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Summer Break: How They Broke Precedent - The Origin Stories · Breaking Precedent

• Origin Story Clip 1 - Stacy Brown-Philpot ​[00:00:00] StacyLeahRaw: When you look back at Young Stacey in Detroit, do you see traces of the [00:00:10] CEO you became, or did, or did that ambition kind of sneak up on you later? What do you think? StacyGuestRaw: You know, my brother would say that it was always there. 'cause I was the [00:00:20] CFO of the paper route. He, we had a paper route, you know, he, it was his paper route and he, StacyGuestRaw: you know, wanted me to help him. So I helped him with the paper route. And so I [00:00:30] would collect all the money, add up all the money and figure out how much we got to keep, depending on how much we collected every week. StacyGuestRaw: And so there was that leadership role that happened in that, [00:00:40] in that capacity. And then, um, 'cause people always ask me, do you, did you wanna be a CEO? And I'm like, I don't think I did. Even when I joined TaskRabbit, like, I joined 'cause I wanted to work with you. [00:00:50] That was it. It wasn't like to be the CEO of the company, but I remember being in high school and when I was a majorette, they were like, Stacy, we want you to, you [00:01:00] know. StacyGuestRaw: Run the team. And I was like, me, why do you want me to run? And that was good. But I don't think I was the best twirler. I mean, there were definitely twirlers on the team who could [00:01:10] do like triple hole turns and I could do a double hole turn. Like there was definitely skills that I was still trying to master at this time. StacyGuestRaw: And they're like, well, you're really organized and so we [00:01:20] think that you could, and so then I was the captain of the team. So there was, there were moments where I stepped into these leadership roles, not because I was gunning for it, but because [00:01:30] I just obviously demonstrated some natural abilities. Clip 2 - Samara Hernandez Samara: Just one more semester. Just one more. Leah: I mean, they must have been so proud too, to [00:01:40] see you there studying. Samara: They were incredibly proud, the fact that they listened and they said, just one more. Just one more. Just one more. Leah: Yeah. Wow. Samara: I mean, [00:01:50] I struggled. There was one point where I remember I had $5 left to my name and I had like two weeks left and it was like going a free [00:02:00] event so that I can get my free pizza. Samara: And of course I didn't wanna tell my parents because I knew they didn't have a lot. However, I was a part of this first Latina sorority in the [00:02:10] country where we. All related to a lot of our cultural nuances, and three of them were engineers. And so we would study together. I was part of the Society of Hispanic [00:02:20] Professional Engineers where we would have that cultural connection, but also people would help me navigate, you know, if I didn't have my financial aid ran out, where [00:02:30] other options I can have, and I went to two office hours a day. Samara: I remember like I would go to learn the material and then I would stay to teach others so that I knew I learned it. [00:02:40] So. These communities are what helped me stay connected and helped me realize, okay, I am not alone. Clip 3 - D-Nice D Nice: You know what's funny, um, is that growing up [00:02:50] you never realize you're poor when you're like living in the moment because everything was just. Great. You know, I was a kid. I had these, these bright eyes and I, I wanted to see the [00:03:00] world, you know, and I, I was lucky enough to start making music at a, at a pretty young age, but I didn't realize that we didn't have much. D Nice: But what we did have was like a lot of love. You know, we lived in a [00:03:10] tenement apartment, uh, in the Bronx. Um, those, that was during my formative years. Um, you know, I, I slept in the living room with my great-grandmother on one [00:03:20] sofa. I was on the other, it was my cousin's apartment. It was probably like, you know, it looked larger than it was back in the day, but it was pretty much like a four to 500 square foot apartment.[00:03:30] D Nice: And, you know, it was love. We had food every day, and if we didn't have money that, you know, the, the bodega, the corner store bodega guys were good enough or kind enough to, you [00:03:40] know, extend us a little bit of credit to get some food and, and, um, you know, um, but it was still like this great time. You know, that's what I remember, you know, whenever I would [00:03:50] visit my other family, you know, who they, you know, may have been doing a little bit better. D Nice: It just always felt like love, you know? Like I didn't feel like I lacked anything. What I learned about [00:04:00] that experience though, you know, growing up without, you know, I mean, both of my parents are still alive. I just didn't have the relationship with my father. Uh, my mom was around, but she was a young [00:04:10] mother. D Nice: So that's why, how I ended up in, you know, staying with my great-grandmother or my cousins or my aunts, um, it was really because of that. Um, but what I learned from that [00:04:20] was nothing stopped my curiosity because I didn't have someone to tell me, Hey, don't climb that tree. You're gonna hurt yourself. [00:04:30] I had to do it and I had to learn by falling. D Nice: Yeah. And you know, so I've kind of lived my life that way. And as a parent, I still kind of extend that to my own kids, you [00:04:40] know, where I'm not a helicopter parent. I want them to explore. I want them to find. What's, what's gonna make them happy, you know, how are they gonna have like, true enjoyment in life, [00:04:50] you know, and, Clip 4 - Stacy Brown-Philpot StacyGuestRaw: Yeah, well it taught me everything. I mean, we, it was my great-grandmother, my grandmother, my mom and me in that house. And then there were three [00:05:00] other people, my men in the house, my brother, my grandfather, and and my uncle. So there's seven people in the house total. And, but these women ran the house and, you [00:05:10] know, talk about the matriarch. StacyGuestRaw: Really ruling it was, it was that my grandmother always taught us to look out for other people and she [00:05:20] would send food next door, either way. Depending on who needed an extra plate or down the street, or if somebody was sick, we would take something and pick them up from [00:05:30] something from the store. And we didn't have a lot. StacyGuestRaw: So she taught us like, even though you don't have much, you have to give to other people. And that was so important. She [00:05:40] taught us about standing up for yourself when you know there's always gonna be situations people don't wanna work with you, interact with you like you do [00:05:50] anything. And I remember being pushed outside the door to like stand up for myself when these girls didn't like me. StacyGuestRaw: I was walking home from the bus stop and they just kept picking on me. And she was [00:06:00] like, they're gonna keep picking on you until you tell, until you make it stop. And I was like, oh, I have to make it stop. StacyGuestRaw: Oh, go out there and, and we don't fight anymore. But [00:06:10] it was a fight. It was a fight. I had to, I had to fight for myself StacyGuestRaw: and that was scary and hard, StacyLeahRaw: Mm-hmm. StacyGuestRaw: but it taught me that [00:06:20] there's. StacyGuestRaw: Even in a world where there's people who can help you out, sometimes you have to be the person to end something. And it didn't happen anymore [00:06:30] after that. StacyGuestRaw: Yeah. StacyLeahRaw: Yeah. fascinating. I mean, I think you and I have talked a lot about this too. Like there are always people that are [00:06:40] just not gonna vibe with you, right? StacyGuestRaw: Mm-hmm. StacyLeahRaw: not gonna be your StacyGuestRaw: Mm-hmm. StacyLeahRaw: They're, not gonna like you. I, like you and I have talked about this, and that's such an interesting [00:06:50] story growing up. How did that lesson translate into business, into boardrooms, particularly when you're the only women woman or the [00:07:00] only black person in that room? Like how, how did that apply? StacyGuestRaw: You know, being the only one of something wasn't about like, or [00:07:10] not like, but it that helped me deal with the discomfort. StacyLeahRaw: Mm. StacyGuestRaw: When you walk into a room and you're not sure how people [00:07:20] feel about you, you actually learn to care less about what they think just based on appearances, your color of your skin, the [00:07:30] gender, and more about how they respond to your perspective. StacyGuestRaw: And so I showed up at the HP board meeting. I was the [00:07:40] youngest person to join that board. I had a business being there 'cause they invited me to join the board. But, and a deep down in my little soul, I'm like, am I supposed to be here? [00:07:50] I have earned this seat at the table. StacyGuestRaw: And it just taught me, you know what? StacyGuestRaw: You have something to say Stacey. And even if people don't like it, StacyLeahRaw: Mm-hmm.[00:08:00] StacyGuestRaw: say it. And so I've become the person who says the thing that people maybe don't wanna hear or it's hard to hear, but it [00:08:10] can move a conversation forward. It can move a decision forward. You and I had lots of moments where. StacyGuestRaw: We would debate stuff and discuss things at TaskRabbit where we just, I had [00:08:20] to move something forward StacyGuestRaw: and look back and be happy StacyGuestRaw: that we did. Clip 5 - Stacy Brown-Philpot StacyLeahRaw: When you think about that [00:08:30] journey from Detroit classrooms to Penn to Stanford, you look back, what do you wish educators understood about spotting [00:08:40] potential in StacyGuestRaw: Hmm. StacyLeahRaw: you? StacyGuestRaw: Yeah. I wish they understood. Don't [00:08:50] shortchange me. StacyGuestRaw: Right. So sometimes when you look at me. StacyLeahRaw: Mm-hmm. StacyGuestRaw: Like that [00:09:00] counselor who was like, oh, I don't know. You know, it's really hard to get in. And I was smart. I was straight a student. I was, you know, second in the class salutatorian. Like, I, you know,[00:09:10] StacyGuestRaw: and yet there was this sort of, StacyLeahRaw: yeah. StacyGuestRaw: and yet, StacyGuestRaw: so we want to be pushed.[00:09:20] StacyGuestRaw: We can do it, we can make it. Um, it is okay. And yes, we should take care of our mental health and all the things that [00:09:30] happened after we became adults. The, the care about mental health. We were kids. We didn't get that part. Leah did we? StacyGuestRaw: Oops. StacyLeahRaw: That was not a thing when we StacyGuestRaw: But [00:09:40] we wanna be pushed StacyGuestRaw: and we wanna learn and we wanna make an effort. StacyGuestRaw: And so don't give up on us. StacyGuestRaw: Don't think just because we came from a difficult [00:09:50] environment or you know, our parents got divorced when we were young or. We don't always have the food that we need to eat, that we can't make it, we we can.[00:10:00] StacyLeahRaw: Did that, was there some pieces of that too that almost motivated you more in some way to make it StacyGuestRaw: It was [00:10:10] motivating and it also felt like a responsibility at some point too, StacyGuestRaw: where there was a motivation to prove people wrong. And so [00:10:20] some people are motivated, oh, I wanna prove this person wrong. They think I can't do it because of my circumstances, but I was taught to never let your circumstances define you. StacyGuestRaw: They may be what [00:10:30] they are, but they should never define who you become. StacyGuestRaw: And so living that way for me was always moving forward. But then I felt this [00:10:40] responsibility to do well and do good for the people who couldn't handle their circumstances. Who. Didn't have [00:10:50] the opportunities that were given to me and didn't have the person push them through a challenging time when they really needed it, and I did. StacyGuestRaw: And so I had [00:11:00] to carry a load of giving back and proving that I could accomplish something with all the opportunities that I had. Clip 6 - Samara Hernandez Samara: He [00:11:10] grew up as an orphan. And so he had literally three outfits his whole life. Three outfits. Leah: Wow. Samara: Three shirts, three pants, one pair of shoes. [00:11:20] And we also grew up with, not a lot. And during the beginning of the school year, I would choose three outfits for the entire school year. Wow. And three outfits for the summer, and that's all we got. Samara: That [00:11:30] story basically is kind of how my whole life early on was limited resources, limited clothes, limited [00:11:40] money, limited. Everything. And even my first chalkboard was from a garage sale my mom bought for me and only half of it worked. But what I [00:11:50] used it for was for math. My sister would teach me math skills that she learned as she was three years older than me and we would use half of the chalkboard and do math problems.[00:12:00] Samara: And we were home a lot by ourselves 'cause my parents were always working and we didn't have a babysitter. So that's where I got my early start in excitement for math. That's where I got, [00:12:10] I guess, the homework. I didn't have a tutor. I didn't have, you know, somebody telling me to do extra workbooks. I just did it because we had it available to us. Samara: And [00:12:20] so whether it's clothes or whether it's chalkboard, having this limited resources, but doing the best with what you have Clip 7 - Samara Hernandez Samara: I was a part of this first Latina sorority [00:12:30] in the country where we. All related to a lot of our cultural nuances, and three of them were engineers. And so we would study together. I was part of the Society of [00:12:40] Hispanic Professional Engineers where we would have that cultural connection, but also people would help me navigate, you know, if I didn't have my financial aid ran out, [00:12:50] where other options I can have, and I went to two office hours a day. Samara: I remember like I would go to learn the material and then I would stay to teach others so that I knew I [00:13:00] learned it. So. These communities are what helped me stay connected and helped me realize, okay, I am not alone. And that's what ultimately led me [00:13:10] to graduate. And frankly, I still have nightmares that I didn't graduate 20 years later. Leah: Really. I mean, it sounds like it was incredibly intense. It probably built a lot of [00:13:20] resilience, but you were able to find that community of people that were there and were your family when you were studying. Yeah, Samara: totally. Yeah. And I [00:13:30] didn't go into pure engineering when I graduated, however, Leah: okay. Samara: There's an engineering mindset that it teaches you. Samara: Mm-hmm. Or one, it's gives you street cred, right? Because everyone knows how [00:13:40] difficult it is. And a recruiter, he was like, you can't fake an engineering degree. And you know he was right. But two, it teaches you how to. Solve a [00:13:50] problem that you've never seen before. So I don't know if it's just the craziness of engineer of Michigan or what, but we would do all these homework assignments. Samara: We would learn all the things in class. As you probably know [00:14:00] this, you get to the exam, you're like, what the heck? Leah: Right? Samara: You've never seen this type of problem. You've never, like, where do you even start? So it teaches you how [00:14:10] to solve a problem, break it apart, put it back together in different ways. Take one theorem and another theorem and put it together. Samara: And so it [00:14:20] really teaches you how to think about something, how to solve things in a very different way. And I still use that. Leah: Yeah. Samara: Now in working in finance. And so it was [00:14:30] such a great thing for me to do. I really appreciated my time there. I still have nightmares and I, you know, I'm glad it's done, but I learned a lot. Leah: [00:14:40] Sounds like it was a lot of life skills. So you did graduate. What did you go on to do? Did you go straight to Goldman after that? What was next? Samara: Yeah, I was on Wall Street, so I [00:14:50] just told this story recently. A group of friends of mine, we went around the room, they were asking us how you got into finance, Clip 8 - D-Nice D Nice: Oh, absolutely. Um, I, I grew up, you know, with [00:15:00] my career, the beginnings of my career was obviously hip hop and, and I started out in a group called Boogie Down Productions with a DJ by the name of Scott Rock. And, um, you know, a legendary [00:15:10] mc named KRS one. D Nice: And we started the group, well, they started the group and then they brought me into it. You know, they were a little bit, you know, seven or eight years older than I was, but I was like the, the [00:15:20] kid, the young kid who was always curious. So I did a little bit of everything. I made beats. I learned how to dj, I learned how to write lyrics. D Nice: You know, I used to sit in that apartment, um, in the [00:15:30] Bronx, and I would be for a little bit of privacy, I would, I would spend time sitting on the bathroom floor. And, you know, like most kids my age, back then, I was kind of [00:15:40] obsessed with like New Edition and, you know, and I wanted to be a songwriter because I couldn't sing. D Nice: Little did I know, like I was going to end up becoming a songwriter in my own way, you know? [00:15:50] Um, through hip hop. Um, hip hop was still kind of in its infancy. So, you know, there wasn't a lot of money to be made unless you were run DMC or LL Cool J who was [00:16:00] selling millions of records. But when you're like a part of a group and you're young and you know. D Nice: Fresh on the scene. It was, we didn't make a lot of money, but we just had these, we [00:16:10] had these big ideas and we had a big following and, and you know, like, and, but that was like the beauty of, of the culture then, because we weren't [00:16:20] doing it for, for money, you know? Yeah. You know, now as an adult, yes, I do want to be compensated for what I do. Leah: Right. But D Nice: then it was, it was about the [00:16:30] love, the love of music and the love mm-hmm. Of being able to see people all over, you know, like my first time being on an airplane, we were going to Rochester, New [00:16:40] York to do a show, and we were, we were just young. And I had never seen, uh, that, I think that was the, that was a pivotal moment for me because when it's [00:16:50] your first time being above the clouds and like, and your, your imagination is just flowing, it changed everything about me. D Nice: Like I wanted more of it, you know, I wanted to, [00:17:00] I was like. I just wanted more, I wanted to travel more. I wanted to have these experiences and especially since, you know, I, I was never really into much television, but the show that I [00:17:10] always watched every Sunday was, um, Robin Leach, the Lifestyles of the Rich and Famous. Clip 9 - D-Nice D Nice: It's about, it should be about growth, you know? And, um, without [00:17:20] judging anyone, I know that growth was, for me, was always important. Like, I, I could have continued trying to make hip hop records, you know, I could have done [00:17:30] that. I could have been submitting demos, but at 22 years old, I was considered old school and that was, um. D Nice: That was an important time for [00:17:40] me because I couldn't understand like, how could you be old school at 22 years old? Leah: Right. You D Nice: know, and, and record companies didn't wanna work with me. And yeah, I wasn't a part of [00:17:50] anyone's collective. I was just this one guy, you know, trying to figure out how to still be creative and, and I ended up losing everything and it was the best thing that happened [00:18:00] to me because it forced me to, to find ways to be creative in other ways, which is how I got into photography, which is how I [00:18:10] got into, you know, web development. D Nice: Like I didn't, I taught myself, you know, c plus plus and PHP and Flash, and HTML. I did all [00:18:20] of that because I, I, I would just go to, I couldn't afford to go to school, so I, I would just go and buy books and then I would download, you know, code and like resource files and [00:18:30] learn how and what these things meant. D Nice: Yeah. And then it changed my life though, you know? Yeah. It, it, it brought me to, you know, doing sites for everyone from an at and t or I was [00:18:40] doing movie sites and, you know, from, and I was doing music sites for Alicia Keys and Annie Lennox and Boys Men and like Luther and Violator [00:18:50] and, you know, I had deals with all of the record companies from Arista and Motown and Sony, but I was a rap kid, you know, who was just trying to find ways to still stay [00:19:00] creative and, you know, by the grace of God I was able to do so. Clip 10 - D-Nice D Nice: I don't know why, but I would always take these things apart because I wanted to know how they worked. Yes. No, that is [00:19:10] the truth. Wow. You know? Wow. I mean, even down to when I had nothing but time on my hands and someone had given me like a Mac performer, it was like a [00:19:20] 6,400 performer, and instead of just using the Mac, I took the Mac apart because I was trying to, my God understand. D Nice: It's amazing. I was using, like, I was [00:19:30] using, I, I was just downloading and just trying to understand. Yeah. Yeah. And then I would go into, we didn't really, didn't have too many, um, it wasn't like a lot of, I don't even remember if there were like websites, [00:19:40] but I, but there were a lot of bulletin boards that people would, would go into and, and CompuServe and I would try, I was like trying to build bulletin boards. D Nice: I was just trying to, uh, [00:19:50] anything that kept me creative when I was at home, when I couldn't, I didn't have the fresh clothes and I didn't have any records out. So I could be [00:20:00] whoever I wanted to be from behind the computer. And that, that is actually probably why COVID when you fast forward, I know we haven't gotten to that part [00:20:10] yet, but when you fast forward to what happened in 2020, it was like this culmination of like, everything that I had done in my entire life. D Nice: I was a graphics guy, so I [00:20:20] made a flyer for, for, for a virtual web, for a virtual party. I'm a tech dude, so I knew how to make my sound sound good, you know, I knew all of these things, you know, [00:20:30] and, and um, and it was just like everything just kind of came together at once. I was always like. In front of this computer, in front of a camera. D Nice: I'm [00:20:40] extremely comfortable just being here alone. But that was because of my days when, when, when there was CompuServe and there was a OL and I would go into the chat room and I would [00:20:50] be, I wanted, I wanted like famous, so addicting that I wanted to be recognized. And I was like, Hey, I'm Denic. You know, I wanted to be recognized [00:21:00] in these, in these chat rooms, which is so crazy. D Nice: But when you fast forward two, three decades later, it because of that, it, it all changed my [00:21:10] life and it, it was, um, yeah man, I have no regrets. Leah: Yeah, it's really amazing. Clip 11 - Shiza Shahid Leah: Well, I'm excited to dive in. So, you know, when I thought about the concept for [00:21:20] Breaking Precedent, I thought, who are those people that I know that are doing incredibly sort of game changing, world shifting [00:21:30] things? And so I want to start out by just asking you sort of the. The highest level question I can, which is when you think [00:21:40] about breaking precedents, setting precedents, new precedents, or maintaining and upholding precedents, how do you see yourself fit into [00:21:50] those different Leah: buckets? Shiza: Well, I think of my family. I think of the women that came before me who [00:22:00] were not given the opportunity to pursue their dreams, to fulfill their potential. I was born in a [00:22:10] fairly traditional family in Pakistan, but my mother was really a trailblazer who fought fought for her children to have the very [00:22:20] best education. Shiza: possible and really kind of set us free to do whatever it was that we dreamt of. And so I got to break [00:22:30] precedent by being a young social activist in my community, by being, uh, 18 years old and getting a scholarship to [00:22:40] study at Stanford university and move halfway across the world on my own by becoming an entrepreneur. Shiza: But I also think as [00:22:50] I came to the United States and became a part of this society, I was breaking precedence here because I [00:23:00] was not what your typical entrepreneur looked like or the background that your typical venture funded startup founder may come from. [00:23:10] I wasn't that. I didn't fit that mold. And I was building businesses or. Shiza: Nonprofits that tried to marry social return [00:23:20] with positive good, and that in itself was breaking a precedent. And so I think for me, I've always broken precedents because in part, I had no [00:23:30] choice, and in part I, I didn't know what the precedents were. They didn't exist for Shiza: me Shiza: and so I was just kind of molding Shiza: my own path. Leah: Yeah, that's pretty amazing. [00:23:40] Leah: That is, that's incredible. And I want to dig into all of those different precedents that you've broken and that you've set. Um, but let's talk a little bit more [00:23:50] about what it was like growing up in Pakistan. What was your childhood like? You mentioned the importance of education to your family. Leah: You know, where did that come from and, [00:24:00] and what was it like? Shiza: I think my childhood was a mix of deep meaning and deep emptiness, and it kind of [00:24:10] swung between the two. My mother was born into a fairly traditional family, was the oldest of four sisters, didn't get [00:24:20] to pursue higher education, build a career, choose the man she would marry, although my father's wonderful and they're very happy. Shiza: So sometimes arranged marriage [00:24:30] actually works. Um, that's neither here nor there. Um, And I think she just felt this sense of, of, um, [00:24:40] lost her anger and wanted to make sure that her daughters had the very best education. And so she fought for that and my father supported [00:24:50] her and they went out and built their own lives on their own terms. Leah: Wow. And is just you and your sister? Is it the two of you? Shiza: and I have a brother Leah: Oh, you have a brother, too. [00:25:00] Okay. Shiza: I'm, I'm the youngest by eight years. So I was raised somewhere between being a youngest and an only, because there was such a Shiza: big age gap Leah: Mm hmm. Mm [00:25:10] hmm. Shiza: By the time I was growing up, my siblings were out of the house and I was kind of growing up alone in some senses. Shiza: Cause my, my parents had sort [00:25:20] of, they'd set really strict boundaries around themselves, um, from society, from any, you know, extended family that may disagree [00:25:30] with the choices they were making around their lives, around their children's lives. Leah: hmm. Shiza: And I was growing up in Of course, the day I have the [00:25:40] podcast is the day for some reason I have a tickle in my throat. Leah: And it's okay, because we'll edit it all out. Don't worry about it. Shiza: I'll just process my voice, make it sound like, uh, Beyonce. [00:25:50] Um, Leah: Exactly. Shiza: I was growing up in the capital city of Pakistan, Islamabad, in the post 9/11 world, which was [00:26:00] one of the most turbulent times in my country's history. And Shiza: we've our, more than our fair share. And that meant. suicide bombings, terrorist [00:26:10] attacks, closer and closer to my hometown. Shiza: Whereas in the first decade of my life, really, it had been fairly peaceful. And [00:26:20] so as my society was changing, I was trying to make sense of the world around me. And I was often kind of filled with this sense of, of [00:26:30] righteous anger. When There was a military dictatorship when rule of law was undermined, when women were [00:26:40] denied their right to work, when girls were denied their right to go and pursue their dreams. Shiza: I would go out and I would volunteer. And [00:26:50] I think from a young age, I sort of started to understand the power that I had to show up to make a difference and how that filled me with a [00:27:00] deep sense of meaning. And so a lot of my childhood was that. It was volunteering. In disaster relief, microfinance, a lot of work with women and [00:27:10] girls organizing. Shiza: And it was juxtaposed by this sense of emptiness because on the other side of it, I think there really wasn't [00:27:20] that much opportunity for girls, for young women. Um, the economy was weak. The rule of law was weak. There were very few protections against [00:27:30] sexual harassment. Um, and so you didn't have this. Shiza: fertile landscape to build that find in places like Silicon Valley, Los [00:27:40] Angeles, New York, Leah: where Shiza: you can go out and start something with a lot more ease than in Islamabad, [00:27:50] Pakistan. Leah: Right. Right. And were your parents sort of helping drive that philosophy? I mean, I read somewhere your, [00:28:00] your dad would take you to volunteer at, you know, relief camps. And, and what, what sort of role and influence did they play on your, [00:28:10] your sort of drive and motivation? Shiza: You know, I think the bad news for parents is I think it's really hard to [00:28:20] steer. Your children so directly. My parents didn't do that. I chose to do the work. However, they [00:28:30] they allowed me to do it. And when them, when I really kind of went over my head, they were there. The difference. I joke that they [00:28:40] practiced benevolent neglect. Shiza: I was the youngest child. They'd had to. They turned out okay. Leah: right, Shiza: fine. And so they kind of let me be, [00:28:50] and I found my way to these things that I was passionate about. But yes, my father would, would drive me to, you know, the earthquake relief camp. And many [00:29:00] of my, my friends parents wouldn't allow them to go because they didn't think it safe. Shiza: And when I'd organize something and I needed someone there to help, they would be [00:29:10] there. And, and so I think that sense of you go do this, we're not going to tell you to do it. We're sort of going to tell you not to do it because it's [00:29:20] not safe, but we're not to call you out when we find out that you did it anyway. Shiza: And if you really need us, we're here. That was really, I think what shaped my ability [00:29:30] to, to feel empowered. Leah: mm hmm, Shiza: And, uh, and yeah, now, now that, you know, my, my parents [00:29:40] now run an orphanage and they're very socially, um, they've always had a deep sense of giving back and service, but it was, it didn't push me into it. Shiza: And, um, [00:29:50] I think often what parents do here, however, is they push their children out of it, right? So, you know, if you think about the first time your toddler [00:30:00] sees someone who's unhoused and is distressed by seeing someone on the street who is distressed Shiza: and of immediately try and comfort them and say, don't worry, they're [00:30:10] okay. Clip 12 - Shiza Shahid Shiza: You you know, walk 10 minutes from my neighborhood in L. A. and see tremendous poverty and social [00:30:20] challenges right next door. Leah: Right. Well, let's talk about that, that big move 7, 000 miles away. I mean, I grew up here in [00:30:30] the U. S. I grew up on the East Coast and Stanford was never, ever something that was on the My [00:30:40] radar as a kid growing up here in the states, and I'm so curious to hear how did this come about and you get the scholarship and [00:30:50] how amazing what an Incredible opportunity in a moment that really does kind of shift Your life trajectory. Leah: So how did it all happen?[00:31:00] Shiza: It was just in some ways I think how it was meant to happen. [00:31:10] Um, I had no desire to leave. Pakistan. I had no desire study in the United States. I was, there was this one liberal arts college in Pakistan where my sister [00:31:20] studied that I was very excited to go to. That was it. One, one school. There wasn't a second school that I could imagine going to for university. Shiza: And, and so I thought, well, I should [00:31:30] apply somewhere other than that school in case. I don't get in. Um, and I had, of course, heard of folks who had gotten [00:31:40] into places in the U. S. called Stanford and Brown and Harvard. And so being highly naive about how difficult it was and how [00:31:50] much, you know, the most privileged students and children in the world prepare themselves for an opportunity like this. Shiza: I googled top 10 [00:32:00] schools in the United States and to them. Um, had, I had good grades. Um, I had to do the [00:32:10] SATs because I had to do them even to get into that one school in Pakistan. And I, I well in those. And I, and And I think I just had something to [00:32:20] say because I had been doing work my entire life that was different from the, you know, violin lessons and [00:32:30] tennis classes that typically pad the college application of someone applying to Stanford and so. Shiza: Couldn't play an instrument, couldn't [00:32:40] play any sports. But I had done this work that I think probably stood out in my application, Leah: Wow, so you wrote about that work and you [00:32:50] kind of shared Your story of what you're passionate about there and you sent it to Stanford Shiza: I did, but I, you know, I, I, not because [00:33:00] anyone told me to. I don't think that read my essays. I don't think anyone ever counseled me on, uh, what, how you apply. I think it was just me being [00:33:10] me, Mm hmm. that was enough, and I was, um, I offered a handful of scholarships I couldn't afford to pay, and, uh, I chose Stanford. Shiza: And [00:33:20] that was it. Leah: Were your parents immediately on board with this decision? I mean, it's a big decision to move 7, 000 miles away.[00:33:30] Shiza: I think so. I think it was, you know, it was again, they, they didn't tell me to apply to the United States. Uh, didn't read my college essays, but [00:33:40] when it happened, they were like, okay. Congratulations. Leah: Congratulations. Let's get you packed up. Yeah. Wow. really [00:33:50] incredible. And so you arrive at Stanford and you get there and it's got to be just completely [00:34:00] different, um, than what you're used to. Did you have expectations on what it might be like when you arrived or a vision in your mind?[00:34:10] Shiza: So, I had, I was so passionate about this sense of wanting to make a difference in my [00:34:20] community and in the world. And to me in some ways, the scholarship felt like a confirmation that that was what I was [00:34:30] meant to do. As if the world was saying, okay, what you're, you're meant to do something that, that is helpful to others. Shiza: So here is, um, [00:34:40] you know, a little something to help you along the way. Um, so I think I was a very serious, Um, college student, [00:34:50] not so much about academics, but about how to take this opportunity and use it to further the work I was doing. Clip 13 - Bianca Gates Bianca: it was [00:35:00] awesome in my household. My parents are extraordinary people, um, ambitious people. They, they came to the United States with, you know, almost nothing. Um, my [00:35:10] mom was raised by her mother in a small village in Bolivia, Santa Cruz, Bolivia. She had two younger sisters. Her father left when she was six. Bianca: And um, yeah. [00:35:20] You know, she overcame a lot. She moved to the United States with my dad who was born and raised in Argentina. And she moved here right after getting married to him at 17, [00:35:30] um, and did not speak any English and worked at a cafeteria making salads because she couldn't speak the language. And was, you know, she led very, a very [00:35:40] grateful life. Bianca: She was happy that she had, was married, um, and like her mother who, you know, whose husband abandoned them, she was grateful that she was able to have children. [00:35:50] So I was raised in a household of a lot of love and gratitude and gratefulness for the opportunity of being here. But outside of my home, growing up in [00:36:00] Um, Orange County, California, it was a little bit of a different experience. Bianca: Um, I was financial, I was financial aid at a, at a private school [00:36:10] and, you know, the, the kids very much reminded me of that every day in some ways so did the school. my mom would come to pick me up and she would speak [00:36:20] only Spanish to me and the kids would bully me. I mean, back in the 80s growing in Orange County. Bianca: Being Latina was, was not considered cool. and [00:36:30] so they really, kids really bullied me, made me feel like an outsider. And I remember like once or twice a year at our school, if your parents [00:36:40] donated a certain amount of money to the school at a, at a, at an event, um, the kids would get free dress on a particular Friday. Bianca: And I was always the kid not in free [00:36:50] dress. And so it was like very obvious that I stood Leah: Oh. Bianca: And so it was, it was hard. Um, So I, I, I hated that feeling of not belonging. [00:37:00] I hated the feeling of trying to defend myself for, for who I was. I couldn't change, you know, who I was in my family origin. because of that, people treated me differently. Bianca: but I [00:37:10] also think that looking back on that experience, it has made me who I am today built a company. Um, anchored in lifting women and women supporting women. And, you know, [00:37:20] starting the first Lean in Circle with Sheryl Sandberg, like I have very much wanted to find a way to cultivate conversation and community amongst women in an effort to like lift [00:37:30] us up because I very much longed for that as a child outside of my home. Bianca: But inside my home, my parents are amazing. They're, they've just celebrated their 50th wedding Bianca: anniversary. gosh. [00:37:40] Wow. Bianca: have taught me so much about who I want to be both personally, um, and professionally. Clip 14 - Bismarck Lepe Bismarck: And they told me in third grade, they said, look, we don't really understand how the [00:37:50] educational system works here in the US, but you're going to go to college and we will work three jobs, four jobs, whatever's required. Bismarck: So you have tutors, books, [00:38:00] whatever you need to be successful. Leah: That's incredible. Bismarck: But it's up to you. You need to figure it out. Leah: Did you feel a lot of pressure and responsibility to live up to those [00:38:10] expectations growing up? Bismarck: Yeah, I could see how my parents sacrificed. My dad at one point, he would get up at two o'clock in the morning and go and deliver [00:38:20] newspapers and then come home or sometimes go straight to work and work either construction or eventually he started working maintenance at apartment [00:38:30] complexes. Bismarck: Get home from that job and schlep us to karate or piano or Somewhere then come home. And at six 30, [00:38:40] when I was in fifth grade, he was teaching electrical classes, air conditioning classes, and so he'd work until 10 or 11 o'clock at night. So he would sleep three [00:38:50] hours every night. And he did it just to make sure that they could provide for my brother and myself. Clip 15 - Aaron Holiday Aaron: And so. At different parts of my life and journey, I was blessed [00:39:00] to have people who could show me what the world could be if I thought about it differently. So take as an example when I left New Orleans to go to [00:39:10] Morehouse. I was the only kid in my high school class to leave the state. Leah: Wow. Aaron: We just grew up in a place where many people didn't leave home. Leah: Right. Aaron: So [00:39:20] my sister was already in Atlanta, and while I was applying to local schools, she was encouraging me to think differently, [00:39:30] to think about what would it be to exit. Aaron: and to go to a place where leaders have [00:39:40] been known to come from. And that's Morehouse. Leah: Yes. Aaron: So a lot of amazing people like Martin Luther King went to Morehouse. It was one of the biggest selling points for me. Leah: Right. It's Aaron: like, I want [00:39:50] to be a leader. I want to kind of change the paradigm of leadership. How I live and how my family will live in the future and let me go to a place where a person went [00:40:00] who totally changed the paradigm of our country from a civil rights standpoint. Leah: Yeah. Aaron: So I ended up at Morehouse as a first generation college student [00:40:10] and I was there a week early as a part of this program called SSS, Student Support Services. Leah: Okay. Aaron: And I met another person who is, again, [00:40:20] tangential to the new world that I was going into. And one of my hacks is spending time with people who understand the new world and listening and [00:40:30] embracing them instead of being resistant and thinking, I know it all. Clip 16 - Alejandra Campoverdi Alejandra: You know, first gen it's interesting because I call it, it is technically a memoir, but I kind of call it an anti [00:40:40] memoir because the reason why I wrote it is. Alejandra: I don't know, kind of wanting to deconstruct what would typically be in a memoir and not focus on [00:40:50] the bullet points of our resumes, not focus on the highlights or the graduation or the degrees and, and so on for a [00:41:00] reason. And that's because. You know, people think first gen is just, you know, maybe first gen college student, but I was looking at the emotional journey of being the first or the [00:41:10] only in all these different spaces. Alejandra: And in my life, and even before I got to school, there had been so many experiences of feeling, you know, isolated and [00:41:20] experience of, of trailblazing within my family. Right. And. Yeah. And. When I would go and speak to young people, because it was important to me even before the book, I [00:41:30] would go up there and they would introduce me with this bio. Alejandra: Like all of us, we Leah: Mm hmm. Alejandra: the accordion kind of closes into like a short little bio. And I just felt like it [00:41:40] was not telling the entire story. So when during, Shutdown in the pandemic. I got the book deal during that time and I thought, okay, well, if I'm going to have [00:41:50] an opportunity as a woman of color, and there are so few of us that have the opportunity to write books and publish them, what's the story that I'm going to tell because when I speak to these young [00:42:00] people, I recognize something, and I write this in the book, there was something in their eyes that I had too, which was, it's a complicated experience. Alejandra: It's a beautiful experience. It's, [00:42:10] it's a worthwhile one, but it also has mixed emotions. And so how do I tell the story in between the bullet points? How do I focus [00:42:20] on those spaces in between and kind of share the things that you maybe normally wouldn't share? Because I, I really. I do feel that [00:42:30] it's up to us to not kind of continue this myth of this linear glossy version of the American dream. Alejandra: You know, I know you yourself have had so [00:42:40] many firsts and are such a trailblazer. We could sit here, all of us, your listeners as well, and say, okay, well, I had it all figured out. I, I knew what I was [00:42:50] doing. And that doesn't serve anyone coming up behind us and, and frankly, at this point in my life and career, that's what I'm focused on. Clip 17 - Alejandra Campoverdi Leah: At the time, I didn't fully [00:43:00] grasp that for first and onlys, our efforts to recalibrate and survive in new spaces can often be misunderstood as leaving our friends, our culture, [00:43:10] or our families behind. We face dual rejection in our new environments and in our old ones for opposite reasons. Leah: What are those reasons? Can you [00:43:20] talk a little bit more about that? Uh huh, Alejandra: Well, it really struck me that I was hearing messaging, especially during these pivotal transition times, right? That was [00:43:30] criticisms for, criticism for opposite reasons, right? So you know, you get to, again, I'll make, use a college example because it's so easy [00:43:40] because it's such a stark difference. You know, you get into college, which in a lot of way for many of us is this social mobility jump into a new social class and, and especially if you're [00:43:50] a first generation college student again. Alejandra: And you're in this new space and the feeling is of being an outsider in many ways. But when you go home [00:44:00] and to your loved ones, the, the messaging I would get and from, you know, childhood friends as well would be, you've changed, you know, and especially as a [00:44:10] woman of color, oh, you're doing white things or you're being whitewashed language that you get. Alejandra: So when you're in the new spaces, the messaging you're getting is that [00:44:20] somehow you're, you're Or, you know, more ethnic or an outsider or an other, right? Whatever that other is. And then it's the opposite. And [00:44:30] so it's what, it's one of the reasons why there's so much cognizant cognitive dissonance during that time. Alejandra: You know, trying to find a way to keep both [00:44:40] experiences, kind of people happy, is really impossible. But I tried to for so long. And it wasn't just in those spaces in [00:44:50] college. You know, it is, you know, I write in the book, social mobility felt like a series of costume changes. Leah: Um. Alejandra: And whether it was the way that I kind of wore [00:45:00] my Latinidad on my sleeve in the 90s in LA, you know, in high school, and then the USC spaces where I always, I always share the fact that Legally [00:45:10] Blonde was filmed on campus when was Leah: I that. Alejandra: So just, to kind of paint the picture. And then, you know, again, Harvard looks so [00:45:20] different moving Boston, what that, what that kind of culture was to the White House and the idea as a woman and the femininity, how that expresses itself [00:45:30] or doesn't express itself or shouldn't express itself in your clothes to running for Congress and, and what that, and so it felt like the goalpost [00:45:40] keeps moving and it does keep moving. Alejandra: And if you train yourself to be trying to. find that perfect balance of making everyone [00:45:50] happy and belonging, and, and seeing belonging through that lens. I mean, you, you spend your entire life in a internal tug of war. Leah: Right. Alejandra: And it was easier for [00:46:00] me to see in retrospect. Cause I could see all these versions of myself. Alejandra: The inside was always the same, but the. The kind of [00:46:10] gloss and sheen and layers and paint and varnish all just kind of kept coming on and off and it was frankly exhausting not necessary. Clip 18 - Alejandra Campoverdi Alejandra: I [00:46:20] think as a first and only you are both a precedent breaker and a precedent setter because [00:46:30] you are So you, the whole idea of being a first and only by nature means you're breaking away from something, right? You're not, [00:46:40] you're not the first to do something. You're not a cycle breaker without there usually being a reason that you need to do that. Alejandra: So you can't get away from the precedent [00:46:50] breaker part to be a first and only, but at the same time, and that's why this experience is so complicated. You're juggling being a precedent setter. Because now you're navigating [00:47:00] these new spaces and you're like, okay, well what is this going to look like? And how do I even make my mark in a space that I don't understand? Alejandra: That whole kind of like paving the [00:47:10] path while you're walking on it. So I think that's one of the big complications is we kind of don't get the luxury of choosing, you know? We, [00:47:20] we have to be all things to all people. And that is a, that's a big part of the toll of this experience, but it's also a big part of the beauty. Alejandra: It's [00:47:30] also a big part of the, how meaningful it is because, you know, you're connected across not only [00:47:40] like generations, you know, but across experiences, you know, you're bringing the past into the present, but then you're taking the present and you're reshaping [00:47:50] it And, you know, it's not a boring experience. Alejandra: I don't have to tell you, you know, it's, it's not perfect, but boring. And you're never going to be someone [00:48:00] who wakes up and is like, um, oh God, I wish I had more like meaning in my life. Leah: Right. I wish my life was more dynamic. Alejandra: [00:48:10] Yeah, yeah. I don't have to shake things up. No, anything, it's the opposite. And that's, that's one of the reasons why, you know, I, I think there should be so much pride in this [00:48:20] experience. Alejandra: You know, I always say like, it's a, whether you believe in God or the universe or souls or whatever you believe, insert in here, right? [00:48:30] But it is a special soul that is born into a family line to change the direction. To change the cycles, to break the cycles, to [00:48:40] set a precedent, to break a precedent. That is a special, special soul. Alejandra: You should have pride because that's driven from something inside. That's not someone who told you to do [00:48:50] that. No one told you to go to this, just to create a startup. Like no one was there over your shoulder forcing you to work those [00:49:00] nights or to take those risks. Why is it that you do that, you know, and that's why going back to your original question about the intuition and the wisdom, that's why I trust it more than [00:49:10] anything, because that's a part of you that's innate, you know, it's, it's a strong, innate part that is wise. Alejandra: And. [00:49:20] It really is a compass for those of us that are breaking, setting X, Y, Z precedents. There's probably more things that you're doing with precedents as a person [00:49:30] Right. Alejandra: instead of always training ourselves towards imposter syndrome and the way that we are struggling [00:49:40] also, you know, also look at the pride and the contribution and the meaning of this experience. Clip 19 - Alejandra Campoverdi Alejandra: Well, my hope is [00:49:50] that each generation has a smoother go at it than the one before, right? And like we talked about earlier, the financial trauma is a really big piece [00:50:00] of why this is so hard for those that are trailblazers. Alejandra: So last year when I was running around and talking to a lot of young people, there was, it was always financial resources, [00:50:10] always kind of trying to meet that gap. And sometimes it was. food and the inability to travel home and see their family in the holidays. So I [00:50:20] self funded 10 grants for first gen students last year. Alejandra: And it was something that I felt really compelled to do. But when I put out the call, the [00:50:30] avalanche of applications that came in It just showed what that need was for hardship grants, right? Because there's tuition help and there's a lot of [00:50:40] wonderful organizations to support first gen students, but those small expenses, you know, you'd be surprised how a few hundred dollars can be the difference between someone [00:50:50] graduating. Alejandra: And it's really true. Wow. So over the past year, I decided to, launch a nonprofit, which is launching now. It's called the first gen [00:51:00] fund, and we've already been able to triple the amount of scholarship grants that we're giving out this year. And the whole idea again, is to provide [00:51:10] resources to meet this gap that is sometimes overlooked and, you know, corporate sponsors and philanthropic sponsors and all these folks are [00:51:20] jumping in. Alejandra: But really the heart of this right now. Is to make that path for the next generation smoother and allow them to be able to focus [00:51:30] again on what they need to focus on, which is launching businesses, coming up with ideas, graduating, whatever that looks like. And so that, that's my hope. And if, if [00:51:40] anyone's interested, it's first gen.org, that's where they can contribute or support students or just watch the journey. Alejandra: Because when you read these young people's [00:51:50] stories, there is a nothing more inspirational. Leah: Oh, that is so incredible. So you started this, you self funded it. You're now bringing in corporate sponsors. [00:52:00] Is there a call for applications open right now or what's the timing? How does that work? Yes. Alejandra: The call for application is open now and the grants will be distributed on national first gen day, [00:52:10] which is November 8th. Alejandra: So if you know anyone who fits this bill or you have an Alma mater that you think you're the students would benefit from knowing about [00:52:20] this, everything's on my Instagram and on the website. Stacy brown Speaker 13: [00:00:00] Some people are motivated, oh, I wanna prove this person wrong. They think I can't do it because of my circumstances, but I was taught to never let your circumstances define you. They may be what they are, but they should never [00:00:10] define who you become. So living that way for me was always moving forward, but then I felt this responsibility to do well and do good.[00:00:20] Speaker 13: For the people who couldn't handle their circumstances. Speaker 14: Hi everyone. I'm Leah Sullivan, and this is Breaking Precedent. Not only did I found TaskRabbit, one of the [00:00:30] pioneers of the gig economy, I'm now a venture capitalist backing the next generation of rebels. In this podcast, we dive deep into the stories of innovators who are pushing societal boundaries. Speaker 14: Challenging [00:00:40] precedents in setting new ones in their fields today. My guest is Stacey Brown Philpot, former CEO of TaskRabbit, longtime Google exec board leader at hp, Nordstrom and [00:00:50] StockX. And now with her debut Venture Capital Fund, cherry Rock Capital. She is one of the most rare leaders whose operated at. Speaker 14: Every level of text [00:01:00] evolution from the don't be evil era at Google to reshaping the gig economy and pioneering new models for inclusive capital. Stacey is someone in my life I [00:01:10] deeply admire. We've been in the trenches together for many, many years, and I hope you enjoy this very candid conversation with one of my dearest friends. Speaker 14: Let's dive in. [00:01:20] Alright, Stacey Brown, Philpot, thank you so much for joining me here on Breaking Precedent. Speaker 13: Excited to be here. Speaker 14: Me too. I know that we've been wanting to do [00:01:30] this for a long time. Yeah. Um, I always kick things off with an icebreaker. No, you and I have known each other a long, long time, so I feel like it was hard to [00:01:40] pick this icebreaker 'cause I wanted to pick something I might not know about you. Speaker 14: Um, I don't know if you're gonna surprise me or not. We'll see. Okay. So you and I have spent a [00:01:50] lot of time in the boardrooms. But if we had to swap the boardroom for a karaoke mic, Speaker 13: okay, Speaker 14: what song would you choose to get us [00:02:00] hyped up for the next big thing? What would it be? Speaker 13: So, you know, I gotta go to my Detroit Roots and I gotta pick Lose [00:02:10] Yourself by Eminem. Speaker 14: Oh my God. Speaker 13: Because you know, you only get one shot, so Speaker 14: that is so, so good. You know what, I knew you were gonna go Detroit, but I [00:02:20] didn't pick Eminem. I love that. Speaker 13: Ah, there you go. Speaker 14: I thought it might be like a Motown or something. There are many. That's, Speaker 13: I gotta keep it interesting for you. Speaker 14: [00:02:30] So I dunno if I ever told you this. Speaker 14: I'm interested if I have. But when we were going up and down Sandhill Road, right, and like pitching VCs. Mm-hmm. [00:02:40] I did have this one hype song that I had only play when I was by myself in the car. Speaker 15: Okay. What was it? Speaker 14: It's a little embarrassing, but it was [00:02:50] really helpful. It was at the height of Britney Spears. Speaker 15: Mm-hmm. Speaker 14: And it was that song about how she's like the center of the ring and she's the [00:03:00] circus. Uhhuh Uhhuh. And I'd be like, yeah, I'm just gonna go in there and I'm gonna be the ring master and we're gonna get this shit done. [00:03:10] That was my song, was my head. All Speaker 13: right. There we go. Speaker 14: Woo. I haven't heard it in a long time, Speaker 13: but we Speaker 14: got Speaker 13: it done. Speaker 13: So there's that, right? Speaker 14: We got it done. We [00:03:20] got it done. Thank you, Brittany and Eminem. So before Google and TaskRabbit and SoftBank and Cherry Rock and all these [00:03:30] amazing things you've done. I wanna go back to, you mentioned Detroit. A little girl in Detroit, four generation household full of [00:03:40] women. Amazing. Speaker 14: Yes. Take us back there. What did that teach you growing up about community, family, standing up for yourself, [00:03:50] everything. Speaker 13: Yeah. Well, it taught me everything. It was my great-grandmother, my grandmother, my mom and me in that house. And then there were three other. People, my [00:04:00] men in the house, my brother, my grandfather, and my uncle. Speaker 13: So there was seven people in the house total. But these women ran the house and you know, talk about the [00:04:10] matriarch. Really ruling it was that my grandmother always. Taught us to look out for other people, and she would send food next [00:04:20] door. Either way, depending on who needed an extra plate or down the street, or if somebody was sick, we would take something and pick them up from something from the store, and we [00:04:30] didn't have a lot. Speaker 13: So she taught us like, even though you don't have much, you have to give to other people, and that was so important. She taught us about standing [00:04:40] up for yourself when. You know, there's always gonna be situations people don't wanna work with you, interact with you like you do anything. And I remember [00:04:50] being pushed outside the door to like stand up for myself when these girls didn't like me. Speaker 13: I was walking home from the bus stop and they just kept picking on me. And she was like, they're gonna keep picking on you until you [00:05:00] make it stop. And I was like, oh Speaker 14: yeah, what did she have you do? Speaker 13: We don't fight anymore. But it was a fight I had to fight for myself and that was scary [00:05:10] and hard. But it taught me that even in a world where there's people who can help you out, sometimes you have to be the person to end something, [00:05:20] and it didn't happen anymore after that. Speaker 14: Hmm. So fascinating. I mean, I think you and I have talked a lot about this too, like there are always [00:05:30] people that are just not gonna vibe with you, right? Mm-hmm. And that's such an interesting story growing up. How did that lesson translate into [00:05:40] business, into boardrooms, particularly when you're the only woman or the only black person in that room? Speaker 14: How did that apply? Speaker 13: Yo being the only one [00:05:50] of something wasn't about. Like or not like, but that helped me deal with the discomfort. You walk into a room and you're [00:06:00] not sure how people feel about you, you actually learn to care less about what they think, just based on appearances, your color of your [00:06:10] skin, the gender, and more about how they respond to your perspective. Speaker 13: So I showed up at the HP board [00:06:20] meeting. I was the youngest person to join that board. I had a business being there 'cause they invited me to join the board. But, and a deep down in my little soul, I'm like, am I [00:06:30] supposed to be here? I have earned this seat at the table. Speaker 14: Yeah. Speaker 13: And it just taught me, you know what? Speaker 13: You have something to say, Stacy. And even if people don't like [00:06:40] it Speaker 15: mm-hmm. Speaker 13: Say it. And so I've become the person who says the thing that. People maybe don't wanna hear. Mm-hmm. Or it's hard to hear, [00:06:50] but it can move a conversation forward. It can move a decision forward. You and I had lots of moments where Speaker 14: mm-hmm. Speaker 13: We would debate stuff and discuss things mm-hmm. At TaskRabbit [00:07:00] where I had to move something forward Speaker 14: Yep. Speaker 13: And look back and be happy. Speaker 14: Yeah. Speaker 13: That we did. Speaker 14: It's such a skill [00:07:10] because it is uncomfortable, right? It's, and a lot of people don't wanna sit in that discomfort. But that is something I admire about you, is you're able to bring [00:07:20] that candor and that truth. Speaker 13: Yeah. You Speaker 14: know? Speaker 13: I called the other day from a founder. Mm-hmm. And he wanted to make a decision in the company. Speaker 14: Mm-hmm. Speaker 13: [00:07:30] And I said, this is what you should do. Decision A. It's like the obvious thing to do, and here's why. And I know it's hard, but A, and he chose [00:07:40] B. He said B is a little bit easier and more palatable. Speaker 13: And he wasn't wrong. B was definitely more palatable. And then, yeah. You know, the other day he called me, he said, you know what? [00:07:50] We're going back to decision A. Speaker 14: Mm-hmm. Speaker 13: And I CC and he said, you know, you, you were the one who. Told me that we should do [00:08:00] Decision A and I said, yeah, and I didn't say I knew I was right. Speaker 13: Nothing at all. I said, great. Right. Yeah. I'm so glad that you're going with decision A now, and I hope Decision B helped in [00:08:10] some way and let me know how I can be helpful, right? Speaker 14: Yeah. That's the thing about you, Stacy, is I feel like. You are able [00:08:20] to withhold judgment. You're never the one that's gonna say, well, you should have done that before I told you so. Speaker 14: No. Like you really do make people feel [00:08:30] comfortable. I think pushing back, challenging, exploring, coming back around, changing decisions, and that's a skill too, because that's not always [00:08:40] easy to just let people do. Right. So yeah. Let's talk a little bit about education. What was school like for you? Was there [00:08:50] a moment that you really felt like education was an important piece of your growth and your path? Speaker 13: You know, my mom always taught us that. [00:09:00] People can take things from you, but they can never take away what you put inside your brain, what you learn. Mm-hmm. And so she focused so much on education. [00:09:10] I remember one summer when I was in elementary school, we leave school and they give us this list of books to read. Speaker 13: It was either 30 or 40 books on that list. But they were super short. And I, if you read [00:09:20] all the books, you get like something. At the beginning of the school year. So I was determined to basically read all these books. And so basically you read like a book every day and a half. Um, and they were [00:09:30] short, but it really taught me that I just love, I've developed this love for reading. Speaker 13: I developed this sort of. Passion for just learning and [00:09:40] getting lost in stories. If people always ask me, you know, what's your favorite business book? I don't have any business books because I like to read fiction. Mm-hmm. I [00:09:50] love stories. I love, I hate ending books because it's over. The story's over and I'm always like, Speaker 15: oh my God, it's gonna end. Speaker 13: So it's just [00:10:00] the learning and the process of learning and learning how to learn was something that. I just reveled in and I was a quiet kid in school and I [00:10:10] played outside, but I wasn't always running the streets. And so I would find a lot of solace and escape in the power of different [00:10:20] stories and the books that I read. Speaker 14: So it was an escape. Was there a piece of you that was competitive about it too and just wanted to Speaker 13: Yes. Speaker 14: Finish all the books? Speaker 13: 100%. Like that makes sense. Yeah. You tell me [00:10:30] to read 50 books, I'm like, all right, I can read 50 books. Speaker 14: That is awesome. Speaker 13: 60. Okay. Right. Speaker 14: That's so funny. I've [00:10:40] recently got more into fiction now as well. Speaker 13: Mm-hmm. Speaker 14: Are there genres, authors like series that you like right now? Speaker 13: You know, [00:10:50] I just read Homegoing, a Stanford graduate, wrote this book about these two sisters and their parallel lives of growing up, one in [00:11:00] Africa and one who's was sold into slavery and so then grew up in the United States. Speaker 14: Hmm. Speaker 13: Just one of those stories that just, it's the way they tell the story and they go [00:11:10] back and forth and you just are transported into different. Speaker 13: Parts of society and parts of life. That's really kind of fun. Speaker 14: That's so fun. You ended up [00:11:20] at Penn? Mm-hmm. What drew you there? How did you learn about Penn? What was the path like getting there? Speaker 13: The path to Penn was, again, [00:11:30] this is the competitive person in me, maybe. Mm-hmm. As you brought up that word, I had a full scholarship to the University of Michigan, which at the time was the number [00:11:40] two business school. Speaker 15: Wow. Speaker 13: And I wanted to study business. I was in the counseling center and I saw this book and it said the number one business school at the time was [00:11:50] Wharton. I know what's Wharton. I didn't even know what it was. I didn't know what Penn and Ivy League school was. Speaker 15: Mm-hmm. Speaker 13: I said, well, you know what? I should probably look at this school [00:12:00] because it's the number one school. Speaker 13: I'm going to the number two school, which is close to home. Speaker 14: Mm-hmm. Speaker 13: So I applied and I remember [00:12:10] my counselor. Really thinking, well, you know, you've got a good option already. You may not get in to pen. It's a tough school to get [00:12:20] into, so of course then I definitely had to apply. Then. You really Speaker 14: wanted it. Speaker 14: Yeah. Speaker 13: I didn't even know what I was signing up for, but anyway, I signed up for it and it was one of the best decisions that [00:12:30] I made. Michigan would've been a great institution, but I met my husband at Penn and so had I not gone there, we wouldn't have met. Speaker 14: That's amazing. You [00:12:40] then went on to Goldman. You were at Google. Speaker 14: I mean, it's so interesting to me too because those cultures. So different. What was it like [00:12:50] starting at a culture like Goldman and then transitioning over to Google? Speaker 13: Yeah. There's a lot different about Goldman and Google, but there's a [00:13:00] lot that's the same. Okay. Which is both of them had a very strong culture. Speaker 14: Hmm. Speaker 13: Very strong, very, it wasn't transient and it was [00:13:10] very kind of founder leader led. Hmm. And you had to drink that Kool-Aid to really be successful at both of those firms. Yeah. You cannot waver at [00:13:20] all. And Goldman at the time, had a culture where they promoted from within. They very rarely brought people from outside the firm into senior roles. Speaker 13: [00:13:30] And when they did, that person was called a lateral. Right. They had like a. It was literally, it was very rare, which really helped the culture. And they were people focused, very [00:13:40] much focused on the client services businesses, the people are the asset and they were so people focused around who you are, the talent that you bring, [00:13:50] the perfection that you bring to a transaction. Speaker 13: I worked in mergers and acquisitions, the need to be right all the time. Right. And the focus on the people. And [00:14:00] Google similarly was also. Focused on people. I mean, the culture, the things around OKRs and the free food and all the things that, you know, [00:14:10] mark Silicon Valley today are things that Google started doing because they just felt like we just wanna hire smart people who can do great things and let [00:14:20] them go and figure it out. Speaker 13: The difference is, I didn't have to wear a suit or stockings, you know? Yeah. I could show up in my jeans and my t-shirt. I Speaker 14: and bring your two, Speaker 13: two [00:14:30] dog in. I took my dog to work, right? So, hey, let's be clear, like there was some very big important and helpful differences between those two companies. [00:14:40] Speaker 14: Yes. I remember the day you brought little Zeus into TaskRabbit and he met Kobe who was Yes. Speaker 14: I mean, like Kobe was 10 pounds, right? [00:14:50] Zeus was like this cute little tiny guy. So sweet. So you also went to Stanford, GSB. I'm curious, because you know, I've heard you say [00:15:00] that Detroit gave you this resilience, and I see that in you. Speaker 13: Mm-hmm. Speaker 14: And that Stanford gave you perspective. So I'm curious, when those two things collide, the [00:15:10] resilience, the perspective, how does that set you up for success? Speaker 13: You don't think you're learning resilience, by the way, when you're learning it. No one's walking around. I guess [00:15:20] today we do that with our kids. We're gonna teach you resilience, but you're just growing up and doing things that Speaker 14: are hard, hard. You just make things really hard for them. Isn't that what you do? Speaker 13: [00:15:30] Yeah, sometimes. And now it was just hard. Life was hard. Speaker 14: Mm-hmm. Yeah. Speaker 13: But what it taught me was that I can do hard things, and the other side of doing hard things [00:15:40] is often something good. Whether it's getting a good grade or accomplishing something that I was trying to accomplish, I was a baton twirler and we would like do hard [00:15:50] routines was a majorette in high school and that was what it taught you. Speaker 13: It was like, and despite how hard it is, you will survive. Like there are very few [00:16:00] things that can hurt you. But then coming to Stanford, it just changed my perspective coming out to Silicon Valley. Being in this [00:16:10] environment and the mantra, Stanford was changed lives, changed organizations, changed the world. Speaker 13: So you're not just made to do hard things in the town that [00:16:20] you grew up in, but actually you're made to do things at a global scale. Mm-hmm. On. And the expectation is what you do with [00:16:30] your education should far exceed anything that you can accomplish on your own. Changing lives, changing organization. You have to work with [00:16:40] other people to accomplish things. Speaker 13: And so it taught me a lot about collaboration, empathy, understanding, bringing that resilience into [00:16:50] environments where you have to learn how to also bring other people along. Mm-hmm. I had a wonderful time at the GSB. Speaker 14: Yeah. When you think about that journey [00:17:00] from Detroit classrooms to Penn to Stanford. And you look back, what do you wish educators understood about spotting potential [00:17:10] in students like you? Speaker 13: Yeah, I wish they understood. Don't shortchange me. Speaker 14: Mm-hmm. Speaker 13: Right. [00:17:20] So sometimes when you look at me like that counselor who's like, oh, I don't know. You know, it's really hard to get [00:17:30] in. And I was smart. I was straight a student and I was. You know, second in the class salutatorian, like, you know? Speaker 14: Yep. Speaker 13: And yet there was this sort of, Speaker 14: and yet, yeah. Speaker 13: [00:17:40] And yet. Speaker 14: Mm-hmm. Speaker 13: So we want to be pushed. Speaker 14: Mm-hmm. Speaker 13: We can do it. We can make it. It is okay. [00:17:50] And yes, we should take care of our mental health and all the things that happened after we became adults. The care about mental health, we were kids. We didn't get that part. Leah, [00:18:00] did we? Speaker 14: No, definitely. That was not a thing when we were growing Speaker 13: up. Speaker 14: No. Speaker 13: We wanna be pushed. Speaker 14: Yeah. Speaker 13: And we wanna learn and we wanna make an effort. [00:18:10] And so don't give up on us. Don't think just because we came from a difficult environment or you know, our parents got divorced when we were young, or we don't always have the food [00:18:20] that we need to eat, that we can't make it, we can. Speaker 14: Was there some pieces of that too that almost motivated you more in some way to make [00:18:30] it, Speaker 13: it was motivating and it also felt like. A responsibility at some point too. Speaker 14: Mm-hmm. Yes. That Speaker 13: I feel that where there was a motivation to prove people [00:18:40] wrong. Mm-hmm. And so some people are motivated, oh, I wanna prove this person wrong. Speaker 13: They think I can't do it because of my circumstances. Mm-hmm. But I was taught to never let your circumstances [00:18:50] define you. They may be what they are, but they should never define who you become. Speaker 15: Mm-hmm. Speaker 13: And so, living that way for me was always moving forward, [00:19:00] but then I felt this responsibility to. Do well and do good for the people who couldn't handle their circumstances, who, mm-hmm.[00:19:10] Speaker 13: Didn't have the opportunities that were given to me and didn't have the person push them through a challenging time when they really needed it, and I [00:19:20] did. And so I had to carry a load of giving back and proving that I could accomplish something with all the [00:19:30] opportunities that I had. Speaker 14: When you look back at Young Stacey in Detroit, do you see traces of the CEO you became or did that ambition kind of sneak up on you later? Speaker 14: [00:19:40] What do you think? Speaker 13: You know, my brother would say that it was always there. 'cause I was the CFO of the paper route. He, we had a paper route, [00:19:50] you know, he, it was his paper route and he, you know, wanted me to help him. So I helped him with the paper route. And so I would collect all the money, add up all the money, and figure out how much we got to keep. Speaker 13: [00:20:00] Depending on how much we collected every week. And so there was that leadership role that happened in that capacity because people always ask me, do you, did you wanna be a CEO? [00:20:10] And I'm like, I don't think I did. Even when I joined TaskRabbit, like I joined because I wanted to work with you. That was it. It wasn't like to be the CEO of the company, but I remember being in high [00:20:20] school and when I was a majorette. Speaker 13: They were like, Stacy, we want you to, you know, run the team. And I was me, why do you want me to run? And that was good. But I don't [00:20:30] think I was the best twirler. I mean, there were definitely twirlers on the team who could do like triple hole turns and I could do a double hole turn. Like there was definitely skills that I was still trying to master [00:20:40] at this time. Speaker 13: Mm-hmm. And they're like, well, you're really organized and so we think that you can. And so then I was the captain of the team. Yeah. So there was, there were moments where I stepped [00:20:50] into these leadership roles. Not because I was gunning for it, but because I just, Speaker 14: yeah. Speaker 13: Obviously demonstrated some natural abilities. Speaker 14: Yes. That makes sense. [00:21:00] That resonates. So we have to talk about it. We have to talk about TaskRabbit. Speaker 13: Yes, we do. Speaker 14: I founded it. You scaled it together. We proved that [00:21:10] trust technology could coexist. We pioneered the gig economy together. It was quite the ride. Mm-hmm. So many stories. I mean like a lot of [00:21:20] stories that we won't have time to get into so many. Speaker 14: I'm curious, let's start with when you first walked in. To our offices. We were about [00:21:30] 60 people. We had no processes. All of our communications were breaking down. We had our first employee that had just had a baby, and [00:21:40] so we had converted like this broom closet into like a mother's nursing room. It like, we had no idea how to scale this [00:21:50] organization. Speaker 14: What did you really think when you walked in that day? Speaker 13: Man. I was like, oh lord, we got a lot to do. The funny thing is, is that it brought me [00:22:00] back to the Google days. Like when I joined Google, it was a thousand people. And I think we may have had a mother's room at when I joined the company, but you know, it [00:22:10] was like a room with something else in it. Speaker 13: Yeah, it did exist. And we were just running around trying to figure out what we were supposed to be doing in the company. [00:22:20] Mm-hmm. And so on some dimension it was refreshing. On another, I was like, oh, I looked in the swag closet and I'm like, there's this little corner and then there's a person with the little milk [00:22:30] thing. Speaker 13: Like we have a lot to do. Speaker 14: Mm-hmm. Speaker 13: But the other thing that I noticed was the culture there. Like the energy was incredible and [00:22:40] everyone was so happy to be there and so excited. And when you leave a big company like Google, you think, wow, this is the greatest place on earth. There can't be anywhere [00:22:50] else. Speaker 13: That's great. And I walked into TaskRabbit and I was like, oh my God, these people are, they're having a great time. This is great. Speaker 14: We're, we're, we're having a great time. Yeah. Speaker 13: You know, you [00:23:00] also instituted, you know, a big cultural pivot in the company, which was to bring in. Free food, so. Tell me a little bit, like what was that strategic [00:23:10] move about? Speaker 14: I remember when you were coming from Google and we were talking, and culture for me was always something that just was naturally important. It was [00:23:20] just organically something. That I felt was so important. Mm-hmm. People that you work with and the culture and why we're doing this. I mean, I think we were both very mission [00:23:30] driven, right? Speaker 14: And mission oriented. So I remember chatting with you and I was like, you know, the culture and having you come in, like what are some things that we could learn. From [00:23:40] Google and I think one of the things was like free lunch. It was awesome. We would bring in lunch every day for everyone. People would gather, right? Speaker 14: Yes. And [00:23:50] chat. Speaker 13: Yes. Speaker 14: For you, what were your sort of like hopes with instituting that program and what did we see at Drive? Speaker 13: It was exactly what [00:24:00] you said it was. It was exactly that. People would sit down and talk to each other and people who may not work together would talk to each other. Mm-hmm. [00:24:10] Because before that, there was this 90 minute gap in the middle of the day. Speaker 13: Not everybody mm-hmm. Left for lunch at the same time and not everybody came back at the same time. So somewhere in [00:24:20] the middle of the day, you kind of have this lull of noise, sound, energy. 'cause everybody went to get food and eat. The groups of people would go [00:24:30] together. Nobody went alone. So you'd have small groups going together, but you didn't have that buzzing energy inside the office. Speaker 13: Sustained. And that [00:24:40] made the company feel like a family. Speaker 15: Mm-hmm. Speaker 13: That looked out for each other, that stood up for each other, that took care of each other. And that's really what [00:24:50] the food was about. It was less about what we actually ate, and it was about the feeling that we had from being together. Speaker 14: I also think it's sort of looking [00:25:00] back, you know, you mentioned people would go out in like little groups. Speaker 14: It sort of broke up those groups Speaker 13: Yes, Speaker 14: too. Because yeah, people would like mix and mingle and you'd have the engineers sitting with the [00:25:10] marketing team. Speaker 13: Yes. Speaker 14: That was goodness too. It was great. Speaker 13: And they would hear stories and maybe they don't talk 'cause they're shy or quiet. Mm-hmm. But then they, it would just, they would be a part of it, you know? Speaker 13: Mm-hmm. [00:25:20] And then we would celebrate birthdays. Speaker 14: Yeah, Speaker 13: until we got to daily and then we had to stop doing the birthdays every day. 'cause then we got to the point where, man, we were [00:25:30] celebrating everybody's birthday every day. Remember we had to, had to go to monthly. We still, that's right. The cultural value of celebration. Speaker 13: But we had to shift to monthly. 'cause otherwise you would [00:25:40] have cupcakes and cookies. Every day. Speaker 14: Every day. Which, you know, it's not awful, but I remember that. I remember that. Okay. This is a big question that [00:25:50] I think both you and I have had enough time and perspective to weigh in on, and you know, TaskRabbit was a tech company built on human trust. Speaker 14: Again, I think that's why the [00:26:00] culture there was so important. As we look back now with sort of 2020 hindsight vision, do you think the industry is honored that [00:26:10] human side of the gig economy, or do you think that it's broken? Speaker 13: I think we're challenged now with human trust because of [00:26:20] ai. There's this sort of fear of what the machines will do to us. Speaker 13: And when we were [00:26:30] starting in building TaskRabbit, it was about connection. Speaker 14: Mm-hmm. Speaker 13: And the best part of, I don't know about you, but my week was when Wednesdays we would [00:26:40] have taskers come in and tell their stories. And it was for the design team and engineering team and the product teams to sort of hear mm-hmm. Speaker 13: From our taskers [00:26:50] some of their stories about how. Because they tasked on TaskRabbit, they could afford a job that allowed them the flexibility to pick their kid up [00:27:00] from school every day. And remember the Tasker house where they all lived together and shared work with each other, and we'd have such [00:27:10] good stories of clients being saved from so many things. Speaker 13: Somebody told me about a passport story. The other day of, you know, getting in line for my kid's passport or, [00:27:20] you know, making sure my party was successful and that human connection was something that was so important and we were fostering that. [00:27:30] Every single day with the tasks that we did. And this person was a total stranger. Speaker 13: So by definition mm-hmm. It was built on trust. Yeah. It was built on trust in [00:27:40] our platform that we had the right process to bring people in that we're going to do the right thing. And when they didn't, we corrected it and made [00:27:50] people whole. Like we lived up to that in every way possible. And so I think today about, well, how do we keep human connection? Speaker 13: How do we keep that trust with. [00:28:00] The way that information is flowing these days. Speaker 14: Yeah, I would agree. And I would add, I think the special thing about TaskRabbit, I still think this is [00:28:10] true today, is every task, every job, every opportunity, every connection is unique and it's different and it deals with different skills [00:28:20] and different requests and different people, right. Speaker 14: And I think a lot of the gig economy, if you look broader. Has been commoditized. And [00:28:30] it's been commoditized because it scales better, faster, easier, right? Like there's just more growth in commodities. And that for me [00:28:40] was always the challenge with TaskRabbit is how do you not commoditize yet, still scale? Speaker 14: The unique business that we have [00:28:50] and made it really hard, Speaker 13: and I think we did some things, we changed the model and we should talk a little bit about Speaker 14: Yes. Speaker 13: It wasn't always, [00:29:00] always perfect, right? Yeah, Speaker 14: yeah. Yeah. Speaker 13: We went from the Etsy for services model to the direct hire model, and that rattled some people, [00:29:10] but you and I both know it. Speaker 13: It saved the company. So Speaker 14: it did. It saved the company, but it wasn't without the TaskRabbit logo in flames in TechCrunch. Yes, [00:29:20] Speaker 13: correct. Speaker 14: One morning when we woke up. Yeah, Speaker 13: right, right. You tell me like, let's go back a little bit, like what was that [00:29:30] move about and. When you're the founder. It's your baby, you know? Speaker 13: Yeah. Why did you wanna change the bath water? Right? [00:29:40] Speaker 14: I know. Well, I mean, I think that was part of what I was just describing, is we were growing, we were scaling, but you know, it just wasn't fast enough. [00:29:50] And this Etsy for services model, this marketplace sort of bidding auction style. It was so much friction, it was not going to scale the way [00:30:00] we knew that we could, the way that a venture backed company needed to scale. Speaker 14: Right? So, Speaker 13: yeah, Speaker 14: I remember being pregnant with [00:30:10] Amelia and going out on maternity leave, and we had decided to do the launch in London. Which was gonna be the test of the brand new product. Right. [00:30:20] And so you were very much leading that effort. You were in London, you know, launching that market, getting taskers trained on this new model. Speaker 14: Honestly, looking back. [00:30:30] It was such a heavy lift. It was like millions of clients, 60,000 taskers brand new product. Like we literally threw away the code [00:30:40] base, right? And like started from scratch in London. I don't know if I could stomach doing that again. It saved the company, but it was so, so hard, and [00:30:50] I think that's a great example of. Speaker 14: Ah, resilience. Yeah. Um, you know, just really [00:31:00] being able to push through power, through, have conviction in something. Yeah. Speaker 13: Yeah. Speaker 14: Particularly that London launch. Right. Because when London started working, we're like, oh, whoa, [00:31:10] now we have to bring this back to the us. Yes. That was the hard part. That was Speaker 13: hard. Speaker 13: Yeah. But the conviction piece was something that. As leaders, we had [00:31:20] to hold hands around this. Yeah. Remember we gave ourselves a couple of months. Speaker 14: Yeah. Speaker 13: Despite the flaming symbol on TechCrunch, believe that this is [00:31:30] the right thing to do. Have some faith and some conviction that we were doing the right thing and we were and it was. Speaker 13: Right. Yeah. And I think that, you know, [00:31:40] those are some of the hard things about running the company, working with you. We navigated through. Mm-hmm. That you can't teach this, you [00:31:50] can't plan it. We were not expecting, but it ended up being the right thing to do and Speaker 14: Yep. Speaker 13: You know, we weren't doing it for the sake of scale. Speaker 13: Right. We were [00:32:00] doing it because we felt that in order for this business to exist around the world, we had to have a business model. [00:32:10] That could be profitable someday. Otherwise we were gonna go out of business and nobody was gonna have a job. Mm-hmm. Or be able to use this service. Mm-hmm. And I think that kept us [00:32:20] grounded personally. Speaker 13: Yeah. I don't know if you feel the same way. Speaker 14: Absolutely. And I still see TaskRabbit today as my first child. Right. It's like, to me it was like this [00:32:30] living, breathing. Organization and I just felt like we can do better. We can do better by you. You deserve better. Right? That was part of it. Okay, so I get this [00:32:40] question a lot and I'm curious, I'm sure you do too, how you would answer it, but if you and I could go back and run TaskRabbit together today with ai, [00:32:50] with climate tech, with worker ownership models in play, what would a TaskRabbit. Speaker 14: 3.0 that's AI native look like. Speaker 13: Oh [00:33:00] man. I think we still have humans. I don't know if you Are we still humans agree? I don't think we're robots still humans. We're definitely humans. Humans. Speaker 14: I agree. Yeah. Speaker 13: Um, but [00:33:10] the agents are the app now, right? Like there's a lot more sophistication in how we communicate, what we communicate, what we can [00:33:20] know about a client before we show up. Speaker 13: The tasker shows up for a task. So that would be a real interesting way to think about how we would use [00:33:30] agents. And then I think there's an element of the environment of understanding what kind of task could we really do. Mm-hmm. And [00:33:40] reimagining some of that. It's like, it's not just coming in and like fixing one thing in your house, but Speaker 14: Yeah. Speaker 13: What if we could just reimagine the way we think [00:33:50] about making everyday life easier for everyday people? Mm-hmm. And. Documenting a lot about their life and figuring out how to help them with it. Speaker 14: I [00:34:00] love that. I would add, you know, at one point we scaled into, you know, a sizable data science team and organization, right? Speaker 14: And it took a lot of work and it was always [00:34:10] hard for us to be able to predict in real time how many taskers by what skillset, in what zip code, at what time of day, right? We needed. And I think with [00:34:20] AI now, there's so much that could be leveraged behind the scenes. To make the tasker side more efficient and scaled and [00:34:30] optimized. Speaker 14: Like to me that would be a big unlock and it'd be a lot of fun to see. Speaker 13: Totally agree. Speaker 14: How you can leverage all of that ai because it would take us like a [00:34:40] month to like do these data science analysis, right? Speaker 13: Yeah. Speaker 14: And now you could just put it all into chat, GPT, and like in five minutes have answers. [00:34:50] It's pretty amazing. Speaker 13: And customer service. I mean, imagine taskers on tasks needing help. Speaker 14: Yeah, yeah. Speaker 13: Well, we, yeah, I would have to call and call us and, you know, [00:35:00] procure things. Yep, Speaker 14: yep. Speaker 13: That would be so much easier. Speaker 14: Okay, so I'm gonna ask you if you remember the day that we sold [00:35:10] TaskRabbit to ikea? Mm-hmm. Because I've mentioned this, I think, on the podcast before. Speaker 14: I remember this board call. It was me and you and Barry and Todd, and. [00:35:20] Rob, I think, and it was like the final vote. What do you remember about that board call? Do you remember it? Speaker 13: I remember you went [00:35:30] last, if I remember correctly. Speaker 14: Yeah, I did. Speaker 13: And that was it. And I don't know if you remember, but a couple days before we had some challenges with the deal [00:35:40] negotiation. Speaker 14: I do Speaker 13: that. Almost blew everything up, but got it back on track and Speaker 14: we were like, Stacy, you need to call someone. [00:35:50] Speaker 13: Yes. Speaker 14: Yeah. Speaker 13: It was really a moment of truth, honestly. Mm-hmm. Where it was like, okay, this deal might not get done. Speaker 14: Yeah. Speaker 13: So once we [00:36:00] cleared up that issue, we were now ready to vote on the deal and it was a call. Speaker 13: And you were the last person to go and, and I was like, [00:36:10] orchestrating everyone has to like vote yes. Vote yes. And that's what I remember. And I remember wondering like how you felt in [00:36:20] that moment. Speaker 14: Yeah. ' Speaker 13: cause I know I was, I had gone from excited to do this deal to, oh Lord, it's not gonna happen. [00:36:30] And Speaker 14: mm-hmm. Speaker 13: Leah and the board are not gonna be happy if this deal doesn't happen since we worked so hard on it. Yeah. So 48 hours later we're now voting on the deal. So there's a [00:36:40] sense of relief that I had. Yeah. That we had gotten to an outcome that worked for everybody. Yeah. Including [00:36:50] the employees at the company. Speaker 14: Yeah. Speaker 13: Which are often forgotten and mm-hmm. I was wondering how you felt. Speaker 14: Oh gosh, were out of me. Speaker 13: Were you? Speaker 14: You know? [00:37:00] Oh my God, yes. What was Speaker 13: the, you know, Speaker 14: what was it? Speaker 13: Yes. Speaker 14: I do remember feeling a lot and I remember everyone going around one by one, and I went [00:37:10] last, like, you remember? And I just remember everyone saying something really nice before they voted. Speaker 14: Like, you know, Barry was like, we've been on this journey. We're so [00:37:20] proud of you two. Thank you. Like Todd, right? Rob Chesney, who you know, we just love. He was our independent board director. An [00:37:30] operator came from eBay, right? Mm-hmm. Like he really understood how hard we fought for this business. And you, like you said. Speaker 14: Had to do a lot of [00:37:40] heavy lifting to get this deal done. And so when it came to me and I had heard everybody's comments, I sensed your relief. I was also [00:37:50] relieved. I was also, it was like this weird sadness because it was over for me. It was really over because I was on the board at that [00:38:00] point. You were CEO? Speaker 14: Mm-hmm. I was no longer gonna have any sort of connection. Financially or whatever to this business. It was emotional. It [00:38:10] was emotional. Yeah. I mean, it was like a decade of my life. Right. But I was so proud of you. I was so grateful to you, Stacy. I mean, honestly, like I said, when you came in, we were [00:38:20] 60 people. Speaker 14: We were just like. Trying to figure out how to get this business to thrive, and you did. You came in and you [00:38:30] partnered with me and the team and the board, and you did that. And so I was so grateful, so proud. Ah, and But it was a lot. It was a [00:38:40] lot of emotions. Yes. Yeah. Speaker 13: Yeah. Speaker 14: It was a big moment. So we did get the deal done. Speaker 14: Yes. We sold to Ikea. Speaker 13: Got it done. Speaker 14: You stayed at IKEA for a bit? [00:38:50] I did. And then I think what's more interesting is what you have done since then. You have shifted from operator to investor. You've joined boards from, you [00:39:00] mentioned hp, Nordstrom StockX. You helped launch SoftBank's, a hundred million dollar opportunity fund for Black and Latinx founders. Speaker 14: Let's [00:39:10] talk about all of that. What was the shift like from operator to investor for you? Speaker 13: It has been a big jump. I. Had always thought I'd [00:39:20] become an investor. When I applied to Stanford for business school, I wrote my essay about becoming a vc and life took me different. It took me to Google and [00:39:30] then to TaskRabbit. Speaker 13: And I loved operations. I loved building things and building companies and running companies. It was a full circle moment for me to go back to the thing that I came to Silicon Valley [00:39:40] to do. Speaker 14: Mm-hmm. Speaker 13: But the shift in perspective. Was from this short term, you know, by day, by hour, [00:39:50] sometimes, like when we're negotiating a deal to, well, we're not gonna know if we're good at this for seven to 10 years. Speaker 14: Mm-hmm. Speaker 13: And so the short term thinking is, in [00:40:00] the long term thinking has been a big adjustment for me. The other one is just how much time I spend thinking than doing. When you're the [00:40:10] COO, you are doing a lot. When you're the CEO, you're doing a lot, and as an investor now, I spend my time thinking, is this a good deal? Speaker 13: Is it not? What are the [00:40:20] right markets to be thinking about? How do we set up this fund? Now there's a heavy operational lift to setting up a venture fund. Mm-hmm. That people who join a fund do [00:40:30] not have to go through. And we can talk about that. So if you have experience with that, I know. Yeah. So we can talk about that too. Speaker 13: But this shift from short term to long term [00:40:40] from doing to thinking has been this sort of mental shift. I get to exercise different parts of my brain. And I love learning new things. Yeah. So I'm having a lot of fun with it. Speaker 14: Yeah, I [00:40:50] feel that way too. I like the learning piece of it. I wanna talk about just the impact that you're having in this industry as well, and the opportunity fund at SoftBank, [00:41:00] how that's influenced Cherry Rock. Speaker 14: Can you take me back to, after George Floyd's murder, you and Marcelo decided to act at [00:41:10] SoftBank, and how did it feel to move from. And outrage into something operational. Speaker 13: Everybody was outraged. And I [00:41:20] remember around the time the opportunity fund was being established, I was also transitioning out of TaskRabbit. Speaker 15: Mm-hmm. Speaker 13: At work, dealing [00:41:30] with the emotional trauma that's been caused by this horrible incident. Mm-hmm. On everybody in the company, regardless of your [00:41:40] race. Then hosting conversations. We were doing these because it was COVID remember. So we were doing these virtual crucial conversations [00:41:50] to really bring people together. Speaker 14: Mm-hmm. Speaker 13: And separately, I had this conversation with Marcelo and this other man named Paul Judge, who were my Henry [00:42:00] Crown Fellows class. And we were on a WhatsApp and we were outraged. And the question was, what else can we do? How do we show. [00:42:10] People that there's a different side. Mm-hmm. To black people. Speaker 13: Mm-hmm. And why is it that our news is this [00:42:20] kind of news that makes global news? Like, why can't it be something else? Mm-hmm. That's closer to [00:42:30] what we do every day. How do we elevate the stories and the lives of people in a positive way? [00:42:40] So Marcelo was the COO at the time at SoftBank and was able to get a hundred million dollars for the three of us, me, Marcelo, and Paul, to set up this [00:42:50] fund that focused on investing in black and Latina entrepreneurs who were building software companies in the us. Speaker 13: And at the time, a hundred million was the largest fund [00:43:00] that was dedicated to that population of people. Yep. And it was intentional and a lot of people said, oh, we don't, are you gonna find enough companies [00:43:10] to invest in? Are there enough? Yeah. Speaker 14: Tell me, tell me Speaker 13: founders. Tell me about Speaker 14: that Speaker 13: building, these kinds of companies. Speaker 13: And we were like, [00:43:20] I think so. Like, I mean, it was not a question. Speaker 14: Yeah. Speaker 13: So I remember launching this on the news and Marcelo gave out the, his email and we got [00:43:30] tons, hundreds, I bet of people that day. Yeah. We saw 2000 companies. We invested in 70 companies in that first fund. So there was no pipeline problem.[00:43:40] Speaker 14: Yeah. Speaker 13: And the fact that people questioned were we gonna spend all the money? Mm-hmm. Was crazy. Speaker 14: Yeah. On that note, that is sort [00:43:50] of the excuse we constantly here, diverse talents. It's so hard to find. Are you gonna find it? What are the structural [00:44:00] excuses that still need to die before capital can actually flow fairly Speaker 13: sometimes, and I certainly got this when I was raising my [00:44:10] fund. Speaker 14: Mm-hmm. Speaker 13: Well, is this impact, is this charity and like, just because you see a person of color doing something. Does not [00:44:20] mean that we are a charity. We are in this to make money and generate returns for our LPs and the founders that we invest in are in this to build [00:44:30] global multi-billion dollar businesses. Speaker 13: Mm-hmm. And so there's an, there's a bias there of like, oh wow, this is what a cute idea, [00:44:40] what a wonderful idea. Oh wow. This is gonna have such a big impact. We know. Mm-hmm. Because we're gonna generate. A lot of money. A lot of money, and be profitable [00:44:50] and employ thousands of people around the world, and we're definitely gonna have an impact. Speaker 13: So I think that's something else that's there, which is this. A [00:45:00] charity is not concessionary at all, so. Speaker 14: Yep, yep. I love. That you have now started your own fund, cherry Rock Capital, [00:45:10] where you're channeling that vision, that optimism into this vehicle. You closed what, $180 million? [00:45:20] 172 Speaker 13: million? Yes. Speaker 14: $172 million to invest in black. Speaker 14: Founders. Speaker 13: Yes. Speaker 14: I mean, this is [00:45:30] probably, if SoftBank at a hundred million dollars was the largest fund at the time, like 172 million, that seems like a pretty huge fund for this population. [00:45:40] Speaker 13: And that was something that we learned, which was once I figured out there was no pipeline problem, yeah, then Speaker 13: we just needed to understand. Speaker 13: Now, [00:45:50] where is the gap in the market? It's not a pipeline issue. Speaker 14: Mm-hmm. Mm-hmm. Speaker 13: We had a number of seed stage firms that exist and were being established to focus on that population. But [00:46:00] when you looked at Series A, there was a gap where you got the big multi-asset class firms that very hard to penetrate and get into. Speaker 13: So we [00:46:10] wanted to fill that gap at Series A where we could lead rounds. Write larger checks and really be catalytic to some of the most promising [00:46:20] startups that are led by black or Latina founders. And we wanna lead the round and join your board and be helpful and bring our operating expertise. And [00:46:30] that's what Cherry Rock Capital is all about. Speaker 13: We're looking for underinvested entrepreneurs who have. Incredible ideas who are outstanding [00:46:40] at execution and have the audacity to put themselves out there and make it happen. Speaker 14: You talked a little bit about [00:46:50] shifting and reframing the idea that this is not charity, it's good decision making. Speaker 13: Hmm. Speaker 14: How will you at Cherry Rock [00:47:00] hardwire that principle into your investment process? Speaker 13: One of our values at Cherry Rock is we deliver hard truths with kindness [00:47:10] and. That's an important one because you and I know on the fundraising trail, people weren't always honest with us and Oh, we have Speaker 14: some Speaker 13: stories. We didn't always know [00:47:20] where we were in the process. Right, Speaker 14: right. Speaker 13: And for us, we want you to know where you are in our process, but we also wanna tell you.[00:47:30] Speaker 13: What we like about your business, why we're investing, what our expectations are, how we're gonna hold ourselves accountable to making you [00:47:40] successful, and how we want you to hold yourself accountable to doing what you said you were gonna do. And if you can't do it, being open and honest about what that means.[00:47:50] Speaker 13: That's a level of discipline that. Breed success. Mm-hmm. The CEO of HP is all those things. He would not be running a $60 billion company if he [00:48:00] wasn't. Mm-hmm. So if you wanna be that mm-hmm. This, this is the thing that you have to do, we also want to be the kind of firm that. We know [00:48:10] we have to take a chance. Speaker 13: We leverage our faith as much as our intellect, which is another one of our values. Speaker 15: Mm-hmm. Speaker 13: Someone took a chance on us. Mm-hmm. At some point in our lives to get to where we are. So we will [00:48:20] do all the data analysis and thank God we have a bunch of AI tools that we can use and Yeah. You know, but we will build our models, we will look at the numbers [00:48:30] and we will still make judgements and make bets. Speaker 13: On who we think is gonna be the most successful. And so we want all the founders who [00:48:40] come to us to know that we're gonna take it, we're gonna do our work, but we're gonna take a chance on you if we decide to invest. Speaker 14: Yeah. You've spent decades [00:48:50] now inside these different. Tech power centers. And you mentioned a lot of them, you've talked about the series A gap. Speaker 14: What are some other blind spots that [00:49:00] you're building cherry rock to fix? And how are you planning to invest differently than some of the old guard, the old traditional firms? Speaker 13: One of the other blind spots [00:49:10] is what resources do you provide when after you provide the capital? Okay. And you know, there's a lot of large firms that have. Speaker 13: Huge [00:49:20] teams that can do these kinds of things. But at the end of it, it's the conversation with the founder. That's often the most pivotal [00:49:30] moment for them. So one of the resources that we provide is coaching. We're calling it coaching. Oh, nice. But it's really being an [00:49:40] ear and a trustworthy ear for the founders that we back so that when they're making those hard decisions. Speaker 13: They may not always do like [00:49:50] we just discussed. Speaker 14: Right. Speaker 13: Decision A versus decision B. Speaker 14: Yeah. Speaker 13: But we're willing to put it out there and tell you decision A is the right decision [00:50:00] and if it takes you a while to get there, that's okay. Mm-hmm. Because you got there. Mm-hmm. And so we wanna be that hands-on firm that's there to listen. Speaker 13: We're gonna [00:50:10] say our piece and provide the. And we're not gonna just let you do whatever you wanna do 'cause you're the founder and you can go anywhere and raise your money if you don't want [00:50:20] our help, don't take money from us. Speaker 14: Yeah. Speaker 13: And we're not gonna chase you for that. Mm-hmm. Because the returns will come when we partner together. Speaker 13: [00:50:30] From our perspective. Speaker 14: So looking back on that note with founders, what are some of the lessons that you learned from Google, from TaskRabbit, from SoftBank, that kind of shape the kind of [00:50:40] founder that you're backing today? Speaker 13: Hmm. Well, just growing up, the resilience and the grit, it shows up in different ways. Speaker 13: For people who come from backgrounds [00:50:50] like mine, we don't have the same story of dropping out of whatever we couldn't drop out. But just because we didn't drop out doesn't mean we don't. Have resilience or grit, [00:51:00] we just couldn't drop out because somebody paid for us to be here and broke their backs to get us into this school. Speaker 13: So we are staying. Mm-hmm. But that doesn't mean we are not gonna be a [00:51:10] great founder and entrepreneur. And so I'm looking for that. Google was all about moonshots and aiming for the [00:51:20] moon. And when you scored 70% on your OKRs, that was a success. Right. It debunked like we gotta do a hundred percent. We have to get to perfection. Speaker 13: We actually just have to aim [00:51:30] really high. And so we're looking for founders who can do that. And then at TaskRabbit it was all about connection with people. Mm-hmm. Who are the people that you bring around [00:51:40] the table? Leah, you did a fantastic job of bringing me in and other people and just mm-hmm. Taught me so much about how to build a great team and [00:51:50] what's important about a great team. Speaker 13: And so when I look at. Small companies, and they have, they don't have 60 people yet. They have like 13 to 20 people. Yeah. Speaker 14: [00:52:00] Right. Speaker 13: Like, do these guys have what it takes to build a great team? Speaker 14: Mm-hmm. Speaker 13: What's the founder dynamic? How are they working together? Is it gonna be, [00:52:10] is it gonna blow up and be something crazy because they can't get along? Speaker 13: Or do they have mm-hmm. A way of working together? Are they open to feedback? Speaker 14: Mm-hmm. Speaker 13: When I [00:52:20] tell people the story about why I joined. TaskRabbit, I talked about how you were ready for me, you were ready for a [00:52:30] COO and for a partner to come in. Mm-hmm. Yes. And so when I desperately ready, you were desperately ready when I talked, I, I need to see if they're self-aware because [00:52:40] now need to hire a head of revenue or head of finance. Speaker 13: Mm-hmm. And are you ready to let go of the things that you were doing to let someone better than [00:52:50] you? Speaker 14: Yeah. Speaker 13: Do that job. Speaker 14: Absolutely. You said something in the beginning of this conversation that I wrote down because it resonated so deeply, and that was [00:53:00] you felt this responsibility. Mm-hmm. And I think we were talking about education, right? Speaker 14: Yeah. And you felt this responsibility to do well, and you know, I certainly feel that [00:53:10] too. Particularly post TaskRabbit, right? We've had the success, we scaled, we sold the company, we've moved on to other things, right? And now I have this sort of deep [00:53:20] sense of responsibility of being, of wanting to be able to elevate these other stories and founders [00:53:30] and people and capitalize them. Speaker 14: And you know, it just what you're doing with Cherry Rock. Is so powerful [00:53:40] because you're taking all of your experiences and all your background and you're bringing it full circle and you're taking that responsibility and you're [00:53:50] saying, you know what? I believe in you and I'm gonna help you and I wanna work with you. Speaker 14: I just think that is so powerful and so [00:54:00] important and we just, we need more of that in the world in general, that responsibility. Speaker 13: If we do this right, we will change the face of wealth creation. Mm-hmm. And when I [00:54:10] look at the through line of my life, it's always been about how do I create more economic opportunities for people [00:54:20] who wouldn't otherwise have them? Speaker 13: And it's what drew me to TaskRabbit. Think about it all the job creation that we Speaker 14: Yeah. Speaker 13: Facilitated with the [00:54:30] platform. With Cherry Rock, we're enabling entrepreneurs to build incredible businesses that will impact the employees that work for them and [00:54:40] the communities that they operate in for decades to come. Speaker 14: Yep. You have built teams that lead with empathy and industries that [00:54:50] really prize efficiency overall. What's one leadership precedent you hope the next generation refuses to follow? Speaker 13: Oh [00:55:00] man, this is gonna be really controversial, but this whole like work 24 hours a day, I just hope they don't do it. [00:55:10] It's a trend now. Speaker 15: Mm-hmm. Speaker 13: You know, everyone's back in the office and working six days a week, seven days a week, and you know, this is how we have to. [00:55:20] Scale and build our business. And on the other side of that is, you know, lots of health challenges when you look at the health challenges that people over [00:55:30] 30 are encountering mm-hmm. Speaker 13: At a much more rapid rate than in the past. Some of it is probably just the fact that [00:55:40] we need to sleep more. Speaker 14: Hmm. That resonates. Sleep is so important. It absolutely can change everything. It changes your cognition and your help. Everything. Yeah. I [00:55:50] love that. So if your story becomes someone else's permission slip, maybe a young black girl from Detroit who sees herself in you, what do you [00:56:00] hope she learns about breaking precedent from the way that you have done it? Speaker 13: Yeah, I hope she learns the value of [00:56:10] becoming. Who you really are and Grammy sending me out to stand up for myself. Speaker 14: Yeah. Speaker 13: And [00:56:20] showing up when, Ooh, we did a really scary thing by changing our business model and people were not happy, but mm-hmm. We [00:56:30] knew in our heart and soul what we were doing was right. Speaker 14: Mm-hmm. Speaker 13: The more you become who you really are, the more in touch you are with. [00:56:40] Your soul and what's right and what's true for you, and then you break precedent. Speaker 14: So good. I love it. I love it. Well, Stacy, [00:56:50] thank you so much for coming on and having this conversation. It's been so much fun and I'm so grateful. Speaker 14: Just that Me too. You're in my life. You're a dear friend. [00:57:00] We've been partners and we continue to just build alongside each other, so thank you for that. That was Stacy Brown Philpot, a leader who's [00:57:10] rewritten the rules at every stage of tech's. Evolution from Detroit's grit to Google's growth to TaskRabbit's reinvention. Speaker 14: She's shown that breaking [00:57:20] precedent isn't just about disruption, it's about designing systems that work for everyone. And now with Cherry Rock Capital, she's doing it again. [00:57:30] Re-engineering how capital itself flows. If you know someone who's redefining the rules in their own field, I wanna hear their story. Speaker 14: You can send me a note on my website, [00:57:40] breaking precedent.com. Until next time, I'm Leah Sullivan.