Leah Solivan: Founder of TaskRabbit

Episode 644

On this episode of The Kara Goldin Show, we’re joined by Leah Solivan, Founder of TaskRabbit. Leah transformed the future of work with TaskRabbit, the revolutionary on-demand marketplace that paved the way for the gig economy. She shares her journey of scaling TaskRabbit to an international business, operating in 44 cities, and leading its successful acquisition by IKEA.
Now a General Partner at Fuel Capital, Leah supports world-changing ideas by investing in founders across industries like consumer tech and marketplaces. If you’re curious about innovation, building a disruptive business, or scaling for success, this episode is a must-listen. Tune in now on The Kara Goldin Show!

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Transcript

Kara Goldin 0:00
I am unwilling to give up that I will start over from scratch as many times as it takes to get where I want to be. I want to be you. Just want to make sure you will get knocked down. But just make sure you don’t get knocked out, knocked out. So your only choice should be go focus on what you can control. Control. Hi everyone, and welcome to the Kara Goldin show. Join me each week for inspiring conversations with some of the world’s greatest leaders. We’ll talk with founders, entrepreneurs, CEOs and really, some of the most interesting people of our time. Can’t wait to get started. Let’s go. Let’s go. Hi everyone, and welcome back to the Kara Goldin show. Super, super excited to have our next guest. We have Leah Solivan, who is the founder of TaskRabbit. And if you have not used TaskRabbit, you must, must, must. I absolutely love this company. In fact, my daughter, who’s now living in Brooklyn, needed to pick up some items in Providence, Rhode Island, and the first thing I thought of was TaskRabbit, go on there and see if you can make it happen. And she did. So. I thank you. Leah, you’re a true pioneer who’s transformed not only the future of tasks, but also the future of work with this creation back in 2008 and really laid the foundation, I believe, for the gig economy as we know it today. It’s in international also 44 cities overall, and successfully led the company to its acquisition by IKEA in 2017 now Leah is channeling her passion for innovation into supporting founders by a general partner role at fuel capital, so I’m super excited to talk about any And all of this. So welcome, Leah, how are you love it?

Leah Solivan 2:03
I’m well, Kara, thanks so much for having me. And cheers to you. I’ve got my favorite hint here.

Kara Goldin 2:08
Woo hoo. I love it right here with you so, so talk to us about what inspired you to create TaskRabbit, and maybe give kind of a definition of TaskRabbit for those who might not be familiar with it. Okay,

Leah Solivan 2:23
great. So it’s back in 2008 I was an engineer at IBM. I I love technology. I’m an engineer. I never went to business school. I know how to code. I know how to build things. And in 2008 the iPhone had just come out, and mobile technology was becoming, you know, really pervasive. Facebook was just breaking out of the college scene, becoming more mainstream. And then all of a sudden, because we were carrying around these mobile devices, we were able to use location awareness. And so as an engineer, I became obsessed with these three technologies, social, location and mobile. And I was out of dog food one night, and it was cold and it was snowing outside. I was living in Boston at the time, and this is like February of 2008 and I thought, There’s got to be a way to get this dog food. And the engineer in me, just on the spot came up with the concept for TaskRabbit, and I actually originally named the company run my aaron.com because of the very first thing I thought of and I bought the domain on the spot that night on GoDaddy. It was like 699 and, you know, pun intended, it snowballed from there, and so it started in Boston, and TaskRabbit is an app. You can find it on your mobile devices and on the web, and it allows you to connect with other people in your neighborhood and your vicinity to just help get small jobs and tasks done.

Kara Goldin 3:57
That’s amazing. So 2008 awesome year to be starting a company. Yeah, right

Leah Solivan 4:06
time to quit my job. Yeah,

Kara Goldin 4:09
exactly. And so what was the first thing that you did when you thought, Okay, I’ve got something here. What did you do next?

Leah Solivan 4:18
Well, I was still working at IBM at the time, but I started coding it up nights and weekends and talking to anyone who had listened to me. Literally, I’d ride the bus into the city of Boston, and I would chat with people on the bus. Hey, do you have someone that runs errands? How much would you pay to get your laundry picked up? You know, coffee shops. I met this whole moms group in this coffee shop in Charlestown. It was 900 moms in one square mile city of Boston, and I ended up actually building the first site for that moms group. It was a closed beta test, 900 moms, and I just listened to. What they needed, what their needs were. And I went out and I found taskers, task rabbits. I vetted them and interviewed them myself, met them all for coffee the first time, 30 minute coffee meetings. Picked the best, you know, 20 task rabbits I could find to start the service. And then, and then went from there,

Kara Goldin 5:19
when you were picking these task rabbits. I mean, what were these people doing beforehand that you were picking? How did you recruit them? Well,

Leah Solivan 5:27
Kara, it was, it was a crazy time, right? You mentioned 2008 so it was the great recession. You know, I quit my job in June of 2008 had the idea. In February, quit my job at IBM by June, built the first version of the site, got it launched with this moms group in the fall, like in September, right when the stock market was crashing and, you know, we were falling into a recession. And so it ended up being the perfect time to launch this type of business, because people were looking for work they were being laid off. I mean, these taskers were lawyers, they were teachers, they had professional careers and had just been laid off. I couldn’t believe it. And so I originally just posted an ad on Craigslist and started meeting people, and I was like, Oh my gosh. Like, this is so necessary. Like, the future of work is changing, and this platform is necessary. So

Kara Goldin 6:24
anything from picking up product in another city to building something, you know, what is the craziest task that someone has ever posted on the site that you that you’ve learned about.

Leah Solivan 6:42
Yeah, well, it’s kind of fascinating, because from day one, Ikea furniture assembly was always the number one job on task climate. So it was inevitable that someday, 10 years later, we were going to sell to IKEA. But along the way, there were definitely some really crazy, funny, strange tasks, including a woman in Chicago who dropped her keys in the lake and hired a TaskRabbit with scuba gear to dive down and find the keys in the lake for her. And he did. So there you go. I don’t know that

Kara Goldin 7:19
is that is hysterical. So, oh my gosh, that is so funny. So you were acquired by IKEA, as you mentioned, in 2017 How did you know it was the right move, outside of the fact that you had people signing on to build furniture? I mean, did you think about, should we grow more? I mean, what was kind of the point where you were like, Okay, should we really be doing this? Now, I

Leah Solivan 7:47
know. I mean, in Kara, it’s one of those decisions I continue to look back on as a founder, and I always feel like, Man, there was so much more to do. Like, did I leave something on the table? Like, I Yes, there was more to do. There was more to build. But I think that the compelling thing about IKEA, and what has played out is that they had this international, global footprint. And my aspiration was to build a global company and a global brand. They have kept the brand intact, which honestly, to this day, I walk into an IKEA store and I’ll see the task, grab it brand. I’d be like, oh, like, it just it just like, feels nice that they’ve kept it. And to see the ability to roll out in many other countries, you know, Spain and the UK and Germany. I mean, that is something that for us would have taken so much capital to raise, and IKEA was such a great strategic partner, and we had already proved that, you know, it was a complimentary business. And so in the end, it did make a lot of sense to go through with that acquisition. Did

Kara Goldin 8:56
you stay on for a period of time with the company? Or what exactly happened?

Leah Solivan 9:01
Okay, so our mutual friend who’s amazing, Stacy brown Philpott, at the time, I had promoted her to be CEO, and she was running the day to day for the last year before we were acquired. I was chair of the board. And so when the acquisition offer came in, and we as a board were assessing it. Part of the deal is that Stacy would stay on for three years at IKEA and help through the transition. But I as the chair of the board was done, like I just I was done, and so that was okay with me. I was, you know, good with that, and Stacy’s incredible, and she did stay on through the three years and transition everyone. And we now have another CEO, another female CEO. TaskRabbit has had three female CEOs in a row, and I asked Smith is the third, and she continues to run the business internally, and was hired by IKEA to do that.

Kara Goldin 9:57
And so have you stayed in. Involved. Obviously, you moved off of the board. But have you stayed involved to some extent?

Leah Solivan 10:04
You know, I don’t have any sort of financial tie to TaskRabbit any longer, but I, you know, am certainly, I know Anaya and we’re, we’re all in YPO together, actually, Stacy and myself as well. And, you know, actually, just recently, with the tragedies happening in LA with the wildfires, I contacted and I and I said, let’s get some task rabbits with vans, and let’s have them drive donations down. And we did. And so, you know, I had a, you know, donation hub at my house in the South Bay and had a Tasker, one of my favorite taskers, with a huge white van, who just took loads and loads of donations south to LA and so, I mean, it’s moments like that, actually, where I feel still really connected to what I built in the business, because I see how much of a difference it can make? Yeah,

Kara Goldin 11:03
definitely, yes. So you took some time off, a little bit of time off, and then you went into actually talk, talk about fuel capital a little bit. And how did that actually happen? What was the transition all about?

Leah Solivan 11:19
So when we sold TaskRabbit to IKEA, I was pregnant with my second child, and I have four children, but I was pregnant with my second and I took about a year in between, had the baby kind of regrouped, and through that sort of, quote, unquote maternity leave, I started talking to venture capital firms, and I got pulled in that direction by a lot of different people and friends over the years, who I had met, who I had pitched to, but I wasn’t sure if that’s what I wanted to do next, and so I spent about a year kind of exploring that. What would that be like? What’s the day to day like? Would I like it? Would I not like? Would I be good at it or not, I don’t know. And I ultimately decided I love helping entrepreneurs. I love enabling others. I mean, that’s part of the TaskRabbit mission as well enabling others to do their best work, right? And so it became very clear that this would be a natural transition for me to go into venture and help back amazing founders and teams and companies. And I have loved it. So I’ve been at fuel capital now since 2017 and we invest at the earliest stages, sort of pre seed and seed across all sectors of technology. So my passion is definitely in consumer and marketplaces, but we’ve invested in SaaS companies and infrastructure companies, etc, and it’s just the dream, and it’s just so interesting. And I’m sure, sure this may resonate with you too, from him, like, as a founder, you feel like what you’ve built is so tied to your identity, like it was very difficult for me to sell the company and be like, Okay, well, what, what do I do now? Like, it’s been 10 years of my life and like I am TaskRabbit, right? And so what I’ve realized now is, with some time and space, and, you know, a whole nother career, that TaskRabbit really enabled me to become the investor I am today, and that feels great, because I have the empathy, like I understand what these founders are going through. I feel like it’s really helped me identify strong teams and visions and product market fit in a way that I wouldn’t be able to if I hadn’t founded my and built my own company? Yeah, definitely,

Kara Goldin 13:41
when somebody comes in the door and and has founded a company. I mean, is there a formula for figuring out that this person can actually do it? I mean, I always say that, you know, the actual product or service is so key, but it’s also about the people, and can the people actually execute an idea as a dime a dozen? But what do you are there any tools you use to figure this out that you could share? I

Leah Solivan 14:13
mean, it’s a great question, and, you know, we invest at the earliest stages, so there’s not always a lot of data. Usually there isn’t. There’s no revenue. There’s, you know, not a lot of metrics to go off of. And so it is about what I call the founder market fit. Is this the team? Is this, the founder that is purpose built for this particular business, and why is that like when a founder walks in the room to tell me about their company, I first want to hear about them. What is their background, where did they grow up? How did that influence them? Like, why are they sitting in front of me today pitching this particular business? I think all of that really matters, because, as you know, it is not a straight line to success. There are. Lots of ups and downs, and, you know, the majority of startups fail because they hit roadblocks, they hit walls, and they don’t know how to go through them or around them or figure out different paths. And so you really have to, I like to bet on the founders that I feel like are really going to push through in those moments that seem impossible. So

Kara Goldin 15:25
it probably depends to some extent on what the company is. But team, of course, this is also so critical. Before you invest, what do you want to see in a company outside of the founder?

Leah Solivan 15:39
I really want to see a balanced team. And so, you know, the founder or co founders can come from, you know, different areas, different skill sets, but I want to see a well rounded team. I was a technologist. I was an engineer. I did not have a business background or a finance background or marketing background. I had to build that team around me, and so seeing a team walk through the door that has been curated, highly curated by the CEO, by the founder, and people that are better than you like being able to hire people that are better than you with no ego, with no sort of, like, oh, I want to be at the top. No, like, I want to see give me a great team with a solid founder, and then experts, you know, across other areas. I mean, I think that shows just alignment around success and building a great business.

Kara Goldin 16:40
So you’ve invested in just a couple of the companies, figma and Flexport. What excited you about both of those companies? You

Leah Solivan 16:49
know, those companies were in fund one, actually, those both were examples of my partner, Chris, who he invested in both figma and Flexport early I came in sort of after that, and a couple of companies that I invested in it, and I’m super excited about one is called Picasso, which is second home marketplace, so it makes sort of vacationing more accessible. You know, we have a share that we bought of a house in Fort Lauderdale, Florida, and so we’ll go there for all the kids, you know, school vacations and spring breaks, and we can leave stuff there, particularly with children. It’s been very, very helpful. Another company that I really, really love is a company called upwards. We were the first money into this company, and it’s a childcare marketplace, so it kind of hits all the notes around for me, consumer based marketplace focused on children, and this founder, Jessica, is just outstanding. And so there’s been a lot of companies across all kinds of different sectors. I’ll name one more that I’m just obsessed with right now, because I know you’re friends with him too, which is Eric Ryan at CAST cast jewelry. And he is just a mastermind, literally a mastermind. He did method soap, Oli vitamins, welly bandages, and now he has cast jewelry. And so we partnered up with Eric when he was raising his seed round, and it’s been really exciting to see the growth there too.

Kara Goldin 18:22
I’m excited about that company as well. So you’ve talked about the importance of embracing risk. Can you share a time when taking a risk really paid off in your career, whether that was while you were inside of TaskRabbit or another time.

Leah Solivan 18:43
I mean, there were, there were so many times that I, being an entrepreneur, is taking risks on a daily basis. I think one time that stands out, that was really scary and really painful was when we had $20 million in the bank, and I still decided to lay off 30% of the team. It was terrible. It was embarrassing. I felt like a failure, but the burn had gotten out of control. The company got too big, too fast, and I had to right size things. And it really came along with reshaping the product and being able to launch a strong mobile product, and not just web. And so I needed to bring down the burn and kind of reorganize the team and hire more mobile engineers and less web engineers. And it restructure everything. It was a terrible transition, and in the end, it is what paid off, got us to profitability, got us the partnership with IKEA, and ultimately, you know, got us the the acquisition outcome. But in that moment, I did not know if it was going to work. That’s,

Kara Goldin 19:56
I mean, it’s a brave thing to do that, right? I. I’ve I’ve experienced it ourself, and it’s definitely a super, super brave but scary thing. You’re hopeful, but you also have to play it out and learn from your own experiences. So TaskRabbit was a game changer in the gig economy. Did you know that you were creating an entirely new category when you were actually creating that company? No,

Leah Solivan 20:23
I did not, but not, not immediately, but because of the timing, because we were hitting the Great Recession, as I mentioned, and then coming out of that, it was clear that we had hit a wave, a transition that was happening, and we were a big part of forming the gig economy, along with Lyft and Uber and Airbnb and get around and Turo and all the others, right? I mean, it’s, it’s, it’s not an accident that all of these companies started in the sort of 2008 2009 time frame. It’s because the technology had shifted, the recession had hit, and everything was changing underneath us. And so that’s how the gig economy formed. And I didn’t see it immediately, but I’d say by 2010 2011 when people started really focusing in on, this is the sharing economy, this is the gig economy, I was like, Oh, wow, it is, and we’re a big part of that. Yeah. So

Kara Goldin 21:36
you talked about some of the companies that you’ve invested in that you’re most excited about, if you you get pitched on a number of deals. This is a crazy time for so many to be raising money as well. But you’ve done consumer tech to education marketplaces, lots of incredible companies, and seen a lot of different things. Is there a particular sector that you’re super excited about right now that you think has really played you know what people want to invest to that? I mean, AI probably is an obvious one. What else have you really seen has really taken off

Leah Solivan 22:20
well, I mean, here’s an a non obvious, sort of contrarian view, which is, right now most venture capitalists will not touch consumer deals, and that is the time to invest in consumer deals, right? I mean, it’s like, you know, the majority of venture capitalists, they’re kind of like herd animals, they kind of like follow each other in the back, right? And a lot of these firms are restructuring their getting rid of their consumer focused investors and investments, which is just such a bad call. I mean, these things go in cycles like now is the time to be digging deep in consumer, of course, AI, of course, AI is changing everything. It’s like the dawn of the internet. Like it is one of those, right, like, major technology shifts that will touch everything. But, you know, I’m, I’m frustrated with the majority of venture capitalists right now that are abandoning consumer but I’m also sort of excited and delighted to be able to fill that gap and really understand consumer trends and see that this is the opportunity where the big companies are going to be started and built And the highest returns are going to be made.

Kara Goldin 23:42
So what do you tell your founders? Obviously, you’re doing early stage, and then often, in order to grow, they need some additional capital. I mean, what do you tell them? What kind of advice?

Leah Solivan 23:55
Yeah, conserve cash. You cannot run this like you would in 2012 2013 you need to be super scrappy. You keep your burn down, you figure out ways to make money immediately. You have to play a different game today than you would have 10 years ago. You just do. And there are still great consumer investors at Series A, Series B, beyond but I mean, it is so much harder. Valuations are a lot lower, which I don’t think is a bad thing. When I raised money for TaskRabbit, my first round was done a million dollars on a $4 million post, okay, that was 2008 pricing. That was average, normal, right? Like so, things got way out of hand, and I think valuations now have sort of come down. They’re settling out. And I just think you have to be really disciplined and strategic about how you build your brand today.

Kara Goldin 24:57
When what advice do you give to. To founders or or potentially CEOs if they ask for your advice on when do you sell?

Leah Solivan 25:10
That is a tough question. It’s a really hard question. You know, I think you sell when you don’t need to for one. And for us, it was nice having a strategic partnership and a business development deal in place before we sold because we understood who we were selling to and what that was going to look like on the other side, there were no surprises to this day. I mean, years later, it’s very much what I imagined it would be. You know, sometimes I think there are, there are opportunistic sales that occur. And I would say you can’t, you can’t plan for those like, you just have to build your business heads down and do the best that you can do, create some partnerships, be talking to people, all of those things, but really focus on the building piece. Because in the end, that’s what’s gonna matter. I mean, you’re gonna be priced on a multiple of revenue. So like, get as much revenue as you can? Yeah,

Kara Goldin 26:22
definitely. And if you’re not growing, you know, you’ve got to really figure out why, yes, pretty quickly, definitely. So you are on a number of boards. You’ve been on boards, you are helping probably build boards as well. When you look at the best, most highly functioning boards, what would you say, I guess, to any founder who’s building a board, but also to people who are kind of in your position helping to build those boards? Yeah.

Leah Solivan 27:00
I mean, I’ve been on a number of private company boards. I joined a public board last summer as well. That I’m really enjoying a bunch of nonprofit boards as well. And I think the key theme, as I look across all of those is just a diversity in voice experience, skill set, and a deep, deep respect for the CEO and management team. You know, the healthiest boards really have strong CEOs that they trust. They’re not in the weeds. They’re not digging in. It’s really up to the CEO and the management team to be executing. And the board becomes sort of this, you know, advice, sounding board update, like, those are the best boards. You You really don’t want to be building a board or be on a board where you’re doing a lot of heavy lifting, because that is not the role of the board. And that can get really, really tricky. And I think sometimes for me, I find it to be a really great skill to have been an operator, to have been a CEO, and to now be serving on boards, because I kind of understand that dynamic. I understand the pressure the CEO feels in a board meeting, and I’m very sort of cognizant and empathetic to the CEO. But I think a lot of times, operators can just dive too deep into the weeds as well with questions or like, oh, you should do this or advice and expect it to be done. And so I think really understanding what the role of a board is is also important, definitely.

Kara Goldin 28:34
So one piece of advice you give to entrepreneurs who maybe have a great idea that they’re thinking about launching, and kind of knowing what you know today about launching, like I said before, not just a company, but entirely new category, which we did at hint as well. I absolutely did that. That is something that I think you don’t take lightly. And what would you say to that? Though?

Leah Solivan 29:09
Well, when I think about myself, I found a Task Rabbit when I was 28 and I had no idea what I was doing. And I think a lot of times people can overthink things. And I think the best advice I could give to my 28 year old self would be, don’t overthink it, just go for it. Like just try it. Iterate, gather data. Be fast, be agile, evolve, change, adapts like is. That is the nature of entrepreneurship, and it’s not perfect. It’s not perfection, and it never will be, and so just try, just take that first little step to get it out there and build from there.

Kara Goldin 29:55
Thank you so much. Leah, your journey from founding to. Running and supporting entrepreneurs now at fuel capital is nothing short of inspiring. As you also mentioned, we’re both part of YPO. I know you do so much there too. So thank you for doing everything that you’re doing and for sharing your story and your insights. Really super incredible for everyone listening, uh, definitely check out everything that Leah is doing. We’ll have all the info in the show notes as well. And as always, if you enjoyed this episode, don’t forget to share it, and we’ll see you next time. Thanks, Kara. Thanks again for listening to the Kara Goldin show. If you would please give us a review and feel free to share this podcast with others who would benefit. And of course, feel free to subscribe so you don’t miss a single episode of our podcast. Just a reminder that I can be found on all platforms. At Kara Goldin, I would love to hear from you too. So feel free to DM me, and if you want to hear more about my journey. I hope you will have a listen or pick up a copy of my Wall Street Journal, best selling book, undaunted, where I share more about my journey, including founding and building. Hint, we are here every Monday, Wednesday and Friday. Thanks for listening and goodbye for now. You.

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