Leap Academy with Ilana Golan - The Remarkable Story of Stacy Brown-Philpot Outgrowing Her Circumstances | Ep. 174

Episode Date: October 13, 2026

Founders and executives: Stacy Brown-Philpot traces her path from Detroit to Google, TaskRabbit CEO, and a $172M debut venture fund.Stacy spent nearly a decade at Google, growing from a 14-person team to leading over 1,000 people in India. She later became CEO of TaskRabbit and sold it to IKEA after launching it into four new countries.To build Cherryrock Capital, she met 366 investors over two years and closed 83 of them, including Goldman Sachs, JP Morgan, and the Ford Foundation. Her core advice: find the investor who fits your stage, then ask how they will help you win.LinkedIn: https://www.linkedin.com/in/stacyphilpot/Cherryrock Capital: https://www.cherryrockcapital.com/#VentureCapital #CareerAdvice #WomenInVentureCapital #FirstTimeFundManager #StacyBrownPhilpotLeap Academy helps professionals reinvent their careers, build portfolio careers, land board seats, and grow executive leadership skills through expert coaching, personal branding, and career development strategies. Founded by Ilana Golan, it's where bold professionals come to grow.Start with a free strategy call: https://itl.ink/leapstrategycall🎓 Watch the free masterclass on building multiple income streams: https://itl.ink/leap-webinar👇 Like what you see? Comment below and let us know what resonated!---------------🎧 PODCAST | Leap Academy with Ilana GolanInspiring, unfiltered conversations with leaders and professionals who broke the mold. Learn how to build your reputation, impact, and income on your terms.▶️ https://www.leapacademy.com/podcast---------------📲 Connect with Ilana:Facebook ▶️ https://www.facebook.com/IlanaGolanLeapAcademyLinkedIn ▶️ https://www.linkedin.com/in/ilanagolan/Instagram ▶️ https://www.instagram.com/ilanagolanleapWebsite ▶️ https://www.leapacademy.com/🧠 Produced by APodcastGeek: https://itl.ink/APodcastGeek

Always be a learner and always focus on your education, regardless of what your circumstances are. You can always learn something. That's Stacey Brown, Philpott, founder of Terry Rock Capital and former CEO of TaskRabbit. But behind that career is a lesson Stacey learned long before Silicon Valley or Google. I had reached a point where I had accomplished so much there. Wait a minute. Where's my learning? And this goes back to my childhood of always learning.

new things and finding new things to learn. So I decided it was time for me to move on. So what do you do when the thing you worked so hard to achieve becomes the thing keeping you comfortable? In this episode, Stacey teaches us how to recognize when it's time to make your next leap. How to keep growing when you're already successful. How to lead through decisions that don't go to plan and how to turn everything you've learned into an opportunity

to create something bigger than yourself. I'm Ilana Golan, and this is the Leap Academy podcast. Hey, before we start the show, I have a small favor to ask. One of the biggest things by far that you can do for us, and it's going to take you less than a second, is to click on that like, subscribe, download buttons right now. This helps the show continue to bring amazing, amazing guests, and this small act of kindness right now will,

make a massive difference. So can you do that? Really, really, really quick right now. Just click that like, subscribe, download button. And I promise I will personally make this the best show that I know how to make. And you won't regret it. Okay, now let's dive in. Stacey, I'm so glad you're here. Thank you for having me. So I'm going to take you back in time. And I want you to tell me who is Stacey in Detroit? How does she grow up? Like, paint me that vision. Wow. You're taking me way back. I grew up on the west side of Detroit, as you mentioned, and a lot of my childhood was just navigating life. We had a house at one point with four generations of women. It was me, my mom, my grandmother, and my great-grandmother. There were seven people who lived in that home. And my brother was there, my grandfather at one point, and my uncle was also there. And so we just, It was busy, and I was the youngest. So I grew up as the youngest.

I was also the baby of like the family, the girl. And so protected a lot by my big brother. We get along very well now. We definitely had our early years when we played together. Teenagers was like, you know, we go our separate ways. And then we came back together. So we're very, very close now. It was a community that we lived in.

A lot of people on the block that we lived in that I lived on took care of each other, looked out for each other. We had block parties in the summer and fire hydrants bursted and like we would run through them and then the winter was very cold and we'd get out there and shovel snow and sometimes my brother and my uncle would go down the block and try to make money shoveling other people's snow. I never really had to shovel snow because I had a brother and an uncle who did. And so that was, I was lucky to be the youngest, I guess, in that respect. I grew up with pets. dogs on my life and I love animals. So yeah. Oh, me too. We just had to put down our dogs. So that makes me really sad. I've been through it. That's our heart. I'm so sorry. Thank you.

But when you grow up like this and you started working kind of early on and and hassling and doing my thing, what do you feel it taught you now when you're looking at retrospect, what do you feel are some of the big lessons that you were taking with you? One of the things. One of the things. One of the things I learned growing up was the value of education and my mom always talked to us about the importance of learning and what you learn no one could ever take away from you. And so always be a learner and always focus on your education regardless of what your circumstances are. You can always learn something. And so I've always taken that with me and you can look at the world today and see how fast the pace of technology is accelerating. But if you're a learner, it's exciting.

It's not scary. There's nothing to be afraid of. If you know how to learn, you know how to adapt to what you learn. That was something that we were taught. We were always taught to adapt to our circumstances, never let your circumstances define you, but understand what they are and figure out, you know, how to make a way. And then we talked about, we were taught about community. And the community that you are in, your job is to play a role in that community and uplifting that community. And teaching my kids to be productive members of society as parents, that's sort of what we're supposed to do. And we were taught that if there's someone else who's hurting, you're hurting, and what can you do to help that person? So those are some values that I grew up with

that I've taken with me throughout my life and try to teach my children too. Yeah. And I love these lessons. So first of all, just tap into that adaptability. I mean, I think, think today, we're going to still go through your story, but if we jump into today, I mean, the world is all about adaptability right now. And adaptability, if you think about it, it's learning, right? It's learning, experimenting really, really fast. So this is for the listeners, like, you're going to need to just be, like you said, a constant learner. This is not about, there's not going to be one career ladder that you can just climb and chill. Like, you're just going to need to learn all the time. But I also love the community part because I think

when you are part of a community, you understand that there's something greater than yourself. Tell me, like, you know, at some point, and you went to some incredible schools, but, you know, I think, you know, and correct me if I'm wrong, but I think one of the pivotal moments for you were also, like, when you had to go to Google India. And to me, that was fascinating to read about it because that sounds so far off and why would you say yes or et cetera. So, but take me to that, take me to the journey until Google India and what made you decide to say yes to this adventure. Well, going to Google India wasn't the first time that I was sort of taken out of what was a normal environment and dropped into something completely different.

When I left Detroit and went to college at Penn, I went from a community, a neighborhood that was mostly black to an Ivy League school that was not. And so, you know, 98% of the people I interacted with looked like me. to, you know, I think Penn at that time was six or seven percent black. So that was the first fish out of water experience that I had and I got there. Take me there for a second. Yeah, I want to hear more about this. Yeah, it was just shocking. I was ready for a city that was Philadelphia because I grew up in a city of Detroit.

So I was ready to be in a city and I understood what an inner city was. But I wasn't ready for that culture, shock of just getting to know people that didn't look like me and didn't come from different, you know, didn't come from the same background that I had, different faiths. My roommate was a Jewish woman and she was so sweet and so kind freshman year. Her mom would bring her food and I would, she would bring enough for me. And, you know, I got to know, okay, a lot of Jewish people like to provide food and they provide a lot of food for everyone. We love food. That's like, that's what we do too. We have a lot more in And then we think. It was great. And so that is an example of how I learned. There's a lot of things that are different about how we might look, but our lived experiences are very similar. And it opened me up to that world. So I did find my people at Penn. I joined a sorority Delta Sigma Theta and those women became, you know, lifelong sisters. Was there two sides to this? Was there a good side and a bad side too? Or was it only, could you see only the good side? Like,

Did you feel? I wouldn't say bad side, but there were challenging sides. Like, it was a time when we, when you start school, there's sort of the activity fair. And you walk around and look at all the different clubs you can join. And I was in Wharton, so I was studying finance. And so I wasn't going to join that many activities because it was a very rigorous program. And so I'm walking around with the people from my dorm who looks like, you know, America, lots of different races. And, and I'm. And so I'm walking around with the people from my dorm who looks like, you know, America, lots of different races. And, and, and I'm walking. And And I walked past the cheerleaders and they were handing out flyers and they didn't give me one. They like gave the girl in front of me one. They gave the girl behind me one. They didn't give me one. I was like, wait, what's wrong with me? I don't want to be a cheerleader. I was actually a major at in high school, which in my opinion requires more skill because

you have to actually twirl a baton. But, you know, I debate with the cheerleaders that they want about which one's harder. If you're doing flips, maybe you can compete with me. I don't know. But anyway, they never even consider that. Like I actually could do. I was on the Pompom Pond Squad. I could dance.

They didn't know that about me. They just passed me over with the flyer. And I don't know if it was racial or not, but it was definitely like a moment of like, whoa, that's never happened before. And that was, you know, it was sort of like an awakening of what life might be like at Penn and how people might see my color in a different way. Warden was a very rigorous program. It was very challenging, very hard.

And I worked harder there than I worked anywhere up to that point. And, you know, I think today, even, I think students work so much harder than I worked when I was in college. And I wasn't really prepared for how competitive it was going to be and how difficult it was going to be. But I was able to rise to the occasion, but it was certainly quite rigorous because they grade on a curve. I don't know if they still do. So you're really struggling to get that A because that's who gets the intern. and all of these things that create, you know, unintended consequences, I think. And obviously that opened some amazing doors for you. But take me there, like, until you got to Google, what, you know, a little bit of that journey. And then, you know, what happened in Google? Yeah. So I left Penn and I went to work in public accounting. I studied accounting.

I took an accounting class in high school. And that was what got me interested in business to begin with, focus. focused on accounting at Wharton and graduated and went to work at what was Coopers in library, which became Pricewaterhouse Coopers, and got a CPA. And I thought that's my path. That my path was going to be public accounting. I was going to be partner in a CPA firm. I wrote a book about accounting, a study guide. I was just, this is, this was my world. And then I applied to business school and decided to, before going to business school, do a, take a role at Goldman Sachs working in mergers and acquisitions where I worked in New York. But applying

a business school was the moment where I realized there was a whole other world out there beyond finance and accounting. And there was this place called Silicon Valley where all these startups in 1999 were going public and it was, I don't know, weren't they weren't worth of a trillion dollars. It looked like the gold rise. I know. It looked like, but, you know, the relative equivalent of a trillion dollars. They had no revenues. It was fascinating. And I got really excited about that, and that's what took me to Stanford, encouraged me to apply and caused me to apply and also took me there. And once I got there, it really opened up a different world of technology and how technology could be used to create value and create opportunities for people. I actually wrote my essay about becoming a VC, an investor, and was on that path.

And when I entered the GSB, obviously I took a detour, and that detour was Google. And it wasn't the intentional job. Someone told me you should get some operating experience if you're going to be a good investor. And I had been president of the Venture Capital Club. I had a summer internship in VC. But I didn't know what operating experience was. I'd been in public accounting.

I'd been an investment banker. So I said, okay, I'll go to Google and get this thing called operating experience. Well, that turned into an almost 10-year career. And my first job was in finance, and I moved out of finance into operations. And while I was in an operations role, I went from managing 14 to 200 people.

I was sort of building the organization. Google grew from 1,000 to 50,000 people while I was there. And I grew along with it and the opportunity to go to India. Wait, before that, before that, before that. So take me there on a journey of leadership, right? We don't learn leadership anywhere, right? We just kind of need to scrape our knees, essentially. I don't know about you,

to just scrape my knees. And then, like, how do you learn or how do you mature to be able to lead such a big organization? Like, what do you feel like what are some of the lessons that you learned on this journey? It was a lesson in management. I, my first team grew to 14 people. And that was, you know, I was not the doer of everything anymore. I even learned that in public accounting.

I learned not to micromanage. I learned to sort of hire great people, people who could do many, many things, especially when Google was growing so fast. You have to hire people who can just take on a lot of stuff. And you have to hire people who are smarter than you. And so I built this team. Fourteen were tight. We knew each other. We knew all about each other's lives.

And it was fun. It was exciting. And then I got tapped to run a bigger team in operations and leave finance, which was a function that I knew well. I've been an accountant, an investment banker, I knew finance, moved out of finance into operations, which I did know the function. I was going to manage 200 people. And that was a big step. I was changing functions and I was changing the way I had to lead.

So you go from sort of managing individual contributors with 14 people to managing managers. And that is a step function difference of how you interact with them, what kinds of things you talk about. A lot of the role becomes strategy. and less about execution, more about strategy, less about direction, more about people, so many one-on-ones with people and all the stuff that are going on. And I did get to know all 200 people, but not as close as the 14, because they were spread across different offices and we couldn't all have an off-site, you know, three times a year or four times a year. We got together once a year. And so it just changed the dynamic of

going from managing individual contributors to managing managers and how you have to focus more on strategy. So then I get to India. Before that, like, two things. So first of all, I'm curious, was there, do you feel like there was like some mistake? I think we learn a lot for mistakes. Like, do you feel like there was some mistakes that you've done that you remember, like vividly? You're like, okay, I'm not doing this mistake again. But this is something that you remember in leadership? Well, there's a couple. One is I worked with Cheryl Sandberg really closely at Google, and she would say to me when I was, before I moved into the operations team, you know, you have to hire, have you hired your replacement? You can't move on until you hire your replacement. I kept hiring people who were very good at what they did, but were never going to be the people who would take my job someday. A lot of times we think, oh, if I hire somebody who can take somebody who can take me, my job and they take my job, then I won't have a job. But in order for you to move on and grow and get promoted and change roles and all and get more responsibility, you have to replace yourself. You have to

find people and humble yourself to be comfortable that someone's going to come in who works for you, who probably knows more than you about something or will be better than you at something. And that was a humbling moment, a humbling experience that I had to learn. And she was just beating it into me. Like, when are you going to replace yourself? How are you going to hire you? And finally, I did hire my replacement. And then the opportunity came up to take on this 200-person team.

There's no way I would have been able to take it on if I didn't have somebody who could step into my role. Incredible. So before we go to India, what is it like to have somebody like Cheryl Sundberg as a mentor? Oh, well, she's a friend. now and we mentor each other. I mean, it kind of goes both ways. It's, it was intense. I remember leaving meetings with her and she would, she would just pull me aside and tell me like the three things I did wrong in that meeting and the way I should have positioned something. So I was always anxious when I left because I was like, oh my God, I'm about to get some feedback. But feedback is a

gift. And I actually learned that that immediate feedback, you can improve right away. You didn't save it for like the one-on-one or the performance review. Just like pull that person. And I trusted her and I know she cared because I was trying to get some budget to start the Black Googler network. And she, I sat down with her and I said, look, you started women at Google. So can I, you know, have you helped me be my sponsor? And she's like, no, Stacey. Like, you are it.

Like, you are the person. I'm not black. You've got to go do this. And she's like, I'm going to help you do it. But here's how we did it. and she helped me set up meetings and she would help review my materials. And then, you know, I was trying to write an email one time

and she called me to her office. And the email was like a very senior vice president person in the company. And she's like, Stacey, this email is way too long. It was like five sentences. I said, it's not. She's like, no, we got to tighten it. And so we tighten it to three sentences.

He's like, do you realize how many emails this person gets? And I said, yeah. And he's like, do you think they have time to read them all? I said, no. And you're like, you want them to read yours. We got to tighten the email. I just, so she was, she pushed me, but she cared. And that I loved about her.

Oh, that's incredible. Incredible. And I think it's so powerful to have somebody like this that actually cares and will take you and lift you. And amazing. So, okay, so eventually somebody comes to you with this idea of Google India. And it's a very different environment. Like I traveled in India multiple times. I just came back from cycling with Richard Branson.

and Sarah Blakely and a bunch of others in India. But like, I love it, but it's very different. So you say yes to this. Why? We needed a leader in Google India. And we wanted a permanent person to live there. But in the interim, someone had to go run the office and then hire that person who was going to be the long-term person

that lived there and took over running the operation. I had now been leading my 200-person team for a while. I always wanted to live abroad. And working abroad was interesting to me and hadn't quite said, okay, I just wanted to live abroad. I love travel. I love visiting other countries. I love other cultures.

And can I put a bracket here like living abroad and living in India? It's two very different things. It is. It is. And no one really understands that unless you've been. Right. What I loved about India, I'd been before. So I'd been over there as we were building the office. I'd been a few times. We were building a major office in Hyderabad. We were building a major office in Dublin, Ireland. And so I'd been to both of those places. And definitely like India has its own unique culture. But I loved Indian food. And I just thought the people there were special. So when they came, my manager came to me and said, hey, we want you to go to India. We really think that you'd be a great person to leave the office and help find your replacement who was going to be there for the long term. At first I said no because I just was like, wait, I don't think I can do this.

My husband and I were thinking about starting a family. And I just said no. And then I go home and Chris is like, well, why wouldn't you? Haven't you always wanted to live abroad? Like what better way to do it if, you know, this great company that you work for is going to pay for it? And I said, all right, I can do that. You're right. So I went and I said, okay, if I do this, here's what I need to make it work.

And we talked it through and I went. And it was just this dream that I had to live abroad. And I'm at Google. I'm like, they're going to take care of me. And it's a short term assignment. I stayed there for one year. And I didn't have kids at the time. I was married, but I didn't have kids.

so it made it a lot easier to make that decision. I didn't have to move my whole family. And so I took the job. Incredible. So talk to me about this because there's a big, like, I love India. Again, I go there every few years. I brought my family, et cetera. But it is a culture shock.

And there's also like, you know, there's a little bit, I mean, tech was anyway kind of male dominant. There's like a lot of things that might make this a little harder. What was it like for you, this new environment? On the one hand, I'd been before, so everybody knew who I was in the Google office. So I felt, wow, like this is amazing. On the other hand, I was this rare thing, right?

This woman, this black woman. People were like, are you like Ursula Burns? Because she had just been named the CEO of Xerox. And I actually just met Ursula like three years ago. This was so long ago. I told her this story. I was like, thank you. Because no one had like a frame of reference for how to think about me.

And, you know, my gender mattered because it was fairly male dominated and showing up as a woman. You know, they often deferred to the men. We would go out to dinner. And then they realized, oh, this is, she's in charge. And then I became madame. And then I was the one in charge. And things like that would happen. And then you're in a place where there's a lot of help and support.

So people were doing things for me that I was raised. I'm from Detroit. We were raised to do things for ourselves, clean up, all these things. And so I had to adjust to that lifestyle. And that was really interesting, too. And then from a leadership perspective, I went from managing 200 to over a thousand people. So then it becomes about inspirational leadership. You're not just managing managers.

you're leading leaders who are managing managers. And you don't get to know everybody. You can't know everybody's name. And you learn that repetition doesn't spoil the prayer. You have to say things over and over and over and over again because the person who's hearing it, they are hearing it for the first time or the second time or the third time, even though you've said it 300 times.

And that's a different kind of leadership. I remember halfway through, almost halfway through my time there, we had a big talent show and conference and event. And it was a, you know, American Idol type thing where people were going to, you know, perform and there was going to be judges. And I like, Stacey, you're going to open the show. And I was like, okay, you're going to do a dance. We're going to teach you a Bollywood dance. It was like the most famous.

Don't ask me what the song is now. I'm too old to remember. But it was like the most popular song at the time. And, you know, you're going to learn this dance and you're going to perform this. dance to open up the show. And so I had rehearsal, you know, every night for like a couple of weeks, a few weeks, so I could learn this dance. I had like an outfit. Oh, you're such a good spirit. Oh, my God. But that's inspirational leadership. I get there and no one knew this was happening. Like, oh my gosh, she's like performing. So, you know, that's the definition of inspirational

leadership. And so the things that you do, the little things kind of matter just as much just the vision and the strategy and the execution, all of those corporate messages, but it's sort of how do you touch and reach people. That's how I ended up doing the 5K. I get there and the HR team is like, oh, we're really trying to focus on healthy lives, people smoke too much. And so can you help us like, you know? And I said, great, what is it? We're going to challenge everybody to join a 5K. And I wasn't, I was like a short distance runner. I was not like a long distance. runner at all. And I was encouraged to do this 5K. And I said, it's only like three something miles.

I think I can build up to it. And I was training for this thing and traveling and running. And I didn't anticipate the air quality, the heat. None of those things was part of my training because you're training like on a treadmill, you know. And so anyway, you know, these are the things that you do. I won for my age group. Let's go. But I just, you know, these are the things you do when you think about inspirational leadership, some of the things that have nothing to do with the job. So good.

But I love that you were calling it inspiration leadership. I don't know if I thought about it that way, but in the end of the day, as a leader, you want the following, right? Like, you don't want people to come to you because of your title. You want them to follow because they're inspired. follow and I think that's a very different distinction. So was all of that, which just sounds like an incredible experience, why did you decide to found like the Black Google network? Do you feel like there was like specific situations where you felt like, you know what? Like I want to stand up for.

Like what was it? What was the motivation? I was fine at Google. But it was also a great great place to work. And I looked around and there just weren't a lot of people that looks like me there. My people should be here too. This is amazing. And this is when free food was new and innovative. Oh, we were so jealous at you guys. This company that's doing all these amazing things with free food, you could bring your pet to work. I was negotiating with my husband to get a dog, worked at Google, got the dog, bringing the dog to work. What is this? And I just wanted more people that look like me to experience what I was experienced and have the opportunity that I had. And that was now I started the Black Googler

Network and it grew to become, you know, one of the more seminal affinity groups at Google and a model for many others that that followed afterwards. We really changed a number of really important things in terms of how recruiting was done. We weren't recruiting at HBCUs, historically black colleges and universities, for example. And because of the work of BGN, they started recruiting at those schools and realizing there's a whole population of talent that we are not touching because, you know, certain schools weren't on our recruiting docket. We hosted a number of events and, you know, brought leaders to have conversations with us. I remember we had Magic Johnson one time.

And, you know, he went, and Larry is from Michigan and went to Michigan State. And that was an amazing, like, meeting between the two of them, because both of them were, like, fanning each other. And everyone is like, how is, how is, like, Magic Johnson, like, fanboying Larry Pay? Like, it was just, it was incredible. And so there's just a lot that we did there to just introduce. culture in many, many ways to different people. And it just, it meant a lot to me because it just helped me feel more at home because I had people that shared, had shared experiences that I had working in a company that I loved.

Oh, that's so profound. That's incredible. And it's interesting because I feel like in Israel we grew up with like every single race color on the planet. And I don't think I think I was blind to it until I came to the U.S. And I think somebody asked me like, what, you know, I don't know, what's your race or ethnicity or whatever? And I put Asian and she's looking at me and she's like, you're not Asian. I'm like, I swear, I was just, I'm like, that's all I.

You know, I was like, no, no, no, you should you should put white. I'm like, this is so weird. Like, most of us are not white actually. So anyway, it was just like it was a. So, but tell me a little bit about that. that move, by the way, from India to the U.S. Because that's, again, this is another culture move as it is. Did you feel like it was easy for you?

So getting there was like adjustment, culturally adjusting, particularly around how decisions get made and how things get done. They were very much like people, people. So I would have one-on-ones that were 45 minutes, 40 minutes of just talking and five minutes and doing stuff, right? Like it was, I was like, all right, this is, this is how things get done. And that's a, that was a switch between my very efficient Silicon Valley conversation. It was like 30 minutes and you're in and hour.

Here's my action items. It was very different. So when you come back, you have like a reverse culture immersion. And I had to sort of adjust to some obvious things. Like, I will never eat Indian food the same in this country. because they don't have the spices and there's certain things you can't get like the mangoes, for example.

You cannot bring mangoes from India. Like they can't leave the country. So you can only eat the mangoes there. And they're like the best mangoes. So there's some things you just can't get. So it's like reverse immersion, like coming back. What am I missing? How do I adjust?

Also the pace of life, it's like things just. flow, you know, there's a four-hour dinner and that's super natural. It's normal there to have a four-hour dinner. We get there. We talk for a while. We have some appetizers. 930, 10 p.m. Now it's time to eat dinner, right? It just flow differently. And I come home and it's like, all right, 630. You know, your kids have to go to bed at 7.30 because it's like you're on the schedule. You had to get used to that again. And then from a leadership perspective, I was halfway around the world. So most of the time, decisions got made while everyone in Mountain View was sleep, right? They is at the trust that I made a good decision.

And you come back and now you're here and you're in the belly of the beast, which is corporate headquarters and there's a lot of sort of cross-functional work that can be done real time. And that's a different mode of operation too. And I had to reintegrate into that. Was there elbows that you needed to learn a little bit? Like how to, I don't know, just kind of maneuver your way. in the headquarters, like, talk to me a little bit about thicker skin elbows, like some of that.

The elbows happened when I went to India. There was, you know, I was managing other functions like facilities, which was in charge of bringing, you know, people to and from work. We had cars that would transport them. And I thought I could send an email and say, hey, you know, there's some questions about how the cars work, you know, here's some action items. Please take care of it. Thank you. And nothing happened. And I said, wait, okay, I actually have to go and, like, go to this person's office and sit down and walk through and be very clear about what needs to be done in a different tone. And that wasn't how we did things in Mountain View. It was different. So that was sort of one piece. The other was when I came

back, the company had grown. It was even bigger, right? And reorgs were kind of every 18 months. People would get upset because they got moved. And I would say, don't worry. This company is so big now. In 18 months, you'll have a different boss. You'll be in a different floor and a different building with a better cafeteria. So you don't have to walk to it. And inevitably, like every 12 to 18 months or so, like there was kind of a reorg. Which makes sense. sense. We grew from one to 50,000 people. Like, you have to re-org. You can't just let it just bloom. You've got to like trim and, you know, all kinds of things have to happen in building a company. So when I came back, I was sort of coming back into the next reorg. And functions had moved around.

People had moved around. And there was new relationships that I had to build. And Google was never an elbow place. Like, not when I was there. I left, you know, and at the end of 2012, beginning of 2012, beginning in 2013. And it was it was never a elbow kind of place. It might be that now, but I'm giving you in my era. There were never sharp elbows. Like people were reasonable. Everyone believed in the mission. We all were kind of here to do something that mattered. And they were willing to sit down with you. Now, you did have to advocate for yourself and influence without authority and all of those things that go along with being a part of a big company. Every big company has that. But were never really any elbows.

That's amazing. So tell me a little bit about how did you get to TaskRabbit. Like, what was the path? I was ready to leave Google. It's hard. You break up with like a really good boyfriend. I mean, it's such a safe, wonderful place to be. But I had reached a point where I had accomplished so much there.

But I was feeling like I was plateauing. I become a sage. Like, everyone was like, what is, you know, something. to happen. Can I do this? Oh, ask Stacy. You know, she knows everything. And I did. And so, wait a minute, where's my learning? And this goes back to my childhood of always learning new things and finding new things to learn. So I decided it was time for me to move on. And I ended up going into work with Google Ventures. And GV was just starting at the time. They were building. and launching the new venture firm.

And I just wanted to hang out with them. I went as an entrepreneur and residence. I wasn't going to start a company, but I knew so much about Google that I could help portfolio companies work with Google. I could sort of see what's out there. And that's how I found TaskRabbit. I had met the founder of TaskRabbit

before I went to Google Ventures. And fast forward, 18 months later, I was in her building, visiting another GV portfolio company and saw TaskRap was there, sent her an email, I said, hey, I'm going to be here a couple days a week. And I'd love to have lunch. Had lunch one time. She said, hey, we're looking for a COO. And I said, I don't want to drive to San Francisco. I'm good. And I had a baby. I had Emma. I said, I'm good. And then she said, no, no, you really should. And I decided to join. That was it. A few more meetings later.

amazing and I want to all the listeners to hear this because we talk a lot about the hidden market like at the end of the day these kind of roles only happen because somebody knows somebody or because you put yourself out there and was very clear what you're good what you're good at it's not the job boards it's not the typical thing like you need people right to open these doors for you so and that's incredible so and you started task rabbit as a COO but then you moved to be their CEO. So talk to me a little bit about, because I do believe there's a big difference between CEO and any kind of other role. Can you talk to me a little bit about like some of the things that you learned and also you joined some boards and I want to like, I think they also prepared you for what is it like to be CEO? So talk to me about that journey, Stacey. Yeah. The CIO job is, and I think about this job a lot because everyone wants a COO, but there all different. And my role as COO, functionally, I was responsible for everything except product and engineering. So for me, that was marketing, ops, finance, legal, customer support, anything

there. And then we built the data science team and that ultimately reported to me. It's also about how you sort of, the train is running as fast as it can. And my job as COO is to see the roadblocks, see the obstacles and move them out the way so that we can continue at this pace. And part of that meant putting in processes and sometimes it meant taking away processes and sort of knowing the difference between you. And then the third piece of my job was being this thought partner with Leah as she was growing the company in vision, strategy, presenting to the board, organizing board materials, things like that, fundraising.

And stepping into that role, I had led. had a lot of functions, operations and finance at Google. So I'd had financial expertise. I had expertise across some of the functions I was responsible for. But I'd also seen scale. I'd also seen what it looks like to be, you know, a $100 million company. She had never seen that before. So I knew how to think about scaling fast and I could scale the company in the right way. And that was my job. And in the process, I joined the HP board. As you mentioned, I did join some boards as C-O-O-O. And when I joined that board, it was an opportunity for me to, I was looking around, okay, you're C-O, CEO, and then there's the board. I want to join a public company board.

And so I was able to get a role on the H-P board. I'm happy to talk more about how that happened. But that helped me see, what does it mean to be a good board member? Let's go there first. second because I think a lot of our listeners are executives and trying to figure out like advisory board seats, et cetera. For me, the first public boards was a shock because it feels very different. But it's also only hidden market. Like nobody's going to just kind of like randomly post something. I need a board. Right. Like so yeah, like take me there for a second. Like joining that board. What did you learn? How did you get there? Et cetera. Yeah. Joining the HP board was it was a hustle. I think, You know, if there's anything I learned in my childhood, it was like how to hustle. But I told everybody that I know that I wanted to join a public company board. And I sought out people who were on boards and asked them, what did they do? Well, we met these recruiters. Okay, I want to meet these recruiters.

And at the time, there were a couple of recruiters who were focused on helping more women get on boards. And, you know, some of those initiatives are now baked into every, recruiting organization, but it was early. Those were some early days of some really strong women leading in this direction. So I met with them. And then I sort of put together a board bio. I got advice, oh, you should put together a bio. Okay, what's a board bio? Which is different than your resume. The resume is like, what did I do? I achieve these goals, these revenue goals and look how great I built this company. The board bio is more about how you, how what you know is important to what another organization might care about.

And that's a different way of framing your set of experiences. So I had my bio, I had my sort of list, I had the recruiters, and I was just telling everybody that I know. And I told somebody at a conference, I was just at a conference in the bathroom, honestly. This other woman, we were washing our hand. He said, what do you have to say, you know, I'm interested in public? the company board like one day. And he said, oh, great. If I ever hear of anything, I'll let you know. And she referred me to the recruiter for the HP board. And that's how I got on their list.

And then Meg Whitman was the CEO of the combined company at the time. And HP was splitting into two. So there were a lot of seats available. That was helpful, right? I wasn't just competing for one seat. That was helpful. And I had met her at another event. I didn't know that I would ever see her again in life, but I said hello, introduce myself, and everyone sort of moved on. So she knew of me. All those touch points matter.

And people ask, well, how do I get on a board? Well, you've got to have multiple touch points out there and then a little bit of luck, right? And a lot of preparation. I love it. And then how did that prepare you? Because I think at that point, you see a perspective that usually you might not see.

So how did that prepare you for a CEO role or how did that kind of form your thinking? I joined the board in November of 2015. I took over a CEO in April of 2016, so not that long after. It gave me a lot of perspective on just what does it mean to be a good board member? and what's the difference between being the CEO and being the board member? And what do you expect from a world-class CEO? I mean, at the time, I was on the board of HP. We had Dion who was a CEO.

I mean, it was $50 billion company. What does that look like? What is your job? What do you really, what does the board hold you accountable for? And when I took over a CEO, I then had a perspective now of, oh, I'm going to be a better CEO because I now know how to communicate with my board. I now know what to ask them for. And I know what they expect of me. And that changed the dynamic of what I needed from my board. We had investors on our board, which is different than it's a different kind of governance than

being on the board of a public company. But still, there was a relationship that had to be cultivated, which I had a better understanding for having been on the other side and, been in their seat of being the board member. Incredible. So before we jump into Cherry Rock, just one question. Like, I think most people when they're, like, especially when they're CEOs, like, they're going to have this moment of, oh, my God. Like, I don't know how I'm going to sleep at night.

Like, was there a moment where you're just like, oh, God. Like, how do I recover from this? Oh, wow. There's a few. I wouldn't say recover, but scary things. One, we made a big product change. And that one was I wasn't, I knew, I had a feeling we were going to recover,

but it was scary. We made a very big product change where we eliminated several categories at TaskRabbit. And as a result of that change, a lot of people, a lot of taskers, it weren't going to be a task anymore. The way you hired Taskers, clients would have to sort of accept an hourly rate instead of bid. And it was going to do something

very powerful, which is very commonplace today, which create like fulfillment and liquidity in the marketplace. But you had to accept the rate that the person wanted to charge. You couldn't negotiate anymore. But you were guaranteed that your task was going to get done. So that fulfillment was a big barrier to our growth. And we had to solve it. And we did. What we didn't do was tell people that it was going to happen. It was kind of like this big marketing reveal. People didn't like it. They were like upset about the change.

And there's like a flaming TaskRabbit logo now. I used to do a search on Google. I think it's probably still somewhere out there. I filled it so many calls. Leah and I filled it so many calls from people who were just upset with us about this change and not telling them. And our revenues did go down. We eliminated, you know, a good chunk of categories.

which meant a good chunk of revenues, and we needed to see the curve shift and go back up again. And ultimately it did. We did return to growth. But it was pretty scary to make a big product change. Take me there because I think, especially now, I am people are like frantically trying to figure out what's next. And sometimes they'll, I mean, they'll need the thick skin.

They're not sure if this is the right direction. You know, it is taking their sleep away. You're like, take me there for a second. Like, how do you manage it? How do you gap up? How do you continue motivating yourself and not just like, you know, lie in bed crying? No, I'm kidding. But, you know, like, how do you recover from that?

Because it is overwhelming sometimes. It was very overwhelming. I would do calls in the evening with clients and taskers. Like, everyone's calling me mad. And I just had to sit down. and remember we have a big mission. Like, what are we here to do? And our mission was to make everyday life easier

for everyday people. And if we don't have a business model that can generate revenue and good margins, we're never going to raise money again. And we're never going to be profitable. And we will go out of business. So then we will not achieve our mission. So I had to like just remind myself

this is the mission of what we are here to do. And we want to be a global company. In order to do that, we need to make these hard tradeoffs. Hard things are hard. And it was hard. And to sit there and sit with that, but recognize the bigger why. We also had metrics. Okay, how do we know we're successful with this hard thing that we just did by week?

And we would sit down once a week and we would look at the metrics. Are we making progress towards these other metrics that show success despite dealing with this hard thing right now? And I think just having that anchor was so important for us. And today, like now with AI and everything, everyone's trying to anchor on a lot of different things. And it's really, really difficult. But finding meaning and purpose and what matters and focusing on that can help. Oh, that was powerful. Like that, I just marked that.

That's a short on its own. And that was powerful. Okay, so take me to now you decide that you want to start something even crazier, which is a fund. And you're going back to your investment roots. And now you're equipped with investment, operation, CEO, board. Like, yeah, now you, like, now there's like, you, like, you know everything. and now you're starting a fund.

So take me there because I'm sure some people say, why a nurse would you do that? I left TaskRabbit. We had a successful sale to IKEA. The business was thriving in IKEA. We had launched four new countries. We were growing the business at a very high rate. We were a huge chunk of the business

was now coming through IKEA online and in stores. really the industrial logic of this deal was working. And so it's time for me again, I reached that point where I was, okay, ready to move on. And I just came back to the thing I said I was going to do when I came to the Bay Area, which was start this venture, like going to work in venture capital. Why do I start my own firm versus going to another firm? I really saw this opportunity to invest in underinvested founders who left access to capital. there was no capital problem.

It was just an access issue. And I had done so much with TaskRabbit, you know, that early stage, not C stage, but that $1 million to $100 million, I was super excited to just invest in the next generation of entrepreneurs. I got offered, when I left TaskRabbit, I got offered other CEO positions, but I thought to myself, why do that when I could just catalyze the next generation of entrepreneurs? And so I said I was going to raise money. It was 20, 23, and everyone's like,

this is a really hard time to raise money. I didn't know. I'd never done it before, but I figured, why not? Let's see what happens. And it took two years. It was hard. It took a lot longer than I expect it. But I think we're doing something pretty special with Cherry Rock.

Did you think that you're going to make raise $172 million. Like that is, I mean, that, I mean, as a first fund, like people will aim for 20, 30 million. Like, you went all, all in. I had some friends early on who were in private equity who raised billions. And so for them, they were like, if it wasn't at least 500 million, they were just kind of looking at me like, this is easy. But you realize that raising 50 million is just as hard as raising.

500 million. It's just, you know, it's hard. All of it is hard. I wanted to invest at series A and B, because I saw this opportunity to invest in companies and people at that critical stage where they need real capital to help them grow. My experience scaling TaskRabbit, managing global operations at Google, all of that was about scale and growth. I had board experience. I had built a huge team. So a lot of my own expertise was really at that Series A, Series B stage. TaskRabbit had raised a Series B right when I joined the company. So in order for me to differentiate myself, I needed to have an edge. And so that was my edge. Well, if I'm going to invest at that, stage and be competitive, I need to be able to write six, 10 million dollars checks. I wanted to lead rounds. I didn't want to be in a position where I couldn't write a big enough check. I didn't want to be in a position where I couldn't lead, I didn't win the lead because I didn't have enough

capital and I was perceived as not being solvent or strong enough or, you know, just great enough in this competitive market. So I needed to raise a bigger fund. I went to Wharton. I want to I built a model. I built a portfolio construction model and I said, okay, if I want to invest in a somewhat concentrated portfolio, what does that look like and back into what the minimum viable fund size needs to be? And it was at least $150 million. So it was all mathematical and strategic, like how, it wasn't like I went out and said, okay, I'm going to raise as much money as I can. I went out to raised based on a thesis that I thought was particularly important. And in order for me to execute that thesis, I needed this much money. Now, there were times when my partner, Seda, and I were like,

huh, are we going to get to, you know, the 150? And we had started investing because we got advice to get in market, like get in market, you know, get out there, show that you can do deal so that you can win, you know, so you can, you know, so you can work together. So we were investing ahead of having the full fund raised. So we were highly concentrated at one point. But it all worked out because that story did help us with later LPs who ultimately came in. And so we were able to get institutional capital from Goldman Sachs and J.P. Morgan and Mass Mutual and Ford Foundation and Bank of America. And we were able to get big family offices like Pivotal Ventures to invest in what we were doing.

And all of that changed the trajectory of how we were going to do this fundraise. But before that, Stacey, like, you needed to have the grit to, I mean, raising money anyway is hard. Like any founder will tell, you know, like knows that, right? But I think it's a first time fund, even though you've had all these accolades, like, it is really, really, really hard. So, so, but talk to me about the nose. Like, you probably got Brazilian rejections, I assume, or ghosted or whatever. Like, what, again, how do you get yourself back up when that happens? I did a talk for my daughter's high school for Career Day, and I did the math because I wanted to show them about rejection. One of the things was about

kind of rejection. And I met 366 different people or companies. And in each of those 366, I met with them anywhere from one to 10 times. On average, it was six or seven times so you can figure out how many meetings I was in two years. And I got 83 people to say yes. So, a lot of nose and each one of them you know it hurt. Of course you're sitting here and say, oh, you know, it's just business. It is just business. But I had to stay focused on the story and the narrative of Cherry Rock and what we were doing. I remember taking my daughter to horseback riding and I had a meeting. So I said, okay, I'm going to get there early. I'm going to do the meeting and then I'm going to walk her in. And she was in the backseat. And I had a meeting. And I had a meeting. And I said, okay, I'm going to get there early. I'm going to do the meeting. And I'm going to walk her in. And I was. And I I had the, you know, my phone sitting on top of the dashboard, the Zoom. And I didn't know if it was going to be a pass or not, but we were, this was like third or fourth meeting with this institution. And they passed.

And they told us why and everything and, you know, wished us all the best. Let's stay in touch. I turned around and my daughter says, oh, mom, that didn't go well, did it? And I said, no, it didn't. They're not going to invest. And she goes, that's all right. You'll get the next one. And she said that, like, she had.

hadn't been in every rejection yet, but she'd been in that one and she saw like, okay, like, Mommy can get back up again. And so I always get emotional about that because I think, you know, kids have a way of sort of bringing out the best and the worst in us. And I said, you're right. And so my attitude through those 366 is like, that's all right. I'll get, I'll get the next one. And we have a wonderful set of people who said yes to us. And I'm so grateful and thankful to all of them. And it's just an incredible mission. But what do you think is like if somebody's a founder or the listening to this,

what are some of the biggest misconceptions that people have about venture capital, you think? Yeah. It's not the dark side. So let me just say that out loud because everyone, when I told them I was raising a fund, they're like, oh, you're going to the dark side. And I was like, is it really dark over here? So I'm over here.

It's not dark. it is bright and you know we're not out to get you and I think this is a finance job that is one thing that I will say if you're a founder and you're talking to a VC and you think oh I just want to be your partner and your friend this is a finance job their job is to make money they took money from somebody else who said and told that person, if you give me this money, I'm going to make you money. And so their job is to generate a return on that investment. If they're investing their own money in this charity, that's totally fine.

But if they have taken money in the venture capital model, their job is to make money and it's a finance job. So in as much as it's not the dark side, I invite founders to remember that our job is to generate a return. And our role in partnering with you is to do what we can to help you be successful in that. At Cherry Rock, we don't just write a check. We get involved. We help you with go to market.

We help you with hiring. We help you with CEO coaching, growing up as a leader. Some of the things I talked about going from managing individuals to managing managers to leading leaders. That's a whole actual kind of physical journey, but it's also a mental and psychological journey that a founder has to go through. We help you with those things, but it is, our job is to generate a return. And so I, I, I always tell people that if you want to take our money, but nothing else, and we are not the fund for you, we really want to partner with you, and we want you to be successful. And our job is to enable that success, but we also

have to generate a return. And this is all what I say when we pass, too. When feces pass, like we have a hard time saying no. We got a lot of nos. Remember that. A lot of people said no to us when we raised our fund. So we're not saying no and trying to be mean. I try to say no in the most, in the quickest way possible if we're a no

and also in the most respectful way possible with some feedback. Take the feedback. Like, don't be offended. Just because I don't want to invest in your company doesn't mean you're not going to build an amazing business. I'm probably wrong, and that's okay. There are a lot of people who didn't want to invest in me,

and they're probably wrong, and that's okay. So there's some things around like the founder VC dynamic that I think I didn't appreciate, even when I was fundraising for TaskRabbit, right? I'm trying to do different. My grandmother used to always say, let your yes be yes and your no be no. And so one of our values at TaskRabbit

is that we deliver hard truths with kindness. And I hope people, sorry, value a cherry rock because we deliver hard truths with kindness, I hope people experience us in that way because that's what we try to do. I love that. This is so nice. Totally wrote that down. I'm a little blunt sometimes. So I forget the sandwich.

But tell me, Tisi, if somebody wants to rise above the noise now, like it is really, really noisy. if they believe they have something awesome, but it's just really, really hard to ride above the noise. What do you say to people? It's hard, and especially the megaphones of the very big AI companies that are out there makes it really hard for anybody to rise above the noise. We look for founders who are audacious, accountable, and authentic.

And I bring that up because I think there's a matchmaking process in finding capital and going out and doing the work to find who's that investor that's going to see you fully, authentically who you are and ultimately help you decide that this is something that you can build and they want to partner with you to build it. and taking the time to do that. And so sometimes I hear, and even this happened to us, where someone wanted, you know, oh, I really just want to meet Bessemer. I really just want to meet, you know, this firm. But they just might not be a fit for you. Well, everyone else raised this money at this valuation from them.

So if I don't raise money from them, then I'm not going to be successful. That's like the absolute wrong way to think about getting access to capital. you really want to find the firm that's going to fit you. Like we only invest in companies that have product market fit and at scale. So if you're still early, we're just not going to do the deal. And so just trying to push that rock up that hill is like not a good use of your time. Go and find an investor that will see you for who you authentically are

and has a match with what they want to bring to help you build your best. business. Some of the best questions I get asked is, how are you going to help me be successful? And a lot of founders spend their time pitching, pitching, pitching, pitching how good their business is. Ask me, how can I help you be successful? And if you're not satisfied with the answer, then we are not the right source of capital for you. And that's so, so important. I think also, like, we sometimes give up too fast and just assume that, you know, if we met 10 people, they said no, then it's probably not a good fit. And it's just like, no, it's just a numbers game. Like, go hustle. Like there's a little bit. Yes. And it's throughput. So when I was fundraising,

I got some advice early on, which is that it's all about throughput. You have to sort of, how many meetings can you do, you know, in a day and in a week? Because it's just all about throughput. And that's the same for raising money as a founder. And I think it ties really beautifully to what you talked about learning all the time because I, you know, I think for our listeners, like, whether we like it or not, the first time we do almost everything, we suck. And we don't like to admit it. It's not fun, but we kind of do. And then the second time we'll be a little better and the third time will be a little better. And I think sometimes, like I think about some of my pitches to things like the first podcast, the first, you know, book, you know, publishers.

Like, I sucked, folks, and I'm good at pitching. And I still sucked. So I think it's also like, just realize it's part of the bustle that you need to build. Just continue being better and to find the right fit. But Stacy, maybe one last thing that you would say, like, to, like, if you met your younger self, what would you wish you could tell her? That she's going to be okay. I remember being a little kid and I thought I wanted to be a veterinarian.

And my dog died and I cried and cried and cry. And I was like, all right, I can't be a veterinarian. What am I going to do when I grow up? And that took me away from science and all that stuff because I just couldn't deal with dogs dying. Like, couldn't deal. and that took me into business and I was okay. And so I want her to remember that. That little girl up in her bedroom crying because her dog died.

Hmm. Aw, I'm almost crying here. Stacy, that was incredible. Where did they find you and where did they find your firm and all of that? Yeah, we got a website, terryrockcapital.com. I'm on LinkedIn. Not often, but give me some, be patient, be gracious. I don't respond right away.

And, you know, my email is Stacey at cherry rock capital.com. Amazing. And we're going to have all the information in the footnote. Stacey, that was incredible. And I got so many notes. That was incredible. Thank you so much. Thank you.

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