatever, and being around these operators.

Yeah.

Did that give you the confidence that, like, I can. I, you know, like, because it's free for me to go operate a private company.

Yeah.

Like you were doing. There's like this, there's this magic to it. There's only so many people in the world that have done it and can do it right. And it's like this exclusive kind of behind the curtains thing. Did that give you a glimpse of like, no, I can freaking go do this?

Like, Yeah, I think.

Have you been around enough operators that at that point, for sure.

But I also think, I think it also came. So there's one in particular, this guy named David Campbell, who I really looked up to, who led one of the companies KKR had invested in. And he had become a mentor. And I really liked how he did it. And so I saw that for sure, that helped. Also. You talked about cultural stuff. I actually think part of the reason my dad wasn't able to do that was some stuff that was out of his control. And so I do think part of it was also, like, I thought it would make my dad proud, you know, of like, hey, we're doing it. I thought he would love. When I called him, hey, what should I do about this? You know, it was true. My, my dad loves when I call him up business stuff. But I also think that it was like, partly something I think he always thought he'd be good at, you know, and so I wanted to, I wanted to do it for me. But like, a really nice ancillary benefit was I thought that, like, did it for him. Yeah, I could do it with him. And like, there's. This is a ridiculous, ridiculous, ridiculous story. But I always got goosebumps in, like there's this 30 for 30 where Jordan rides the bus, you know, like that when he went and played baseball.

Yeah.

And he used to talk that he would, like, when he was driving to the stadium, his dad had died. Like, he would be like, dad, we're really doing it because, you know, his dad always wanted him to play baseball. And I love that story. Right. Because I think, like, even as a grown up, there's so much of like, you know, your parents that like, matter, you know. And like. Yeah, I think it was partly like his dream, you know, he would never say that. Yeah. But I'm sure that was part of it.

Yeah.

That's awesome.

So walk us in the first Day of Instacart. Yeah, yeah, yeah. You don't know what you're getting into. All right. Because it did not go well.

No.

Initially.

Right.

So, you know, to our, to our glue guys audience out there and where.

Are they at at this point?

Like, scale wise, you know, it's like this dichotomy, right? Like, the valuation is $2 billion that had been named Fortune or Forbes, like, most promising startups, by the way. Like, and I know that we say this already, but, like, Instacart is an amazing public company now. This is like a hundred years ago. And like, now it's incredible. But at the time, yeah, like, it was big valuation, but, like, I mean, we were tiny. We were so small in terms of revenue, like, you know, low double digit. I mean, we had like $15 million of annualized revenue, you know, and like, we had like a few thousand shoppers, you know, that are delivering the groceries. We're in a few cities and we are losing money. Hand over this time. So much.

So much.

Yeah, I mean, so. Yeah. So I got. I started on September 28, 2015. On Halloween, I got the financials from the controller and first thing I did was called him, being like, yo, man, can you please send me the right ones? Oh, I'm so frustrated because it's like I can't even get accurate financials. And he's like, well, what do you think is wrong with them? And I'm like, this says we're burning $12 million every month. 12 million bucks a month. And says we're going to go out of business in less than a year, like, obviously. And we're losing $16 every time we do an order. $16 every time. Like, every time we do an order to give somebody 16 bucks, like, you have to be a CFO. You're not going to grow your way.

Out of that, right?

Like, that's not like the path. And so then he's like, no, that's right. And I'm like, oh, oh, my God. And this one, you're all like, life splashing before your eyes. Just like, what do I do? Is you full, like, fight or flight? And I'm like, flight, Flight. I got to get out of here. You know, I still remember, like, the version of this that I was like, the funniest part to me, and I told you guys this before. I, like, remember thinking about, like, what I would Write on my LinkedIn so that, like, it didn't look like a Gap. I was like, well, like, if I leave today and I could say That I worked at KKR through September, you know, and then, like, maybe, like, I can just be like, back, you know, like, no break, because it's technically just one month gone. I mean, I was really going through, like, whatever. But the real thing that happened was, like, we actually had a board meeting on. I believe it was November 5th. I have this document on my desktop, like, my work. My computer has a clean desktop. Other than. I just keep this file from the first Instacart board meeting on it as a reminder of. Look at what this was. This guy who had come with me, this guy Sagar Sanghvi, he and I worked on this board deck because I was like, even if I'm thinking about leaving, I have to tell people what the heck's going on. And when we went through it, all of a sudden it was like, hey, there's some path. If we did this, if we did this, if we did this, if we did this, huh? Like, maybe there's something. Maybe there's some path out. And he deserves a lot of credit because, like, with the two of us working on it together, along with the whole team, you realize there was some map that could possibly make it better. Because the first thing you have to do is not lose all the money you got to get out of that. You cannot be losing money on every order and have any chance. It's like, there's only. My kids laugh, but there's two. When I teach them about business, I was like, there's two things that matter. And the first one is stolen from Y Combinator, which is make something people want. And the second thing is you've got to sell it for more than you make it for. Yeah, those are the only. Like, every. After that, you're good. And so we were violating. We were making so many people one of them. We were violating that. So, like, we then did, like, 15 months of just, like, awesome work. Just, like, awesome work. The team was amazing. We had 300 people, and everybody's rowing in the same direction. Like, just like, all we're doing is getting is improving the unit economics of the business. And, like, it's so nerdy. But it was so fun, you know, to, like, everybody working on one thing. You have people high fiving in the hallways when they, like, fine, like, 30 cents on an order. And then, like, there was this great people coming up with new ideas. There's this great thing where, like, we realized that every minute that a delivery took was worth 25 cents, right? And so we got everyone T shirts that said, every minute counts. And I used to joke that mine on the back should say exactly this much. So you'd find people, they'd be like, well, what if we get free? What if we get instacart labeled parking spaces at the store? We'll shave three minutes. What if we batch delivery? We'll shave this many minutes. You know, what if we get our own checkout lines and you just have people just, like, ringing up minutes? And this answer of, like, figuring out how to motivate people was one of, like, the coolest things ever. Like, as a team, we did this, but, like, everybody, nobody in a business cares about finance. Yeah, right. Nobody cares about the financials. People care about serving customers. They care about being great. They care about excellence and being able to figure out the language. Because you're going like, we gotta be profitable. Nobody cares, Right? If you're like, we can be better. We're a delivery. We're a logistics company, we're a software company, and we're not great at this thing. We can be so much faster to our customers. Everybody wants to work on that. And so all of a sudden, it used to take us 110 minutes to do a delivery all in. At, you know, 15 months later, it's taking us 64 minutes to do a delivery. But that 46 minutes of difference. Right, was worth, like, $11.50 of improvement in the economics. Like, it's amazing. And so that period of time was just, like, so fun, and it taught me, like, so much about. That's the closest that I think you can feel in a business environment. Like a startup is the closest you can feel to a sports team, because you can have shared purpose. You can all be doing the same thing. You can all. You only get paid if it all works, that kind of thing.

But you're not just, like, counting the beans at this point.

No. So then nine months later, I got named COO as well. So I was our COO and cfo, which is, like, real, very proud. I was. I felt like, to your point, Alex, most promotions. And people get this wrong. Most promotions come. You're already doing the other job. It's a recognition of what's already happening.

Job description out the window.

Exactly. Yeah, exactly. And so when I was named COO and cfo, that was really cool. I was very proud because I felt like it was like, this is what I wanted to do. I wanted to help run the company.

So what changed? All right, you're losing 16 bucks an order.

Okay.

And all of a sudden, what's the message to Your people to allow them to innovate and be part of the solution.

Yeah.

Like, what changed?

Yeah.

Was it, was it communication? Was it the T shirts? Like, what was the things that you did?

Yeah, it was focus, focus, focus, focus, focus, focus. Which was that, like, instead of working on 10 things, we're working on one thing. Yeah, it was. And it was like, life or death for the sake of the company. Of, like, we have to fix this. But there was, like, optimism of, like, the race is worth running if we fix this. Like, what we would tell people, which I, I, I believed, which is like, it's so hard to make something that anybody ever wants to use. A consumer product that people want to use is insane.

Yeah.

Like, I remember when I was thinking about Instacart, Avni said I wouldn't move unless Instacart delivered to the new house. Like, literally, that's how much she loved this product.

Yeah.

And, like, it gave us more time at home with our family. Like, just, like, people loved it. Yeah. And so I would tell people, and the whole leadership team would tell people, like, you've done the thing that's impossible, which is make something that means something to people. How many things would you, like, care about and love? You know what I'm saying? That people measure nps, but I'm talking, like, real love. It's like, you've done that.

Yeah.

If we just make it a real business, you have no idea where this thing can go. Right. It could be, it can be so impactful to people. You can give back people so much time with their families. You can do so much, but we just got to turn it into a business and nothing else matters other than that. So the first thing was just, like, focus. And then the second thing, Jane, I'm so happy you asked about, like, what gave people the space to innovate. You have to ask the right question as a leader. Right. You don't give them the answer. Here's what you need to go do. Go do a Swede. It's like, okay, look, you're not allowed to raise the prices of the customer. You're not allowed to raise the price to the retailer. Right. And you're not allowed to pay the shoppers less. Those are the three constraints. Yeah. And now we have to make a lot more money on every order. How are we going to do that?

Figure it out.

Well, that is a very hard job. Right. But then people come up with amazing ideas. I still remember somebody coming up to me being like, hey, I know you said we couldn't charge more. And I was like, right, that's a constraint. And they're like, but I noticed that we're not charging sales tax properly. We're not accurate in what we charge. We undercharge sales tax. Does that count as charging customers more? I'm like, no. Thank you so much for asking. You are brilliant. I have no idea how you figured out that we weren't charging sales tax properly. But, like, that was, you know, some number of cents per order. Somebody noticed we weren't charging bottle deposits, like, which you, like, get charged with the store. There's just like, so. And somebody was like, well, what if we start advertising, you know, for CPG companies? Like, basically, like, if you search for Pepsi, maybe Coke would want to buy an ad. I was like, that is such an amazing idea. And there's like, so the people, when asked the right question, they show you these things that you're just like, oh, my God, you know? And then the same thing when we said, how can you take minutes out of delivery? The ideas that would come back were so cool, and people were so proud. So the thing that changed, Shane, was focus. And then metrics, like, real clarity around how are we doing? And people loved it every week, okay, we did this. This is how we got here. This is how we got here. And it's one of the proudest things ever for me, that it's not about the unit economics. It was like turning something that was a product into a business. And that group, they did it. And it was so hard, but it was, like, so earned, you know, after that. And then just when you think you're, like, out of it, you're like, okay, cool, we did that. Great. Now we just get to, like, roll. Then fucking Jeff Bezos punches us in the face, you know? Totally, totally.

I think it's such a cool story, though. I think so many people, again, like, just see, like, the final product, right? And they don't like the journey. And I think sometimes, I mean, obviously there's like, the saying, right? Like, you can't see your way out of the woods, but it doesn't. You don't have to. You just have to see, like, that first step. And I love, like, the idea of you guys got to make up 16, right?

And plus. Yeah, yeah, plus. That's just. We have to, like, make money.

Make up 16.

But the idea that. And it kind of reminded me a little bit, like, honestly, like, my rehab, like, these, like, little tangible goals that you can, like, that are attainable and you can get and celebrate.

Yes.

Right. Like, and even again as a team, like, yeah. You know, like, yes. Hey, it's a couple cents. Like, that's a freaking victory, man. Like, you know, like, celebrating it and then what's next?

Yes.

Right. Like, okay, what's next? And just that focus. That, like, singular focus, I think is so cool.

The original name for the project to, like, get the unit economics to be better was Project Pacino. And because we did the. You know, on this team, we fight for that.

Yeah.

Literally the name of it. But you're so right, dude. Like, and the other thing is, it's so fun to watch people succeed when they earn it, you know, and then to do it together. Like, it's just. It's so good. It's so good. This is why, like, you know, you guys joke that, like. Like, well, the reason Instacart is my favorite team is because the ipo. I was like, no, it's not. Sure. Like, that is amazing. That's great. Okay. But, like, the reason it's my favorite team is because we, like, did something, you know, and it's the time where you feel, like, very alive, that you're, like, contributing and you're part of it. And, like, it's awesome.

I think there's something to, like, momentum, too, with that.

Oh.

When you get one, you know, like, little. Those little. It's important, I think sometimes when, like, something seems so far away.

Yes.

And hard to get.

Yes.

That these little. You break it down.

Totally get it.

So important. I think when Sometimes people set lofty goals, I think is great.

Yeah.

Right. But, like, you can't. You weren't, like, going into work, like.

No.

Thinking about. Yeah. You can't skip 16 bucks. You know what I'm saying? Like, you got to just. Anyway.

Yeah. I think it's so you. So you slay the Death Star.

Okay.

Like, talk about that. When did that happen?

We're cruising along. Yes, we're cruising along.

Okay.

We got back to break even.

Yeah.

Okay.

We raised some money. You know, we like it. Done another round. All these, like, great milestones.

So you're. You're cruising, and all of a sudden, you know, Darth Vader comes in, enters the picture.

The White Walkers.

The White Walkers appear on the horizon.

Yeah.

So this is kind of an oh, shit moment for everybody.

Oh, every swear word.

Amazon. So walk us through that day where Amazon announces their. Their purchase of Whole Foods.

Crazy. Yeah. So I remember we had actually just got back from a trip to see a bunch of grocers. We had a ton of momentum Instacart is like, Instacart partnership with grocers is critical. Like, it's a huge deal, basically. Like, it is such, like, a symbiotic thing. And so the more grocers you can have on Instacart, the better the business is because, you know, it's better options for customers. Okay, so we just go on and seen, like, a bunch of them, and some of them were reluctant early on, but we were, like, making progress. So we're like, oh. So we were feeling like we had mojo, and we had just gotten back, and we're like, yes. So I remember waking up, you know, and Avni had gone to, like, brush her teeth, and she saw me at the edge of the bed, and I'm just, like, looking at my phone, shaking my head. I had 253 text messages, okay? And, like, dude, like, that is not like, the normal flow of text unless it's, like, during fantasy football season or something. Like, you know, but, like, I wait. I'm like, who died? Like, what happened? And, like, there's all these texts, and the best one is from my mom, which just says, are you okay? That's the entire body of the text. I was like, what? And I go and I look and I see that, like, Amazon has bought Whole Foods, and it's everywhere and is.

Entering the home delivery. Oh, yeah.

Like, the entire thing was, like, in. They. I mean, they were. They had this thing Amazon Fresh, which, like, basically what was happening was they had this thing, and it, like, wasn't that great. But they're. They're always, like, lurking. And when they buy Whole Foods, you can just go through all this scenario. It's such an amazing company. You're like, oh, God. You know, like, they're coming for real. Like, this is a big. It was their biggest acquisition ever. Like, they paid $13 billion. It was like, we're coming. And so at that point, you're like. I mean, you're freaked out, right? I certainly was freaked out. All of us are freaked out. But then the thing is, like, what are we gonna tell the team? Like, we have to tell them something. We talk about not being scared as a leader. Like, you can't just go up there and be like, guys, we're fucked. You can't do that. And so we're like, oh, my God. So we, like, go in the office, we get in, like, a war room, you know, and there's all these, like, business war analogies, but they're obviously absurd. But, like, whatever. We, like, get in this. We're like, what are we going to say? We got to, like, get in front of people. We got to get in front of people, like 10:00am, you know, because it's like, we got news, like, 6, 6:30. So, like, get into the office. We're sitting there. And one of the things that was actually kind of cool was Mike Moritz, who's from Sequoia, who's our board member. A bunch of investors had texted us, like, effectively, like, what does this mean for their money? Which is like the worst thing. Like, they're worried about themselves. Self interest, you know, like, it just like, so, so revealing. Non glue. Hey, hey. I own, you know, 0.04% of Instacart. Like, what should I tell my partners on what's going to happen? I'm like, I don't care. What are you talking about? And so Moritz, though, to his eternal credit, texted us and said, what do you need? Such a good question. What do you need? And we're like, we don't know. And he's like, I'll come to the office. Comes to the office. He's a former journalist. So we're sitting there and we're like, trying to come up with what we're going to tell the team. They were coming up with that. And then Moritz pulls out his computer and he writes our press release. And think about, like, this. Cool, right? This guy's like multi billionaire, right? He's a knight, you know, and he's just like, sitting there with us, you know, and he's just like, on his computer typing it himself, okay? And I'll tell you what we said to the team. His language was much better because he's former journalist. He's amazing. You know, whatever. You should read his books if you have. They're so good. Anyway, it's like Amazon just declared war on every corner store and grocery store in America, right? We at instacart and our 180 partners stand ready to help every, you know, grocery store and corner store in this battle, you know? And so it's like, put us on our front foot. And, like, honestly, like, as a leader, he, like, gave us courage, you know, like, we're like, well, he, he believes and like, yeah, we are going to do that, you know? And, like, even though we didn't totally believe it, just, like, he'd seen stuff, you know, and like, but even, like, I felt proud when that it wasn't like, we don't know what we're gonna do in the press release. But he was like, no, we're going and doing this. This is a moment for us. Then we went out in front of the team. We're like, look, all these grocers that haven't worked with us before, they're gonna wanna work with us now. We're in this together now, right? This is real. We're in this together now. And your work matters. You're in the arena. This is. We leaned into that, right? Of like, you'd so much rather be in this than outside of it.

You're on the wall now.

You're on the wall and we can do it. We are ready for this. You know, like, we just. And the thing that was so cool was having come through the 16 loss, we're like, you know what? We're hardened a little bit. Like, we've been through some stuff and then, you know, I've talked about this so many times, but Shane, you sent that email to me, right? The. And it was great. Like the telling the stories of your own life and, you know, resilience. And then also the line at the end of, you know, you have a chance to become anti fragile. How lucky are you? I mean, like, that's like real friendship. And it made a big difference. I shared it to the team, you know, like, check this out, you know. But that was like crazy because then again, like, it's sort of a consistent. Like just when you think you're done, it starts again. And I'll tell you, like, the thing that's so crazy is like, Instacart's an amazing business now, but they have their challenges now that they are overcoming. And Fiji, our CEO, she's so good. She's so good. I really. And like, it's not a finished product even now because all of a sudden just the bar keeps getting raised. The ambition is even higher. But going back to the Amazon thing, like, then again, like 12 months signing every grocer, and all of a sudden we got every major grocer in the country to come join Instacarts, you know, like, marketplace. So huge deal. And it's crazy, like, the Amazon thing made us better all of a sudden, this crazy competitor coming in, but it made our product better. And this is honestly one of the, like, the geniuses. The genius things of Bezos is like, he's able to articulate, like, what competition does. Like, the winner is the consumer, right? Amazon did something really terrible and hard and the consumer won because all of a sudden our product got better. You know what I'm saying? And we got better because we had to like, play you know, and we had to play at our best. And it was so fun because, like, all of a sudden we turned into business development people. You know, we're like flying around, meeting with all these grocery execs and grocery stores are not in fancy places. You know, like, to go back to.

The day when Amazon declared kind of war.

What.

How did that all hands go? Like, how did the team receive your guys's message?

They wanted more specifics.

Did you guys go get like, Amazon urinal cakes? And like, this would be like a football move. This is like the Urban Meyer. So, you know, Utah's. Utah's rivals byu. And he got this from his days at Ohio State when. Yeah, I think Woody Hayes, like, you didn't mention Michigan. You didn't say it. And so he brought it to us. It was just the team down south. So he didn't even say. And he had. We had cougar urinal cakes.

That is cougar.

I mean, it was like everywhere.

I can't wait for the next. But the next board meeting I'm in with any company, I'll be like, hey, where are we at on urinal cakes with our competitors? So, no, we did not. I wish we had thought of that. You know, it's funny, Alex, the first thing, all we tried to do the first day was like, give them the words that they could tell their parents. You think about it, right? Because, like, what really happens in that moment is like, everybody who loves them is like, you need to get out of here, right? You don't want to be part of that. So the first thing that. That first all hands was just like, it's going to be fine. Here's the things that are going to happen. And so much of like, there's a path for optimism, right? But I would tell you, like, mostly the feedback we got afterwards, like, this is great. Like, what's the plan? Right? And so the next week we sat and just like, came up with it. And this is where in our invest like the best. I talked about Michelle Sawanicle as this incredible teammate that I had. And she was like the heartbeat. She was. She had the pulse. She just knew what the organization needs. So she was in the room with us, even though, like, her title wouldn't have said that, but she was in the room with us of just like, this is what the people need to hear. You're not being specific enough. What are they going to do here? When are we going to report on this? What does success look like? You know, like, and that was so cool. So valuable. And you need that. Like, I used to have Michelle interview every person that we that I ever interviewed, even if she had nothing to do with the position, just because, like, is this going to work? You know, but like, that kind of thing. Alex, like, the first all hands, I would say, like, it did the job of like, we're going to be okay. But people afterwards were like, what do I do tomorrow as a result of this? And that's what we had to give him was like a much more detailed plan. And, you know, this, like, we talk about coaches all the time. Like, the rah rah only goes so far. Right? Like, you got to demonstrate competence. You have to have the plan, you know? And honestly, Shane, I never heard this, but the Van Gundy thing of like, you know, don't fail the plan, let the plan fail you. A lot of that second all hands was that.

Yeah.

Hey, listen, don't worry about the things we told you were important yesterday. This is important now. And if you do this, we're going to be good. Right? Like, and so everybody's work. One of the big things that happens in startup is you got to be ready to change on a dime. Yeah. Remember, every priority, you have all of a sudden turned upside down. You know, and one thing I think Instacart is very good at is it is a resilient company. It is a. And I feel real pride in that, you know, Like, I feel real pride that, like today, whatever happens, you get punched in the face. Like, Instacart has. Has history of, like, we can figure this out. Part of it's because they're nimble.

Please, please, please tell us your Jeff Bezos story. Like, so you know, Bezos comes. Comes around the corner, huffing and puffing. All right? You stand up. You stand up to the bully. And this is when you really, really knew that you were doing something that.

We got on his radar. Yeah, yeah, yeah. One of our investors had this CEO summit where they had all their CEOs come and they asked us to come talk. Honestly, I bet you they asked our founder Apoorva, and he probably said no. And then I went as like, the backup, I'm sure. But whatever, I went and I gave like a fireside chat there. And so when I was going, I still remember, like, you know, I actually have the picture of the agenda. I, like, found it in my phone. I have, like, the picture of the agenda, but I still remember looking through it like, oh, I wonder, like, you know, where I am in the stack or whatever. And the person Right after me, who was going to be talking was Jeff Bezos. And I was like, whoa. I mean, you know, that's not my typical follow up, you know, guest. And I always remember first being like, man, I'm happy I'm not before. I'm happy I'm not right after him. Like, can you imagine these CEOs being like, oh, you have like this clown after Bezos. Like, everyone would go to the bathroom. Like, nobody. Like, no. So I'm like, at least I'm before. I'll probably get a lot of people sticking around because, like, I gotta give him a good seat for Bezos. And it's like a small venue. So I was actually like, whoa. Like, this is. That's cool. And I remember, like I told you, as I was like, taking pictures of the agenda, sending a picture to my parents, you know, like, yeah, you know, like, you know, I bet you. I bet you Jeff is sending this picture to his, you know, family as well. Like, you know, can't wait to hear what Revy has to say, you know. And so I'm like, okay. So I go and I'm like, I go and like, I did. I did a good job, you know, because I was like, I gotta perform. Like, I didn't know even where he was. But like, look, Chad Bezos is like a business titan, right? And, like, even if you're competing against him in one part of this business, like, I mean, Amazon's an amazing company, right? Like, you know, a trillion dollar company. I think it's like their. Their system is like the modern day railroad, like, what they built. Like, it's a really remarkable thing, you know, I don't think they're as good at groceries as, you know, we are, but they were really amazing. So anyway, I go and I give my talk and I'm kind of like going to go into like the little. I. What I actually thought was gonna happen is they have this little, like, room in the back for, like the speakers. And I was kinda like, oh, man. I'm like, you know, like, give Bezos a little fist bump as we go by, you know, like that kind of thing. And then the founder of the firm comes up to me as I'm walking off, and he's like, hey, man, Jeff and his team are not comfortable with you staying here for his talk. What? I mean, it's so absurd. You're like, what are you talking about? There's no way. And I was just kind of like, I remember processing, like, Izzy, it's too absurd to even be A joke, you.

Know, like, AWS is already rolling at this point. This company, Amazon's already valued for sure.

I mean, I bet you. I mean, this is 2017, 2018. Like, I mean, I don't know, Amazon's probably worth like hundreds of billions of dollars, you know. And so I just kind of looked at him like, very puzzled. He's like, no, I'm really sorry. I'm like. So he basically like, you have to leave. Like, you have to get. You like, remember, like, I had to like leave the premises. I, I mean, you, you know, like, it's not like I just have to like leave the room. I like go. I'm like kicked out. And so I'm like, okay, you know, and then I told you is that I kind of slink out with my shoulders slumped. But then there's this incredible realization and again, I take pride in this looking back of kind of going from bad to good or to hope when I was like, man, the team, I can't wait to tell the team of you guys have shown up on this company's radar. Amazon is famously, we are customer obsessed and competitor aware. We don't care about the competitors, we care about our customers. And I'm like, doesn't seem like that in this case. And I'm sure there was a nuance and there's probably some legal reason that this was different, but I don't care about the details. What I care about there is I'm going to go and tell the team, look what you did. Look what you did. And so we were like, let's go have an all hands. And I remember how proud people were. And we're like, look at this, look what our company is able to do. And it was like one of the craziest things. And of course it's so funny, that moment means nothing to anyone at Amazon, but it meant a lot to us. And it's something that I take with me now of this ridiculous thing of like, okay, we showed up and the team, it was so cool. So cool.

That's awesome.

To sit there with everyone while they got to hear that. And again, one of the coolest things as a leader is when you get to see the team feel earned success. Like, I mean, come on. Nothing better than that.

Yep.

You know, jump forward when. So I mean, when, when do you jump to Sequoia? How does that come about?

Yeah.

And at what point in the stage, like how long you'd been it and Instacart, where were they at at that point when you decided, obviously it's in. And it's in a good space.

My job, you know, I left Instacart basically right before COVID like, late, basically ended the year 2019. And it was in a good spot. It was in a good spot. But, you know, it was interesting. I. I loved my job at Instacart. I loved. I still, like, miss it in many ways, you know, but what happened was we started talking about, like, going public at some point. This is all before COVID and obviously, like, you know, but. So there was discussions about when we were going to go, and I was kind of like, you know, if I am part of this company when it goes public, I need to be willing to commit to the date that we go public as well as for a few years afterwards.

Yeah, right.

Like, you know, and I was kind of like, man, I'm like, signing up for another four or five years. Like, if we go public in two years and I stay for two or three, like, that's a long thing. And, like, I wasn't sure if I would want to do it for another four or five. I knew, I want to do it for another year. Yeah, in two years. I'm like, it's four or five. Felt like I just wasn't sure. It was actually very hard because it was one of those where, like, I wanted to potentially keep going, but it felt like kind of last stop to get off the train, you know, for five years. And I just kept on thinking, like, five years, like, man, like, basically, I mean, that's, like, now, you know, like five years ago. Right? And I was like. I remember thinking about my kids and, like, how old they were going to be, and I was just like, I don't know if I'm ready to, like, commit. It was probably 55, 45, you know, to, like, leave. So it wasn't at all, like, 90, 10, 100, 0, any of that. But I don't know, at some point, it's greater than 50. Like, you gotta. You gotta go. So I told Instagram I was, like, gonna leave, and they actually put me in touch with Moritz, with Sequoia, as, like, to try and convince me to stay, you know, because, like, whatever. Like, he's a board member, and so I talked to him for, like, an hour and a half, and I just kind of like, look, I made up my mind at the end. And then effectively, what happened after that was some version of like, okay, well, if you've made up your mind, you know, then why don't you consider coming here? And so I joked That I either had the longest interview process in history with Sequoia or the shortest interview because I'd, like, known them for four or five years. But then the interview process to actually come and work there was just a few days. And so I went there and I, like, left Instacart on a Friday and joined Sequoia on a Monday. And that is a story of its own. But that I. So I got there five years ago and like, it was. It's been amazing now, but, like, pretty. Pretty tough at certain points, too.

Well, you know, we've talked about this before. Just going through the same thing that you had to go through.

Yeah.

At Duke.

Totally. Right, Totally.

And humbling yourself.

Yes.

And asking the questions. And the same thing that went @. @ McKenzie.

Yes.

And at KKR.

Yes.

You know, hey, I'm this dude. No, I'm not. This dude.

No, I'm not.

You're doing a totally different job.

I need to be sat down and reassess where I am. Right.

For sure. I mean, like, I. So I went and there was. There was an example, in a good way, of somebody who'd come as a former operator and, like, done a great job, which is Carl Eschenbach, who, you know, you know, CEO of Workday. Carl's truly, like one of the all time great people. Truly, like, just as good as it gets. And so I fancied myself, like, wrongly as, like, okay, I'll come in and be able to do what Carl did. I will have operated at a high level and I will come in and effectively like, like be able to, you know, walk into a role that I can be productive. But, like, one, it was egotistical to put myself in the same category as Carl. Carl had operated for 30 years. He's probably the best go to market exec in the Valley. Right. And I mean, I think he is. And like, he's like the CEO candidate for like every big company. Like, he was a better, better operating career than I had and more relevant to the companies because I was like, general manager, you know what I'm saying? And he's like, I know exactly how to, like, turn your salesforce into like a winning team and how to basically sell your product. I mean, like, how incredible is that? So the first thing was just like, being wrong on, like the comp, you know, like who. Who you are trying to be, like, so, you know, I'm trying to do it.

Know your game.

I'm trying to be an imitation of Carl.

Yeah.

And I'm not as good as Carl. In his stuff, right? And then so I walked in again. Ego. You know, I was. I started at 38, so. 38 years old. You know, I have three kids. The kids are. I'm like, you know, their dad. I just come from a place. Like, when you work at a company, your schedule is like an executive schedule is like, presidential meetings don't start until you get there, your calendar's full. All of a sudden, my calendar is dead empty, you know? And I'm trying to act like I'm senior and nobody at Sequoia cares what I have to say. And I mean that with, like, affection. But, like, you're kind of, like, ready for people to be, like, what do you think? You know, I'm like, nobody's asking, and they shouldn't have been because, like, what did I know about, like, whether or not we should invest in these companies, whatever. But, like, you know, and then my. My. The group of people that are there. There's people that are 10 years younger than me who are much better at the job, more senior, like, all this stuff, and it's just, like, so, like, oh, man. And again, Nick, I wish I could tell you, like, oh, I. I just knew it right away. And I learned my lesson from four. I actually really admire some of the stuff you talk about, Alex, in the past of, like, I. I learned that I was not going to do that again. Like, I just kind of did the same thing again where, like, I pretended like it wasn't not going well. Like, all, you know, same as ever, right? And finally this time, I didn't. It was like a combination of myself and, you know, kind of being sat down, but, like, the. Hey, like, you. You have a lot to contribute, but, like, you know, the way you're doing it is not gonna work.

Yeah.

And again, same thing of, like, it's hard, man. You know, like, almost 40 years old and, like, kind of hearing that, like, this thing, you'd gone. You'd left this. I'd left this great job. I'd left on my own volition, this amazing job, you know? And it was just very hard to kind of feel like you sucked and to feel like you weren't contributing. And, like, again, like, not contributing is a really painful thing if you're, like, on a team, you know? And, like, it was just very difficult. And. But the same thing had to happen of, like, okay, like, you have to go learn how to, like, write a good memoir. You have to go learn how to do due diligence. You have to go learn in a different way than what I'd done at kkr, right? You have to learn how to do all these things. And I give a lot of credit to a few people who, like, helped. But, like, Pat Grady, like, my partner, he, like, he's done this for 17 years or so, you know, And Alec, you know Pat, but he's like, he was just willing to sit and teach, you know, but all he wanted was for me to be willing to learn. You know what I'm saying? But then he was willing to do all this so I could sit with him. Hey, you wrote this in this memo. What did it mean? And it was a big change in our relationship when I would be like, hey, I read you one of your old memos. This is what it said. Like, what? You know, why did you do it this way? And he could tell that I, like, all of a sudden was like, you know, in the film room, right? I was, like, actually willing to put in some time. Andrew Reed, another partner of mine, he's a gifted investor. Amazing dude. His wife and I had worked together at Instacart, and so I had known him through that. But I think, again, like, making sure that he knew how much I looked up to him as an investor. Even though he's younger than me, Andrew was probably eight years younger than I. But to communicate to him, hey, look, like, you are awesome at this. Like, can you teach me? And I think that was helpful. Carl was so cool. And again, like, on the people side, Carl, at one point, when he saw that was, like, down, you know, he came up to me and he was like, two things. Like, one, like, I know I look like it's always been good. It hasn't been here. Like, it's been hard for me. What are you laughing about?

I can just picture Ravi walking around the office, the square office. Was it like your acting commercial? Was it that Ravi, for everybody that doesn't know, apparently Shane. Shane on our group tech shot us. That your commercial? What's the peak?

Peak, peak, peak.

And it's a sick commercial. Like, it's got, like, toughest shades ever. Like, I mean, graphics and computer. It's like, it's done. Yeah, you are. It's like you missed it. Yeah, it's. It's like he's playing basketball. It's got all this, like, are you on a green screen? It's got, like, cool. It's done really well. It's sweet. And so somehow then Ravi shoots us this. Is that like, it's in an infomercial.

Or it's like, it's not an infomercial. I don't know what it is. A public service announcement. Sorry for trying to save the country and unite us.

Kind of like, check out my commercial, fellas. Like, I forget what the message was. So we watching it and it goes back to when you're at Duke.

Duke. Yeah.

You were hanging on the couch at McDonald's and they asked you to. They asked you to come film this.

Yeah.

I don't know what the public service announcement is, but Ravi pops up. There's all these other Dukes students, apparently, that are on there. And Ravi jumps up and he's like, just morose.

Yes.

He's so serious. He's such. I know he's such a positive person, but, like, he's so kind of in this commercial. I don't know, maybe that's kind of the stage of life you were at at that point. But that's how I'm picturing anyway.

That's how maybe, maybe, maybe we can.

Put that commercial out.

That'd be great. Yeah. So we'll put a.

Anyway, that's how I click in the bio. Sorry to interject. That's how I picture you walking around the Sequoia office.

About that story is your description of what I sent in the group text of like, yeah, check out my commercial.

Yeah, I got a commercial too, guys.

Yeah, yeah, no, hey, this is the exact opposite of Shane's thing, but because I trust you guys, I'm going to let you see this thing. And instead, now, you know, just put it on blast.

Thanks.

Sure. Yeah. Thank you. Anyway, Carl, you know, great guy. Unlike our friend Alex Smith here with the. With the tramp stamp, you know, that was not gotten enough discussion. He basically was like, look, I know it's been hard for me at certain points. I know it looks like it's not like, it's been nasty hard for me. And then he did this thing, he was so cool. He's like, look, man, as long as I'm here, you're here. And like, he just like, you talk about social acceptance, uncertainty, and Carl, I don't even know if he, like, had the ability to say that. You know what I'm saying? Like, I don't know if he's like the only decision maker. Yeah. But it was so freeing of like, dude, I got you, you know, and like, we want you, you know, and like, go do the thing. Like, go learn it, go through it. But, like, as long as I'm here, you're here. And like, man, that's empowering. So empowering. You know, of just like, I believe in you.

Yeah.

You know, he wasn't, like, leaving it out into the open. He was, like, saying he was assuming I would work hard. You know what I'm saying? He, like, believed in that. Yeah. And like, man, that did such a big thing because all of a sudden you weren't, like, afraid to make a mistake. You weren't afraid to do all these things. You're kind of like, okay, like, somebody's like, you know, I got somebody who's got his hand on my shoulder. And, like, Carl is truly, like I said, one of the greats. But, like, that moment, like, him being a leader, even when he, like, didn't necessarily have the seat to be a leader, like, yeah, come on. You know, and, yeah, that was like a. Yeah, I'm still learning it. I mean, the job is hard, but, like, that was a helpful foundation building thing where, like, honestly, it made me better because at the time, it was even hard to tell an entrepreneur that you wanted to work with, that you wanted to work with them, because you're afraid you're not going to be around, whether on your own decision or somebody else's. You know what I'm saying? So it's even hard to, like, do the job well because you're not as confident on, like, whether you're gonna like it or be around it or any of that and whether they're gonna want you to be a part of it. So it's like, so limiting. It's like the opposite of play free. And then that kind of allowed me to go back to trying to be myself and playing more free.

Well, your story is. It's amazing. It's amazing. And what, you know, what I take away from it is that you see good looking, successful guy who has it all. Beautiful family, beautiful wife, and you were a disaster.

And then you. Then you meet his brother, Ravi. Yes.

You know, like, there are multiple times in your journey when you were the guy on the couch and you had to be sat down. And it's awesome. Yeah, it's so awesome. You know, I mean, how many. How many people think that, you know, we see this in sports all the time. That the perception of hall of Fame athletes and hall of fame investors and CEOs, that they're just born that way. And it's like the furthest thing from the truth.

You know what's crazy to me in your story, and you're very nonchalant about this. Like, listen, I got traded twice, right? I still was playing quarterback. Like, it was the same Job, right? You changed occupations multiple times.

Times.

And you talked about, like, that's. That's, like, that's scary.

Yeah.

Right? And you, like, very. You kind of, like, you know, that just happened. Like, you didn't go move to another CFO job. You didn't go move to another private equity firm, right? Like, you're like, no, I'm gonna go do something completely different. And I think that takes a ton of courage. And, like, I think that curiosity, right? Like, I. In that. And certainly, you know, obviously, that you talk about, like, the doubt and, you know, obviously having to press reset, but not a lot of people want to go do that.

Right?

And again, I think the. Certainly not many people that have walked that line, right, that think about the things you. I mean, like, how many people have operated a company that's IPO'd, right? That's such a.

Such a rare thing.

And obviously, Sequoia in itself carries, you know, obviously, so much weight in kkr. But that's. It's crazy to think about, I think, like, just to change occupations.

What do you. What do you think?

What have you.

What have you learned?

Well, one thing I would tell you guys, and I. I, like. I felt myself, like, being, like, very. It meant a lot to me to hear you guys talk about it because I was very embarrassed about, like, us doing this, as you guys know. Like, I. I'm still kind of, like, it's, like, strange to do it. You know what I'm saying? But I think the genuine curiosity from your friends that, like, want to get to know you and want to, like, understand things and then see things like, you know, Alex, that is something I'm proud of. Of, like, moving around, but it's not. I'm never gonna say that.

Yeah.

So for you to say it is something that, like, that means a lot to me, you know, like. Like to notice it, because it is something that you feel, like, seen by people that you care about. Same thing for you, Shane. Of, like. Yeah. Like, there's, like, bumps and ups and downs. Like, I. I hope that my kids know that, you know, like, all the time of, like, that's just part of it. But I think that, like, what I feel, honestly, man, throughout this is. I feel, like, extreme when I hear it, because I haven't talked about it like this. You talk about being sat down. Like, that's just people who love you, who are, like, doing. That's, like, you should be very grateful. I, like, there's all these people at different moments who have, like, taken an interest and Loved me enough to tell me the truth, you know? And I'm like, man, like, how cool is that? Like, that's, like, real. That's, like, such good luck. And then the other thing is, it makes me wonder, like, what are the other things that are gonna go wrong and, you know, and then come out of. But one of the things I think we all like about each other and I, like, admire about you guys is this, like, resilience. And I hope. I hope Avni the other day said that she thought all of us were resilient people. And, like, that, like, that's the big thing I hope that comes out from this is like, we can all do that and then impart that in our kids and the people that we love. You know?

I'm still just like, the guy that was sitting on the McDonald's couch. Okay. Ten years. Ten years at the, like, biggest private equity firm in the planet.

Yep.

He's like, I'm gonna try my hand at startup. First startup he takes public. Like, already. You're already in a billion. Yeah. Like, you're already in a. There's like, I mean, again, how many companies actually make that? And boom. And then does that, and it's like, well, no, now I'm gonna jump to, like, the gold standard of venture capital.

Yeah.

And. And do this thing. Just super cool. Are there any, like, Glue Guys?

I put Glue Guys there.

Yeah.

You know, starting.

Not bad for the couch surfer.

For those who don't know, Ravi was the. The inspiration behind Glue Guys. After much pestering, I guess, persistence. Better word. So let's add. Let's add that to the. The resume.

Well, as you guys know, like, that now we get to add co founders and co hosts of Glue Guys podcast. Right. Big deal.

Yep.

But, dude, the same thing. If we. Especially as guys, you have to make up an excuse to spend time together. When would we have done this if we didn't have this? There's no chance. Would you ever, like, be like, hey, can you please, like, start at the beginning and tell me your story? Like, are you kidding? But, like, I can't wait for yours. I loved hearing yours. And so to me, it's, like, successful on its own just because, like, we sit and we do this and, like, I. I didn't want to do this, but I'm happy that you guys have now heard it, you know? Like, it makes me feel good that you guys cared and were so interested and so curious, like. Yeah. So. But, yeah, Glue Guys, I think, is the peak of any of the accomplishments. Hopefully any of us have had.

Yep. And we know we can sit them down. Do.

Damn right.

Yeah. Yeah, that feels right. Thanks for tuning in to Glue Guys.

We're on social media at Glue Guys Underscore Podcast, and we'll be back next week.