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Stacy Brown-Philpot, former CEO of TaskRabbit

Stacy Brown-Philpot epitomizes what it means to be a tech leader. She is the former CEO of TaskRabbit, a same-day service platform that connects people with skilled Taskers to help with odd-jobs and errands, and before that spent over a decade at Google where she led operations for all of Google’s consumer products, including Google Search, as well as Google’s operations in India.

During her time at Google, she founded the Black Googlers Network, which has been instrumental in growing the community of black employees at Google and in tech more broadly. And she’s a founding member of the Softbank Opportunity Fund, which is dedicated to supporting and building a community of outstanding Black, Latinx, and Native American founders.

In this episode, recorded live from the Concrete Rose Summit in Menlo Park, CA, Stacy takes us through her experience at TaskRabbit, including navigating the pandemic and the company’s acquisition by IKEA, and shared her perspective on building and managing game-changing communities through a tech lens.

We appreciated Stacy’s perspective on the need to leave things better than you found them, and we certainly felt much improved after this conversation.

Special thanks to Concrete Rose for inviting us to their Summit, an incredible gathering of the founders Concrete Rose supports, Concrete Rose LPs and advisors, and an all-star lineup of tech and investing leaders there to support Concrete Rose’s mission of deploying social and financial capital to talented founders from underrepresented groups.

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Episode Transcript:

DAVID STIEPLEMAN: Hello and welcome to It's Not Magic, a podcast from Sixth Street about business building that strips away the pretense and gets right to the useful stuff. I'm your host, David Stiepleman. Welcome to Season Two. We use this show to talk to founders and industry leaders and get them to explain in plain English what they set out to do and specifically how they do it. This is a really special episode to kick off our second season. It was recorded live at the Concrete Rose Summit. You may remember our conversation with Sean Mendy of Concrete Rose from earlier this year in Season One. The summit was a really incredible gathering of 200 founders of color, Concrete Rose LPs and advisors, and an all-star lineup of tech executives there to support Concrete Rose's mission of deploying financial and social capital to talented underrepresented founders.

STACY BROWN-PHILPOT: It's what brings me energy, like I can turn fear into faith and hope and optimism and, let's go get it. Let's go do it. And I just love that. I love living my life that way.

DAVID STIEPLEMAN: That's Stacy Brown-Philpot. Stacy is amazing. She's a successful tech executive, the former CEO of TaskRabbit, and before leading that company, spent almost a decade at Google during which she led operations for all of Google's consumer products, including Google search, as well as Google's operations in India. She's the founder of the Black Googlers Network, which has been instrumental in growing the community of black employees at Google and in tech more broadly. We talk about all kinds of things including leading through crisis, being one of the only black women leaders in tech and so much more. She's now the founding partner of the SoftBank Opportunities Fund, which invests in black, Latinx and Native American founders. I think you're really going to enjoy this conversation. We talk about the importance of leaving something better than how you found it, the difference between founding a company and coming into the CEO seat from the outside and how you can't force all culture or community growth, sometimes you have to let it happen on its own. We learn that doing your part to change the world may be scary at times, but it's not magic. Let's jump in.

It's great to be here. I'm not an excitable person, I don't think (my kids may say different), but I'm so excited to be here for a number of reasons. One is that we're recording this conversation for the Sixth Street podcast, “It's not magic,” so you’re all here to witness the creation of some historic content, (no pressure), and then of course, I'm super excited because I'm talking with Stacy Brown-Philpot, which is awesome. So, I don't think you really need much introduction, but I'm going to do a little bit of introduction, which is obviously a founding member of SoftBank Opportunities Fund, which invests in black, Latinx and Native American founders and companies from seed to series C and of course the former CEO of TaskRabbit. And we're going to talk about a bunch of your other stops along the way. I want to start, if we can, at themes or through lines through your career, and one way to think about your career, and I've been thinking about your career and your journey, is that from, I don't know, even from Detroit to Penn, to Goldman, to Google, to Stanford, to TaskRabbit it, you've on the idealistic side of tech, building community, changing the world, doing good things. Is is that a fair way to think about it? And if so, well if not, tell us why and if so, was that deliberate?

STACY BROWN-PHILPOT: It's an interesting question because I grew up in Detroit where we were taught community family values, work ethic, work hard, get what you pay for, what you see is what you get. And so those were the values that I grew up with. And I knew nothing about Silicon Valley. I didn't know what these people were doing out here. I went to Goldman Sachs. The businesses that we did M&A transactions on actually made money and were profitable . And so, when I got to the Bay Area, they're like, ‘Oh, these people out here, they are changing the world. Like this is the ecosystem. ‘And this was in 2000, like everybody out here is on a mission to change the world.

So, when you ask me a question of like, I followed an idealistic path and it was that intentional and, isn't everybody in here out to change the world? And if you're not, what are you doing? Why are you here? And so, for me, it's my upbringing that really helped me see that if I'm going to be in any room, in any circumstance, in any environment, I have to leave it better than I found it. I have to talk to somebody who I wouldn't otherwise talk to. I have to help somebody who I wouldn't otherwise help. Sean asked me to do this summit. I said, ‘Sure’. Oh, I said, ‘What day is it?’ And he tells me, ‘It’s today.’ And I'm like, ‘Ah, I'm going. It's my birthday. I'm going away for my birthday.’ And I'm like, ‘But for you, I will go later because I know how important this is to you.’ And so, I don't know how this works in the future and what comes of the next 41 minutes and 48 seconds we have together, but I'm doing it because it matters. And so, if that's being idealistic me, that's just the essence of who I am.

DAVID STIEPLEMAN: Well, okay, I want to dig into that a little bit. I want to take a moment to talk about the moment where you're leaving Google, you're a senior executive there you have a successful (almost decade run there) and you're thinking there's more. Can you talk about that?

STACY BROWN-PHILPOT: That was hard. To leave Google was so hard because my mother, when I joined Google, she's like, ‘If this Google thing doesn't work out, you can always go back to Goldman Sachs.’ And that was in 2003 when it wasn't the company that it is today, (Google had about a thousand employees), so the company grew to 50,000. I'm sitting in this corner office with floor to ceiling windows on two sides. I had my dog in his bed, I had a desk, I had an assistant, I had a huge team. I think I was managing like 600 people at the time, and I was extremely comfortable, and I had a baby. Emma was probably five weeks old when I started the process of thinking about what I was going to do. Google had mother's rooms with refrigerators in them so you don’t have to tow all your stuff (around those of you who are parents.)

And I just didn't even imagine. And it's the company that everybody wanted to work at. Our acceptance rate was lower than Harvard and Stanford and Princeton at any Ivy League school for applications. But as I looked around, I started to really feel two things. One was just I wasn't pushing myself. I wasn't at the precipice anymore and looking down thinking , ‘whoa, I might fall off’ and ‘if I fall, it's going to hurt.’ I felt like I wasn't taking risks. The other one is that I had become this sage. I had been there for so long that people would just show up at my office and be like, ‘Can you walk me through this thing three years ago that happened’ and, ‘what was the history?’ And I was like, ‘I am not Yoda.’ And so ‘I did not want to be Yoda.’ And so, it was time for me to go. And so I had to break up with this great opportunity in order to really see the TaskRabbit opportunity when it came along.

DAVID STIEPLEMAN: So, you're describing being on the precipice and about to fall off. That sounds bad, but you like that. Why do you like that?

STACY BROWN-PHILPOT: It's what brings me energy. I can turn fear into faith and hope and optimism and, let's go get it. Let's go do it. And I just love that. I love living my life that way.

DAVID STIEPLEMAN: Is that a clap of recognition? How do you do that? Tell us more about how that gets done.

STACY BROWN-PHILPOT: You know, I grew up in an environment where we were taught to act a certain way, be a certain way. If any of you for traditional black families, you never talk back to adults and all these things. There was a lot of structure in it, in my upbringing, but I also grew up learning how to advocate for myself, and every time I put myself out there, most of the time it worked out. And so, every time I tried it, I said, ‘Oh hey wait, what if I try to go to the school that nobody thinks I can get into?’ Like Penn, I got in, I was like, ‘Oh, that worked out. What if I, you know, try to get into Stanford business school?’ That worked out. And so, most of the time the things that we think are the things that we will fail at are never really truly failures. They're just learning moments, and I learned how to see potential risks as not this fearful thing where everything's going to fall apart, but actually there's a learning moment on the other side of it, and I was more excited about the learning than I was afraid of the potential failure. So that might be a mindset shift that ‘how do you do it?’ That might be how you do it.

DAVID STIEPLEMAN: Got it. Actually, I want to touch on something you said, in your upbringing and, and moving forward, this this kind of it's a competitive drive, it's a drive, it's always making stuff happen, it's always powering through, working hard, being prepared, all the stuff that everybody in the room as founders that you have to do. But we're talking about leadership in part. Is that good leadership? What's the cost of that? And does that always work or have you had actually there was, what did, what did, did I say we should be sharing our, we should reveal our intentions? That was one of the principles I'm asking because that was the prompt, I think it doesn't always work that, that doesn't always carry us all the way through, and it has some real costs. Am I right?

STACY BROWN-PHILPOT: It does. You can be wrong, and there's a lot of consequences. So I remember like you, many of you in this room, you all started your companies, you've always only ever been the CEO of the thing. And I grew up as an executive in companies and I became the CEO of TaskRabbit. But first I was the COO and I always thought, ‘the CEO thing can't be that hard.’ I think it's to go to all these meetings and these conferences and stay at these hotels and really, how hard is it? So you get the job there are meetings and there are conferences and there are hotels, but there's this pressure of people have trusted you with most of their waking hours of the day to follow you on a mission, a purpose, a path that you believe with, let's face it, y'all, 70% confidence is really going to work. We're all being honest with each other. But if you're in front of everybody, you're like, no, we're 110% sure this thing is going to work. And you've got to get up there and be 110% when it's really more like 70%. And that feeling of responsibility and trust that you have to carry is difficult. And so when it's wrong, it's bad. We had a bad product change at TaskRabbit and it cost us a bunch of revenue.

DAVID STIEPLEMAN: Actually talk about that, if you don’t mind.

STACY BROWN-PHILPOT: That was terrible. We changed the product because we were trying to grow, and we needed to pivot in order to grow. Some of you are in the middle of a pivot, you know what I'm talking about. We launched this big change and it was going to cost us about 70% of our revenues because we were shifting to focus on certain categories that at the time, was 30% of the revenue, but we knew it would grow faster and it was unclear if that was really going to work. But we had a lot of conviction, and the team was like, ‘I don't know,’ I mean nobody really knew we had the data, but whatever, it doesn't matter. The customer doesn't show up, you don't have a business. So, we went down, revenues went like this, and we said, ‘All right, we got 60 days to see the corner turn.’

We gave ourselves a timeline, we set some metrics on what we wanted to see. We wanted to see better NPS and better customer quality and better fulfillment rates. Like there was some core business metrics we were looking for. But in that 60-day period, I was terrified that this thing was not going to work. And people trusted their lives and the taskers, even more important than the employees, we promised them they would make more money, ‘Go with us, you will make more money.’ And many of our taskers earned their livelihood on our platform. So this was serious stuff. This is like, ‘can I pay my rent this month or not?’ And sure enough, they were able to set better hourly rates, they were able to get more tasks on a more frequent basis. They were able to do things like consolidate tasks in certain geographies within certain cities so they can do more tasks in a day, which meant that their hourly rate and their daily rates went up. And so, there were a lot of things that we weren't sure were going to work and we had to make this change and we made it and, it worked out. But there's a trust element that the cost of it is if you get it wrong, it's really wrong for a lot of people.

DAVID STIEPLEMAN: Do you remember a moment when you were in the dip and you're sitting there and someone comes in your office and they're like, ‘I don't, I don't think it's going to work.’ And, what did you do? Did you project 110% that you’re sure?

STACY BROWN-PHILPOT: A lot of our clients who used the service were not happy with this change. And they were upset, and they were calling. So I agreed to do some of the calls. I said, ‘Fine, I'll take calls.’ Leah was taking calls, I was the COO, Leah was the founder. So I was like, ‘I'll take some calls.’ I remember sitting in my living room at 7:00 PM talking to one of our highest spending clients, most active. She was like, you know, you have the 80-20 rule, which we didn't, but if we did have one, she'd be in that category. And she was yelling at me, ‘I can't believe you made this change. I'm never going to use TaskRabbit again. Do you understand how much money I spend on the platform? This is awful.’ I was sitting on my couch and I got off the phone and I cried, and I was like, ‘we are screwed.’ And I just, this is the type of client that we wanted to be happy with this, we wanted her to use TaskRabbit forever. And she was done with us. She was done. And that was the moment when I said this isn't going to work. It was like the conviction of, we promised 60 days, we promised these metrics. We can't let one client, dictate the future of this company. But it was 7:00 PM and by 7:12 PM, I was sitting there thinking, we made a huge mistake.

DAVID STIEPLEMAN: Wow. That's on story. Turns out it was a good decision.

STACY BROWN-PHILPOT: Turns out it was

DAVID STIEPLEMAN: A good decision. It came out of the nosedive.

STACY BROWN-PHILPOT: We came out, it was a good decision. She did start using TaskRabbit again.


STACY BROWN-PHILPOT: She didn't really have a choice, but what we learned was that, when you're building community and we're talking about community, people think that they own the company. And I should have remembered that lesson from Google, which is when Google became so big, everybody thought they owned Google. And any decision Google made was like, ‘this is terrible. This is awful. This is my search engine, this is my, this is my company.’ Well, the same thing to as TaskRabbit where the clients and taskers that this was their livelihood, this is how they got things done and, you make a change. This is my, this is my company. That's the power of a strong community, but also sometimes the cost. So yes, it worked out. We ended up, shifting to just a few categories. Our fulfillment rates went up. We were able to invest in growth because our LTB to CAC ratios got better, and everything went well. But that was a dark moment.

DAVID STIEPLEMAN: I mean the interesting part of it also was that the taskers started teaching each other, ‘Hey, you want to get better at whatever, name your task,’ (I don’t know how to do anything. So, I can't name a task off the top of my head nailing a nail into something.) They actually were making videos and helping out each other, and it was this community reinforcing itself. Was that part of the underwriting when you underwrote the change?

STACY BROWN-PHILPOT: It was absolutely part of it. Because we always give the example of people making YouTube videos on how to drill a hole in a brick wall. Because in some cities, (I lived in an exposed brick wall apartment in New York), but there are a lot of places where you can't, it's not like a plaster wall. It's very hard and it's a different skill to mount a TV, on a brick wall. But if you can do that, there's a premium you can charge on your hourly rate. And so we had a tasker who put together this YouTube video. We didn't ask him to do it. He just said, ‘Look, I want to help people be successful,’ and that became part of the community. And so, one time I hired a tasker change some light switches in my house one time. And he came and I said, ‘How did you learn how to do this?’ And he’s like, ‘two years ago, I didn't know what a handyman was. I didn't know how to do anything.’ And he's like, ‘I've basically been watching YouTube videos for the last two years practicing in my house. My wife is so over me taking stuff apart and putting it back together. But that is how I've been able to earn a living for our family.’ And that was a part of the community that we knew we wanted to happen. You couldn't force it. It had to be organic because it couldn't be the company training people how to do a good job. It needed to be our best taskers, caring about the community enough to teach other people. And that's what made it more viral.

DAVID STIEPLEMAN: I want to fast forward to end of 2019, beginning 2020. You'd sold the company to Ikea. I'm having flashbacks of trying to put together pieces of furniture for Ikea. I'm very bad at that. You have come up with a succession plan. You're like, ‘We accomplished a lot. Like I'm good.’ And COVID starts to happen. You start to see a flashing red light, (metaphorically speaking), from Seattle. Tell us what happened.

STACY BROWN-PHILPOT: My transition plan, I had three objectives post acquisition. Number one, not suck, just make things works. It should not suck for the employees at TaskRabbit and for Ikea and the people who got up in front of their board and bet on us and championed this deal. Number two. So that was year one, let's make this thing not suck. We could all get the IKEA discount in the store and it works. That was a big issue because we got acquired and people went shopping like ‘I did the discount and it didn't work, this sucks.’ I was like, ‘we got to fix this. It can't suck. We literally have to make sure everybody gets that 10% discount.’


STACY BROWN-PHILPOT: Number two was, make it commercial. Let's actually grow this opportunity. Let's not let it sit here with this great little TaskRabbit business but figure out how do we really grow. Ikea became a quarter of our revenues. We launched in a bunch of new countries with IKEA as part of our big commercial partner, which saved us a bunch of marketing dollars. Their NPS scores went up, their unaided awareness about service actually improved, which was important for them as a brand. So, I was like, ‘great commercial value.’ And then the third was get a team in place that can carry this thing forward. This is not about you, Stacy, or Leah as the founder. It's about the legacy that we leave. And so, I built a team, we got some more senior executives who knew how to run global teams.

And so I started the process of my transition at the end of 2019. And then January comes and there's a thing in Japan remember. And we all were like, ‘oh that's the thing in Japan on a cruise ship. And then and then there ‘was something in Seattle like, wait, this virus is in America. What's going on?’ So, by March we were shutting down the marketplace and I remember we were supposed to have an offsite, in the middle of March 2020, we literally canceled it. And then at the end of the month, we were supposed to have a board meeting in all of the IKEA team was coming in for the board meeting and they were going to interview the candidates for the CEO job. That was that meeting. Of course, that meeting didn't happen. It was virtual. We were all on Google Meet, we weren't using Zoom yet.

And the conversation was very different. A bunch of candidates pulled out of the process. We had to shift our timeline and the entire meeting was about do we keep the marketplace open or not (the TaskRabbit marketplace) because it was unclear what this virus was, how it could impact people. People were dying, they were in hospitals, there was not enough equipment in the hospitals. We didn't understand, we weren't wearing masks then. There was no such thing, there was no such concept. And so at the board meeting, we're talking about what do we do? And at this point IKEA had closed all their stores because that was a mandate that they had. And so ‘you got to shut down Stacy.’ But we had a bunch of taskers who were active on their Facebook group asking us to keep the marketplace open because they've been furloughed or they lost their jobs and there was no rent relief.

They had no idea if they were going to be able to pay their bills. So we had to make this really difficult decision to keep it open. And we debated it for about an hour and we went back to our mission and our values, which was caring deeply. And if we really going to care, we can't just let people go broke. We also had all these clients feel like, ‘Oh my god, my kids are at home and wait, we're not going back after spring break and we need desks, we need trampolines, we need stuff in our backyard, we need all these things. We have no idea. I don't want to go outside. I'm scared.’ So, we created a very safe way for our taskers to continue to task because we cared enough about our community to find a way to get through one of the hardest times that we faced as a society.

DAVID STIEPLEMAN: Taskers on the front lines of that. It's an incredible story that you're making decisions at the bleeding edge of this thing that governments are getting wrong. Everyone's getting no information. It's incredible. Hopefully with lesser, broad global consequences. But I'm interested in how, (I'm thinking about the founders in the room), we’re in some economically turbulent times now. If you read the financial press or whatever, you are thinking, ‘gee, what's coming, maybe a recession.’ How would you, you can talk about the economic indicators if you want or what you think is going to happen, but maybe more interesting for the founders in the room is how would you prepare? How would you think about what might be coming?

STACY BROWN-PHILPOT: I would have perspective, I'm old enough now to have some more perspective. Not as much as my 94 year old grandmother, but definitely some which was in 2000 was a bad time. That was when Google came to be -- 2008, really bad time. That was the dawn of the gig economy. All those companies, Uber Lyft, TaskRabbit, Airbnb, right around that time. It was a time when, which I think is really important like we are now, where I don't think that ecosystem of independent contractor work could have flourished if we weren't in the middle of recession. Where people were like, ‘I really have to find a way to make some money and how can technology be an enabler of that?’ And so, when I look at today, it's really scary when I think about, Chris and I went to dinner last night and he was like, ‘is this really $97 worth of food?’ I was like ‘I think so. I don't know. We had a salad, it is Palo Alto'. But prices have gone up and it's really scary to see this happen, and wonder is it going to forever be that way?

But a different perspective might be to ask the question, what opportunities are being created today that we wouldn't otherwise have had? And how can we accelerate our pace in ways that we would not otherwise have been able to do? What can we learn from the mistakes that have been made over the last year that we want to do better at? I think if you have that perspective, that's the precipice view. It's not like how far down is that? It's kind of looking down and I drew this picture recently of I'm at the precipice and there's the water. So, if it's a soft landing because it's in the water, but there's a fish coming out and it's either a shark or a dolphin. And so see it as a dolphin, not as a shark. So even if you fall, it's going to be somebody in there that's going to make sounds and ‘Say, hey, Stacy's in here, somebody let's help her Get out’ and not the shark that's going to eat me. So I think if you see today like that, which is it's a dolphin, not a shark. And even at the precipice of something really scary, there's opportunity and I'm going to go for it. That's a much better way to live right now.

DAVID STIEPLEMAN: Let's talk about relationships. Relationships matter. I've heard you say that a couple of times. What does good mentorship look like? And I'm asking in part because at some point there's going to be lunch and interstitial time and we're all encouraged to meet each other and share our stories and how should people do that?

STACY BROWN-PHILPOT: With intention. We place this heavy load on mentoring, but relationships are really about being thankful for the opportunity to interact with somebody and the chance to get to know them because you never know when that meeting, that interaction is going to turn into something more positive. And so be intentional and don't be aggressive like, ‘oh I really want to meet’, looking at a list like, ‘Oh I'm going to go meet this person and make sure I pitch, or make sure I walk through, oh, we got to structure this partnership.’ It's more about getting to know who the person is. I do a devotional every morning. I'm a Christian by faith and I do a devotional every morning with my best friend who lives cross-country. And today's was about relationships and being grateful for the relationships. And so I was thinking about this event and why I was doing it. And relationships don't matter like today in this moment, they matter over time. And the learning that I had from my devotional this morning was, it's not about what's happening right now for somebody, it's about what you build over time with anybody and everybody. So be grateful for this opportunity to be here and go into every conversation with that form of gratitude. And something will come to bear. It may not be today, it could be a year from now, five years or ten years.

DAVID STIEPLEMAN: That's lovely. I like that. We're in Silicon Valley so I'm going to use the word pivot. We're going to pivot. I feel like Reed Hoffman was here. I can't speak that language. We're going to pivot – SoftBank Opportunities Fund. Talk about if you would, the transition, if it is a transition from entrepreneur, operator executive to investor (and they're not mutually exclusive obviously), but what was surprising? Hard, not surprising.

STACY BROWN-PHILPOT: Yeah, it was easy to start the fund. We had the luxury of having Marcello who was at SoftBank at the time get a hundred million dollars in 24 hours to invest in black. I know, I see. She's laughing. She's like, what? In black, Latinx, Native American founders. Without, we didn't have a stated, mission statement or anything. We just knew that's what we wanted to do. And so the easy part was the getting the money. The easy part, which we didn't know was going to be easy was the number of companies we were going to see. And I remember Paul Judge, who's also on the investment committee with me, shared his email, Marcel shared his email, and we got all these emails. We've seen over 2000 companies. So obviously there's no pipeline problem. Look at all of you in this room. But two years ago there was sort of a question of whether or not are there enough companies to invest in?

Of course there are enough companies to invest in. And so that was much easier than we thought. I hope we've done a good job of following up with people and staying in touch with people and taking care of our founders. And some of them are in the room today. So if we've not done a good job, please complain and complain to me and tell me so that we can do better. And I told them when I said yes to this, on WhatsApp and I was like, I don't want to go to any meetings. I don't know anything about investing. I was still wrapping up at TaskRabbit and I saw ‘be on the investment committee.’ I don't even know what that means, but I'll do that. And I've always seen myself as an operator. So when I joined this investment committee and we're talking about forming the fund and structuring things and seeing deals and approving deals, what became intellectually interesting and was hard for me was saying no and having a really good reason for saying no.

Because we had heard that a lot of founders would get a no from a firm and some blanket answer, some two sentences. It was lame. And I would read these things and I'm like, ‘we actually have to give people the real feedback.’ ‘Well, you can't give the real feedback because you never know if you're wrong.’ And I was like, ‘you could always be wrong, but if you're not honest, why would somebody come back to you anyway? So that was a hard part of figuring out how to communicate in an ecosystem that sometimes lacks honesty and the ability to really be truthful in a pass, in a no. The other part that I enjoyed the most is working with our portfolio founders and that was where my operating experience was exciting, and I was really interested in sitting with them and talking to them.

And I realize that I don't have to be in the seat to be valuable and to be helpful. And when you are a CEO, you take on this role of ‘my impact is in this seat, this is how I can be valuable and most helpful’, but I'm not in the seat, I'm on the board. I'm advising and if I can help you not make some mistake that I made five years ago or skip some steps in hiring or making a partnership decision and that changes the trajectory of your business or honestly helps you sleep better tonight, that is a wonderful outcome for me. And so, I was worried that I wasn't going to find fulfillment in doing investing work because I was so used to doing the thing myself and I found a lot of fulfillment in it.

DAVID STIEPLEMAN: Oh, that's interesting. Can we go back to the past, to the evaluation of the founder, the team, the idea, there's this myth of the founder, which I find incredibly annoying. Like the obsessed guy usually with tasseled hair, Zuckerberg showing up in his pajamas, (I'm probably not allowed to say that in Silicon Valley), but anyway, that's the story and it's annoying. And is that annoying to you? Is that part of how you evolved, as your screen, your filter? How has that evolved as you've seen thousands of companies?

STACY BROWN-PHILPOT: The beauty of having fund managers on the other side of the table who look like you are that's not even part of the conversation, right? We don't even know those people. We didn't grow up with those people. We know our version of that or framework around that is people who have worked hard, who've shown grit, who have perseverance. We know that when a founder comes in the room who's a woman or a black person or a Hispanic person, somebody of color, you have worked twice as hard to get there and we know that because we've worked twice as hard to get to where we are. And so that lens alone changes the, ‘oh, we just want this typical Silicon Valley profile.’ No, we actually know the hardest working people are the people who had to work twice as hard to get anywhere that they are today. And those people are going to work twice as hard to turn the 10 million that you give them into a billion-dollar company. That's the difference.

DAVID STIEPLEMAN: You were talking about helping portfolio companies as an operator and you being in different seat but being able to have impact and presumably across a broader portfolio. Let's talk about helping portfolio companies replicate social capital. How do you do that?

STACY BROWN-PHILPOT: Yeah, we, we work with them quite a bit to create a community within the opportunity fund portfolio. We have a value creation team that does that. And part of it is when you're going from a founding stage of company or C stage, which a lot of our companies are, to raising that A, you're also getting to the stage where you need to hire executives and senior people in your company that you might not have a network with today. That first head of sales that maybe your co-founder and you are doing all the coding, but you really got to put somebody in this role. And if you don't naturally have those networks, the pool of talent that you have to choose from is much smaller because you're a startup and you're competing with all the other startups and you're competing with Amazon and Google and Facebook with their high salaries. And so really it's your mission, it's your vision and how you communicate that narrative. And so part of what we do with our portfolio is help them understand how to communicate that narrative but also build the network and build the relationships so that when it's time to make those key hires, they have a bigger network to do it.

DAVID STIEPLEMAN: One thing that surprised me about going through the pandemic as a co-leader of a business is how much performance matters because you have to emote and we had to do that over screens, which is very, very hard. You clearly had to do that and, and you famously have talked about having your true self out there was something that you had to get used to and you had to do that in a packaged way. How did you do that? Is that a natural skill? Did you learn it at business school? How did you do that?

STACY BROWN-PHILPOT: Yeah, I grew up learning how to be myself and then I started to work, and people started to fit you into certain molds. ‘If you're going to be at Goldman Sachs, this is how we do things.’ ‘If you're going to be at Stanford, this is how we do things.’ ‘If you're going to be at Google, this is the “Googly” way of doing things. And then one day I just realized how exhausting it was to try to be something other than who I was. It was very tiring. And so, I just tried on me, one time, and that was when I started wearing my hair natural at Google and I was like, ‘I'm just going to try on me, see what happens.’ And it worked out. People were treated me the same and I felt better. It just worked out.

And I think some of it comes with age and time. So, I remember when we were going, it was June and we post George Floyd murder, and we were on Zoom trying to have conversations about what had happened. And I, in 2016 had already gotten up in front of the company in person when we had Philando Castile get murdered just talked about what it was like to be a black person in America in front of a company where, at the time, we were about 6% black now that (we had grown since then). And they were so surprised that the CEO of the company would share such a thing. And this was, I became CEO in April of 2016 and this was July. This was two months. I'm the newbie in the job, but when I did that, it brought me so much closer to the team.

They understood and could really see me for all of who I was. So, when 2020 came, we didn't have to do a whole lot of conversations to get to the real issue of what was going on. And allowing yourself to be really seen as a leader may feel extremely vulnerable, but people will show up immediately and rally and help you and believe in you and have conviction in a way that you can't possibly imagine if you don't do it. So, there's some how in there and there's some why and it's a scary thing of the why, but the other side of it is a more trusted community, which is your company. by you just showing up and being who you are and then you're less tired. You're just like, ‘I'm just who I am.’ And you can focus on other things too.

DAVID STIEPLEMAN: Next 10 years for you, what are you looking forward to?

STACY BROWN-PHILPOT: Well, I have an 11-year-old and an almost eight-year-old, which means in 10 years, I will be an empty nester. I can't believe it. I was the person who wasn't going to have kids at one point and then they came and now I'm like,’ they're going to leave me in like 10 years.’ So, I want to be a good parent. I want to figure out how to teach my daughters how to live great lives for themselves and other people. I think what Sean is doing and all of the people who've supported him, including you David, is so important because we are changing the face of wealth creation and it has to happen one person, one organization at a time. Somebody said there's 70 trillion dollars that you can invest, and I don't even think that, you know, diverse communities – the percentage isn't even worth talking about. It’s less than 1%. And so if we can make a small step to making that number greater than 3% in 10 years, that would be miraculous.

DAVID STIEPLEMAN: Got a little bigger this week, but only a little bit bigger.

STACY BROWN-PHILPOT: A Little bigger, a little.

DAVID STIEPLEMAN: Detroit Pizza. That's a thing. . I did not expect that , should I get involved in that?

STACY BROWN-PHILPOT: You should get involved in that. Definitely.

DAVID STIEPLEMAN: Okay. Would I have to go to Detroit for that? I suppose I do.

STACY BROWN-PHILPOT: There's some places in San Francisco. I can give you a list. But you should go to Detroit. The bread is different in Detroit because the water is different.

DAVID STIEPLEMAN: This is the old, this is the New York bagel thing now. It the Detroit pizza thing. You got it.

STACY BROWN-PHILPOT: It’s true! I mean the New York bagel tastes different than any other bagel in the country because of the water. It's like that. Someone's agreeing with me.

DAVID STIEPLEMAN: This is a delight. Thank you so much for doing this. I love talking with you and, happy birthday.


DAVID STIEPLEMAN: That was Stacy Brown-Philpot. We spoke at the Concrete Rose Summit in Menlo Park, California on October 21st, 2022. We are so appreciative of Stacy's time. Here's what I think we learned. One: fear can be an asset. Stacy talked about the times when she stopped feeling that she was at the precipice and pushing herself further. That's when she knew it was time to go do something else. Getting comfortable, being uncomfortable can be a great thing. Consider embracing it. Two: values matter, and the values of an organization formed in advance prove their worth in a crisis. Whether it was responding to the murder of George Floyd or deciding whether or not to keep TaskRabbit open during COVID, Stacy and her leadership team leaned heavily on the values they discussed and practiced and lived prior to having to make decisions in more difficult moments. Finally, and this is something that we've talked about before, it's important to be intentional in the context of building relationships. Quoting Stacy directly, she said ‘Relationships are really about being thankful for the opportunity to interact with somebody. It's about how you build personal relationships over time and really get to know people and that's how you form authentic partnerships.’ Thank you to Stacy, in particular, for spending her birthday with us. And thank you to Concrete Rose for doing what they do and allowing us to be part of what was really an incredible event. We look forward to many more in the years to come.

You’ve been listening to ‘It's Not Magic’, a Sixth Street podcast. You can read more about our guests on and subscribe wherever you get your podcasts. If you enjoy today's podcast, please share it, and follow @SixthStreetNews on Twitter. For more on the show and our firm. Thanks to Sixth Street's production team, Patrick Clifford, Ritvi Shah, Kate Hanick with Sound Engineering by Stephen Colon. Our theme song is ‘It's Not Magic’, an original song from Patrick Dyer Wolfe. Once again, I'm David Stiepleman. Thanks for listening. The views expressed in this podcast are not necessarily those of Sixth Street and Sixth Street is not providing any financial, economic, legal, accounting, or tax advice or recommendations in this podcast. In addition, the receipt of or listening to this podcast is not to be taken as constituting the giving of investment advice by Sixth Street. Please see additional disclosures on our website for more details.

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