Full transcript: TaskRabbit CEO Stacy Brown-Philpot on Recode Decode


“When I go home to Detroit, there are people who don’t know they can become the CEO of a tech company.”

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On a recent episode of Recode Decode, hosted by Kara Swisher, TaskRabbit CEO Stacy Brown-Philpot explained why everyone should talk about diversity.

You can read some of the highlights from their discussion at that link, or listen to it in the audio player above. Below, we’ve posted a lightly edited complete transcript of their conversation.

If you like this, be sure to subscribe to Recode Decode on iTunes, Google Play Music, TuneIn and Stitcher.

Transcript by Celia Fogel.


Kara Swisher: Today in the red chair is Stacy Brown-Philpot, the CEO of TaskRabbit, who I’ve known for a really long time. She’s a former Google exec and the founder of the black Googler network. She joined TaskRabbit in January 2013 as its chief operating officer, and was named CEO in April of this year. She’s also on the board of HP. Stacy, welcome to the show.

Stacy Brown-Philpot: Thank you.

What part of HP are you a board member of? There’s so many parts of HP now.

There’s two parts. I’m on the HP Inc board, which is the business that sells printers and PCs.

Yes. Okay. So we’ll talk about that and a lot of other things. But let’s talk about you first. You’ve been a long-time executive and entrepreneur in Silicon Valley. Talk about your history and how you got to where you’ve gotten, to TaskRabbit.

I came to Silicon Valley 16 years ago to go to business school at Stanford, and before that I grew up in the city of Detroit. And didn’t know anything about technology. No one in my family was an engineer.

So how did you get to it?

I ended up going to work at Goldman Sachs in investment banking in 1999 and worked on some tech deals, and I got real curious about all these …

So you were a finance person? Like an accountant, essentially.

I actually studied accounting in college. So I’m a CPA.

So you had gone to Stanford Business School? Or Stanford for undergrad?

I went to Penn undergrad and Stanford for business school.

Both business schools, really. Or oriented toward it. So you had not thought about tech? You were just trying to be an investment banker.

I was probably going to be an investment banker for my whole life.

So what knocked you off that? Just these deals?

I worked on some tech deals at Goldman Sachs, and I got excited just about how these companies were creating all this value and going public.

So this was in the top of the boom when you were doing this.

Yeah, 1999.

Yeah, yeah.

The very top.

So is that what attracted you to them? The boominess? Or what?

The curiosity about the value creation that was happening with companies that had very little money. I was in M&A, so I also worked on some non-tech deals, but these were like big businesses with real revenues and real profits, and we were selling those companies, and here are these tech companies. So I wondered, “What is it about these businesses that is creating the same value as a long-standing profitable company?”

Sure. And what was your conclusion?

Didn’t know. That’s why I came to Silicon Valley, to find out.

So you came to business school.

I came to business school.

And how was your experience there? A lot of people go to the Stanford business school and then run right out into Silicon Valley companies. Was that the plan?

It was the best two years that I spent. Undergrad for me in college was really about, you know, how do I become a professional. But business school for me was how do I become the person that I’m meant to be. And that sounds really cheesy and I know people from Stanford might say that, but it really was about that. I thought I’d go back into finance, I’d learn about technology and I’d go back into finance. And then I discovered this little company called Google and decided that this might be a more fun place to work.

So how did you get there? You were at Stanford. This was right around the early 2000s. It was early.

Yeah, one of my classmates went to Google right after we graduated and I said, “What are you doing?” I didn’t have a job yet, and he said, “Oh, well, I’m at Google and you should come and interview. There’s a bunch of people who are building this cool company, and I think you would have fun.” And so I decided to go interview.

What attracted you to it?

To the company?

Yeah. I started covering it in ’98 or ’99.

It was some of the smartest people that I’d met. It was 13 people that I interviewed with on my interview day. One day of interviews. Some of these people have gone on to be very successful in their own right. I just felt like I walked out of there with, “These are some of the smartest people. I don’t know if this company is going to be successful, but I think I’d have fun working here with these people.”

Right. So what did you do when you get the job offer?

So I got the job as the financial analyst — little me is a financial analyst — and I’m thinking like, “Here I am, a Stanford MBA, and here I’m going to be this financial analyst. Is that really it?” But I later learned that is probably one of the best career decisions that I made. Because I ended up working with Sheryl Sandberg on her team and being her finance business partner. And at the time, Google was 1,000 people. We didn’t have any infrastructure around finance, so it was less about the number counting and more about building an operation and building the finance function for a business that was growing like crazy. And that was fun.

So you did just the financial systems for Google? Just getting it …

I was in what’s called financial planning and analysis, sales finance. And so I built out all the budgeting, all the planning, all the forecasting and all the operations around the finance team for what was the online sales and operations group.

Which was the biggest group, right?

It was the biggest group.

And growing like crazy. Like the money’s coming over the transom like nuts.

I mean, eventually the online sales business became the majority of Google …

Once they did that deal with Overture, all kinds of stuff.

That’s right. It happened right after I joined.

Yeah. Which was critical. And problematic later, but also critical to their growth.

And made ads a real business.

It finally had a business rather than just search. Because there were a lot of search companies. Were you worried that search had been tried by so many and failed by so many? You know, there were so many different iterations of search that didn’t work.

I wasn’t worried about search. I was inside Google, and so I knew how much money the company was making every day because I was in finance. So outside-in may have looked like, “Oh, we should be really worried about search.” And inside it was like, “Wow, this is a business that people are showing up every day to use, and they’re clicking on the ads and they’re getting value out of it, and no one can really stop this.”

Did anyone wonder why you worked there? Like your family or anyone else?

Oh yeah.

Because you were at Goldman Sachs, that’s sort of like the traditional route.

My mother said, “Well, you know, honey, if this Google thing doesn’t work out you can always go back to public accounting.” Crazy. But she didn’t know what it was. In 2003, it wasn’t a done deal, it wasn’t solved, it wasn’t figured out. And where I grew up in Detroit, nobody knew what Google was. No one was searching for things on the internet all the time, and if they were doing anything, they were doing it with Yahoo, which was a different company at the time.

Sure. Yeah. And Google powered Yahoo, if you recall. I remember having an argument with Jerry Yang: “Get them off of here right away, because they’ll kill you.” Those letters are very attractive, those colorful letters. Talk about the culture there then and working there. What was it like?

It was — everybody at Google still is, I think, at least from what I hear — very collaborative, pretty consensus-driven. We all want to solve the world’s problems. Organize the world’s information. Aspire to something bigger than yourself. And we’re all going to do it together. And that was just a part of the culture. We thought about … everything’s about having fun, all the time. And we worked hard. So we worked hard and we played hard but it was really about, “How are we going to do something that’s bigger than ourselves?” And we would set these big goals that we were pretty sure we weren’t going to achieve, but if we aimed high and ended up just a little bit below that, then we would accomplish something big.

Sure. I always thought that Google was the most dysfunctional group of people who function well together. You know? Like the functional dysfunctional.

I think we all had an idea about how we wanted to do something. And they were so different — the ideas were different. Which may mean the dysfunction that you’re talking about. But we somehow, you know, they did something with the hiring process that allowed us to get along. And we didn’t scream at each other, we didn’t yell. At least not in the early days. And so we’d just make it happen.

So you were there for how long? How long were you there for?

I was there for nine years.

And why did you leave? That’s a long time somewhere. I guess that’s why.

It’s a long time.

What happened? What caused you to say, “Enough.”

I loved working at Google, but it was time for me to go on to the next thing. I had accomplished so much: I started in finance, I had moved over into operations, I had moved to India and run a team of 1,000 people. I came back and I was an entrepreneur-in-residence at Google Ventures. I had tried a lot of different jobs there, and for me, my next thing probably just wasn’t going to be at Google.

You didn’t want to move up the chain there?

Google was now 50,000 people. So 1,000 to 50,000. I was more excited to go back to a smaller company that had a big mission and start to build that again.

And so you looked around, obviously. Google people get job offers everywhere.

I looked around. I actually had met Leah from TaskRabbit a year before and just tried this service, my daughter was five weeks old. And every time I meet a new entrepreneur, I always use the service or try the product or check it out and see what it’s all about. So I sent somebody to Target to buy some things for me and in two hours this person shows up and I was like, “Wow, this is something different.” So fast forward a year later, I was visiting TaskRabbit’s building and I saw the company was there. I checked in with her, and she had just kicked off the COO search. And she said, “Are you interested in being a part of the process?” And at first I said, “Maybe, but let me find out what’s going on with the company.” And they were really onto something. And I said, “Here’s another company with this big mission to revolutionize everyday work, and here I am looking for a company with the big mission that can scale.” And this was a business that is powered by people. This was an operation. And my entire skillset is all in operations.

So talk about that a little bit. The idea of this sort of sharing economy kind of thing is just getting started. But it’s a very analog kind of thing that you’re trying to digitize, essentially.

“The sharing economy” is sort of an old term now that, you know, fast forward eight years [from] when TaskRabbit was founded. What we’re really trying to do is create opportunities for people to earn a meaningful income and do it in a responsible way. I mean, I think of TaskRabbit as everyday work for everyday people. And I get to sort of build a business where we’re matching people every day who have time and skills to get something done …

Whatever it is.

… and people who need something done around their house.

And why is that a technology company? I mean that idea. And I want you to get more into the idea of what TaskRabbit is and isn’t. Because it’s hard. I think a lot of these companies, they just put digital things around what is, again, an analog business.

I like to say — and I talk about this actually with HP — TaskRabbit exists because of the technology that has been created. Because of mobile technology, because of the internet, because of location-based services, we’re able to now build a platform. We can connect people in a way that we couldn’t before. So we haven’t built the technology, but because the technology exists, we can enable people to do things that they couldn’t do before.

Right. And so you started as COO. You guys raised how much money?

We’ve raised $50 million.

$50 million. One of the more prominent ones in this area. Why don’t you want to call it the sharing economy anymore? Is it just not that? How do you describe it, now that you’re the CEO?

I like to describe TaskRabbit as the leader in on-demand home services. We’ve moved from, you know, neighbors helping neighbors to being a business where you can get home services on demand. You can download our app and use it and actually find somebody to clean your house or find a handyman in less than five minutes, 80 percent of the time. And that’s very different than the original construct of the sharing economy. Underneath all of that is this bigger economic responsibility, and I think some of that conversation has been lost. We believe that we have to empower people to find meaningful work. We have over 55,000 registered Taskers in our community, and they’re using TaskRabbit to pay one to three major bills a day.

Well, we’ll talk about the controversies around that too, because some people feel like it’s changing the way jobs are. We’ll talk about that in a little bit. But when you’re talking about the company, you’re the COO. There were some bumps along the road while you were trying to do it. Talk about those a little bit. And then you became CEO. Talk about that journey.

Yeah. There was some bumps. I got there and then, six months after I’ve joined the company, I realize that we weren’t focused on the most important things for the business. So we had some layoffs, we actually pivoted the business model and focused on a direct-hiring model. And it took a year to make that happen.

What was the problem? Explain that for people. I know you all like to use “pivot,” but something didn’t work.

We went from offering everything for everybody, and in doing that, [there] was like a 50 percent chance that you’d actually get your task done on TaskRabbit. So we said, “That’s not going to work. We actually need to —”

Because people feel dissatisfied.

They’re either very happy or very dissatisfied. You couldn’t build a scalable business that way. So we shifted to: We’re only going to offer a few things. Four things that you can get done around your home: cleaning, handyman, moving or delivery. And we’re going to focus on specific markets to make that happen and increase the chances that you can get it done. So now it’s like an 86 percent chance that you get it done. By doing that, we were then able to reinvest money into marketing and growing the business, increasing our density and penetration in those markets.

Where happiness and payoff come together.

That’s right.

So for people who don’t understand, how do you all get paid? You’re a matching service, essentially. You’re matching people. What is your part in it?

We take a fee on every transaction. So once you post a task on TaskRabbit, in a few minutes somebody will accept that task.

Like an Uber or whatever.

Yup. Somebody completes the job and then we take a transaction fee once that job is completed.

And then from who? Which side?

From the client. The buyer.

Yeah. So in making it small in some areas, is that in order to expand again or not expand again? Do you think you just have to pick, as a company, what you want to do? Because tasks could be anything. You could do everything.

Yeah, one of the reasons why we focused on a few categories is that we wanted to make sure we had enough Taskers — or supply, in marketplace terminology — to actually do the job. And so by focusing, we know how to find great handymen and great cleaners. A second reason why we did it was so that we could actually market the service to people in a clear way that they would understand it. Couldn’t go to market with, “We do everything.” What we can go to market with is that, “We will clean your home, we will do your chores while you live your life,” and it made a much easier kind of value proposition for people to understand. And that can expand. We’re only in 19 cities right now. We’re only in one city outside the U.S. We want to be in more markets. I believe TaskRabbit should exist everywhere. And so we can take our home-services platform and launch more markets. And then over time we’ll add more categories to it.

There’s been a lot of niches in this area, too. A lot of different cleaning, some of which are better than others, washing services, that do little discrete pieces of this. How do you compete with those?

One of the things that we’ve learned from having multiple categories is that our clients come back and use us more often when we actually have more services. And so people who’ve come up with verticals are trying to do the same thing by adding other verticals. We already have them.

Right. You already have them. But [are] there too many of them? Do you look at the market? Because there’s been a lot of companies in this market and a lot of them are closing down or failing.

Yeah. I don’t know if there’s too many. But we don’t see it as a problem in terms of our growth. We’ve always had positive unit economics. We’re profitable in every task in every category, and we’ve always been that way.

But you’ve raised this enormous amount of money.

Yes.

Profitable in every task. Does that mean profitable as a company or profitable as a … ?

Our gross margin. Contribution margin profitable.

So talk about your transition as COO to CEO. Why did that happen? It was April?

That was in April. But Leah and I had been talking about it for months. She came to me and said — we had reached a point where we grew 4x last year and we had reached such a good point of scale — and she said, “Look, this is the time where I’d like to step aside and let you come in as CEO. I’ll become chairwoman of the company and you can take the company to the next level.” It was a pretty amicable decision. We went to the board, the board said, “This is great,” and it happened. There was the logistics around announcement that you all didn’t see in the background, but it was sort of several months of planning that went into it.

Had you wanted to be a CEO? Everyone wants to be a CEO presumably, or not. I don’t. But did you?

I don’t think everyone wants to be a CEO [laughter]. I didn’t know I wanted to be a CEO until I was offered the job. I was very happy running a great company with a great partner. When the opportunity came up, I felt like there [were] things that I could do as CEO of TaskRabbit that would make the business successful. I just wanted TaskRabbit to exist for everyone.

That you would have all the handles and all the ability to do things there.

My experience at Google going from 1,000 to 50,000 people has taught me a lot of about growth and scale. We’re at a point in the company where that’s exactly what we’re doing. And so I could apply all of that to this great business. And thought, “Okay, yeah, I want this job as CEO.”

So what’s been the hardest thing for you since you’ve gotten that job?

Prioritization of my time. That’s been the hardest thing.

Meaning?

You get asked to do a lot. And the most important thing that I can do is make TaskRabbit successful. But knowing on a given day which one of those things actually will make that happen, it’s hard to decide.

Right, right. So what do you think your biggest task is?

Growing the company.

Meaning in new places and new categories and improving.

With new partnerships and expanding into new markets.

You are in a genre. And again, you don’t want to call it a sharing company. What would you say you’re in? Service, or what?

I think we’re in the sharing economy, but we’re a home-services platform within the sharing economy.

In the way Uber is a car service or whatever it calls itself today. What do you imagine is going to happen with all these companies? There’s so many of them. There were a lot started, now the pace is going a lot slower in every single genre available. I think there’s not one — food, parking, home services, cleaning, washing, drinks, everything else. You know what I mean? What’s happened here and where does it go? Where’s the next place for it?

I think there’s going to have to be some consolidation. What I think is happening is that on our mobile phones today, we have a lot of apps that we use. And over time there’ll just be fewer that we rely on. And so what we’ll have to do as service providers on those apps is provide a better offering. And for us, it’s life essentials. The consolidation will happen. I don’t know what happens to the companies in that consolidation, but I think there’ll have to be at least some consolidation in the market.

Has there been too much expansion? Too much money thrown at this?

Maybe. I can’t …

You’re a financial person, you can answer better than that.

You know, I can’t think about other companies. I think that we’ve always thought about having strong unit economics. And so the timing with which we’ve taken money and taken investment has really been built on, “Have we reached the next stage of growth? Can we grow the business with the unit economics that we have in a consumer business?” And I don’t know that every company has thought about the way they raise money, and likewise the investors have thought about the way they’ve provided the capital.

That’s called rigor, actually. Rigor of understanding the money. So what your concern with is not so much the category, if it exploded or it starts to get weak in certain areas. It’s how you manage your place in the category.

That’s right. I mean, home services is a $400 billion market. So we’ve got a lot of —

It’s mostly dissipated now. I’m trying to think, there’s Angie’s List. There’s all kinds of things that are in the home services. Who do you consider a competitor?

Most of our competition is people doing it themselves. They decide, “I feel guilty,” or “I could do this myself.” And we want TaskRabbit to be the trusted place where they go.

That’s the platform.

That’s the platform.

The workers themselves.

And we want the clients to think of TaskRabbit when they need their house cleaned or they need a handyman. There’s certainly other companies out there that do that. Angie’s List is an example of a lead-generation opportunity. We think we’re different because you actually can hire the person on TaskRabbit, you know who’s going to do the work, you know how much it’s going to cost. It’s a very different new version of what they have. [Theirs is] what I think of as an old business model.

So let’s talk about the changing economics of jobs. Because you are a job company, you’re creating jobs for people. There [have] been a lot of controversies around this. Some people think, you know, everyone in Silicon Valley is, “it’s the best thing ever, everybody gets to work whenever they want.” That’s the Uber argument. But there are trade-offs about what happens to jobs in this country — they’re not unionized, there’s not as many rights, the health care issues. Let’s go over some of the more controversial aspects of it. Obviously I think you’ll be on the side of, “This is fantastic,” just the way I recently had Sheryl Sandberg onstage talking about how AI is fantastic and there are some that beg to differ. Talk about both sides. I get the plus side, that anyone gets to work whenever they want, they get to earn a living or extra money if they’re a mother or, you know, whatever, you’re a college student, you need extra money to do these things and you have skills. That’s the plus side.

So let’s talk about the Tasker side. When I grew up in Detroit, I came from a working-class family and people.

What did your parents do?

My mother was a single mom, and she was a claims adjuster at an insurance company. She actually dropped out of school — she was going to become a registered nurse — because she had to take care of me and my brother. And she didn’t have TaskRabbit. There was no service available for her, so she made a bunch of sacrifices for us.

So if TaskRabbit had existed? She would fall asleep helping us with our homework. What if there was this service that could help her get things done so that she could spend more time with us? And that just didn’t exist. I know that there’s a lot of controversy around this, but it means a lot to me. Likewise, I grew up with people who couldn’t find jobs. They couldn’t find W2 jobs. They were hard-working people with great work ethics. In Detroit, the auto industry went away for a long time. It’s coming back now, but it went away. And these are hard-working people. And so they would do anything to create a side hustle.

And what TaskRabbit has done, and many other sharing economy companies, is actually formalized the side hustle in the sense that we are now giving people a way to earn an income that is meaningful. We don’t set our hourly rates below the average minimum wage for the country. So the minimum amount you can make on TaskRabbit is the highest minimum wage in the country.

[Highest minimum wage] is in California, right?

In the country. Which is California. So anybody, anywhere, [in] any one of our 19 markets will never make below minimum wage. We did that because we knew that people were depending on TaskRabbit for a living. We were becoming a social safety net and we wanted to provide people with livable wages. So I think about this as more than just the flexibility that they have but it’s coming to a place where you can make a thousand dollars a month to pay two bills and before that you would either go into debt or have to go borrow the money from someone else. How fulfilling is your life now because you’re not going to borrow and ask for money, you can actually go make it on your own with the skills that you have.

So a lot of people though think it’s hollowing out the job market. That eventually we’re going to be in this sort of weird servant [economy]. The joke that I make is that San Francisco is assisted living for millennials. You know what I mean, whatever they want is available to them. And these people have means and money to be able to afford this. Not everybody does, for one. And for two, it hollows out the job economy, where if everything can be TaskRabbited — I don’t know if that’s a verb — you create, you know, not enough regulatory structure, not enough rights for workers, you don’t get regulated enough. I know that’s an anathema to Silicon Valley people but there are some good parts of regulation that do protect workers.

Yeah. We are not against worker protection at all. In fact we have a $1 million insurance policy that protects our Taskers who do the work and our clients who get the services done. And so we’ve been cooperating at all levels, the federal, the city and the state level of government to make sure that whatever policies come about are policies that are informed. They’re educated about how our business will work within those policies in that they actually protect the workers. So we are not against worker protection. I think the hollowing point is one where I often struggle to answer that question because I’m not in a generation of millennials who see the world in a different way.

What TaskRabbit is trying to do is embrace the fact that we do have a community of people in cities like Chicago — let’s go beyond San Francisco for example — and cities like D.C., where they’re choosing to work in a different way. And over time there’s a structure to their lives that’s a whole lot more flexible than the one that I was expected to grow up in. And so to the extent that we can 1) enable that, I think that’s great, and 2) work with the regulatory bodies to create whatever regulatory frameworks that allow these companies to be successful but also allow people to find work and have meaningful jobs, then I think that’s a good thing.

Gavin Newsom, who’s running for governor of California eventually, talks about creating a whole new regulatory framework around work. What has to happen around work? Because in a lot of ways you could think of, you know, Larry Page [who says] it may be that everyone’s not going to have a job. Job creation is really hard and when you hear the government saying “We’re going to create jobs” like right now in this whole election, “We’re going to create more jobs.” Governments can’t really create jobs anymore. Or they can but it’s not quite as easy as it was. How does that happen if everyone’s on a part-time TaskRabbit kind of world?

I think that one of the things that has to happen is the concept of part time should be better understood, because the people who task on TaskRabbit are Taskers, they have full-time jobs. It’s just not the same job. And they’re defining it: “I want to work 50 hours this week and 30 hours next week and that’s how I’m going to pick up my kid from preschool or daycare,” for example. And so one of the things is the definition of a part-time job and how that’s classified is one thing that needs to change. The other one is just training. Can the government create jobs? Is it the company’s responsibility to create jobs? One of the things that we struggle with is we want to be able to provide more training to our Taskers. Like, I know how to drill a hole into a brick wall and I want to be able to drill a hole into a concrete wall and I need to learn that skill. How do we do skill development and who supports that? That’s a service that could be joint, it could be something that we provide or it could be government led.

But the definition of what jobs are, it’s not going to be the same, presumably. And that’s the worry a lot of people have. It’s been a pretty good system up until now and now it’s a little bit blown apart.

I think it’s a worry because we don’t know where it’s going to end up. But when you think about it, there’s one million freelancers today and by 2020 that number could be as high as 40 million. People are finding a way to make money. And if the current structure isn’t supporting that, they’re finding another way.

Can you imagine a world without permanent jobs?

I could imagine a world where your choice of a permanent job is not as long tenured as it used to be. I definitely can imagine that world.

And what protections need to be in place then, from your perspective? As someone who’s running one of these companies.

I want people to feel like they can retire when they want to retire. I want people to feel like if they break their wrist or they get sick, they have health care to take care of their children. I want people to feel like if I need to take a vacation I can take a vacation and I want people to feel like if I want to learn and I want to grow and develop as a learner in this job, I can do that.

So what responsibility do you and the Ubers have? Because Uber has more of a “meh, whatever.” It seems like it. I know they try to say it but it feels a little bit like “you’re on your own, Jack” kind of thing.

This is a responsibility that we take very seriously. We have so many stories of Taskers who actually use TaskRabbit to fund some of these things like their college education or their children’s college education. And so we see ourselves as having, you know, an economic responsibility to make sure that our platform is a place that they can earn a meaningful income. And working with whatever regulatory bodies are willing to sit at the table and have a real conversation about how to do that.

Are they still hostile? Because there’s some hostility, obviously.

We’ve never experienced any hostility. So I don’t know if you give hostility you get hostility, but we’ve always just raised our hand and said, “We want to talk.”

How much time do you spend on regulatory issues?

We have a team that focuses on it. I spend maybe 5-10 percent of my time on it. But we have a team that focuses on what are the regulatory issues and how do we educate people about them.

It’s really coalesced around cars, for some reason. It’s really interesting, all the regulatory fighting that goes on. Maybe you’re right. Maybe it’s the companies that are doing it in that way. Last question on this issue: You’ve improved your app, you’ve improved the experience on your app, what do you think the most important thing going forward to this sector is? What is the next iteration from that?

I think that the beyond app consolidation and becoming the primary use on your home screen, we think that the technology around voice and messaging will be the next destination, so people ask for getting something done.

Such as? Explain.

So you’re in your kitchen, you get off the phone with your mom and you say, “Alexa, can you reschedule my weekly cleaning to Saturday because my mom’s coming early?” And so now your regular Tasker who comes and cleans your house on Sundays will now come on Saturday to do your house cleaning for you. And so what has to happen is that our service needs to evolve so that it can embrace new platforms.

Are you doing that now? Are you creating it?

We’re working on it.

We’re working on it. Are you on Alexa right now?

No we’re not.

You’re not? Oh I like that. Because you know I love my Echo. I’m the Echo lover of all time.

Do you?

Oh my god, I met one of the guys who designed it and I nearly salivated over him. [SBP laughs] And now they have a music service, I don’t know what I’m going to do. I ask it to do a lot of things. I would like it to be able to do other things. But you’re right, voices are really interesting and it hasn’t been iterated. Google hasn’t iterated it, Apple hasn’t iterated it very well. Siri is fine, kind of not good. So voice and messaging is the next thing. What else?

And then just growing TaskRabbit in new markets. We have a playbook where we understand what makes a big market successful and a smaller market successful. There’s a cultural adaptation to going into every market. And so we’ve now got to figure out how to take that playbook and launch in new markets where the cultures will be different.

So where are you now abroad?

We’re just in London.

London. Where else are you going?

We want to go into four more markets. I won’t talk about each one.

All the ones, all the ones. Yeah, Germany should be interesting.

You think so?

Yeah.

Why?

I don’t know. I don’t know the cultural things of asking for people in your home. You know what I mean? I think that’s one of the things. You know India well. It’s a very different set up in how people work there. And they have a whole structure there around working that is a little bit odd, you know what I mean?

Yes, yeah.

It’s all status- and class-based at the same time. So it’s a really different kind of thing.

Surprisingly though we get a lot of interest in TaskRabbit in India.

Really? Interesting. And then in this country, where would you like to expand to? Just more cities.

More cities.

More cities. What’s your most important cities? San Francisco?

Well our largest market is New York.

Ah, okay.

And it should be, the population’s bigger.

And they can’t do anything there.

It’s just bigger! The numbers are bigger in New York [laughs] But San Francisco is a big market for us too.

I’m going to do an experiment and have Taskers do everything for me for one week.

You should.

It would be really interesting to see if they could actually accomplish anything. You know I don’t shop anymore, I just do Amazon.

What’s everything?

Everything. Just whatever you do. Not other things. I have other means to do that. But you know, I’m not going to go into that [SBP laughs]. We’re speaking with Stacy Brown-Philpot. She is the CEO of TaskRabbit and when we get back we’re going to be talking about Silicon Valley, being a woman, and other things here, and a CEO. You’re kind of a unicorn, Stacy.

Oh boy. Unicorns.

Yeah, you’re a unicorn in many ways. You’re also on the board of HP. What’s that like? That must be interesting.

Perspective.

Yeah. Who’s the CEO, is that Meg?

Dion Weisler.

Dion, that’s right. That’s the other one. How did you get on the board there?

I actually got a referral to the recruiter who was doing the search from Clara Shih, I don’t know if you know Clara or not.

Yes, of course.

And I met with a recruiter. It was right as HP was splitting into two. So they were reforming the board. Meg was spending a lot of time focused on diversity and creating a very diverse board and so there was a broad section of people that they were looking at. And so I went and I interviewed with Meg and with Dion and the rest.

Something they find hard but isn’t, actually. I was talking with Tristan about this.

It’s not that hard.

No, you’ve been hiding in plain sight, right? [SBP laughs] So let’s talk first about gender, because there’s not many women CEOs — fewer and fewer, actually. There’s lesser and more and many. How is that? Is that different for you? Or do you just not think about it? I always am curious.

I don’t think about my gender. I think about the combination of being a black woman. And it’s really hard for me to separate the two.

Who else? Who else is a black woman? Ursula?

I friend of mine named Shellye Archambeau who’s at MetricStream, an enterprise software company.

Any other people of color” There’s the CEO of Pepsi.

Yes.

But not a lot.

Not a lot.

Not a lot. Why is that?

I don’t know. I really think that there hasn’t been enough role models for CEOs. I remember when I went to India and I showed up and it was … Ursula had just been named CEO and no one had a model for [it].

This was at Xerox.

Xerox, that’s right. And no one had a model of black women running the office for Google. And some woman came up to me and said, “So are you like Ursula?” [KS laughs] Because that was their model. And it occurred to me that there was no other model for thinking about it. And so you know, for me to become CEO, I now get to become a model for what other people can aspire to and what they should aspire to.

Do you want to be a model? You have to be or do you want to be?

I want to be and I have to be. It’s my responsibility and I own it.

So what is that like? What does that mean for you when you’re doing that?

It just means that I make time to talk to people. Every time I think about something that I’m doing, a decision that I’m making, I think about the impact that it will have on the community. I embrace involving myself in the community so that people can see those models. And you know, quite frankly it means I sleep a little bit less and maybe spend a little bit less time with my family but it’s important for me to fill that role.

Why do you feel like there aren’t as many? I know you say, “I don’t know,” but you’ve got to have thought about this. I’ve thought about it, we’ve all thought about it. What happens that there are very few women, very few people of color in tech. Google tried very hard to make itself more diverse, but I know they went to great lengths not very successfully. What is the problem? From your perspective. And there are lots of problems, I know it’s a complex issue.

Yeah. I think there’s two ways to look at it. The first is, does the culture of the company embrace the diversity. And embrace meaning are we a place where people feel welcome and they can bring their whole selves to work? And when they’re there, are we doing what’s required to pertain to the people who are there? And I don’t know if that has been thought about carefully enough. It’s something that I think about every day: Are we doing that at TaskRabbit?

When you say “not thought about carefully,” what are the mistakes that are made?

One of the things that I struggled with early on in my career was joining a company where it’s built on referrals, and the idea of hiring people based on your own network. If you actually don’t have a diverse network then you’re less likely to hire people who are diverse. And it’s much easier when you’re growing very fast and you need to just grab people. It needs to be an intentional kind of stated objective. The second thing is just around the pipeline. You know, I have been the only for most of my career. I walk into a room and there’s one black woman, or two black women, and there just aren’t that many because the pipeline of talent just isn’t there. And I know we overuse that word.

Yeah we do a little bit.

Like, “You just need to build a pipeline.” But the fact of the matter is, when I go home to Detroit, there are people who don’t know they can become the CEO of a tech company. And someone needs to invest in building that pipeline.

But do you imagine that it’s maybe made invisible? Because there’s a new movie coming out, all these black women mathematicians who were very critical to the space race. I know Megan’s talked about Katherine Johnson and others. Invisible. Critical.

I think you bring up a third piece that I hadn’t thought about until you just said that. It’s the role of media in highlighting who these people are, telling their stories, sharing their stories, and making those stories more public. I’ve never been in media so I can’t comment on the success or failure of that, but being able to talk about those stories is really important. When I was in high school we talked about black history a lot, but 98 percent of the people in my school were black, for example. That doesn’t happen everywhere. So I was saying at TaskRabbit, in our company, it’s less about the role of media and what role do we play in sharing and talking about the diversity in our company and making people feel welcome. A lot of the shootings that happened in early July, I got up in front of the company and I just talked about being black in America, and I just shared it with the company, no one else, and it opened up a dialogue. Those are horrible outcomes and horrible experiences, but it opened up a dialogue where people can start to really talk about it. And more of that needs to happen.

What did you tell them?

It really was for them. But I just talked about my experience growing up as a black person in America. And how when you see what was happening and police officers were shooting black men and then there was the retaliation that occurred after that, both of those things hurt, because, as my grandmother would say, people are sick and tired of being sick and tired. And it’s sad that we’ve gotten to this place in the country and that we need to find a way to heal. And I was afraid that healing wasn’t going to happen before more hurt happened to other people.

So what did you articulate about your experience? Giving them a new perspective, like you have to see it from a community that’s sort of preyed upon?

Yeah, my perspective of, I know what it’s like to be afraid of the police. And when you see a police officer you don’t immediately feel safe. You wonder what you’ve done wrong and what could happen to you. And that’s the world that I existed in. In a world where — and people have talked about this — you’re taught to limit your answers to an officer because you don’t how they’re going to treat you.

Right. Which I think people don’t even get.

No they don’t. And just me saying it in front of the company was eye-opening for so many people.

Right. “Whaaat, police officers are nice to us.”

Right.

Which I think is a different thing. Even hearing it from someone. Because I know people believe it in some way. Even if they’re told again and again and hear it again and again, because it becomes so politicized in a lot of ways.

Yeah, but it’s how you live. You don’t know anything different. Just like you don’t know anything different, this is how we grew up.

Right, absolutely.

SoI talked about that.

Yeah, I think it’s hard for people to talk about things. When we were covering the Ellen Pao trial, this is in gender issues, a lot of CEOs wouldn’t talk to me on the record about it. One of them said it was the third rail of discussion here. When it was gay issues they’d talk about it, they wouldn’t shut up. And they want their names attached to it. It was a really interesting issue. And race, forget it. They don’t want to get near that. I had an interesting lunch today with someone who needs to think about this a lot. And he’s a white guy and he said, “You know, I feel like when I say something I have to be really careful, I don’t know what to say.” You know? And this is someone who’s quite devoted to the issue. I said, “You’re just going to have to take the reaction for a little while.” I think once they get a little negative reaction, a lot of these white men in Silicon Valley, they get really nervous and instead of just pushing through the reaction, which is completely valid, it sets them back because it’s not, “Aren’t you nice to talk about this.” Like, “Thank you so much.”

My experience is that you’d be better off just talking about it.

Yeah, yeah.

Because it often is the elephant in the room and everyone else can see it and so I would like to talk about it.

Yeah. What can companies do better to encourage difference? Because here San Francisco is supposed to be that, right? Everyone can be different. But you really can’t. You know what I mean? It’s a really interesting thing. They use the word unconscious bias, but I feel like it’s conscious, I keep arguing that it is. I know there’s scientific studies that people don’t mean it but I think there’s ways to not mean it, you know what I mean? It sort of lets people off the hook. Well-meaning people. It’s often well-meaning people who don’t, on the surface, have racial issues. Like Trump supporters, when you see some of the vile stuff that comes out of their mouth, that’s very clear what it is. But here it’s a little harder to stop. Because it’s the same result, it’s the same result.

I think unconscious bias training is a good thing. We did it at our company and it was a request that came from somebody on the team, and after we had the session, every single person, regardless of color in the company, had a new awakening. They had sort of a different lens on how they saw each other and other people. So I would recommend that. I would recommend it and I also think that just being willing to talk to somebody who’s very different from you and learn about who they are as a person. That is really really hard to do. And I challenge people in my company to do that. Try to see me for who I am, try to see all of my differences and appreciate all of my differences. And it would be a forced dialogue, but we have to force ourselves to have that dialogue and not pretend like these things are okay or that we’re just trying to have a conversation.

Sheryl Sandberg talked a lot about being in a board meeting and always having to be the one to mention women’s issues. She feels at first very like, “Why do I have to be it?” And then she’s like, “Ech, I guess I just have to do it.” You know what I mean? Like it’s sort of a “you just have to” kind of thing.

You do. I agree. I’ve been in board meetings and had to be the young person. Right? [laughter] And mention, “Well people will use this on a mobile phone and not on a computer!” Right? And we have no problem doing that, so why not bring up these other issues that are important to us and open up the dialogue around it?

Lastly on this issue, the election. How do you look at this?

My great-grandmother lived with me, so I had people in my house who, when they grew up, couldn’t vote. And so I just want people to vote. And I think there’s a lot of intensity around the election and people being frustrated and upset with the process that we’ve ended up with. I don’t have jobs, I’m not optimistic about the future for myself or for my children or even their children, but in the end, to abstain from voting is to deny yourself a privilege that not everyone in this country actually had. And so if I ask for anything I just want people to go and vote for someone.

I have a feeling who you don’t want to vote for, but I’m not going to ask you your political beliefs. I’m guessing. Let’s finish up talking about being an entrepreneur. Because it’s linked to it. You have to sort of take risks, you’ve got to be out there. Talk a little bit about Silicon Valley right now. How do you see the innovation cycle? You’ve had different perspectives at big companies and now a small company in finance. How do you look at what’s happening now? There’s been a lot of sales, there’s been a lot of shifts, and a lot of people declaring victory when it’s just a sale, essentially. How do you look at where we are?

You know, I’ve been out in Silicon Valley for 16 years. And it’s always changing. I don’t really appreciate the pace of change and innovation until I go somewhere else in the country.

Right, that’s absolutely right.

And so I go somewhere else in the country and they’re like, “What is this service that you use?” Some new thing that just came out that we’ve all been using for like nine months.

Like Slack.

“What is Slack?” That’s a great one. “Well I don’t even know how that works.” And so I think we get stuck thinking like there’s no innovation or it’s slowing or people are opting out and they’re selling, but we still are leading innovation. And there’s no question that it’s happening here. As a former M&A person, a banker from Wall Street, deals will happen. There will be companies who decide, bigger companies, “This is the way that we are going to grow. We’re either going to build it ourselves or we’re going to buy it.” They make build-versus-buy decisions all the time. And if that company can be successful as part of a larger business, that’s great. If they want to go it on their own, that’s great too. But I unequivocally think that this is still the place for innovation. Just go visit somewhere else.

Do you want to sell TaskRabbit?

I want to grow the company.

You want to grow the company.

I want to grow the company.

However way.

However.

However. And then as an entrepreneur, I always ask this to everyone. So you feel good about the pace of innovation, right? It feels a little tired right now for me, but maybe I’m just tired.

It may feel tired because, I don’t know, I’ve been here for a long time, but just to think back to a time when, I don’t know, just a few years ago we wouldn’t even have thought about getting in a car with a stranger.

You’re right, you’re right.

And now we hop in, we don’t even say “hi” anymore.

Is there an area you think is going to jump? Yeah, you’re right, you’re right.

So, it’s just like three years ago.

Yeah.

So I don’t think the pace has slowed at all.

Yeah, it’s sort of like the Louis CK joke about being in the plane and you’re using the internet and then you start complaining about the internet on the plane when you’re in the tube of death riding along doing the internet.

Exactly.

You know what I mean? “Wi-Fi! It just doesn’t work!!”

Wi-Fi, on the flight, for four of the six hours.

It’s a miracle. Last question: I ask about mistakes made. Give me one mistake you’ve made and if you’ve corrected it, that you’ve learned from, and then one thing you did really well. What do you think you did really well?

I made the mistake early in my career of not hiring senior people fast enough. So figuring out how to replace myself in a job. And I got that feedback in a very strong way.

From who? From Sheryl?

From Sheryl, yeah.

What did she do?

She said [laughs]… I had gone to her, I had hired this person and she said, “This person seems great. But they’re not your replacement. So what are you going to do? Because you’re not going to be able to move on and do anything else. You’re not creating leverage for yourself. But this is a great hire if you want to make that hire.” And I just walked out thinking I had the perfect candidate and I just was focusing on the wrong things.

Sheryl knows from leverage, doesn’t she.

From leverage, very good. And so the first thing I did at TaskRabbit and the best thing I did was hire my VP of operations who’s now my COO, two months after I joined the company.

Okay. So they could replace you.

So they could replace me.

It’s like having kids, right?

[laughs] That’s right. Yeah.

That’s interesting. So you don’t do that anymore.

I don’t do that anymore.

You just wait for someone to take over from you. And then what’s something you’ve done really well, do you think?

Joining TaskRabbit and really deciding to take a risk.

Big move from Google. They would have pulled you right up the chain, right?

Nobody thought that leaving Google was a good idea. Not in a bad way, but just like, “Why would you leave the company that everybody wants to go work at?” And I think that my life is more fulfilled because I’m working on a problem that’s revolutionizing everyday work and I get to talk about job creation and how it affects me and people that I grew up with. It’s so much more connected to who I am as a person and I love it.

When we talk about work-life balance and kids and things like that, is it worth it? Because I work a lot, too.

I think every day about, when I get up in the morning, I’m leaving my two little girls.

You just had a little kid, right?

I do, she’s almost 2. She’s not that young anymore, she’s growing up. But I think when I leave the house.

You have to stop feeding them. You feed them and they get big! What the heck!

They learn how to open the refrigerator and feed themselves.

Yeah, that’s true.

That’s a good turning point right there [laughs]. But yeah, every day I think about when I walk out the door, I’m making a trade-off, I’m making a choice, and is this the thing I want to be doing right now? And it is. And I don’t think about work-life balance because for a while it’s out of balance and for a while it’s in balance. And so I just live in cycles and I use TaskRabbit to outsource things if I can [laughter].

You have to, right?

I have to! And I’m just satisfied with not being perfect.

Yeah. That’s good for you. How does your mother feel about your decision-making?

She’s happy. She did say to me, “Well you know if this TaskRabbit thing doesn’t work out you can always go back to Google.” [KS laughs] But now that TaskRabbit has worked out she’s like, “Okay.” [laughter]

I wouldn’t take job advice from your mother. I don’t do it myself. Anyway, Stacy, thank you so much. You’re always delightful and congratulations on your job. I know I called you a unicorn, but it’s nice to see no matter how you slice it. I wish for your success, your great success. I don’t wish for everyone’s success, trust me on that. Anyway, Stacy, thank you for coming by and I really appreciate it.

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