Leah Solivan Founder of Task Rabbit General Partner Precedent.vc

You wanted the best. You've got the best podcast. The hottest hot podcast in the world. The Chris Boss Show. The preeminent podcast with guests so smart you may experience serious brain bleed. The CEOs, authors, thought leaders, visionaries, and motivators. Get ready. Strap yourself in. Keep your hands, arms, and legs inside the vehicle at all times cuz you're about to go on a monster education roller coaster with your brain. Now, here's your host, Chris Voss. Folks, Vos here from the Chris Vosshow. com. — There you go, ladies and gentlemen. The iron ladies that makes official. Welcome to 16 years and nearly 3,000 episodes of the Chris Vos show. one of the oldest, actually the oldest, still broadcasting on a daily basis podcast, uh, out of a handful that are still left after all these years. Uh, anyway guys, support the pirate ship if you will. Go to goodreads. comrisfos, linkedin. com, for Chrisos, YouTube. com, 4chessfos, and all those crazy places on the internet you can find us. Today, we have an amazing young lady on the show. We're going to be talking about her journey through a lot of different things that she founded in the gig economy and some of the different journeys she's on and what she's up to today. Leah Sullivan is the founder of TAS Rabbit who pioneered the gig economy and is now disrupting venture capital with the same bold vision that made her one of Fast Company's 100 most creative people in business. She's closing her first fund precedent VC laser focused on AI powered marketplaces. I've heard those things are hot right now that AI within six months she did it and while simultaneously writing a book hosting the pres. not the hosting the breaking president podcast serving on three major boards PetMeds San Francisco Ballet YO Pacific US and hosting the unprecedented lunch series intimate off therecord gatherings where founders investors scientists and civic leaders tackle the hardest problems in regulated industries like healthcare. Welcome to the show Leah. How are you? — Thanks so much for having me on. I'm doing great. How are you? — Thanks for coming. I'm doing awesome. give us dotcoms or do whatevers on how people can find out more about you on the interwebs. — Yeah, the easiest way is just to go to leasalivan. com. That's where I have my book, my podcast, and my fund. — There you go. So, let's get into it. What do we want to talk about first of what you're doing there at Precedent? The podcast or the uh the VC work or I'll let you lead off with that. Yeah, you know, it's interesting, Chris, because the fund really evolved out of the podcast. So, let's start with the podcast. Um, I was on maternity leave with my fourth child — and I wanted a creative project. And so, I had the idea to start a podcast called Breaking Precedent where I interview leaders across industries that are shifting society in some way. And not just business and tech people, but artists and activists and politicians as well. And I had so much fun, as you know, interviewing these thought leaders and hearing their inspiring stories that I the podcast actually kind of morphed into a book deal. So, I do have a book coming out next summer. — The book uh is being titled now, but I think it will also be called Breaking Precedent, — and it becomes kind of this rebel toolkit for navigating work identity, leadership, and life. Mhm. — And it'll include some stories from Taskrabbit as well as other people's stories from the podcast as well. But after I kind of got the book in place, I thought, you know what, this is a great time to start a fund. And so I launched the fund Precedent VC. We're investing at the earliest stages of technology companies, and we're really looking for this next generation of founders that are category defining and precedent setting and creating new experiences for consumers. — Wow. There you go. There's a lot of that coming up on board with AI. It just seems like it's the hottest thing right now. — I mean, there's so much happening like it's just the consumer behavior, consumer mindset is shifting. Um, you know, there's been certain inflection points with technology where everything has changed and AI is certainly one of those inflection points. Ah, now if anyone's listening out there that's interested in investing in funds, uh, is your fund o only open to accredited investors or certain types of investors? — It is. You have to be an accredited investor um to join the LP base um, but you know, we're doing a next close in the next four to six weeks or so. So, it's an exciting time. Well, congratulations. Hey, we need to get a fund for the Chris Fos Show podcast, man. Let's get that on the We'll have to cooker. Uh, I need a fund just for me, just for

my spending. Uh, can we do that? Is that legal? Anyway, uh, maybe I'll run for president and make it legal. Uh, so, uh, you you've done this precedent thing. Uh, how long when did you start the podcast and what was your journey kind of like? I I'm kind of interested. You know, we started ours so many years ago, I can't feel my legs. Uh, or my brain for that matter, but uh, what was it like starting and how long you've been doing it? Uh, and all that good stuff. Yeah, I mean I started the podcast almost two years ago now and the fund within the last six months or so, but prior to that um I had my own company. So I founded a company called TaskRabbit — back in 2008. I was living in Boston at the time and Taskrabbit is one of those apps where you can go and you can outsource small jobs, tasks, and errands to other people in your neighborhood, in your community. — So I ran that company for about a decade as CEO raised $50 million in venture capital funding. And then in 2017, I sold that company to IKEA, the global furniture retailer, because, you know, no one likes to assemble IKEA furniture by themselves. — So, it was a perfect partnership. — Yeah. Not even IKEA, evidently, because they just don't even bother. — Yeah. That's why they bought Task Rabbit. They were like, "We need someone to do this for us. " So um so since 2017 I've moved over to the investor side. I've been investing early companies like I was early into a company called Nanit which is a baby monitor computer vision baby monitor company. — Um you know a company called Picasso which is in the real estate property tech space. Um child care marketplace called upwards. Um so all kinds of different companies. I have about 150 companies across three funds. uh that I've invested in over the last 10 years. — Wow. So, you just been having fun there. And you're based in Silicon Valley now or Boston or — I am. I'm based outside of Palo Alto. — There you go. Boston, Massachusetts. Boston. I didn't Did I even do that? Good. — That's where I grew up. No, it's more like um Let me see if I can do it. Boston. I don't know. I like I'm half Puerto Rican, so I've got like a Spanish accent and I don't know. Yeah, — Puerto Rican a PR. Boston PR. I don't have any jokes for that, but uh — yeah, we had the governor on of uh Massachusetts on a couple years ago. — Really nice guy and seemed to play down the middle. At least that's how he presented himself. I don't live in — in Massachusetts, but really nice guy. I gave him my Ted Kennedy impression and — he gave me a pity laugh pretty much. Anyway, uh so uh with the president and your podcast, what future do you see this coming out to be? What's what do you hope to achieve on both those fronts? And um uh you know, I mean, are we on the precipice of a new AI revolutionary age? Maybe. — Well, you know, I I feel like every day in the headlines, the word unprecedented is being used today, right? I mean, it's like unprecedented times, unprecedented technology, you know, whatever is happening, everything right now is unprecedented. And so, you know, that was kind of the point of starting the fund and the podcast. And it's like, let's explore, let's explore what is happening, what innovations are happening, and how precedents are being broken and reset and, you know, entire pieces of our society are being changed in real time. I mean, we live in a really exciting time. Um, you know, if you look at it that way. So um you know I think the other big time where technology was at this inflection point was when I started Task Rabbit — and so that was in 2008. — Um the iPhone had just come out the prior year. — Uh Facebook was just breaking out of the college scene and becoming more mainstream and all of a sudden you had location-based technology in these phones all the time. And so at the time in 2008, my background is engineering. So I thought, wow, this is a great opportunity to kind of mash up social, location, and mobile, connect real people in the real world to get real things done. And, you know, obviously ran that company for a decade. So I feel like we're at this new inflection point where, you know, we know that over 60% of Americans in the last six months have used some form of AI. We know that millennials specifically millennial parents over 85% of them are using AI on a daily basis. — So we are seeing habit formation happening. We are seeing the consumer mindset changing in real time. And you know I think that um a lot of the most iconic companies are going to be started in the next 12 to 18 months. Huh? We should close this thing down and restart just so we can catch the wave. Uh, — maybe an AI native version of the

Chris Vos show. — The Chris Vos AI show. Hi, I'm Chris Voss. Welcome to the show. Yeah, there. I think it's like that now from some of the comments I get on YouTube. Anyway, — yeah, that that's probably true. The one thing I always get is that they always viscerate me that I either talk too much or I don't talk enough — and I can't win. Like I can have one of those uh professor speakers come on and they just go on a speaker thing and I just sit here and go like Carson and just go, "Okay, well let me know when you're done. you. " And uh and so I barely talk through the whole thing because they just they think uh there it's a TED talk. And uh um and I'll still get like you would you let the guy freaking talk? And it's like, and the other thing is too is, as you may know from doing a podcast, if I'm talking more than the guest, I'm filling because the guest is killing me. Right. — Uh they're giving me dead radio error. You're like, so tell us about your book. Uh it's got a binder and a cover. — Right. — You're like, "Dude, we got like half an hour here, man. You're killing me. — I'm gonna have to carry this show. " So, anytime I'm telling my stories, you know, it's a bad show. Anyway, um I think the audience has figured that out. So the uh let me ask you this. In 2008 — uh not only was it the iPhone, but there was a precipice of so many people getting laid off. — Yeah. — Especially in like tech and different things and fields. I mean it was a huge crash in 2008. I lost an empire companies. Uh it was fun. It was a lot of fun. — Great time. But out of that came this great like you know social media and Twitter, Facebook and you know all these different things your company and uh and so that unemployment spurred the brilliance of ideas I think um and maybe we're up for that again. We have these huge you know the tech layoffs seem to be getting just beaten with the AI. — So there's a lot of great people out there that can code that know how to build these and design these sort of uh online formats. And so I think it's going to lead uh to that new thing. Do you think that's maybe a factor that's going to drive this uh all those unemployments and stuff? — Yeah, I think that's a excellent point. Um in 2008 when all this was happening, I had just left a very cushy job at IBM. My parents thought I was insane for quitting — and starting a company from nothing by myself. Um, it seemed really, really crazy at the time. Uh, but it turned out, as you pointed out, the best time to start a company like Task Rabbit because so many people were being laid off and people needed new ways of making money. They needed flexible work. — I was like I was actually shocked when I first started the company and I put that first ad out on Craigslist asking for taskers. We call them taskers. And I was flooded with applications and they were, — you know, lawyers, teachers, physicians that had been laid off from full-time work. I was like, "Oh my gosh, like these are highly educated people that have been in the workforce a long time and they want to come be task rabbits. Okay, great. " And so we were really able to use that as a signal at the time to build out a marketplace for them to earn money. So it was an inflection point for that reason. And I think now with AI, you're right. I mean, the same sort of thing is happening. Tech workers are being laid off in droves. That certainly, I think, opens up opportunity for people to innovate. And then I think the other thing that's happening is because AI is so powerful, it's democratizing access to coding. you know, you don't have to be a software engineer who studied at, you know, Stanford or Carnegie Melon or wherever, right, to build out your website or your idea. It's like you can now leverage AI to do a lot of that coding. And so it gives access to more people actually to build and to innovate and to um share their ideas. — Yeah, it's going to be I think a huge thing. And you're right. I mean, I'm not a coder guy. I I'm just not built that way. I'm a business visionary. I love big ideas. Uh I'm not an accountant. Well, I can play an accountant on TV. Uh but uh the uh um when I need to cook some books or something, I don't know. Uh but you know that entrepreneurial thing goes, maybe you don't. I don't know. I don't want to throw you under my bus. Uh the when the IRS calls me and goes, "What? What did you say on the podcast? " Anyway, like they care. Uh so uh you know but being a CEO I just never un I I just can't apply to the mindset of coding. I can do like some basic WordPress HTML that's about it. Like you don't want me anywhere near your code. — And so uh but with AI and Claude and

stuff. — Yeah. — And you know I have friends uh my one friend he was on the original Apple team um that built the iPhone. Uh my other friend uh did a lot of VC work with Amazon for their cloud and now he has his own VC stuff that he does and both of them were like really brilliant coders and just they just brag all over Facebook. They're like this is the most amazing thing ever. this is like almost better core code than humans. — And uh — yeah, — and so I've tried some of it to build a membership website that I needed to do — and it's just making me the coding — and I'm just sitting there. — You're doing it. It's happening. — I'm a dummy. I'm an idiot. Yeah. I I really wish I could learn to code. I just Oh, maybe I'll learn a lot. — You don't need to now. learn. You can just figure Yeah. Just work with AI. It's pretty amazing. grab it for coding. You know, the other thing is too, a lot of those companies like yours that came out of that era, — I forget what they called it, but there was a thing that they talked about one time where a lot of these companies just basically came from Craig's company, Craigslist. — Oh, Craigslist. Yeah. Yeah. I mean, that's where I found the first 30 taskers for Task Rabbit. Yes. Absolutely. Yeah. And here's a fun fact for you. So, um, after I got going, I was good friends with the guys that started Lyft. So, they're the competitor, you know, to Uber. — Um, but before they were competing with Uber, they were doing like more like ride sharing, not on demand taxi services. — But I was chatting with them one day. They came by the Task Rabbit office and they're like, "Oh, we really feel like we should compete with Uber and we feel like we have, you know, the site built, but we don't have the drivers. How do we get the drivers? — Yeah. — And I actually said, "Well, you know what? We background check everyone at Task Rabbit. How about I give you a hundred Taskers to start the Lyft service? " — Oh. — And so I printed out a spreadsheet for them with names and emails that I'd all been background checked and I said, "Here you go. You can reach out to them. " And that's how Lyft got going. — Wow. I did not know that story. — Yeah. I actually haven't told that story very often. Um, so it's breaking news here on the Chris Boss show. — Breaking news on the Chris Bos show. Did you put it in your book? — I did put it in the book. It's in the book. You got to if you read the book, you'll hear lots of other stories I have never told, — but the book's not out yet. So, we got it first. So, thank you. Thank you very much. Uh, my friend Robert Scobble was uh at uh who's the France guy? Uh used to hold that France uh convention every year before he got divorced. — LeB you know who I'm talking about. Oh yeah, I went Yeah. Loique. I um Yes, — I went there every year. Spoke at that conference. Yeah, it was a great conference. Yeah, — my friend Robert Scoble was in a shared taxi with Oh, yeah. — uh with Marissa Mayor sitting on his lap in the They're all crammed taxi trying to leave, — right? Yeah. That's where they launched Uber, I think, at Lette in Paris. Yeah. — And on the other side of the taxi were the guys the CEOs of Uber and they were launching it. And so when he came back, he's like, "You're never going to believe this story. " You know, cuz we're best friends. And he goes, "Uh," he goes, "You're never going to believe the story. " I had Muslim Mayor sitting on my lap in a taxi and I've got the guys, these guys from this company called Uber. And he told me about it. I was like, "I don't know to work out. " — Yeah. I was at that afterparty in Paris. I stayed up all night. I was there. Yeah. Good times. — Yeah. The uh And now you look at it and you're just like, "Wow. " of course started from a you know pitching on something like that. So there you go. Um the uh so you've what's some of the most important things maybe learned maybe you touch on this in your book uh over your career of being a VC and building companies being a leader etc maybe. Yeah, I mean I think what really drove me to write the book um which is called breaking precedent is empowering people and showing people that you know they don't have to follow the rules that there are these invisible rules that govern us all the time and some most of them are just made up by who? I don't know. We don't know like multi-generations, our grandparents, you know, that came before us. And so, you know, thinking through um I talk a lot about in the book having this entrepreneurial mindset — um this concept of instead of deja vu where you see something for the first time and you're like, "Oh, that feels really familiar. Have I seen that before? " — I talk about the opposite feeling, which is vuja day. and you've seen something a thousand times — and you can look at it differently. — And that's kind of like the mindset you have to be in as an entrepreneur because ideas are all around us. Invisible rules And it really takes

are all around us. And it really takes kind of questioning and thinking through why does it really have to be this way? You know, have you ever said like um you know, I something needs to change. How often do we say that something needs to change? Does it really have to be this way? And it's like the book is all about like No, it doesn't. And you can be the one that makes the change. — Yeah. It's uh you know, you like Uber, you know, who would have thought, you know, the regulations or the rules were, you know, you have to have one of those coins, those taxi coins. — Oh, right. The medallions. — The medallions. They're worth like millions or they used to be. — Uh — you talk about a corrupt system. — Oh, yeah. I mean, I lived in Vegas when they were trying to get Uber going. Still do, but I was down there at the time and they uh you know, the taxi companies, oh my god, the lobbying and the fighting they were doing to block Lift and Uber and — and you know, they were like, you have to own the medallion and just like you said, you know, you have to own the medallion evidently. — Do you really have to? Who said you do? — And so breaking these rules and breaking the you know I mean even like uh I think one of the most famous messups was uh someone an old CEO or someone from IBM said h there's no room for personal computers in people's home. Maybe five or six people maybe. — That's right. Yeah. And isn't that what gave Apple the power to move ahead? Yeah. Exactly. — Break the rules. Break all the things. and uh you know that that's the great thing about being an entrepreneur is you you experience something or you look at something and you can go that sucks. I can probably do it better. and you come up with a vision and you tinker and you toy and — you tweak and uh if you're lucky, you know, you build something and people catch wind of it and — and it uh you know helps them and you're paid usually in direct proportion to that as uh I used to hear I forget the radio guy used to say that but uh yeah and so what a great thing as you go through your journey um what was it like learning you know your style of leadership and how to be a leader successfully? M yeah I mean that's something they don't teach you in school and I was an engineer so they certainly didn't teach me anything like that in school. — Um I graduated with a math computer science degree. — So you know I spent the first eight years of my career actually at IBM. You mentioned IBM. I was a programmer there for a long time and before I had the idea for my company Task Rabbit. So there was a huge learning curve, huge learning curve on how to build, scale a company, hire a team. I had never hired anyone. I had never managed anyone. I had certainly never fired anyone. And you know, these are hard lessons to learn. And so I credit, you know, surrounding myself with mentors, role models that I could look up to and see how they did it. One of those people at the time when I was just getting started is a man named Scott Griffith who at the time was the CEO of Zipcar in the Boston area — and um Scott and I met through a mutual friend. We really hit it off. He kind of took me under his wing and you know let me sit in the Zipar office for free for the first year that we existed. I got to watch him be a CEO, watch him, you know, inspire a team and bring on new people and build new products and deal with challenges and issues that would arise as well. And so it was really beneficial for me to be able to have, you know, that experience and that role model that I could look up to. — Yeah, that's really good. And the nice thing about I think I may assume having VCs at your disposal is you can pick their brains and maybe get help from them on different things like uh leadership and things like that. I don't know. Do they offer that or do they just go — Yeah, absolutely. It kind of depends, right? It's like I'm a VC but I'm also a founder operator. So I've I have lived experience to share. I have a lot of empathy for founders I invest in. So I think that is helpful. Yeah. — Yeah. It's uh it's something else. It's hard when you first uh do leadership because I mean the first time you got to fire somebody, especially if they didn't earn it, you know, maybe layoffs or something or Yeah. maybe, you know, rapping, whatever. It's really hard. Now, if they did, if they did something wrong, I usually don't have any problem with it. I kind of enjoy it. It was still hard for me at first. — Was it? — I remember having to let go my first hire because it was not working out and I it just it was terrible. I was so nervous. I like I had to be coached on how to do it well. I mean, it's just awful. But, you know, you do it a few times and you get used to it. — Yeah, I mean, I always enjoyed firing people that had it come in or deserved it. You know, they stole from us or did something. But, you know, the hardest part about most of it was make sure that you loop the back of their belt as you hold their collar and throw them through the second story window. That's the main You got to get that belt. If you don't get that belt loop, um, you're going to they could flop and you want them to hit the pavement the right way. Oh my god.

— That's the important thing. I don't know. That's what I You do that all the time, right? No. Anyway, uh so uh what else do we want to plug on the show? We got your book coming out. Uh we have a date for that anticipated date. — And it'll come out next summer. I don't have a date quite yet. Um but it's exciting. We're starting to work on the book cover. What is it going to look like? Um you know, stories that I've told in it are stories that I've never shared before, like this lift story. I have a few others up my sleeve, too. — Um so, yeah, it's pretty exciting. And I feel like now that gosh, what has it been? It's been almost 10 years since I sold the company, — Uhhuh. — I'm able to kind of speak more freely about the truth, right, of what happened or different scenarios that happened. Um, — so there's some pretty interesting, I think, details that have never been shared before. — Yeah. You know, uh, since, uh, the builder company, what was the name of the company that bought it again? — Taskcraft. Oh, uh, IKEA. — IKEA. IKEA actually let you hire people on Task Rabbit to eat the those horseladen meatballs. — Oh my god, I love those meatballs. I'm obsessed with the meatballs. — Do you remember about how they had horse in them over in Europe or something like that? — I did not know they had horse meat in them. But I will tell you — years ago, — I can eat so many of those meatball meatballs. It's crazy. I really can. I mean, I I've like legitimately made myself sick once eating so many meatballs. — Maybe they had horse meat in them. I don't know. — I don't know. I think it was a Europe thing and an accident or something, but they found it or I don't know. Maybe it's a delicacy over in Europe. — They're delicious. Those meatballs are delicious. — Anyone can trust those imperials. I know whatever. Uh so what more uh do we want to plug while we have you on the show before we let you go? — Yeah. Well, I think um you know the last thing is the podcast really and I'm always looking for stories from precedent breakers, people that are shifting their industry, doing things differently. And so, you know, if you have a story you want to share, I'd love to hear it. And, you know, you can go to my website, breakingprecedent. com, and learn about more about the podcast there. — There you go. Get on there, tell your story. Podcasts are such a great way to share data and information and stuff. I love it. And I learned so much, you know, kind of what we were talking about earlier where you can have that paradigm shift of looking at things in a different angle and sometimes that really unlocks some of the potential of that. You know, that's the great thing I have with guests like yourself on the show. Uh they'll bring different paradigms. You know, I've talked about leadership five million times, written a book about it, you know, all that stuff, right? Adnauseium. Uh but people will come on and they'll give me different spins or different angles. They'll remind me of something I forgot. And so I just love it. It's just so wonderful. And I find people really interesting, too. They, you know, the choices they made through lives, what they decide to do with their lives. I find it really interesting. — Yep. I love it. I love hearing people's stories. I'm inspired every day I get to hear someone's story. And then I think what's really cool too is kind of creating this framework and this toolkit for other people that are trying to break through something are doing things differently. And it's like we can all learn from each other. — Yeah, That's the why we share our stories, books and our podcasts and everything that we do. Well, it's been wonderful to have you on. Thank you very much for coming on. give people a final pitch out to check out your podcast, your books, all your works there, etc. — Yeah, you can reach me at leasullivan. com, breakingprecedent. com. And if you have a company that you're building um and it's early stage tech, I would love to hear about it as well. You can email me at dealsprecented. vc. Well, thank you very much for coming on. We really appreciate it, Leah. — Thanks for having me. It was really fun. — Thank you. And thanks Simon for tuning in. Go to goodreads. comrisfos, linkedin. comrisfos, youtube. com/chrisfos, and all the wonderful places around the internet. Be good to each other. Stay safe. We'll see you guys next time. You've been listening to the most amazing intelligent podcast ever made to improve your brain and your life. Warning, consuming too much of the Chris Show podcast can lead to people thinking you're smarter, younger, and irresistible sexy. Consume in regularly moderated amounts. Consult the doctor for any resulting brain bleed.