First Contact Transcript

Episode 23: TaskRabbit Founder on Finding Opportunity in Uncertainty

First Contact is a production of Dot Dot Dot Media and iHeart Radio.

Laurie Segall: There was this certain heart, back in- in 2008, 2009, and there were things that got solved that I think were really interesting and really changed things. I don’t know if this is just me being nostalgic for it or if this is real, but I can sense that same moment happening now, because there’s a lot more constraint, just in the last couple months.

Leah Solivan: It’s forced by the constraints, right? It’s like, we were so constrained by not having outside capital, by not having a team around us. Like, we just had to figure out how to do everything ourselves. And I think that forces, actually, some different solutions. I think we’ll see more of that, you know, now, and into the next decade.

When I started covering tech in 2009 we were coming out of the recession, and there was this  new creative class emerging.

Uber and Lyft redefined transportation, Airbnb – shook up the travel industry — and Taskrabbit — helped pave the way for the gig economy. 

But everything feels uncertain again. I’ll say this – a decade later –  I sense that same creative spirit in Silicon Valley.

It’s the feeling of opportunity that emerges from chaos…I believe that once again there will be companies that grow out of this moment, this moment that’s filled with extraordinary pain and uncertainty…

My next guest is someone who knows a lot about this – Leah Solivan. She’s the founder of TaskRabbit – a company born out of the 2008 recession…

I’m excited to have her on because… this isn’t an afterschool special, so I don’t want to sugarcoat it – what she did was extremely difficult.

Building a company that changes the world is hard. So is battling your brain, so is taking risks. Add all of this to the backdrop of a global pandemic….and now we’re talking… 

It’s been over a decade since she launched TaskRabbit — and now, Leah helps run an early investment fund called Fuel Capital, and she is not afraid to talk about mental health, about stress and anxiety, you name it — all while building a startup.

It stems from her own experience doing something big… and not shying away from the chaos and uncertainty… 

…but before we get to the interview.. I just want to tell you guys just how much I’ve appreciated your feedback and your ears during this time. 

We are nearing the close of our first season – so I’m a little sentimental and I’ll say this, Please stay in touch with me. We’re launching a newsletter this summer and it will be your best source to stay in the loop about any extra episodes, virtual Town Halls we’re hosting and other future projects that I’m gonna be working on. 

So, sign up at dotdotdotmedia.com/newsletter. I promise I won’t spam you. 

Okay, let’s jump in. 

I’m Laurie Segall and this is First Contact 

Laurie Segall: I wanna kind of start at the beginning and just give you the, the simple what I ask everyone as we start this, which is, how are you doing?

Leah Solivan: It’s such a funny question these days, isn’t it? Um, usually I’d respond, “Great. Everything’s great. Everything’s fine.” And I feel like I’m hanging in there. It’s just a lot right now. And, um, I think also having the perspective about, you know, what’s going on in the news, what’s going on in the front lines, what’s going on in hospitals, I mean certainly gives you perspective on how grateful I am, and fortunate and privileged I feel to be where I am. I’m at home. I’m safe. I’m with my children.

Laurie Segall: Yeah.

Leah Solivan: Everybody’s healthy. But you know, between the homeschooling and working full time and, you know, not having the support system that I used to, it is, it has been a complete shift and a complete transition. So I just feel like I’m hanging in there.

Laurie Segall: We start out each of these episodes with this idea of first contact. And this one is near and dear to me because I was thinking about our first contact, and in tech years, it was a long, long time ago. It was-

Leah Solivan: Ages.

Laurie Segall: Do you remember it? 

Leah Solivan: I mean, I do actually. You interviewed me on CNN. I was terrified. Um, and I mean, it must’ve been a decade ago, at least.

Laurie Segall: Yeah.

Leah Solivan: Something like that.

Laurie Segall: Yeah. I went back, in preparation for this, I went back and I found the interview.

Leah Solivan: Oh my God.

Laurie Segall: It was from 2011. It was 2008 when you started TaskRabbit?

Leah Solivan: Yes. Yes.

Laurie Segall: And then in 2011, I interviewed you and I remember this idea of the gig economy and all this. This didn’t, you know, you guys made this popular. Like, this didn’t really exist. And so, I was on the startup beat. I had helped create the startup beat at CNN.

Leah Solivan: Yeah.

Laurie Segall: And I remember, we were following a TaskRabbit around-

Leah Solivan: Yes.

Laurie Segall: Named Suzie.

Leah Solivan: Yes.

Laurie Segall: And we were interviewing you about it, and talking about this thing called the gig economy and this idea of having other people help out with your errands. And that’s when I met you for the first time.

Leah Solivan: Yes. I remember. I remember standing outside around the fountain, I think. And you were interviewing me outside and New York was bustling and it was a beautiful day. And, yeah. That was the first, the first interview we did together.

Laurie Segall: It’s almost, um, I look back at that and it almost feels, um, I don’t know what the word is. But, it’s so nostalgic to look back at that moment in tech because … And we’ll get into this … You founded TaskRabbit out of a pretty chaotic moment in 2008. But there were so many interesting tech companies that did come out of that moment. But this idea of, um, New York bustling and, and you know, people being able to come into our homes and do things and help us out and, and almost this idea that you had that gave birth to, to this whole industry of the gig economy. It was so special. And, and now fast forward all these years later, over a decade later, and we’re sitting here. I’m interviewing you self isolated in my home, with this idea of when will we allow people in our homes again and what’s gonna happen? It’s just, it almost feels very nostalgic, sitting here talking to you, especially given that I had the opportunity to interview you at the beginning of that.

Leah Solivan: It does. I mean, it was a different time. I mean, three months ago was a different time. I think the thing that though, gets me excited and gives me comfort about the future is, as you said, when you think about all of these companies that were innovated out of that chaos and out of that crazy time, there were so many. I mean, it was Lyft. It was Uber. It was Airbnb. It was TaskRabbit. There were just tons of great innovations that happened in the gig economy, in the peer to peer marketplaces. And so I think now is a time for another step change for consumers. And we’re gonna see a lot of behaviors change and a lot of new innovations come out of, you know, this time and throughout the next decade, that we’ll be talking about, you know, in the year 2030.

Laurie Segall: I wanna go back to 2008. You were at IBM. Um, and you decide right before the recession to quit your job. You’re a rising star at IBM. And I know for a fact, having covered Silicon Valley for many years, that it is not easy to be the woman in the room at many of these places. But you made the decision to kinda quit your job. And I think, and I will say this, I think, especially in media, sometimes we have the luxury of perspective to look back and say, “And then she quit her job. And then she created TaskRabbit. And then it sold for all this …” You know? I think that is way too simple of a story. So just take me back to Leah, before the, before we entered this recession and before all this happened, at IBM and thinking, you know, “Something is broken and I wanna fix it.” What were you like back then?

Leah Solivan: Yeah. I mean, that’s a great question. I think I always tell the story as this moment of inspiration and it was like poof, I waived a magic wand, right, and I was off starting my company. But, I think the relevant parts now, um, are so much more detailed and there’s so much more rooted in the economic time, in the market that was emerging. And so, it was February of 2008 when I was working at IBM. I did have the idea because I was out of dog food one night and I thought, “There’s gotta be a way to get this dog food.” The iPhone had just come out, you know, a few months earlier and so all of a sudden, we all had these little mobile devices in our pockets that we weren’t really fully utilizing the technology on yet. And as an engineer myself, I got really excited about those emerging technologies, particularly mobile location based awareness and then social technology. I mean, Facebook was really just breaking out of the college scene at the point, and becoming more mainstream. So I spent the next few months thinking about the idea, talking to anyone who would listen to me about it. I had gotten connected with Scott Griffith, who was the CEO of Zipcar at the time, in Boston. And he really took me under his wing. And I was still at IBM then, but he said, “You know, I really think you’re onto something. The way I think about Zipcar and getting people to share resources in the neighborhood is very similar to how you’re thinking about …” At the time, the company was called Runmyerrand.com. It wasn’t even called TaskRabbit yet.

Laurie Segall: Mm-hmm.

Leah Solivan: And he really encouraged me to make the leap. Now, I had no idea that this recession was coming. I had no idea that the stock market was gonna crash or that all of these people would be laid off. I ended up leaving my job in June of 2008. 

Laurie Segall: Do you remember the day you left your job?

Leah Solivan: I do. It was June 25. I remember going in and giving notice to my manager. And, you know, it was sort of that frantic, they tried to keep me. They were like, “No, no. You’ve gotta meet with my manager.” And then that manager’s like, “No, no. You’ve gotta meet with my manager.” And I was like, you know, three or four managers up the chain, by the end of the day. Right? But I had made the decision that I wanted to do something more. I love engineering. I love programming. I love creating. But, I had all these other skills that I wasn’t using at IBM. And I just was really passionate about the idea. And that’s sorta what gave me the confidence to, to walk in that day, quit my job and make the leap.

Laurie Segall: I guess I go back to this idea of like, were you afraid? I mean, it’s like, you look back at all you were able to do, and of course, you were able to do it. Right? You have the luxury of perspective right now but in that moment where did that confidence come from? And, and maybe this is kinda one of those like, how do you, how do you talk to yourself when you don’t even, you know you can do all these things, but when you’re actually going in to do it, it’s much more complicated, you know, and it does take a certain … And maybe what I’m getting at is, it takes a certain kind of person to follow through with that feeling that they can actually go do it and then go do it. So how did you prepare yourself mentally for it? I mean, and now having the luxury of perspective, you know, what do you wish you could go back and tell that girl?

Leah Solivan: Well I mean, it’s funny because I, I was hesitant. I was afraid. But I also sort of had hit my max of what I felt like I could do at IBM, as far as what would make me happy. There was plenty more I could do there, but I knew it wasn’t gonna make me happy. And so, I remember having this conversation with myself. And it sounds kinda funny, but I remember this clearly. And I was saying, you know, “How are you gonna launch a company? How are you gonna build a product? Like, all you’ve done is program. You’ve sat in a cube by yourself and you’ve programmed software. You’ve never interacted with customers. You’ve never raised money from investors. You’ve never hired. You’ve never fired. Like, you don’t know how to do operations.” But I think I realized that … And this sounds kinda silly, but I told myself, “You know what, Leah? It is not rocket science. You’re gonna figure it out.” And I literally made the decision that I was gonna stop worrying about all the things I didn’t know how to do, and I was just gonna go figure it out. And, I am a constant learner. I like to learn all the time. And so that part of it, I decided to look at as very exciting instead of very terrifying. But it was like this active mental shift I had to make before I could get comfortable making the leap to do it.

Laurie Segall: You actually launched TaskRabbit, and I think this is so important to talk about so much was happening in 2008. You know, there was so much chaos. Everyone was talking about, you know, Wall Street was under fire. And I think this, this moment for me is really fascinating for technology because you, you know, you hold up your iPhone and you talk about the iPhone had come out, the app store had launched. There was just this canvas for creativity for the smart people who were paying attention. And out of that came TaskRabbit. So, tell me about, actually launching Task Rabbit in this environment. What did you learn?

Leah Solivan: Well, you know, I spent sort of those June summer months coding the first version of the site. And I was talking to potential customers. And, I mean, I was literally sitting at the local coffee shop actually coding. And then as customers would come in, I’d be like, “Hey, what do you think of this? Would you use a service like this? What would you need outsourced and how much would you be willing to pay?” And so, I wasn’t actually even sure if the market was there yet. And then September 2008 rolled around. And the stock market crashed and everyone was being laid off. And the world changed overnight. And very much like the world has dramatically shifted overnight in the last couple of months. And that was a hard time because I was thinking, ” Oh my God. What did you just do? You left this cushy job at IBM and you’ve decided to focus on this company that you don’t even know how to build. Like how are you gonna do this?” Now, because the company was focused on putting people to work, it actually very serendipitously turned out to be the perfect time to build a company like TaskRabbit. And I wish I could say I had seen that coming and I had the foresight from, you know, February and June, like to know that that’s what was gonna happen, but I didn’t. I honestly didn’t. And part of it was, was luck in some ways, that the timing hit for this need and what I was building was filling a gap. And sometimes those things just cannot be predicted.

Laurie Segall: When I look at having covered entrepreneurs and the ones who succeed throughout the years, I think there’s some qualities that a lot of them have, right, that I could just see. And I think one, the first is probably resilience. Another one is being scrappy. So I’d be curious to know how back in, in the day that played out? Um, how were you very scrappy in building out TaskRabbit?

Leah Solivan: Yes. Uh, a lot of scrappiness. And that, that’s just kinda in my DNA anyway and that’s kinda how I’m built. So that was a good thing. Because when the recession hit in September, yes, I had to question everything, but what I didn’t have to question was whether or not I could figure it out, whether or not I could figure it out, whether or not I could actually pull it off, whether or not I could do it. I mean, it was just a matter of, like, finding new ways, and coming up with new things, and- and creative outlets, to explore. And so, you know, when I left IBM in June, I thought, “I probably have about six months of runway,” where I cashed out $28,000 from my IBM pension, and I thought, “Okay, $28,000, I can make that last six months, I can, you know, invest a little in the company, and I can live off of this.” And when, of course, September hit, it was an awful time to be raising money. There was no way I was gonna be able to raise any money before the end of the year. And so bootstrapping became sort of a necessity, and- and the mode that I stayed in for the next 18 months. It really wasn’t until the following year, near the end of 2009, that I was able to raise a seed round of funding from investors out here in the Bay Area. Ann Miura-Ko at Floodgate Fund led a million dollar round of seed funding. But prior to that, it was maxing out credit cards, it was bootstrapping, it was just running super, super lean. It was just me. I couldn’t hire anyone. Um, so I was the first TaskRabbit ever, and I did a ton of errands-

Laurie Segall: That’s so inter… You were the first TaskRabbit.

Leah Solivan: Oh, yeah. I did a ton of errands all over Boston.

Laurie Segall: No! Tell me- tell me, so you were actually going… if I went on the earliest iteration of TaskRabbit-it would’ve been you, the founder of TaskRabbit, doing my errands?

Leah Solivan: Yes. All the time. yeah.

Laurie Segall: That’s incredible.

Leah Solivan: What was awesome about that, so I had this little Honda Metropolitan scooter-

Laurie Segall: Uh-huh.

Leah Solivan: … that I would just ride around the city, and I’d pick up people’s dry cleaning, and I’d deliver groceries, I’d do all kinds of things. What was great about that time, as I look back, is that it really, really taught me what the customer needs were, not just from the standpoint of clients that needed- tasks done, but what the actual Taskers needed to be successful. And so I became sort of obsessed with the supply side platform, and the supply side marketplace, and really focused in on, what are the tools I need to build to make sure that they can be successful and build out their own businesses, like entrepreneurs, on this platform? That is an insight I wouldn’t have gotten unless I had been actually a TaskRabbit doing the jobs myself as well. So I think in times of scrappiness, in times where- where you’re really forced to bootstrap and be lean, I think it can actually be very beneficial, because you get really, really close to the customer, and I think you think and you build differently.

Laurie Segall: God, I remember when, even, like, Dennis, the founder of FourSquare, I remember back in the day, going to South by Southwest in, like, 2011, and calling up FourSquare and being like, “Okay, who’s…” Trying to call their PR person and be like, “Who’s gonna be the big company?” And just Dennis answers the phone, ’cause he’s-

Leah Solivan: Yes.

Laurie Segall: … the PR people. I don’t think people understand, especially as people get bigger, and as we- we glorify companies, as- as they become companies, and- and put in the press, like, how involved the best founders are in a very scrappy way, to the point where you are probably going and getting the groceries on your scooter to try to understand the product. I don’t know if people fully understand that that is how some of the best businesses are built.

Leah Solivan: I think that some of that is, uh, forced, as well. It’s forced by the constraints, right? It’s like, Dennis started around the same time that I did. He was 2007, 2008 as well. And we’ve talked about this before, Dennis and I. It’s like, we were so constrained by not having outside capital, by not having a team around us. Like, we just had to figure out how to do everything ourselves. And I think that forces, actually, some different solutions, some different product solutions. I think we’ll see more of that, you know, now, and into the next decade. I think as the market improved, and more capital, you know, came into the market, people, founders, didn’t need to be the ones on the ground anymore. They could hire out for that-

Laurie Segall: Yeah.

Leah Solivan: … right? And they could learn from, secondhand, from those people. But things get lost in translation-

Laurie Segall: Yeah.

Leah Solivan: … so I think it’s actually kind of interesting to be super scrappy and super bootstrapped in the beginning, and really understand the market.

Laurie Segall: There’s something really interesting about this moment, having covered your story back in the day, Dennis’s story, and having gotten my early start in my career, watching entrepreneurs make something out of the recession, and make something out of this moment of constraint. I think part of why I’m excited to be here with you is- is because I sense that this is another moment of constraint, and I think Silicon Valley, and you- you’re an investor now, and we’ll get to that, like, got very noisy, right? And a lot of people outsourced, outsourced, outsourced, and there was this certain heart, back in- in 2008, 2009, which made way for companies like Airbnb, and Uber, and- and, you know, there were things that got solved that I think were really interesting and really changed things. And I think… I can sense that same… I don’t know if this is just me being nostalgic for it or if this is real, but I can sense that same moment happening now, because there’s a lot more constraint, just in the last couple months, you know? I- I hear Silicon Valley chatter again. I’m beginning to see the same entrepreneurs who have been kind of distant for a while beginning to kinda come back and solve some real problems, and I’m assuming you, as an investor, I- I’d be curious to know, like, what are you sensing? You invest in early-stage companies. What is the feel now, sitting in- in Silicon Valley, as- at another moment of constraint?

Leah Solivan: Yeah, I mean, I think- I think it is real. This is a real moment of inflection, I think, for technology companies, for consumers. So as an investor, I’m incredibly excited. I’m really excited. I can’t wait to see what is born out of this moment. And I just hope I’m- I’m part of it. I hope I’m the one funding it, right? Like, that’s the job. It is the dream job. This actually, as an investor, could be seen as a dream moment. And so I think the opportunity is there to really drive innovation, to find founders that are resilient, that are scrappy, that are innovating, you know, in a different way, on a new level, and to really support them, and- and be apart of it.

Ok we’ve got to take a quick break to hear from our sponsors, more with my guest after the break.

Laurie Segall: You know, we saw what kinda came out of 2008, 2009. Like we saw Airbnb, Uber, Lyft, TaskRabbit, you know, we saw the sharing economy. Um, this is very near and dear to me, because this is where I got my start covering technology. What kind of industries do you think are, now we’re kind of seeing are, like, ripe for some disruption right now?

Leah Solivan: Well, back in 2008, it was really driven by technology around location, around mobile, around social, right? And, like, so people were thinking about different ways to mash up those technologies. Airbnb, Uber, Lyft, TaskRabbit. Now, there’s this whole step function change in how we’re working. We’re all working remotely from home, work will never be the same again. It’s been, now, almost two months of sheltering-in-place, of working from home. I mean, there’s no better way to shift consumer behavior than to actually put constraints around it. And I think at first, people were like, “Oh, this is gonna be so hard, I’m working from home.” And then, you know, Zoom just completely took off and blew up. It’s like, Zoom is the next Facebook now. Zoom is the next platform. Like, what does that mean for- for remote work, um, and for collaboration? And then I think, you know, people are gonna figure out new ways of balancing working from home, working in person. Do I think that we’ll, you know, as soon as this shelter-in-place is over, do you think we’ll all go back to the normal in-office, face-to-face, 9:00 to 5:00? I don’t think so. I don’t think-

Laurie Segall: Yeah.

Leah Solivan: … you know, unless you really have to be there in person, people now have been sort trained to utilize these remote tools. And they’re okay. I mean, I think at best they’re kinda mediocre, because they haven’t been stress-test, the way- the way that we have stress test-

Laurie Segall: Yeah.

Leah Solivan: … them over the last two months. And so it’s in times of stress, right, that entrepreneurs and innovators are gonna say, like, “Okay, this worked to a certain extent, but like, here’s the next level of it, here’s the next iteration, here’s the next phase.” So remote work is definitely an area I’m really excited about. You know, in 2008, it was all about how the future of work was changing, and how jobs were becoming more flexible, and the gig economy was emerging, and now it’s like, “Okay, we’ve seen what the future of work is.” Like, “How does that now evolve into the next phase, into the next decade?” I think another area that’s super exciting is around digital health. I mean, telemedicine-

Laurie Segall: Oh, yeah.

Leah Solivan: … just the necessity of it has just blown up. But again, like, the tools have- have not been stress test the way that they have in the last two months. And so there’ll be new innovations in digital health, in wellness, in telemedicine. And then the third area I’m really excited about and watching closely is just education. I mean, online learning. It’s like, again, with all the schools closed, my kindergartener is on Zoom, and she’s on Duo, and she’s, you know, she can barely spell, but she’s, like, on iMessage, texting with her teacher and her friends. And it’s like-

Laurie Segall: Yeah.

Leah Solivan: … a whole new world of learning. And there haven’t really been, um, great tools or platforms that have emerged as the leaders in that space, particularly for elementary education. And so I think that’s a huge opportunity, that we’ll see innovations around as well.

Laurie Segall: Yeah. I mean, it certainly feels like all of the sudden, overnight, the only means towards human connection we have is through this screen, right? I’m Zooming with you right now in order to do this interview. But it seems like a lot is lost in context. If we wanted to- to have a moment to kinda go off on our own, or come back, there’s- there’s… it’s like, you gotta be all in or you’re all out. The- there’s something that- that feels a little bit… like, it doesn’t 100% mirror the human experience. And this is me putting on my tech and humanity hat. Um, and  I I think you’re right. I can sense that there’s gotta be something else, right? Like, Zoom is okay, but all of us are getting exhausted, I think, by this one way experience-

Leah Solivan: Yes.

Laurie Segall: … that leaves no room to have kind of the serendipity of the human experience, and the lightness that comes along with just being around a room, and having that casual element. So I’d be curious, let me know what you end up investing in-

Leah Solivan: I will.

Laurie Segall: … do it quick. Please, Leah. Uh, it’ll be very interesting. I wanna go back to, uh, to the early TaskRabbit days. Uh, sorry to take you on that tangent. I just think it’s so fascinating, and you’re such an interesting person for- for me to pick your brain on this, because you were at the beginning of this, um, and I think you very much represent, you know, innovation out of constraint. And so I go back… I didn’t realize that you became, you were the i- initial, the OG TaskRabbit-

Leah Solivan: Right.

Laurie Segall: … which is I think is- is just fascinating. But then I saw that you actually went on craigslist to try to find TaskRabbit people. This was before you guys have extensive background checks and all this kind of stuff, and that was, even when I interviewed you in 2011, I remember asking you about that. But back before that, you went on craigslist for your earliest TaskRab- people for TaskRabbit. And the- the way you decided if you would hire people was if they were people that you would trust to go into your grandmother’s home? Was that it? Can you just-

Leah Solivan: Yes.

Laurie Segall: … take us to that? What- what was the thinking behind the- the next iteration of, we go beyond Leah as TaskRabbit number one, and into-

Leah Solivan: Yeah.

Laurie Segall: … craigslist, phase two?

Leah Solivan: Right. Yeah. Well, I realized that I couldn’t actually do it all if this company was going to scale and be successful. And so I put the ad on craigslist, and, I wanted to see just who would respond. I mean, I was actually very curious, you know, what types of people would respond to the ad. I met 30 TaskRabbits in person, over coffee, at the local coffee shop where I was spending my days coding away. And I met with them for about 30 minutes at a time, and I just sort of assessed, like, is this someone I would feel comfortable sending over to my grandmother’s house? I didn’t have kids at the time, or else I would’ve, you know, thought about putting them in my house. But- the- the point was, is, like, can I trust this person with my loved ones, with someone that I care for and really love, and that, you know, is vulnerable, you know, is- is gonna be, maybe, a little more vulnerable than the rest? And so,, those early days, I had to sort of make that gut check and say, like, “Oh, okay, yes, I definitely trust this person to, you know, drop groceries over at my grandmother’s house.” I knew, though, that I needed to build in some background checking, and some automation, and an application process, and- and some protections. I mean, remember, this is a time where jumping into a stranger’s car was unheard of. Like, you would not do it in 2008.

Laurie Segall: The thing is, like, I don’t think people realize that. I just wanna, like, set everyone back, like-

Leah Solivan: Yes!

Laurie Segall: … s- 8, 10 years, like-

Leah Solivan: It wouldn’t happen.

Laurie Segall: … I… ’cause I… maybe it’s ’cause I remember going on camera and being like, and doing kind of a bit of a cheesy stand-up and being like, “Imagine going into a stranger’s home-“

Leah Solivan: Yes! Terrifying.

Laurie Segall: … “can you imagine going into a stranger’s car via an app?” Or like, “Would you ever hire a stranger to do a chore for you?” Because I remember, those were my lead-ins-

Leah Solivan: Yes.

Laurie Segall: … um, because at the time, it was just unimaginable. 

Leah Solivan: It was.

Laurie Segall: … and then everything changed so quickly, and I think people forget that you could’ve been looked at as a little insane, and I think that’s important for people to understand. I’m sure, when you started out, people kinda said, “No,” or kind of looked at you a little bit like, “This girl’s just kinda crazy, she’s, you know, just too ambitious,” or whatever. I think that’s really important for people to understand, that all of this seemed insane until you came along and until it wasn’t.

Leah Solivan: Until it wasn’t. And that- that’s kind of the point. Like, I actually think that because of the economic crisis that we went into in 2008, and because of the stress put on the market, and the stress put on the labor market, I mean, that really helped shift consumer behavior into making that step function change, into being okay with, you know, inviting a stranger into your home to do a chore, or, eventually, jumping into a stranger’s car, which didn’t come that much later, you know, it was 2010, 2011-

Laurie Segall: Yeah.

Leah Solivan: … when Lyft and Uber took off. So, it is in times like these that the consumer is actually open to change. And it’s really hard to force that change when everything is sort of normal, and going well, and that’s the hardest time to make a change. But behavioral changes come when there’s stress on the system.

Laurie Segall: Do you remember, out of curiosity, just, like, go back with me in time. Do you remember the biggest no you got, or the most, like, the most frustrating, no or… ’cause you went to, I’m sure, a lot of investors, or you- you left a job that was cushy, like, you know, d- do you remember any specific interaction that sticks with you of someone who just did not believe in you or this idea?

Leah Solivan: Absolutely. Like, I just… more than one, honestly. Um, I mean, I talked to every investor I could get introduced to in the Boston area between, I don’t know, September of 2008 and maybe the summer of 2009. I mean, it was a long time where I would just meet with investors, angel investors, VCs. Now, at that time, it was also not a time where there were a ton of seed investors-

Laurie Segall: Yeah.

Leah Solivan: … set up quite yet, particularly on the east coast, particularly in the Boston area. So Founder Collective hadn’t even started yet. I actually met those guys, you know, right when they were raising their first fund. So it was a different time for venture as well. But, you know, I remember talking to, um, you know, potential advisors that I wanted to bring on, or, potential angel investors, and telling them about the idea, and they were so skeptical. So skeptical. And-

Laurie Segall: Like what? What did they say?

Leah Solivan: Well, one thing in 2008 that wasn’t quite apparent, at least on the east coast, honestly, at the time, was that social networking was going to be a thing. And I remember Facebook was started in Boston, and Mark went to the west coast to get funding. 

Laurie Segall: Mm-hmm.

Leah Solivan: … you know, Boston, and that, the east coast area didn’t feel like they had missed or lost that yet, right? because it wasn’t big enough yet to be a miss or a loss. And so everyone was still- And so everyone was still very skeptical that, “Oh, this other entrepreneur Mark, you know, he’s out on the West coast now and he raised all this money and like but, we don’t really believe in it still.” So there’s a little bit of that. I literally had um, a pitch deck that I would show investors for East Coast investors and then a different pitch deck for West Coast investors-

Laurie Segall: Wow.

Leah Solivan: … because the conversations were so different, specifically around social and whether that was gonna be a long standing trend or if it was just a fad.

Laurie Segall: Wow. That’s interesting. I saw something you wrote that I thought was, was great when you talk about, having a founding story, you gave a commencement speech and, and I think you, you spoke about this. You talk about having a founding story has three parts. A personal backdrop and moment of inspiration and innovated path forward. And I think we talked a little bit about your personal backdrop of, you know, the problem that led you to do TaskRabbit. And oftentimes we oversimplify these stories, but I do think it’s really important to have these, you know, because they are rooted in something. And, and even as founders, like there’s a reason why you become obsessed with something and why you drive towards something. And you had your moment of inspiration and then there’s something else you wrote. You said your, a big lesson you have is to have big, hairy audacious goals, but take baby steps. And you even went on to compare it, which I, I absolutely love to where the wild things are. Um, what was your big audacious goal and then what, what were the baby steps that you had to take to, to achieve them?

Leah Solivan: Well, it became apparent in September of 2008 that the world was changing and that I had started this company as an errands business, but that what I was building actually fit into the market in a much bigger way. And so the vision very early on became, we’re gonna change the future of work, we’re gonna change the labor markets, we’re gonna change the way people work and we’re gonna make them successful working in a new and flexible way. That was the big hairy audacious goal. And it’s funny because you know, investors, customers would look at TaskRabbit and they’d be like, “Oh, that’s a service where I can, you know, get my dry cleaning picked up or get my groceries delivered.” And yes, that was the easiest way to explain it to someone who needed to understand it quickly. But my vision was way, way, way bigger than that. And it was very ambitious, right? And so if you share that very ambitious vision with an investor in the beginning, chances are you would be laughed out of the room. And that’s the type of big hairy audacious goal I think is the most interesting. Come up with something where you will be laughed out of the room because it’s so big and so ambitious and everyone’s just kinda like, I don’t even understand where you’re going with this. And so that was the goal at the time. I think what I realized is I had to break it down into these little pieces. I had to tell customers and investors that yes, you can get your groceries delivered. Yes you can find someone to help you pick up your dry cleaning because you know, feeding them that whole big vision was too much at once. And I had to take baby steps to get there, um, and tie all the dots together. It was like, you know, putting all these points on the board along the way that would lead us to the overarching goal, which in the end, as I look back, you know, a decade later I can say like, yeah, we did a lot to change the way the labor market worked over the last decade. And yes, this is a new phase of work. And yes, the gig economy stayed and it’s here and it’s, you know, continues to evolve today. But that wasn’t apparent in 2008, 2009 and 2010. So it was about kind of having that overarching vision, but making sure that what you were doing on a daily basis actually was gonna push the business forward and closer to that vision in some way.

Laurie Segall: When you look back, and you talk about having these big goals and, and you can have the luxury of perspective and you kinda look at what you were able to do, you know, no one I know who’s ever been able to do anything big, hasn’t had big failure or hasn’t had to just, just get it knocked out of them because if you’re the kind of person who has the ability to have these big lofty as you call them, like hairy goals, right? Like from where the wild things are, then I think that probably comes, that comes with the ability to fail pretty spectacularly. So was there a moment that you could go to in this journey of TaskRabbit that you just felt like that this was just like a very, very dark, dark space for you, that you felt like, a failure in, in some capacity.

Leah Solivan: I mean, I honestly had a lot of those moments. There were three major ones I, like just hit me when I’m hearing you ask the question. And I think, you know, the one that I’ll, I’ll tell you about … well, I’ll tell you the three quickly and then I’ll dive into one. I mean, it was when I had to lay off 30% of the team, huge failure, um, near the end of the company when we were getting acquired, I was $3 million short of profitability. That $3 million raise literally almost killed me, put me in the hospital. You know, and then it was like early on, just like the product was not performing and we had to make this huge product shift into a more mobile centric product and away from the web. So it’s like fundraising failures, it’s people failures, it’s product failures, that were really, really difficult. And I think every day was sort of this roller coaster ride of ups and downs. And there were some really exciting things like being on CNN with you or you know-

Laurie Segall: Yeah.

Leah Solivan: … we were on Good Morning America one morning and we had so much traffic that the servers went down or you know, really exciting things happen too, our big fundraises that we did and announced. Um, and I think what I realized as a founder is that the highs, versus the lows were so dramatic that I couldn’t let myself ride that roller coaster fully. I couldn’t let myself feel great about the highest highs when I knew that around the corner there was gonna be a failure or a lowest low because it was just, it was too jolting. It was like-

Laurie Segall: Yeah.

Leah Solivan: … just too emotionally draining. And so I kinda learned how to stay level throughout the whole thing.

Laurie Segall: How?

Leah Solivan: Yeah.

Laurie Segall: You hear a lot of founders talk about that rollercoaster where the highs are high and the lows are low. How do you find that middle ground? Like what did you, what did you do specifically that, that helped you balance a little bit of, of the extremes?

Leah Solivan: You know, in the beginning it was hard because I just didn’t have the experience and so I’d get really, really excited or really, really depressed. And I think after you go through that a few times, you’re just your body just physically and emotionally can’t handle it. And then I think the next time you hit a higher kind of like, all right, but like remember last week when you had that big low. And I think over time you just kinda learn to manage it. I thin  keeping things in perspective experience helps with that over time. Keeping your team sort of on that same wavelength because you don’t want them riding the highs and lows, um, when you know you’re the one staying level. It’s like, you know, sharing that experience and perspective with a team. And yes, you want the team to celebrate when great things happen, but you also wanna keep it in perspective and kind of keep a reality check on things. Particularly when you’re building a company out of a recession and sort of you’ve had that like scrappy DNA where it was really, really hard to raise capital. Like everything was really hard in the beginning. And I think because we started at a time where everything was super, super difficult, it kind of gave us the perspective that like even when things were going great, the reality is, is that it may not always go great. Right? And so it’s kind of like just learning how to stay somewhere in the middle.

Ok we’ve got to take a quick break to hear from our sponsors, more with my guest after the break.

Laurie Segall: I wanna go back to you talking about having to lay off folks. This isn’t something you prepare for. As a first time founder, can you tell us the day that you realized you had to lay off folks, the hardest part of it and what you would go back and kinda tell yourself now about it?

Leah Solivan: Yeah, I mean that, that was the lowest low of the entire company out of everything I experienced, um, was, was doing that layoff. 

Laurie Segall: What was the hardest part of it?

Leah Solivan: Um, it’s just failing those people. It felt like a true failure of my team. And you know, the reasons behind it were okay, the product wasn’t performing. We need to reorganize the team and hire more engineers and we needed to cut from marketing and operations and business development. But that’s like, whose fault was it that we overhired in some areas and we under hired in others it was mine. Right? And so it was, it was awful to have to really admit to myself that I had failed in managing the way that the company was scaling. And so, you know, going in, you know, that morning and talking to the team that I couldn’t keep there anymore, it was, it was my worst nightmare come true. And as bad as it was for me, I knew it was a hundred times worse for them.

Laurie Segall: Yeah.

Leah Solivan: Which is like, you know, it’s so, so hard for everyone. I think anything that had to do with people or failing the team or managing the team, it was hard for me. Um, you know, I felt a lot of empathy with people that I’d brought on board who really believed in the company and the mission and believed in me. And then I felt like I was failing them personally. Um, and so that was hard. But you know, with perspective and with looking back, I realized that it is what saved the business, it’s really what made the business thrive in that next phase and afterwards. And as hard as it was, it had to be done if I wanted the company to be successful. And so, you know, I talk to entrepreneurs today that are looking at their runways and their cashflows and they’re looking at the market and they’re having to make these tough decisions and it’s like PTSD all over again. But I tell them, listen, you’re gonna do this and it’s gonna be hard, but you’re gonna look back three years from now when the market improves and you’re gonna realize this is the decision you made to save your company. Um, and so it’s not easy and it’s very emotional. 

Laurie Segall: Do you remember what you said that morning?

Leah Solivan: Yeah, I mean, it wasn’t a huge surprise in that one of the things we really valued at TaskRabbit was transparency. And so people had seen the projections, people saw that our revenue, you know, was not tracking to where our monthly cash burn was. And I remember saying three months before the layoffs, like, “Guys, listen, we’ve got to like, we’ve got to increase revenue, we’ve got to increase demand. Like otherwise our cash burn, it doesn’t match up. It’s not gonna be sustainable.” And guess what, in most companies, like 80% of cash burn, is headcount is people, right? So if you have to decrease burn, it’s like you’ve got to decrease people. And so that was 90 days out then it was like 60 days out and then it was 30 days out. And I remember 30 days out being like, “You guys seriously, like we’ve got to do something big this month and if we don’t do something big this month, like I’m not sure what’s gonna happen.” Sso then that next month came and you know, we went in as a team and I just said, “Listen, we’ve been talking about this now for a quarter and we’re just not running in a sustainable way. And you know, today is the day that we have to reorganize and we have to rethink about how the company is gonna move forward and not everybody can stay.” And so we then kind of broke off with team members and their managers to talk in more detail. And, you know, I think one of the things that I did that was hard but I think was good to do was that after I talked to the team about what was happening and that not everyone was gonna be able to stay, I also gave the option to the remaining team if they wanted to walk, if they wanted to leave that day, no questions asked, they could take the same package that everyone else got. Because I felt like I had chosen where I needed to cut where the company needed to cut, but that doesn’t mean that those people staying had chosen me or had chosen the company.

Laurie Segall: Hm.

Leah Solivan: And I kind of wanted this like mutual moving forward that it’s like, if not everyone can stay, that is terrible. Um, but the people that are here, they actually also wanna be here too. And I think that actually helped with that transition because it, it made this kind of mutual agreement between the company and the people that stayed, that they were gonna be in it and it may not have been easy, um, but they still really believed in the business and they believe that they wanted to be a part of our mission and I think that helped moving forward.

Laurie Segall: How do you know how to lead like that, right? Like it’s like what an interesting decision. Like that little decision, to say like, you know, okay, we’ve got to let people go, but I also want people to choose me. Well that’s a leadership moment too, and that’s you as a leader doing something extra that’s a little bit different. Where do you think that comes from?

Leah Solivan: I got it from an advisor. Honestly, I remember sitting, I was having brunch with Gina Bianchini who runs Mightybell. She’s the founder of Ning, a very successful exit, and she’s been an advisor to me and TaskRabbit for years. And I was meeting with advisors leading up to this. I was like, “Oh my God, like, how do I do this? How do I do this in the best way? Like there’s no perfect way, like how do I do this in the best way?” And I was just getting feedback from as many people as I could. And it was Gina who said, “You know what, and then do this. “And when she said it, I was like, really? Like what if people leave? What if everybody leaves, you know? And she’s like, you gotta know who’s there and who really wants to be there. And it wa- it was hard actually to say that and to share that with the team and to give people that option to say like, you can walk too and get the same package. And we had two or three people walk. 

Laurie Segall: I was gonna say did, did anyone walk, you had, you had two to … wow.

Leah Solivan: We had two to three people walk. 

Laurie Segall: And how did that feel?

Leah Solivan: It, um, well I, I mean, none of it felt good. I mean, it was just-

Laurie Segall: Yeah.

Leah Solivan: But you know what? It was actually a relief in the end because I felt relieved that I knew that the team that did stay actually really wanted to be there.

Laurie Segall: Yeah.

Leah Solivan: And if I hadn’t done that, and if I hadn’t kind of gone through that really hard extra piece, it would have always been a question.

Laurie Segall: Yeah.

Leah Solivan: Um, so I think it was relief in the end.

Laurie Segall: That’s a, such an interesting story. This is such a, this is such a moment to kind of slow down a little bit. And, and one of the things you said when you were talking were taking through like the hard moments of the company. As you mentioned, you ended up in the hospital at one point during the fundraising. So I just feel like the human in me cannot just brush over that. Um, so what happened? You know, wh- when you talk about ending up um in the hospital during a fundraising round. Like, I just also feel like it is really important for people to hear what actually happens behind the scenes with successful companies. And I appreciate the fact that you’ll go there and uh talk about it. And I think that’s important for building successful companies in the future. So, you ended up in the hospital during a fundraising round. Wh- what happened.

Leah Solivan: At the time, I didn’t tell anyone. My Board didn’t know. My current investors didn’t know. The only person that really knew was Stacey, my COO, and a couple of other execs on the team, what was going on. But it was a three million dollar raise. And we had raised like 45 million dollars to date. We were close to profitability. The business was doing well. And we were short this three million to get to profitability. And so I was like, “This is going to be easy. We’ll go out. We’ll talk to some investors. We’ll get three million dollars. And then we’ll be self sustainable.” And it was the hardest raise. I mean, way harder than what I did even in 2008. And there’s a lot of different reasons for that and different dynamics for that. Some of them I understand more now as an investor. But at the time it was just so so stressful. And stressful to the point where I was out with another entrepreneur one Monday afternoon and I was taking a walk. And at the time, he was the CEO of StumbleUpon. And we were walking and you know we were like, “Oh, this is so stressful.” And he was going through a raise and I was going through this raise and were swapping notes. And after the walk, I drove home. And he later tells me that I looked a little green during the walk but he didn’t say anything. And so I drive home and I, my stomach starts to hurt. And I get to the house and at this point I have one child. I have an 18-month-old daughter. So I put her to bed. It’s like seven o’clock. I put her to bed and I sit on the couch and it’s just getting worse and worse and worse to the point where I can’t get off the couch. And so I call an Uber to take me to the emergency room. And I get to the ER. You know, you go through triage. I wait like five or six hours. Sort of long story short, by that point,  it was my colon had gotten infected. And it was this stress induced colitis. And-

Laurie Segall: Wow.

Leah Solivan: The surgeon came in. I was admitted to the hospital. I was put on antibiotics. The surgeon came in the next day and was like, “Have you been under a lot of stress lately?” And I was like, “You have no idea.” And he was like, “Yeah,”-

Laurie Segall: What goes through your head when you’re sitting there and you have like a stress induced, like you’re in a hospital bed and they say, “Have you been under a lot of stress?” Like what do you even think to yourself?

Leah Solivan: This is what I’m thinking. I say out loud, “My company is going to fail because my body has failed.”

Laurie Segall: Wow.

Leah Solivan: And that is exactly what I was thinking. And I was like, “I’m not even going to get this three million dollar raise done.” I was very close with some investors. And I’m like, “Because I’m, now I’m in the hospital. And I’m going to have to have this surgery.” And luckily, I avoided the surgery. I actually stayed in the hospital for five days. They pumped me full of antibiotics. I was on the phone with investors in London at the time, closing this three million dollar deal and got it done. But literally was, that was a Monday. I left the hospital on Friday afternoon and went straight to a pitch meeting. I could barely walk.

Laurie Segall: Oh my God. Were you still like green-ish?

Leah Solivan: I mean, I don’t know. I remember my poor stomach was like so distended. It was awful. Oh, it was awful. But it was like, what are you going to do? I was like, “I have to get this money closed.” And, and it’s like I meet with founders today and they’re like trying to get like a little bit of a bridge raised right now in this Covid time. It’s like the same thing. I’m like, “Oh my God. I feel their pain, Like it’s so stressful.”

Laurie Segall: Yeah.

Leah Solivan: Because you just feel like everything is going to fall apart if this doesn’t happen.

Laurie Segall: Yeah.

Leah Solivan: And your body can only take so much. And so that’s why now, having gone through all of that, I am such a proponent of you know, as a founder, just really taking care of your physical, mental, and emotional health as well. Because I’ve, I’ve been at points where I’ve hit the wall where it hasn’t been sustainable. Um,  it’s just not a good place for anyone to be.

Laurie Segall: Yeah. Was there a moment that you felt… because I, I just kind of put you through the ringer in talking about all the bad moments. And there were lots of good moments. I like that you included our CNN interview on one of them.

Leah Solivan: Yeah.

Laurie Segall: I’ll take that. Um, but was there a moment that you felt, in all of this, like that, that you had made it?

Leah Solivan: Here’s the moments that I look back on the most and think, “That made it all worth it.” And, and we were lucky because at TaskRabbit, we had these little interactions and these little stories every single day of amazing things that would happen on the platform. Just matches that were made or you know interesting stories that happen. And those were the moments that we really held onto as a team and said like, “This makes it all worth it.”  I’ll tell my favorite story real quick which was we were only open in two markets. We were open in Boston and San Francisco. And at the time, there was this woman in San Francisco who posted on TaskRabbit that she had a 20-year-old son living in Boston. She couldn’t fly out there to be with him and unfortunately, he was going through chemotherapy treatment at Mass General Hospital. He’s 20 years old. And so she posted on TaskRabbit to find someone to go to the hospital, to bring him a healthy meal from Whole Foods, and a cozy blanket from her and sit with him every day for a week during his treatments and then call her afterwards to tell her how her son was doing. And the tasker that picked up the job in Boston was actually another mom. And so the bond that these two moms formed across this country was just incredible. And I think, you know with just two markets open, very early days, it was like 2010, I realized what we were building was successful. Like, it didn’t matter the amount of revenue I drove or what sort of acquisition offer I got in the end. But just the, the opportunity to change and improve people’s lives like that, is what kept us going through the whole thing. And we had tons of stories like that on an ongoing basis.

Laurie Segall: And you guys eventually sold to Ikea. Did you feel like you could breathe? What was the feeling? Because you talk about that roller coaster. What was the feeling after the papers were signed?

Leah Solivan: Oh my gosh, it was such a weird day. I remember being on the Board call where we voted to approve the Ikea acquisition. And it was so exciting but at the same time, it was this dramatic moment of my baby, my baby is gone. You know, this thing that I’ve worked on and raised for the last eight, nine, 10 years is, it’s going to be gone. And so I was the last one to vote. We were a Board of I think seven at the time. I was the last one to vote. We all went around very dramatically we were like, “Yes, I approve. Yes, I approve.” And everyone said, “Yes.” And it got to me and I was so choked up in that moment, and of course I approved the deal and it was very exciting. But it was just such a huge transition. I knew it was going to be a life transition and a huge transition for the company, for the business, and for me. At the same time, I was pregnant with my second child. And so I think actually, for me personally, that helped shift me out of the day to day and shift me out of the business because I had now this newborn at home. And so it was like a lot of personal life changes as well that sort of were good for me and helped me move forward maybe in a way that was really healthy. Whereas if I didn’t have those sort of distractions and new joys and things in my life, it probably would’ve been a lot harder.

Laurie Segall: What did you do the day you voted? What was the first thing you did after you, you, gave your approval and you kind of sent your kid off to college in a metaphorical sense?

Leah Solivan: Yes, yeah, well I rem- I was at home. I was at my house. And I think I just remember going downstairs and just playing with my own children, a very normal, very normal day, yeah. But I definitely remember that moment and feeling like, “Whew.” I felt like I was standing like on the edge of a cliff and it was like, “I’ve got to jump. This is, this is it.”

Laurie Segall: And, and you’re now investing. You’re a general partner in an investment fund. You’re looking at companies early on. Why did you decide to become an investor?

Leah Solivan: So you know, for me, I’ve told the story that I founded TaskRabbit because I was really excited about these three emerging technologies, social, location, and mobile. And I’m an engineer. That is my background. And so I love technology. And then I founded the company. I kind of put my head down in this one space, in this one technology and this one business for almost a decade. And when I sold TaskRabbit, I kind of picked my head up and I thought, “Wow, there’s a lot of new emerging technologies that have happened that I haven’t been apart of.” There’s been bitcoin and blockchain, and AR, and all kinds of really interesting technologies that I haven’t had a chance to dig into. So I knew that whatever I did next, I didn’t want to put my head down in one business and one technology again for a long time. That I wanted to find a role that I could really dig into a lot of different areas at once. And so because I had great relationships with investors, over the years, you know a lot of people reached out and kind of introduced me to the idea of investing full time. I spent about a year thinking about it and getting to know different investors before I decided to finally join Fuel. And it’s been a great fit. I get to work with entrepreneurs every day on their businesses. I get to learn new technologies every day. And my partner, Chris Howard, who’s the founder of the firm, is just fantastic. And it’s just the two of us. So it’s been a really really great move for me.

Laurie Segall: Yeah, and,I read something that you, you know you’ve kind of said that founders who care for themselves can better care for their businesses. So, and even in this interview, some of the things you’ve said about the conversations you’ve had with founders who are trying to make sure to get a bridge during this time and all this, you’ve spoken a lot about how they are doing emotionally. I can see that that’s very much in the DNA of how your, of your investment strategy. So what do you tell founders who are in this moment who are looking at the landscape, who are dealing with the normal stress and anxiety of being a founder? Which you know better than most is very stressful. And now have the backdrop of a global pandemic. What advice do you give them?

Leah Solivan: Well, you know my advice is one, you know think about what your business needs to survive over the next 18, 24 plus months. And that usually means what is your cash runway? So we’re advising all of our founders to just make sure they have enough cash in the bank to kind of ride this out. You know, when I started in 2008, it really wasn’t until 18 months later that I was able to get a seed round together. And it, it may take 18 months or longer for really the markets to improve and for investors to really re-engage and put capital back into the markets in the same way they were. And so that’s one thing. I think the second thing is like, once you’ve got that figured out, make sure that you are carving out time and space for yourself, as far as sort of a mental, emotional health and wellness standpoint. And it is so, so hard. I mean we’re all juggling so much. We’ve got kids running around. We’re home schooling. You know, we’re taking care of all kinds of things beyond just our businesses. And now work and life is so integrated because we’re all working from home. So it’s sometimes really hard. And, and sometimes impossible to find the time and space that you need mentally. But one of the things we’re doing as part of Fuel’s portfolio, is we’re holding weekly meditation sessions for our founders, um over Zoom. You know we’re trying to connect founders with resources around healthy eating and healthy sleeping that can help them through this time. I think sometimes it’s just you’re in such a frantic panic mode it’s so easy to stay in that mode. But you can break that cycle, if, even if it’s just like 10 minutes a day to just like sit quietly and make your mind stop. UYou know I wish that I had done more of that when I was running TaskRabbit. And certainly, you know at the end when I tell the story about going into the hospital, like I pushed my body to a place where it couldn’t operate anymore. And that wasn’t good for the business either. If I had just taken some measures to act more sustainably, then I think it would have been a lot easier for me. And you know the business in the end would have reached the same success and the same stories. So, I think it’s just having that perspective that it’s okay to just take a pause for yourself from a, from a mental health standpoint.

Laurie Segall: And if you could go back and you know tell 2008 Leah, building out TaskRabbit anything, as you now having kind of just gone through this huge journey, um, and being on the other side of it, and even now in this crazy moment, um, what would you tell her?

Leah Solivan: I think just recognizing um it’s going to be hard. It’s hard for everyone. But I think actually that was the best time for me to start a business. Now is the best time for a lot of entrepreneurs to be starting their businesses. It’s going to be so, so hard in the beginning but because you’re, you’re innovating something out of a time that’s really chaotic and really hard, it’s going to make you operate differently. It’s going to make you build in a more sustainable way. And I think the opportunity to achieve a bigger vision, sort of this game changing vision where customers will change their behavior along with you, is, you know, it’s like no other time. And so I’m glad I went for it. Um, even though it was just a crazy, crazy journey. And so I encourage you know other people to go for it, too.

Okay, guys – that’s it for this week’s show.

Quick update for you this is one of the last episodes of the season. 

It’s been so much fun bringing you guys stories of founder journeys – the highs and the lows. Some weird stories like that time I had a relationship with a bot, my quarantine diaries, that one time we talked about hacking your brain. Thank you guys for playing ball with me. This has been a blast.

We hope to bring you more First Contact later this summer. Now there’s never been a more important time to explore technology and its impact on us human beings.

My favorite part of doing this show is hearing from you. So don’t be a stranger, let’s stay in touch. The best way to do that is to sign up for our newsletter at dotdotdotmedia.com/newsletter. 

We’re launching it this summer and it’s going to be your best source to stay in the loop on any upcoming episodes that we happen to drop, and we’re also doing these virtual Town Halls so we’ll let you know about those, and we’re working on a ton of projects that we’ll keep you in the loop on. 

So, sign up at dotdotdotmedia.com/newsletter. I promise not to spam you. And reach out to me – tell me what you’re up to and what stories you’re interested in – my number is 917-540-3410. 

Also, a lot of you have been texting me about new initiatives during this crisis, and I know a lot of folks in Silicon Valley working on quite a few of them. So I wanna give a couple shoutouts: 

  • The first is Frontline Foods. Its 500 volunteers have since their start delivered more than 50,000 meals to hospitals in 40 cities.
  • Next is: Code Academy. They’re working on more than 10,000 scholarships to Code Academy Pro for students and teachers affected by COVID-19 school closures.
  • And lastly, and app called Covid Coach, it’s an app designed to help folks stay sane, stay connected, cope with stress, manage anxiety, and navigate parenting and care-taking, during this pandemic.

If you want to learn more or get involved with any of these organizations, go to our show notes.

Follow along on our social media. I’m @LaurieSegall on Twitter and Instagram. And the show is @firstcontactpodcast on Instagram, on Twitter, we’re @firstcontactpod. 

First Contact is a production of Dot Dot Dot Media, executive produced by Laurie Segall and Derek Dodge. This episode was produced and edited by Sabine Jansen and Jack Regan. The original theme music is by Xander Singh.

And as always I’m sending my thoughts to each and every one of you guys and so is our whole First Contact crew. During this time I hope that everybody is staying home, staying healthy, and staying human. 

I’m Laurie Segall, and this is First Contact.

First Contact with Laurie Segall is a production of Dot Dot Dot Media and iHeart Radio.