Advice Line with Leah Solivan of Taskrabbit (September 2024)

Summary

Podcast Summary: How I Built This with Guy Raz – Advice Line with Leah Sullivan of TaskRabbit

Introduction

In this compelling episode of How I Built This with Guy Raz, host Guy Raz welcomes back Leah Sullivan, the founder of TaskRabbit, to the unique Advice Line segment. This episode, released on March 20, 2025, delves into the challenges faced by emerging entrepreneurs and startups, providing actionable insights from Leah's vast experience in building one of the pioneering brands in the digital sharing economy. Leah's expertise offers invaluable guidance to founders navigating the complexities of customer acquisition, market differentiation, and product development in a saturated marketplace.

Caller 1: Sian Circlei and the PoppyNotes App

The first caller, Sian Circlei from Los Angeles, introduces her venture, PoppyNotes, an E-cards and greetings mobile application designed to simplify sending personalized digital cards via text and email. Sian outlines her primary challenge: "finding and reaching my audience, particularly as a tech product. It's easy to get lost on the App Store. It's easy to get lost on Instagram" ([12:20]).

Key Discussions and Insights:

1. Market Differentiation:

   • Leah Sullivan emphasizes the importance of carving out a unique niche in a crowded market. She advises, "How can we figure out what the wedge is that you can create that differentiates you and what you're offering people" ([13:53]).
   • Sian responds by considering thematic specialization, such as focusing on specific user groups like parents with school-age children or seniors who wish to connect with distant relatives.

2. Leveraging Influencers and Ambassadors:

   • Kate Pittner suggests, "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" ([15:02]).
   • This approach involves collaborating with mommy bloggers or senior influencers to amplify PoppyNotes' reach and credibility.

3. Creating Virality Through User Engagement:

   • Leah shares the strategy of achieving virality by ensuring that early adopters become active promoters. She mentions, "this is the story of Slack or Dropbox... you need a thousand people who adopt it and those thousand people become the force multipliers" ([17:13]).
   • Implementing referral links or encouraging users to create and share their own PoppyNotes can significantly enhance user growth.

4. Simplifying User Experience for Broader Appeal:

   • Leah highlights the value of intuitive design, stating, "this is really, this is like super plug and play. Like, yes, I can teach my, you know, 82-year-old dad how to use this in like five minutes" ([16:43]).
   • Ensuring that the app is user-friendly across all ages can help PoppyNotes penetrate diverse market segments.

Notable Quote:

"You don't always have all three [Timing, Technology, TAM] at once." – Kate Pittner ([07:10])

Caller 2: Alan Ward and the My Love You Love App

The second caller, Alan Ward from Sydney, Australia, discusses his initiative, My Love You Love, a couples coaching app aimed at strengthening relationships through guided interventions and strategies. Alan articulates his main hurdle: "how do we find our couples and drive up user acquisition? Our committed couples that want to work on their relationship" ([30:09]).

Key Discussions and Insights:

1. Targeting Individual Commitments Within Couples:

   • Kate Pittner prompts Alan to consider focusing on individual users who can then encourage their partners to join. She proposes, "where you have two willing partners to join… maybe you have to look for the one person first" ([33:08]).
   • This strategy involves creating modules that one partner can engage with independently, thereby organically introducing the other partner to the app.

2. Expanding Outreach Through Educational Institutions:

   • Leah Sullivan suggests partnering with homeschoolers and alternative education systems to tap into a growing market segment. She advises, "one of the things, Alan, that you probably have come across… there's a lot of focus on preventing and promoting good mental health." ([49:39])
   • Implementing a gifting subscription model, where purchasing a membership also provides access to classrooms, can broaden the app's reach without significant geographical constraints.

3. Utilizing Book Launches for Marketing and Outreach:

   • To address scenarios where only one partner is ready to commit, Alan announces the upcoming release of their book, "The Eight Love Links." This standalone product serves as an entry point, allowing individuals to begin their relationship journey solo before bringing their partner on board.

4. Enhancing User Acquisition Through Workshops and Seminars:

   • Kate encourages Alan to host free workshops or webinars that introduce potential users to the app's benefits. These sessions can act as a funnel, converting participants into committed users by showcasing the app's value proposition firsthand.

5. Optimizing Branding to Appeal to Decision Makers:

   • Both Kate and Leah emphasize the importance of tailoring the app's branding to resonate with parents, the primary decision-makers. This involves highlighting the app's benefits in enhancing children's cognitive and social development through positive relationship-building.

Notable Quote:

"If you can create a way… then there’s a world where… you push this towards people who are struggling and are looking for ways to resolve the crises in their relationship." – Leah Sullivan ([34:18])

Conclusion

Throughout this insightful episode, Leah Sullivan leverages her entrepreneurial journey with TaskRabbit to provide nuanced advice tailored to the unique challenges faced by Sian Circlei and Alan Ward. The discussions underscore the significance of market differentiation, strategic partnerships, user-friendly design, and innovative marketing strategies in fostering business growth. By focusing on creating specific value propositions and leveraging existing networks and influencers, startups can effectively navigate crowded marketplaces and achieve sustainable growth.

Final Takeaway:

Building a successful brand in today's competitive landscape requires a keen understanding of your target audience, continual adaptation to market trends, and the ability to create authentic connections with users. Whether it's through specialized themes, influencer collaborations, or strategic partnerships with educational institutions, the path to growth is paved with thoughtful, user-centric strategies.

Notable Closing Quote:

"You've got to be focused. You've got to create that wedge in the market and you've got to understand, you got to build brick by brick, baby steps." – Kate Pittner ([54:44])

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This summary captures the essence of the episode, highlighting key interactions and actionable insights, enriched with notable quotes and clear attributions to speakers and timestamps.

Transcript

[Guy Raz]

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[Leah Sullivan]

Hey everyone, it's Guy here.

[Guy Raz]

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.

[Leah Sullivan]

So without further ado, enjoy the show.

[Guy Raz]

Hello and welcome to the advice line on how I built this Lab.

[Leah Sullivan]

I'm Guy Raz.

[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 1 minute message that tells us about your business and the issues or questions that you'd like help with.

[Leah Sullivan]

You can also send us a voice.

[Guy Raz]

[e-mail] and make sure to tell us.

[Leah Sullivan]

How to reach you.

[Guy Raz]

And 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 Guy Ra and we'll put all this info in the podcast description. All right, let's get to it.

[Leah Sullivan]

Joining me this week is Leah Sullivan.

[Guy Raz]

She's the founder of TaskRabbit, the online.

[Leah Sullivan]

Marketplace for services like cleaning, assembling furniture, running errands, and a whole lot more. Leah, welcome back to the show. Thanks for coming on.

[Kate Pittner]

It's great to be back, Guy. Thanks for having me.

[Leah Sullivan]

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 or 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 is 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.

[Kate Pittner]

Yeah. I mean, it was early days, and it's been awesome to see TaskRabbit and the brand. 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.

[Leah Sullivan]

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. Like, it might be hard to convince people why they might need that product or service. When you ran into this dilemma, you know, with TestRabbit at the beginning, how. 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.

[Kate Pittner]

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. But, 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 T's. 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.

[Leah Sullivan]

Yeah.

[Kate Pittner]

And sometimes it's not the right time or the market, or maybe the technology isn't advanced enough. And 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 convergence?

[Leah Sullivan]

When do you remember it really starting to gain traction? Because it didn't. It was not a. It was not an immediate. It wasn't like all of a sudden you flip the switch and people are like, yes.

[Kate Pittner]

No, it really wasn't. I mean, we were this tiny company in Boston for, you know, almost two years before we even opened the San Francisco market. But, you know, once we started opening new cities and we saw the people in every single city in every single market start to use the service, give us great reviews, tell their friends. It was a slow build, but then it, you know, you kind of start to build momentum.

[Leah Sullivan]

All right, why don't we take our first caller.

[Kate Pittner]

Let's do It.

[Leah Sullivan]

Hello, caller number one. Welcome to the advice line.

[Sian Circlei]

Hi, Guy and Leah. My name is Kate Pittner, and I'm calling from Los Angeles.

[Leah Sullivan]

Welcome.

[Sian Circlei]

And I am the founder and creator of the PoppyNotes app on the Apple App Store. I designed PoppyNotes 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.

[Leah Sullivan]

Awesome. Well, welcome to the show. Thank you for calling in. Before we get to your question, let me ask you a couple questions. So this is an app that basically lets you send. It's like a card to somebody. Just a digital card.

[Sian Circlei]

Yes, yes. And it's designed to be very simple. That was the key.

[Leah Sullivan]

Right. And tell me how you. I'm assuming you have a design background. That's how it started. Yeah.

[Sian Circlei]

Yes. I have been a commercial graphic designer for over 20 years, and I partnered with companies like Hallmark, Flagology, Joann 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. And I was able to launch two weeks before Christmas in 2022 on the app Store.

[Leah Sullivan]

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 into, like a text or an email or whatever.

[Sian Circlei]

Yeah, 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, you know, customize the font and color and the size and make it really personal. And then you just click send and you can choose to text it, to email it, you can social share. Kind of has a lot of. A lot of fun options.

[Leah Sullivan]

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.

[Sian Circlei]

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've had a few different developers. I have a great development team, and that's how I kind of started. I had to teach myself how to do the basics, like the UI UX design. I did that myself. And then we built from there.

[Leah Sullivan]

Got it. And the app is for, like, a freemium model. So it's, like, free, but then you pay for some stuff.

[Sian Circlei]

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, you know, breast cancer awareness, and then to receive full access to the entire library. It's. It's a low monthly subscription. US $1.99 a month.

[Leah Sullivan]

Got it. Okay. And before we get to Leah, tell me what question you brought for us today.

[Sian Circlei]

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've definitely dealt with, Leah.

[Leah Sullivan]

Yeah. All right, before, Leah, before we get to. To the question, to Kate's question, do you have questions for. For Kate and for what she's building?

[Kate Pittner]

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, I mean, it's really, really incredible. And so, yeah, I mean, I think I understand the question just reaching that audience. And I think 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 poppynotes, 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. And 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, what are your thoughts there?

[Sian Circlei]

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?

[Kate Pittner]

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, and 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, 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, 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 is, that's differentiated.

[Sian Circlei]

No, that's really good. I actually am thinking too about babies and you know, the idea of, I know when I was in that stage of life too, it's just all encompassing. But I do know a lot of my really popular cards are school age children cards, mom support cards. Those kind of, those kind of things might be really perfect, what you're saying. Yeah.

[Kate Pittner]

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 that I, 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. I 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 ten, like Baby Shower, you know, like not just the lifestyle brand, but very specific because it's just so hard to be in that, that big group. I think you really got to hone in on something that's, that's really differentiated to me.

[Leah Sullivan]

You know, a lot of these, these different apps are, I mean, you know, we, we've had Canva on the show and, and, and you know, some of these other companies on the show and brands on the show and they're awesome. They, 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, like super plug and play. Like, yes, I can teach my, you know, 82 year old dad how to use this in like five minutes.

[Sian Circlei]

That's the goal.

[Leah Sullivan]

Yeah. And, and that to me seems like an opportunity. That's a sort of maybe senior citizens too. You know, I talk to my dad every day and my mom and they, they want to talk to their grandkids. And maybe this is something that there's a way, especially on the blog, because I notice 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 re. Send a message to your grandkids with just a funny photo and you're a funny message?

[Sian Circlei]

It'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. I need to do a little bit more of that, I think.

[Leah Sullivan]

Yeah. One other quick thought, which is creating virality. Right. And 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. Um, and, and this is a, this is a highly researched number which is the argument that to start something to create momentum for a brand or product, you need a thousand people who adopt it and those thousand people become the force multipliers. Right. And so is there a way. And I don't know the exact answer, but, and I, 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?

[Kate Pittner]

I love that.

[Leah Sullivan]

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 gotta 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.

[Sian Circlei]

Okay, that's a good idea.

[Leah Sullivan]

And then you get 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. If you think about it, you probably have hundreds of people distant, you know, people all over, you know, 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.

[Kate Pittner]

Absolutely. And now you have two more fans right here. So thank you so much.

[Sian Circlei]

That means so much.

[Leah Sullivan]

About to send a poppy note right now to Leah.

[Sian Circlei]

Absolutely. I love it. Thank you very, very much, both of you.

[Leah Sullivan]

All right, Kate Pittner, poppy notes. Good luck. Congrats.

[Sian Circlei]

Thank you so much. Take care.

[Leah Sullivan]

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. That's all I want.

[Kate Pittner]

Yes.

[Leah Sullivan]

I have all those cards for my kids.

[Kate Pittner]

Yes. Now I'm gonna say, make me a poppy note.

[Leah Sullivan]

Make me a poppy note. You know, the stick figures, it's like there's something really special about that, about a. Yeah, so I'm thinking about Kate as a little girl, always wanting to have a greeting card company.

[Kate Pittner]

Yes. It's the dream.

[Leah Sullivan]

I love that it's a dream. I love that it's a dream.

[Guy Raz]

All right, we're going to take a quick break, but when we come back, another caller, another question, and another round of advice.

[Leah Sullivan]

I'm Guy Raz.

[Guy Raz]

Stick around.

[Leah Sullivan]

You're listening to the advice line on.

[Guy Raz]

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[Leah Sullivan]

So Leah, let's bring in our next caller. Hello, welcome to the advice line.

[Alan Ward]

Hello Leah and Guy. My name's Sian Circlei and I'm from Sydney, Australia and I'm delighted to be here talking talking to Today.

[Leah Sullivan]

Welcome to the show. Tell us a little bit about the name of your product and what, what it does.

[Alan Ward]

Yeah. So along with my wife, I'm the co founder of My Love youe 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.

[Leah Sullivan]

Wow. 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 it work. It's an app you download and presumably designed for people who are having problems or what?

[Alan Ward]

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, but it's really designed to make your relationship robust and deepen your bonds over the lifetime.

[Leah Sullivan]

And tell me a little bit about you and your wife. I'm imagining both of you guys are therapists.

[Alan Ward]

We are indeed. So we're both clinical psychologists and we're both couples therapists as well. So it means that, you know, I can tell you we have a great relationship, but we've had plenty of conflict. And you know, 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, the 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. One 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.

[Guy Raz]

Huh.

[Leah Sullivan]

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? And 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.

[Alan Ward]

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. So we thought we need to get this out there to prevent the problems before they happen.

[Leah Sullivan]

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 we ignore. But essentially what you're saying is if you can. 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.

[Alan Ward]

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 positive behaviors are protective of the relationship. So, 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.

[Leah Sullivan]

And how much? What's the cost?

[Alan Ward]

Okay, so it's $108 per year if you want to get the yearly version, or $17.98 per month.

[Leah Sullivan]

So on the higher end of apps, but presumably a lot cheaper than going to. Going to a therapist.

[Alan Ward]

Absolutely. It's a lot cheaper than just one couple's therapy session.

[Leah Sullivan]

And, Sean, what's the question you brought for us today?

[Alan Ward]

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, you love journey. And so my question is, how do we find our couples and drive up user acquisition? Our committed couples that want to work on their relationship?

[Leah Sullivan]

Because each couple has to. Every user pays the monthly or the yearly fee, right?

[Alan Ward]

Yes. But to be clear, when I say 54, $108 per year, it's $54 per person. Or at 17.98, it's $8.99 each. So we like to advertise the total price per couple so people don't get a shock with that.

[Leah Sullivan]

Right. All right, Leah Sullivan, I'm going to bring you in here before we answer Sean's question. Any questions for him?

[Kate Pittner]

I have so many questions, Sean. So you are doing such important work. I love feels like the real question is, how do you get people to take their vitamins every day? Right. It's like all about prevention and healthy relationships. I mean, in technology, we always talk about, okay, is this product a vitamin or is it a painkiller? And you've got a vitamin here. So we gotta think about how do you sell vitamins? Right.

[Alan Ward]

Absolutely.

[Kate Pittner]

Are you tied to making both couples sign up at once?

[Alan Ward]

At the moment, yes. It's the way the app works. But I can tell you we did get people saying, how do I get access to this information if my partner's not ready?

[Kate Pittner]

Yeah.

[Alan Ward]

So I'm very excited to announce what we did in response to this. After we're exhausted finishing the app is we wrote a book, and the book's called the eight Love Links. So that's going to be out any day now, and people can take the solo journey. And the book is a standalone product, but it does mention the app. It says in parts, when you're ready, you can take the practical application with your partner.

[Kate Pittner]

That's great. That's so exciting. I love that. Yeah. So I think if. If there are other ways to soften the onboarding because you're immediately shrinking your market down to couples, two people who are willing to both onboard at the same time. So just it's going to be a smaller market from the beginning.

[Alan Ward]

Absolutely.

[Kate Pittner]

So thinking through, can I soften this? Are there ways to onboard? Are there interactions that become the on ramp to both couples? I would think through that a little bit more from an app standpoint, you know, I would think about where Are the couples. But where are they happy and where are they already doing some of this work? Are there couples retreats? Are there travel, hotels, resorts, something that you could kind of partner with to, you know, offer this as part of their check in process or part of their package, you know, or something. And so I would just think about, okay, where are the couples right now, today, at this moment, you know, that would use this. They're. They're probably not in therapy, right. Because they're already, they're already feeling the painkillers. They're needing the painkillers. You need to sell the vitamins.

[Alan Ward]

Absolutely. So would you recommend, for example, that we try and get in front of these couples and like maybe give them some free, like a free workshop?

[Kate Pittner]

Yeah. I mean.

[Leah Sullivan]

Yeah.

[Alan Ward]

Then mention the ad something to that sort of experience. Okay, that sounds like a great idea.

[Leah Sullivan]

And then the other question I have, Leah and Sean, I mean, you know, obviously for couples therapy to work, you need both partners willing to do it. But I think in a lot of cases Sean and you probably experience this, it's one partner who really kind of drags the other partner in and the other partner is often kicking and screaming or, you know, just not interested. But you know, it can be really beneficial. So I wonder whether there's a world where, you know, going back to Leah's analogy of the painkiller versus the vitamin, where this is a painkiller, where essentially you are pushing this towards people who are struggling and are looking for ways to resolve, you know, the crises in their relationship. And it may not be that you have to look for the couple, but you just have to look for the one person first.

[Alan Ward]

You know, I've got to say, guy like that, that definitely parallels what we see in therapy. Now, don't get me wrong, I always say when we have two invested parties, we're going to get the best results. However, often there's an over somebody who over functions a bit for the relationship that brings a couple in and we still do get amazing results. So I think that's a really good idea. We just need to really connect with that one person who will then kind of like be the encourager for the, for the couple.

[Kate Pittner]

I would also think about along those lines. Are there certain, I think you called them interventions or interactions or certain modules that could entice the other person in the relationship and can you give the other person who's dragging the other one along some tools? Can you empower them through these interventions to bring in the other person in the relationship?

[Alan Ward]

Leah, do you Mean through the app, like get them on the app first and then give them the strategies to do that.

[Kate Pittner]

Yes.

[Alan Ward]

You know, I've never thought about that, but that is a really fantastic idea for us to think about because we do get like, we get registrations and we have reached out to people who have registered but not gone on to use the app. And sometimes the feedback is, you know, my partner, I'm looking, I'm not sure my partner's ready. So that's a really good idea.

[Kate Pittner]

Yeah, just offer them maybe one module or one intervention and just say, hey, could you just try this one interaction through that?

[Alan Ward]

Yeah, great. I don't think that would be too hard. I think actually I haven't thought about it in this sense, but we could do like an extra module that is just for each partner to do on their own. And even if they both connect at the same time, they can work through the introductory model first and we can kind of really talk about some tips and insights to really try and get both people invested.

[Leah Sullivan]

Right. And are you, and you mentioned like doing like sort of seminars and talking to people and giving them the opportunity to use this for free, which I think is an interesting and smart way to go about it. And I'm looking at your website here for your landing page and I see you've got some press coverage. I mean, you've got coverage certainly in Australia and on podcasts and the Times. I don't know if that's from the UK or from Australia.

[Guy Raz]

And are you finding those?

[Leah Sullivan]

I mean, have those generated interest at the very least, or users?

[Alan Ward]

Yeah, absolutely. I think when we've had good press, we get a spike in registrations and users. One thing I'm really delighted to say is between 70 and 75% of all people who do the free trial. I don't know if I mentioned that actually you get a seven day free trial before you get charged. 70 to 75% of those people go on to subscribe to the app. So I think the thing with media is it is hard to get and some of the. Unfortunately I think we went to market a little bit too early and some of the great media we got. The app was not in its current form. We've had many iterations of the app. In fact, we totally redesigned it and changed it for user experience. It's been in its best form probably since about March of this year. But with the book, we are hoping to generate more publicity around the book and then secondary publicity for the app as well.

[Kate Pittner]

Well, the book is a great excuse Too, to take it on the road. Right. Do a book tour, get on the road, do some seminars that are connected to the book. And that seems like an awesome opportunity.

[Alan Ward]

Yeah, absolutely.

[Leah Sullivan]

For sure. The product is called My Love youe Love. It's an app. Sean Soreckley, thanks so much. Good luck.

[Alan Ward]

Thank you both for having me. I am a big fan of the show also and it's been an absolute delight. I feel very privileged. Thank you.

[Leah Sullivan]

Thank you. Yeah, I mean, I mean, yeah, it seems like a great. Right. Because couples therapy's got, I mean, I, I, we've had Esther Perel on my, on my other shows in the past. And I always think of Esther when I think of couples therapy because she.

[Kate Pittner]

Of course, love her.

[Leah Sullivan]

She's like the, the, you know, sort of the, the guru of it, you know, probably the best known couples therapist in the world. I mean, that's, it's cool. It's a idea, right? Because a lot of it's expensive for people to go and pay for any kind of therapy.

[Kate Pittner]

It is. No, it's a great idea. I mean, like I said, it's really important work. I mean, how good are you though at taking your vitamins every day?

[Leah Sullivan]

Well, you must know. I'm pretty good at it. I do take them. Yeah, I'm pretty good at it. But I hate to say that now I sound self righteous, but I have them. Here's my secret. I have them next to the coffee machine. And it drives my wife crazy. Maybe we should go use this app. It drives her crazy because she's like.

[Guy Raz]

People come into our house and they.

[Leah Sullivan]

See your vitamins all laid on the shelf next to the. And what I say, she says, can you hide them? And I say, if I hide them.

[Guy Raz]

I will not remember to take them.

[Leah Sullivan]

I will literally forget. Like, that's how my brain works.

[Kate Pittner]

I love that. So, yeah, that's the point. It's like, you've gotta have a routine. Right?

[Leah Sullivan]

Gotta have routine.

[Kate Pittner]

Gotta have a routine. It's good.

[Leah Sullivan]

It's gotta be just. It's like a Pavlovian response. I don't even think about it. I just, I make my coffee, I've got my vitamins. They put them down, I take them.

[Kate Pittner]

I'm gonna try this tomorrow.

[Leah Sullivan]

Yeah. It's the way to go.

[Kate Pittner]

Yeah.

[Leah Sullivan]

I wish I could do that with everything. Like with meditation. Cause I forget to do it.

[Kate Pittner]

Yes.

[Leah Sullivan]

Or stretching. When I stretch every night, it's great. Maybe I should put my stretching next to the coffee machine.

[Kate Pittner]

Coffee machine, coffee machine. That's the answer.

[Leah Sullivan]

That's the answer, you know. All right, stay with us because after.

[Guy Raz]

The break, we'll talk to another founder working to take their business to the next level.

[Leah Sullivan]

I'm Guy Raz, and you're listening to.

[Guy Raz]

The advice line right here on How I Built this Lab. This message comes from Schwab. With Schwab Investing Themes, it's easy to invest in ideas you believe in, like online music and videos, artificial intelligence, electric vehicles, and more. Schwab's research uncovers emerging trends. Then their technology curates relevant stocks into over 40 themes to choose from. Schwab Investing Themes is not intended to be investment advice or a recommendation of any stock or investment strategy. Visit schwab.com thematicinvesting this episode is sponsored by Canva. If you make decks at work, you should make the switch to Canva Presentations. Canva Presentations might be the most visually impressive presentations you'll ever use. Start with a stunning template. Drag and drop images, graphics, charts and data visualizations from Canva's massive media library. Add animations plus interactive polls and quizzes to really set your slides apart. Built in AI also lets you generate slides and text in seconds from a prompt. And you can share your Canva presentations with anyone and instantly collaborate in real time. Canva is used by 95% of Fortune 500 companies. Whether you work at a small or big company, in a team of two or two thousand, Canva empowers workplaces everywhere to create captivating presentations, save time and be more productive together. You'll love the presentations you can easily design with Canva. Your audience will too. Love your work with canva [e-mail]. hey, welcome back to the advice line on How I Built this Lab. I'm Guy Raz and today I'm taking calls with Leah Sullivan, the founder of the company TaskRabbit. So Leah, let's bring in our last caller.

[Kate Pittner]

Let's do it.

[Guy Raz]

Hello caller. Welcome to the advice line here on How I Built this. Please introduce yourself and tell us a little bit about your business.

[F]

My name is Alan Ward and I'm calling from Honolulu, Hawaii.

[Leah Sullivan]

Nice.

[F]

I'm the co founder of Dynabuddy. Dynabuddy is a streaming service that helps kids learn to play music. Our goal is to give more people access to high quality music education at an affordable price.

[Guy Raz]

Amazing.

[Leah Sullivan]

Okay, well, first of all, mahalo. So good to have you here.

[F]

Thank you.

[Leah Sullivan]

Alan. Thanks for calling in. I wish I was there. You know, I'm in California, so it's not too bad. So. All right, so tell me a little bit about Dynabuddy. It is an online platform that teaches kids how to play instruments, correct?

[F]

Yeah, so it's a streaming service, so online play along videos. And the videos are carefully sequenced to teach kids from day one who may have never held an instrument like, how to play. And we'll work them through about the equivalent of the first two years of band instruction. My wife helped me design it. She's a musician too. And we carefully set up our scope and sequence our whole curriculum to align with national standards. And we have videos and curriculum for all standard band instruments. So all of the woodwinds, the brass and percussion instruments that kids may typically learn in public schools.

[Leah Sullivan]

Got it. Okay, so this is. So these are streaming videos called Dinah Buddy because it's their dinosaur characters that teach kids how to do these things.

[F]

Dyna Buddy. Yes, you got it. The name of the company is A Play on Words. And so we. We wanted to take the word dynamic, D, Y, N, A, which is a musical term, and like fuse that with dinosaur to sort of imply music friend. And my cousin was the graphic designer for this, and he described the whole project as sort of a Trojan horse for music education where the kids are just having a fun time doing this thing, and they walk away being able to play and understand music a whole lot more.

[Leah Sullivan]

Got it. Okay, so. And tell me what. What your question is for us.

[F]

Yeah. So, Guy and Leah, from your perspective, how can we recruit early adopters and find our ideal product market fit?

[Leah Sullivan]

All right. Okay, lots to unpack here. Leah, questions for Alan.

[Kate Pittner]

Alan, tell us a little bit more about the specific target age group that this is best for.

[F]

Yeah, so ideally the target age range is, you know, about the fourth to sixth grader and would support them. Currently, what we have up would support them for about two years.

[Alan Ward]

And.

[F]

And we have our curriculum mapped to support students all the way through the end of high school.

[Kate Pittner]

Okay, got it. And it seems like the idea and the strategy and sort of the go to market plan has been through the school system. Is that correct? Are you really tied to that as the strategy?

[F]

That was the original idea. And one thing I've been paying attention to is the rapidly changing educational demographics in our country, and especially the prevalence of home schools, micro schools, charter schools, and the increasing number of families that are looking for alternatives to the public school experience. And so, yeah, I am not tied to the public schools as our market.

[Kate Pittner]

Yeah, I mean, I think that's good to hear. Just because I do think that, you know, from a. From a venture Investor standpoint, which is where my brain works. You know, the industry is so fragmented, it's slow, it's underfunded, and there's not a lot of room, you know, to innovate. And so I think thinking through, you know, other strategies of getting dyno buddy into the right audience, into, you know, that. That early adopters, as you said, that's really gonna grasp what you're. What you're doing here and take it and run with it, I think, is what you want. I mean, one idea I have for you, Alan, is have you thought about. There are a lot of, I think, music teachers or people that are passionate about teaching music to kids. You know, I just wonder if there are ambassadors or people that could utilize this as part of their curriculum and kind of helping to streamline, you know, what they're. What they're teaching and how they're teaching it. And can you make this kind of a standard for music teachers who want to help kids at that age?

[F]

That is a phenomenal idea and something we've thought of and I'm trying to actively set up at the moment. I have been doing clinics in local public schools and would love to get this into a teacher training program, say, for example, at a university where they're sending out the next generation of music teachers. And those people are much more open to new ideas, usually than established teachers on the ground. And we see that as a huge opportunity.

[Leah Sullivan]

One of the things, Alan, that you probably have come across, and I know that you have been kind of seeing if you could connect with homeschoolers, a lot more kids being homeschooled, which is a really interesting phenomenon and market. And I have a kids media company. We make kids podcasts and other kids books, science around science. And we have a lot of homeschooled kids who listen to WOW in the world or read our books. But the challenge, as I'm sure you faced, is schools. It's really hard to get anything into schools. There's big bureaucracies, and they're also strapped. They just don't have the budgets. But one thing that has been successful for us at Tinkercast, we have an online platform that teaches kids critical thinking skills using our audio podcasts is we basically every time somebody buys a membership, we gift one to a classroom. So we're giving it away, but we're also encouraging people to use it with the hopes that some of the kids might come home and say, can we get this, too? And so there's an opportunity here, I think, for you to Create a way and certainly starting it in Honolulu, where you're based, but trying to expand it from there, where somebody could buy a membership and then you will gift one to a classroom or that they can gift one to a classroom. Like I think that you might want to experiment with these kinds of tiers because what you really want to do is get it in. And I know you're doing this, but you really need to get it in front of as many eyes as possible. And you won't be able to go all over the country to do that. You need it to grow without you being there. And so one of the ways to do that, I think is to try this gifting subscription model.

[F]

Love that idea. Yeah. And the way you have that structured is the person who's purchasing the product and then electing to give the gift, are they choosing where the gift goes or is that an internal decision?

[Leah Sullivan]

We usually give them to like Title 1 schools around the country, you know, where kids don't have access to the same kinds of resources. So, so that's one approach. You can decide how you want to do it. Maybe it's for homeschoolers. However you decide it to do it, you can create a mechanism where kids get exposed to this. I mean, look, we know there's so much research behind this and I'd love to see you push this a little bit more on your website because your website's nice, but it's very simple. And I understand that you probably are limited in your budget, but there are things you can do even on a limited budget to get that message across, which is to say parents. And Leah, I think you can attest to this. We're interested in enhancing our kids brains, right?

[Kate Pittner]

Yes.

[Leah Sullivan]

Whether it's keeping them away from screens or exposing them to different activities. And music is like number one at the top of that list. You get kids playing an instrument and I'm sorry, my kids just, I couldn't get them to keep practicing piano. But you know, you get them doing that, it switches something on in their brains early in their lives. And that's also something I'd love to see more of on your website.

[Kate Pittner]

I agree with that too. And I think to Guy's point, just the homepage of your website too, making that more geared to parents or who the decision maker is going to be. Right. Because it looks super fun for the kids, which is awesome. But as a parent, I want to come here and I want to be compelled to. Oh yeah, I'm going to get my little guy signed up for this because it's going to have X, Y and Z benefits and look how fun and easy this is going to be. So I would think a little bit more too about who the decision maker is, who is the buyer and kind of reposition the brand and the ask to those people.

[F]

That makes complete sense. Yes. Originally we had designed things to make it fun and appealing for the young ones. And yeah, as the more I've thought about it and gone through things and realized I'm really just speaking to the parents and need to message towards that. But. But yeah, I, I hear what you're saying and agree with it and we'll follow through with those changes.

[Leah Sullivan]

Alan Ward, Dynabuddy, thanks so much for calling in. Good luck man.

[F]

Thank you so much. Been a huge fan of the show, listening for years. Thank you.

[Leah Sullivan]

Thank you. Well, Leah, did you get your kids to any of your kids instruments?

[Kate Pittner]

You know, the middle guy right now, he's just really. We started with piano, now he's into guitar, you know, anything.

[Leah Sullivan]

Yeah, awesome.

[Kate Pittner]

Percussion.

[Leah Sullivan]

Yeah, some kids just get, you know, I do another show called the Great Creators. I interview a lot of musicians and it doesn't matter who it is, Jeff Tweedy or you know, or Bjork or any of these people that have been on the show, they all just. Something in their brains clicked when they were little and they just wanted to play instruments. And I think there's some kids who are forced to do it and then eventually they just like, you know, surrender and they're like, I actually like this. And then there's some kids who just. It's punishing, you know. But our kids were good at piano. We just. The pandemic happened and then like we tried online piano and it just. Cause it kind of fizzled away. So I failed. I failed as apparently.

[Kate Pittner]

Well, I'm sure you're succeeding in many other ways, guy. I'm not worried about.

[Leah Sullivan]

You don't have future members of the New York Philharmonic. Oh, well, all right. Well Leah, hopefully we can check back in in a couple years with some of these folks and they'll be like, yeah, that was it. That advice turned it around.

[Kate Pittner]

I would love that. I would love to see it. I think all of these companies are doing something so unique and really special. So it's really fun to talk with them.

[Leah Sullivan]

When you think about what you wish you knew or what you might have told yourself early on in 2008, that knowing what you know now with all your experience and I mean just, you know, you've sort of seen hundreds of companies. Now, as an investor, what do you, what would you advise yourself or told yourself back then?

[Kate Pittner]

Yeah, I mean, I think it really is. And we saw this today with all of these founders and companies. It's about focus and prioritization. I think as a founder you have so many ideas, you see all the possibilities and really you have to pitch all of those possibilities to kind of bring people in and inspire them and get the company off the ground. But when it comes down to execution and customer acquisition, you've really got to be focused. You've got to create that wedge in the market and you've got to understand, you got to build brick by brick, baby steps, you know, to get to that full North Star vision.

[Leah Sullivan]

Yeah, totally, totally agree. Leah Sullivan, founder of TaskRabbit, thank you so much for coming back onto the show.

[Kate Pittner]

Thanks so much for having me, guy. It was a lot of fun.

[Guy Raz]

And by the way, if you guys haven't heard Leah's original How I Built.

[Leah Sullivan]

This episode, you have to go back.

[Guy Raz]

Back and check it out. You can find a link to it in the podcast description. But here's one of my favorite moments from that interview.

[Kate Pittner]

So we're scaling up and we're also realizing that the product now in 2011 is, it's just not working. It's just not working. And at this point there are competitors coming out that are launching mobile first, mobile only. And we've been on the web. I mean honestly, it's like the, the entire consumer market and expectation just changed underneath us and we missed it.

[Guy Raz]

Hey, thanks so much for listening to the show this week. Please make sure to click the Follow button on your podcast app so you never miss a new episode of the show. And if you're interested in insights, ideas and lessons from some of the world's greatest entrepreneurs, sign up for my newsletter at Guy Raz or on substack. And if you're working on a business and you'd like to be on this show, send us a one minute message that tells us about your business, the issues or questions you'd like help with and hopefully we can help you with them. And make sure to tell us how to reach you. You can send us a voice [e-mail] or call us at 1-800-43 and leave a message there. And we'll put all this in the podcast description as well. This episode was produced by Kerry Thompson with music composed by Ramtina Rabloui. It was edited by John Isabella. Our audio engineer was Robert Rodriguez. Our production staff also includes Alex Chung, Chris Masini, Carla estevez, Elaine Coates, J.C. howard, Katherine Cipher, Devin Schwartz, Neva Grant and and Sam Paulson. I'm Guy Raz and you've been listening to the advice line on How I Built this Lab. If you like How I Built this, you can listen early and ad free right now by joining Wondery in the Wondery app or on Apple Podcasts. Prime members can listen ad free on Amazon Music. Before you go, tell us about yourself by filling out a short [e-mail] wonder survey it takes a lot to grow your business. You've got to attract audiences, score leads, manage all the channels. It's a lot of long days and late nights, but with Breeze HubSpot's new AI tools, it's never been easier to be a marketer and crush your goals fast. Which means pretty soon your company will have a lot to celebrate, like 110% more leads in just 12 months. Visit HubSpot.com marketers to learn more.