On the Record: TaskRabbit's Stacy Brown-Philpot

Stacy Brown-Philpot became chief executive of TaskRabbit in 2016

This past week California voted in a new law designed to pave the way for gig economy workers to become full employees. That's a massive deal for the companies offering that kind of work.

Stacy Brown-Philpot is chief executive of TaskRabbit, an app where people can offer up their services for things like furniture building or help moving house.

Like Uber and other gig economy sites, TaskRabbit Taskers - as they're known - are treated as contractors, not employees. The new law, AB5, could change that - and make firms responsible for offering things like holiday pay and sick leave.

I spoke Stacy about the impact it might have on her business, and whether the gig economy is the future - though to be clear, our discussion occurred before the vote was passed a few days ago.

I also asked her what it was like being one of Google's first black employees, and her difficult and risky decision to dramatically change TaskRabbit's business model after she took over the company in 2016, which angered many of its users.

Anyway, as I arrived at TaskRabbit's HQ - which, as you'll hear, is next to an extremely busy road in San Francisco, one of TaskRabbit's' press team told me that Stacy often does some of the tasks for customers herself… so we started there.

• In-depth interviews with leading figures in the technology industry.

• Give feedback, or suggest future guests, on Twitter

Interview transcript (edited for clarity)

Dave Lee, BBC: What was the last task you did for a customer?

Stacy Brown-Philpot, chief executive, TaskRabbit: The last task I did was an Ikea furniture assembly. As you know, our company was acquired by Ikea in October of 2017. And as a company we task, and so one of the Taskers in our community saw that I had done a task before that, and challenged me to do an Ikea task. So I showed up with another Tasker to do a task at a family who just moved to San Francisco. The mom is a professor, the dad was taking care of the kids. One of the kids was at preschool and the other one got out early. So the little daughter was with us while I was assembling a chair and two bookcases.

Did that make things more difficult, having the small child, running around?

You know, she was watching TV, and so we got to watch cartoons. And he ordered her a pizza. And he was the client was kind enough to share the pizza and the soda with us. So it actually made it quite fun.

Did they know that you were going to be the Tasker before you showed up? Did they know that the boss was coming to do this?

They did not. I don't ever say who I am. If they figure it out, that's fine. I don't say it. But at the end of the task, I did share it with him. And he was very surprised.

I imagine people are always surprised, because it just seems like something that wouldn't be part of your day-to-day.

It's a lot of work to go into an uncertain environment, to not know that a child is going to be there or what their room is going to look like and where this stuff is really going to go. The other Tasker who was with me was very experienced. So I was paired with somebody who knew his stuff and knew what he was doing, so much so that he let me borrow his power drill. When he saw I was moving a little slowly, he said: "Why don't you try my power drill?" And he gave it to me. So he knew all the pro-tips as well. So, even I learned something.

Let's bring everything back to the beginning here. You were born in in Detroit at a time when the city was really starting to struggle. The auto industry was really beginning to not do well. And I think many people have a perception of what Detroit must have been like at that time. But I wonder what it was like specifically for you.

For me growing up in Detroit was... it was home. And we had a community. And while the auto industry was starting to decline at that time, people still looked out for each other. There were lots of Midwestern values of having a strong work ethic, taking care of the other person in the community. Making sure that we all got something when somebody didn't have it. And those values I still carry with me today. I mean, one of TaskRabbit's values is around being a better neighbour. And that really goes back to community. And how we had a community that didn't have a lot of resources, but we still looked out for each other.

One of your first jobs growing up was the same as my first job growing up, you did a paper round, and you did it with your brother, I understand... and this is precisely how I did mine. So I'm curious to know the differences between a paper round in England and a paper round in in Detroit. Tell me about that. What do you take from that?

My brother was the CEO of the paper round. It was his idea to get one. And he enlisted me to help out. So I was the CFO, I was in charge of the money and collecting the money, and making sure that people paid and when they didn't pay, you know, showing up with either a sad face or an angry face to collect the money. But I remember my mom in the winters would drive us every few houses, because it was so cold you had to get in and warm up just a little bit to go deliver a few more papers. It was freezing.

How did you get people to pay? What was your approach?

You were strategic, because you knew what time people came home. So you would catch them on their way home from work. And when they're getting out of their car you're like: "Hi, remember, you haven't paid for your paper round yet!". And then they look at you, and they see your face. And they know that they owe you the money. So then they just they pay it, usually.

They must have seen you coming and hid away.

They tried, but I would sneak behind brushes or you know, whatever was necessary to make sure we got paid.

I feel that this is one of those kind of cliché questions here. But from that paper round, are there ever times when you draw something from it in the job that you have at TaskRabbit?

I draw something from everything that I've done. We're all a function of the experiences that we've had, and that one I really draw on. You know, it's all about relationships, and the people that we had the best relationships with were the people who, you know, paid us on time gave us extra tips, got us Christmas gifts, all of those things. And so I invest a lot in the relationships. TaskRabbit is built on relationships. And so I work at a company and have the joy of working at a company that's essentially built on relationships.

We'll get to how you came to be at TaskRabbit in a moment. But what I was particularly interested was your time at Google, where, among other things, you were mentored by [now Facebook chief operating officer] Sheryl Sandberg. It sounds like a very close and useful mentorship. Tell me about that. How did you come to be in a position where you were in contact with Sheryl Sandberg and taking advice from her?

I joined Google when it was about 1,000 people. It was shortly after Sheryl had joined from the federal government. So she, you know, was new to tech, as much as I was new to tech, and I just graduated from grad school. And I interviewed with 13 people on the day of my interview at Google. And she was my last interview. It was a walking interview. And it was 12 to 15 minutes. She was walking into an interview with the CEO at the time, Eric Schmidt. And she just asked me a bunch of questions about what motivated me, what excited me, why did I want the job and that was it. I wasn't sure if I got the job or not.

So you did that walking along? The time she could give was going from one place to another?

That's all she had. And so she obviously has a reputation of being capable of doing so much, and accomplishing so much. And there's no surprise that she was able to walk to her interview, be prepared for that, interview me and decide - because that night, it was decided that they would hire me to do the job. She's an amazing leader, and an amazing person. So I worked with her group in a finance role for a number of years before I moved over into her team into operations. And what really began as a, you know, work relationship spawned into a friendship that included mentorship. And she just saw potential in me that I didn't see in myself, and all of us have somebody in our lives who see us and see the potential for us to lead. She saw the potential for me to lead bigger teams, to really expand my thinking beyond finance and apply my analytical strengths to an operations role in a more strategic role. And so she brought me into a role into her team. And ever since has been the one who sort of pushed me to think bigger about what I can accomplish in my career. But also keep me honest about my own authenticity as a person.

Do you speak to her now? Do you still check in from time to time and update each other on what's going on?

We do as much as we can.

Do you still draw advice from her?

I do. I remember when I was promoted to CEO of TaskRabbit, and I sent an email to some friends saying: "Hey, I got promoted." She wrote back to me and said: "All you have to do is do a good job." That was her feedback. She said it doesn't matter what people say about you, just put your head down and do a good job and crush it.

One of the things she encouraged you to do, I was reading, was form the Black Googler Network at Google.

Yes.

Tell me how that idea came about and how you became the person to run that.

It was a very selfish effort to create the Black Googler Network. I was sitting in the company, I'd been there for a couple of years. And there just weren't a lot of people who looked like me. And so I just wanted to hire more people. I knew that we existed, the talent was there. But there was something about the company that wasn't.... it wasn't happening, they weren't naturally applying for the jobs or naturally getting them.

What do you think was behind that?

When you're fast-growing company, you're just trying to bring people in as fast as you can. And we've all experienced those phases of growth, that you often forget to pause and look around to check: "How are we doing on inclusion? How are we doing on diversity?"

And so Sheryl had been a really big, important person who led a lot of women at Google. And so I went to her and I said I want to create this Black Googler Network. And she said: "You're it. You're the person that you've been waiting for to do this."

I then went out and made it happen, we got budget, we started recruiting from historically black colleges and universities. We created an internship programme that encouraged all applicants to apply and was one of the most diverse internship programmes in tech at the time. And created a way for the community to come together, which is what I really wanted, we started to have events, we started to talk about our culture more broadly. And we started to build connections, which I think helped a lot of us stay at Google longer than we might that we might have otherwise.

Aside from employee retention, what else do you think that brings to Google as a company?

Perspective. Thinking about the "other" and the perspective of the "other", really forces you to step out of everything that you do every day. And so I believe the company builds better products, because we have more diversity in the team. I believe that how you approach decision making. It might not be the fastest way to get to that decision, but it's the best way to get to that decision because you have all voices heard.

One of the things you've described in the past is how your hair was such an important part of changing how you felt to be at Google. Explain that journey to me.

We all have unconscious bias. Everybody, whether you're in a majority group, or in a minority group, and how you wear your hair is one of them. You may unconsciously think that just because someone wears their hair curly, they're not as serious. We were taught that if your hair was straight, you conformed to a certain norm. And you did it, because there were already so many other things about me that were different. I wasn't an engineer, I was a woman. I was African-American. So as a minority, you try to like simplify all of the differences in order to minimise the unconscious bias. And so that's how the hair came into it.

So you had your hair straight...

I had my hair straight. And then I decided to not wear straight anymore. So I had to cut it all off and do something called "twists" that eventually grew out, and now I wear locks. And I was very nervous about how people were going went to receive me. Were they going to treat me differently, because I was wearing my hair different? What questions were they going to have about it? And I got to work the next day and everyone's like: "Hi Stacy. How are you?" So a lot of it was me. And a lot of it was, you know, an assumption that you make about a person or what someone else might think. And now I fully embrace who I am. What you see is what you get. And I love that. I feel like I have more energy because of that. But it hasn't always been true, especially early in my career.

One of the things that Google is going through right now, it's this internal activism about various issues. Do you look back at the company and think it's moved on from the time that you were there? Or do you sort of see different kind of challenges that they're going through right now?

Well, the challenges at 1,000 are different than 70,000. I think that might be how many people they have now. The importance of hearing all voices is still the same. And the rise in activism has always been a part of the culture at Google. They had a company meeting every Friday before the company went public, and we would share everything. And then we went public and they stopped sharing everything. But it created an openness, a transparency and expectation and people will get up there and ask any question that they wanted. So it's not surprising to me that the nature of the questions, the level of the questions are absolutely still there. And they've escalated because the seriousness of the issues, if you look at what's going on in our society, have escalated. I think it's admirable that they have created the space for people to share their voice, and are doing their best, I believe, to encourage all of the voices to be heard.

Why do you think it's spilled out into the public?

The size of Google is such it impacts everything that we do every day. So the responsibilities are greater for what the company is expected to achieve. And we, as citizens who use this service, and depend on this service, have an expectation of leadership, an expectation of responsibility. And I think employees who work there carry that with them. And I think that's why.

So you left Google, you left a very good position at Google. What was the point you decided "I've got move on"?

It is hard to leave. There's free food every day. All the companies do that now. It was fun. And I worked with amazing people, Sheryl included, but so many amazing people. I had great responsibilities, I had a corner office with floor-to-ceiling windows on two walls. My dog came to work with me every day and I had a great assistant. There was nothing imperfect about that. But I was feeling called to do something different. And it was really a desire to build something, to create something new. And all of us who started something or joined something very early on, get this itch to do that. And so it wasn't about leaving Google. It was about going to something else. And I had fulfilled so many dreams at Google, so many. I lived in India, I worked in finance, I'd worked in sales, I'd worked a lot of functions. I've done so many things. And now my next calling was just something different.

One of the things that's happened in your tenure is the nature of TaskRabbit works changed quite fundamentally. Describe that to people who aren't familiar with both of those models. Describe what it was and then and then what it became.

The original version of TaskRabbit was like an auction, where you would go in and say: "I need my house cleaned tomorrow. And a lot of people would come in and bid on that cleaning. Or someone would go in and say: "I want this TV mounted on the wall next week." And people will come in and bid. And you as the person who posted it could pick the highest bidder, the lowest bidder, you could decide who you wanted. And so the auction was great, because you could see the best price, but they may not be available on the [right] day, they may not be available tomorrow, or next week. Or the person with the best price may not have all of the skills that you want. And Taskers were frustrated because they weren't finding the work that they wanted. They had to keep checking back often, to see if there was work for them.

Which meant we had about a 50% chance that you get your job done on TaskRabbit, like a coin toss. The people who were happy, were super-happy. And the people who were mad were angry. So we changed the model. And we actually piloted it in London. And we wanted to go somewhere different where people didn't know yet about the current model, and just tested in one of our most requested markets, which was London at the time.

So you had no business in London, at that point, so you launched it with the new method in London.

We called it a direct-hire model. The Taskers went in, they set their own hourly rates. We set a floor, which is the highest minimum wage in the country, so that they couldn't under-price themselves. And they set their own hourly rates, they set their hours, their calendar, their availability. And then they got to select what categories they wanted to provide services around and tell us about their skills. So when you show up as a client, you only see people who are available at the time that you want, with the skills, and you know exactly how much it's going to cost. And that increased our fulfilment rate, which is a metric that we use to really indicate the success of the model, to more than 90%.

Wow. So from the 50% before, to 90. After that successful pilot, you then have to change the system for everyone. And that was a particularly difficult moment, your Taskers in the US weren't happy about that.

We were excited to just roll out this model everywhere. And we knew that those metrics were possible, because we saw them in another city in another country. When we brought it back to the US, it was a change. And we had built a community of Taskers who depended on TaskRabbit for their income, they depended on us to pay major bills every month. And to not know if the big change that we were making was actually going to give them the $300 or $500 that they needed this month was scary. So they were mad, because we didn't tell them as much about it as we probably should have. But more importantly, they wanted to stay a part of the community that was going to provide a meaningful income. And the only way that we could show them that that was what was going to happen is to make the product change. They didn't care if it worked in London, they didn't live in London, they'd never been in London, they didn't care where that was. They just wanted to know if it would work in Chicago, in Boston, in LA, in San Francisco, in DC, where they lived right now.

It was a rough period navigating through that because we underestimated how powerful the community was, and their voice was. We now have a Tasker advisory council. There's Taskers here all the time at our corporate headquarters talking about their experience. We know exactly what's going on in the community.

You mentioned the sale to Ikea, which seems an obvious partner given given that many of your Taskers build furniture. But why a sale as opposed to doing what some of the other gig economy companies are doing and having a big splashy IPO that makes everyone billionaires? Why did a sale to Ikea make sense?

It came down to values. I became the CEO in April of 2016. And then we sold the company a year-and-a-half later. And that was not my intent. My vision was to bring TaskRabbit everywhere. At that point, we were just in the US and the UK. We had launched some more cities, but there was so much more we were doing to increase our engagement and usage and just spread this business around the world. We had a meeting with the Ikea team. They visited several Silicon Valley companies. And the meeting really highlighted for me, wow, this is an amazing company. They have great values. Ikea's mission is to create a better everyday life for the many people. Ours is to make everyday life easier for everyday people. Their's was written 75 years ago. Ours 10 years ago. It's just - there was so much alignment there. We were also meeting a huge pain point - the number of furniture assemblies we were doing from Ikea was astounding to them. Not astounding to us, but astounding to them.

You said recently that you feel like the gig economy is the future of work. That feels slightly terrifying to me, that small jobs, done on a very much ad hoc basis, might be the future of how people all make their living. What do you what do you mean, when you say the gig economy is going to be the future of work?

It's flexibility, which is the future of work. And it's not just because it's a gig and it's a short gig, you obviously can have flexibility and work at the same company every day for, you know, for 10 years. But really, when I when I put myself in the shoes of our Taskers, it really is the flexibility that is the future of work. There's a Tasker who I see, I've seen her a couple of times here, who has a college degree, had a great job. But because of life and things happening, she needed flexibility - pick her kid up from school, drop them off - to be available in the middle of the day. That was not an option for her at her other job.

But is the gig economy the solution to that?

It is a solution. It is what is working for her. I'm really challenging her advice to me right now, which was: "There are going to be days when you wake up, and people say what you're doing is actually not good for us. And I want you to know that it's good for me."

And so it's what works for her. And so who are we, the collective we, to say this is not the right future of work or not the way the future should go. This is a way. There are plenty of other ways. And I invite a dialogue on what those other ways may be, that helps people earn a meaningful income, that gives them the flexibility, that provides the security that they need to feel confident that they could grow their professional lives and build a family at the same time. What are those other ideas? Let's talk about them.

One idea particularly here in California is this distinction between contractors and employees. I wonder what impact it would have on TaskRabbit if, legally, you had to start making people employees instead of contractors. Could the company even handle that?

This is very new. We believe we can build a sustainable business, because we have a community of people who are totally dependent on what we're doing. So I like to believe that we can find a way that meets whatever regulations have been imposed on us, and then still allows for our platform to exist. So that if you want to work as an independent contractor or want to work in a flexible way, you can do that.

How many Taskers do you have?

We've got over 60,000 Taskers in our community.

So if they suddenly had to be employees, you'd have to pay for healthcare, holiday pay, and all those other things that get wrapped up when someone becomes an employee. Will the company be able operate that way? Because that's such a big expense that you just don't have now.

It sounds so daunting. But we're not sitting here saying, well, we should just give up. Right? What we're saying is like, wow, that's potentially daunting. Let's think about how we can make that happen. Because we've got 60,000 registered people who need to make it work.

So it wouldn't be it wouldn't be the end of the world, is what you're saying?

It can't be the end of the world. There are plenty of things that can end the world. A law in the state of California cannot be it.

We look at companies like Uber, when they IPO and they have to lay out their financials. It just looks incredibly unlikely they can turn those numbers around. And if this employee stipulation is added on top, the gig economy can only really exist because you don't have to have workers as employees.

I don't know enough about Uber's strategy to know how their [profit and loss] is structured and why it is that way. What I do know is we are focused on building a sustainable business. We're owned by a privately-held company that has been around for 75 years as a privately-held company and has sustained their growth because they've been able to achieve profitable growth. So I believe we've got the best minds thinking about this.

What are those minds doing next? What's what was coming down the line for TaskRabbit?

My vision is to bring TaskRabbit everywhere. We've been lucky to announce to launch Canada last year, France this year, and there'll be more geographic expansion to come.

Finally, I'm curious to know... there must be some very strange tasks that people have requested over the years. What are some of the things that stick out for you?

There's been some fun things like testers impersonating best friends for birthday parties.

I heard this! This is someone that pretended to be someone's friend because the friend couldn't make it.

The friend couldn't make it to the party. So she hired a Tasker to impersonate her. And the Tasker shows up, looks nothing like the friend, but has all of the facts from childhood and you know, everything and just... is the friend at the party. It was in LA, of course... obviously. The best friend figured out: "Oh, you sent.... this is my gift, which is like you, but not you!"

_____

Follow Dave Lee on Twitter @DaveLeeBBC

Do you have more information about this or any other technology story? You can reach Dave directly and securely through encrypted messaging app Signal on: [phone]