The Exchanges

Q Yeah. Alright, so, 2001, I believe, you graduate from Sweetbriar with a degree in computer science, and I think you get a job as an engineer at a small software startup, which I guess eventually gets merged into IBM, and what are you doing for them? Were you coding?

A I actually started as a quality engineer, so I wasn't doing any programming, they wouldn't let me touch the code, but I was the tester, so I would find all the bugs in the code, I would write up the bugs, And then I'd work with the developers and the engineers to fix them. I did that for five years, um, but I always wanted to be the programmer. I always wanted to be the coder. It was really hard for me to break into that side, though. Um, you know, and I saw other IBM, you know, interns coming in right out of school and joining as engineers, and I'm like, why aren't I coding? Why aren't I programming?

AI assessment note: “I actually started as a quality engineer, so I wasn't doing any programming”

Q At the time, Four Hour Workweek was like, all, it was a huge deal, right?

A Yes. So I had read Four Hour Workweek, and particularly as it related to RunMyAaron.com, I thought, oh my god, if I could get Tim as an advisor to this company, that's going to be a huge win for us. And it just so happened that Tim was going to speak at Facebook Fund on a Monday morning. Now, I was flying back and forth, right? A week in Boston, a week in Palo Alto. So the head of the Facebook program says, okay, Monday morning, Tim Ferriss is gonna be here. Surprise! What, you know, everyone can sign up for 15 minutes with Tim on Monday. I'm literally on a flight back to Boston when I get this email. I'm like, oh my god, do I really turn around just so I can have this meeting with Tim? I look online to see how much a plane ticket is to fly back. It was like 700 dollars. It was a lot. And I think, okay, it's a 15 minute meeting with Tim, like, is this really worth it? Yeah. But, I decide that I'm gonna make it worth it. I'm just gonna, I'm gonna make sure that he comes on an advisor, like, whatever it takes. And so, I book my ticket back on Sunday night, so I'm in Boston for a day, go back on Sunday night, And on the way there, I read the four hour work week again. So I just have it fresh in my mind. Yep. I have the 15 minute meeting with Tim, and I'm showing him the site, and I'm describing Run My Aaron to him, and he's giving me feedback about the homepage. And it's 15 minute…

AI assessment note: “Yes. So I had read Four Hour Workweek”

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

A 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. Um, and so, yeah, I mean, I think I understand the question, just reaching that audience, and I think, um, 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. Um, 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, 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?

AI assessment note: “I'm wondering how can we figure out what the wedge is that you can create”

Q Do you feel, I mean, you're, you know, five years plus removed from TaskRabbit now. Is it, I mean, do you have any emotional attachment to it, or, or not anymore?

A Oh, God. Um, I, I do. It's, it's, so as a founder, I always felt like, wouldn't it be amazing to build something that lives beyond you? And that's what I got to achieve, and that was incredible. Now, the flip side of that is there's this company that lives beyond me, That I have no control over anymore, but everybody associates with me. And so sometimes I'm on the opposite end where people are like asking me questions about like, oh, and you know, what do you think about this with TaskRabbit? And what do you think about this decision or that? And I'm just like, wow, I like, I have no input. No, I'm very detached, very detached. I know a handful of people at that company. Today. So it is sort of odd for me because it, it was my baby. It is my baby. It was the first, the first baby. Um, and so it is this very conflicting feeling at times. I'm proud that it lives on beyond me, and I also sometimes feel a conflict that I'm no longer a part of it.

AI assessment note: “I, I do. It's, it's, so as a founder”

Q on, having created one of the best-known mobile marketplaces in the country. Leah grew up in a little town outside of Boston. Her dad ran training programs at a nearby Air Force base while her mom looked after the family. As a young girl, Leah was really into dance, but when she got to college at Sweetbriar in Virginia, she took her first programming courses and got hooked. On C++?

A For me, it was the opportunity to be able to build whatever was in my mind. I mean, I, I, I am very imaginative. I, I have ideas all the time, and, um, I'm not really good at delegation, and so the, the idea that I could take what was in my head and build it so that someone else could see it or use it or interact with it, Was really exciting. I mean, I remember it was the simplest, simplest assignment, which was taking this little JPEG robot and being able to code it so that with the arrow keys on the keyboard, it could move around the screen. And honestly, it was, that was enough for me to understand how powerful programming and engineering could be.

AI assessment note: “For me, it was the opportunity to be able to build whatever was in my”

Q might need that product or service. Um, When you ran into this dilemma, you know, with TaskRabbit 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, or go run an errand for them and bring it to their house?

A 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, um, 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, um, 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.

AI assessment note: “it really comes down to three things. Timing, technology, And TAM”