The Exchanges

Q Tell me, final one, what's the most recent publicly announced investment, and why did you say yes and get so excited?

A I guess NowWith is the most recent. Albert Potkin and Nicole Winneman just announced recently that me and Alex Rodriguez invested We did take a 40% stake in the company and it's in social commerce. I think the two big areas still left untapped in retail are social commerce and conversational commerce. So those are the two areas I'm really excited about. And social commerce is basically what they've created a platform that connects brands to influencers. And so that if you're an influencer and you have a following, you can go on the platform, see all the brands and say, oh, Lululemon, I like that brand. I'm going to now create a video and Put it on my Instagram, and people can then shop off the video, and every sale that I make, I'll get dollars some percentage back to me. It's the idea of, of democratizing sort of access to any influencer to get access to brands in a seamless way. I think that's, that's a big, big opportunity.

AI assessment note: “I guess NowWith is the most recent. Albert Potkin and Nicole Winneman just announced”

Q Okay, so I always love to start with a bit of context, so tell me, how did you make your way into the world of startups, how did you make your way into the world of entrepreneurship, and what was your real start in the business?

A I was always an entrepreneur growing up, wanted to be a farmer. Ever since I can remember as a little kid, four years old, my grandma always used to tell me, no, you don't want to be a farmer, and I said, you know, yes, I do. I want to grow stuff from nothing, and that was basically carried on for years, and it turned into me being a The classic kid entrepreneur doing everything you can imagine from washing cars, mowing lawns, baseball court business, recycling, newspapers, lemonade stand, you know, everything kind of in my DNA from birth, I think, because I literally had it in me very early. My first memory of being an entrepreneur, I was really little, and it was Casper the Friendly Ghost, his little projector screen. You put the little circle things in, and it projects onto the wall. I don't even think I could write Or anything at that point, but I narrated because there was no words and I narrated it and used to charge my family to come and listen to the narration. So it was always in there. And then, you know, I, I didn't grow up with any connections to venture startup world. It didn't really exist in back in 93 when I graduated college. So there wasn't really a choice to like be an entrepreneur, didn't have money or anything like that. So I went into banking. I was good with math and like stocks and filed stocks as a kid as well. Went into banking and each year I was doin…

AI assessment note: “I was always an entrepreneur growing up... My first memory of being an entrepreneur”

Q Can I ask a weird final one? And it's like, when I listen, when I listen to you, it's like, you're just very secure in your thoughts, in your mindset, and everything's like, yeah, it's like you listen to you and like, shit, this guy's got it figured out. I guess my question to you is like, do you have insecurities today? And what are they?

A Yeah, I still have the insecurity. Like I said before, even though I'm evolved and I've done therapy and this whole, you know, thing we talked about with my dad early. I do still have, because we'll say, you know, you're doing these new startups and things, but you've made all this money. Like if it doesn't work, you're okay. I'm like, no, you don't understand. I'm not okay. I still feel like it's life or death. I still feel like love is tied to whether I succeed or not. And so even though it's definitely healthier than it was when I was younger, I still have that insecurity. Like, no, it has to work. There's no plan B. There's no fallback. There's no, it's okay. I've got plenty of money. I'll just whatever. So that's an insecurity. Like it cannot work.

AI assessment note: “I still feel like love is tied to whether I succeed or not.”

Q Go ahead. So, I mean, the first thing is like favorite book and why the truth is you don't read as you admitted earlier. I don't read either. Uh, what's your favorite way to spend your downtime? I love running.

A I spent a lot of time thinking. I actually set aside time in the day to do nothing but think. It could be with a glass of wine, it could be, you know, sitting in the hot tub, relaxing, but like try to get into a relaxed state a little bit and just literally think, but not think about what went wrong in the day, what worry about the future, think about the past, like actually just think about the world, where it's going, try and connect dots, and think about V. It's really think about the vision for different ideas, for ideas that Things I'm in, things I want to get in. I find it impossible to invent or come up with big ideas, just kind of like on the, like in between your life, like you need to like dedicate real time to it. So other people read and I think, and when I try and read, I feel like I'm taking time away from thinking. So I, that's why I always put the book down. I do try. I do try.

AI assessment note: “I spent a lot of time thinking. I actually set aside time in the day”

Q way back, you know, I heard in the How I Built This episode, your relationship with your father and growing up, you said, Something really interesting, which was you have to do something exceptional to get your father's attention. That's tough, and that's a lot of pressure for a child. How do you think that impacted you and your mindset, having to strive for that attention with these exceptional acts?

A You basically, at a young age, associate being loved with accomplishing big things. Every human seeks to be loved, and if you're loved, then you're good, right? And if you're, don't feel loved unless you do big things, you have to do big things to get loved. You have to do whatever it takes. And as a kid, Develop this mentality where I get it. I know what I need to do, and it drives you, and it's an internal motivation that you can't replicate. You can't tell somebody that doesn't have this unhealthy childhood to find that motivation. It's something that's unexplainable, but I think it's really healthy when it starts, and I think with therapy and time, I think it can morph into something that's healthy, and then it becomes an asset instead of a liability. I think earlier on, it's more of a liability than an asset, but That's how it started.

AI assessment note: “associate being loved with accomplishing big things”

Q I do want to ask, you know, we spoke about Sith Gear earlier, and you said something before, I loved your 50 lessons for life, but you said one of them, don't let fear hold you back from taking a risk. I wanted to ask, with that in mind, how do you think about your relationship to fear and risk today, and has it changed over time?

A No, I've always, you know, I grew up, again, with My parents weren't that involved. They had me when they were 20 years old, and, you know, I kind of fend for myself, and I learned a lot of lessons myself, and failed at a lot of things. And I just sort of got comfortable with failure as being, like, not a big deal. Like, I didn't get good grades in school, and it wasn't a big deal. It was like, okay, if I teach myself how to ride a bike, and fail, and crash, and it's like, get back up, and just tie my shoe, figure it out. Like, Fail. Not do it right. Get made fun of. And then you get just comfortable with, okay, it's okay to fail. Learn from it. Take those valuable lessons and be better the next time. Once you have that mentality, like failure is okay, because that's the starting point of fear. It's like failure is okay. There's nothing wrong with failing. It, I think, opens up the possibility to take more risk.

AI assessment note: “No, I've always... got comfortable with failure as being, like, not a big deal.”

Q I guess I approach it with more cynicism, where I used to be fully trusting. The minute you hire someone, you're fully trusting. Now I start from zero, and you build it from there. How would you advise me against that, and should I switch back?

A I know, like I said, you have to just see getting burned once in a while as a consequence, and I think maybe if you get burned early, or if you're gonna get burned one out of 50 times, but you get burned in your first five, you might think, oh, this is not sustainable. But I found that actually it is more like one 50. Like it's rare that you, that you will get burned and you'll get better at associating with people that are less likely to burn you. But the upside is tremendous. Like I said, if you go halfway on trusting or three quarters, you don't get the full bang. You know, I have so many examples, even in my personal life of, of like trusting somebody and them surprising you basically either in the relationship, how hard they work. There's so much upside.

AI assessment note: “if you go halfway on trusting or three quarters, you don't get the full bang.”

Q like the personality types, and when we think about it, adding to teams, you know, rarely is The chief people officer, one of the first hires, bluntly. It's often I've interviewed some of the best founders in the show. They always say a hundred plus, a hundred plus. That's kind of the kind of benchmark. But you said before, it should be your first exec hire. Why is that, Mark?

A Yeah, because, you know, I subscribe to this theory of VCP, Vision Capital People. If you get that right, if you nail VCP, everything else falls into place. The people part of it is the toughest and most challenging piece. It starts with Setting the right culture, mission, values. What does a company stand for? Create a culture where the best people in the world want to come work, but then you have to find those people. You have to recruit those people. You have to create an org structure that keeps them empowered, motivated, where you can get the very best they've got. To do all that well, org structure, compensation, recruiting, find them. Like, you need a chief people officer. Like, if you think that, or the CEO or the founder of a company thinks that they can Found the company, do the capital, do the vision, do all the parts of the business, and on the side with their pinky, do like the chief people stuff. That's not gonna work. You're not gonna create the best culture, hire the best people, have the right org structure to really get them motivated and empowered. So that's why I start with chief people now, because that whole P part of the equation is so important, and you have somebody amazing on it, everything else falls in place.

AI assessment note: “To do all that well, org structure, compensation, recruiting, find them. Like, you need a chief people officer.”

Q Go ahead. So, I mean, the first thing is like favorite book and why the truth is you don't read as you admitted earlier. I don't read either. Uh, what's your favorite way to spend your downtime? I love running.

A I spent a lot of time thinking. I actually set aside time in the day to do nothing but think. It could be with a glass of wine, it could be, you know, sitting in the hot tub, relaxing, but like try to get into a relaxed state a little bit and just literally think, but not think about what went wrong in the day, what worry about the future, think about the past, like actually just think about the world, where it's going, try and connect dots, and think about V. It's really think about the vision for different ideas, for ideas that Things I'm in, things I want to get in. I find it impossible to invent or come up with big ideas, just kind of like on the, like in between your life, like you need to like dedicate real time to it. So other people read and I think, and when I try and read, I feel like I'm taking time away from thinking. So I, that's why I always put the book down. I do try. I do try.

AI assessment note: “I spent a lot of time thinking. I actually set aside time”

Q Okay, so I always love to start with a bit of context, so tell me, how did you make your way into the world of startups, how did you make your way into the world of entrepreneurship, and what was your real start in the business?

A I was always an entrepreneur growing up, wanted to be a farmer. Ever since I can remember as a little kid, four years old, my grandma always used to tell me, no, you don't want to be a farmer, and I said, you know, yes, I do. I want to grow stuff from nothing, and that was basically carried on for years, and it turned into me being a The classic kid entrepreneur doing everything you can imagine from washing cars, mowing lawns, baseball court business, recycling, newspapers, lemonade stand, you know, everything kind of in my DNA from birth, I think, because I literally had it in me very early. My first memory of being an entrepreneur, I was really little, and it was Casper the Friendly Ghost, his little projector screen. You put the little circle things in, and it projects onto the wall. I don't even think I could write Or anything at that point, but I narrated because there was no words and I narrated it and used to charge my family to come and listen to the narration. So it was always in there. And then, you know, I, I didn't grow up with any connections to venture startup world. It didn't really exist in back in 93 when I graduated college. So there wasn't really a choice to like be an entrepreneur, didn't have money or anything like that. So I went into banking. I was good with math and like stocks and filed stocks as a kid as well. Went into banking and each year I was doin…

AI assessment note: “I was always an entrepreneur growing up, wanted to be a farmer.”

Q How do you think about fatherhood today, and do you want to imbue that to your children today? As you said, it's a driver, it's a motivator, but then there are also downsides. How do you think it impacted your parenting style today?

A Yeah, it's a really good point, and I think you have to be really careful as a parent, because this is a natural inclination to want to, like, get really excited and proud when your son or daughter does something spectacular or great or wins or, oh, that's amazing, let's go get ice cream, you won, and I mean, I would just Caution a little bit about going overboard on that and figuring out, like, whatever things you think are important, like the values, I would start with values, think are important. Those are the things to celebrate. So kindness, empathy, loyalty, these are values that are really important to me and try to instill in our kids. Our daughters have two daughters that are 18 and 21. Be a good person. And so looking for opportunities to reward and celebrate that behavior. And of course you're going to celebrate when somebody wins something. I'm not saying that. I'm saying just be more balanced about it so that it doesn't become a one-track situation.

AI assessment note: “So kindness, empathy, loyalty, these are values that are really important to me”

Q What would you most like to change about the world of VC today? You've seen it for years as an entrepreneur. Now you've got VCP. What do you most want to change about the world of venture?

A Yeah. It's very frustrating as an entrepreneur where you have different funds specialized in different rounds of financing and, you know, they don't come in seed and they come in seed, but they can only write a little check. Then you got to find another one to create a bigger check. And yeah, it's just like, come on, man, just like have a fund. And that's kind of a little bit, the VCP thing that can just come in and say like, yeah, Here's like five million seed. Here's twenty million A. Here's, you know, just like you can kind of get the company to lift off without having to worry about constantly every year having to like, you know, go out and find the next tranche of VCs that are then like specific to that round. As an entrepreneur, it's always frustrated me that I had to get like the seed investor that could put in like a million bucks, you know, and then I had a whole new group of investors that had to go like pitch.

AI assessment note: “frustrating as an entrepreneur where you have different funds specialized in different rounds”

Q most interview processes is honestly often the referencing part. Now, I tweeted about this, and you, um, disagreed with me, and, uh, when you disagreed with me, I was like, ah, shit, that's not a nobody on Twitter who disagreed with me. But, so thank you for that. But my, my question to you is like, why do you negate the importance of referencing, and what are your thoughts here?

A Yeah, I guess it depends on the purpose of the reference. So early in my career, and I see people do this, you sort of have an interview, and you have something, some tap, I call it a tap on the shoulder. Like, I'm not quite sure about this one thing. I'm going to check and find out when I talk to their references. And that's kind of the mentality. Like, there's some lingering thing you want to flush through with the references. And very frequently, the references make you feel better. It's like, oh, ok. I guess that's good, you know, and then you wind up hiring the person, and then the tap that you got winds up playing out, and so it's like a false sense of confidence there, but my point now in reference is, when I interview somebody, I need to know, without a shadow of a doubt, without having to talk to any other person, I'm that confident that this is the right person for the job, and that they exhibit the values, and if you didn't get there, interview them again. Interview them a third time. Wait until you get to a place where you're like, I'm done. This is the person. You're not going to get that From talking to a reference. It's very, very, very rare, and I talked to people about this, that you'll actually change your mind from a reference. Like, I want to hire this person, let me check the references, and then you're like, no, now I'm not going to hire the person. Or, I …

AI assessment note: “It's very, very, very rare... that you'll actually change your mind from a reference.”

Q I'm gonna be totally honest. I'm in fucking sixth gear, and I have been for a while, but this goes against something that you've kind of put in your lessons of life, and you did this, 50 amazing lessons of life, and you always said, make time for romance. Mark, I mean, tell me, do they not go in against each other, sixth gear, and always make room for romance?

A I think, There's definitely some conflict there. There's no question. I think other things have to suffer. You know, hobbies suffer. TV suffers. I can't remember the last time I watched TV. I can't remember the last time I, like, even read anything, news or otherwise. Some things, I just chose my priorities in a way that allows me to get the things that are most important done, but other things fall away. So there's no way to do it all. There's no way you're going to be, you know, having hobbies and And, you know, watching TV, and reading the news, and doing social media, and all this other stuff. Like, it's just, there's not, there's not enough time to sleep, right? I sleep eight hours a night. I think it's really important. If you want, in sixth gear, this idea of being in sixth gear and sleeping five hours a night, that doesn't work. You can't, you don't have enough energy to be in sixth gear for the remaining hours in the day.

AI assessment note: “There's definitely some conflict there. There's no question.”

Q How do you think about fatherhood today, and do you want to imbue that to your children today? As you said, it's a driver, it's a motivator, but then there are also downsides. How do you think it impacted your parenting style today?

A Yeah, it's a really good point, and I think you have to be really careful as a parent, because this is a natural inclination to want to, like, get really excited and proud when your son or daughter does something spectacular or great or wins or, oh, that's amazing, let's go get ice cream, you won, and I mean, I would just Caution a little bit about going overboard on that and figuring out, like, whatever things you think are important, like the values, I would start with values, think are important. Those are the things to celebrate. So kindness, empathy, loyalty, these are values that are really important to me and try to instill in our kids. Our daughters have two daughters that are 18 and 21. Be a good person. And so looking for opportunities to reward and celebrate that behavior. And of course you're going to celebrate when somebody wins something. I'm not saying that. I'm saying just be more balanced about it so that it doesn't become a one-track situation.

AI assessment note: “kindness, empathy, loyalty, these are values that are really important to me”

Q the new fund strategy. Well, now I'm, I'm always like English and super polite, and I'm always getting in trouble, Mark, for being too polite and not voicing my opinion. So here goes. Watch out. You said owning 40 to 80% of a business really means you don't need that many hits. I agree. How do you think about portfolio construction with the new fund then with that in mind?

A Yeah, it would be, it would be, you know, more like 15 investments. How do you put ten million seed in a company, and then the company winds up, let's say you own 40% for ten million, and then the company winds up doing a fifty million dollar round that you lead to keep your pro rata and put another 20 in. So now you've got thirty million in a company. The company's got sixty million, it's got an incredible team, it's got a Big vision in a big market with a big TAM. You basically made that happen. You, you, you've been able to have the guarantee of great people because you've got sixty million, which you can go out and recruit, assuming you got the chief people officer and you got the right founders and things. And the fifty million dollar round kicked off with 20 makes it easy to get done. And so you put thirty million in the company, you now own 40% of a company that probably has already a hundred, hundred fifty million at least. If you raise 50, maybe two or three hundred million market cap, and you sort of made that happen from a seed from nothing. You do 15 of those and have 30,000,015 companies and say half a billion dollar fund. Something like that, on that order of magnitude.

AI assessment note: “it would be, you know, more like 15 investments.”

Q want to ask, you know, another lesson that you put was make someone feel safe if you want to connect on a deeper level. I love this. But I guess my question is, what do you do deliberately to make people feel safe and make people feel like they can bring their whole selves to a conversation rather than the usual kind of facade of everything's great and I'm okay?

A Yeah, no, the values that I try and instill in the companies I start, trust, transparency, and fairness, I think apply in personal relationships too. I think trust and transparency, the two biggest. I'll assume fairness is probably a little bit more Of a corporate, although fairness stretches to inclusivity, and so I think that matters in personal relations, like accepting people for who they are, but trust and transparency, the two big ones, if you want somebody to open up and connect, show them that you're being transparent, and you're sharing information, maybe sharing things that are very personal, or, you know, the stuff we're talking about, about my dad here, and things like that, like, it's okay to be open and be transparent in that way, and then trusting that It's probably even bigger than that. It's sort of like, do you start from a place of trust when you talk to somebody, or is it trust but verify? Are you cautious? I've found, and I'm very trusting, when you openly trust someone, really trust them, like where they can burn you, like put yourself in a place where they could burn you. They rarely do. Occasionally you might get burned, and that's part of one of the consequences of being open, but there's so much more upside to trusting. The worst place to be is kind of that no man's land in the middle. Where you're kind of like half trusting, you know what I mean? Beca…

AI assessment note: “show them that you're being transparent, and you're sharing information, maybe sharing things”

Q No, they didn't at all, but they're a killer founder. They just sucked at working for people. I guess, how do you think about that? Because I, I, the people who like bounce around because they're shit employees.

A No, no, I don't. They don't even get an interview at that point. The risky part is this is, I'm telling you, this is a trap. Somebody tells you somebody's good. You look at the resume, and you don't really spend much time on it because they said this person's good, and you interview them. I do not do that. I don't care if somebody tells me they're good. There's maybe a few people in my orbit that if they've worked with somebody, they know a superstar, but it's very rare. Most people don't really understand what a superstar is, so I, for the most part, I will never take a recommendation unless the resume is Fits the description. And so, yeah, somebody who, who bounces around, somebody who doesn't get promoted in the job that they're in, think I'm a superstore. I'm top 10%. Here's what I'm doing. I'm going to work for this company. I get into Google, and I see this all the time. You're like, wow, they got a job at Google. That's a pretty good job. And then they leave in 18 months. Ow. Like, I don't even, I don't care what the excuse is. Somebody say, oh, well, there's a really good excuse. It doesn't matter. I only will focus on People that have a demonstrable level of success in any place that they work. It's true. Maybe that person has a really valid excuse, and I missed that person, but I don't know that person. I, you know what I mean? I'm just going through resumes. I'm wait…

AI assessment note: “They don't even get an interview at that point.”

Q No, they didn't at all, but they're a killer founder. They just sucked at working for people. I guess, how do you think about that? Because I, I, the people who like bounce around because they're shit employees.

A No, no, I don't. They don't even get an interview at that point. The risky part is this is, I'm telling you, this is a trap. Somebody tells you somebody's good. You look at the resume, and you don't really spend much time on it because they said this person's good, and you interview them. I do not do that. I don't care if somebody tells me they're good. There's maybe a few people in my orbit that if they've worked with somebody, they know a superstar, but it's very rare. Most people don't really understand what a superstar is, so I, for the most part, I will never take a recommendation unless the resume is Fits the description. And so, yeah, somebody who, who bounces around, somebody who doesn't get promoted in the job that they're in, think I'm a superstore. I'm top 10%. Here's what I'm doing. I'm going to work for this company. I get into Google, and I see this all the time. You're like, wow, they got a job at Google. That's a pretty good job. And then they leave in 18 months. Ow. Like, I don't even, I don't care what the excuse is. Somebody say, oh, well, there's a really good excuse. It doesn't matter. I only will focus on People that have a demonstrable level of success in any place that they work. It's true. Maybe that person has a really valid excuse, and I missed that person, but I don't know that person. I, you know what I mean? I'm just going through resumes. I'm wait…

AI assessment note: “They don't even get an interview at that point.”

Q controlling V, uh, the vision itself, I I'm totally with you. I love the unwavering vision, the persistent entrepreneur. There is sometimes a time when you're like, you know what, Mark, The world is telling us something here and the vision may be great, but the market timing is, and we need to change course. How do you think about when to stick versus when to remain with the vision?

A The strategy can change. So how you get there, the vision shouldn't change. If you do the right amount of work upfront, and I mean, a hundred plus hours crafting, thinking about the vision, talking to people, don't be afraid to share your vision because it's like a piece of clay. You got to keep molding it and molding it. You'll know, okay, the timing's right. Massive, Tam, and you'll just have a level of conviction after talking to enough people that there's something massive here. Now, the strategy, how you get there, lots of different ways. You might have to pivot. You might have to, but I can't think of a situation where you'd spend all that time on the vision and then sort of get it wrong because it's so big and you've talked to enough people and you know enough about the world to know, like, that's where the world's going. You know, it's, it's, it's hard to imagine. I guess it could happen, but Maybe it happens if you haven't done enough work on it. I don't think people spend enough time on the vision. They'll say, like, if you ask somebody, what is your vision? 10 to 15 years, where do you want to be? It's rare that somebody will be able to, like, recite a, like, really tight three to five sentences of exactly what they want to be in 10 years from now. Most people just get so caught up in kind of the day-to-day, and they have a vague thing about where they want to go, bu…

AI assessment note: “The strategy can change. So how you get there, the vision shouldn't change.”

Q What would you most like to change about the world of VC today? You've seen it for years as an entrepreneur. Now you've got VCP. What do you most want to change about the world of venture?

A Yeah. It's very frustrating as an entrepreneur where you have different funds specialized in different rounds of financing and, you know, they don't come in seed and they come in seed, but they can only write a little check. Then you got to find another one to create a bigger check. And yeah, it's just like, come on, man, just like have a fund. And that's kind of a little bit, the VCP thing that can just come in and say like, yeah, Here's like five million seed. Here's twenty million A. Here's, you know, just like you can kind of get the company to lift off without having to worry about constantly every year having to like, you know, go out and find the next tranche of VCs that are then like specific to that round. As an entrepreneur, it's always frustrated me that I had to get like the seed investor that could put in like a million bucks, you know, and then I had a whole new group of investors that had to go like pitch.

AI assessment note: “you have different funds specialized in different rounds of financing”

Q want to ask, you know, another lesson that you put was make someone feel safe if you want to connect on a deeper level. I love this. But I guess my question is, what do you do deliberately to make people feel safe and make people feel like they can bring their whole selves to a conversation rather than the usual kind of facade of everything's great and I'm okay?

A Yeah, no, the values that I try and instill in the companies I start, trust, transparency, and fairness, I think apply in personal relationships too. I think trust and transparency, the two biggest. I'll assume fairness is probably a little bit more Of a corporate, although fairness stretches to inclusivity, and so I think that matters in personal relations, like accepting people for who they are, but trust and transparency, the two big ones, if you want somebody to open up and connect, show them that you're being transparent, and you're sharing information, maybe sharing things that are very personal, or, you know, the stuff we're talking about, about my dad here, and things like that, like, it's okay to be open and be transparent in that way, and then trusting that It's probably even bigger than that. It's sort of like, do you start from a place of trust when you talk to somebody, or is it trust but verify? Are you cautious? I've found, and I'm very trusting, when you openly trust someone, really trust them, like where they can burn you, like put yourself in a place where they could burn you. They rarely do. Occasionally you might get burned, and that's part of one of the consequences of being open, but there's so much more upside to trusting. The worst place to be is kind of that no man's land in the middle. Where you're kind of like half trusting, you know what I mean? Beca…

AI assessment note: “show them that you're being transparent, and you're sharing information, maybe sharing things”

Q Do you see commonalities in the best chief people officers you've worked with, you've seen in investments, Across the board, are there commonalities in what makes the best and what people should look for in their first CPO? What do you look for when you meet candidates?

A I just think people that understand the importance of culture in the organization. There's a lot of chief people officers that may be more mechanical in sort of like hiring business practices that we need to fire them, documents to sign, more operational. People that really understand it all starts with culture. An employee experience that your employees, your most valuable asset, treat them as such, you know, like create an amazing place for them to work. Focus on values. The smartest, best people in the world, they want to feel like they're part of something bigger than themselves. I look for missionary as opposed to mercenary people that aren't there for the money. They're there for the mission. So what is the mission? What are the values? What do you stand for? And is this company prepared to live the values like no other company? That's how you get the best people. And so some chief people officer that really gets that.

AI assessment note: “I just think people that understand the importance of culture in the organization.”

Q Do you see commonalities in the best chief people officers you've worked with, you've seen in investments, Across the board, are there commonalities in what makes the best and what people should look for in their first CPO? What do you look for when you meet candidates?

A I just think people that understand the importance of culture in the organization. There's a lot of chief people officers that may be more mechanical in sort of like hiring business practices that we need to fire them, documents to sign, more operational. People that really understand it all starts with culture. An employee experience that your employees, your most valuable asset, treat them as such, you know, like create an amazing place for them to work. Focus on values. The smartest, best people in the world, they want to feel like they're part of something bigger than themselves. I look for missionary as opposed to mercenary people that aren't there for the money. They're there for the mission. So what is the mission? What are the values? What do you stand for? And is this company prepared to live the values like no other company? That's how you get the best people. And so some chief people officer that really gets that.

AI assessment note: “I just think people that understand the importance of culture in the organization.”

Q and he actually said, you know, the process in terms of the sale of Jet was, I mean, it was great, but it was rocky, and it wasn't always so guaranteed, and it was up and down. I'm being British, uh, he was a little bit more direct. But he asked, what were some of your biggest lessons or takeaways for From that process. And how did it impact you?

A Everything I'm telling you here about getting the values right, creating the culture, hiring the very best people in the world that knew e-commerce. I think we had built and had some of the best people in the world. And when Walmart made the acquisition, that was a, probably the single biggest reason why they were interested in spending three billion dollars for Jet. It certainly wasn't the market penetration, the customers that they were buying. They were buying the team and the know-how and the Technology. And so there's always an orb there. I find when you invest in people and you invest in assets that are hard for strategies to replicate. So technology, technology and people, if you're spending money in other areas, it's not going to be value as much. It gets more risky. So you better make sure, like if you're investing in, in marketing early on that you have such an incredible CAC cost to acquire a customer to LTV lifetime value of a customer relationship. That you know, okay, this is working, and more fuel, we can get it because it's working, and we're going to create a big company. But before you prove that CAC LTV, you want to invest in people and technology, and I think a lot of startups, they do invest in technology, and that's why many times it's okay, but few invest in the best talent in the world because they don't have the capital, and that's what the VCP fund is …

AI assessment note: “when Walmart made the acquisition, that was a, probably the single biggest reason”

Q controlling V, uh, the vision itself, I I'm totally with you. I love the unwavering vision, the persistent entrepreneur. There is sometimes a time when you're like, you know what, Mark, The world is telling us something here and the vision may be great, but the market timing is, and we need to change course. How do you think about when to stick versus when to remain with the vision?

A The strategy can change. So how you get there, the vision shouldn't change. If you do the right amount of work upfront, and I mean, a hundred plus hours crafting, thinking about the vision, talking to people, don't be afraid to share your vision because it's like a piece of clay. You got to keep molding it and molding it. You'll know, okay, the timing's right. Massive, Tam, and you'll just have a level of conviction after talking to enough people that there's something massive here. Now, the strategy, how you get there, lots of different ways. You might have to pivot. You might have to, but I can't think of a situation where you'd spend all that time on the vision and then sort of get it wrong because it's so big and you've talked to enough people and you know enough about the world to know, like, that's where the world's going. You know, it's, it's, it's hard to imagine. I guess it could happen, but Maybe it happens if you haven't done enough work on it. I don't think people spend enough time on the vision. They'll say, like, if you ask somebody, what is your vision? 10 to 15 years, where do you want to be? It's rare that somebody will be able to, like, recite a, like, really tight three to five sentences of exactly what they want to be in 10 years from now. Most people just get so caught up in kind of the day-to-day, and they have a vague thing about where they want to go, bu…

AI assessment note: “The strategy can change. So how you get there, the vision shouldn't change.”

Q and he actually said, you know, the process in terms of the sale of Jet was, I mean, it was great, but it was rocky, and it wasn't always so guaranteed, and it was up and down. I'm being British, uh, he was a little bit more direct. But he asked, what were some of your biggest lessons or takeaways for From that process. And how did it impact you?

A Everything I'm telling you here about getting the values right, creating the culture, hiring the very best people in the world that knew e-commerce. I think we had built and had some of the best people in the world. And when Walmart made the acquisition, that was a, probably the single biggest reason why they were interested in spending three billion dollars for Jet. It certainly wasn't the market penetration, the customers that they were buying. They were buying the team and the know-how and the Technology. And so there's always an orb there. I find when you invest in people and you invest in assets that are hard for strategies to replicate. So technology, technology and people, if you're spending money in other areas, it's not going to be value as much. It gets more risky. So you better make sure, like if you're investing in, in marketing early on that you have such an incredible CAC cost to acquire a customer to LTV lifetime value of a customer relationship. That you know, okay, this is working, and more fuel, we can get it because it's working, and we're going to create a big company. But before you prove that CAC LTV, you want to invest in people and technology, and I think a lot of startups, they do invest in technology, and that's why many times it's okay, but few invest in the best talent in the world because they don't have the capital, and that's what the VCP fund is …

AI assessment note: “when you invest in people and you invest in assets that are hard for strategies to replicate”

Q to be radically transparent, and then I was like, actually, you could have just had a fight with your wife, your best friend, whatever, some, there might be a family illness, whatever's happening, and actually, there's a time and a place to have that transparent feedback. Would you say, when you have a problem, say it, or do you have to pick and choose your time? I'm just using this.

A Yeah, when I say transparent, too, by the way, some people do Interpret that as this radical transparency, like tell somebody that they suck. That's not what I'm talking about, and I think there are people that interpret it that way. I'm talking about transparent yourself sharing information, so I'm really talking about more sharing information, being transparent with your feelings, transparent with information, and not being secretive, not, you know, basically just being open. On the flip side, in terms of the being radically transparent in fights and things like that, I actually take a Different approach. I'm more about empathy in that situation, really just listening, trying to see the other person's point of view. I'm a big fan of Myers-Briggs personality test. There's 16 personalities. I try and know the personality type of all my friends, family, and anyone, colleagues, because I think understanding the personality type is like kind of the first, you know, the beginning of understanding and being empathetic because you Get to know a personality type, and you understand why they may react a certain way, or be a certain way, do a certain thing, and it's more, you can understand it better, because there's certain personality types that you're just going to clash with. It's just, that's the way it works, and knowing that it's the personality type and not the person is really …

AI assessment note: “I'm more about empathy in that situation, really just listening”

Q Can I ask a weird one? What are you worried about with the new VCP fund?

A This may sound like a cop-out, but I don't really worry about much, like, at all. I don't worry about stuff that's going to happen in the future, and I don't dwell on the past. I spend every minute focused on trying to make things happen in the now. I don't really spend any time worrying. If I've, if I got the vision right, I spend a lot of time on the vision. I feel convicted on the vision and raise capital and hire the very best people. I kind of just let things, I don't, there's nothing to worry about. It'll be what it'll be. All I can do is, is control VC and P. So I don't worry about that stuff.

AI assessment note: “This may sound like a cop-out, but I don't really worry about much”

Q to be radically transparent, and then I was like, actually, you could have just had a fight with your wife, your best friend, whatever, some, there might be a family illness, whatever's happening, and actually, there's a time and a place to have that transparent feedback. Would you say, when you have a problem, say it, or do you have to pick and choose your time? I'm just using this.

A Yeah, when I say transparent, too, by the way, some people do Interpret that as this radical transparency, like tell somebody that they suck. That's not what I'm talking about, and I think there are people that interpret it that way. I'm talking about transparent yourself sharing information, so I'm really talking about more sharing information, being transparent with your feelings, transparent with information, and not being secretive, not, you know, basically just being open. On the flip side, in terms of the being radically transparent in fights and things like that, I actually take a Different approach. I'm more about empathy in that situation, really just listening, trying to see the other person's point of view. I'm a big fan of Myers-Briggs personality test. There's 16 personalities. I try and know the personality type of all my friends, family, and anyone, colleagues, because I think understanding the personality type is like kind of the first, you know, the beginning of understanding and being empathetic because you Get to know a personality type, and you understand why they may react a certain way, or be a certain way, do a certain thing, and it's more, you can understand it better, because there's certain personality types that you're just going to clash with. It's just, that's the way it works, and knowing that it's the personality type and not the person is really …

AI assessment note: “in terms of the being radically transparent in fights and things like that, I actually take a Different approach.”