Leah Solivan, TaskRabbit founder: How the gig economy falls short

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0:30We do the things we do. And how to make better choices to help avoid costly mistakes. Each episode covers the latest research in behavioral science and dives into themes like the power of self-control, shaping your mindset for success, navigating new beginnings, and why starting over can feel so hard. Listen to choiceology at schwab.com slash podcast or wherever you listen. If you are currently overpaying on software to run your business, remember this number, 10 ,000. That's the number of new businesses that join Odoo per month. Join Odoo today at odoo.com. That's O-D-O-O dot com. Hello, I'm Sarah Rogers and this is the interview from the BBC World Service.

1:20The best conversations coming out of the BBC, people shaping our world from all over the world. I want to get freedom. I like that freedom. A gender equal world would be a better world for men too. We need assist fire. We need healing. We need trust. These companies don't really, they don't care what governments do. This is a war. The first thing that we want is a war to end. for this episode i speak to leah sullivan founder and former chief executive of task rabbit a platform that helped pioneer the gig economy founded in 2008 task rabbit is an app that connects people who need everyday jobs done with workers they can pay to carry them out from assembling furniture to making household repairs the model gave those workers greater control over when and how they worked, but did not offer the benefits associated with traditional employment.

2:21Leah says that the gaps in the model she helped create came to weigh on her. People just wanted to own the way they worked. But with that comes these institutional structures that have been built around work, the history of work, that doesn't allow for, let's say, benefits programs or paid time off or insurance, right? And so there were all these things I knew that weighed on me, that weighed on us. It wasn't a perfect system. It's not a perfect model. It continues to evolve and change. And frankly, I think the gig economy at this point has been around long enough. I'm surprised some of those systems, you know, some of these government systems and the way they're set up haven't been able to follow the trends of how work has evolved and what, you know, people want and how they want to work.

3:22Welcome to the interview from the BBC World Service with Leah Sullivan. Well, it was February of 2008. I remember it was February because I was living in Boston. at the time. And it was the dead of winter. It was cold. It was snowing outside. There was a big snowstorm. And I was going to meet friends across town for dinner when I realized I was out of dog food. And at the time, I had this 110-pound yellow lab named Kobe, who I kept very well fed. And he kind of looked at me with his little puppy eyes and he says, we're out of dog food. What are you going to do? And so I thought like, oh my gosh, this is such a simple problem.

4:08Why isn't there a simple solution? And really the key moment for me that the moment that lightning struck was when I grabbed my iPhone because the iPhone had just come out a few months earlier. This was brand new technology that people were just starting to build on top of. So I grabbed my iPhone and I thought, you know what? We should be able to connect with someone at the store at this very moment through this device. I bet there's someone at the grocery store in the dog food aisle right now, and I'm willing to pay them for their time. And that was the moment where it all clicked, where I had the idea.

4:47I felt like errands were too limiting. And I realized after 20 minutes or so that this was a bigger idea that goes well beyond dog food and was really an opportunity to connect humans across the country, across the world in new ways that had never been done before. So, I mean, it's massive now. It's in eight countries, something like 75 cities. But I want to know, what was the first version of it? What did that look like? Well, it looked a lot different than it does today. And the best-in-class last user experience at the time was eBay. And if anyone remembers going on the eBay and bidding, bidding on products and items, that was the first version of TaskRabbit where you would go onto the TaskRabbit site.

5:39You would say, hey, I need my dry cleaning picked up. That alert would go out to our tasker base willing to do the job. And those taskers then would bid on your job and you would choose who you wanted to work with. And how many taskers did you have at that point? Because it couldn't have been too many. Well, you know, I started the site with 30 taskers in one square mile of Boston, a little neighborhood called Charlestown. And I started it with the Charlestown Mothers Association because I figured moms were busy, even though I wasn't a mom at the time. But I matched those 30 taskers with those moms as the original version.

6:18So did you just put kind of an ad out then or something saying, I'm starting this business? How did you get Taskers on board? Who were they? So I put an ad on Craigslist saying that I wanted someone to run errands for me. And then I was infiltrated, just overwhelmed with applications from people because in 2008, this was now the fall of 2008, we were starting to go into the Great Recession. So the stock market was crashing, people were being laid off. I was completely flabbergasted by the quality of people that were coming to me and saying, I want to run your errands. But they were, you know, teachers, lawyers, you know, physical therapists that had just been laid off from work and were looking for new ways, more flexible ways of making money.

7:12And so I interviewed over coffee, 30 of them to start the site. I picked the 30 that I thought, you know, I could trust to go into maybe not even my home, but my grandmother's home and do a great job for people. And so that's how it started. What was then your, we have made it moment? Well, it's so funny because I don't know if I ever really felt that way. I always felt like we're chasing more and more and more. Even today, I'm like, oh my gosh, there's so much more TaskRabbit can be and do and build. But there was a moment early on where I knew, I didn't know if we were going to, you know, have huge revenues and huge scale and huge profits, but I knew we were going to be successful.

8:01And that was when we were just open in two markets. And there was a mom in San Francisco that posted a job in Boston. And she needed someone to go to the hospital because unfortunately her son, 20 years old, was going through a chemotherapy treatment at Mass General Hospital. So she posted on TaskRabbit, I can't be out there with my son, but I need someone to go to the hospital every day for a week, sit with him while he's doing these treatments, and then call me afterwards and tell me actually how it's going. And so the other tasker that picked up the job in Boston happened to be another mom.

8:42And the bond that these two moms formed across the country was absolutely incredible. And at that moment, we heard from both of them about how impactful and fulfilling it was to meet each other on TaskRabbit and to be able to help each other in this way that I knew what we had built. Again, just went far beyond small jobs, tasks and errands. We were really building something new and a new way for people to rely on each other. It's often said that TaskRabbit helped create the gig economy. So work is being paid per gig, which is great for people that want flexibility and, you know, people want a side hustle.

9:23But the flip side of that is job security, right? And no benefits. How do you reflect on being a pioneer of that? Yeah, it's a complicated thing because there are two sides of that coin. And, you know, when I was building TaskRabbit, of course, we were focused on building, scaling the business, helping to create the gig economy. As you said, this flexibility in the workforce. I remember doing these surveys of taskers and what they valued the most. Did they value the money? Did they value the flexibility? You know, was it something else? It was always flexibility. People just wanted to own the way they worked.

10:04But with that comes these institutional structures that have been built around work, the history of work that doesn't allow for, let's say, benefits programs or paid time off or insurance, right? And so there were all these things I knew that weighed on me, that weighed on us. It wasn't a perfect system. It's not a perfect model. It continues to evolve and change. And frankly, I think the gig economy at this point has been around long enough. I'm surprised some of those systems, you know, some of these government systems and the way they're set up haven't been able to follow the trends of how work has evolved and what, you know, people want and how they want to work.

10:53So it's an ongoing, I think, project and discussion and opportunity to continue to create better systems that support people in the way they want to work. And would you have done things differently or set up TaskRabbit differently, having that knowledge now? Because it seems really simple. I want this job done. Somebody saying, oh, I can do that job and money changes hands. That makes sense. But all the structures that you've just outlined around that, would you change how you set it up if you knew that that was going to be the direction that work was going to go in? I'm not sure there's much I could have done on my own.

11:32I think there's a lot of companies in the gig economy, including, you know, Uber and Lyft and Airbnb and others. And, you know, we did all kind of band together and, you know, go and lobby the government and talk through structures and programs that would be helpful. But I think it does take all of these businesses together to continue to push and offer, you know, solutions for change. A couple of things that we did that we could have done earlier and sooner were just find benefit partners, benefit programs to partner with for taskers and offer them discounts on health insurance, on different programs.

12:18And so we did that kind of at scale. And maybe those were things we could have thought of from the beginning. But in the end, I mean, it really, it's a massive economy, the gig economy. And it's going to take everyone, I think, to band together to help solve some of these issues. Want to know you're on the best path to the right car? At CarMax, the price you see is the price you pay. no negotiating no last minute surprises every car is carmax certified and backed by a 10-day money-back guarantee so you can buy with confidence want to shop from home go for it you can come in when you're ready take it for a spin and buy however works for you no pressure no haggling just the right car your way visit carmax.com for details want to drive carmax decisions made in Washington can affect your portfolio every day.

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13:40and what about the flip side for consumers you know they're welcoming you know people they don't know into their homes taking on jobs if you get a mark i'm assuming that things are great but people perhaps taking on jobs they're not quite qualified for where's the liability if things go wrong. Yeah, well, we had to put in insurance programs, insurance policies, and you're absolutely right. And, you know, obviously, when businesses are at scale, things go wrong all the time, every single day. You know, you try to build into the system measures to alleviate that. And, you know, some of it is at TaskRabbit, you know, I'm no longer involved today.

14:28So I can't say today how they're thinking about this. But I can say when I was running TaskRabbit, we were really focused on jobs that had less skills. So moving help, house cleaning, things that didn't require licenses or contracts. And so that was an area of focus for us because we did realize that, you know, some of these higher skilled, really professional jobs like plumbers, electricians, et cetera, like that's probably not the best place, you know, to find these people on TaskRabbit. We were, we were focused on a much different service offering. But in the end, you know, the, the liability did end with us.

15:13And so that's why we had to set up insurance programs and other safetiness so that consumers, so that clients could feel comfortable and confident using the service. Do you use it? Oh yes. I still use it to this day. I have my favorite taskers. Over the last couple of years, we moved. And so that was a big opportunity to utilize TaskRabbit. And I still, if I get new curtains or new something to hang on the wall, I'll call my favorite tasker and have him come over, Jonathan, and help me out.

15:52you're listening to the interview from the bbc world service with me sarah rogers when i spoke to leah back in july we were chatting over zoom she seemed really open for a former chief executive and founder she clearly reflected on the impact of her business on the world of work and didn't shy away from the hard stuff either she knew she was really successful and that does offer a lot to financial freedom, but can also come at a price. She now lives by what she told me she calls Jomo, the joy of missing out, turning down things in life and at work that doesn't do anything for her. And I think it takes a kind of strength to live that way and to know when something, including your own business, isn't working for you anymore.

16:41Okay, let's return to my conversation with Leah Sullivan. now you spoke a little bit earlier about the overwhelm of just doing everything you did go on to sell TaskRabbit but there was a big moment for you before that wasn't the life I'm sure to everyone else seemed to be going really well but the pressure of just scaling this business and making it a success it does take its toll doesn't it it does it does and you know that sort of last round of funding that got us to profitability, which then put us in a great position to be acquired by IKEA, you know, it did come at a cost and it was a huge burden.

17:28It was very stressful. You know, I ended up in the hospital with this stress-induced colitis. We didn't know what it was, but my colon almost burst due to the stress and pressure of this fundraise, I ended up closing the round from my hospital bed. And, you know, it actually ended up being an incredible investor that was a super fan of TaskRabbit based out of London that helped me close this deal. And so, you know, getting that international market open, our first international market was really important. Getting the profitability was really important. And then from there, you know, the IKEA partnership started and then that organically turned into an acquisition.

18:16What was the moment where you thought, I've got to make some changes? And did this, was the stress building up over time? Or was it just, you hear from people, they just have a moment where they think, I've just got to go to the hospital. Oh, you know, I think it had been building over time. I think it was almost a decade of stress that left me at that moment. We were, you know, two weeks away from not making payroll. And at that point, we had hundreds of employees and a full cap table of investors and, you know, live in 44 markets, 60 ,000 people relying on TaskRabbit to make money. It was a lot of stress.

18:57But, you know, so I think it built up over time and then it just kind of reached a breaking point at that moment. And so that was from your hospital bed that you decided you were going to sell TaskRabbit, I mean, an amazing opportunity to a huge brand, Ikea. Was that a relief at that point? Or knowing a little bit about you through this conversation and the drive that you've had, was it then hard to let it go? Well, it was all of those things and more. I think I felt everything at once and I knew it was time to let it go. I knew it was time to transition. I knew it was probably good for me and my physical and mental health to transition.

19:47And, but also I knew that Ikea was the right partner to continue to expand the footprint of TaskRabbit and the brand. And like you said today, live in eight cities, eight countries across the world. I mean, it's just been so fun for me as a founder to see TaskRabbit live far beyond me and, you know, continue to be successful without me being involved. And so at that moment, I felt all the things, but I knew it was time. And how do you take care of yourself now? Of course, you've got four children and you want to set an example for them, too, I imagine. Absolutely. Yes. I've gotten much better about, you know, making sure you carve out time for eating well and exercising and, you know, having a good routine around mental health, too.

20:37And so those are all important things that I've now been able to incorporate into my routine, into my day. But I also, you know, to be fair and honest, I have a lot more autonomy now than I felt like I did when I was running TaskRabbit. And I'm sure a lot of business owners, entrepreneurs and founders feel the weight and pressure coming from all directions and, you know, don't feel like they have much choice in how they handle that stress. Well, it's the dream for so many people, isn't it? It was for you. You come up with a great idea. You work for yourself. You make the money. You think that that's going to bring you this freedom.

21:15But actually, it can be a crushing weight as well. It can be all of those things. And, you know, in the end, as I look back, it was an absolute incredible journey that I'm so grateful for and feel so privileged to be able to have had. And I think it is the dream of so many. And really my dream from the beginning for TaskRabbit was to create something that lived beyond me. And so to have been able to do that and see it continue to grow now is such a delight. So would you say, given everything that you've gone through, was it worth it? Were you happy? Are you happy? Absolutely. Absolutely. No, I mean, to be able to, you know, be a part of creating the gig economy and shifting the future of work.

22:07I mean, these are sort of what I call precedent breaking ideas. And today as an investor, those are exactly the types of ideas that I'm looking to invest in as well and support this next generation of entrepreneurs and building their dreams and building their businesses. Yes, because you've switched to the other side of the table. You're not the one going out asking for money. You are being asked for money as a venture capitalist. Why did you decide to go into that? Why not? You've sold it to IKEA. You've got your work-life balance back. Just enjoy the good life. You know, I think I've always felt a deep, and I'm going to use this word very intentionally, obligation to not only recognize and be grateful for the success that I've had, but to bring others along with me.

22:59And so I really saw the opportunity to move over to the venture capital side, to become an investor, an investor who has a lot of empathy for founders, who has lived through a decade of founding, scaling and exiting a business, and then to be able to really help this next generation of founders do the same thing. And so I feel that deep obligation, not only as an entrepreneur, but as a female entrepreneur, as a Latina, my father's Puerto Rican, you know, the stats around how much money is raised by women and by Latina specifically, it's very, very small in the venture capital industry. And so I really see an opportunity to help shift and change those numbers.

23:45And, you know, back the next generation of great entrepreneurs that maybe even look a little bit different than kind of the traditional entrepreneur that you may think of. So you really want to pay it forward to those entrepreneurs that are out there with an idea and a dream. Give them the tips then. They're in the pitching room. What should they do? What gets their attention and what gets the money? Okay. So for me, the thing that gets my attention is I really want to understand your story. If you're pitching to me, tell me why, not just why you're creating this particular business, but why this business is connected to your life and to your story.

24:28Because as we just talked about, it can be really, really hard. It will be really hard scaling a company from nothing into a success. And you're going to have to break through walls to make it happen. And so I want to know that they're really deeply connected to the problem that they're solving.

24:50Thank you for listening to The Interview. If you enjoyed this conversation, you can find many more episodes of The Interview wherever you get your BBC podcasts, including ones with tech billionaire Reid Hoffman, director Chloe Zhao and Dr Ngozi Konjo-Iweala, head of the World Trade Organization.

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