Tips from the Designer of Instacart & Y Combinator, Zain Ali

This interview has been edited for concision and clarity.

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Watch the full interview here:

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BLD:
Hey everybody, I'm Agree. I'm Harrison. And this is Bottom Line Design. Today we have a very special guest on the show. Someone who we've been following for some time. Zain Ali, who was the founding designer at Instacart, right?

Zain:
Yep.

BLD:
And then led design at YC before going off to start his own thing with Nature's Keeper, which we'll definitely get into as well. But I want to, before we get into all that, I want to go to ground zero, I want to hear about your career start in gaming.

Zain:
Oh wow, that's funny. Sure, yeah, let's do it. Yeah, you know, I was a big gamer growing up. I think a lot of us were, you know, like in the 90s you had Super Nintendo and all that good stuff.

Zain:
I just had an affinity towards games because my dad liked sharing that experience with me and my uncle as well. My uncle was a pilot, so we played fighter jet games a lot. So I got really into games. I love skating and stuff, but gaming just became a big outlet for me. And so when I was in high school, I started competing in Call of Duty. This was like Call of Duty 2. And that was my first foray into competitive gaming. I had played Counter-Strike competitively a little bit, but Call of Duty was where I really got serious into it. And the reason why I bring that up is because that's how it really began my journey into design. I started building a computer to play games, and then that led to me downloading software to design and stuff like that. And when I went to school in San Francisco, I was looking for a job. I found an internship on Craigslist, a gaming internship. It was kind of obscure, but it was a gaming news site or something like that. And they were looking for interns. And so I remember just emailing tons of ads on Craigslist, like I can do that job, I can do that. Oh, VP, yeah, I can do that. And had no idea, right, what was going on. And I remember walking into this startup in Soma. It was called Got Game. and the founder David Hua invited me in there because I had emailed him an application and I answered a bunch of questions and the last question on that application was, why should we pick you? And I said something like, I pwn noobs or whatever, something like that. This was like 2008 or something, so I was really like, at that point I had emailed so many ads and stuff like that.

BLD:
Yeah.

Zain:
was like, you know what, let me just take this shot. And he invited me in to chat. And that literally was how I got into startups. Got Game was really in its MVP stage. We were building a social app for gamers. It was the Steam before Steam. Steam kind of sucked back then and you didn't even have like an in-game, you know, like you couldn't browse the web or anything with Steam. It was really just glorified chat at that point. And so we really took it to the next level. We were building with Adobe Air software, the environment and stuff. So it was really like this mixture of Flash and like, I don't know, all these weird technologies. And

BLD:
It was a monopoly and before Steve Jobs axed flash.

Zain:
And so, sorry, I'm kind of just going on this journey because you took me down this memory lane and, you know, Got Game became this like sort of cornerstone in my career because I was a pro gamer at that point. I was competing in Call of Duty for a few years and then Got Game really enabled me to go around the world and like compete. And so, you know, our founder, David Hua...

BLD: When you were a gaming intern at Got Game, were you paid to just play video games? Were you like an in-resident gamer?

Zain: No. Okay, so whoever had brought in interns to work on marketing and things like that, right? So I came in and I was like, hey, I'm a pro gamer. Let's figure this out. But as you know, you're trying to share your skills with people. People don't really figure out how you can leverage it, but we were really cornering this product idea in a space where gamers would use, like competitive gamers, maybe not pro, but esports was still somewhat in its infancy. And if we had built great tools for those gamers, I think we would have had something there, which we did, but yeah, we were in a weird position. This was before Twitch, right?

Justin Khan was working on Justin TV. And the big things here that were not happening was like, you know, people didn't have desktop computers weren't very common for young people. People weren't customizing computers like they do today. Like a lot of teens have light-up keyboards, mechanical keyboards and stuff. It's very different today. You look in a classroom today and there's a lot of nerds, but computers crossed the chasm outside of just nerds. When I was in high school, it was just you, like I was the only kid in school who built a computer. That was weird.

BLD: Yeah.

Zain: It's very different, right? And so, to be in a place where, hey, I'm this pro gamer, can we utilize my position here? Who was like, yeah, let's do it. And so it was like, let's sponsor you young kids who, we don't need much of a budget, right? So we just went around with our team. It was me and my buddy and my roommate, actually, Zach Packard. He was a pro World of Warcraft player. And so we basically were interns at Got Game and got to go to MLG tournaments. We helped build the pro circuits for MLG for World of Warcraft and Call of Duty. We brought PC gaming to MLG, me and Zach, which is funny, as interns, right?

BLD: Wait.

Zain: Eventually, I was hired as an employee, but I was still a junior type of career.

BLD: I mean, this sounds like the dream internship for any serious high school age or fresh out of high school.

Zain: We lived the dream, trust me, we lived the dream. We literally, I remember one day we drove from SF to San Diego for MLG San Diego, and we were gonna set up World of Warcraft for the first time. And I don't know if you guys are familiar with gaming stuff, but Astro Gaming, the headset company, they make the headsets and stuff.

BLD: Yeah, that's...

Zain: So we brought Astro headsets to PC gaming because at the time, PC gaming was really done over ventrilo, apps like that, latency issues with voice chat, right? They were done over servers. But Xbox gamers like Halo, competitive gamers, were using these Astro headsets to have purely LAN voice comms that were zero latency.

BLD: Man, LAN parties.

Zain: And that's how they were able to communicate in tournaments, right, on site. When we went to San Diego, the Astro company Astro Gaming was right behind Got Game's office in Soma. So we were like, "Hey, can we bring these headsets to MLG?" And they're like, "Yeah, let's do this PC gaming thing." So they gave us a bunch of headsets and I remember we set up our teams. We had Zach's teams for World of Warcraft and then my teams for Call of Duty. Yeah, these kids, like we set them up with the headsets and they had zero latency, whereas all the other kids had to connect to, I forget, but they were probably using maybe Ventrilo at the time, but they had to connect to an outside server from the MLG tournament just to communicate. So we had an advantage over these other teams. Anyways, this is the longest rant about this, but it was a crazy dream internship and building an MVP product for your friends. I was designing, and this wasn't just fun, right? It was enjoyable because I was doing something I love, but at that tournament, we were working. Then like, I was taking photos. We left, right? We had these crappy digital cameras back then. And we went back to the hotel, uploaded them to our Got Game blog or news site. We were the first ones to post about these World of Warcraft tournaments in the world. No one had the images. This was the first time these pro World of Warcraft players were meeting in person.

BLD: Is easy.

Zain: I had the photos of all the dopest gamers in the world that no one had, and we were getting all that traffic because of that. And then we came home, we'd be working on the app, and we'd be launching it to all our friends, all these competitive gamers that we were meeting on the circuits, and they were the ones testing the app. Eventually, Got Game didn't work out because of other reasons, but I feel like we were a little early, but we still had, we were inching our way to product-market fit. And it had a lot to do with because I was such a hardcore gamer that I was like, "Oh, I'm designing for these people." The term product designer didn't really exist, right? It's 2008, like it wasn't really like UI, UX. There was not really a thing like that. Even before UIUX, it was like information designer, information architect.

Zain: Yeah, exactly.

BLD: You?

Zain: Yeah.

BLD: work at...

Zain: or BlackBerry. Yeah. Wow.

Zain: Yeah, or you're sort of like an HTML like person. Like, that's...

BLD: Yeah.

Zain: it, right? You know, like ColdFusion or something, just weird stuff. So yeah, this is like a weird time where we were building an app. And honestly, Twitch popped up right after that, right? Justin and the team, like they pivoted to really focusing on live streaming and we had already focused on live streaming. We had acquired a company called GameV or something that did live streaming for Xbox. So we had owned a whole property that was doing all the live streaming for like Halo and stuff like that. And we were slowly branching into the web. It was one of those things where we were building everything. Like we built a sick in-game browser where you could browse while playing World of Warcraft and that was huge because people were using World of Warcraft tips and stuff like that. doing an arena, it's like, so just like a totally different world, but honestly, it's super fun because we built something dope, but it just didn't take off.

BLD: You know what's crazy is like this reminds me of when two examples come to mind. One, when I was watching, I was at an MLG tournament watching Brood War and like the expansion pack. And this guy, hot spotting had like more or less just came out and it was faster because it was on the next-gen telcos, it was faster than the arena's Wi-Fi for all the players. That difference in FPS totally makes a difference, especially for something like as twitchy as COD, right? Where it's like...

Zain: Right.

BLD: FPS totally matters. The second example that comes to mind is Wall Street getting information from like global exchanges milliseconds ahead of all the other competitions. So I would imagine that you guys were known for, "Okay, well these guys have top speed and like the most immersive experience." That's pretty wild to think about.

Zain: Yeah, yeah, it's a totally different time. I mean, I don't really game like that anymore, but yeah, those little things mattered so much. And that's honestly, like, I think what made competitive games so interesting back then was like those little weird things that added to why competition was so fun. It was because like, you know, Call of Duty competition was a very limited format of the real Call of Duty, right? Like they didn't have all the perks and stuff like that. You couldn't do all the cool stuff, extra things. Like it was very bare bones and it was to level the playing field. And then out of that, spawns like other weird things because people are glitching the map or they're finding ways to take advantage of what they have. It's understanding limitations and then going trying to go beyond that. And I love that because honestly, being a competitive gamer, I've derived so much from that experience. To me, one of the biggest things was about communication. You're a kid and you're yelling at each other. When you get to that level and so much money is on the line and you're traveling to a whole other city and your friends are not pulling their weight. Again...

BLD: Oh yeah.

Zain: you're just so young. There's a lot of toxicity in gaming. You don't know how to control those emotions. The teams you realize at the top, we're playing against evil genius and stuff like that. And these teams have such an incredible, impeccable stoicism about each individual. They're able to hold such a way about themselves during very intimidating moments or very extreme moments, right?

BLD: Yeah.

Zain: And you bring that into other spaces and all of a sudden, other things become a little bit easier. You're like, "Oh, we just have to communicate really well." Cool. You bring that to the startup world, and all of a sudden, it's like you communicate really well, and you can move really fast, right? So there's a lot of lessons I learned through that experience, and I think gaming, you know, again, it's coming on another hump again, right? We had the whole creator-streamer world, and now it's about to go over another...

BLD: Yeah.

Zain: big moment. So it's...

BLD: Well,

Zain: interesting.

BLD: so then, okay, so from Got Game, was it a straight line to Instacart?

Zain: No, so I worked at a... That was when the economy tanked and I was still in school. So I was basically taking night classes and trying to work, just paid my way through school. And I found through one of our investors, they invested in a company called Simraceway, which is a motorsport simulation gaming company. And again, I'm like, probably 20, not even 21 at this point, and I joined another gaming company. We were building this motorsport game that was supposed to be so real. It was supposed to be revolutionary, you know, like actually, you know, to the T where you feel like you're really driving the real car that when you go to drive the real car, it feels like it, besides the resistance and stuff.

That, like the key caveat, was for us to go and capitalize on betting, right? Like betting and gaming. So we wanted to basically do cash prize tournaments for motorsport because there was a huge niche market where motorsport fans love this so much and they spend a lot on these experiences. What we found was there's this crazy modding community online that loves these different simulation racing games and they would try to make them as accurate as possible. And they created their own tournaments online, just like any competitive game, right? We think about it like Call of Duty. The same thing happened. You have this small group who wants to play it competitively and they create their own version of it. Some people go and hack the game and they make this version that's meant for competitive, and then they create a league. It's never really officially the company that does it, right?

BLD: Yeah.

Zain: Yeah, for me, I was a really big Super Smash Bros. player, and basically, like, I don't know, maybe 30% of the second half of college for me was just playing a modded version of Brawl. Someone had figured out how to root Brawl, and they created Project M, which adapted the physics engine from Melee because the problem with Brawl on the Wii was just that the characters were too slippery, right? So you hit somebody and they would slide across the stage, whereas in Melee, they were just stickier. They had some gravity. And...

BLD: Right.

Zain: Yeah, it was like, I mean, it's so funny how these communities kind of deterministically almost like we have a shared interest, we have access to the internet. Okay, holy crap, I think I'm way better at this game than you are. Let's duke it out. And then suddenly tournaments form, and, you know, slowly shrines develop around legendary players and breakthroughs like wave dashing or frame skipping type stuff, you know.

Zain: Yeah, lobbying, exactly. None of this would exist without gamers actually having the ability to go and mod these things. Lobbying in Call of Duty and all these other games only came about because IRC existed and people would go into IRC and try to do pugs, right? Pickup games. They would try to go in, "I'm looking for a pickup game," and that's how you found a team. You would go and do a pickup game and you'd be a ringer for some other team, you know, their fifth man went to sleep because he's on the East Coast or he's in Europe or whatever, and you got his spot because you're on the West Coast and you're on dial-up, and that was your shot at trying to, like, maybe potentially get in with this team and eventually find your way into competing. But lobbying came about because there were way more casual gamers who had access to the game, right? Call of Duty and all these other games reached so many more people that now that marginal user who's like, "I kind of want to compete, but I suck," right? Like, most people pretty much suck, right? Like that top 1% is just absurd, right? The...

BLD: Right.

Zain: gap is so big. But when you're like, you know, this huge long tail of casual gamers who want to kind of compete with their friends, lobbying is genius, right? And it's addicting because it's just rapid fire. It's like a slot machine, and you're just sitting there getting randomized with other people, and it's fun. It's like a totally different online culture that most people never really experience.

Zain: Here's this steering wheel that we made with SteelSeries because I was sponsored by SteelSeries. And so this is the packaging I designed.

BLD: Wow. What's crazy is this is very analogous to today's like F1 tournaments. So there's Max Verstappen, who is incredible in real life, and then he's also ranked like number one or number two in the game. And it's like, okay, so they are a one-to-one transfer. Yeah. Yeah. Right. He's going to spank you on the track, and like, he's also going to spank you in the simulator. Yeah.

Zain: It's serious.

Zain: It's serious when you're racing with like these types of guys. Like it's yeah, it's real. And you realize it when like you're playing a game like that because it's so realistic. Whereas like, you know, in like a game like Call of Duty, it's just like, oh, this guy jumped off a building and like summersaulted.

BLD: I do really want to hear though about like Instacart and because you joined in like what December 2013, right?

Zain: Yep, yeah, I was like one of the first 10 employees.

Zain: Well, so from Simraceway, I joined Sincerely, which is Matt Bazzina's startup, and that's where Hua came back into my life, and he basically, no joke, he was on a scooter and would hover around our office outside of Simraceway, and he would yell my name to come outside because he wanted me to come work at Sincerely. And eventually, I joined. So Sincerely, we worked on a bunch of gifting apps. One was called Postergram, where you could send postcards of your Instagram photos in the mail and stuff like that. Sincerely got acquired. I worked there for a couple of years, and then Sincerely got acquired. That was my foray into iPhone apps, right? I was doing gaming stuff, but at this point, the apps were starting to launch, and basically, if you were a designer, you should be using a MacBook. It was like a moment where I had to reconcile with, I was like, oh man, I don't really...
I'm not into Macs like that, right?

BLD: Yeah.

Zain: And so I had to, I came into Sincerely, and the guys were looking at me like, who's this guy? What is that Samsung laptop? And I had to figure out how to design skeuomorphism stuff on a PC laptop with... This is funny, I'm sorry I'm saying this, but like, I don't... I'll get to the Instacart thing. Designing on a PC laptop, like a Samsung laptop, it was dope, but the screen, because my screen didn't match the MacBooks, and that's when Retina dropped, everyone was like, what's up with your designs? And so I'm over here like designing on a PC laptop, a Samsung laptop. It was dope, but the screen, because my screen didn't match the MacBooks, and that's when Retina dropped,

Zain: When I joined Instacart in 2013, I had to get a MacBook and started committing code. I was writing Rails and working on web apps. Sincerely got acquired by Pro Flowers, and I wanted to do something big. Max Mullin, one of the founders of Instacart, was introduced to me. We met at South Park, and I remember wearing a black hood even though it was unnecessary for the San Francisco summer. He made a joke about Drake, and we hit it off. The transition was smooth. He was familiar with my work and didn't need to see my portfolio. I did a design exercise. Sincerely focused on user actions like adding photos, messages, and addresses, while Instacart involved adding groceries and dealing with the complexity of a catalog. It made sense to me since my dad owned restaurants, and everyone eats.

BLD: Fun fact, before we even met you, Numi got into Y Combinator as an Instacart for Africa. We studied your work closely, doing screen-by-screen teardowns, paying attention to the little details. Most e-commerce apps required tapping into dedicated product details screens. Now, when you joined Instacart in 2013, what were the challenges they were facing, and how big was the team?

Zain: I was probably the ninth or tenth employee. Andrew Kane, Nick Elser, Min Kim, Arno Ferrari joined around the same time. I was the fourth in terms of product engineering. We had engineers like Brandon for Mac support, and Jason Yoon and Laura Barnum for customer support and operations. We had just launched in Chicago. The atmosphere at Instacart was focused and quiet. I was impressed by the team's intelligence. There was a dashboard on a TV with 10 to 20 orders. Instacart didn't have more than 50 orders a day at that time. We had recently raised an A round of funding.

BLD: Do you remember the first design challenge after the interview? What was it like?

Zain: Yeah, that's easy. The design challenge, I have it in my email. I remember creating an animated GIF for when you add an item to the cart on the web. It would appear in the top right, flow, and then animate away. I also cleaned up the cart and made the prices clear for the user. It was about making checkout crisp and simple, taking inspiration from Sincerely. When I joined, there was a delay in starting because of Thanksgiving. I was in Southern California visiting family, but Max wanted me to begin right away. He asked me to sync with Min, our iOS engineer who was working on the native iOS app. So I emailed Min with some ideas. It was early on, around the time Figma was just starting, so I started ideating.

BLD: Transitioning from Photoshop to Sketch, and then Sketch getting bloated.

Zain: Yeah, I was in a weird place. I knew Sketch but wasn't sure about trying a new tool since I was the only designer. So I sent Min designs, and he thought they looked good.

Zain: I was in a situation where I knew Sketch, and I wasn't sure if I wanted to try a new tool because I was the only designer here. So I sent Min some designs, and he was like, "Looks good to me."

BLD: Hehehe.

Zain: I was away, so I took a bus back to San Francisco because I like the affordable Mega Buses. Max suggested I should have flown back, emphasizing the value of my time. When I returned, Min had a version of the first design ready. I was impressed by his speed, and that's when I knew we could proceed.

BLD: As founders, it's a great feeling to see our employees get unblocked and inspired. From a designer's perspective, how did seeing your work live make you feel?

Zain: That's a good question. Seeing my work come to life was important to me because at Sincerely, we took pride in delivering excellence. I learned a lot from talented individuals like Rick Harrison, Matt Herzog, Harrison, Lee, Scott Gardner. We would walk around, go to bars, like Nob Hill, and closely examine design details on our phones, discussing things like what Path did. We were really immersed in the process.

Zain: And that level, I think sometimes gets lost. It's like, all right, but I think it's fun to obsess over those details, right? When you're creative, you're like, wow, that just feels so good. So taking that into Instacart, it wasn't just like, oh, I wanna get those feelings. But to meet Min was like, damn, I just met my guy. So to see him execute like that was like, all right, it's time to go.

BLD: Right.

Zain: To take that step back, before I came in, I saw an open playing field, right? The web app wasn't in great shape. All these things were just like, they weren't, they were undesigned, right? At that point, you didn't even have good frameworks or CSS frameworks or anything like that to jump off of that well, right? So everything was not in great shape, and so to me it was like, I could do so much, but Min was the key player at that moment for me because iOS had such a nice, you know, the way that it looks and feels, and then when you have someone who just really cares about those details, to put it in someone's hand, it's like, it shouldn't work like this, you can carry that now to everything else.

So seeing that work live was like, oh wow, now we can sell the vision. And so now we have the first version of what we think feels really amazing, you know, and that was like a game changer, period.

BLD: Wow, so I, okay, I really want to hear them because like you're so unique, I think, among designers and startup teammates that like, I think about this all the time, how most startups die before product-market fit. And that's usually where like, it's just like the wilderness period, you know, it's the founders trying to figure something out. And most hiring happens after product-market fit, right? Because it's like now, okay, we got it all together. We got to assemble a team to like really run with this thing that we found. So very, very few people actually get to see lift-off. Right? Um, it sounds like you got to see lift-off an Instacart. Like, what was that like? When did 50 become 5,000? Yeah. No, like what, what was that? What was

Zain: Oh man. You know. I think maybe Max or Apoorva might remember like 5,000 better than I do. I was so heads down that like it's such a blur right? Like when I was the only designer for like over a year and so at one point we had like 30, I swear it was like 30 engineers or something. I was just like, I was a sketch monster. I was just like, I don't care. Like, do I need to follow the engineers? No. Because why waste time? Like, why am I wasting time trying to pixel perfect our admin, you know, shit. I just sent Nick a bunch of styles real quick and boom, like here's our admin stuff for customer support and to manage all the shoppers and all these other things and catalog and like, cool, run it. At one point, like for years, like people had to use Inspect Element on their web browser just to see the rest of the navigation because that's how broken it was, but that's how much we were moving. We were like, it doesn't, it's like not that broken. You can use it, right? That's how fast we were moving. That's, I just wanted to give you that idea. So.

BLD: Wait, non-technical users would have to right click, inspect elements?

Zain: Yeah like customer support, yeah, they were like, yeah, so they would have to train other people and be like, you gotta inspect element and like, you know, make the thing like this and you'll be able to see these other links. It's like for a moment, right? But it was like, that's how, you know, it was like, we, you didn't have time to focus on all these things because we were building one of those multi-sided marketplaces that at that time, like you didn't have all these easy tools to spin up like an admin portal with a bunch of styles and stuff, right? So like, you know, the team was just hacking away on this stuff. And then we were moving forward. So my focus was iOS. What's the, what's like, you know, the priority of like, who's ordering the most on which platforms. It was like iOS web, you know, Android. And then in the middle of all that, it's like make the shopper stuff work well. So when I saw lift-off, it was really. Max came to me and he was like, Hey, we really need to bring in another designer. We're about to head to Burning Man, so can you talk to this guy before we leave? Because we probably will never talk to him again. And so I was like, all right, I'll talk to him.

And so that was, yeah, that was close to 2015, right? In 2015. Yeah. So, you know, the liftoff really was like, we, as we were watching cities, I think, I think for a lot of folks, it's like. It's maybe for some other products, it's like, oh my gosh, you know, like the thing goes up like crazy and there was moments like that at Instagram for sure. But like for a long time we were launching cities, right? We launched like Boston, we launched Chicago. We were launching like all these early cities like Miami, like Orange County, whatever, and a lot of that was like opening a spreadsheet and having all of the employees, you know, add their friends who live in those areas and like let's try and get some orders early on. And a lot of these cities didn't take off right early on.

Like we get some orders that first week, but then to build that habit with those users took a long time. So it was only until we really reached a lot more cities across the US is when that liftoff really started to happen. And a lot of this was coming from the Bay Area for a while. And then, obviously like New York and all these other places that really needed it, you were like, oh my gosh, like this is crazy. So. So I think it was really like, you know, towards the end of 2014, we were like, oh my gosh, this is like getting crazy. We moved it to a new office. And then that's when I was like, all right, like we're like doing work. And we had already raised more money between, you know, we'd raised another round.

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You know, we had raised our Series B in 2014 as well. So like, you know, that growth is happening. But like, when you think about like critical mass in terms of like, order growth and stuff, I feel like that was probably more like 2016-ish, and then more like 2018 or 19-ish, and then more like in the pandemic, right? It was when you probably see a lot of those hockey stick growth. When we turned on a lot of growth mechanics to launch a lot of cities in 2019 and stuff, to get to reach a lot of GMB goals, a lot of that took launching in new markets. Versus like, you know, I think those early days, it was like, how do you just make really great product in a space that no one else is really building in and do this really well, right? Get people fresh food delivered today.

BLD:
Yeah, it's so funny because it seems so obvious now, right? But I remember, like Max said to us, he was like, because we were able to connect with him before the batch started. And he said that when Instacart started, nobody in the grocery space, none of the incumbents had a digital strategy, right? And so a lot of Instacart's early days, building that traction was just... proving that this was going to be a market, whether the incumbents liked it or not, right? And that like there was, it was almost like building the table where the bargaining was going to happen rather

Zain:
Yeah,

BLD:
than, you know.

Zain:
that's exactly it. You know, that's why I think I was kind of ranting. There was like, I was trying to really find those moments and it honestly felt like an uphill battle a lot, you know, like as we talked to a poor bud and Neil, when they would come back from talking with retailers, like they, these weren't easy yeses getting partnerships, right? Like whole foods was our first one. And that happened way later in 2014. And I remember designing the fridge in the garage in South park. And we will literally wield it over to fourth and Folsom or Harrison or whatever it is. Um, I literally lived a block from that whole food. So like, I would go and see it like all the time. And,

BLD:
Yeah

Zain:
um, and yeah, so I think, you know, those moments, it was like, whole foods was our like saving grace for that bit. They were like our best friend and like, we did all this fun marketing and like, I learned how to take over stores, like how to design, no one was doing any marketing, right? There was no marketing person at Instacart. I was doing all of Instacart's brand design and marketing. There was no paid ads or anything for years. And so it was all just me doing a ton of in-store material. I would just go and ship tons of stuff while I was designing the apps and all that. And I would send out all these print materials to the stores, huge posters. And it was just all about like groceries delivered an hour and the phone and like, you know. the refrigerator wraps and stuff like that, and we just turned stores like green, and there's just like put the Instacart brand everywhere. So once you just had that like in all these cities, what's that?

BLD: sounds like, I was just going to say it just like hearing you talk about it. It just sounds like Instacart very early on was able to create a culture of like a hive mentality. Whereas I think a lot of maybe like good companies, not great ones, good companies don't have access to that because they didn't create access to that. It sounds like you were very much someone, the entire team really. was coming to each other with things to do and collaborating and co-elevating versus it being, I mean, maybe it was, you tell me, but it doesn't sound like it was very, okay, we're gonna be working on this, this and this. I think like it sounds like maybe there's like large swaths of that, but it does sound like it was everyone being like, okay, we've identified these, these, these, like, this is what we're gonna get done for this week. Like, how was that Creole, that, that, that, culture created. You know, if you're talking to a founder and they're asking that, how do you create that culture?

Zain: Yeah, how do you create that culture of like building and knowing just like what to work on or trying things? Is that kind of--

BLD: And like the founders being able to say to like you Zane and like another teammate, like y'all go figure this out. Like either we have to go to Burning Man or we have to go like close like the series B Investor, whatever it is, rather than like sort of the food being pre-chewed, the direction being given to you. And then you like having to work within these boxed in constraints.

Zain: Yeah, you know, the interesting thing here was like, I sat between Min and Max, they called me like mean, average, it's like, you know, it's funny. And so standing that close to them, we were shipping so fast. Max and I were shipping code edits, Min was shipping the iPhone app. That iterative process allowed us to share data easily. I'd look to the right and Max would show me what's happening in terms of conversion. We would even go to the grocery store and buy people groceries, find moms and buy them groceries to test the app. Max and Matt Brazina pushed me to do research in person, talk to people. It was uncomfortable, but I enjoy being in uncomfortable situations, so let's do it. And I did that for a long time. Over six years, I talked to thousands of customers, visited their homes, even filmed their homes and children. It was intense, but it's necessary to deeply understand your customers and users.

Well, that DNA, when you have it in different people or as cornerstones in the company, it's like people are rooted in that understanding of work. When you reach a stage of growth, Max and I worked on the roadmap and added ideas to it. Let me give you an example. We worked on Listen Recipes. I remember designing a full-fledged feature while I was at Coachella, working on music stuff outside of work. We were on tour with A-Track, and I was helping out with little things like duckbills and giving them out to people in the crowd. During Coachella weekend, I thought it would be cool to have a list of things A-Track had for Coachella that he could tweet, like a Coachella kit with items such as Hot Cheetos and Dom Perignon. It was more of a gut instinct and not backed by thorough research. However, we built the entire feature with Arno, including the ability to create lists and recipes, embed them in modules, and have cover photos. If you shopped in a different zip code, it would pull the ingredients from that store.

And Min built the feature on iOS, and we built the entire thing, but unfortunately, no one used it. We also didn't market features to users during my entire time there, which had its pros and cons. It allowed us to learn what features users naturally gravitated towards, but it also meant that well-designed features like Listen Recipes didn't get the attention they deserved. If a feature lacks the right content or isn't executed perfectly, it simply doesn't work. We ended up wasting a lot of engineering time on those lessons, which was especially challenging when we were competing for orders on a smaller scale, not in the thousands or hundreds of millions. We couldn't afford to make sacrifices like that.

BLD: Yeah, I remember those collaborations and the ability to add items to Instacart directly from the app. It was impressive to see everything appear in my cart instantly. And you're right about the Lyft story and Evan's insights. Being close to the customer was crucial for their success. We actually did something similar at NUMI. We chose an office in a building with a grocery store so that we could personally pick the groceries and interact with customers in the parking lot. We would even put the groceries in their pantries. It's intense, but it's true that being close to the customer is important. When you have conversations with your team, you start realizing that junior designers begin sentences with "I think," while senior designers start with "it should be" because they have firsthand experiences with customers or insights from Max's dashboard.

BLD: Yeah, absolutely. Being close to the customer is crucial, especially in a physical experience like grocery delivery. If you're designing in an office without actually experiencing the process of receiving groceries, you might miss important details. I remember relying on my mom for feedback in the early days of Instacart. She would test the app and give me feedback, like saying the font was too small and she couldn't read it without her glasses. It was a wake-up call for me, realizing that I needed to design for a user I hadn't fully understood before.

Zain:
Yeah. No, I love that. It's being that close is so important, especially like a physical type of experience, right? You, if you're just designing in an office and you're not realizing what it's like to actually receive the groceries, especially like that young, right? I wasn't cooking at home. I was eating at work all the time. So I wasn't using the product at home. So I'd have to use it at work or like, you know, wherever I was on trips or I was always on the phone with my mom, like those early days at Instacart. My mom was literally my UI tests, like she would tell me the font's too small. That was one of the first weeks of Instacart, she was like, yeah, I can't read that. She had put on her glasses and I was like, oh my gosh, I've been designing all wrong this whole time, right? Like a lot of the stuff I've learned at this point is unraveling before my eyes because I was designing for a whole new user that I've never truly understood.

BLD:
Right.

Zain:
That like, hey, technology has to work for them in a totally different way for this very utilitarian experience. And I'm over here trying to connect this to a very personal, cultural experience because it's food and all these things. And so that I was like, dang, we have to really solve this piece, which is like these pain points, right? And reduce all of those barriers for entry. And so you have to really be with that person. And that means talking to people who are disabled, talking to moms who are pregnant or who have three kids or running around, but they're screaming and stuff. Like it's intense when you experience that yourself and you go, oh my gosh, I've been sitting in an office in Soma on the 11th floor designing for like, you know, Gen Z millennials, whatever, who've been using iPhone since like iPhone one, right? Like that's crazy.

BLD:
Yeah.

Zain:
We're crazy if you think that's the way you should design.

BLD:
So then I'm talking about designing for a new persona. I mean, you joined YC right around the time that we did. You know, we were gearing up for the Winter 20 batch, and I think that's around the time that you came into YC's design function. And I'm just so curious to hear about what was that mental model shift? And I mean, going through, for us, we were the guinea pigs of, I think, a lot of the stuff that you were shipping, because the Winter 20 batch, I always like to describe it as the last in-person YC batch and the first remote YC batch, right? That they had to kind of shift that model in the middle because of COVID. So like, yeah, what was it like coming into YC's design function at that specific moment?

Zain:
Wild.

Zain:
Honestly, I had such an idea of what YC was because all my friends had been in YC, right? All the founders had worked with the end of YC. I helped Whoa and Meadow get into YC, working on some of the early Meadow design stuff. So being along these rides and working with different people, I mean, we had all the YC people come and talk at Instacart, from Paul Graham to Sam Altman and many other folks. So there's this affinity I had for YC, but it never really felt like this place because I didn't see the design there like that. Then an opportunity came up. YC had thought YC should have a product designer, and I thought it looked really interesting.

BLD:
Right.

Zain:
Everyone I know is familiar with Justin Khan and Michael Seibel. So I thought, this feels like I should try this. I want to do something new. Instacart already had over 3000 employees. It took us over eight months to redesign some stuff in the app. So I thought, okay, I need a faster pace and want to do something new. Instacart had its ups and downs, so YC was one of those things where I thought, cool, I get to work at a small company and it's gonna feel early, but it's YC, so it's different. I'll work with founders and learn more about investing and startups. I love startups. I've been working on a bunch of startups, so why not? Let me help founders design companies and stuff. Getting in was a totally different experience. The first experience was in Mountain View, meeting founders and realizing how much Instacart had impacted people across the world. People in Africa were like, "Oh my God, you worked on Instacart? That's crazy." And I didn't realize that. I'd been heads down for like six years. I was like, "Oh, people actually like it." This guy was telling me they were studying Instacart in their MBA program. I was like, "Are we old? Is this a compliment?" But there was this moment of like, "Oh wow, this is sort of a homecoming. Now I get to go and share and empower." And that's all it was, empowering the founders at YC to build amazing companies. That became the cornerstone of all the work.

BLD:
So when we think about designing for a product, it's usually very clear who the customer is. When it's YC, the customer is the founder. It's a very different design dynamic, right? Were you going out, just like you did at Instacart, talking to founders and finding out what they needed that design could solve? Or were there already... like was there already a list of things that needed to be solved that the team that brought you in had arrived at?

Zain:
That's a great question. I'll break this into two. There's absolutely a bunch of stuff on the table at YC to do, and then there was a bunch of stuff I saw that was like, "Oh my gosh, there's a whole missing piece of the puzzle here." I think there's also a third piece here, which is like, what's the appetite that founders have for this experience in their lives? So if that makes any sense. What you're talking about is this is not an add-to-cart product.

Zain:
I'm not coming into YC and people are not adding a fundraise to cart, right? So that broke my brain. I was like, what's our metric for success? How do I improve this stuff? What does it mean to really improve software? A lot of designers and people outside of the ecosystem looked at me and said, "You have my dream job, or that's my dream job," because they thought I was like a one-man agency designing all the startups in the world. But the reality was, that's not it. The reality was, I needed to come into YC and empower the startups without helping them with any pixels. Do this job without touching any design for the founders.

Zain:
And that was like, uh, okay. So I can't tell these guys, I can't tell Harrison, "Hey, maybe you should try this different type of thing." What version of that can I give? That's not going to be so invasive where you're going to rely on me for help or think that you need a Zain or think that you can't do this on your own. How do I actually open your world up to design and how do I empower you through design to make your life easier? And that... Oh sorry, go ahead.

BLD:
All right, real quick, this is a very nuanced and subtle thing that you're describing, but it's so important. I want to make sure I'm understanding it correctly. Are you saying that your mandate at YC was to almost like awaken these founders to design rather than necessarily being the designer on YC products? I know you did some of that as well, but like...

Zain:
I would say, if you talk to Gustav or something, they probably told me not to do this in a big way, which was like software scales, right? This is a YC way. It's like software scales. So if we have the least amount of people working on software that we can scale really well and it's really helping founders' lives, great. You're doing a great job. Then you can maybe talk to them a little bit about design. To me, it was twofold. It was a revolving door. My work is going to be a reflection of how founders feel they should be designing. If I go and design a beautiful Book Face, which is an internal YC app, if we design a beautiful BookFace, our founders are gonna be like, "Wow, BookFace is beautiful. I gotta design a beautiful product." Or are they gonna feel like, "Wow, BookFace is really hacky. The search actually works really well, maybe we should just learn from this search experience. Everything else sucks though. So why is that good?" So there's this weird give and take where a lot of that work, again, coming back to when I was at Instacart, was giving designs to engineers and not really trying to get to pixel perfection. I remember we shipped a big modal that had the headline smaller than the body copy and we didn't touch it for years. It was the share, it was how you invited your friends, so that was the first thing people saw when they got invited. So similarly at YC, it was like, "Dang, I wanna go and redesign something, but what's really broken here?" And on BookFace, it was maybe like, search results are taking 10 seconds to load. So you could go and design a whole new search results experience, but what good does that do if it's taking 10 seconds to load? So here's the metric: we're trying to save founders time. How do you save founders time so that they can focus on their company?

BLD:
You know, one of the things that I remember, when I first heard about you, it was through the post. And then when I first learned from you, it was in the knowledge manual where you talked about how to find designers, price ranges, when you're getting the runaround, bullshit to avoid. And I was like, holy cow, just with this one post, this guy has been able to touch so many founders' lives. What other examples like that were you helping founders come into the design discipline and understand its benefits and how to navigate it?

Zain:
Yeah, what were the other things that really empowered the founders?

That's a great question. And I have to go back to what you also asked, which was... I had a revolving door with founders in terms of user research, right? So like, I knew that in order to do this, I don't know founders in Nairobi, I don't know founders in the Middle East, North Africa, Southeast Asia, Europe. I'm Pakistani, but I was born in Los Angeles. I only know my home country so well. Just those cultural differences alone break down what you understand about design. Design is extremely colonized, right? The way we look at fonts and aesthetics, it's very Eurocentric. Going into the human language, a lot of people feel like they have to design like these companies in Silicon Valley. But when people are designing products in these other countries, they need to know that maybe Airbnb is not the example. So as a designer, when it comes to speaking a design gospel, you gotta watch what you say.

I remember a moment of humility I had when working with some founders. They were building an app for women, an e-commerce app for secondhand women's wear. We were doing a talk, and they were asking me for feedback. I was giving them feedback, and I think some of my feedback was a little suggestive. I was like, "Hey, maybe you should be a little prescriptive and have better photos, higher quality photos, maybe that might make your customers want to buy this product more, or maybe you should help them sort by colors." I said something that was very prescriptive. The founder called me out and said, "Hey, I just want to let you know, you're kind of telling me what we should do instead of suggesting or asking why we chose to make this decision this way." And I was like, "Oh my gosh." She crushed me because I did the wrong thing. I was being a little too suggestive about what they should do. I realized I need to start from first principles and reframe how I talk to founders.

Writing design stuff for the knowledge base was such a big learning experience. Founders came to me and asked for help with hiring designers, figuring out salaries, and I got so many of these questions. I wanted to give advice in a scalable way, not just one-on-one. I wanted to share answers to these questions that work across the world. That's why I thought Book Face was a great place to invest. I wanted to elevate some of these answers that may not be easily found in the knowledge base. I wanted founders to have their own ways to comment and share their experiences. That's how you save founders time and make their lives easier, so they can focus on their company. It's about getting access to knowledge faster, getting answers faster, and allowing founders to go back and work on their business.

Zain:
And it's such a weird metric to design for because sometimes it's like, dude, I don't think I need to design a mock for this. It's already a broken experience, or maybe they don't need to do this at all. Maybe we just need to automate it or send this thing to the founders. So a lot of it was grunt work and trying to figure out how we get more data on companies and founders to better serve them. It's about creating a network effect within the YC ecosystem, where the more information and interaction we have, the better we can support founders.

BLD:
Totally.

Zain:
That's the fundamental difference for that product.

BLD:
Right. Yeah, it's like designing for the mentality, the thought process behind why certain things work the way they do.

Zain:
Yeah, exactly. Michael Seibel was great at questioning why we were trying to build certain things. Always questioning and starting from first principles. Is this really going to help our founders? He would ask me, "Zain, why do you really want to build tools for investors? Is that really going to help our founders? Could we be focusing on something else?" To me, I wanted to bring these worlds together, investors and founders on YC. I didn't want it to be a walled space. I thought there should be something connecting everyone. I wanted them to interact and share ideas. That's how you break old ways of thinking and illuminate new ideas. Release the library to everyone, democratize startup knowledge. Don't think ill of your users. Give them access and see what they do with it. It's like the example with Facebook's AI, people just ran with it.

BLD:
Yeah.

Zain:
So it's about trusting and empowering the users.

BLD:
They did, yeah. And so I actually want to shift gears here to talk about Nature's Keeper. What's the pitch? I know this is post YC, what's the vision behind it? Where are you trying to take it?

Zain:
Yeah, Nature's Keeper is all about sustainability. Gustav was a big advocate for climate change and investing in climate change companies, and that had a big impact on me. Nature's Keeper is born out of my inability to be an amazing engineer and build a tech startup. But I've always had an affinity for clothes. At YC, I made all the swag for Instacart and my own clothing companies. I wanted to do my hobbies in a more sustainable fashion. Buying new products is cool, fun. I'm a gear head. We all love showing off our new things. But being outdoors, snowboarding, and traveling have always brought me closer to myself and nature. I've seen firsthand what's been happening in San Francisco and Tahoe. For me, it's about experimenting and creating sustainable gear. I started with handmade outdoor gear, like this backcountry pack I made with guidance from John Campbell, a legendary pack maker. It has pockets and space for avalanche gear.

BLD:
Oh, wow. Oh.

Zain:
Yeah.

BLD:
Yeah. You know what?

Zain:
This is serious business.

BLD:
That reminds me a lot of the Yeti Backpack series. They entered into this space with not a whole lot of knowledge. You can always tell when a company just cares. When they come out with a bang, it's like, wow, you did your diligence. You spoke to outdoor enthusiasts, and you produce this product and it shows.

BLD:
I don't know. It's very similar with you as well. What was that process like doing diligence? Was it looking inward because you have an affinity for the outdoors, or who was it that you spoke to outside?

Zain:
Good question. Like I said, Nature's Keeper was born out of wanting to create my own stuff. Let me take you back. My friend Julian Dash is one of the best denim designers in the world. He's made jackets for Wu Tang, Kevin Durant, Steph Curry, Angel Yee, Eric Obadiw, Young Thug, and others. He's based in downtown SF, and we've been friends for around 15 years. He had a studio where he taught young kids in SF how to create their own denim and become entrepreneurs. After working at Instacart, I would visit his studio and observe. I always carried a DSLR camera with me and used messenger bags while biking. That's where the idea of utility and gear started for me. I traveled for Instacart, capturing photos of shoppers, customers, and our team in different cities. It was about the utility aspect. No one really asks about this stuff. Julian understood it from a design perspective. I would arrive at his studio on Turk Street, late at night. We would hang out, eat, have beers, and I would watch him make denim while filming. He made me one of my favorite pairs without even needing many measurements. He just knew by looking at me. He considered the fact that I go to protests and jump barricades for photos. He understood my Instacart work and how I wanted to look. These little cultural details he understood.

Zain:
Yeah. So, those intimate details are important as a designer. Product design includes UI, hardware, and clothing. Julian always emphasized clothing, food, and shelter. His company, Holy Stitch, focuses on teaching people to cook, make their own clothing, and build shelter. That stuck with me. I've had crazy experiences in the wilderness, like being in an avalanche and a car accident. So, Nature's Keeper is all about handmade sustainable outdoor gear for backcountry skiers and snowboarders. I'm starting with snow sports, but I also want to make dry bags for kayaking and paddleboarding. I experiment with sewing machines at home and collaborate with people who share a passion for the environment, like my friend Mike Emmett, who cleans up rivers. I want to blend the worlds of elite athletes and environmental stewardship while adding my own spin influenced by hip hop. Handmade products with a funky style.

BLD:
Yo, that's amazing, Zain. Thank you so much. This was a really incredible conversation.

Zain:
For sure, guys. I appreciate it. This was super fun. I appreciate your questions and reminiscing about the old days at Instacart. Glad we got to do this.

BLD:
Hopefully founders and designers can learn from you. Thank you, Zain. I'm Harrison. I'm Agree. This has been Bottom Line Design with Zain. Thank you so much.