The Exchanges

Q Which meant that, what, you'd have to wait another year, basically?

A That's right. And I, I just didn't have the time to wait for that, and so I asked some people that I had met in San Francisco to connect me with the partners in Y Combinator, and then finally I get one response, and it was Gary Tan, one of the, the partners at Y Combinator, he said, Look, it's likely not going to work, but you can, you can fill out a late application. So I filled out a late application, and then finally I get a response from him, and he says, nope, it's too late. And I was like, god, this is, this is, this sucks. And I was thinking about it, and I was like, this guy, does he even know what Instacart is? Has he even tried out the product? Does he even know why it's different? And so what I did was, I opened the app, I ordered a six pack of beer, and I addressed it for the Y Combinator headquarters. And half an hour later, I get a call from Gary Tan, and he's like, what is this? And I was like, oh, this is Instacart. And I guess the beer must have been pretty good, because he asked me to come in the next day for an interview. And so I show up for the interview the next day, and soon after that, I was accepted. And so that's how, you know, Instacart got funded.

AI assessment note: “That's right. And I, I just didn't have the time to wait for that”

Q So, I mean, in those, you know, those sort of first two years or so, were, were investors like beating down your door to invest in this as, as people started to download the app and use it?

A You know, I wish that was the case. Um, uh, you know, it was, it was pretty hard, to be honest. I think that, um, you know, early on, it wasn't very obvious to most people that this would become something, and, um, because there had been other ideas like this before, like Webvan back in the day, and during the dot-com era, and that was one of the biggest failures of All time. Like, it literally lost billions of dollars. I remember one time I was pitching a venture capitalist, and, um, you know, we were in a conference room, and he suddenly gets up, and he leaves the meeting. I was confused. I was like, well, I was in the middle of the presentation, and he came back with a floppy disk in his hand, and he sort of slams it on the, on the table, and he's like, go home and, uh, study what's inside this floppy disk. Because it has the web van business model. And so you need to understand that really well and why it didn't work. And I was like, well, this guy is just so smart. And, you know, it was like, well known, uh, uh, person in Silicon Valley. And like, I, I must be completely wrong. And thankfully, I guess I didn't have a way to open the floppy disk, but it just didn't have floppy drive. But, um, uh, so I never really looked at the business plan there, but you know, it was just, it was There's a lot of self-doubt, you know.

AI assessment note: “I wish that was the case. Um, uh, you know, it was pretty hard”

Q Um, what, what, what, What keeps you up at night? Like, like, drones delivering groceries to people? Or, like, what is it that you're worried could, could, like, knock you guys off?

A I think that it really is just our lack of execution that I think will be the cause of our failure if we end up failing. That's what keeps me up at night, and it's, it's little things like, uh, this small element of, of a meeting, um, just did not go well, or project is not going well, even though it may not be the most important project in the company, but to me, that's a sign that, that we're not doing our job well overall, and That transfers to, to other important things. Um, and so to me, I think it's making sure that, that the team is working on, um, all the little details and, and they're paying attention to those details and doing a great job at it is very important. And I, when I, when that doesn't happen, I get pretty stressed out.

AI assessment note: “it really is just our lack of execution that I think will be the cause”

Q So would you, I mean, was it super exciting? Were you having just like tons of fun?

A It started off being really interesting and fun because I was learning a lot of these interesting things like how to, what business models work and what don't, what, um, how to build a prototype really, really fast, how to advertise. But then sort of, you know, after going through all these ideas, I, I was getting pretty tired. I was getting tired of sort of failing. I remember this was a pretty low point in my, in my life when I was like, well, am I even cut out to be an entrepreneur at all? And, um, You know, I remember sort of one idea that was sort of something that had been, um, uh, in my mind, and I thought that this idea was just brilliant. This is going to be the one that is a home run. It's just, you know, it's going to be awesome, and the idea was A social network for lawyers.

AI assessment note: “It started off being really interesting and fun because I was learning a lot”

Q And was the company, was the concept proving to be successful in any way, or was it, did it seem pretty clear that it just wasn't working?

A I think that, um, it could have worked. Um, but what I had been doing so far in, in my journey as a, as an entrepreneur was that I had been looking for good and quote unquote business ideas, and they were not necessarily business ideas that I cared about. They were just business ideas. And sort of that's when I realized that the odds of success in a startup are so low. Anyway, you sort of have to go, uh, You have to put everything that you have in it. You just can't do that for an idea that you just don't care about for, and, and that's when I said that I, I just can't do this, and I quit my own startup.

AI assessment note: “I think that, um, it could have worked.”

Q How were you able to turn that around?

A I mean, it's, it's hard to, um, pinpoint one sort of single, you know, aha moment, but it was sort of a, a feeling in my mind that it had been developing over the, the whole entire year, which was that I should be doing something that I care about. I should be doing something that I'm passionate about. And it turned out to be something that was sort of pretty close to home. And that was the fact that Ever since I can remember you from, you know, childhood memories, I'm talking about the, I had always hated every aspect of grocery shopping, going around around in the aisles in a grocery store, or waiting in line at the checkout, or in some cases, you know, frankly, memories of being in Canada and waiting for the bus with all the bags in your hands and your, your fingers are just Freezing in the cold. You know, everything about it to me was just painful. And for the last two years of my life, I had just worked on building all these cool apps and products and so on. And, and I realized that I did everything online. I did, I bought stuff online, like books or, or whatever. And I met people online. I, I watched TV online. I was doing everything online. But the one activity that I've always hated in my entire life, I was still doing in the most inefficient way possible. To me, that was a problem that I cared about. That was a problem that I was so passionate about that I had to solve…

AI assessment note: “That was a problem that I was so passionate about that I had to solve it.”