The vital question Leah Solivan wished she asked investors

LEAH SOLIVAN: From day one, the highest volume task on the site was always IKEA furniture assembly from day one.

I mean, I was like going to IKEA, and getting these flat packs with my little Allen wrench, like putting IKEA furniture together. So it was always a popular task, okay?

And I would always, you know, give these talks and be like, “can anyone in the room guess the most popular task on Taskrabbit?” No one would ever guess it was always IKEA.

JEFF BERMAN: Taskrabbit can help you find someone handy to do all sorts of work: like assemble a bookshelf, pick up your dry cleaning, or help with the yard work.

And that’s Leah Solivan, who founded the company and, in the early days especially, often did the tasks herself. She grew the company to impressive scale, and then became laser-focused on a perhaps non-obvious partner: IKEA.

SOLIVAN: They were on our dream list for a long time. We want to be in-store. We want to be part of their checkout process, you know. But they were really very elusive. Very difficult to get to. Private company, family owned, out of Sweden. And at that point, we were live in London, internationally. London was our fourth largest market. It happened to be IKEA’s first largest market in the world. 

BERMAN: Leah convinced IKEA to pilot a partnership with Taskrabbit in London.

SOLIVAN: You’d buy IKEA furniture on checkout. You could sign up to have Taskrabbit deliver it and assemble it. Drove up the average order value immediately for IKEA. They were psyched. And we were excited we had all these new customers. I mean, it was a win-win. It was so obvious. We were not thinking acquisition. But, IKEA started thinking acquisition. 

BERMAN: That led Leah to successfully exit her Boston-founded tech start-up … to a Swedish furniture giant. 

Taskrabbit’s scale story is about meeting customers’ timely needs – and Leah’s ability to leverage transformative technology.

I’m Jeff Berman, your host.

Leah Solivan founded Taskrabbit in 2008 and helped lead the company as it expanded to more than 40 cities. We’ll hear more about that impressive scale story later. First, I wanted to hear about her second act. She’s now a general partner of an early stage fund called Fuel Capital. 

BERMAN: Leah, welcome to Masters of Scale.

SOLIVAN: Thank you so much for having me. 

Copy LinkWhy Leah Solivan became a VC

BERMAN: I’m thrilled that you’re here. Before we get to how you built a company and sold it to IKEA, you’ve been doing Fuel Capital now for how long?

SOLIVAN: Almost 8 years. Yeah. Almost eight years now.

BERMAN: And what made you decide to stop being an operator and start being a VC?

SOLIVAN: It was a big decision to go over to the dark side, as some would say. I really started Taskrabbit out of a place of being a technologist. My background’s engineering, I love technology, and I sort of accidentally started this company. And it took up 10 years of my life and had a great outcome, and it was an incredible journey, and that was all good. But at the end of it, I had felt like I had missed out on other emerging technologies that, you know, were forming and I was excited to kind of be able to dig in and learn and I wanted to do something next that stayed within the realm of entrepreneurship, but allowed me to kind of continue to expand my learning and work with more founders.

BERMAN: And so I’m curious when you’re either vetting entrepreneurs or you’re coaching your portfolio leaders, what are you drawing on from your own experience that is surprising to you? What do you find yourself going to with them?

SOLIVAN: I mean, a lot of PTSD.

BERMAN: Yeah. 

SOLIVAN: I mean, honestly, it’s just, I have so much empathy for the journey and the process, and I had a very complicated board dynamic at different points in my Taskrabbit journey, and I was always super sensitive to the imposition that investor can have on a founder, and I always wanted to be that investor that was going to be really helpful and was kind of the back channel call or the back channel reference, and I’ve been very careful to not be an imposition.

So I think it’s really about having sort of that personality, that low ego, that sense of humbleness that you can bring to a board meeting that allows you to ask good strategic questions and not just asking questions for the sake, you know, of asking, but to really understand deeply the business and how you can be helpful.

Copy LinkHow AI is changing how Leah Solivan invests

BERMAN: As we sit here, if my math is right. We’re about 16 years after you found a Taskrabbit.

SOLIVAN: Sounds crazy to me! 

BERMAN: What is different that is not obvious about starting a company today than when you started Taskrabbit?

SOLIVAN: I think a lot of things are very different. I mean, let’s start with the technology stack first. I left my job as an engineer at IBM where I was programming in C and Java. We were burning CDs, and we were shipping them around the world. 

BERMAN: For some of our audience, we’re gonna even have to explain what that is, but yeah, go ahead. 

SOLIVAN: Okay. Yeah. Now, I’m working with a couple start-ups, in advising, that are building AI products. Okay. This is a different game. We’re talking GPUs, we’re talking very expensive, we’re talking one server, one GPU can run one thing at a time. And I’m like, how do you launch this to the masses? I don’t understand. And so I think that technologies like AI, it’s a big game-changing technology, but the costs are still so high to launch something. I think start-ups, you know, need to raise a lot more money to get started right now, today, than I did. I mean, I started with 250K from angel investors, right and got me pretty far.

BERMAN: And the cost of, especially, an AI-driven start-up right now, is that making you hesitate more about making investments. Is that changing how you invest?

SOLIVAN: It absolutely is changing where I think it makes sense for early stage, small funds to invest. I mean, it’s almost like when we used to look at hardware companies, and we’re like, whoa, this is going to take way too much capital, like the ROI on our investment, the math just doesn’t work for our fund. I mean, I think to some extent, to some of the big AI companies, you see the same thing. And so you see the big players like Andreessen or you see Microsoft investing in OpenAI. You need really, really deep pockets to be successful. I think it’s harder for the small funds to play here.

Copy LinkThe origins of Taskrabbit

BERMAN: Yeah. Okay. I’m going to take you back to winter, 2008, it’s a snowy night in Boston.

SOLIVAN: It was a dark, snowy night.

BERMAN: I mean, it was literally right?

SOLIVAN: It was a big snowstorm.

BERMAN: And so what, what happened that night that gave birth to what became Taskrabbit?

SOLIVAN: So, I was getting ready to go out to dinner. I had called a taxi to come pick me up. We were meeting friends, and we realized we were out of dog food. And we had this hundred pound yellow lab named Kobe at the time. Amazing, amazing dog. And I thought, you know what? How are we going to get this dog food? This is such a stupid problem. 

We’re going to be late for a reservation? Are we really going to stop on the way home while the stores will be closed? The iPhone had just come out four months earlier. And I grabbed my iPhone. And I thought, why can’t I use this device? To connect with someone right now in real time and get the dog food, you know. At that time, no one was using location based awareness in their tech stacks to pinpoint where people were, right, because the iPhone had just come out, Facebook was just sort of breaking out of the college scene, becoming more mainstream, but no one was really leveraging the social graph to build trust between users.

But for me as an engineer, I saw these three technologies, social, location, and mobile, and I thought, there’s a lot here. There’s a lot that we can do. And so that was really where the idea for Taskrabbit was born. I used my iPhone at that moment, and I thought, okay, if such a site existed, what would it be called?

And I typed in the domain name, RunMyErrand.com, and it was available on GoDaddy for $6.99, so I bought it. And then for the first 18 months that we existed, we ran under that name.

BERMAN: But at the time you had this idea and the URL’s available and you’re putting these new things together, you’ve got a pretty good job at IBM.

SOLIVAN: I have a great job at IBM.

Copy LinkLeaving IBM to start Taskrabbit

BERMAN: So, did you decide to jump right away or did you take your time? How did you play it?

SOLIVAN: It took me a little while, and really thinking back to that time, you know, I realized a couple things. One, I started out as a quality engineer at IBM, not as a programmer. And I had a background in computer science, but I got my first job as a QA engineer. And so I was looking, you know, for bugs in the code, and I’d find them, and then I’d pass it to the engineers to fix. It took me a really long time for them to move me into an engineering role. I had to really fight for it. I actually had to get a job somewhere else. And come to them with an offer and say, this person’s willing to hire me as an engineer.

BERMAN: Do you think that was misogyny? Do you think that was…what do you think it was?

SOLIVAN: At that time, honestly, probably a little bit. And I was also pretty young. I was in my early 20s at the time. I was young, female, I saw young men come out of college and get the engineering job, and that always bothered me. but it was also a track at IBM in a big company where you had to pick if you wanted to be a technical track or a managerial track. I loved being on the technical side. I think they thought I’d be better on the managerial side. Again, I’m not sure if it was because I was a young woman. I mean, honestly, you can ask anyone about my people management skills. Like, I think my technical skills are better. 

BERMAN: I’m guessing you’re pretty good at both. 

SOLIVAN: Yeah, I mean, but you know. So, I was a little bit frustrated to be honest there. I had spent eight years there. 

BERMAN: And did you have a mindset of like, hey, 30 years and the gold watch is still a career choice?

SOLIVAN: That is the model I had seen in my life. My father spent 30 years in the Air Force. No one in my family was an entrepreneur. No one had started their own business or company or even worked for a small company. My parents were extremely proud of me getting the job at IBM.

But there was always this nagging, you can do more, you can do more, you can do more. And so I think I started to kind of follow that curiosity. And when I saw these new technologies develop and emerge, I just started playing around with them, nights and weekends.

And I think that’s what sort of started to pull me away and drive me towards, if you have a great idea, maybe you could actually go build it. You could go start it. But it was a big decision. And it wasn’t an easy decision to leave. I ended up cashing out to start the company with my pension from IBM.

BERMAN: That’s a big decision. How did you get to the point of saying, “I’m maybe not going to burn the boat, but like, I’m going to go and do this and give up a very safe, very secure, prestigious career track?”

SOLIVAN: I’m not sure exactly what gave me the confidence to do it in that moment, but I remember being eight years old and asking my father what the highest position in a company was. And he told me it was being a CEO.

And I remember asking him that question when I was eight. And then creating my first start-up, which was this recycling program in my elementary school. I liked being the boss. And I think, so I had the personality that was like, I have the ideas. I like being the boss. I like organizing things and people.

I think as I built up the skill sets, I sort of realized, you know what? Maybe I could do this. I think a key person though, a key mentor, that really got me over that hump. was Scott Griffith, who at the time was the CEO of Zipcar.

BERMAN: How’d you get to him?

SOLIVAN: It was complete serendipity. I was out to dinner one night with friends, telling them about the idea. And this one woman said, “Oh, you know who would love this? My friend Scott. You should email him. Here’s his email, ‘scott at zipcar. com.’” You know, just go shoot him an email. This was on a Saturday night. I was like, OK. I didn’t know he was the CEO.

And so I emailed him, cold email. I said, “Oh, your friend said I should email you about this idea.” He writes back Sunday morning. And he’s like, “Why don’t you come by my office this week?” And I see that he’s the CEO of Zipcar and I’m like, “Okay, I should prepare for this meeting.” You know? And so I got lucky. And then Scott and I just really hit it off.

Copy LinkAdvice for leaving your career to become an entrepreneur

BERMAN: I’m curious because so many of the entrepreneurs who we talk with on Masters of Scale have a similar story where they were at a company they had a job, and they didn’t leave right away. They spent some time working on nights, weekends, whatever when entrepreneurs are coming to you, and they’re in that position. They work at Meta or Microsoft or whatever it is, but they have this thing. What advice do you give them about when to make the jump and actually go do it full time?

SOLIVAN: It’s really hard to be all in on something if you have a day job. So I do believe that you have to give it your all. You have to dedicate your all, one way or another. I’m also very sensitive that not everyone has the access, the opportunity, the privilege. Just to be able to do that without a safety net, so I’m very sensitive to that fact as well, you know, but I sort of look back on my journey, and it was like the 27,000 pension plan. You know like any little thing it was, you know, the credit cards that you know took me time to pay off whatever it was. And so my advice is if you really have conviction around something, you are going to find a way. You’re going to find a way to go for it. And so many start-ups fail too, right? Like so many ideas are just not good, or the timing isn’t right, or the market’s not right. And so I’m always digging in with entrepreneurs too that aren’t sure, like, is this the idea? Is this the thing? Yeah. Because it’s a lot. It’s a lot to sacrifice if it’s not the thing. If it is the thing, it’s a lot to

BERMAN: Yeah, and you have to sign up, be ready for it to be a ten-year plus journey. And to your point, it’s seven people in a room, and if the trash needs taken out?

Copy LinkEarly days of developing Taskrabbit

SOLIVAN: You’re taking it out. Absolutely. And I, you know, leave my job at IBM, I wake up the next morning, and I just start coding. Like I roll out of bed.

BERMAN: You are a one woman band.

SOLIVAN: And I just code for like, I don’t know, six weeks straight. And it’s all in my head, and I gotta get it out of my head. And so I got a first version built and sort of what was very helpful in that time was, I spent a lot of time locked away in a room coding, but I also spent a good portion of time at a little coffee shop surrounded by people. And I would pull people over. I’d grab them and be like, “Hey, let me tell you about this product.” I’m like, “Would you use this?” And like, “How does this interaction feel to you?” I mean, I would get people in real time. And, you know, the little coffee house Zumi’s coffee shop in Charlestown was super nice to me and let me hang out there and talk to their customers all the time.

BERMAN: Free Wifi, free refills. You’re good to go. 

SOLIVAN: Yeah, it was a lot. And it took six to eight weeks to get something built that I felt like was ready for people to use. 

And then I said, okay, I need to find people that are going to do the jobs. And so I went on Craigslist. Put out an ad for someone to run errands. And I was completely overwhelmed by the number of people. Oh my gosh. I mean, it was September of 2008.

The stock market had crashed. Everyone was being laid off, I had lawyers coming to me, teachers looking for work. I mean, talk about timing. And I didn’t plan the timing like that, but it turned out to be the perfect time to launch a company like Taskrabbit. And so the supply side, the taskers or the people running errands, it was overwhelming. And so I hand interviewed every single person, because I was very worried from the beginning around trust and safety, and again, this was long before you jump into a stranger’s car. Feel okay about that. I started with 30 taskers that I handpicked.

BERMAN: That’s a big number.

SOLIVAN: It was a lot. But I felt like for what I wanted to do for the launch, I found this mother’s group in Boston. It was 900 moms in one square mile, but they were very concerned about trust and safety, right? And so I was like, OK, if I launch a closed beta just for them, I just built it for them, and I found 30 taskers that I hand-selected.

BERMAN: Wow.

SOLIVAN: And then that’s how it started.

BERMAN: Still ahead, how Leah scaled Taskrabbit from a single neighborhood in Boston to a global business.

[AD BREAK]

BERMAN: Welcome back to Masters of Scale. You can find this episode and more on the Masters of Scale YouTube channel.

Copy LinkLearnings from the beta version of Taskrabbit

And so, you do this closed beta. 30 taskers, 900 moms. What do you learn from that?

SOLIVAN: One of the main learnings was, I needed to be the first tasker, the taskrabbit as well. And so I had this little Vespa scooter I rode all over Boston running people’s errands.

And that was the best learnings that I could get about building this company. And that’s another thing I’ll tell founders when they’re building their business. Can you be a part of the process? That is how you learn about what customers want. Because taskers are customers too.

And so I needed to understand how they were getting jobs, finding jobs, how much money they were making. Did that make sense for them economically? What types of jobs, what types of skills did I need to recruit? I mean, it was so much learning. I learned very quickly that by offering a service where you could get anything done, one, people had no idea what to post.

BERMAN: Right. It’s unconstrained. You actually needed constraints.

SOLIVAN: Exactly, it was like blank space, no one knew what to use the service for, and then two, on the tasker side, I needed people that could do a lot of different things that weren’t just specialized in one or two things.

BERMAN: Cause picking up dog food is one thing but fixing a leaky pipe is another?

SOLIVAN: Exactly, yeah.

Copy LinkJoining the Facebook Fund for early stage founders

BERMAN: Leah kept tweaking her Boston model, but was eager to expand. A path toward scale emerged when she learned about something called the Facebook Fund, for early stage founders. It came with significant strings attached. If accepted, she’d get just $15,000 … and have to give Facebook 2% of her company.

SOLIVAN: Everyone’s like, no, that’s crazy. And I was like, ugh. It does seem crazy. But it also feels like an opportunity and a way for me to open doors that I didn’t have access to. Growing up on the East Coast, not involved in any sort of entrepreneurship, no network in the start-up world. And so I was like, I know that everybody thinks this is a bad idea, but I think there’s something here that I’m just going to make it into something that’s worth it. And so I ended up doing it. And so that 15K basically paid for all my flights back and forth because I was running the market in Boston. Boston was up and running, live, I have all these taskers and moms and everyone using the service. And then I spend a summer going back and forth to Palo Alto to do this incubator program at Facebook.

BERMAN: The program came, I assume, with other benefits that an accelerator would come with?

SOLIVAN: It did. It did. Lots of incredible opportunities to network. This is where I met Tim Ferriss, who became an advisor.

BERMAN: Pretty good one.

SOLIVAN: He introduced me to Ann at Floodgate. He introduced me to Steve Anderson at Baseline. I mean, they led my seed round. So it really was turning that 15k into the million dollar seed round I was able to raise at the end, but from the beginning I was like, If it’s just about this 15K, this is not a good idea. But if I can turn this into something else, then I’ll be happy. 

Copy LinkStepping down as the CEO of Taskrabbit

BERMAN: Yeah, okay. So let’s, let’s jump forward a little bit. The company is scaling, things are starting to work. And at some point you decide maybe you’re not the CEO of the company. What happened there?

SOLIVAN: I was an accidental solo founder, and I always wanted that business partner. I think it was after the Series A, I said, you know, this is a real company, and it’s scaling, and it’s turning into something really incredible. I really want to focus on product and technology. I really want to find that business person. I said, I’m open to a COO, and I’m open to a CEO. I think my mistake there was that the company was still so young. It was still so early. To remove the founder as the leader, a COO would have been fine, and in fact the second time around we brought in an incredible COO that’s been on this podcast before Stacy Brown-Philpot. She really helped me take the company fully to scale and to exit, but at this point the company still needed the founder to be the visionary and to be the leader.

And so, you know, we tried it. We had someone come in for six to nine months. We ended up hiring too many people, scaling up too fast, the burn got really high, and it was just kind of like, we need to get back to basics here and regroup.

BERMAN: Yeah. There’s a lot of discussion in the world about finding your technical co-founder. I think there’s less about the technical founder finding their business co-founder. So how would you advise a technical founder to think about that? 

SOLIVAN: If I could go back and do it all over again, I would have tried harder from the beginning to find a co-founding partner. Like, before I went to the incubator program, you know, maybe even before I left IBM, I would have taken the time from the very beginning to formulate the team that was going to build it.

And instead I was like, Oh, I can build this. I’m going to launch it. We’ll just kind of see what happens. And I think if I could go back, I would slow down those first few months and focus on getting the right team in place.

Copy Link“Everything broke at 50 people”

BERMAN: There’s a theory of organizational growth in factors of one in three. You’re one company, one person at three, at 10, at 30, at 100, 300, and so on. What piece of that journey was hardest for Taskrabbit?

SOLIVAN: When we hit 50 people, I feel like everything broke.

BERMAN: What happened?

SOLIVAN: Communications broke. Cross functionality between teams broke. The culture broke. Everything broke. It was like, oh, wow. We’re not this small company anymore where everything just gels and jives and everything just works. And, of course, marketing and engineering are on the same page because they’re working on the same things. And it’s like, no, it was not like that anymore. So I remember when we hit 50 people, it was kind of like, ugh, we need other processes in place now and we need organizational structures. We need HR. The whole company needed to transform at that point.

BERMAN: Yeah. I’ve spent a good bit of time in that 30 to 100. And there are a lot of things that happened. But the people who helped enormously, who were essential in getting you to that point, maybe don’t scale with the company anymore.

SOLIVAN: That’s hard.

BERMAN: So what did you do to deal with those things?

SOLIVAN: There were those transitions that had to occur where people just weren’t scaling.

I can remember certain instances around customer service, right? If you’re just a two person customer service team, you know, answering phones and chats and emails is very different from a 15 person customer service team and you actually need more structures and policies and scripts and all kinds of other things in place.

And so, those transitions are hard, but they’re necessary as well.

Copy LinkLearnings from bringing Stacey Brown-Philpott in as the COO

BERMAN: So what did you learn from the CEO hire that didn’t work out that informed bringing Stacey Brown-Philpott on as your COO? 

SOLIVAN: Well I think at that point I realized I had to stay in the seat as the founder, visionary leader, full stop. But I wanted to find a really strong COO.

I had met Stacey the first time around, but she had just had a baby. A five week old baby. And she was on maternity leave from Google, but I met her in a coffee shop, and she had tried the service to get some baby gear from Target, had a great experience. And she’s like, let’s stay in touch. And so a year and a half later, I called her.

BERMAN: She just wasn’t in a place where she was ready to take on?

SOLIVAN: She wasn’t. She’s like, listen, I got a six month maternity leave here at Google. It’s my first child. And so I’m gonna take that, but let’s stay in touch. And so we did. And she ended up being that right person 18 months later.

BERMAN: And how did you know she was the right person?

SOLIVAN: Chemistry. So, her and I, I mean, we work really well together. She had all the operational, all the business, all the finance components, and I had all the product, you know, technical engineering components. I mean, it was a lot of collaborative tissue, and she’s just fabulous. She’s just a pleasure to work with, you know. And I also felt like I was gonna learn a lot from her, and I did.

BERMAN: What’s something you learned from her that stood out?

SOLIVAN: Oh my gosh. I’ve learned so much from her around people, culture building. 

BERMAN: Was there something that she does to help build a culture that we could learn from?

SOLIVAN: Yeah, I think how to develop people and invest in them and give them opportunities for development and for learning and build that into the culture of the company. 

That 50-100 people range. I mean, that is like. The awkward tween years. You know?

BERMAN: Yeah

SOLIVAN: For me that was like one of the hardest points of the company because it was so awkward. 

Copy LinkHow a partnership with IKEA led to an acquisition

BERMAN: Today, Taskrabbit is in thousands of cities worldwide and has hundreds of employees. You might imagine a Meta or DoorDash acquiring the company. So when IKEA was named as the buyer, that raised a few eyebrows. Leah says the idea, at first, was just to partner with IKEA.

SOLIVAN: So IKEA was a company that was on my dream list for a long time because from day one, the highest volume task on the site was always IKEA furniture assembly from day one.

I mean, I was like going to IKEA, you know, outside of Boston and getting these flat packs with my little Allen wrench, like putting IKEA furniture together. So it was always a popular task, okay?

So they were on our dream list for a long time. Stacey got on board, was on Stacey’s dream list as well, and we were like, we gotta get, we gotta get into IKEA. We want to do a partnership with them. We want to be in-store. We want to be part of their checkout process, you know. But they were really very elusive. Very difficult to get to. Private company, family-owned, out of Sweden. How do you contact IKEA? No idea.

BERMAN: You going for Swedish meatballs? Yeah. Talk to people?

SOLIVAN: Just like, I don’t know. No, it was really hard. We worked all kinds of different angles, approaches, and we finally got together. Literally after a couple years, I got this random consultant who was taking a bunch of companies on tour from Europe to the U. S. One of the companies on his tour group was someone from IKEA. We’re like, bring the tour group to the office. We want to meet the IKEA person and everyone else that’s there too.

The tour group came by the office. We, Stacy and I paid very special attention to the IKEA exec, made sure she had our business card, we got her business card, and then that was the in. That’s where we were able to kind of follow up.

We pitched a partnership with them in store. That was the dream. And at that point we were live in London internationally. London was our fourth largest market. It happened to be IKEA’s first largest market in the world. And we’re like, well, let’s do it in London. And so we did this partnership in-store in London.

You’d buy IKEA furniture on checkout. You could sign up to have Taskrabbit go home, assemble it for you. Deliver it and assemble it. Drove up the average order value immediately for IKEA. They were psyched. They were like, this is amazing. That AOV in our store now went way up compared to the other stores.

Drove revenue. And we were excited we had all these new customers. I mean, it was a win-win. It was so obvious. We were not thinking acquisition. But, IKEA started thinking acquisition. And at the time, we were also doing an integration with Amazon. We’re doing on the Amazon checkout. So you buy a flat screen TV.

It was like, do you want Taskrabbit to come and install this? We were integrated with Wayfair as well. So we had all these service providers were integrated, and I think IKEA probably saw that and was like, we want to own this. The thing with IKEA that was surprising to me and exciting was that there was so much cultural alignment because their brand and their culture at IKEA is really focused on sustainability.

We visited their offices in Sweden, in Copenhagen, and everything in the office is made out of recycled materials. Huge focus on sustainability and community and giving back to the community. 

I mean, lots of value alignment with how we thought about Taskrabbit as well. And so when the conversation turned to, Hey, we might want to own you guys. It was very clear that it would be a nice integration with the team that the brands would integrate well, and I think we’ve really seen that played out because they’ve been able to keep it stand alone. They haven’t absorbed the brand into their own and they continue to do all the other jobs and tasks that Taskrabbit usually does.

Copy LinkStepping away from Taskrabbit after a decade

BERMAN: Was it hard to step away from the business?

SOLIVAN: Yes, it was. It was bittersweet. It had been 10 years. I was ready. At that point, I had promoted Stacy to be CEO. I was having my second child, and so it was a good time for me to transition to the board, and I was really happy about how that all worked out.

I mean, honestly, to this day, to be able to walk into IKEA and see the task, I’m just like, it feels so good to me to know that, even without me, it lives on.

BERMAN: Do you miss operating?

SOLIVAN: I don’t. I don’t. People ask me that a lot because I moved to the investor side and again, I think it goes back to, I accidentally started this company because I believed in the technology and I wanted to see the technology through, and I’m very motivated by learning new things, and being an investor is the best thing for me. 

I’m learning new technologies all the time. I’m learning about new business models all the time. I’m meeting new people all the time. So it’s very invigorating, and I feel just as busy as I did when I was running a company, but without the pressure. The pressure is so different.

BERMAN: What’s the question you wish I’d asked that I haven’t asked you?

SOLIVAN: I think this is relevant to both me as a founder and investor, but what is the biggest surprise for me on the investor side? Because it was a huge surprise.

Copy LinkThe question that Leah Solivan wished she asked investors

BERMAN: What’s the biggest surprise for you on the investor side?

SOLIVAN: Coming from a founder mindset, I was always so concerned about the competitive landscape for Taskrabbit. I mean, I would lose sleep over it.

You know, there was Zarly, there was Homejoy, there was Handy, there was Thumbtack, there were all these competitors. What I never thought about was: who is competing for dollars in my investors portfolio? And now as an investor, what I realize is I was in a portfolio with Uber. 

And, you know, Taskrabbit versus Uber, like they’re very different businesses, okay? Just to be honest. I had a lot of trouble and one of the raises, it was like the series C or D, it was like a later stage raise. And my series A investor kept saying like, we’re tapped out. Like, we’ve invested this whole fund, you know, like you were one of the last investments in the fund. And I’m like, that fund had already exited, they had already done well, like nothing that they would have put in a Taskrabbit at that point was going to move the needle on that return profile.

So they’re not going to put any more money in, right? And so that was the biggest surprise to me as an investor was: I was completely missing some of the dynamics that were very important to my fundraisers.

BERMAN: So how does that inform what entrepreneurs should be asking you and other investors when they’re raising money?

SOLIVAN: I would ask them: What are you saving for me as a company? 

What do you got earmarked for me in this fund, right? And I think understanding that along the way would have been helpful in planning how and when we did fundraisers. And I had no concept of that, which I think a lot of founders probably don’t. But that’s all your investors are thinking about. That’s all they’re thinking about. So it’s completely different than how you are thinking.

BERMAN: That’s phenomenal advice. Thank you. It’s a great conversation. Appreciate you being here.

SOLIVAN: Thanks for having me. 

BERMAN: Since leaving the CEO seat at Taskrabbit, Leah has refined her reflections on the experience and used them to inform her investing. 

With that kind of self-awareness and flexibility, you can hear how she’d make a great advisor — and that, my friends, is no easy task.

I’m Jeff Berman. Thank you for listening.