Ryan Olson grew from mid-level engineer (IC4) to a principal engineer (IC8) at Instagram through a series of famous projects. The most notable was when he was the lead iOS developer that built Instagram Stories. We discuss his career journey and learnings.
Check out the episode wherever you get your podcasts: YouTube, Spotify, Apple Podcasts.
Timestamps
00:00:31 - Failing his FB interview
00:03:27 - Interning /w future billionaires
00:14:08 - Interview nerves tip
00:16:37 - Early Instagram experiences
00:34:08 - Building Instagram Stories
00:45:03 - 1 promo per half to Staff (IC6)
00:49:51 - Senior staff promo project (IC7)
00:57:37 - IG labs & his principal promo (IC8)
01:08:19 - Starting Retro and leaving big tech
01:21:33 - Small teams hypothetical
01:25:17 - Examples of talented individuals
01:31:16 - Advice to his younger self
Transcript
00:00:31 — Failing his FB interview
Ryan Peterman:
[00:00:48] in 2011, I understand that you interviewed for Facebook and you failed. Can you talk through that experience and what that was like?
Ryan Olson:
[00:00:57] I thought Facebook was super cool at the time. I wanted it so bad, and I was just incredibly nervous. I remember the interviewer, he kind of asked the question.
[00:01:10] He’s like, oh, you can just do it on my machine. He turned around, his laptop, pushed it over to me. I put my hands on the keyboard. You could actually hear the keys rattling because I was shaking so bad, which starts this feedback loop. Heart’s pounding. The question that he asked was actually one that ended up getting banned at Facebook, which I feel somewhat better about.
[00:01:36] But what was the question? It was this Gram buckets question, which there’s a very simple solution if you know data structures, where I use a dictionary. That solution didn’t come to me, so I wrote this horrendous triple nested for loop. The interview went quite poorly and he actually cut the interview short, which as an interviewer, that’s something I would never do.
[00:02:06] Even if somebody’s failing, you want to try to have a good candidate experience. He cut it short and he was just like, look, you’re just not gonna be able to make it at Facebook, which was like a knife to the heart. I wanted this thing so bad, and then this guy was just like, yeah, you’re just not good enough for this.
[00:02:28] It took me a while to bounce back after that. Luckily I did bounce back. I feel like I had a pretty good career at Facebook, so I managed to prove him wrong. I never got the name of the interviewer.
Ryan Peterman:
[00:02:49] Well, I mean, that to me shows how broken the interview process is. If you’re an incredibly high performer, and if you are not getting through, then clearly it’s not testing for the right things.
Ryan Olson:
[00:03:05] Yeah, I’ve always struggled with the Leetcode style interview. It was something I was always interested in trying to change while at Facebook, but it’s the interview process.
[00:03:17] There is such a machine across a big company. One of the things I enjoy about having my own company is I don’t have to do those things that I don’t agree with.
00:03:27 — Interning /w future billionaires
Ryan Peterman:
[00:03:28] After failing that Facebook interview, I understand that you went to work at a startup named Flipboard.
[00:03:33] And you were an intern, one of four interns. What was that experience like working at Flipboard?
Ryan Olson:
[00:03:39] Yeah, so I’ll tell a little bit more of the in-between story there. A couple months after the Facebook interview, I interviewed with Amazon. It was a phone interview, so I was actually a lot more comfortable.
[00:03:55] I did well on that. I got the offer. They did the kind of exploding offer. I got a call on Friday. It was like, you need to tell us by Monday if you’re taking this or not. I was pre-prepared to take it. It seemed like a cool opportunity. I had an investor friend. He founded Insight Partners, which is one of the big venture firms.
[00:04:20] He had mentioned at some point in the past, he’s like, at some point maybe I’ll connect you with some startups. I reached out to him and I said, Hey, I got this intern offer at Amazon. I think I’m gonna take it. He was like, don’t take it yet, let me connect you with some startup people.
[00:04:40] It was on a Sunday and he sent an email connecting me with the co-founder of Flipboard, Evan Dahl. Evan called me right away. I didn’t really wanna pick up the phone because I didn’t wanna do another interview and kind of just wanted to take this job offer that I had.
[00:05:02] I’m very glad I picked up the phone and had a great conversation with Evan. He had worked at Apple on the core of iOS. He actually wrote UIViewController, which is the core UI class that you interact with. He’d also taught this course at Stanford, called CS 193P, which they made available on iTunes.
[00:05:29] That was how I learned iOS development. I took it a different year that Evan didn’t teach. We had a really good conversation about that. After that phone call, I was like, yeah, okay, this makes sense. This seems way more interesting than whatever I’m gonna do at Amazon.
[00:05:47] I went there in the summer and the company was about 50 people at that time. We had maybe four interns or so. It was an extremely high density of talent. People were all super smart. They’d come from backgrounds like writing the iOS frameworks at Apple.
[00:06:15] One of the other interns that I sat next to, he wasn’t really an intern. He had worked at Apple and he was actually doing a medical degree and just needed a job for the summer. He was friends with Evan. He had written the push notifications framework and was talking about how he set that up for the demo at WWDC, running off his Mac Mini in Moscone where they had the conference.
[00:06:42] Another story he told was he had written the clock framework, and they had a bad time zone bug one year around New Year’s or something, and they screwed up and people’s alarms didn’t go off. It was fairly catastrophic.
[00:07:03] Making sure people’s alarms go off is pretty important. It was just a really good learning environment and I learned a ton about iOS and about building product. Two of the other interns have gone on to make multi-billion dollar companies. One is Dylan Field, who founded Figma, which went public yesterday.
[00:07:30] I think it’s a $50 billion market cap today. He was an intern through the first half of the summer that I was there. He ended his internship and founded Figma.
[00:07:57] I actually really questioned whether I should go back to finish my last year of school. I’m ultimately glad that I did, but it felt like there was just this moment happening. I was like, I can’t leave. If I go back to school, I’m gonna miss out on something really critical.
Ryan Peterman:
[00:08:08] So Dylan Field, co-founder of Figma, is one of the interns, and I saw in your writing, the other intern was Devin Finzer, founder of OpenSea, which at some point was a billion dollar company.
[00:08:22] I don’t know the exact valuation now, but that is absurd. Were there any traits that you noticed in those people or that intern class that kind of foreshadowed that they would be that successful?
Ryan Olson:
[00:08:33] They were definitely determined to start companies. That was what they wanted to do.
[00:08:39] I think that was a bit different than what I saw from my university classmates. People just wanted to get a job, kind of like the highest aspiration was to work at a big tech company. Both Devin and Dylan were like, we wanna start companies and there was a lot of talk about ideas and what they would do.
[00:09:03] It’s interesting to think back to the early days of Figma or talking to Dylan around that time. The idea that they had, they weren’t totally landed on the idea, but they had this one really interesting insight, which was WebGL was this new technology that was really gonna enable new things on the web.
[00:09:27] Dylan’s co-founder, Evan, was a really talented engineer and was very early to WebGL and very skilled at that. I think they went through some different iterations of the product that weren’t really tailored toward designers at all. Dylan talked about how they were a meme generator app for a week or something like that.
[00:09:48] It took them a bit to find their use case and customer base. They had this vision of like, this technology is really gonna change things. They stuck with that. It’s cool to see how far they came.
Ryan Peterman:
[00:10:06] It seems like while you were working at Flipboard, you built a successful open source project. Some of the first commits are in 2014. I’m curious, what’s the story behind that and why’d you open source that?
Ryan Olson:
[00:10:18] So during my internship I did some work on internal debugging tools for our iOS app. It was the first time I’d really worked deeply in Objective-C, and I found the language really interesting because it’s a compiled language, but it has this dynamic aspect, has this runtime that exposes quite a bit of information.
[00:10:46] While the app is running, you can inspect a lot of things about what are the classes, what are the methods on those classes. You can call them dynamically. You can see all the state, all the properties. The first iteration of that was just building a tool to inspect the state of the app and tweak it.
[00:11:07] I think we called it Tweak. It was FLTweaker. I just continued iterating on that as a side project. My main focus was building Flipboard, building the app, building new features.
[00:11:31] It was kind of like a nights and weekends thing that I was working on this debugging tool. People in the company found it really useful. It was a way to understand what was going on in the app under the hood. You could see all the network requests, you could see what was on the file system.
[00:11:50] I asked, “Hey, can I open source this? I think it’s going to be useful for other people.” Everyone was on board with that, so we pushed it out. It’s become one of the more popular iOS debugging tools. A lot of apps use it. It’s definitely used at Facebook and Instagram. It was also cool to see it take on a life of its own. I’ve been less active as a maintainer of it in the past probably since I started Instagram, or maybe a couple years into that. But this guy, Tanner, really took it over and has continued evolving it and adding features.
Ryan Peterman:
[00:12:33] That’s awesome. I remember hearing about Flex at Instagram as well, so I wasn’t aware that that was actually something you built before you were at the company, which is really cool. I’m curious, did building something like that and open sourcing it have some unexpected butterfly effect on your career in some way?
Ryan Olson:
[00:12:49] In some ways it did. In some ways I thought maybe it would have more impact than it did. An example of that is when I came to interview at Instagram, I had already released this open source and I was like, “Here’s my code. You want to see what I can do? This is a thing that I built that you can go look at.”
[00:13:13] None of my interviewers had any interest in looking at it. They were like, “We want to know if you can do this phone number sorting thing.” That was pretty frustrating to me. I was like, “You can see my work here, and you’re choosing not to look at it.”
[00:13:29] Other people who were slightly outside of the interview loop, but part of the recruiting process, like Jonathan Dan, who worked at Facebook on the iOS team, he got me to interview in the first place. That was all through him seeing this tool and what it could do. I think he advocated in the candidate review because I had a mixed interview loop.
00:14:08 - Interview nerves tip
Ryan Olson:
[00:14:14] I was very nervous in my internship interview. I did something for my full-time interview that might be helpful to some people out there who get nervous in interview situations. There’s something called beta blockers, which block adrenaline. When you have the physical effects of being nervous, like a pounding heart or sweaty palms, it can create a feedback loop that spirals down and blocks your performance.
[00:14:50] A beta blocker stops that adrenaline from firing, so you can stay calm and not end up in that spiral. I got a prescription for that for my interview, interview performance-enhancing drugs, I guess. I took that, and it was very helpful for me, so I was able to stay calm.
[00:15:13] I think performers sometimes use this, like comedians, to stay themselves and not end up in this nervous loop. I was still in a coding style interview loop, which I don’t do that well at. I think I had a few absolute confidence hire interviews and probably a few no hires. Somehow I managed to get through.
[00:16:04] I came into Facebook as an IC4, one level up from new grad engineer. I would say I was under-leveled as a hire. Part of that came from my interview loop.
Ryan Peterman:
[00:16:06] I’m curious, when you used the beta blockers, did it completely remove the nerves component for you, or did it just help a little bit?
Ryan Olson:
[00:16:13] I’ve only used them a handful of times, but pretty much completely, you know, like no noticeable nervous effects. I think you can still be in your head about what you’re saying, but it takes away a lot of those physical effects.
[00:16:32] No pounding heart or sweating, that type of thing.
00:16:37 — Early Instagram experiences
Ryan Peterman:
[00:16:37] After you passed the interview for full time, you started working on the Instagram team, working on iOS, and I’m curious what the environment was like at the time. What was the size of the team?
Ryan Olson:
[00:16:51] I came in and I think there were about 10 iOS engineers working on Instagram then. The team size had come down. The way the story’s been told to me is there were maybe about 20 iOS engineers, and there was kind of this internal war over the direction of the codebase, like the infrastructure, how the Instagram iOS app would be built.
[00:17:35] There was a really talented iOS engineer, Scott Goodson, who was managing the team, and he had made this framework for the Facebook Paper app called AsyncDisplayKit. It was kind of a different approach to how you manage writing iOS. There were warring factions; some people were very pro AsyncDisplayKit, while others were like, “No, we should just stick to vanilla iOS, how Apple builds apps.”
[00:18:01] The way it was told to me is these two factions fought each other, and each side destroyed each other. Everyone just left, and nobody won. I came into this team. Not many engineers had been there more than six months to a year, so it was a pretty new team.
[00:18:28] Because of that, there was a lot of low-hanging fruit, a lot of places to have impact. One of the first things I did was put the app into a tool called the Time Profiler. Most iOS developers will know this in Xcode or in Instruments. I looked at what was happening on cold start.
[00:18:53] There was a bunch in the startup path for the profile tab, which many people will never tap into. If they do, you can do that work at that time. It was a very easy win to shave 20% off our cold start time just by deferring that work until later.
[00:19:16] Another example was we had this networking library, AFNetworking. Most programmers are familiar with assertions. In iOS, assertions are typically handled in debug mode to crash and alert you to a problem, but you have fallback behavior for production, and you don’t actually crash the app.
[00:19:46] This networking library was built with assertions on, and it was crashing the app for benign failures, like a network failure, where the app could recover. We were just crashing. That cut our crash rate by 80%. It was just a one-line change, NSBlockAssertions, but it had a significant impact on the functioning of the app.
[00:20:10] Instagram had this cool tradition where every week they would give what was called the ax. It wasn’t getting fired, which sounds like if you got the ax, you did something of outsized impact. It was actually across all functions; it didn’t have to be engineering, could be product design, whatever. For that 80% crash reduction, I won the ax.
[00:20:32] It was this big physical ax that you got to carry around for a week. At first, I thought I got to take it home, but I realized there was just one ax. Somebody else was going to get it next week.
[00:20:41] Yeah, I had it at my desk for a week, and I was like, “Oh no, there’s just one ax. Somebody else is going to get it next week.”
Ryan Peterman:
[00:20:48] I remember the ax. What’s the story behind that?
Ryan Olson:
[00:20:51] that something that Instagram founders had done? At some point they had been asked by GQ or some men’s magazine to do a holiday gift guide, and they just kind of came up with random gifts. One of them was they found this service that was making bespoke axes. You could get this ax and then one of their investors read that article. They sent them this huge ax. Facebook security was pretty unhappy about this weapon in the office, so they made them put it on a plaque. It was mounted to the plaque. You couldn’t take it off. It was a cool tradition. Later, in my time there, they ended the ax as a very intentional thing. They thought people were feeling excluded because it was a weapon that was being given. I was kind of sad when that happened because it felt like, at that time, the founders were gone and it was a piece of early Instagram culture that they were kind of sweeping under the rug.
Ryan Peterman:
[00:22:02] So I guess going into your first major project, after all those low-hanging fruit, I understand there was a big redesign of the Instagram app called Whiteout. Can you talk about the story behind that project?
Ryan Olson:
[00:22:14] Yeah. It was a couple months into my time there and I got word that we were working on a new icon, which ended up being very controversial. As part of that, we were going to do a redesign of the app, a big visual refresh. I don’t remember exactly what I did, but I remember being like, I have to work on this thing. This sounds so cool. This is what I want to do. I told my manager, I was meeting the designers that were working on it. I basically just maneuvered myself in to work on this project. The main designer on it, Joy Vincent, was just an incredible talent and the nicest guy ever. Really sad, he passed away while we were at Instagram. I sat in a war room, a conference room basically, with him for I think probably two or three months. Every day we would be like, okay, new screening app. We’d go look at it, he’d be like, all right, I want to do this, this, this. I would do that, and I’d pass the phone over to him and just back and forth like that. We did kind of a whole new color pop for the app, new icons. One of the goals was to really make all of the focus in Instagram on the content, on the photos and the videos, and to take all the color out of the chrome. It’s basically how Instagram looks today, but at that time, we had this kind of dark blue and black chrome everywhere in the app. Things were a lot heavier. We just tried to really simplify it down and make all the color come from the content itself.
Ryan Peterman:
[00:24:06] Was it a gated launch or was it a launch it all at once kind of project?
Ryan Olson:
[00:24:08] So A/B testing was pretty new at Instagram at that point. Facebook was doing a lot of it, and Instagram was kind of more like, oh, we know what’s good, so we’ll just ship it. When I started working on this project, the CTO and co-founder Mike Krieger was like, don’t worry about trying to A/B test this thing. Just ship it, like build and ship it. At that time, they were still sort of using branching as a way to build big features, but I had seen some long-lived branches. The direct messaging feature had been built as a long-lived branch and it was a nightmare merging it back in because they branched off for like three months and weren’t really rebasing. Then they merged this thing back in. It was pretty awful. This redesign touched literally every surface of the app. I was kind of like, well this is not going to be a good way to build it. So I put it behind a feature flag and was constantly merging it and had to build abstractions. All the colors became semantic colors. Instead of saying that icon is black, it’s icon color or something like that, or it’s disabled icon color. Then you could switch inside of that function for, are we on the new design or the old design. That ended up being just a much easier way to build it incrementally. It also opened up the possibility of testing it. We went to ship it and it was going to be just like a 2% holdout. We were going to ship the new icon, 98% of people were going to have the new design, and then we were just going to have 2% of people with the old design just to make sure that nothing was broken or changed drastically. I had submitted the app to Apple. I dropped in the new icon. We were ready to go. People had champagne ready for the launch party, and it was the night before we were supposed to launch this thing. Someone in the Facebook executive team above Instagram came in and was like, no, you guys are not doing this. I guess Facebook had a redesign that went poorly, and they just saw this as the same thing. They were like, you need to run A/B tests of this upfront. I was up at like 1:00 AM just backing things out and trying to resubmit the app to Apple. We tested it and it actually tested really well. It was a little bit sad because it kind of crushed the launch that we had planned. There were all these articles about this new UI that Instagram was maybe going to do. But it all worked out. I did have a takeaway from that, which is testing definitely has a place. It is extremely useful. Even in our startup, we test things where you sometimes get counterintuitive results. Things in our onboarding flow, how people convert on things. It’s extremely useful to run A/B tests for that. I think for high-level product direction and what you want the thing to be, I prefer to come in with a stronger opinion and not just look at the data and only let the data guide the decisions. I think there’s a risk if you do too much experimentation that you get trapped in kind of incrementalism. It’s easy to get those 1% wins, but you’re never going to get that 50% jump.
Ryan Peterman:
[00:28:16] On the major redesign case though, if you just went for it though too. There’s also the other side risk though, right? Your product taste might be off and people hate it, and then it’s a pain to come back.
Ryan Olson:
[00:28:30] Yeah, for sure. I think we had enough confidence in using it. It felt really good internally, and I think at least on the redesigning the app, we thought that would be good. The icon was definitely a little bit more controversial and then when we shipped that, people hated it. It was the last time I looked at Twitter after our product launch because I went on and it was supposed to be the celebratory day. We had worked so hard on this thing, it went out and we were just getting raked on Twitter. It was kind of sad, but I think change is hard. Especially, people feel ownership over their home screens and all of a sudden this thing just changed on them. It was a little bit more of a bleeding edge design direction too. The flat icon and the gradient today feels very at home, but at that time, a lot of the icons were pretty isomorphic and 3D. The funny other thing from that, we could see from the data that this icon change materially improved how many people a day opened the app. We’ve actually seen this in the app of my new company called Retro, but the icon can impact whether people open the app, like how visible it is to them on the screen. It became more noticeable amongst the other icons and people actually tapped it more often. It reminds me
Ryan Peterman:
[00:30:18] of some of Thomas Dickson’s work on the ranking versus chronological. The public perception is so different from how actually people are voting with their usage. People are using it a lot more when it’s ranked. For some reason, there’s this very vocal minority that is saying, I absolutely hate this.
Ryan Olson:
[00:30:42] Totally. The feed ranking shipped about the same time as this redesign. I was actually skeptical of it as well. The metric that changed my mind on the ranking, which I think the story might be a little bit different today, but at the time, one of the things that moved was actually how often people shared to Instagram. People that had this feed ranking experience were actually creating more themselves. They were sharing more. It was partly because the feed ranking allowed Instagram to show them their friends more often. You saw content from people like you, and I think you wanted to have that mutual connection so you would actually share more yourself. That kind of was an insight that flipped it in my mind where people would say, oh, I’m just using the app more because you’re not showing me the things I want, so I’m scrolling further, or whatever. But I was kind of like, okay, they’re actually creating more content. That’s kind of hard to dispute. That’s probably a good thing. I really liked the original mission of Instagram, which was to capture and share the world’s moments. I really liked it as a way to encourage people to be creative and see beauty in the world. That was just a mission I felt like I could get behind. Something like this where people were actually creating more of, it’s like, okay, yeah, that’s probably a good thing.
Ryan Peterman:
[00:32:21] I think at this leg of your career, one thing that you’ve written about is that finding an amazing designer was a big part of it for you. I’m curious, how did you find the amazing designer that you did work with and what makes a great designer great?
Ryan Olson:
[00:32:38] Yeah. I’ve always just tried to be the engineer that the top designers want to work with. It is just an incredible opportunity if you work at these types of companies where you can have their work kind of flow through you and be a part of it. For product engineers, that’s one piece of advice I often give: your impact can be multiplied so much by finding a good designer and creating a really good working relationship with them.
Ryan Peterman:
[00:33:11] Is there a reason why you say specifically the design function versus the engineering function? Imagine I identify a very senior engineer that has some engineering design, and I devote myself to it and kind of attach to them. What’s the difference between doing that versus the really talented designer?
Ryan Olson:
[00:33:30]
[00:33:32] So I should make a bit of a distinction between if you’re in a product engineering function where you’re working on the features for users, the interface, kind of the front end, then I think that’s where you really want to pair with a designer. If you’re in a more infrastructure role, maybe the analogy is like finding that really talented, super senior engineer and being the engineer they want to work with. They’ve got great ideas, and you can implement that. So yeah, probably different depending on what role you have.
00:34:08 — Building Instagram Stories
Ryan Peterman:
[00:34:08] So this Whiteout project was in 2016.
[00:34:11] I am kind of surprised in the same year you also built Stories with Tiger Squad of some very famous people I’m aware of. Can you tell me the story about building Stories for Instagram?
Ryan Olson:
[00:34:24] The redesign wrapped up, and I had actually been kicked off my previous team. Right after I joined, they said, we’re moving the team to New York. Do you want to move to New York? I was like, no, I’m okay here in California. They said, okay, that’s fine. You just have to find a new team. I kind of wanted to be on this team. I delayed it, worked on this redesign project, and then I joined the Search and Explore team.
[00:35:03] I was only on the team for a couple of weeks, and a friend of mine, who was also an IIS engineer at the company, decided to quit. He had been working on what was called the Creation team and leading the project that would become Stories. My manager said, Hey, you know, this is actually a really important effort for the company. I don’t necessarily want you to lead my team, but I think this is a good opportunity for you. I really believed in what this team was trying to do. At that time, it’s sort of surprising in hindsight given how big Instagram is today, but it actually felt in some ways like Instagram was dying because a lot of the everyday sharing from people you knew was evaporating. It was being replaced by creators and influencers, and some of that everyday sharing was going to Snapchat, which had this ephemeral format. We were tasked with how do we get normal people to feel comfortable sharing on Instagram again? I went over to lead the iOS team on Stories. One of the first things we did after I joined the team is we cut the team size significantly. There had been a lot of people working on it, and there had been pretty high churn. They had tried different product directions, and a lot of them didn’t feel that great. They weren’t working out, and in some ways they were working on things to have work for people to do, or there was just not enough space for the people that were there. We decided we could move a lot faster if we went down to a smaller team. It was myself and one other iOS engineer as the core team, and then we’d get some help from other iOS engineers and Android engineers. We didn’t even have a dedicated server engineer; it was the infrastructure team, or you can have half a person, half their time. For what Stories has become, it seems kind of crazy, but it really allowed us to move quickly. You had ownership over the whole thing. It was never a question of am I working on something that someone else is working on? If there’s a bug, it’s like, oh, okay, that’s my bug. I gotta go fix it. There was less discussion around decisions. We could just make them more quickly. I say if you want to go fast, go small. I’m a strong believer in small teams as the best way to operate. It’s definitely not the only way to operate, but it’s my preferred way. We built it just over two to three months; it was pretty quick. I never worked so hard in my life. I was working 16 to 18 hour days, seven days a week, in the office every weekend. I would leave at like 1 or 2:00 AM to go home. I was driving back and forth from San Francisco. I was really determined to not sleep in the office. I was always going to go home, see my girlfriend. It was kind of silly because I was spending this extra time driving. I really should have just slept in the office. It was intense, but it was fun. It felt like we were building something really important, and we were using the product ourselves. We were really enjoying it. It also was this bonding experience among this small team. Our PM on the project is now my co-founder at my company, and I’m very close still with the other folks that worked on it. It felt funny because in some ways we were kind of the incumbent to Snapchat, but in other ways they were very much winning in terms of everyday sharing. We actually felt like the underdog. We had a Ghostbusters poster up in our war room. It felt like we were in this war against them, and I thought maybe we could win.
Ryan Peterman:
[00:39:50] What was it, in your opinion, that when you look at those two products, what was it that the Instagram version was doing so much better than the Snapchat one?
Ryan Olson:
[00:39:58] Yeah, I think we had a sort of unfair advantage in that people already had their friend graph on Instagram and the people that they wanted to share with, but we just weren’t giving them the right outlet to actually do that sharing. As soon as we had that, I think it really stopped the outward flow to go to Snapchat for that type of sharing.
[00:40:28] I think we also did push the format forward. Certainly Snapchat deserves all the credit for coming up with this container that was a lot more comfortable. It’s kind of 24 hour; the content doesn’t stick around forever, full screen, immersive, all those things. At the time, there was a lot that exists in both Stories products today that was not there in Snapchat. Even being able to navigate backwards by tapping left on the screen, that didn’t exist. I think we brought a lot of nice touches like that. The hold to pause, something I mentioned in the career notes. I was using this early version that we had built, and these things were auto-playing and going by too quickly. I intuitively put my thumb on the screen and wanted to pause it, and it didn’t pause. I thought, oh, I can just do that. So then I built the hold to pause, and now that feels like a core part of the navigation and the format. That’s another thing: when I mentor engineers, you have this power as an engineer to just build your ideas. If you are using something and you think it should work a different way, you can just go do that. That’s such an awesome thing. I encourage product engineers: if you have ideas, just build them and put them out and have people try them. It’s such a cool thing to be able to do.
Ryan Peterman:
[00:42:09] It’s insane that you were commuting from San Francisco to Menlo Park, so that’s almost an hour in each direction. You said you were working 16 to 18 hours a day, about seven days a week. I can’t imagine what that was like. One of the learnings from your note is that you should find work that you care about deeply.
[00:42:30] I still wonder, were there times where you were thinking you care about the work, but as a human, I can’t imagine surviving that kind of work schedule?
Ryan Olson:
[00:42:40] It probably wasn’t 16 to 18 every day, but it was working a lot for sure. I definitely sacrificed other parts of my life.
[00:42:51] I used to be a very serious rock climber, was on the U.S. team. I competed in World Cups and I basically gave up that part of my life for sure in that time. But it was also such a unique opportunity to build this thing that was just gonna go out to hundreds of millions of people.
[00:43:12] One of the things I loved most when I was working on Instagram is I’d be riding the Caltrain and I’d look over someone’s shoulder and I’d see them using the thing I’d just built like a week before. That was such a cool experience. You sacrifice certain things, but I was kind of happy to do so.
[00:43:35] Definitely not a sustainable model, so I wouldn’t recommend doing that over a long period of time, but in stints it can make sense. I think by doing that work with that intensity, it paid dividends later on. The Stories product came out. It was much better executed than some of the other Stories efforts at the company. There were ones happening in Facebook and in Messenger. I think part of that was just the care that we put into it. It contributed to its success. The reception on launch was very positive. I was really worried about it. I thought the whole thing was just gonna crash and burn because I could see all these cracks in it.
[00:44:25] You see the crash reports, you see all the bugs, you’re kind of your own harshest critic. But then when it went out, people were like, wow, this is so polished. I was like, really? Are we using the same thing? It was nice to have that reception, and I think it helped the product.
[00:44:44] Personally for my career, having demonstrated that I could deliver this project on a tight timeline with this level of craft helped me get onto the most interesting projects going forward.
00:45:03 — 1 promo per half to Staff (IC6)
Ryan Peterman:
[00:45:03] I saw at the end of the notes you started at IC4 at Instagram and you got to IC6 by the end of this gauntlet of these projects of Whiteout and Stories.
[00:45:15] That’s incredible. What was that like?
Ryan Olson:
[00:45:21] There’s a bit of a funny story. The promotion cycle happened in July. We shipped Stories at the beginning of August, so calibrations were kind of happening in July. We were in the middle of this very intense project and there was a lot of recognition of how hard we were working.
[00:45:44] The managers were being cautious around us. I felt fairly confident that I’d been mis-leveled on higher. I just wasn’t that familiar with levels when I came in and I kind of looked around and I was executing a lot higher than IC4.
[00:46:07] My Android counterpart, who is an incredible engineer, Will Bailey, was sort of the tech lead for the whole Stories project. He set the example for me of how you could be a successful product engineer. He was incredible at getting me into the meetings and being in the room with Mike and Kevin as we made all the decisions.
[00:46:30] He was an IC8, so he certainly had a bigger role in the project, but we had somewhat similar roles. I was at IC4, he was at IC8. That opened my eyes to some of the leveling stuff. I told my manager at the time, Eddie, who was the director. I was reporting to the director because it was kind of a unique project at the company. I said, “Hey, I think I got mis-leveled and I think you should promote me from four to six in this cycle.”
[00:47:15] To his credit, he didn’t just brush me off. He actually went and talked to HR about it and they came back and said, “We’ve done this twice in the history of the company. In both cases, it worked out terribly. The people left very quickly.” He said, “We’re not gonna do it.” But I wanted to seed the idea that the correct level for me is a higher IC6.
[00:47:34] I knew it was unlikely that they were just gonna do that one step, but I guessed that if I was on that normal cycle, I knew it would come up the next time and they’d be like, “Well, he just got promoted last half. We can wait.” I think it’s good for people to recognize that ultimately these levels and promotions are an incentive system. In the long run, there’s really an effort to make it fair, but there’s also an element of like, it’s the carrot that’s being dangled in front of you.
[00:48:18] It can make sense even if somebody’s performing at a higher level that the promotion gets delayed just so that they’re not happening in quick succession. I wanted to seed the idea that they should probably get me to six pretty soon. The first half on Whiteout, the redesign, and some of the infrastructure stuff, I got the IC5 promotion and then the six came for Stories.
Ryan Peterman:
[00:48:51] It’s interesting that you say your high performance, of course the promotions are one thing, but one of the things that you took away personally is that it gave you freedom to work on whatever projects you wanted.
[00:49:03] How does that play out?
Ryan Olson:
[00:49:05] I think it just demonstrated that if you put me on a project, I’m gonna do a good job with it. When there is a new effort at the company, it’s just kind of natural to take the people that have done well on the new efforts before.
[00:49:23] I was very lucky to have the opportunity, but executing well on it set me up well for the future.
Ryan Peterman:
[00:49:34] I noticed a similar model with Instagram Threads, which is you pull together all the top Instagram people and you got this small team similar to the Stories team. All those people have proven themselves repeatedly.
00:49:51 - Senior staff promo project (IC7)
Ryan Peterman:
[00:49:48] The next promotion actually came from IGTV, which, my understanding, is like a YouTube clone almost, or like the vertical video first in Instagram. Could you talk about that project that got you promoted to IC7 or Senior Staff?
Ryan Olson:
[00:50:08] It came from Kevin, the CEO, and Ian Silber, another amazing designer. Before an end of year all hands, they designed this thing together and laid out this vision for Instagram getting into longer form video. It was gonna be mobile native, so it was gonna be vertical the way that you hold your phone.
[00:50:41] It came with a fairly developed vision to the all hands and was presented to everybody. I saw that and I thought, I gotta work on this thing because this looks cool. It ended up being a bit of a weird project in the beginning because it was the surprise reveal.
[00:51:03] If you read through some of the recent antitrust litigation with Facebook, there are insights into tensions between Facebook and Instagram during this time. We were told not to work on it for a while, which was kind of the end of the founders’ time at Instagram. IGTV was the last major thing they were there for.
[00:51:26] It was a really cool group, a very small team: myself, Will Bailey, Thomasson, and kind of like iOS, Android, and server leads. We each had one or two other people per platform. It was a super talented group, great engineers, great designers. We moved super quickly.
[00:51:57] The product doesn’t exist anymore today. It didn’t end up doing that well. It’s interesting to reflect on why. It had some things that ended up becoming the future, like vertical video is very much a thing today. It was trying to mix long form YouTube style content into this vertical format, and maybe that was a bit of a mismatch. People just weren’t producing high quality long form in the vertical format. We tried some interesting AI techniques to take landscape content and reformat it for vertical. I’ve got a patent on that, which is one of my more interesting patents.
[00:52:46] We showed that to creators and they were horrified. They said, “You’re destroying my content. Why have I spent so long making this nice landscape video? Now you’ve just ruined it.” We tried to push people to produce original long form vertical video, but the inventory just never really showed up. There was maybe a little bit of hubris. It was like, Instagram can just change the industry. People will just start making this because we have this platform and this audience, and that didn’t totally materialize. I think it probably did inform a lot of what ultimately shipped as Reels, but IGTV itself didn’t totally work out.
Ryan Peterman:
[00:53:27] I was working on the video infrastructure team at the time, so that was one of the things that I got plugged into at some point. I remember the energy in the San Francisco office and the war rooms, et cetera. You mentioned antitrust. What’s the antitrust component you’re talking about?
Ryan Olson:
[00:53:47] A lot of the sort of internal communication has now become public through this antitrust lawsuit where the Justice Department is suing Facebook to unwind the Instagram acquisition. Certain things that were kind of confusing to me at the time, like why certain things were happening, are less confusing now that I read some of the internal communications that were previously private, including private to me. I wasn’t exposed to it. But yeah, I mean, I think basically Instagram had been acquired. It was smaller, certainly small relative to Facebook, and then had gone through several years of just incredible growth and now was kind of more of a peer to Facebook and was kind of like the new popular kid. In terms of Instagram Stories, it was received better than the Stories in Facebook. I think that created some tension between the Instagram leadership and the Facebook leadership. There were concerns about Instagram cannibalizing or taking users from Facebook, which guided some of the strategy decisions.
Ryan Peterman:
[00:55:18] I remember that too because I was also on the Instagram team and I remember there was some confusion about why we were turning off the followers being forwarded from Facebook to Instagram, or it was like cross-sharing or something. The direction from Facebook to Instagram was getting turned off. I think I read the same thing you read because I was like, oh, this makes so much sense. It’s like Mark Zuckerberg’s internal memo on all of that and all the tensions between the Instagram founders and saying he wants to keep them and they’re great at building products, but he’s trying to navigate his side of the equation. Super interesting.
Ryan Olson:
[00:56:03] It’d be really interesting to know how he thinks about it today. That was now seven years ago.
Ryan Peterman:
[00:56:12] The Instagram founders,
Ryan Olson:
[00:56:14] Mark, because I sense in those communications something of a very understandable emotional attachment to the Facebook product, right? This was kind of the thing that he created in Instagram. He deserves all the credit for acquiring it, but it was a little bit less his thing. I just wonder, does he view that differently today than he did seven years on? He owns both of these things. I always had the view that the best way to get the best outcome for the overall company was actually to have these things compete with each other because you own both. They’re gonna make each other better and one of them will win. If you stifle that competition, somebody from the outside is more likely to come up with something better and take over. I don’t know. I mean, he’s the one running a multi-trillion dollar company and I’m not armchair CEOing over here.
00:57:37 - IG labs & his principal promo (IC8)
Ryan Peterman:
[00:57:30] Yeah. Maybe one day if this podcast scales up and I ever have Mark on, I’ll ask him that. Lastly, at Instagram, I know you started a group called IG Labs. I’m curious about the story behind you starting that group. I also understand this is your promo to IC8 or like Director equivalent at Instagram. So yeah, what’s the story behind IG Labs?
Ryan Olson:
[00:57:55] After IGTV, I definitely spent some time, like Thomas Dimson has this phrase like wandering the impact desert, looking for things to do and not necessarily finding anything great. I was actually pretty close to leaving the company at that time. The new effort became Reels and I didn’t feel good about working on passive video consumption. My manager was over the Reels org, so it would have made sense for me to work on it, but I was fairly certain I didn’t want to work on that. I helped the team a bit, but it wasn’t gonna be my project. Through that time, there was a lot of culture change. The founders had left, and the leadership kind of came over from Facebook. The new leadership felt like a lot of the old Instagram culture was being pushed out. I was talking with the new head of engineering about trying to bring back some of that energy that I think had made product development at Instagram special: small teams, attention to craft, and also really expanding the scope of what we worked on. We were very focused on the existing Instagram app and the existing features within Instagram and just kind of like iterative features on that, very incremental improvements. I made this pitch that we have this great brand, we could do other things under the Instagram brand. Let’s explore location ideas, maps ideas, places. I paired with a really awesome designer, Vivian Wong, and we made the pitch to start this team. It was just her and myself in the beginning. The idea was to have this small group, very high talent density that would work on new product initiatives and things that didn’t slot cleanly into the org. Instagram had grown to such a size where you really needed a lot of structure in the org just to keep things sane, but that meant that projects that didn’t slot cleanly into one of those orgs were probably under-invested in. Part of the idea of this team was that we would span across, we wouldn’t have a focus area. We could work across many things. We tried a lot. A lot of it didn’t ship or test. Probably one of the more lasting, impactful things, it seems small, but I think it actually gets used quite a bit, is the collaborative post feature where you can have multiple authors on a post. It’s one of the more interesting patents I have. I think we found good impact. We were also this concentration of talent that when there was a new important initiative, ultimately ended up being Threads, you had this group that could go work on it. Just trying to encourage innovation, trying new things, and push that at the company.
Ryan Peterman:
[01:01:45] The last thing on your Instagram journey was that you tried management at some point, or as an IC7 you switched to TLD or Tech Lead Director. What was your thinking behind that and how’d it go?
Ryan Olson:
[01:01:58] It’s a very unusual or rare role within Facebook. Even TL is quite rare, or it was at the time. Then like Technical Director, probably even more so. It kind of happened mostly because I had started this group and at some point it just made a lot more sense for me to manage the people in that group rather than my manager who was over the Reels org and just less connected to their work. I could probably represent them better in calibrations. I was in the calibrations anyways, so it was kind of like doing a lot of this work. In some ways it was just kind of like a formal recognition of what I was doing already to have these people report to me. Facebook is very much of the school of thought that individual contributors and management should be separate, and I don’t subscribe to that. Other companies work differently. My wife is a Senior Staff Engineer at Tesla and they’re very flexible. ICs have people report to them all the time. Managers are expected to be pretty competent technical contributors and doing individual contributions. I think I prefer that model. It was interesting for me to try it. I think another one of my controversial opinions is that senior engineers should be involved in coding. There’s overlap between that thought and the thought that managers should be somewhat involved. There’s an author I really like, Nassim Taleb, and he talks about having skin in the game. If you’re a senior IC who has to do some coding, you have more skin in the game. You’re not gonna come up with some architecture that you just hand off to somebody else and it’s their problem now. You’re gonna be involved, you’re gonna see more hands-on what the issues are. Similarly, if you’re managing a team and you’re much more with them in the day-to-day stuff, I think you will operate better. It’s maybe a bit against the grain at Facebook, but it was a philosophy I had and I wanted to try it. There was an upside to it as well in a company that grew so much and was so big where at Facebook, the levels are private. You’re just a Software Engineer through your whole IC time. In some ways, I like that for engineering discussions that there’s no pulling of rank. It’s a little bit more meritocratic perhaps. But in cross-functional situations, say you’re working with a PM, like I’m trying to ship this collaborative posts thing and I have to meet with PMs on these different teams. There was an element where having a little bit higher of a title made those conversations easier. I had a higher baseline where they were like, okay, this person maybe knows something. They’ve been here a bit. They’re not just totally new. You build up some reputation in a company, but when it gets so big and there are new people joining all the time, you’re actually having to reestablish that a lot with folks. I think it was somewhat helpful to have that title. There would be discussions in the senior engineering group about whether there should be some form of public levels within the company. I was supportive of maybe not the full levels being public, but like a senior designation or something, just largely for when you’re working with people outside of your normal working group so that they start from a slightly better baseline on whether you know what you’re talking about.
Ryan Peterman:
[01:06:38] The number one thing I hear people say is this is not optimal because you’re doing two jobs at once and you’re gonna drown, and your career will not flourish in either direction. What do you say to that?
Ryan Olson:
[01:06:53] It’s probably correct. At that point, I was really not optimizing for career.
[01:07:01] It was never my intent to stay long term. I mentioned this in the career note; Facebook does these internal employee sentiment surveys every six months or year. One of the questions on there is how long do you intend to stay with the company? I never put more than one year.
[01:07:24] It was always like, okay, this is my last year. I’m gonna get out soon. I didn’t have aspirations to get to IC9, and so it kind of freed me up where it was like, I don’t wanna get fired for performance, but I kind of knew I wasn’t gonna get fired for performance.
[01:07:45] There was just a little bit less pressure on that, so I could just kind of do the thing that made sense for our group, our team, and worry a little bit less about the career stuff. But yeah, absolutely. I think I saw firsthand that my ratings were probably lower than they would’ve been if I was just an IC.
[01:08:11] It was like, okay, you’re exceeding as an IC but you’re meeting as a manager, so you’re just meeting.
01:08:19 — Starting Retro and leaving big tech
Ryan Peterman:
[01:08:19] That’s kind of like the full journey from start to finish of Instagram. I know you’ve since left and you’re working on Retro, which is a popular social media app with a lot of the polish I recognize in Instagram as well.
[01:08:36] I am curious what made you wanna leave to start that? What’s the story behind creating Retro?
Ryan Olson:
[01:08:42] So around the last few months of my time there, I was talking with Nathan, my co-founder. We had worked on Stories together. He had gone over to the Facebook side, started Facebook Dating, and then was working on some of the virtual reality products.
[01:09:02] Through our whole time, we were close friends. We would meet up at this bar sometimes in the Mission called Lone Palm, and we would talk about how we just saw a different way to build products, to structure a company. We really wanted to be in the driver’s seat of that.
[01:09:23] We would talk about starting a company, but the timing wasn’t right for me. I was on a project that I was engaged on, and then I’d be like, okay, I think I’m ready. He was on something new. Finally, our timing kind of aligned where we were both ready to leave, and I had a conversation with this investor friend, the same one that connected me with Flipboard, who’s kind of a mentor of mine.
[01:09:50] He was like, it’s time; you should really take a bet on yourself. That stuck with me. I was like, yeah, I should take a bet on myself. We left to start the company. Our goal with the company is really to create this world-class product studio. Retro is our first product, but it’s not necessarily the reason for the company existing.
[01:10:19] We want to create an environment where great product builders can do the best work of their lives and create products that are good for people, that they feel good after using, and also to create a successful business. Retro is our first product, and it’s a social app, but it’s actually quite different from what are called social apps today in that it’s actually social.
[01:10:52] You see people you know on it. Friends, it’s all focused around friends. Traditional social media is maybe, well, the derogatory term I would say is brain rot media. Entertainment is maybe a more favorable term, but if I open Instagram today, I don’t see a lot of the people I know.
[01:11:20] Even if I go to seek that out, I tend to end up down a rabbit hole of short-form video entertaining content. It’s definitely entertaining, but it kind of hijacks my attention. I get sucked into it. The idea behind Retro is we’re creating a space that’s all about connecting with the people that you actually know, staying up to date with them, and also appreciating your own life by looking back on your photos and picking out the highlights.
[01:11:52] In some ways, it’s a throwback to the earlier times in social media, what Instagram used to be all about—creation. Almost half of the people that use Retro on a daily basis actually post something, which I know from working on Instagram that number is quite a bit lower.
[01:12:11] I take it as a really good sign that we have created a product where people show up to create almost as much as they show up to consume. We’ve been working on that for the past few years. It’s become very popular in Taiwan, which is not something we expected. Social networks are so much about the network, whether your friends get on it.
[01:12:38] We managed to hit the critical mass in Taiwan, and all of the usage patterns end up looking different when you hit that critical mass. We were number one on the App Store there for a period last year, and we still are at the top of the photo category. We were number two when I looked this morning.
[01:13:00] We’ve shown that when it works, it works. We had just this challenge of making it work in more places. It’s very challenging to get people to try a new app. If you miss seeing your friends and people you know on social media and staying connected with them, I encourage you to try out Retro. I think it’s a really delightful app.
[01:13:30] I love seeing photos from my family on there, and we want it to feel good when you open it and feel good when you close it so you don’t feel like your attention was hijacked, that you feel like this was a good use of time. You got caught up with the people you care about, and then you can go on with your life. You can get out and enjoy the world. The design
Ryan Peterman:
[01:13:50] philosophy you went for with this app? Is it more challenging to get people to use it because it’s less addictive?
Ryan Olson:
[01:13:57] One of the key decisions we’ve designed around is that we don’t have an ad-based business model. I don’t think ads are evil, but I do think that ads when combined with an algorithmic feed are a little bit evil because you have this misaligned incentive.
[01:14:24] I think the app is incentivized for you to just consume more and more. It just wants more and more of your time and attention, even past what you wanted to get out of the app. I show up to see what a friend is doing; it’s gonna try to keep me there for the next hour, two hours, whatever.
[01:14:47] Ads fundamentally, when combined with an algorithmic feed, make products that aren’t super aligned with people. There is definitely a challenge in terms of growing Retro. We don’t have creators. The model is mutual friending. Everyone is private. You can only see people that you’ve accepted as friends, and it has to go both ways. It’s not like a following model. We have a limit of 250 friends, so you can’t build an audience on this platform.
[01:15:38] A lot of the ways that Instagram grew was through creators that were financially incentivized to spread this app and get more followers. Those pathways to growth are not open to us. We’ve seen examples like BeReal, which managed to get decent growth with a nice viral mechanic built in with this notification that everyone got: “It’s time to be real.” That created a lot of conversations, so that certainly helped.
[01:16:04] I think it is possible to grow a friends-only social network, but in many ways, it is harder, and the business model is harder. We’re very open about this challenge. There would be easier ways to do things, but we think they would lead to bad outcomes, outcomes we don’t want in the long term. We’re taking an opinion on what this product should be and what we want to see in the world.
[01:16:26] Some people say just build what people want. You could say in Instagram people are demonstrating that it’s what they want because they spend more of their time there. We’re taking a more opinionated stance, saying no, we think that’s not great and this is better. Even if it’s more challenging, it’s something we strongly believe should exist in the world and should be an option for people that want it.
[01:17:07] I think we also coexist really nicely alongside Instagram. I still have it, I still open it, but I’m getting sucked into it a lot less, and it’s helped me break this phone addiction that I didn’t feel good about.
How do you monetize? If you’re not using ads, we have a premium subscription. It’s only a small percentage of users that are subscribers, and it’s just kind of like an extra tier of features, particularly some of the things that cost us a lot to provide as a service.
[01:17:35] Video, as you know from video infrastructure, the storage and bandwidth for that is quite a bit more than for photos. You have to subscribe if you want to share out video. The free version of the app is actually great. You can share photos, you can remember your own life. About 93% of what people share on Retro is photos anyway. If you want to support the mission and get those extra features, you can become a subscriber.
Ryan Peterman:
[01:18:12] I love the intention behind it and the mission. It’s really cool.
Ryan Olson:
[01:18:17] It’s definitely a product that’s fun to work on.
[01:18:19] It feels good. It’s very feel-good. We had a tagline for a while: feel-good social media, and yeah, it’s very much that.
Ryan Peterman:
[01:18:29] It’s coming from big tech and starting your own company. I’m curious, looking back across the various career axes of learning, satisfaction, compensation, the things that people look at for their career.
[01:18:45] How has it been so far working on your own thing?
Ryan Olson:
[01:18:49] Yeah. Compensation is quite a bit worse. Nathan and I pay ourselves less than all of our employees, and we have more ownership in the company, which I think is the right way. It’s how it should be. But that means that I’ve certainly put off that short-term compensation.
[01:19:09] We hope to become a very successful company and that equity is gonna be worth a lot, both for us and for our employees. It was always the thing I wanted to do. I was a bit surprised actually that I ended up in Big Tech, talking about those early days in Flipboard and this entrepreneurial culture.
[01:19:31] It was always exciting to me. I would read TechCrunch all the time about the new startups, and I just always wanted to build a company, bring the best people together, work on the things that we thought were cool, do things in the way that we wanted to do them.
[01:19:54] It’s been awesome for that, and I’ve definitely learned a ton. I think the amount of time that I get to spend on interesting work is much higher than it was, especially in my later years at Instagram. A lot of my work became convincing layers above me that we should do something.
[01:20:21] There were probably more people working on that app than there needed to be. There was a lot of gatekeeping, where it was like, is your team allowed to ship? You would do this work, and then you have to convince somebody that this is a good enough thing to ship in the product, which is understandable because it becomes very complex if you just let everybody go.
[01:20:50] But it means that there’s a lot of work in just that political wrangling and how do I make this person feel like this is their idea, not my idea. I’d spend none of my time on that now. We do a one-hour standup every day. That’s basically the only meeting on my calendar.
[01:21:12] So I get almost the whole day to just build, think about what people want, and try to make it. I’d say satisfaction is definitely higher. Learning is definitely higher. Compensation is definitely lower.
01:21:33 — Small teams hypothetical
Ryan Peterman:
[01:21:32] I think throughout the conversation you mentioned that smaller teams can move faster.
[01:21:38] Do you think that the company would be better off if you just laid off half the people?
Ryan Olson:
[01:21:44] I would say yes. We used to talk about this a lot when the company was much smaller, this thought experiment of like, you know, the Thanos, like you just snap your fingers and half of people are fired, even if it’s a random selection.
[01:22:00] Do things go better? Frequently we felt like, yeah, maybe they would. It’s tough because with a business like Instagram, if you can make a 0.1% improvement, it’s actually hundreds of millions of dollars to the business. Sometimes that incremental person may be able to find those things.
[01:22:28] But I think it’s less appreciated the cost of each person you add. There’s the more obvious organizational communication overhead. You just have more stakeholders, more meetings, more coordination, but even just writing more code, having more code in the app.
[01:22:52] I remember right before I left, they had this tool where you could see how much time you were spending compiling the app. I was spending more than four hours a day waiting for the app to build just because there was so much code. The tooling just had not kept up with the velocity at which people were writing code.
[01:23:21] That’s a huge cost. It’s not noticeable with each incremental person you have, but now you have a thousand engineers and all of a sudden everyone’s just slowed down because of this overhead. With a smaller team, when we were 10 people and the app was tiny, it was so much easier to get things done.
[01:23:46] A project like Whiteout would be a massive project for Instagram today because there are so many more surfaces, so much more code, so many more people. It was actually a lot easier at the time that I did it.
Ryan Peterman:
[01:24:01] Yeah. I guess Twitter is kind of an interesting case study of that because they went through that and the app’s still operating.
[01:24:11] I do get the sense that there’s a lot more breakages, but I’d be curious, on the product development side, how has that been being on those teams?
Ryan Olson:
[01:24:20] Totally, yeah. I think there were projections when Elon came in and I think he cut like 80%. A lot of the staff left as well.
[01:24:30] Right. There was a sense that this thing was just gonna a hundred percent fall over. My experience is somewhat buggy. There’s definitely some issues, but it’s very much continuing to run. I think the economics of the business have actually become much better. It’s actually profitable now.
[01:24:55] Whereas through almost its entire history, it was operating at quite a loss. So, yeah, somebody coming in with a machete cutting things may be okay.
01:25:17 - Examples of talented individuals
Ryan Peterman:
[01:25:09] Okay. Towards the end of the conversation, I just want to wrap up with a few career reflections. The first thing is throughout your projects, you worked with a lot of very talented people.
[01:25:21] You mentioned Thomas Dimson, Will Bailey, a few incredible designers. It sounds like you worked with the founders of Instagram, and I’m curious, do you have any stories that illustrate what made them exceptional?
Ryan Olson:
[01:25:36] Mike Krieger is definitely something of a hero of mine, and it was such a privilege to work with him.
[01:25:44] They say don’t meet your heroes because you’ll be disappointed, but I think you should meet Mike Krieger. He’s actually an awesome human, and a lot of the ways that I think about engineering leadership and engineering philosophy came from him. I mentioned earlier the simple thing first.
[01:26:05] That’s really stuck with me. I think the attention to detail and craft. Another thing is he had this sort of, I don’t know if it was intentional or just the way he is, but it was like this lead from the front way of operating where he never put himself above the team and would jump in to help if an effort needed it.
[01:26:33] At the end of stories, I had brought in a friend of mine from Flipboard who was then working at Facebook, not at Instagram, a very different team to do the drawing tools just because he had worked on a drawing app before. I was like, hey, we need drawing, can you work on this?
[01:26:55] He worked on it for a few weeks and got it reasonably far, but then kind of got pulled back by his team. We were in a bit of a pickle, and Mike just came in and was like, okay, I’ll finish it. He was in there coding the neon brush, and we were working those insane hours. He was there working them with us.
[01:27:17] He was up at 2:00 AM reviewing my diffs. Seeing that and how that felt as a team really has informed the way I think about leading teams. He’s awesome. Some of the other folks you mentioned, Will Bailey, I talked about him a little bit before. He has this product vision that he sticks to very strongly, and frequently it’s quite good.
[01:28:15] At the dark days of development of the Stories project, when it was spinning in circles, taking different forms, none of them felt very good, he outlined this full vision in a document for how this product should work, the things we could do with it going forward. I looked back on it five years later and was like, wow, this was like the five-year roadmap for what we ended up doing.
[01:28:32] He basically nailed it all from the start. He was such a good example of how you could succeed as a product-focused engineer. That was much more of a thing in Instagram than it was in Facebook. I remember being in bootcamp and people were saying, okay, if you’re junior, you go work on a product team, and if you’re senior, you work on an infrastructure team.
[01:29:00] The culture was like, product is easy, but real engineers work on infrastructure. Instagram prioritized more the product side. I think that was reflected in the various versions of Stories, for example.
[01:29:21] Will was such a great mentor and example of how you could have a successful career as a product engineer, how you could influence product direction as an engineer. Thomas is probably just the smartest person I’ve ever met. He’s incredibly smart, but not in a savant kind of way. He’s also got great social skills and understands people.
[01:29:47] He did the feed ranking, basically started all the ranking at Instagram. He started his own company. OpenAI bought his company. He’s a researcher there now. Maybe Zuck is coming to him with a hundred million dollar offer. I don’t know.
[01:30:11] He had this skill on the infrastructure side, built a lot of the infrastructure for the ranking stuff, but always approached it with a product mindset. I think he would probably consider himself a product person. I’ve always been interested in technology as a means to create things for people. I’ve never been that interested in the technology itself.
[01:30:33] It’s only interesting to me to the extent that I can create interesting experiences for people. I think Thomas and Will had a similar approach, a very human-oriented thinking about the psychology, how people use these things and how it makes them feel.
01:31:16 — Advice to his younger self
Ryan Peterman:
[01:31:16] And then, last question is. If you could go back to yourself after all this experience that you have and talk to yourself when you are just graduating college and give yourself some career advice, what would you say?
Ryan Olson:
[01:31:28] Just invest in the tools of your time to build things for people, like build products for people.
[01:31:36] And I think if you do that, you’ll be pretty flexible and adaptable. You have a unique opportunity as a new grad because you aren’t stuck on this path of being an iOS person, knowing this technology really well. It’s all new to you, and so you can pick up the latest thing, right?
[01:31:59] And so I think with these AI tools that are coming out, you can do incredible things with them and you’re probably gonna be more skilled at those than the senior engineers because it’s just not the thing that they learned natively or invested their time into. I had that to some extent with iOS where it was newer.
[01:32:23] The senior engineers were writing Java or something, running our backend, and I could actually stand out and excel because it was the first thing I learned. I was eager and hungry. I think there’s something to that with this new set of AI tools.
[01:32:41] So, yeah, I think my advice for new grads is to learn the tools of your time, get good at them, and make good things for people. I think that will work out. It seems like there’s reducing demand for junior software engineers because of some of these AI tools.
[01:33:05] But I think if you can get really good at using those tools, there will definitely be roles for you.
Ryan Peterman:
[01:33:12] Awesome. Well yeah, thank you so much for your time. That was really, you’re a legend at Instagram and I worked there for so long. Super excited to talk to you. At this point, is there anything you want to redirect the audience attention to?
Ryan Olson:
[01:33:26] If the ideas behind Retro sound interesting to you, definitely try it out. It’s a great place to reconnect with people that you want to see in their lives, but maybe they’ve stopped posting on social media, so get them onto. If you’re a designer or an engineer, definitely reach out.
[01:33:48] I think we have some interesting ideas in how we’re building this company. Our goal is to become a world-class product studio with multiple products. We have Retro and two more in the pipeline right now, and I think we have some interesting ways we’re structuring revenue share with employees.
[01:34:09] As these apps start to make money, even if the company’s ambition is to reinvest it into growth, you can see some of that upside right away. We’re building infrastructure that helps support products across the portfolio. We’re building growth tools, analytics tools, all of that, that I think are gonna really help us excel as a product studio.
[01:34:35] So if that’s interesting to you, reach out for a conversation. It’s just been a pleasure chatting, and thanks for having me on. Thanks so much, Ryan. Really appreciate your time.
01:34:45 — Outro
Ryan Peterman:
[01:34:45] Thanks for listening to the podcast. I don’t sell anything or do sponsorships, but if you want to help out with the podcast, you can support by engaging with the content on YouTube or on Spotify. If you want to drop a review, that’ll be super helpful.
[01:35:01] If there are any guests that you want to bring on, please let me know. I feel like sourcing very senior ICs, there’s no well-studied list out there on Google that I can just search. If there’s someone in your org or at your company who you really look up to and you want to hear their career story, let me know and I’ll reach out to them.
