Stacy Brown-Philpot: Everybody wanted a thing for me after TaskRabbit, “I want you to do this. I want you to serve on this board. I want you to be the CEO of this private company. I want you to be the CEO of this public company.” The world needs a black female CEO in this role.

Jeff Berman: Stacy Brown-Philpot had just finished a wildly successful run as CEO of TaskRabbit, selling the business to IKEA, and she was trying to figure out what she wanted to do next. Not surprisingly, there was no shortage of amazing offers, but Stacy realized she wanted to scale her impact beyond what she could do with just one company. So she launched a new venture capital fund with $172 million from investors ranging from Goldman Sachs to our very own founding host, Reid Hoffman. The focus of the fund is under invested entrepreneurs.

Brown-Philpot: It means a lot to have sat in those shoes and to be able to see around corners and be able to help a founder think about how do you navigate that corner. And that to me was so fulfilling in a way that I was surprised and I didn’t realize.

Berman: Stacy is bolstering the diverse founders in her fund by sharing lessons from her decades of experience as a leader at TaskRabbit, Google, and beyond. Today, she’s sharing that wisdom with us.

[THEME MUSIC]

Berman: This is Masters of Scale. I’m Jeff Berman, your host. This week, Stacy Brown-Philpot offers incredibly valuable lessons from both sides of the venture capital equation. The former CEO of TaskRabbit has launched her own fund, Cherry Rock Capital. We talk about how to raise serious money, build a strong board, and the best ways to bet on yourself. Stacy, welcome back to Masters of Scale.

Brown-Philpot: Thank you.

Berman: I was listening back to your last appearance here when you were in conversation with Reid Hoffman, and a lot has changed for you since the last time you were here. Will you tell us about the transition from being an operator to an investor?

Brown-Philpot: Wow, that has been quite the change. I’ve gone from running a company by the quarter. Really every three months you have OKRs and objectives and things that you have to get done to thinking about what value can we create in 10 years. So I have to think a lot longer-term in what I’m doing. Going from being an operator and running TaskRabbit, successfully selling it to IKEA, I took a step back to really make this transition to think about what I wanted to do next, and in particular landed on the decision to become an investor and invest in the next generation of entrepreneurs. But it took me some time to get through the gymnastics of like, what’s the right next thing for me to do.

Berman: What was your process for making that decision?

The importance of self-reflection

Brown-Philpot: It’s going to sound crazy maybe to some people, but I took time off after I left TaskRabbit. I left in August of 2020, just right in the middle of COVID, if you may remember. And I did two things. I promised myself, I’d say no to everything for six months, and that was hard.

Berman: I imagine really hard because I’m betting you got a lot of interesting calls.

Brown-Philpot: A lot of interesting calls, a lot of interesting inbound. I lasted, if I’m being honest, five months, but I promised myself six months. The second thing I did was a silent retreat. I went away by myself for six days, five nights, which I’d never done ever. I’m a second child. I lived in that house in Detroit. At one point, it was seven people in that house. I’d really never been alone. I had roommates in college, so I needed some time and I took six days to just figure out who I was, decided that I loved myself more than I thought I loved myself, and I was pretty happy with my own thoughts.

So doing that right after leaving TaskRabbit was one of the best things for me to take a step back and figure out what do I really want to do. Why am I here? What’s my purpose? So people now ask me if I’m leaving this thing, what do you think I should do? And I tell them, you should try to say no, and I promise you the good opportunities will still come because you’re right. After the first couple of weeks, everyone’s like, “What about this job? What about that CEO job? What about this opportunity?” But they got better. And then the best one came, which was starting Cherry Rock.

Berman: The silent retreat, while you were there, was there a moment of clouds partying, angels singing? What was it like?

Brown-Philpot: My coach, I was working with a coach named Joe Hudson at the time, and Joe does silent retreats every year. And so he said, “Stacy, you should really do a retreat.” And I was like, “I don’t need a retreat. I got two kids, got a husband. We’ve been in COVID, I’ve been sequestered, I’m good.” But what was really going on is I think I was afraid of what might happen. Could I be alone by myself and what would happen to the rest of the world around me, my immediate world, my family, my kids, my mom, my grandmother if I was not available for six days? And so I said, “All right, I’m going to try this thing. I’m going to do this six days. I’m going to try it.” I remember driving to Half Moon Bay and stopping at the Safeway, buying all my food that I needed for those days, preparing to cook.

And I asked my pastor, I’m a Christian by faith. I asked my pastor, I said, “Hey, I’m going to do this retreat. I’m worried that I’m going to be bored and I’m not supposed to engage in social media or anything in the news.” So he’s like, “All right, I’m going to give you some Bible scriptures to read. Tell me some things you’re going to be praying about.” So I give him a list. He fills up this Google Doc. So I go in and I’m armed with all my reading and my food. And you know what happened? For the first two days, I just slept. My body was tired from just living the life of an executive, a CEO, having gone through an M&A transaction and a transaction having sold the company.

And so I was supposed to be meditating for three to four hours since in the morning, in the afternoon. And the advice was, if you fall asleep, just get back up and start again. Which I started doing and I kept falling asleep and I kept getting back up. But after the second day, I wasn’t tired anymore. I woke up and I was like, okay, I can meditate for three hours. I don’t need to do all this reading. I can just sit here and just let the thoughts come. So it’s a huge realization for me. It was one, the world does continue when you’re not around, people figure it out. Number two, your body needs to rest. If you allow it, it will take control and that rest will happen. And the clarity that came after that was just a centeredness that I don’t think I’d experienced in my whole life.

Berman: How did that change how you were thinking about what’s next, thinking about the world? How did that centeredness alter your perspective?

Brown-Philpot: Everybody wanted a thing for me after TaskRabbit, “I want you to do this. I want you to serve on this board. I want you to be the CEO of this private company. I want you to be the CEO of this public company.” The world needs a black female CEO in this role. But that centeredness brought me to what do I really want? What am I being led to do? What is my prayer leading me to do? And I was okay not fulfilling someone else’s expectations of me, but fulfilling my own expectations of myself.

So looking at every opportunity from that lens really changed how I thought about what I was going to do. And so once I decided to start a venture firm, all those people who wanted me to do something else, some of them invested in my fund, super excited to this day, send me great opportunities. They never not wanted me to start the venture firm. They’re so excited to support me, and I just had to lead them in a direction that I wanted to go, and they were happy to be along for the ride, but there was a point when I was worried I was going to let people down.

Berman: Wow. Where in the five months of no did you do the silent meditation retreat?

Brown-Philpot: Right at the beginning.

Learning to say no

Berman: Right at the beginning?

Brown-Philpot: Yes.

Berman: And so as these offers and opportunities were coming in after you came out with this clarity, was it hard to say no to anything? Was there anything where you go, “Gosh, I know I said I’d say no to everything, but this is going to be really hard to pass on”?

Brown-Philpot: Yes.

Berman: Can you tell us about any of those?

Brown-Philpot: Well, Sheryl at the time, Sheryl Sandberg, who you know is a good friend of mine and mentor, was throwing a lot of opportunities my way. And those are hard to pass on, less on what they actually were and more because I loved working with her when I was at Google, and I would’ve loved the opportunity to work with her again. So that was one of them.

The other was a lot of people sell their company, this is very Silicon Valley and then go become a VC. And so those opportunities came up to take on a real role at a venture capital firm. I did end up co-founding the SoftBank Opportunity Fund during that time, but I served on the investment committee. I wasn’t an employee of SoftBank, and I said, “I’ll be on the investment committee, but I’m not going to be an employee.” I said, “I’m going to say no pretty much to everything.” And so that one was a hard one. I didn’t really keep my no, but I didn’t fully go in because I wanted to give myself the space to figure out what I wanted to do and also get involved in something that I thought was important.

Berman: Why did you decide to say yes to the SoftBank Opportunity Fund?

Brown-Philpot: Well, I loved them. They were really good friends of mine. It was right after George Floyd was murdered. Everyone was figuring out at the time what they wanted to do, and so they were going to put a hundred million dollars behind it. That sounds like a good idea, and it’s something I’ve always cared about.

Berman: What did you learn from that experience that helped inform launching your own venture fund?

Brown-Philpot: One, I liked venture. I had thought about going into venture when I came out here to go to business school at Stanford, and that’s what I wrote my business school essay about. And was president of the Venture Capital Club, interned at a venture capital firm, SAP Ventures, but ended up going to Google and spending 20 years of my career as an operator. So this was my first time going back into thinking about the venture world and in a meaningful way, and I liked it. I said, okay, this is a job that I think I could do for some time.

Berman: What did you like about it?

Brown-Philpot: Meeting the founders, talking to different founders about the ideas that they had. The reason I didn’t go into venture right out of business school was someone told me, “You should go get some operating experience, Stacy because you’ll be a better investor.” I didn’t know what that meant. I thought I’d get some experience for a few years and it turned into 20. But it means a lot to have sat in those shoes and to be able to see around corners and be able to help a founder think about how do you navigate that corner. And that to me was so fulfilling in a way that I was surprised and I didn’t realize. The second is there’s no pipeline problem of finding under invested entrepreneurs. There just isn’t. If you talk about what you want to do and do the work, it will happen. And that’s what happened with the Opportunity Fund.

Berman: So you certainly could have gone and worked full-time at the Opportunity Fund, any number, probably no limit of Silicon Valley venture firms, A+++ firms would’ve been thrilled to have you come in. Why launch your own fund?

The story behind Cherry Rock Capital

Brown-Philpot: I wanted to invest in the next generation of entrepreneurs, and that’s really why not take a CEO job. And I wanted to do it in a way that I thought was unique and different, which is why my own fund. I really saw this gap in the market, which was access to capital that I thought wasn’t being filled by other firms. And a lot of firms have great mission, great values, great people, but it wasn’t my mission, my values, and my people. And until that point, I’d only backed founders, supported founders, invested in founders with my own money, and I was ready to be a founder of my own thing with my own mission, my own values, my own people in a way that I didn’t see existed in the world today.

Berman: The fund is called Cherry Rock.

Brown-Philpot: Yes.

Berman: Why is it called Cherry Rock?

Brown-Philpot: It goes back to my upbringing. My grandmother nicknamed me Her Cherry Pie. When I was growing up, I was 11, I made her a pie, and she is the rock in our family. She’s 96 years old.

Berman: Oh my.

Brown-Philpot: And still with us, thank God. And so Cherry Rock Capital is about being the foundation of success for the next generation of entrepreneurs.

Berman: How was it going out and raising the capital? It’s not an easy time to raise capital no matter who you are even if you’re you.

Brown-Philpot: Yeah, it was hard. And everybody said, this was January of 2023, “Stacy, this is the hardest time to raise money. You should wait.” I’d never done it before. So I didn’t know what hard really looked like. And you could argue now might be the hardest time to raise money. So I’m sort of glad that we didn’t listen to those people and we did it, but it was hard because I didn’t have a team. I co-founded it with Saydeah Howard, who was at IVP for nine years. So I brought somebody onto my founding team. She and I went out and raised this fund together. She had venture experience having worked as an operations leader at IVP to compliment my lack of venture experience.

But still, we didn’t have the whole team in place and people were less interested in investing in first-time fund managers and emerging managers. And so it was a challenge, but bit by bit, we just met people along the way who cared and invested in our success. Very early on, I shared my first pitch deck with someone who’s been in investing for decades, and he went through slide by slide and told me all the dumb things that were on the slide, things that I should take out, things that I should add. And he’s like, I’ve raised billions of dollars and this is how you should position this. And that was so helpful, slide by slide. And so V1.0 of the deck became version 2.0 because of that person, and we would not have raised $172 million had it not been for his help along the way.

Berman: The contrast here is so interesting because on the one hand, you’re getting the advice, “Stacy, don’t do this now. This is a really hard time. This is a bad time to do it,” which in hindsight was probably really bad advice given how hard the market is now. So there’s a set of lessons there. But on the flip side, you’re getting this other advice about slide by slide, tweaking the deck, which sounds like it turned out to be really good advice. So how did you know to differentiate between what turned out to be the bad advice and the good advice?

Brown-Philpot: It still goes back to my grandmother. Grammy always told me that not everybody’s going to like what you’re doing. Not everybody’s going to support you, but you just have to believe that whatever you’re doing is the right thing and you just go do it. And so even as people were saying, “It’s a bad time, don’t do it,” and I was like, “Well, when else am I going to do it? It’s kind of now.”

The person who took me slide by slide said, “Okay, fine. You’re crazy, but if anybody can do it, you can do it and I’m going to help you.” And so I learned to sort of follow my own North Star, and this goes back to the silent retreat of being very grounded in what I thought was important, and being able to tease out sometimes negative or discouraging feedback is a motivator. And for someone like me who grew up in Detroit, it’s almost always a motivator. You tell me I can’t do something, I’m going to figure out like, “Oh, really,” as opposed to like, “Oh, maybe I can’t.” I’m usually going to go and they’re like, “Oh, really,” and I’m going to prove you wrong camp until I realized for myself that I can’t do it.

Building from scratch as a first-time founder

Berman: You have this wealth of experience at Google, I mean, extraordinary run there, coming into TaskRabbit as COO and becoming CEO after it had already scaled a fair bit and obviously taking it that last mile. So in many ways this is really your first startup that you are doing right?

Brown-Philpot: Yes.

Berman: I mean, that’s hard. You don’t have infrastructure, you don’t have process and teams and people and software and all the things. I mean, you got to set up bank accounts. I mean really fundamental stuff. How has it been going from having all of this structure and support and process around you to really being you and having to figure it out and do it yourself?

Brown-Philpot: I spent my whole career helping other people’s ideas grow and flourish, but I’d never really bet on myself in a way that I was starting from ground zero and now I get to do that. So there’s a part of me that’s extremely fulfilled and satisfied by the decision to go from zero to one with this firm. So no, we didn’t have the infrastructure, but one thing I didn’t know how to do is hire and build a team. And a lot of people start a venture fund and they’ve got a lot of good ideas and they have a great network and they know every founder, but they’ve not been a CEO of a large organization before.

And so I knew how to build a team. I said, “If I’m going to raise institutional capital from the likes of JP Morgan, for example, they’re going to want to see something solid in place. I’m an accountant by training. I want to see that in place.” So that’s why I hired Saydeah. I brought Saydeah in to co-found it with me and said, “Look, we’ve got to build an institutional grade fund so we can go out and raise institutional capital and convey to the market that although we’re new, we’re going to build something that’s going to be around for decades to come.” And that was really how I thought about this zero to one.

Berman: Still ahead, advice from Stacy Brown-Philpot on how to find or be the best possible board member.

[AD BREAK]

Welcome back to Masters of Scale. You can find this conversation and more on our YouTube channel. Is there in the process of raising capital, an inflection point where you know you’re going to get there, what is that process like for you? Yeah, maybe not.

Persistence and rejection in venture fundraising

Brown-Philpot: You never really know if you’re going to get there.

Berman: No.

Brown-Philpot: I had this sort of assumption that we would raise the money in a very short period of time because we had a great list, we had great referrals. We had obviously iterated the deck. We had some early momentum from a lot of individuals who were excited to back us. It was kind of like running a company. All of these things were supposed to work, but they never really worked out that way. So no, it didn’t work out that way. I didn’t know if we were going to raise the full amount until the very end.

Berman: Really?

Brown-Philpot: Yes.

Berman: Why was that?

Brown-Philpot: There were a couple of things that happened. One is the market is just slower. We started January 2023. We had our final close in January of 2025. It took two years. And when you look back at the data for a lot of first time funds, this is about how long it takes, and I was ambitious thinking, “I’ll do it half that time.” I was wrong. The second thing is we raised a lot of institutional capital, and when you’re raising from Ford Foundation and JP Morgan and Mass Mutual and Goldman Sachs, these funds, these firms have a process and their process is three to nine months, depending on when you start, how much you know them already. And it’s a relationships business, and you have to build the relationship over time. Most of the people we talk to said no, just like anybody else, when you’re raising… you’re selling something, you’re raising a fund, most people we talked to said no, but enough people said yes. It just took the time to build the relationships.

Berman: Yeah. Do you ever get used to hearing no?

Brown-Philpot: No.

Berman: Yeah.

Brown-Philpot: And people, if they say that they are, I didn’t want to know who those people they genuinely are. You never really get used to hearing no. You put all your heart and your passion and your energy. I also never got tired of telling the story, even though I knew that there’s a higher chance that this person’s not going to invest in my fund than if they are because I was so convicted about building this firm that I’ll tell the story over and over and over again.

Berman: What’s the story you were telling?

Brown-Philpot: Well, the story is really just Cherry Rock Capital, as we just discussed it’s about becoming the foundation of success for the next generation of entrepreneurs. I want to invest in the next generation of entrepreneurs and take everything that I’ve learned and help them be successful. There’s a gap in the market, which is access to capital for under invested entrepreneurs who don’t have access to board members like me who haven’t been to Silicon Valley for 20 years, and who don’t have the networks that they need beyond the capital. So not only do we bring capital, we bring operating expertise and we bring networks, and that’s different.

The Coactive investment

Berman: When did you make your first investment out of Cherry Rock?

Brown-Philpot: We made our first investment in Q1 of last year, 2024.

Berman: What was that first investment?

Brown-Philpot: Coactive. We invested in Coactive.

Berman: Tell us about Coactive and why you put money in.

Brown-Philpot: Oh, it’s a great company. So I met Cody Coleman, who’s the co-founder of the company earlier in 2023. He was a PhD out of Stanford and co-founded the company with his friend who he went to undergrad with at MIT. And a friend of mine said to me, “Oh, if you’re thinking about starting a fund, you should meet Cody.” I didn’t have a pitch deck yet, nothing, but I reached out to Cody on LinkedIn and said, “Hi, this person said we should meet.” He wrote back right away. And most people don’t respond to LinkedIn inbounds.

Berman: Even from you?

Brown-Philpot: I’ve learned that people do respond to me.

Berman: I would imagine so. I mean, if you show up in someone’s DMs, it’s a little bit different than most people showing up in their DMs.

Brown-Philpot: I DM’ed him and he responded. So we got on a quick zoom. He told me about what he was building. I didn’t have a fund yet, and he was closing his series A. And so I personally invested. So for about a year, Cody and I just built a relationship and really thought about how I could help him as a CEO. The company is a multimodal AI company that helps businesses organize and analyze information across video and image data to help them better sell to their customers. Great business. And it was right before ChatGPT launched that he closed the A. Then ChatGPT became very, very popular as you know. And then as a result, everyone was like, “Oh my God, AI.” He wrote his dissertation on what is now Coactive today.

So I was just impressed with him. His leadership, his vision, and a year of working with him showed me that he was going to build something great. So by the time the series B came around, we had closed some capital. We had not reached 50%, but one of our LPs said, “Get in business, Stacy. Do some deals and show that this team can win deals,” and ultimately co-led the series B with Emerson Collective, and we want to be value add. So with Coactive, we were able to demonstrate we can win the round. I’m on the board of Coactive.

Berman: A lot of VCs don’t want to take board seats.

Brown-Philpot: Yeah.

Berman: Why do you want them?

Board membership: Role, risk, responsibility

Brown-Philpot: I’m not scared of it, and I understand what it means. I’m on the board of HP, iconic. It’s a lot of governance. I understand what it means to be a board member of a public company and a private company, and there is risk. When bad things happen, the board is responsible for it.

Berman: And bad things do happen.

Brown-Philpot: Bad things 100% do happen, but I’m not afraid of it. The other reason why a lot of investors don’t want to be on the boards, at least what they tell me is, “Well, I’m not going to get as much insight because when you’re the board member, the founder doesn’t want to talk to you as much,” and that’s just not true. I found so far we have three portfolio companies that we have access, we have information. We’re adding value in a way that I think is useful for the company. And having been a CEO, I don’t get to run the company. I just get to tell you what I think and you get to take all those inputs, including mine and make decisions.

Berman: Is that hard? I mean, are there moments where you’re just itching to jump into that chair and fix the thing or make the decisions differently? Do you struggle with that ever?

Brown-Philpot: Sometimes.

Berman: Yeah.

Brown-Philpot: I have to admit it. There are days when I say, “Wow, if it were me, this is what I would do right away.” But then I remember I have had board members say to me, I never actually say that, have had women say to me, “Well, this is what you should do. If it were me, I would do this right away.” And I’ve sat there knowing they have no idea the 20 other things that are going on that are impacting my ability to do exactly what you’re talking about. And so I have to remind myself that I’m not an operator anymore. This is a multidimensional job, and that one little thing that you would do right away is probably not possible, and they probably thought about it.

Berman: Also, I find as a board member and with board members the simple question of, what’s most helpful right now, some version of that. Are you looking for advice? Are you looking for support? There’s a bit of a process in figuring out what’s really needed in that moment and having been an operator, I imagine that informs how you approach some of this as well.

Brown-Philpot: It’s so true. I encourage a lot of CEOs to join a board so they can learn exactly what you just described. When I joined the HP board, I was the COO of TaskRabbit, and the first thing that I learned was, it’s not about the advice that you give. It’s about the questions that you ask. The best board members in that room ask the best questions. So when I became the CEO, I now had a board that I had to teach how to ask questions, and it was less value for them to me to come in and tell me all the things I should do. I’m here every day, I’m running this company every day. You come every three months for the board meeting. Anything you say is probably not going to be as valuable, but what is going to be valuable is the questions that you ask. And so being a good board member for me is about just that. How do you help the CEO and the founder think differently based on the questions that you ask and ask them, how can I support you?

Berman: Yeah. This is a really, I think, critical insight. I want to spend a minute on. I was on the board of a company called Buddy Media that had a terrific exit to Salesforce, founded by Mike and Kass Lazerow. What I learned from them serving on their board was the best boards are actually managed by the CEO and founders. The board isn’t managing them. Now, obviously there’s governance, there’s oversight, there’s responsibilities there. What is your advice to founders who are managing a board for the first time or don’t think they’re great at managing a board about how to become great at doing so?

Brown-Philpot: This is great advice. I first of all, don’t put a board together until you need one. And sometimes it’s perfunctory and you feel like, “Well, I have to have a board.” Think hard about if you’re raising a seed round, do you really need a board yet? Maybe you don’t need a board member until there’s the series A.

Berman: How do you know when you need a board?

Brown-Philpot: What trajectory is the company on? What vectors are you trying to capture? Is it go-to-market expertise? Is it entering into new partnerships? Is it going into new areas? Are you trying to build your leadership team? Do you have the right people around the table who are asking you those questions? Are you planning to take real meaningful institutional capital where they’re going to require a board seat because of it, but is that capital going to get you to the next major milestone of the company? Think about those things because that’s really what will determine whether or not you should have a board or not.

Keeping humans in the equation amid the AI revolution

Berman: As we sit here very much in the midst of an AI revolution, there’s a range of optimism and pessimism around AI. Where are you on the spectrum of AI optimism and pessimism, and what leads you to that place?

Brown-Philpot: I’m optimistic. I was thinking back to my first conversation and the title of it was Keeping Humans in the Equation.

Berman: It absolutely was.

Brown-Philpot: Which was fascinating because at that time we were talking about the role of how things scale and we were automating a lot of things, but ultimately, you still need the person to put the groceries in the refrigerator, and here we are today in 2025, and I’m still optimistic about keeping humans in the equation.

Berman: Well, we talk about humans in the loop as a key part of AI.

Brown-Philpot: It’s a huge part. Even with companies now trying to bring elements of artificial intelligence into how they run their business, it’s not plug and play because the data isn’t secure enough or it’s not 100% accurate. It’s 99.9% accurate, which is not enough if you’re making decisions. It has to actually be 100%. So you still need humans to do that 0.1% to get you to 100%. And so just like technology in the entire time that I’ve been had a career in technology has helped advance the thinking of us humans and our learning, that’s what I think is going to continue to happen in the future, and I’m very optimistic about that.

Berman: How are you continuing to learn right now?

Brown-Philpot: I read a lot. I listen to my children because now they’re at the age where all the great ideas are coming from them, and I still meditate.

Berman: How great. What a wonderful place to wrap. Thank you so much for being with us.

Brown-Philpot: Thank you.

Berman: Stacy Brown-Philpot’s transition from operator to investor is full of valuable insights. Maybe the most essential lesson is to find a way to block out the noise so you can get clarity on what you feel most called to do. For Stacy, that’s dedicating her energy to helping a new generation of under invested entrepreneurs. Whether or not it takes a six day silent retreat, I hope you can find some quiet and some clarity as well. I’m Jeff Berman.