Advice Line with Leah Solivan of Taskrabbit (September 2024)

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1:58That's where a lot of businesses are with AI. Discover AI that can work seamlessly across your data and applications at ibm.com. The AI built for business, IBM. Hey everyone, it's Guy here. So this week we're bringing you an advice line episode that we really, really loved. It was with Leah Sullivan, the founder of TaskRabbit. And I was super happy to have Leah back on the show because she has a really interesting perspective on the growth of the digital sharing economy, which was really just taking off when she started TaskRabbit back in 2008. Leah was so generous sharing her wisdom and experience, and I hope it can serve as an inspiration for however you're trying to grow as well.

2:42So without further ado, enjoy the show.

2:51Hello and welcome to the advice line on how I built this lab. I'm Guy Raz. This is the place where we help try to solve your business challenges. Each week, I'm joined by a legendary founder, a former guest on the show who will attempt with me to help you. And if you're building something and you need advice, give us a call and you just might be the next guest on the show. Our number is 1-800-433-1298. Send us a one-minute message that tells us about your business and the issues or questions that you'd like help with. You can also send us a voice memo at hibt at id.wondery.com. And make sure to tell us how to reach you.

3:33And also, don't forget to sign up for my newsletter. It's full of insights and ideas from the world's greatest entrepreneurs. You can sign up for free at gyros.com. And we'll put all this info in the podcast description. All right, let's get to it. Joining me this week is Leah Sullivan. She's the founder of TaskRabbit, the online marketplace for services like cleaning, assembling furniture, running errands, and a whole lot more. Leah, welcome back to the show. Thanks for coming on. It's great to be back, Guy. Thanks for having me. Super excited to have you back on the show because today we're going to talk to founders who are all building app-based or web-based products.

4:12or services. And you're one of the OGs in this space. I mean, when ideas like Airbnb and Uber weren't yet fully formed, you actually launched TaskRabbit in 2008. And I mean, this was one of the first brands that became part of what we now call the digital sharing economy. And of course, in 2017, you guys were the company was acquired by IKEA. Exactly. Yeah. I mean, it was early days And it's been awesome to see TaskRabbit and the brand live on. I was just at an Ikea store a couple weeks ago and kind of got a kick out of seeing all the branding around the store as well. Yeah. Leah, before we get to our callers, I suspect a lot of them are working on ideas that might seem a bit ahead of their time.

5:00Like it might be hard to convince people why they might need that product or service. And when you ran into this dilemma, you know, with TaskRabbit at the beginning, how did you work to convince people that this was a service that they would want or need? Like they would actually have somebody come into their home and assemble their furniture or, you know, or go run an errand for them and bring it to their house? Yeah, I mean, it seemed insane at the time to invite a stranger into your house to do things. And even stranger to jump into someone's car, right, for a ride down the street. That was never going to happen in 2008.

5:36But, you know, having experience now as an investor and having talked to hundreds, if not thousands of entrepreneurs, I really think it comes down to three things. Timing, technology, and TAM. the three Ts. And, you know, for me with TaskRabbit, the technology was there, the time was there, and it was an idea that everybody understood immediately. So I felt like there was a market there as well. And it still took a lot of education and trust building. And over time, you know, it really started to scale rather quickly. So you don't always have all three of those things at once. And sometimes it's not the right time or the market, or maybe the technology isn't advanced enough.

6:26And so those are kind of the three things I would think about when you're looking at a new idea. And can you make those three things converge? When do you remember it really starting to gain traction? Because it didn't, it was not an immediate, it wasn't like all of a sudden you flip the switch and people are like, yes. No, it really wasn't. I mean, we were this tiny company in Boston for almost two years before we even opened the San Francisco market. But once we started opening new cities and we saw the people in every single city and every single market start to use the service, give us great reviews, tell their friends, it was a slow build.

7:08But then you kind of start to build momentum. All right. Why don't we take our first caller? Let's do it. Hello, caller number one. Welcome to the advice line. Hi, Guy and Leah. My name is Kate Pitner, and I'm calling from Los Angeles. Welcome. And I am the founder and creator of the Poppy Notes app on the Apple App Store. I design Poppy Notes to be an e-cards and greetings mobile app that will let you easily send text and email greeting cards and instant invites and thinking of your notes from the ease of your phone. Awesome. Well, welcome to the show. Thank you for calling in. Before we get to your question, let me ask you a couple questions.

7:54So this is an app that basically lets you send a card to somebody, just a digital card. Yes. Yes. And it's designed to be very simple. That was the key. Right. And tell me how you, I'm assuming you have a design background. Yes. Yes. I have been a commercial graphic designer for over 20 years and I partnered with companies like Hallmark, Flagology, Joanne Fabrics, Home Depot. But ever since I was a little girl, I always wanted to have my own greeting card line. And I used to sit in my room and draw and my poor family had to take all of my cards for all of those years. Many, many cards. and when 2020 hit and the pandemic hit and we all couldn't communicate like we were accustomed to and being able to just stay connected to people I started making greeting cards that I could text and email to family and friends and people really loved them and they kept going where do you get these I want to text and email these too and that kind of started the whole process And that took a couple years and a whole lot of time and stress and development.

9:10And I was able to launch two weeks before Christmas in 2022 on the App Store. And basically the app makes it easy to just like write a message to somebody on a card, a designed card, and you could just text it to them or you turn it into like a text or an email or what? Yeah. So you go on the app and you select, I have them categorized by different themes. So holidays or birthdays or thank yous. You pick your card you want, you scroll through the options, tap on it, type your message. I've added some fun features where you can customize the font and color and the size and make it really personal.

9:54And then you just click send and you can choose to text it, to email it. You can social share. It kind of has a lot of fun options. Yeah. And did you have to make a sizable investment to develop this to get people to help you build it? Or did you build it yourself? Yeah. Luckily, I could do all the designing of the artwork, but I'm not a coder, and that was my first hurdle. I asked a number of friends, got some mentoring on what on earth this coding thing is and how to even do it. It's a whole different language. And I did find I had a few different developers. I have a great development team, and that's how I kind of started.

10:39I had to teach myself how to do the basics, like the UI UX design. I did that myself, and then we built from there. Got it. And the app is for like a freemium model, so it's like free, but then you pay for some stuff? Yeah. So it's free to download, and I have a welcome pack of cards that are free for everyone to use and start using right away. I also have another category I just added called Spotlight, where I'm partnering with nonprofits to create their own line of poppy notes cards, like breast cancer awareness. And then to receive full access to the entire library, it's a low monthly subscription, US$1.99 a month.

11:24Got it. Okay. And before we get to Leah, tell me what question you brought for us today. My problem is, or my biggest challenge is finding and reaching my audience, particularly as a tech product. And it's easy to get lost on the App Store. It's easy to get lost on Instagram. I'm trying to reach my audience. I know that was something you definitely dealt with, Leah. Yeah. All right. Leah, before we get to the question, to Kate's question, do you have questions for Kate and for what she's building? Yeah, well, Kate, first off, super impressive that you've been able to build this much, you know, basically on your own and all of the design work that you've done.

12:06I mean, it's really, really incredible. And so, yeah, I mean, I think I understand the question just reaching that audience. And I think, you know, my main, I guess, question and feedback, and I'd love to hear how you think about this, is I know that there's a lot of categories and a lot of designs available right now on Poppy Notes, which is amazing. The App Store is super, super crowded for lifestyle apps. I mean, it's just like crazy how many apps are in that category. And so it takes a lot to stand out. It takes a lot to rise above the noise. So I'm wondering how can we figure out what the wedge is that you can create that differentiates you and what you're offering people?

12:53And maybe it starts with how people are using it already, or maybe it's something new and different that, you know, we haven't tried yet. So what are your thoughts there? That's a very good question. So in the category idea, you're talking about different themes and different types of cards. So maybe I want to market a real specific theme to a specific audience so that I can hook that audience. Is that kind of what you're asking? That's kind of what I'm thinking. And I just wonder, like, if you kind of look at the competitive landscape of what's out there today, like, I think Paperless Post, I think Evite, I think these big apps, you know, that, you know, have kind of built up their base over many, many years, even decades.

13:34And they're kind of have this generalist approach where they're available across all these categories. I wonder if, is there a category that maybe they're missing or maybe is an opportunity for you to focus on? Like, okay, I have babies on the mind. We're getting ready to have our fourth child. I wonder, like, is there something around like gender reveal or something that is like a little bit more, you know, unique, different where you start to build that wedge, you start to build an experience through the app, through your designs, that's differentiated. No, that's really good. I actually am thinking too about babies and the idea of, I know when I was in that stage of life too, it's just all encompassing.

14:22But I do know a lot of my really popular cards are school age children cards, mom support cards. Those kind of things might be really perfect, what you're saying. And even I would think through the full stack of how to reach your audience, are there influencers? Are there, you know, mommy bloggers, mommy influencers? I mean, that's a huge category. Yeah. That, you know, paperless post is not partnering with them. Like you could be the one partnering with them, right? And it's differentiated. It's unique. It's custom. I mean, there is so much noise. But I think if you can find the right ambassadors, the right influencers that align with your brand and values and voice, it can be really, really powerful.

15:08I would, you know, just looking at the app on the App Store as well, it's just it's going to get lost in the App Store. Like, I don't I don't know how much time I would, you know, spend trying to optimize that. One thing you could do there, though, is if you start to build a wedge in a category that is standing out, maybe you can try to get on some lists in the App Store that are, you know, like top five or top 10, like baby shower, you know, not just the lifestyle brand, but very specific. Because it's just so hard to be in that big group. I think you really got to hone in on something that's really differentiated.

15:51To me, a lot of these different apps are, I mean, we've had Canva on the show and some of these other companies on the show and brands on the show, and they're awesome. They offer great products. Not always super easy for somebody like me to figure out quickly because I'm sort of useless. And so it seems like this is really, this is like super plug and play. Yes. I can teach my 82-year-old dad how to use this in like five minutes. That's the goal. Yeah. And that to me seems like an opportunity to sort of maybe senior citizens too. I talk to my dad every day and my mom and they want to talk to their grandkids.

16:32And maybe this is something that there's a way, especially on the blog, because I noticed you've got a blog, which I think is great because that's another way to reach people when they're doing searches. to maybe think about ways to direct some of the message to seniors as well. You know, hey, is this a way to send a message to your grandkids with just a funny photo and you're a funny message? That's a great idea. Actually, I mock up a lot of my cards in my marketing with that in mind. So I love that you tapped right in. That's, I need to do a little bit more of that, I think. Yeah. Yeah. One other quick thought, which is creating virality, right?

17:13And it's not so easy, but if you've heard the show before, you'll hear this theme pop up again and again, which is the number 1 ,000. And this is a highly researched number, which is the argument that to start something to create momentum for a brand or product, you need 1 ,000 people who adopt it. And those 1 ,000 people become the force multipliers, right? And so is there a way, and I don't know the exact answer, and I'm sure you've thought about this, but when you send this as a text, when you send it as an email, for there to be some kind of link that essentially says, want to make your own?

17:52I love that. and you click it, you know, I mean, this is the story of Slack or Dropbox or, you know, these other viral products, which is in order to use Dropbox, you got to set up a Dropbox. So it invites you to do it. And I wonder whether it's like, hey, this, do you like this? You know, click here to make your own poppy notes. Oh, that's a good idea. And then you get every, every member of your family, distant family, relatives you haven't talked to for 25 years, people you thought you didn't have to see ever again Thanksgiving, get all of them to use poppy notes, everybody you know. Because I'm sure if you think about it, you probably have hundreds of people, distant people all over, loose connections that you can just send this out to, shamelessly, and say, hey, try this and send it on to other people and tell me what you think.

18:45Absolutely. And now you have two more fans right here. Thank you so much. That means so much. Just about to send a poppy note right now to Leah. Yes, absolutely. I love it. Thank you very, very much, both of you. All right. Kate Pintner, Poppy Notes. Good luck. Congrats. Thank you so much. Take care. All right. Do you know, you probably had this experience, Leah, which is it's your birthday and your kids are trying to figure out what to do for you. And you say to them, I just want you to make me a card. Absolutely. That's all I want. Yes. I have all those cards for my kids. Yes. Yes. Now I'm going to say make me a poppy note.

19:23Make me a poppy note. You know, the stick figures, it's like there's something really special about that. There is. Yeah. So I'm thinking about Kate as a little girl always wanting to have a greeting card company. Yes. It's the dream. I love that. It's a dream. I love that. It's a dream. All right. We're going to take a quick break. But when we come back, another caller, another question, and another round of advice. I'm Guy Raz. Stick around. You're listening to The Advice Line on How I Built This.

19:55If you've been listening to the show these last couple of episodes, you've probably heard me mention the Airbnb original experience that I'm hosting. And I'm so excited to have a chance to connect with listeners in a completely new way. It's called the Reinvention Lab, and it's designed to help you think about how to unlock your next big move in your career or even in your life. I'll help you discover your own story in ways I do on this show with my guests. And attendees will get a chance to take a deeper dive with me on so many lessons I've learned from this show. Lessons that have transformed how I work and think about the future.

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22:50Welcome back to the device line on how I built this lab. I'm Guy Raz, and my guest today is TaskRabbit founder Leah Sullivan. So, Leah, let's bring in our next caller. Hello. Welcome to the advice line. Hello, Leah and Guy. My name's Sean Sarekli, and I'm from Sydney, Australia, and I'm delighted to be here talking to you today. Welcome to the show. Tell us a little bit about the name of your product and what it does. Yeah. So, along with my wife, I'm the co-founder of My Love Your Love, which is a couples coaching app, which is designed to take couples on a journey to unlock all the amazing benefits of long-term relationships.

23:27Wow. I'm sure there's a lot to ask you about because you are, I imagine you and your partner are doing a couples therapy thing. Then there's a lot to unpack here. Tell me about how, so how does it work? It's an app you download and presumably designed for people who are having problems or what? Absolutely. Actually, it's designed for anybody in a relationship. and one of the main reasons to create this app is because people come to therapy way too late and we know the longer you've had problems in your relationship the more likely it is that you're going to break up and that interventions aren't going to be as helpful so this app is for anybody if you do have problems yes it is going to help you that's really designed to make your relationship robust and deepen your bonds over the lifetime and and tell me a little bit about you and your wife.

24:25I'm imagining both of you guys are therapists. We are indeed. So we're both clinical psychologists and we're both couples therapists as well. So it means that I can tell you we have a great relationship, but we've had plenty of conflict. And part of the app is actually wanting to take all of our clinical knowledge, take all the research and distill it into an app. Coming back to that question before, how does it work? Well, both parties have to download the app. It's fully synchronized. You go on a journey together through a map, through many different interventions and strategies. And as you move through that journey, two things happen.

25:08One is you unlock your toolbox so that when problems arise in real life, you can go straight to your toolbox and access them in real time. And on the other side, you actually build out your relationship profile. So you get to learn about your own vulnerabilities, your vulnerabilities of your partner, your conflict styles, your values, and your desires. And there's more features to the app than that actually also. Huh. Wow. And so how did this idea come about? I mean, imagine you guys were and are busy doing in real life couples therapy in Sydney. So how did you guys come up with the idea of like, let's make an app?

25:51And was it like, because presumably you wanted to reach more people because it's expensive to go to couples therapy and you want a more affordable option? Like what? Tell me about it. Absolutely, all of those things. I think couples therapy is universally expensive and separation and divorce is astronomically expensive. So we wanted to create a product that anybody can get access to. And look, I've been a psychologist for 23 years now, and I've seen the power of a positive relationship. and sadly I've seen how devastating you know conflictual and toxic relationships can be not just on the people in the relationship but those around them as well and there's a lot of focus on curing disorders but there's not a lot of focus on preventing and promoting good mental health so we thought how can we make the biggest impact and also there's not really a good guide or handbook about how to have a relationship.

26:51So we thought we need to get this out there to prevent the problems before they happen. So basically, based on your experience, right? And this seems intuitive, but you know, so many things that seem so plainly obvious that we just don't do or ignore. But essentially, what you're saying is, if you can sort of focus on conflict resolution quickly, then that kind of opens up the possibility of strengthening a relationship and preventing it from spiraling. Absolutely. So relationships and behaviors run in cycles and feedback loops. And the longer conflict goes on for, the more damage you do. But more than that, we also know that, you know, positive behaviors are protective of the relationship.

27:41So for example, if you have a habit of being loving or kind towards your partner, you're going to be more uncomfortable with conflict and want to go back to the status quo. Now, a lot of people, great relationships have that habit and a lot of relationships don't. So the app actually helps you identify what cycles do you have which are good, what are the patterns and cycles and vulnerabilities that you have which you probably picked up from your family of origin, from past relationships. How do we find the antidote to those as a couple? And then we put in the positive behaviors as well. And how much, what's the cost?

28:19Okay, so it's$108 per year if you want to get the yearly version or$17.98 per month. So on the higher end of apps, but presumably a lot cheaper than going to a therapist. Well, absolutely. It's a lot cheaper than just one couple's therapy session. And Sean, what's the question you brought for us today? Okay. So my question is about user acquisition. So we do have a social media campaign going and we do have a monthly newsletter, which has about 1100 subscribers to it. But user acquisition has been slow going. And I guess one thing that we didn't think a lot about, which is the whole point of the app actually, is that you need two people committed to take the My Love, Your Love journey.