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Scott Holloway - The Team = The Company · Boardroom Blitz

• JBMIX_0118: Gary Cooper, it's Friday. I don't know what day it is or what number it is, but it's Friday, which means it's time for little blitz in the boardroom here. Jeremie Bacon vid: Gary Cooper, it's Friday. I don't know what day it is or what number it is, but it's Friday, which means it's time for little blitz in the boardroom here. Garry Cooper vid: Little blitz GARYMIX_0117: Well blitz Garry Cooper vid: time. Absolutely. How are you doing t this spray Jeremy? GARYMIX_0117: time. Absolutely. How are you doing t this Friday Jeremy? Jeremie Bacon vid: Great. I just had a very fulfilling lunch. It was probably too filling, but it was really, really tasty. And I had s we had some fabulous conversation over that lunch. as we always do in Chicago. It's pretty amazing. JBMIX_0118: Great. I just had a very fulfilling lunch. It was probably too filling, but it was really, really tasty. And I had s we had some fabulous conversation over that lunch, as we always do in Chicago. It's pretty amazing. GARYMIX_0117: Mm-hmm. Garry Cooper vid: Mm-hmm. Mm-hmm. Well, I also had a great lunch and I had a great conversation. and what a what a week. What a what a week in technology we're experiencing people. I don't know when people will see this, but my lord, they are cars flying. GARYMIX_0117: Mm-hmm. Well, I also had a great lunch and I had a great conversation. and what a what a week. What a what a week in technology we're experiencing people. I don't know when people will see this, but my lord, they are cars flying. Jeremie Bacon vid: Yeah, all kinds of fun stunts coming out of the JBMIX_0118: Yeah, all kinds of fun stunts coming out of the out of the technology this week, which is super cool. I'm still waiting for my Jetsons thing. I'm I'm convinced that by the time my great great grandchildren, assuming that humans don't become robots, I'm convinced that by the time my great great grandchildren are able to drive, they will be able to drive the Jetsons briefcase car. Jeremie Bacon vid: out of the technology this week, which is super cool. I'm still waiting for my Jetsons thing. I'm I'm convinced that by the time my great great grandchildren, assuming that humans don't become robots, I'm convinced that by the time my great-great grandchildren are able to drive, they will be able to drive the Jetsons briefcase car. GARYMIX_0117: Absolutely. Yeah, absolutely. Garry Cooper vid: Absolutely. Yeah, absolutely. Mm mm. ha has has the market already priced in that we're gonna have that? is it is there are people already like, we're long, you know are there any surprises left? GARYMIX_0117: Mm. Mm. I mean ha has has the market already priced in that we're gonna have that? You know, is it is there are people already like, we're long, you know? Are there any surprises left? Jeremie Bacon vid: That'll happen. That'll happen. Some some version of it's happening. JBMIX_0118: That'll happen. That'll happen. Some some version of it's happening. Jeremie Bacon vid: I I I don't think so. I don't think so. I because I don't I don't think it's possible. JBMIX_0118: I I I don't think so. I don't think so. I 'cause I don't I don't think it's possible. Garry Cooper vid: That that's JBMIX_0118: I imagine the physics of that alone, right? Like unless we figure out a way to make human beings weigh about like ninety seven percent less than we do, something tells me something tells me we're not gonna make a foldable car anytime soon. But maybe maybe Jeremie Bacon vid: I'm imagine the physics of that alone, right? Like unless we figure out a way to make human beings weigh about like ninety seven percent less than we do, something tells me, something tells me we're not gonna make a foldable car anytime soon. But maybe maybe GARYMIX_0117: that's Jeremie Bacon vid: we will. I don't know. Yeah. JBMIX_0118: we will. I don't know. Yeah. GARYMIX_0117: Well, Garry Cooper vid: Well, GARYMIX_0117: you know, I I am I am not shocked by the next what's on the horizon for the next ten to fifteen years in science and technology. I I I think it's there's so many great things and and really this weekend reading and thinking and doing a little work, I am amazed by like what's on the horizon for the next twenty or twenty years of of technology. Yeah. Garry Cooper vid: you know, I I am I am not shocked by the next what's on the horizon for the next ten to fifteen years in science and technology. I I I think it's there's so many great things and and really this week in reading and thinking and doing a little work, I am amazed by like what's on the horizon for the next twenty or twenty years of of technology. Yeah. JBMIX_0118: A hundred percent. Me Jeremie Bacon vid: 100%. Me too. Well, sometimes, obviously we we have our our other side hustle, our main hustle together. And so spent a lot of time reading about science and science fiction and science fact and and all the great things that are coming. And actually last weekend I went down and down the rabbit hole little bit and I started reading through a bunch of old, you can find them online. Like you go and look at like newspaper articles from the turn of the 20th century, so 1900, early 1900s. JBMIX_0118: too. Well, sometimes, obviously we we have our our other side hustle, our main hustle together. And so spent a lot of time reading about science and science fiction and science fact and and all the great things that are coming. And actually last weekend I went down and down the rabbit hole a little bit and I started reading through a bunch of old you can find them online. Like you go and look at like newspaper articles from the turn of the twentieth century, so nineteen hundred early nineteen hundreds. Garry Cooper vid: Mm-hmm. GARYMIX_0117: Mm-hmm. Garry Cooper vid: Mm. GARYMIX_0117: Mm. Jeremie Bacon vid: And start looking at the technological predictions and what what actually came true and what didn't come true. And what's interesting is a lot of times the things that people think were going to be impossible are the things that actually happened. And the things that people were like, of course this is gonna happen, or the things that never did, right? and so I can't always help but wonder, like, okay, of the things that we're all thinking about today, like, you know, everything from digitized human beings to like eternal life as robots or matrix or JBMIX_0118: And start looking at the technological predictions and what what actually came true and what didn't come true. And you what's interesting is a lot of times the things that people think were going to be impossible are the things that actually happened. And the things that people were like, of course this is gonna happen, or the things that never did, right? and so I can't always help but wonder, like, okay, of the things that we're all thinking about today, like, you know, everything from digitized human beings to like eternal life as robots or matrix or Garry Cooper vid: Right. GARYMIX_0117: Right. Garry Cooper vid: Yeah. GARYMIX_0117: Okay. Jeremie Bacon vid: utopian societies where everyone has all the money, all the things that they possibly need and the robots just serve us and all that stuff. who the heck knows what's actually gonna happen? I'm just excited to be thinking about it, reading about it and trying to be part of it. JBMIX_0118: utopian societies where everyone has all the money, all the things that they possibly need and the robots just serve us and all that stuff. who the heck knows what's actually gonna happen? I'm just excited to be thinking about it, reading about it and trying to be part of it. GARYMIX_0117: Yeah. Garry Cooper vid: Yeah. GARYMIX_0117: Yeah. Totally. Garry Cooper vid: yeah. there there are maybe one of the last things I'll say is, a couple of weeks ago there was this big announcement with Tempest and Moderna and Merck about their success using kind of mRNA and GARYMIX_0117: there there are maybe one of the last things I'll say is, a couple of weeks ago there was this big announcement with Tempest and Moderna Merck about their success using kind of mRNA and Jeremie Bacon vid: Yeah. GARYMIX_0117: AI to around melanoma. And, you know, so there's a possibility of robots, there's a possibility of digital brains, but this is a possibility of solving indications of diseases that people thought would take us hundreds of years to figure out or so complicated. Garry Cooper vid: AI to around melanoma. And, you know, so there's a possibility of robots, there's a possibility of digital brains, but this is a possibility of solving indications of diseases that people thought would take us hundreds of years to figure out or so complicated. GARYMIX_0117: Steam like Garry Cooper vid: seem like we're just close enough to make progress in a lot of really debilitating disorders. And for me as a neuroscientist, it's just a really exciting time. GARYMIX_0117: we're just close enough to make progress in a lot of really debilitating disorders. And for me as a neuroscientist, it's it's a really exciting time. JBMIX_0118: Totally. Exact well, and then you look at the programmable biology, right? And things that are happening there with being able to reprogram genes in real time to i to fix gene expression, to s to solve h aging and health issues, fix prevent cancers and I it's crazy. It's gonna be really amazing. Amazing. Well what's fun is today our guest is not going to talk about any of those things. But he may, he may, he may. But I guess it's actually maybe we should push him on it and see what he thinks about the future these things. But yeah, exactly. Jeremie Bacon vid: Exact well, and then you look at the programmable biology, right? And things that are happening there with being able to reprogram genes in real time to it to fix gene expression, to s to solve h aging and health issues, fix prevent cancers. And I it's crazy. It's gonna be really amazing. Amazing. Well what's fun is today our guest is not going to talk about any of those things. But he may, he may, he may. But I guess it's actually maybe we should push him on it and see what he thinks about the future of these things. But yeah, exactly. Garry Cooper vid: Amazing. Incredible. Incredible. GARYMIX_0117: Amazing. Incredible. Incredible. Garry Cooper vid: Mm-hmm. GARYMIX_0117: Mm-hmm. he may, he's brilliant. Yes. Scott, what do you think about digital braids? Garry Cooper vid: he may, he's brilliant. Yes. Scott, what do you think about digital braids? JBMIX_0118: But our our our guest today is Scott Holloway, who is a super cool dude. For those of you who do not know him, you're in for a retreat. so Scott's a general partner at Starting Line. But before that, Scott was also Instacart's 10th employee, and he helped to launch its first office outside Silicon Valley. And after that, he expanded that into dozens of markets and had a fabulous trip doing so. After his Instacart days, he managed Flexport's Chicago and Dallas offices, with where he managed several hundred employees. Jeremie Bacon vid: But our our our guest today is Scott Holloway, who is a super cool dude. For those of you who do not know him, you're in for a retreat. so Scott's a general partner at Starting Line. But before that, Scott was also Instacart's 10th employee, and he helped to launch its first office outside Silicon Valley. And after that, he expanded that into dozens of markets and had a fabulous trip doing so. After his Instacart days, he managed Flexport's Chicago and Dallas offices, with where he managed several hundred employees. JBMIX_0118: before ultimately moving into venture investing. he's also civically involved in Chicago and in the tech ecosystem wherever he can be. and it's just a fabulously cool guy. So we're super sta stoked to have you here with us today, Scott, and we appreciate you making time. Jeremie Bacon vid: before ultimately moving into venture investing. he's also civically involved in Chicago and in the tech ecosystem wherever he can be. and it's just a fabulously cool guy. So we're super sta stoked to have you here with us today, Scott. And we appreciate you making time. Garry Cooper vid: It's good. GARYMIX_0117: It's good. SCOTTMIX_0120: Hey guys, happy to be here. I I also enjoy taking Gary's money in poker every now and then. Scott Holloway vid1.2: Hey guys, happy to be here. I I also enjoy taking Gary's money and poker every now and then. Jeremie Bacon vid: Ha ha. JBMIX_0118: Ha ha. Jeremie Bacon vid: This is true. I've got photos of this, I think, somewhere. Yeah. Scott lording it over, Gary. Yeah. Gary, seven two's not the hand you want to go all in with. I'm just gonna just gonna say. JBMIX_0118: This is true. I've got photos of this, I think, somewhere. Yeah. Scott lording it over, Gary. Yeah. Gary seven two's not the hand you want to go all in with. I'm just gonna just gonna say. Garry Cooper vid: Bad B Bad B. The deck was sacked against me. You know, I don't GARYMIX_0117: Bad B Bad B. The deck was stacked against me. And you know, and that SCOTTMIX_0120: That's right. Scott Holloway vid1.2: That's right. GARYMIX_0117: was one Scott Holloway vid1.2: That's right. SCOTTMIX_0120: That's right. Garry Cooper vid: play seven deuce, but it turns out sometimes kings get cracked. And Scott Holloway vid1.2: Yeah. SCOTTMIX_0120: Yeah. Garry Cooper vid: you know, and that was one time. GARYMIX_0117: time. SCOTTMIX_0120: Yeah. JBMIX_0118: That was one time. Jeremie Bacon vid: That was one time. Scott Holloway vid1.2: We'll run it. JBMIX_0118: I'm sure that's the only time you ever won a hand against Get Ray, right, Scott? Exactly. We're gonna have to have the boardroom blit actually what we should do one of these days is get all our boardroom blitz to get guests together and have a poker tournament or something like that. Like a fun, friendly one where yeah, we play for for pride. Yes for great. Sorry, but good times. Good times. All right, Scott, where should we start? Jeremie Bacon vid: I'm sure that's the only time you ever win a hand against Get Ray, right, Scott? Exactly. We're gonna have to have the boardroom blit actually what we should do one of these days we get all our boardroom blitz to get guests together and have a poker tournament or something like that. Like a fun, friendly one where yeah, we play for for pride. Yeah, super great. Sorry, but yeah, exactly. good times, good times. All right, Scott, where should we start? SCOTTMIX_0120: That's right. That's right. Scott Holloway vid1.2: That's right. That's right. Garry Cooper vid: We should do that. We should do that. GARYMIX_0117: We should do that. We should do that. SCOTTMIX_0120: That sounds great. Scott Holloway vid1.2: Sounds great. GARYMIX_0117: For pride. Garry Cooper vid: For pride. JBMIX_0118: there are so many directions we could take our conversation first. As with Border Blitz, we're we're we're trying to Jeremie Bacon vid: there are so many directions we could take our conversation first. As with Border Blitz, we're we're we're trying to GARYMIX_0117: Does he know if there was a point? JBMIX_0118: share wisdom and share insights into the leadership experience, the leadership journey and building and helping to run and manage companies. maybe it would make sense to start at Instacart, why don't we? Because that was such an epic journey for the company and for you. I'd love to see, or maybe maybe the right question to begin with from my perspective is what did you see in that company so early that made you believe it could become so big? And like, Jeremie Bacon vid: share wisdom and share insights into the leadership experience, the leadership journey and building and helping to run and manage companies. maybe it would make sense to start at Instacart, why don't we? Because that was such an epic journey for the company and for you. I'd love to see, or maybe maybe the right question to begin with from my perspective is what did you see in that company so early that made you believe it could become so big? And like. GARYMIX_0117: Okay. Garry Cooper vid: Good. See. Jeremie Bacon vid: Second piece of that is what did you totally misjudge walking into it? JBMIX_0118: Second piece of that is what did you totally misjudge walking into it? Scott Holloway vid1.2: man. yeah, so I started my career. you know, I studied finance in school, study my I started my career at Northern Trust, SCOTTMIX_0120: man. yeah. So I started my career. you know, I studied finance in school, study my I started my career at Northern Trust, GARYMIX_0117: Basically. Garry Cooper vid: Yes, we can. Scott Holloway vid1.2: doing a couple of different roles SCOTTMIX_0120: doing a couple of different roles Scott Holloway vid1.2: in finance there, being a portfolio manager, tried to build a couple of companies SCOTTMIX_0120: in finance there, being a portfolio manager. Tried to build a couple of companies Scott Holloway vid1.2: on the side there, like got like a little social wellness app off the ground and nothing was really nothing was really working. And so this was like mid twenty thirteen and I was I want to join something that I think is going to grow incredibly quickly. SCOTTMIX_0120: on the side there, like got like a little social wellness app off the ground and nothing was really nothing was really working. And so this was like mid twenty thirteen. And I was like, I want to join something that I think is going to grow incredibly quickly. Garry Cooper vid: well. GARYMIX_0117: well. SCOTTMIX_0120: And that was my only criteria. I was like, I wanted see hypergrowth so I can eventually try to go build something on my own. And so I spent a while Scott Holloway vid1.2: And that was my only criteria. I was like, I wanted see hyper growth so I can eventually try to go build something on my own. And so I spent a while SCOTTMIX_0120: looking at companies and identified Uber and Instacart. Uber was like 200 people at the time, Instacart was nine, and just finishing up Y Combinator, and then you know, went way down the road talking to both of them and ultimately took the Instacart job. And what attracted me to that to answer you know, your question was Scott Holloway vid1.2: looking at companies and identified Uber and Instacart. Uber was like 200 people at the time, Instacart was nine, and just finishing up Y Combinator, and then you know, went way down the road talking to both of them and ultimately took the Instacart job. And what attracted me to that to answer you know, your question was. SCOTTMIX_0120: one like like startups are kind of a point in time. Scott Holloway vid1.2: One, startups are a point in time also where you can be too early or too late. And Mike Moritz, the chairman of Sequoia, had just led the seed round there. And what I loved about that not only is that Sequoia, but he also led the web van investment, SCOTTMIX_0120: Also, where you can be too early or too late. And Mike Moritz, the chairman of Sequoia, had just led the seed round there. And what I loved about that not only is that Sequoia, but he also led the web van investment, which was one of the most famous flameouts of the first dot-com era. So I was like, he clearly sees something here. And I knew that it was growing like crazy in San Francisco. And there was an opportunity to Scott Holloway vid1.2: which was one of the most famous flameouts of the first dot-com era. So I was like, he clearly sees something here. And I knew that it was growing like crazy in San Francisco. And there was an opportunity to basically bring it to a market which is actually a real test, like SCOTTMIX_0120: basically bring it to a market which is actually a real test. Like When those businesses work in San Francisco, I I don't think that that's real. It's that's an assisted living community for the young out there. everything gets delivered. And so ultimately like that was that was a lot of my criteria. And then actually how I got the the job, which we can talk about later, is is also a very interesting story. Yeah. Scott Holloway vid1.2: When those businesses work in San Francisco, I I don't think that that's real. It's that's an assisted living community for the young out there. everything gets delivered. And so ultimately like that was that was a lot of my criteria. And then actually how I got the the job, which we can talk about later, is is also a very interesting story. Yeah. Garry Cooper vid: Mm-hmm. GARYMIX_0117: Mm-hmm. Mm-hmm. JBMIX_0118: Sure. Yeah, yeah. Jeremie Bacon vid: Sure. Yeah, yeah. Garry Cooper vid: Mm-hmm. What did you do initially? Or what didn't you do maybe as as employee number ten? GARYMIX_0117: What did you do initially? Or what didn't you do maybe as as employee number ten? Scott Holloway vid1.2: Dude, I'm SCOTTMIX_0120: Dude, I'm we had a office above a Chinese restaurant at 1325 South Wabash. And we were onboarding shoppers 200 a day. We would set we would basically I would post Craigslist ads. I said like during like this this like boom of like Uber Lyft, DoorDash, Instacart, like the biggest winner was Craigslist because I was personally spending 20 grand a month on ads just in like our market. Scott Holloway vid1.2: we had a office above a Chinese restaurant at 1325 South Wabash. And we were onboarding shoppers 200 a day. We would set we would basically I would post Craigslist ads. I said like during like this this boom of like Uber Lyft, DoorDash, Instacart, the biggest winner was Craigslist because I was personally spending 20 grand a month on ads just in like our market. Garry Cooper vid: huh. GARYMIX_0117: huh. Garry Cooper vid: Mm-hmm. Jeremie Bacon vid: Hind Craigslist, yeah. JBMIX_0118: Hindraislist, yeah. Scott Holloway vid1.2: and we would bring these folks in, five at a time. We'd give them a shopping list. We'd download the app. they'd go down to whole. Yeah. They'd go down to Whole Foods. they would shop the order, they'd send us pictures, and then if they did a good job, we'd bring them on, they'd go out shopping later that night. SCOTTMIX_0120: and we would bring these folks in, five at a time. We'd give them a shopping list, we'd download the app. they'd go down to home. Yeah, they'd go down to Whole Foods, they would shop the order, they'd send us pictures, and then if they did a good job, we'd bring them on, they'd go out shopping later that night. Garry Cooper vid: interesting. GARYMIX_0117: interesting. Garry Cooper vid: Wow, incredible. GARYMIX_0117: Wow. Incredible. Jeremie Bacon vid: Really cool. Super fun. So then how many how JBMIX_0118: Really cool. Super fun. So then how many how many shoppers are you adding a week then? And how many of them flamed out? Because I'm super curious. I have to imagine some people are like, this could be interesting way to make some money. And then they did once, I really don't do it. How how did you go through the recruiting process Jeremie Bacon vid: many shoppers were you adding a week then? And how many of them flamed out? Because I'm super curious. I have to imagine some people are like, this could be an interesting way to make some money. And then they did it once, Well, I really don't do this. how how did you go through the recruiting process SCOTTMIX_0120: Yeah, we were adding as many as we we possibly could. hundreds a week initially, but that business was supply constrained for five years. Like yeah, it grew every single week, holiday, like no matter what weather. And so we were trying to hire as many shoppers as we could, hundreds, and then eventually when we did it all all touchless, like you know, tens of thousands a week. Scott Holloway vid1.2: Yeah, we were adding as many as we we possibly could. hundreds a week initially, but that business was supply constrained for five years. Like it grew every single week, holiday, like no matter what weather. And so we were trying to hire as many shoppers as we could, hundreds, and then eventually when we did it all all touchless, like you know, tens of thousands a week. JBMIX_0118: beyond just Jeremie Bacon vid: beyond just Garry Cooper vid: Incredible. GARYMIX_0117: Incredible. Jeremie Bacon vid: I'm sure. Well, so what what JBMIX_0118: Sure. Well so what what what did Linstecart and what did you learn about scaling that was fundamentally counterintuitive during that time? Because I have to imagine, as all things, nothing goes quite to plan and we don't really realize Jeremie Bacon vid: what did Lin Stecart and what did you learn about scaling that was fundamentally counterintuitive during that time? Because I have to imagine, as all things, nothing goes quite to plan and we don't really realize JBMIX_0118: it's impossible to forecast exactly how things were going to go. was there something that turned out to be very coun counterintuitive about that rapid growth? Jeremie Bacon vid: it's impossible to forecast exactly how things were going to go. was there something that turned out to be very coun counterintuitive about that rapid growth? Scott Holloway vid1.2: I think the hardest part about scaling that business or any marketplace like that is actually perfectly balancing supply and demand. And you're never going to get it perfect. So, for example, when we launch new markets, you have to hire, 200 shoppers ahead of any demand that you know exists, and you have to pay those folks. And so you want the perfect amount of supply such that when demand hits the site, you can deliver an order in one hour, but not so much supply such that you're paying for latent labor. SCOTTMIX_0120: I think the hardest part about scaling that business or any marketplace like that is actually perfectly balancing supply and demand and you're never going to get it perfect. So, for example, when we launch new markets, you have to hire, 200 shoppers ahead of any demand that you know exists, and you have to pay those folks. And so you want the perfect amount of supply such that when demand hits the site, you can deliver an order in one hour, but not so much supply such that you're paying for latent labor. Scott Holloway vid1.2: And we it's an impossible problem to solve. It's like a data science problem. SCOTTMIX_0120: And we it's an impossible problem to solve. It's like a data science problem. Jeremie Bacon vid: Mm-hmm. JBMIX_0118: Yeah. Garry Cooper vid: Mm. SCOTTMIX_0120: and like we went through periods of time where, you know, we're burning forty million dollars a month because we're getting that problem wrong. And so it's just trying to figure out what is like Scott Holloway vid1.2: and like we went through periods of time where, you know, we're burning forty million dollars a month because we're getting that problem wrong. And so it's just trying to figure out what is like SCOTTMIX_0120: forecasting demand and ensuring you have like this right amount of like, you know, efficient frontier supply. Scott Holloway vid1.2: forecasting demand and ensuring you have like this right amount of like, you know, efficient frontier supply. Jeremie Bacon vid: Super cool. JBMIX_0118: Super cool. Garry Cooper vid: Hmm. GARYMIX_0117: Mm. So so so you were at Instacart and you were doing this in the in the Chicago, the newly minted Chicago office, and then and then you moved on from from Instacart to Flexport. Can you talk a little bit Garry Cooper vid: So so so you were at Instacart and you were doing this in the in the Chicago, the newly minted Chicago office, and then and then you moved on from from Instacart to Flexport. Can you talk a little bit JBMIX_0118: It's I Scott Holloway vid1.2: Yeah. Yeah. GARYMIX_0117: about what was different, Garry Cooper vid: what was different, GARYMIX_0117: what you were doing there, just to kind of give people kind of a whole Garry Cooper vid: what you were doing there, just to kind of give people kind of a whole big history of your operating what you done in operations? GARYMIX_0117: big history of your operating what you done in operations? Scott Holloway vid1.2: Yeah, I I spent so I spent six years at Instacart, going from SCOTTMIX_0120: Yeah, I spent so I spent six years at Instacart, going from Scott Holloway vid1.2: 50 grand SCOTTMIX_0120: fifty grand Scott Holloway vid1.2: in revenue to like two billion. And so got to see that SCOTTMIX_0120: in revenue to like two billion. And so got to see that through like Scott Holloway vid1.2: through like SCOTTMIX_0120: just an insane trajectory. And then towards the end, I joined the advertising team. And that was like my attempt of like finding the startup within the startup because the money machine was already was already built and it's like what is like the next frontier and now all of Scott Holloway vid1.2: just an insane trajectory. And then towards the end, I joined the advertising team. And that was like my attempt of like finding the startup within the startup because the money machine was already was already built. And it's like, what is like the next frontier? And now all of Garry Cooper vid: Mm-hmm. GARYMIX_0117: Mm-hmm. Scott Holloway vid1.2: the entirety of Instacart's like net income. It's you it's like a billion dollar SCOTTMIX_0120: the entirety of Instacart's like net income. It's you it's like a billion dollar profitable business on ads. And then Scott Holloway vid1.2: profitable business on ads. And then, Jeremie Bacon vid: business right. JBMIX_0118: Right. SCOTTMIX_0120: you know, I had gotten hit up by recruiters throughout that journey all the time, never answered, like never picked up a call. But then Scott Holloway vid1.2: you know, I had gotten hit up by recruiters throughout that journey all the time, never answered, like never picked up a call. But then SCOTTMIX_0120: when Flexport called, I was like, this is so different. Like and I have learned the consumer game. And this is a completely new set of skills. I break new muscles. And from afar, I had always admired Ryan Peterson. Like he is an incredible person, an incredible leader. Scott Holloway vid1.2: when Flexport called, I was like, this is so different. Like, and I have learned the consumer game. And this is a completely new set of skills. I break new muscles. And from afar, I had always admired Ryan Peterson. Like he is an incredible person, an incredible leader. Garry Cooper vid: Thing. Thing. GARYMIX_0117: Right. Right. SCOTTMIX_0120: Has his own reality distortion field. And so I love the idea of being able to step into an office of 150 people Scott Holloway vid1.2: Has his own reality distortion field. And so I love the idea of being able to step into an office of 150 people SCOTTMIX_0120: and do something new, run account management teams, sales teams, edge teams, product Scott Holloway vid1.2: and do something new, run account management teams, sales teams, edge teams, product SCOTTMIX_0120: teams Scott Holloway vid1.2: and lead that office. And then COVID hit and we're running a supply chain business. And it was just the most insane kind of two years. SCOTTMIX_0120: and lead that office. And then COVID hit and we're running a supply chain business. And it was just the most insane kind of two years. JBMIX_0118: I can imagine. So obviously two businesses trying to modernize enormous complicated industries between these two with but Jeremie Bacon vid: I can imagine. So obviously two businesses trying to modernize enormous complicated industries between these two with but JBMIX_0118: other aside from COVID, with the COVID factor being the COVID factor, Jeremie Bacon vid: other aside from COVID, with the COVID factor being the COVID factor, were there other big differences in JBMIX_0118: were there other big differences in Jeremie Bacon vid: how those organizations both approached growth JBMIX_0118: how those organizations both approached growth and Jeremie Bacon vid: and growth metrics and driving for it? JBMIX_0118: growth metrics and driving for it? Scott Holloway vid1.2: Yeah. SCOTTMIX_0120: Yeah. you know, Ryan Scott Holloway vid1.2: you know, Ryan SCOTTMIX_0120: Peterson Scott Holloway vid1.2: Peterson SCOTTMIX_0120: he's a big historian. He basically wanted to build that business Scott Holloway vid1.2: he's a big historian. He basically wanted to build that business SCOTTMIX_0120: kind of based off the military, like into like these self basically sustaining pods where every region was its own basically decision-making authority, own PL, obviously like aligned to one mission and then like see what worked best. It's like, like my colleague Caitlin on the East Coast, Scott Holloway vid1.2: kind of based off the military, like into these self basically sustaining pods where every region was its own basically decision-making authority, own PL, obviously like aligned to one mission and then like see what worked best. It's like, like my colleague Caitlin on the East Coast, SCOTTMIX_0120: is improving margins like this much. what is she doing? And basically have these competing entities Scott Holloway vid1.2: is improving margins like this much. what is she doing? And basically have these competing entities SCOTTMIX_0120: enforces so that we could share best practices, which I Scott Holloway vid1.2: in forces so that we could share best practices, which I SCOTTMIX_0120: thought was really interesting. But then like I got I remember like I started Scott Holloway vid1.2: thought was really interesting. But then I got I remember I started SCOTTMIX_0120: and I got Scott Holloway vid1.2: and I got this like list of all of the these I think we had like 140 people in the office SCOTTMIX_0120: this like list of all of the these I think we had like 140 people in the office and Scott Holloway vid2: And I got this SCOTTMIX_0123: And I got this Scott Holloway vid2: kind of mandate down from you know, Ryan of like, here are the 40 roles that you need to hire. SCOTTMIX_0123: kind of mandate down from you know, Ryan of like, here are the forty roles that you need to hire. Scott Holloway vid2: basically like before the end of the year. SCOTTMIX_0123: basically like before the end of the year. GARYMIX_0122: Okay. SCOTTMIX_0123: And I was like from first principles, I was like, Okay, can we like at least talk through Scott Holloway vid2: And I was like from first principles, I was like, Okay, can we like at least talk through Garry Cooper vid 2: Thank SCOTTMIX_0123: like this stuff? This is like two million dollars of fully loaded. Scott Holloway vid2: like this stuff? This is like two million dollars of fully loaded. SCOTTMIX_0123: addition to my PL. Scott Holloway vid2: addition to my PL. And so that was one big change if you have to hire this many d dozens of folks. SCOTTMIX_0123: And so that was one big change if you have to hire this many d dozens of folks. And then at COVID hits at Flexport, Scott Holloway vid2: And then at COVID hits at Flexport, we have a meeting with Ryan, SCOTTMIX_0123: we have a meeting with Ryan, Scott Holloway vid2: the CEO and the three SCOTTMIX_0123: the CEO and the three GMs. And he says, you guys have to cut, Scott Holloway vid2: And he says, you guys have to cut, SCOTTMIX_0123: X percent of your PL, Scott Holloway vid2: X percent of your PL, SCOTTMIX_0123: immediately. Like this is going to totally change Scott Holloway vid2: immediately. Like this is going to totally change our business. Like we need to cut costs and prepare. SCOTTMIX_0123: our business. Like we need to cut costs and prepare. Scott Holloway vid2: Fast forward a month from that, what happens? SCOTTMIX_0123: Fast forward a month from that, what happens? Scott Holloway vid2: Supply chain goes through the roof. We're doing stimulus checks to all Americans. And Flexport is growing faster than ever, more profitable than ever. We have to hire all these people again. So it was just like whip sawing back and forth priorities and trying to manage, you know, an office and keeping people SCOTTMIX_0123: Supply chain goes through the roof. We're doing stimulus checks to all Americans, and Flexport is growing faster than ever, more profitable than ever. We have to hire all these people again. So it was just whipsawing back and forth priorities and trying to manage, you know, an office and keeping people GARYMIX_0122: No screen was okay. Scott Holloway vid2: engaged and excited with like the uncertainty of where the business is going, like will folks have jobs and ultimately like navigated through it okay. But it was just a very tumultuous time, particularly because of what was going on in the supply chain. SCOTTMIX_0123: engaged and excited with like the uncertainty of where the business is going, like will folks have jobs and ultimately like navigated through it okay. But it was just a very tumultuous time, particularly because of what was going on in the supply chain. GARYMIX_0122: Okay. Jeremie Bacon vid 2: I can imagine. I can imagine. JBMIX_0121: I can imagine. I can imagine. Well, and then if you're growing the team and then shrinking the game and then regrowing the team at that fast of a rate, I'd imagine too. I don't just imagine I know the leadership style that makes you successful at two hundred people or four hundred people is different from the leadership style that makes you successful at twenty people. Jeremie Bacon vid 2: Well, and then if you're growing the team and then shrinking the game and then regrowing the team at that fast of a rate, I'd imagine too. I don't just imagine I know the leadership style that makes you successful at 200 people or 400 people is different from the leadership style that makes you successful at twenty people. Scott Holloway vid2: For sure. JBMIX_0121: were Jeremie Bacon vid 2: were JBMIX_0121: there like lessons that you picked up along that Jeremie Bacon vid 2: there like lessons that you picked up along that Garry Cooper vid 2: Thank JBMIX_0121: trail Jeremie Bacon vid 2: trail JBMIX_0121: that you Jeremie Bacon vid 2: that you JBMIX_0121: would like to share with our audience? Jeremie Bacon vid 2: would like to share with our audience? GARYMIX_0122: Yeah. Scott Holloway vid2: Yeah, I like this is where get hiring. I think I I think hiring is the most SCOTTMIX_0123: Yeah, I like this is where get hiring. I think I I think hiring is the most Garry Cooper vid 2: Thank you. Scott Holloway vid2: critical function of executive leaders. all a company is is a collection of people making decisions. a company is just people. And so being able to leverage yourself by hiring incredible people. And I had incredible directors SCOTTMIX_0123: critical function of executive leaders. all a company is, is a collection of people making decisions. a company is just people. And so being able to leverage yourself by hiring incredible people. And I had incredible directors Garry Cooper vid 2: And so we're going to be using the same. Scott Holloway vid2: at Flexport and incredible VPs SCOTTMIX_0123: at Flexport and incredible VPs that I could rely on. And so I think Scott Holloway vid2: that I could rely on. And so I think GARYMIX_0122: Mm-hmm. SCOTTMIX_0123: throughout Scott Holloway vid2: throughout my leadership journey, like that's probably the biggest learning is the team you build is the company you build. SCOTTMIX_0123: my leadership journey, like that's probably the biggest learning is the team you build is the company you build. Scott Holloway vid2: And so, SCOTTMIX_0123: And so, hiring a 10 out of 10 person is such a multiplier. And I think that was one of the biggest benefits that I got from my time at Instacart. And what I think has actually made me an okay investor to this point is I actually got to see what excellence was. I know what a 10 out of 10 engineer is, I know what a 10 out of 10 CFO is, I know what a 10 out of 10 operator is. Like in and if you see these people, it is different. And so, like when I'm talking to current founders and CEOs now, and I'm in interviews with them and I'm running their. Scott Holloway vid2: hiring a 10 out of 10 person is such a multiplier. And I think that was one of the biggest benefits that I got from my time at Instacart. And what I think has actually made me an okay investor to this point is I actually got to see what excellence was. I know what a 10 out of 10 engineer is, I know what a 10 out of 10 CFO is, I know what a 10 out of 10 operator is. Like in and if you see these people, it is different. And so, like when I'm talking to current founders and CEOs now, and I'm in interviews with them and I'm running their Garry Cooper vid 2: Thank you. SCOTTMIX_0123: be it be a product interviews or I'm grading their case studies. I'm like, this individual just isn't good enough. They wouldn't have gotten past a first screening. And so you have to push and push and push to find the best people Scott Holloway vid2: be it be a product interviews or on grading their case studies, I'm like, this individual just isn't good enough. They wouldn't have gotten past a first screening. And so you have to push and push and push to find the best people GARYMIX_0122: That's kind. Scott Holloway vid2: if you want to build like generational multi-billion dollar companies. SCOTTMIX_0123: if you want to build like generational multi-billion dollar companies. Jeremie Bacon vid 2: I totally agree with that. That's amazing. So Yeah, a hundred percent. Team is team is so important and individual contributors to that team are so important. JBMIX_0121: I totally agree with that. That's amazing. So Yeah, a hundred percent. Team is team is so important and individual contributors to that team are so important. GARYMIX_0122: You're here. Garry Cooper vid 2: You're here. Thank you. GARYMIX_0122: Yeah. JBMIX_0121: to that end, do you when you're thinking about structuring teams, Jeremie Bacon vid 2: to that end, do you, when you're thinking about structuring teams, GARYMIX_0122: Yeah. Jeremie Bacon vid 2: how how do you go about JBMIX_0121: how do you go about putting your teams together, Jeremie Bacon vid 2: putting your teams together, JBMIX_0121: whether it's in your past experience or now as an investor, Jeremie Bacon vid 2: whether it's in your past experience or now as an investor, as it relates to JBMIX_0121: as it relates to pairing opposites to each other and creating teams Jeremie Bacon vid 2: pairing opposites to each other and creating teams JBMIX_0121: that can create and then thrive in Jeremie Bacon vid 2: that can create and then thrive in healthy friction environments. Is that something you actively think about? Is it something that you've JBMIX_0121: healthy friction environments. Is that something you actively think about? Is it something that you've struggled with that you are that's aspirational or something that is just such an no brainer that it's been part of your Jeremie Bacon vid 2: struggled with that you are that's aspirational or something that is just such an no brainer that it's been part of your GARYMIX_0122: Yeah. Jeremie Bacon vid 2: ethos from day one? JBMIX_0121: ethos from day one? Scott Holloway vid2: Yeah, I think you have to be really SCOTTMIX_0123: Yeah, I think you have to be really ruthless about your own Scott Holloway vid2: ruthless about your own deficiencies. I think like early on in your career, like you probably like think you can be good at everything. But then like as you develop your skill sets, you realize that like you have certain superpowers and you have a lot of areas that you're not great at. And so I think SCOTTMIX_0123: deficiencies. I think like early on in your career, like you probably like think you can be good at everything. But then like as you develop your skill sets, you realize that like you have certain superpowers and you have a lot of areas that you're not great at. And so I think I learned that throughout my time, you know, at Flexport, like and then Foxtrot. and was just like, if I want to be the best executive like that I can be, I have to make sure that the folks around me, Scott Holloway vid2: I learned that throughout my time, you know, at Flexport, like and then Foxtrot. and was just like, if I want to be the best executive like that I can be, I have to make sure that the folks around me SCOTTMIX_0123: or like Scott Holloway vid2: or like beneath in in the org chart, are excellent in areas that I am not. And making sure that every single person you hire raises the bar for like the the median performance across the organization. And it's like every new hire, whether it's a finance hire, SCOTTMIX_0123: beneath in in the org chart, are excellent in areas that I am not. And making sure that every single person you hire raises the bar for like the the median performance across the organization. And it's like every new hire, whether it's a finance hire, Scott Holloway vid2: that person should be better at finance than the current person is at operations. And just like that raise the bar every single time. SCOTTMIX_0123: that person should be better at finance than the current person is at operations. And just like that raise the bar every single time. GARYMIX_0122: I have a question there, Scott. especially given your Instacart Garry Cooper vid 2: I have a question there, Scott, especially given your Instacart GARYMIX_0122: history, your flexboard history, even how you just mentioned Fox Trot, those are different cultures, different businesses. Garry Cooper vid 2: history or Flexport history, even how you just mentioned Proxtrot, those are different cultures, different businesses. GARYMIX_0122: You know, and this word around team culture is something at least that I thought a lot about, especially during the pandemic. You know, how are people doing? You talked about the whipsaw of maybe having to, you know, reduce costs and then like Garry Cooper vid 2: this word around team culture is something at least that I thought a lot about, especially during the pandemic. How are people doing? You talked about the whipsaw of maybe having to reduce costs and then GARYMIX_0122: loading costs on because demand had spiked. Garry Cooper vid 2: loading costs on because demand had spiked. How do you think about, if you're talking to a young founder now, or a young founder might be listening, and they're thinking about, GARYMIX_0122: How do you think about if you're talking to a young founder now or a young founder might be listening and they're thinking about, Garry Cooper vid 2: hey, we might have to scale back, or some folks are thinking, hey, we might need to scale up. GARYMIX_0122: we might have to scale back, or some folks are thinking, hey, we might need to scale up. What are some Garry Cooper vid 2: What are some basic things you're thinking about, no matter what's happening, and trying to keep team unity and team culture? GARYMIX_0122: basic things you think about no matter what's happening and trying to keep team unity and team culture? Scott Holloway vid2: Yeah, it's funny. I think if you haven't been inside, these fast-growing companies, culture sounds like this ephemeral, weird thing, but culture is everything. Culture is like, what is the accepted, acceptable standard of work? SCOTTMIX_0123: Yeah, it's funny. I think if you haven't been inside, these fast growing companies, culture sounds like this ephemeral, weird thing, but culture is everything. Culture is like, what is the accepted, acceptable standard of work? Scott Holloway vid2: how how hard do people work? how good is the output of work? how how do people treat each other? SCOTTMIX_0123: how how hard do people work? how good is the output of work? how how do people treat each other? Garry Cooper vid 2: Right. Scott Holloway vid2: and you know, one cool exercise that I got to lead at Instacart with one of my colleagues was this the founder Aporva asked me SCOTTMIX_0123: and you know, one cool exercise that I got to lead at Instacart with one of my colleagues was this the founder Aporva asked me. And one other individual Scott Holloway vid2: one other individual. SCOTTMIX_0123: to write our company values. And that's like a that's a really cool, but a big Scott Holloway vid2: To write our company values. And that's a cr that's a really cool, but a big Garry Cooper vid 2: Mm. GARYMIX_0122: Mm. SCOTTMIX_0123: responsibility. And there's a lot of ways to go about that. And we involve the whole company in it. But one simple heuristic Scott Holloway vid2: responsibility. And there's a lot of ways to go about that. And we involve the whole company in it. But one simple heuristic, SCOTTMIX_0123: for doing that and like how to think about culture Scott Holloway vid2: for doing that, and like how to think about culture SCOTTMIX_0123: is who is the person in the company that you most admire? Scott Holloway vid2: is who is the person in the company that you most admire? and and why. And then I thought about that, and it's this very specific individual SCOTTMIX_0123: and why? And then I thought about that, and it's this very specific individual GARYMIX_0122: Mm. Mm-hmm. Garry Cooper vid 2: Mm. Mm-hmm. SCOTTMIX_0123: at Instacart. And I'm like, what makes this person special? Scott Holloway vid2: at Instacart. And I'm like, what makes this person special? And it was a very simple list of five attributes on why this individual SCOTTMIX_0123: And it was a very simple list of five attributes on why this individual is so remarkable and to this day the most talented and incredible person I've ever worked with. And then you can work backwards from we want to instill the best parts of that throughout the organization. Scott Holloway vid2: is so remarkable and to this day the most talented and incredible person I've ever worked with. And then you can work backwards from we want to instill the best parts of that throughout the organization. GARYMIX_0122: Mm-hmm. I I love that because seeing seeing is believing. Garry Cooper vid 2: Mm hmm. I love that because seeing seeing is believing. JBMIX_0121: We're cool. GARYMIX_0122: And I think, really in any of these kind of cultures, you have to have people who you you might not say to their face, but you look up to maybe not their whole person, but there's something about what they do that's desirable for you to do. Garry Cooper vid 2: And I think, you know, really in any of these kind of cultures, you have to have people who you might not say to their face, but you look up to maybe not their whole person, but there's something about what they do that's desirable for you to do. GARYMIX_0122: And that brings you to work to either fight for the company and fight for that person to be there. Garry Cooper vid 2: And that brings you to work to either fight for the company and fight for that person to be there or just to be like them and to learn, like, how can I be that and kind of reaching out? GARYMIX_0122: or just to be like them and to learn, how can I be that and reaching up. Garry Cooper vid 2: it reflect on that as you start in a mentor, GARYMIX_0122: and reflect on that as you're starting to mentor young founders, young CEOs these days. Do you think that like they are as intentional around Garry Cooper vid 2: young founders, young CEOs these days, do you think that like they are as intentional around GARYMIX_0122: value setting, culture setting, some of the things you talked about and opportunities you've had as you see in the past, or do you think Garry Cooper vid 2: setting, culture setting, some of the things you talked about and opportunities you've had as you've seen in the past? Or do you think we're working on a hidden plan and really nothing else? So talk a little bit about kind of in GARYMIX_0122: we're working on hidden plan and really nothing else? Or talk a little bit about kind of in your current Garry Cooper vid 2: roles. GARYMIX_0122: roles, you Garry Cooper vid 2: How are founders thinking about managing team culture, team unity, if they aren't at all? GARYMIX_0122: How are founders thinking about managing team culture, team unity, if they are at all? Scott Holloway vid2: Yeah, I I think the best founders SCOTTMIX_0123: Yeah, I think the best founders do it. Scott Holloway vid2: do it. SCOTTMIX_0123: I mean, like it and this can get away from you really, really, really quickly. Like Scott Holloway vid2: I mean, like it and this can get away from you really, really, really quickly. Like SCOTTMIX_0123: if you don't instill basically like standards of excellence Scott Holloway vid2: if you don't instill basically like standards of excellence Garry Cooper vid 2: Mm-hmm. GARYMIX_0122: Mm-hmm. Scott Holloway vid2: in work early, SCOTTMIX_0123: in work early, Scott Holloway vid2: it can erode very, very quickly. And I've seen that. I think the best founders are super intentional about that SCOTTMIX_0123: it can erode very, very quickly. And I've seen that. I think the best founders are super intentional about that Scott Holloway vid2: from the beginning. And whether it's having a written SCOTTMIX_0123: from the beginning. And whether it's having a written Scott Holloway vid2: you know, set of values SCOTTMIX_0123: know, set of values Scott Holloway vid2: or not, it's just like here is how we work here. SCOTTMIX_0123: or not, it's just like here is how we work here. is how we treat each other, here is the expected level. Scott Holloway vid2: is how we treat each other, here is the expected level. GARYMIX_0122: Mm-hmm. Garry Cooper vid 2: Mm-hmm. SCOTTMIX_0123: of Scott Holloway vid2: of output, would you put your name on every single piece of work that you deliver? And I still so yeah to this day, yeah, the best founders are super intentional about that. But it all starts from the founder. SCOTTMIX_0123: output, would you put your name on every single piece of work that you deliver? And I still so yeah to this day, yeah, the best founders are super intentional about that. But it all starts from the founder. Scott Holloway vid2: startups are basically pieces of a founder's personality. SCOTTMIX_0123: startups are basically pieces of a founder's personality. GARYMIX_0122: Mm-hmm. Garry Cooper vid 2: Mm-hmm. Scott Holloway vid2: just you get Gary Jeremy, you guys have run companies and like it or not, the way you behave and your behavior, it permeates the organization and people behave like you. SCOTTMIX_0123: just you get Gary Jeremy, you guys have run companies and like it or not, the way you behave and your behavior, it permeates the organization and people behave like Garry Cooper vid 2: Okay GARYMIX_0122: Mm-hmm. SCOTTMIX_0123: you. Jeremie Bacon vid 2: So I was gonna ask then one more question, Scott, about culture. And then I've got 400 other questions I'd love to to to to pick your brain on. But one of those is in rapidly growing companies, and I've experienced I'm sure Gary's experienced, you have to experience this at certain points along the way. JBMIX_0121: So I was gonna ask then one more question, Scott, about culture. And then I've got four hundred other questions I'd love to to to to pick your brain on. But one of those is, in rapidly growing companies, and I've experienced this, I'm sure Gary's experienced, you have to experience this. At certain points along the way, GARYMIX_0122: Yeah. Garry Cooper vid 2: You JBMIX_0121: culture can start to deteriorate. Jeremie Bacon vid 2: Culture can start to deteriorate because of the pressure of growth, right? JBMIX_0121: Because of the pressure of growth, right? Jeremie Bacon vid 2: and so I always used to tell look, we're teammates, we're not family, right? JBMIX_0121: and so I always used to tell people look, we're teammates, we're not family, right? but in my opinion, teammates should feel like family. Jeremie Bacon vid 2: but in my opinion, teammates should feel like family. and what I what I mean by teammate not family equals JBMIX_0121: and what I what I mean by teammate not family equals Jeremie Bacon vid 2: We don't have to like each other. Like that's the part that's like family. We have to love each other, JBMIX_0121: we don't have to like each other. Like that's the part that's like family. We have to love each other, have to tolerate each other, we have to really get in there and like go to bat for each other. Jeremie Bacon vid 2: have to tolerate each other, we have to really get in there and like go to bat for each other. JBMIX_0121: and so Jeremie Bacon vid 2: and so, JBMIX_0121: we're not always gonna get along and that's okay. It's also fine to hire people that are not gonna get along with everybody else, as long as everyone's fighting the same fight, believes in the same culture, believes in the product, believes in each other, that's totally cool. I think about the best sports teams, half the athletes are like going at each other all day long, but they're doing it out of respect to be better. They want to be pushed, they want to push, right? So having said it's a bit of a long preamble, sometimes Jeremie Bacon vid 2: we're not always gonna get along, and that's okay. It's also fine to hire people that are not gonna get along with everybody else, as long as everyone's fighting the same fight, believes in the same culture, believes in the product, believes in each other, that's totally cool. I think about the best sports teams, half the athletes are like going at each other all day long, but they're doing it out of respect to be better. They want to be pushed, they want to push, right? So having said it's a bit of a long preamble, sometimes GARYMIX_0122: Mm-hmm. Garry Cooper vid 2: Mm-hmm. Mm-hmm. GARYMIX_0122: Mm-hmm. Jeremie Bacon vid 2: That healthy friction that we can intentionally create by setting up teams for success in high pressure, high growth environments can also really start to deteriorate quickly. I'm curious if you ever had to push pause JBMIX_0121: That healthy friction that we can intentionally create by setting up teams for success in high pressure, high growth environments can also really start to deteriorate quickly. I'm curious if you ever had to push pause in a team environment or in another way at one of your companies, whether it's Foxtrot or Instacart or Jeremie Bacon vid 2: in a team environment or in another way at one of your companies, whether it's Foxtrot or Instacart or even some of the companies that you've invested in and you're working with now as an investor, and then how you do that? How do you intervene without crushing the growth, without derailing the company? JBMIX_0121: even some of the companies that you've invested in and you're working with now as an investor, and and then how you do that? How do you intervene without crushing the growth, without derailing the company? Jeremie Bacon vid 2: And without losing the people. JBMIX_0121: And without losing the people. Scott Holloway vid2: First of all, I think you're spot on. I don't think the best companies are families. I think they're sports teams. that that's the Netflix motto. we are a sports team. the coolest thing about sports teams is they are the most meritocratic organizations on earth. the best people play. SCOTTMIX_0123: First of all, I think you're spot on. I don't think the best companies are families. I think they're sports teams. that that's the Netflix motto. we are a sports team. the coolest thing about sports teams is they are the most meritocratic organizations on earth. the best people play. GARYMIX_0122: Mm-hmm. Yeah. Mm-hmm. Scott Holloway vid2: and I think how you balance that, Jeremy, is like the the idea of being both demanding but supportive. And so having a super demanding SCOTTMIX_0123: and I think how you balance that, Jeremy, is like the the idea of being both demanding but supportive. And so having a super demanding Scott Holloway vid2: culture of expectations. But like we're gonna support you like to get there. And like SCOTTMIX_0123: culture of expectations. But like we're gonna support you like to get there, and like Scott Holloway vid2: we've got your back. And where I've seen actually culture get away. SCOTTMIX_0123: we've got your back. And where I've seen actually culture get away. I've seen it in a bunch of different ways, but I've seen it actually of complacency, not people getting burnt out. So I remember when we raised around 2 billion posts at Instacart. Scott Holloway vid2: I've seen it in a bunch of different ways, but I've seen it actually of complacency, not people getting burnt out. So I remember when we raised around a two billion posts at Instacart. SCOTTMIX_0123: and Scott Holloway vid2: and SCOTTMIX_0123: like everyone like went crazy and it was like this super exciting thing. But me, I'm I'm sort of like a pessimist in a way, and like I know our PL, I know our burn, and I'm like, Scott Holloway vid2: like everyone like went crazy and it was like this super exciting thing. But me, I'm I'm sort of like a pessimist in a way, and like I know our PL, I know our burn, and I'm like, this is crazy. And like you did then see people join the company. SCOTTMIX_0123: this is crazy. And like you did then see people join the company. for reasons of hey, an IPO is coming and this is super great. And the bar deteriorates. And so my favorite all hands that a Porva ever ran at Instacart was we moved into this brand new office on Beale Street in San Francisco. And he's like, You guys like the new office? Is it great? Yeah, you guys like it. And then he and he put up our income statement. And he goes, You like that red? He's like, You like all that red too? He's like, this is where we're at. And he's like, we are so far from having made it. And he's like, everyone needs to reset, Scott Holloway vid2: For reasons of hey, an IPO is coming and this is super great. And the bar deteriorates. And so my favorite all hands that a Porva ever ran at Instacart was we moved into this brand new office on Beale Street in San Francisco. And he's like, You guys like the new office? Is it great? Yeah, you guys like it. And then he and he put up our income statement. And he goes, You like that red? He's like, You like all that red too? He's like, This is where we're at. And he's like, We are so far from having made it. And he's like, everyone needs to reset, Jeremie Bacon vid 2: Yeah. Taunting JBMIX_0121: Yeah. Taunting Jeremie Bacon vid 2: Yeah. JBMIX_0121: Yeah. SCOTTMIX_0123: sit back Scott Holloway vid2: sit back SCOTTMIX_0123: down and let's go. I'm happy that you're pumped and I'm happy we've raised 200 million dollars. But like Scott Holloway vid2: down and let's go. I'm happy that you're pumped and I'm happy we've raised 200 million dollars, but like. SCOTTMIX_0123: We are still a going concern. And so let's get our act together. Scott Holloway vid2: We are still a going concern, and so let's get our act together. Jeremie Bacon vid 2: Yeah, we got a long way to JBMIX_0121: Yeah, we got a long way to Garry Cooper vid 2: Mm-hmm. JBMIX_0121: go. Yeah. Yeah. Totally. Jeremie Bacon vid 2: go. Yeah. Yeah. Totally. Garry Cooper vid 2: Yeah, and maybe if I can add a counter thought, which is controversial in our place. GARYMIX_0122: Yeah, and and and maybe if I can add a counter thought, which is controversial now, but Jeremie Bacon vid 2: Do it, let's do it. JBMIX_0121: Do let's do it. Garry Cooper vid 2: And GARYMIX_0122: and maybe you were actually getting there, Scott, Garry Cooper vid 2: maybe you were actually getting there, Scott, which is GARYMIX_0122: which is you gotta be able to push people Garry Cooper vid 2: you got to be able to push people GARYMIX_0122: and have a culture that's like self demanding, right? Garry Cooper vid 2: and have a culture that's like self demanding, right? But then it's also, think for me as an operator, reading the room. GARYMIX_0122: but then it's also I think for for me as an operator, reading the room. Garry Cooper vid 2: So there's a few times where I think in the last six years, GARYMIX_0122: So there's a few times where I think in the last six years, I think I've been coaching CEOs and myself to read the room, COVID being one. Garry Cooper vid 2: I think I've been coaching CEOs and myself to read through COVID being one. GARYMIX_0122: the honestly the SVB crisis being another. And so there's there's a macro effect happening to people at in their homes Garry Cooper vid 2: Honestly, the SVB crisis being another. And so there's like, there's a macro effect happening to people in their homes that plays on their ability to execute at work. GARYMIX_0122: that plays on their ability to execute at work. Garry Cooper vid 2: And so when you have a demanding culture, you're trying to grow top line, you're trying to hit plan, you're trying to go above plan. GARYMIX_0122: And so when you have a demanding culture, you're trying to grow top line, you're trying to hit plan, you're trying to go above plan. If one is doing that consistently, Garry Cooper vid 2: If one is doing that consistently, GARYMIX_0122: without kind of thinking about the moment, the broad their broader Garry Cooper vid 2: without thinking about the moment their broader human employees live in, sometimes it can come on deaf ears, or sometimes people get burned out. GARYMIX_0122: human employees live in. Sometimes it can come on deaf ears, and sometimes people get burned out. And really the best people have lots of job opportunities. And I've always been very protective not to try to burn out my people because I know they can, you know, turn on LinkedIn and find another job really quickly. So how do you think about that kind of pull and tug of like, yeah, Garry Cooper vid 2: And really, the best people have lots of job opportunities. And I've always been very protective not to try to burn out my people, because I know they can, yeah, turn on LinkedIn and find another job really quickly. how do you think about that kind of pull and tug of like, yeah, GARYMIX_0122: we're burning money every day. We wake up and breathe. We got to make progress. But as a leader, I have to think about the kind of the Garry Cooper vid 2: we're burning money every day we wake up and breathe, we got to make progress. But as a leader, I have to think about the kind of the aggregate psyche of my team and make sure that I'm reading this room. GARYMIX_0122: psyche of my team and make sure that I'm quote reading this room. Scott Holloway vid2: Totally. you have to be compassionate. people aren't gonna listen to you and people aren't gonna follow your lead if you don't actually care about people. And you have to understand who their kids are, who their spouses are, like what they like, and you have to have compassion. But at the same time, SCOTTMIX_0123: Totally. you have to be compassionate. people aren't gonna listen to you and people aren't gonna follow your lead if you don't actually care about people. And you have to understand who their kids are, who their spouses are, like what they like, and you have to have compassion. But at the same time, GARYMIX_0122: Mm-hmm. Garry Cooper vid 2: Mm. GARYMIX_0122: Right. Garry Cooper vid 2: Hey Mm. GARYMIX_0122: Yeah. SCOTTMIX_0123: growth can solve all problems. Scott Holloway vid2: growth can solve all problems. and if you are winning as a company, SCOTTMIX_0123: and if you are winning as a company, Garry Cooper vid 2: Mm-hmm. Mm-hmm. GARYMIX_0122: Mm-hmm. Mm-hmm. Scott Holloway vid2: people are happy. Yeah, yeah. SCOTTMIX_0123: people are happy. Yeah, yeah. Jeremie Bacon vid 2: Yeah, revenue hides all mistakes. Yeah. JBMIX_0121: Yeah, revenue hides all mistakes. Yeah. Garry Cooper vid 2: Yes, GARYMIX_0122: Yes. One Garry Cooper vid 2: one of my friends, one of the early Uber's told me that they were growing at 3 % a day, which is crazy to think about. GARYMIX_0122: one of my friends, one of their oo early Uberers told me that they were growing at three percent a day, which is crazy to think about. SCOTTMIX_0123: Yeah, it's insane. That's that's insane. Scott Holloway vid2: Yeah, it's insane. That's that's insane. Jeremie Bacon vid 2: Big. GARYMIX_0122: but so many problems, but no one really cared because we're Gare, they're like we're she's like, We were growing three percent a day, which I've never heard of in my career. So Garry Cooper vid 2: so many problems, but no one really cared because we're, Gary, they're like, she's like, we were growing 3 % a day, which I never heard of in my career. Scott Holloway vid2: Yeah. Yeah. And so if if you SCOTTMIX_0123: Yeah. Yeah. And so if if you if if you can Scott Holloway vid2: if if you can SCOTTMIX_0123: generate an engine of like that wins, that can solve a lot of this stuff. Now, of course, most things go wrong in in in companies too. And that's where compassion comes in and being able to like say, hey, this is gonna work out like in the long term. And I think optimism as a leader is very important. Like be a short term pessimist in terms of like demanding results, but a long-term optimist that like everything is going to work to work out. Scott Holloway vid2: generate an engine of like that wins, that can solve a lot of this stuff. Now, of course, most things go wrong in in in companies too. And that's where compassion comes in and being able to say, hey, this is gonna work out in the long term. And I think optimism as a leader is very important. be a short-term pessimist in terms of demanding results, but a long-term optimist that everything is going to work to work out. GARYMIX_0122: Mm-hmm. Garry Cooper vid 2: Mm-hmm. Jeremie Bacon vid 2: Okay, so I've a I'm gonna transition based on what you just said and and our conversation here about culture and and teams and teamwork and stuff is hard and we have to be compassionate, but also just GSD, right? JBMIX_0121: Okay, so I've a I'm gonna transition based on what you just said and and our conversation here about culture and and teams and teamwork and stuff is hard and we have to be compassionate, but also just GSD, right? Garry Cooper vid 2: Thank you. JBMIX_0121: as an investor, when you look back at being an operator, Jeremie Bacon vid 2: as an investor, when you look back at being an operator, JBMIX_0121: are there things that you look for Jeremie Bacon vid 2: are there things that you look for in a JBMIX_0121: in a founding team and in the C suite or executive team of a company you're diligent? Jeremie Bacon vid 2: founding team and in the C suite or executive team of a company you're diligent in? That don't show up in a pitch deck and how how do you suss those things out? what's the most important thing to you? Is it giving them a case study? Is it putting them through the ring or is it taking him to dinner? what is it that you do to get to the heart of the team and really understand who these people are? JBMIX_0121: That don't show up in a pitch deck and how how do you suss those things out? what's the most important thing to you? Is it giving them a case study? Is it putting them through the ring or is it taking him to dinner? what is it that you do to get to the heart of the team and really understand who these people are and how Scott Holloway vid2: Yeah, I'd love your guys' take on that too, as investors. SCOTTMIX_0123: Yeah, I'd love your guys' take on that too, as investors. I think like meeting people in person Scott Holloway vid2: I think meeting people in person is really important. SCOTTMIX_0123: is really important. and like what is the origin story? Like, what is the reason you are starting this business? I think that is very important. Scott Holloway vid2: and like what is the origin story? Like, what is the reason you are starting this business? I think that is very important. and the best operators have this sense of an air of inevitability of like, look, man, co-ahead, like best founders rather. Like you you can invest, like sure, come on, like this train is moving. SCOTTMIX_0123: and the best operators have this sense of an air of inevitability of like, look, man, go ahead, best founders rather. Like you you can invest, like sure. Come on, like this train is moving. GARYMIX_0122: Yeah, Garry Cooper vid 2: I'm going to switch over to this. GARYMIX_0122: it's a good question. SCOTTMIX_0123: With or without you. And I am doing Scott Holloway vid2: With or without you. And I am doing SCOTTMIX_0123: this until my eyes bleed. And I'd love to have you on board, but I don't really care. And here's why, here's the insight I see in the world. And I am going to fight to bring it to reality because I see this glimpse of the future that no one else sees yet. And then I think how you can see that maybe where I invest at the seed stage is like also the speed of iteration. how fast is this founder moving? How fast has progress been from the last two weeks since I've talked to them? And I would say speed. Scott Holloway vid2: this until my eyes bleed. And I'd love to have you on board, but I don't really care. And here's why, here's the insight I see in the world. And I am going to fight to bring it to reality because I see this glimpse of the future that no one else sees yet. And then I think how you can see that maybe where I invest at the seed stage is like also the speed of iteration. how fast is this founder moving? How fast has progress been from the last two weeks since I've talked to them? And I would say speed. GARYMIX_0122: Mm-hmm. Mm-hmm. Mm-hmm. Mm-hmm. Garry Cooper vid 2: you SCOTTMIX_0123: is one of the best, at least where I invest, predictors of long term success. Scott Holloway vid2: is one of the best, at least where I invest, predictors of long term success. GARYMIX_0122: Mm-hmm. Garry Cooper vid 2: Mm-hmm. JBMIX_0121: Move fast and get stuff done. Okay. How about g did you have an idea there, Gary? Jeremie Bacon vid 2: Move fast and get stuff done. Okay. How about g did you have an idea there, Gary? Garry Cooper vid 2: I love it. GARYMIX_0122: I love it. It's actually it's actually rooted in what Scott was saying before. I I think the role of a CEO founder boils down to the head of all sales, right? Whether you're selling someone to come work, whether you're selling an investor to invest, whether you're literally selling your product or your service. And so when I'm talking to a founder, I like to feel however it is in their body, that they're pitching me. Like they're th like I could see myself coming to work for you or Garry Cooper vid 2: It's actually rooted in what Scott was saying before. I think the role of a CEO founder boils down to the head of all sales. Whether you're selling someone to come work, whether you're selling an investor to invest, whether you're literally selling your product or your service. And so when I'm talking to a founder, like to feel however it is in their body that they're pitching me. Like I could see myself coming to work for you or... I could see you convincing me of something. And it's actually one of my passions for, scientists and engineers who have not found themselves in boardrooms and around P &Ls. I think they lose this confidence as a CEO founder that they can't sell. And I'm actually the ingredients to selling, you know, are quite human. GARYMIX_0122: I can see you convincing me of something. And it's actually one of my passions for, you know, scientists and engineers who've not found themselves in boardrooms and around P and Ls. I think they lose this confidence as a CEO founder that they can't sell. And I'm actually the the the ingredients to selling, you know, are are quite human. so for me, like one of the things I look forward to outside of the things that Scott said, which I Garry Cooper vid 2: so for me, like one of the things I look forward to outside of the things that Scott said, which I Or if I can't understand the why of this business and why you have this business and the kind of out at the beginning, it's really like, are you a good salesman of this thing that you're going to spend the next decade or two GARYMIX_0122: Or if I can't understand the why of this business and why you of this business and the kind of out at the beginning, it's really like, are you a good salesman of this thing that you're gonna spend the next decade or two Garry Cooper vid 2: busting your behind to get done? And if you're not, then I'm not, it's not clear to me that you're going to be able to actually pull the business forward. What about you, Jeremy? GARYMIX_0122: busting your behind to get done? And if you're not, then I'm not it's not clear to me that you're gonna be able to actually pull the business forward. What about you, Jeremy? JBMIX_0121: I think the only thing I would add to all the things that you guys have just said is a comment and remark, which is Jeremie Bacon vid 2: I think the only thing I would add to all the things that you guys have just said is a comment and remark, which is it comes down to knit, K N I T, JBMIX_0121: it comes down to knit, K N I T. Jeremie Bacon vid 2: which stands for knowledge, network, integrity, and tenacity. So JBMIX_0121: which stands for knowledge, network, integrity and tenacity. So Jeremie Bacon vid 2: what I am looking for when you get down to it is does this person andor the team, and not just the executive team, but the team that they've surrounded themselves with, do they have among them JBMIX_0121: what I am looking for when you get down to it is does this person andor the team, and not just the executive team, but the team that they've surrounded themselves with, do they have among them? Jeremie Bacon vid 2: The knowledge to do the JBMIX_0121: The knowledge to do the Jeremie Bacon vid 2: job, right? To get it done. Like some of the best founding CEOs are not the master technologist. They're not the PhD. They're not the person that's done it for 20 years. They Steve Wozniak, Steve Jobs, right? Like you need them both, right? You need the person that can tinker and do the thing, and you need the person that can go out there and sell the vision. and that's usually not in one person. Sometimes it is, those are rare, but they also usually don't last beyond seed. JBMIX_0121: right? To get it done. Like some of the best founding CEOs are not the master technologist. They're not the PhD. They're not the person that's done it for 20 years. They Steve Wozniak, Steve Jobs, right? Like you need them both, right? You need the person that can tinker and do the thing, and you need the person that can go out there and sell the vision. and that's usually not in one person. Sometimes it is, those are rare, but they also usually don't last beyond seed, GARYMIX_0122: Mm-hmm. Garry Cooper vid 2: Thank you. JBMIX_0121: maybe series A. Most people just they can't. Jeremie Bacon vid 2: Maybe series A. Most people just they can't be that forever. And that's totally awesome. You it's great. JBMIX_0121: be that forever. And that's totally awesome. You it's great. Garry Cooper vid 2: We're good. GARYMIX_0122: Right. JBMIX_0121: So I'm always looking for does this team have the knowledge and network? The network piece is like, do they have connections in industry? Jeremie Bacon vid 2: So I'm always looking for does this team have the knowledge and network? The network piece is like, do they have connections in industry? JBMIX_0121: Do they have connections into the right Jeremie Bacon vid 2: Do they have connections into the right capital partners? Usually they have some of them, no one has them all. And so it's like the next piece I look at, aside from do they have integrity and are they tenacious enough to get it done? Do they have the humility? JBMIX_0121: capital partners? Usually they have some of them. No one has them all. And so it's like the next piece I look at, aside from do they have integrity and are they tenacious enough to get it done? Do they have the humility GARYMIX_0122: Mm-hmm. JBMIX_0121: that it takes to recognize that although I will do whatever it takes to win, I do not know what I do not know. Jeremie Bacon vid 2: That it takes to recognize that although I will do whatever it takes to win, I do not know what I do not know. Garry Cooper vid 2: Right. Scott Holloway vid2: Yep. JBMIX_0121: And I'm humble enough to beg for help. I will get on my hands and knees and beg you for help because I want to do this so badly. I know it's gonna happen. I need your help to realize it. I love that when you can combine humility with this I hate arrogance, but I love just I'm gonna freaking do it, man. It's gonna happen. It's inevitable. There's Jeremie Bacon vid 2: And I'm humble enough to beg for help. Like I will get on my hands and knees and beg you for help because I want to do this so badly. I know it's gonna happen. I need your help to realize it. I love that when you can combine humility with this, I hate arrogance, but I love like just I'm gonna freaking do it, man. It's gonna happen. It's inevitable. GARYMIX_0122: Right. Mm-hmm. Garry Cooper vid 2: Mm-hmm. Mm-hmm. Thanks for watching! Jeremie Bacon vid 2: There's just nothing that's gonna stop me, but please help me get there because I don't know this, this, this, this and this, right? I love that in a team. yeah. JBMIX_0121: just nothing that's gonna stop me, but please help me get there because I don't know this, this, this, this, and this, right? I love that in a team. yeah. GARYMIX_0122: Mm-hmm. Garry Cooper vid 2: Mm-hmm. Mm-hmm. Mm-hmm. Scott Holloway vid2: No, I think that that's spot on. SCOTTMIX_0123: No, I think that that's spot on. Peter Thiel always says like he looks for these paradoxes and that is a great, really great example of that of being h humble but arrogant, in the s in the same way, what you're trying to say. I think that's a a really great balance in Scott Holloway vid2: Peter Thiel always says like he looks for these paradoxes. And that is a great, really great example of that, of being humble but arrogant, like in the s in the same way, like what you're trying to say. Like I think that's a really great balance. Jeremie Bacon vid 2: Yeah. Yeah. JBMIX_0121: Yeah. Yeah. SCOTTMIX_0123: an entrepreneur. Jeremie Bacon vid 2: Yeah, it's like Muhammad Ali, right? I'm inevitable, baby. But but he also worked like nobody else, right? And also got help where he needed it. that's that's that's beautiful. And that's what we should I to me, that's what we should strive for, right? be the best of the thing you do, and you 'cause you're never gonna be the best. You gotta keep working to be the best and help get get the help where you can from those around you to get you there. JBMIX_0121: Yeah, it's like Muhammad Ali, right? I'm inevitable, baby. But but he also worked like nobody else, right? And also got help where he needed it. that's that's that's beautiful. And that's what we should I to me that's what we should strive for, right? be the best of the thing you do and you're 'cause you're never gonna be the best. You gotta keep working to be the best and help get get the help where you can from those around you to get you there. So GARYMIX_0122: Mm-hmm. Mm-hmm. Garry Cooper vid 2: Mm-hmm. Mm-hmm. Eh-heh. GARYMIX_0122: Mm-hmm. Garry Cooper vid 2: Jeremy, I ask you, Scott's worked for what I think are some legendary CEOs. GARYMIX_0122: Jimmy can I ask, Scott's worked for some what I think are some legendary CEOs. Jeremie Bacon vid 2: Yeah, he has. JBMIX_0121: Yeah, yes. GARYMIX_0122: you know, at Instacart and I mean Ryan Peterson is one of my all-time favorite CEOs to to learn from, to listen to. Garry Cooper vid 2: Me and I, Instacart, I mean, Ryan Peterson is one of my all-time favorite CEOs to learn from, to listen to. GARYMIX_0122: you know, I'm good friends with Mike at Fox Fox Rat. So I'm curious, Scott, like if you'd pick Garry Cooper vid 2: You know, I'm good friends with Mike at FoxTrots. So, I'm curious, Scott, like, if you had to GARYMIX_0122: all your top three spots that you you your career has led you to, what are one liners Garry Cooper vid 2: call it your top three spots that your career has led you to, what are one-liners GARYMIX_0122: or one attribute from each one of those CEOs? Garry Cooper vid 2: one attribute from each one of those CEOs? that you think that you really picked up and this is what their good looks like. GARYMIX_0122: that you think that you really picked up and this is what their good looks like. Scott Holloway vid2: yeah. Ryan had this cool line around success compounds. SCOTTMIX_0123: yeah. Ryan had this cool line around success compounds. once you start to win, Scott Holloway vid2: once you start to win, SCOTTMIX_0123: winning begets winning. And so just like compound these small little wins. And I think that's true in people's like personal lives, professional lives, but also with inside companies. Aporva was incredibly strategic at seeing the field. Like he was Scott Holloway vid2: winning begets winning. And so just like compound these small little wins. And I think that's true in people's like personal lives, professional lives, but also with inside companies. Aporva was incredibly strategic at seeing the field. Like he was Garry Cooper vid 2: Mm-hmm. GARYMIX_0122: Mm-hmm. SCOTTMIX_0123: very smart about who he raised money from. Like he basically raised money from all of Sand Hill Road intentionally. Scott Holloway vid2: very smart about who he raised money from. Like he basically raised money from all of Sand Hill Road intentionally. SCOTTMIX_0123: Because who's going to fund another delivery company when Sequoia, Excel, Andreessen, Kleiner, Bond are all and so he basically boxed out competitors for a while. And so that was really interesting. And then Mike has some of the best taste of anyone I have ever met, just understanding culture. Every product on that store is him to this day. it's him. It's what he likes. And that is his level of detail is like investment banker background. he has both that left and right side of the brain. And he Scott Holloway vid2: Because who's going to fund another delivery company when Sequoia, Excel, Andreessen, Kleiner, Bond are all and so he basically boxed out competitors for a while. And so that was really interesting. And then Mike has some of the best taste of anyone I have ever met, just understanding culture. Every product on that store is him to this day. it's him. It's what he likes. And that is his level of detail, is like investment banker background. he has both that left and right side of the brain. And he GARYMIX_0122: Mm-hmm. Garry Cooper vid 2: Mmmmm JBMIX_0121: in Garry Cooper vid 2: Smart. Smart. GARYMIX_0122: Smile. Smile. Mm-hmm. Mm-hmm. Garry Cooper vid 2: He SCOTTMIX_0123: That's a great example of just caring down to where he approves what goes on those shelves. Scott Holloway vid2: That's a great example of just caring down to where he approves what goes on those shelves. Jeremie Bacon vid 2: Okay. I think that we should break out the blitz. Are you guys Scott, are you open? Are you open to answering a few boardroom blitz questions? JBMIX_0121: Okay, I think that we should break out the blitz. Are you guys Scott, are you open in are you open to answering a few boardroom blitz questions? Garry Cooper vid 2: Yes! GARYMIX_0122: Y Scott Holloway vid2: Bring it. Bring it. SCOTTMIX_0123: Bring it. Garry Cooper vid 2: No, no, no, GARYMIX_0122: well for me. JBMIX_0121: Bring it. Jeremie Bacon vid 2: Bring it. I think Gary is Gary is initiating the Blitz today, which makes me very excited, very happy to watch the spinner spin. JBMIX_0121: I think Gary is Gary's initiating the blitz today, which makes me very excited, very happy to watch the spinner spin. Garry Cooper vid 2: So GARYMIX_0122: S so Scott, this is how the blitz goes in my hands. What's gonna happen is I'm gonna click this big green button here, see? It's gonna come out. I'm gonna read you a question that you can clearly read yourself, and then you're gonna answer you're gonna answer it. So here we go. We're gonna initiate the blitz. It's a game show. Thank you, AI. so Scott, what's the best piece of career advice? Garry Cooper vid 2: Scott, this is how the Blitz goes in my hands. What's going to happen is I'm going click this big green button here, see? It's going to come out. I'm going to read your question that you can clearly read yourself, and then you're going to answer it. So here we go. We're going to initiate the Blitz. It's a game show. Thank you, AI. So Scott, what's the best piece of career advice? SCOTTMIX_0123: All right. It's like a it's like a game show. Scott Holloway vid2: All right. It's like a it's like a game show. JBMIX_0121: It is a game show. Yeah. Jeremie Bacon vid 2: It is a game show. Yeah. Garry Cooper vid 2: you've given to someone else that you wish you had followed yourself. GARYMIX_0122: You've given to someone else that you wish you had followed yourself. SCOTTMIX_0123: I've had a pretty risk-on career, very intentionally, but I still wish I took more risk. And I think people underestimate how risky certain risks or overestimate how risky certain risks are. And you only have kind of a finite period of time in your life where you can take massive swings. And so I would tell anybody who has interest in entrepreneurship to start a company in college. That is my biggest regret. Yes, it will almost certainly fail. Start a company in college. You will never have more time. Scott Holloway vid2: I've had a pretty risk-on career, very intentionally, but I still wish I took more risk. And I think people underestimate how risky certain risks or overestimate how risky certain risks are. And you only have kind of a finite period of time in your life where you can take massive swings. And so I would tell anybody who has interest in entrepreneurship to start a company in college. That is my biggest regret. Yes, it will almost certainly fail. Start a company in college. You will never have more time. GARYMIX_0122: Mm. SCOTTMIX_0123: more smart people around you and more people who want to help you. and that's a big thing. At some point in your life, no one wants help you. because you should be able to figure it out on your own. And so I think start a company in college. Exactly. Yeah. Scott Holloway vid2: more smart people around you and more people who want to help you. and that's a big thing. At some point in your life, no one wants help you. because you should be able to figure it out on your own. And so I think start a company in college. Exactly. Yeah. GARYMIX_0122: Mm-hmm. Mm-hmm. Garry Cooper vid 2: Mm-hmm. Mm-hmm. Jeremie Bacon vid 2: That and everyone's too busy with their own stuff, right? JBMIX_0121: That and everyone's too busy with their own stuff, right? Jeremie Bacon vid 2: so Yep. I love that advice. JBMIX_0121: so Yep. I love that advice. GARYMIX_0122: I love that. Okay. Garry Cooper vid 2: I love that. Okay. GARYMIX_0122: Yeah, just just to riff on that for a second, it's actually one of the things I most like about what Sam Altman has said. Well he said that when he was at YC, but in general he's like, I think people just get risk all wrong early on, that they should be taking way more risk. so thanks for sharing that, Scott. Okay, Jeremy, I'll click for you. Garry Cooper vid 2: Yeah, just to riff on that for a second. It's actually one of the things I most like about what Sam Altman said. He said that when he was at YC, but in general, he's like, I think people just get risk all wrong early on that they should be taking way more risks. So thanks for sharing that, Scott. Okay, Jeremy, I'll click for you. Jeremie Bacon vid 2: T Scotty Scotty Scotty. What's the dumbest thing you believed about the C suite before you got there? JBMIX_0121: Scotty, Scotty, Scotty. What's the dumbest thing you believed about the C suite before you got there? Scott Holloway vid2: This one is easy and it's also just about life that people have it figured out. Nobody knows what they're doing. and once you get inside these rooms, everyone is just trying to solve problems. Like you would be shocked at some of the things inside of boardrooms and with CEOs, and you assume that these are the brilliant people that know what they're doing and they don't. Like they're very smart people working hard trying to solve a problem, but no one really knows what they're doing. SCOTTMIX_0123: This one is easy and it's also just about life that people have it figured out. Nobody knows what they're doing. and once you get inside these rooms, everyone is just trying to solve problems. Like you would be shocked at some of the things inside of boardrooms and with CEOs, and you assume that these are the brilliant people that know what they're doing and they don't. Like they're very smart people working hard trying to solve a problem, but no one really knows what they're doing. Garry Cooper vid 2: EW. GARYMIX_0122: Mm. Garry Cooper vid 2: That's also Barack Obama, I thought everyone was smart and everyone was like, no one knows what to do. GARYMIX_0122: That's also Barack Obama lie, you know, I thought everyone was smart and I realized no one knows what to do. Jeremie Bacon vid 2: Doing their best. You're just doing your best not to JBMIX_0121: Doing their best. You're just doing your best not to screw it up, right? That's it. Jeremie Bacon vid 2: screw it up, right? That's it. GARYMIX_0122: Two more blitz, Jeremy. You got time for two more? Okay, my friend Scott. If your alludership style had a theme song, what would it be? Garry Cooper vid 2: Two more blitz, Jeremy. Are you down time for two more? OK, my friend Scott, if your allusion style had a theme song, what would it be? Jeremie Bacon vid 2: Seventeen more blitzes. Let's go. Yeah. JBMIX_0121: Seventeen more blitzes. Let's go. Yeah. Scott Holloway vid2: Don't stop believing. I think optimism I think optimism is very important. SCOTTMIX_0123: Don't stop believing. I think optimism I think optimism's very important. Garry Cooper vid 2: This picture is outstanding, by the way. come on, Journey. Let's go. GARYMIX_0122: This picture is outstanding, by the way. come on, Jeremy. Let's go. I love that. I love that. Jeremy, I'm also curious, what would yours be? Garry Cooper vid 2: I love that. I love that. Jeremy, I'm also curious. What would yours be? Jeremie Bacon vid 2: What if my leadership style had a theme song? What would it be? Yeah, yeah. You know what? That's a tough question for Jeremy to answer. Every time I'm asked about like what my song is for the header, they're like, I struggle because there's like a song from every genre. I don't know. What my theme song. Hmm. JBMIX_0121: What if my leadership style had a theme song? What would it be? Yeah, yeah. You know what? That's a tough question for Jeremy to answer. Every time I'm asked about like what my song is for the header, they're like, I struggle because there's like a song from every genre. I don't know. Wh my theme song. Hmm. GARYMIX_0122: Yeah. Those I believe it's pretty good. Garry Cooper vid 2: Yeah, Doth I Believe is pretty good. Hehehehehe Jeremie Bacon vid 2: Crap. JBMIX_0121: Crap. Garry Cooper vid 2: You keep thinking about I'm a blitz again. I actually don't know what mine would. Yes, The AISSI, this is super intelligent. GARYMIX_0122: You keep thinking about I'm a r I'm a I'm a I'm a I'm a blitz again. Actually don't know what mine would yes, please. The a the AIS SI, this is the super intelligent. Jeremie Bacon vid 2: All right, can I ask it? No. It came back. See, this this is this is literally the universe making fun of us. Come on. Come on. No. My theme song. JBMIX_0121: Alright, can I ask it? No. It came back. See, this this is this is literally the universe making fun of us. Come on. Come on. No. Scott Holloway vid2: Perfect. SCOTTMIX_0123: Perfect. JBMIX_0121: theme song. Okay, Scott. I read books every day all day long, if I could. I love books. I'm always curious to know what's one business book you actually finished and think everyone else should too. Jeremie Bacon vid 2: Okay, Scott. I read books like every day, all day long, if I could. I love books. I'm always curious to know what's one business book you actually finished and think everyone else should too. Scott Holloway vid2: I'm with you, Jeremy. I love books, and so it's very hard to say one. And so I will say, How will you measure your life by Clayton Christensen? SCOTTMIX_0123: I'm with you, Jeremy. I love books, and so it's very hard to say one. And so I will say, How will you measure your life by Clayton Christensen? JBMIX_0121: It is. It's impossible. Jeremie Bacon vid 2: It is. It's impossible. That's a great book. Clayton Christensen is like the man, first and foremost. We should all just read everything he's ever written. Good dude. JBMIX_0121: That's a great book. Clayton Christensen is like the man, first and foremost. We should all just read everything he's ever written. Good dude. Scott Holloway vid2: Yep. And by the way, we're all talking SCOTTMIX_0123: Yep. And by the way, we're all talking about working really hard here, which is important. But one of my favorite parts of that book is and I I know we all know people like this. There's a lot of people who are like, I'm gonna grind my face off, make a bunch of money, and then when I'm forty, I'm gonna spend a bunch of time with my kids. And it's like, hey man, your kids aren't gonna like you or know you. So maybe have some balance and that's not the way to live your life. Scott Holloway vid2: about working really hard here, which is important. But one of my favorite parts of that book is, and I I know we all know people like this. There's a lot of people who are like, I'm gonna grind my face off, make a bunch of money, and then when I'm 40, I'm gonna spend a bunch of time with my kids. And it's like, hey man, your kids aren't gonna like you or know you. So maybe have some balance and that's not the way to live your life. Jeremie Bacon vid 2: Dumb. Totally. JBMIX_0121: Totally. GARYMIX_0122: there's a there's a in the Aspen Institute, there's a required reading called Life While You Wait for for our audience. Find Google Life While You Wait. There there's no life while you wait. It's it's basically the take home. So yeah, to your point, Scott, like this let me work hard and then like enjoy kids when I'm forty five is kind of a a weird thing to cons cement. Garry Cooper vid 2: a required reading called Life While You Wait for our audience. Find Google Life While You Wait. There's no Life While You Wait. It's basically a take home. So to your point, Scott, let me work hard and then enjoy kids when I'm 45 is kind of a weird thing to cement. Scott Holloway vid2: Yeah. Jeremie Bacon vid 2: I think also JBMIX_0121: I think also Jeremie Bacon vid 2: what's weird is this whole notion that I'm gonna make a bunch of money and sit and then give it all away w before I die or when I die. also what's the point? if you're going if you've got stuff you're passionate about doing for other people, do it will you do it while you're doing it. what is the point of not sharing your talents, your time, your riches, your coin, whatever with the world while you can actually observe it being used, right, by those around you? Like, I mean, I don't I I don't get this stuff. JBMIX_0121: what's weird is this whole notion that I'm gonna make a bunch of money and sit and then give it all away before I die or when I die. also what's the point? if you're going if you've got stuff you're passionate about doing for other people, do it will you do it while you're doing it. what is the point of not sharing your talents, your time, your riches, your coin, whatever with the world while you can actually observe it being used, right, by those around you? Like, I mean, I don't I I don't get this stuff. Scott Holloway vid2: Totally. SCOTTMIX_0123: Totally. Garry Cooper vid 2: That's right. GARYMIX_0122: That's right. JBMIX_0121: All right, Scott, one more blitz. Fill in the blank. Being in the C suite is X percent inspirational and X percent something you can't say on air. Jeremie Bacon vid 2: All right, Scott, one more blitz. Fill in the blank. Being in the C-suite is X percent inspirational and X percent something you can't say on air. Garry Cooper vid 2: I haven't seen this question. SCOTTMIX_0123: Man, that's probably fifty fifty. Scott Holloway vid2: Man, that's probably fifty-fifty. JBMIX_0121: X percent inspiration and Jeremie Bacon vid 2: X percent inspiration and JBMIX_0121: X percent something you can't see on air. Jeremie Bacon vid 2: X percent something you can't see on air. Garry Cooper vid 2: Magic. Scott Holloway vid2: Fifty fifty. SCOTTMIX_0123: Fifty fifty. JBMIX_0121: 50-50. Jeremie Bacon vid 2: 50-50. JBMIX_0121: When we get off the air, I want you to tell me the word that came into your mind on the part that is something you can't say on air. Jeremie Bacon vid 2: When we get off the air, I want you to tell me the word that came into your mind on the part that is something you can't say on air. Garry Cooper vid 2: How many letters is the word? JBMIX_0121: Yeah. I'm guessing it's a phrase. It's a whole like cloud of exciting thoughts with awesome words. That's funny. Cool. I have another question for you, Scott. Thanks. Hey, first and foremost, thank you for going through the blitz. We appreciate it. okay, so you and I also share something else in common, which is our love for the University of Chicago. And Gary and I also have a love for Northwestern University. Gary's a Northwestern alum, PhD. Yay, we love it. Awesome. Jeremie Bacon vid 2: Yeah. I'm guessing it's like a phrase. It's a whole like cloud of exciting thoughts with awesome words. That's funny. Cool. I have another question for you, Scott. Thanks. Hey, first and foremost, thank you for going through the blitz. We appreciate it. okay, so you and I also share something else in common, which is our love for the University of Chicago. And Gary and I also have a love for Northwestern University. Gary's a Northwestern alum, PhD. Yay, we would love it. Awesome. Scott Holloway vid2: Ha ha ha. SCOTTMIX_0123: Ha ha ha. GARYMIX_0122: Amazing. Garry Cooper vid 2: Maison. Okay. GARYMIX_0122: Mm. Garry Cooper vid 2: Thank Jeremie Bacon vid 2: but Scott, you're an E I R at JBMIX_0121: but Scott, you're an EIR at Jeremie Bacon vid 2: University of Chicago, right? JBMIX_0121: University of Chicago, right? Jeremie Bacon vid 2: Tell about, and that's been the last couple of years. I'd love it if you could spend a couple of minutes with us talking about your experience working with specifically new want-to-be founders, right? So as part of your job as an EIR, is you get to spend lots of time with students and sometimes faculty members who are considering starting something new and trying to figure out which way they should go. I'd love it if you could share with us some of your most favorite experiences and some of the generalized advice that you that you find yourself giving to young aspiring entrepreneurs coming out of UC. JBMIX_0121: Tell about and that's been the last couple of years. I'd love it if you could spend a couple of minutes with us talking about your experience working with specifically new want-to-be founders. Right. So as part of your job as an EIR is you get to spend lots of time with students and sometimes faculty members who are considering starting something new and trying to figure out which way they should go. I'd love it if you could share with us some of your most favorite experiences and some of the the generalized advice that you that you find yourself giving to young aspiring entrepreneurs coming out of UC. SCOTTMIX_0123: Well, it's been amazing. And I think especially now, Scott Holloway vid2: Well, it's been amazing. And I think, especially now, SCOTTMIX_0123: with all of the P doom with AI and stuff of how bad the world could possibly turn out, if you wanna be optimistic and if you wanna be inspired, go talk to undergraduate students at these universities about Scott Holloway vid2: with all of the P doom with AI and stuff of how bad the world could possibly turn out, if you wanna be optimistic and if you wanna be inspired, go talk to undergraduate students at these universities about SCOTTMIX_0123: their outlook on the world and what they want to build. And that will quickly reframe your brain into be like, we're gonna be okay. And like these folks are amazing, they're super ambitious and they want to solve really, really hard problems. And so it's a good rewiring from my own brain. Scott Holloway vid2: their outlook on the world and what they want build. And that will quickly reframe your brain and to be like, we're gonna be okay. And like these folks are amazing, they're super ambitious and they wanna solve really, really hard problems. And so it's a good rewiring from my own brain. SCOTTMIX_0123: Of things are good and the next generation is gonna be much better than we have been. So that has been really special. And then what I try to push these kids to do, Jeremy, which I I've talked, what which is always my parting advice in these EIR sessions or other ones, is a lot of you won't start companies. And it's not because you don't want to. It is because you are afraid of what your mom's gonna say, your dad's gonna say, and you're gonna be jealous that your buddy at Bain is making 400 grand a year flying around first class and you're gonna have to suck it up for two years. Scott Holloway vid2: Of things are good and the next generation is gonna be much better than we have been. So that has been really special. And then what I try to push these kids to do, Jeremy, which I I've talked, what which is always my parting advice in these EIR sessions or other ones, is a lot of you won't start companies. And it's not because you don't want to. It is because you are afraid of what your mom's gonna say, your dad's gonna say, and you're gonna be jealous that your buddy at Bain is making 400 grand a year flying around first class and you're gonna have to suck it up for two years. SCOTTMIX_0123: and not go on vacation and you're gonna have to grind. But life is a long game. And if this is something you want to do, Scott Holloway vid2: and not go on vacation and you're gonna have to grind. But life is a long game. And if this is something you want to do, SCOTTMIX_0123: do not rob yourself of that on your deathbed. And if you actually want to do this, Scott Holloway vid2: do not rob yourself of that on your deathbed. And if you actually want to do this, SCOTTMIX_0123: yes, all your peers are going to go into private equity and search funds. But if this is something you want, you have to be willing to look like an idiot for a couple of years and those folks will win in the long run. Scott Holloway vid2: yes, all your peers are going to go into private equity and search funds. But if this is something you want, you have to be willing to look like an idiot for a couple of years and those folks will win in the long run. GARYMIX_0122: Mm-hmm. Mm-hmm. Garry Cooper vid 2: Hehehehehe Jeremie Bacon vid 2: I totally JBMIX_0121: I totally agree. And at the end of the day too, pursue what you love, man. Go do it. if it's something you feel passionate about, go do it. Now's the time. Go, go, go. Jeremie Bacon vid 2: agree. And at the end of the day too, pursue what you love, man. Go do it. if it's something you feel passionate about, go do it. Now's the time. Go, go, go. Scott Holloway vid2: Yeah. Garry Cooper vid 2: and so on. GARYMIX_0122: Absolutely. Garry Cooper vid 2: Be GARYMIX_0122: Be in the be in the arena. Garry Cooper vid 2: in the arena. Scott Holloway vid2: Be in the arena. SCOTTMIX_0123: Be in the arena. GARYMIX_0122: Yes. Jeremie Bacon vid 2: Yeah, JBMIX_0121: Yeah, Jeremie Bacon vid 2: for sure. Cool. I love it. I love it. Well, Scott, it has been an absolute pleasure hanging out with you this afternoon. Before we let you go, I'm curious, do you have any questions for Gary Cooper? JBMIX_0121: for sure. Cool. I love it. I love it. Well, Scott, it has been an absolute pleasure hanging out with you this afternoon. Before we let you go, I'm curious, do you have any questions for Gary Cooper? GARYMIX_0122: Ha ha ha ha. Garry Cooper vid 2: Ha ha ha ha ha ha ha ha SCOTTMIX_0123: Well, Scott Holloway vid2: Well, Mr. Cooper, you have had a very wonderful career and you are on to your next chapter. What are you most excited about switching hats from CEO to having to back CEOs and going from a job that is a lot of affirmative decisions all day to a job that is ninety-nine percent no? And how are you looking forward to that? SCOTTMIX_0123: Mr. Cooper, you have had a very wonderful career and you are on to your next chapter. What are you most excited about switching hats from CEO to having to back CEOs and going from a job that is a lot of affirmative decisions all day to a job that is ninety nine percent no? And how are you looking forward to that? GARYMIX_0122: Yes. Garry Cooper vid 2: Yes. I'm super excited, Scott. I appreciate the question. Thanks for the nod, Jerry. I'm super excited to come on to the dark side with you, Scott, because I think the world in which we'll be built over the next 10 or 20 years is going to probably be built by a lot of scientists and a of engineers GARYMIX_0122: I'm super excited, Scott. I know I I I say I appreciate the question. Thanks for the nod, Jeremy. I'm super excited to come on to the to the dark side with you, Scott, because I think the world in which we'll be built over the next ten or twenty years is gonna probably build be built by a lot of scientists and a lot of engineers JBMIX_0121: Yeah. GARYMIX_0122: who were risk on like a Garry Cooper vid 2: who are risk on like a GARYMIX_0122: fill in the blank. And I think a person like Jeremy, a person like me, Garry Cooper vid 2: fill in the blank. And I think a person like Jeremy, a person like me, who can say, take the leap from your professor, take the leap from your science research program, and let's go build a company. GARYMIX_0122: who can say, take the leap from your professorate, take the leap from your science research program and let's go build a company. Garry Cooper vid 2: I'm just really excited GARYMIX_0122: I'm just really excited to back and coach and cheer for Garry Cooper vid 2: back and coach and cheer for and door move things for those types of founders. And so though I'll be saying no more than I would like and GARYMIX_0122: and door move things for those types of founders. And so though I'll be saying no no more than I would like and Garry Cooper vid 2: I'm really excited to really back the next generation of builders who will hopefully help us live a little longer, little happier, a little healthier. GARYMIX_0122: I'm really excited to really back the next generation of of builders who will hopefully help us live a little longer, a little happier, a little healthier. Scott Holloway vid2: You guys are gonna do amazing. SCOTTMIX_0123: You guys are gonna do amazing. Jeremie Bacon vid 2: Thanks. We're gonna have lots of fun. As are you. You guys are kicking it. Killing. JBMIX_0121: Thanks. We're having lots of fun. As are you. You guys are kicking it. Killin'. Garry Cooper vid 2: Thanks, Scott. And Scott, GARYMIX_0122: Thanks Scott. And Scott, just Garry Cooper vid 2: just so you know, I always have kings for our next poker game. GARYMIX_0122: so you know, I always have kings for our next poker game. I JBMIX_0121: Right next Poker Jeremie Bacon vid 2: next booker Scott Holloway vid2: We're SCOTTMIX_0123: We're playing poker soon. JBMIX_0121: game. Jeremie Bacon vid 2: game. Scott Holloway vid2: playing poker soon. GARYMIX_0122: never have seven deuce. Jeremie Bacon vid 2: I can't wait for this next JBMIX_0121: I can't wait for this next game. Jeremie Bacon vid 2: game. Anyway. Awesome. Scott, thanks again for spending time with the family. We appreciate it. JBMIX_0121: Anyway. Awesome. Scott, thanks again for spending time with us. We appreciate it. SCOTTMIX_0123: This was awesome. Thanks, guys. Scott Holloway vid2: This was awesome. Thanks, guys. Garry Cooper vid 2: Thanks, Scott. GARYMIX_0122: Thanks, God.