Instagram Principal Eng (IC8) On Building IG Stories, 1 Promo Per Half, Small Teams

26:05Ryan Olson:And then we were just going to have like 2 % of people, you know, with the old design just to make sure that like nothing was broken or changed drastically. And I had submitted the app to Apple. I dropped in the new icon. You know, we're ready to go. People had champagne ready for the launch party. And it was like the night before we were supposed to launch this thing. and um someone kind of in the facebook executive executive team above uh instagram came in and was like no you guys are not doing this um i guess they facebook had had a redesign that went poorly um and they just saw this as the same thing and uh and so they were like you need to run A-B tests of this upfront.

26:53Ryan Olson:Um, so I, you know, I was up at like 1am just like backing things out and trying to like resubmit the app to Apple. And, uh, we, we tested it and actually tested really well. Um, it was a little bit sad cause it kind of crushed like the launch that we, we had planned. Um, you know, cause then there are all these articles about this new UI that instagram's maybe gonna do um but uh but yeah i mean it all worked out um but i i did have a a takeaway from that which is like um i mean testing definitely has a a place it's extremely useful even in our startup you know we test things where you sometimes get counterintuitive results um things in our onboarding flow how people convert on things um it's extremely useful to run a b test for that i think for like high level product direction and like what you want the thing to be i prefer to come in with a stronger opinion and not just kind of like um look at the look at the data and only let the the data guide the decisions um so i i think there's a risk if you do too much experimentation that you get trapped in kind of incrementalism so it's you know easy to get those one percent wins but you're never going to get that 50 percent jump on the major redesign case though if you just went for it though too there's also the other side risk though right which is your product taste might be off and people hate it and then it's a pain to come back yeah yeah for sure um i i think we we had enough confidence i guess in in using it i mean it felt really good internally and um i think at least on the inter in kind of redesigning the app we we thought that would be good um the icon was definitely a little bit more controversial and then when we shipped that people hated it i mean it was like i say it's the last time i looked at twitter after a product launch because i went on and you know it's 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.

29:09Ryan Olson:And, uh, yeah, I mean, it was, it was kind of sad, but I think, you know, change is hard. Um, especially I think people feel ownership over their home screens and, and all of a sudden this thing just changed on them. Um, and it was kind of like a, a little bit more of a bleeding edge design direction too. Like, I think the, the flat icon and the gradient, you know, today feels very at home, but at that time, a lot of the icons were pretty skeuomorphic in 3D. Yeah. So, so it was a bit rough. The, the funny other thing from that, you know, we could see from the data actually that, uh, this icon change, uh, it materially improved how many people a day open the app.

29:53Ryan Olson:Um, and we've actually seen this in, in, um, the app of my new company called retro, but actually like the icon, uh, can impact whether people open the app, like how visible it is to them on the screen. So it became more noticeable, I think, amongst the other icons and people actually tapped it more often. It reminds me of, I think some of Thomas Dimson's work on the ranking versus chronological, like the public perception is so different from how actually people are voting with their usage. Like people are using it a lot more when it's, when it's ranked, but you know, for some reason there's this like very vocal minority that is saying, I absolutely hate this.

30:42Ryan Olson:Totally. Yeah. That, that actually, um, the feed ranking, um, shipped about the same time as, as this redesign. And, uh, I mean, I was actually skeptical of it as well. Um, the, 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. So people that had this feed ranking experience were actually creating more themselves. They were sharing more. And it was partly because the feed ranking allowed Instagram to show them their friends more often. And so you saw content from people like you, and I think you wanted to have that mutual connection so you would actually share more yourself and so that kind of was an insight that flipped it in my mind where you know because people would say oh I'm just using the app more because like 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 like creating more content that that's kind of hard to dispute like that's that's probably a good thing um I I really liked kind of the mission, the original mission of Instagram was like capture and share the world's moments.

32:04Ryan Olson:And I really liked it as a way to kind of encourage people to be creative and see beauty in the world. And that was just a mission I felt like I could get behind. And so something like this where people were actually creating more, I was like, okay, I thought that's probably a good thing. I think at this leg of your career, I think one thing that you wrote about is that, you know, finding an amazing designer was like a big part of it for you. And so I'm curious, how did you find the amazing designer that you did work with and what makes a great designer great? Yeah, I've always just tried to, you know, be, be the engineer that like the top designers want to work with.

32:44Ryan Olson:Um, and yeah, it's just an incredible opportunity if you work at these types of companies where you can just have their work kind of flow through you, um, be a part of it. So that for product engineers, that that's one piece of advice I often give is like your impact can be multiplied so much by finding a good designer and creating a really good working relationship with them. Is there a reason why you say specifically the design function versus the engineering function? Like imagine I, I identify some very senior engineer that has some engineering design and I just devote myself to it and kind of attach to them.

33:28What's the difference between doing that versus the really talented designer?

33:32Ryan Olson:So I should make a bit of a distinction between like if you're in sort of a product engineering function where you're working on like the features for users, the interface, kind of the front end, then I think like, you know, 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 kind of implement that. So yeah, probably different depending on kind of what role you have. And so this Whiteout project was in 2016.

34:11I'm 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, you know, building stories for Instagram?

34:24Ryan Olson:The redesign wrapped up and I had actually been kind of 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? And I was like, no, I kind of, I'm okay here in California. They're like, okay, that's fine. Well, you just have to find a new team. I was like, okay, I kind of wanted to be on this team. So I kind of like delayed it. I worked on this redesign project. And then I joined the search and explore team. And I was only on the team for a couple of weeks. And a friend of mine, who was also an iOS engineer at the company decided to quit.

35:13Ryan Olson:And he had been working on what was called the creation team and leading the project that would become stories. And, uh, my manager, um, was like, Hey, you know, this is actually a really important effort for the company. Like, I don't necessarily want you to leave my team, but like, I think this is a good opportunity for you. And, um, I really believed in, in what this team was trying to do. Um, at that time, it 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 sort of everyday sharing, uh, from people you knew normal people was evaporating.

36:00Ryan Olson:It was kind of being replaced by creators and influencers. And, uh, some of that everyday sharing was going to Snapchat, which had this ephemeral format. Um, and so we were tasked with just, you know, how do we get kind of normal people to feel comfortable sharing Instagram again? So I went over to, to lead the iOS team on stories. And, uh, one of the first things we did after I joined the team is we actually cut the team size significantly. So there had been a lot of people working on it. It'd been pretty churny. Um, they had tried different product directions. Uh, a lot of them didn't really feel that great.

36:44Ryan Olson:They weren't working out. And in some ways they were working on things to have work for people to do. Um, or, or there was just like not, um, not enough space for the people that were there and we just decided, hey, we can actually move a lot faster if we go down to a smaller team. So it was myself and one other iOS engineer was kind of like the core team. And then we'd get some help from other iOS engineers to Android engineers. And we didn't even have a dedicated server engineer. It was the infrastructure team where like you can have half a person half their time, which, you know, for what stories has become, it seems kind of crazy.

37:26Ryan Olson:Uh, but it, it really allowed us to, to move quickly. Um, you had ownership over the whole thing. So it was never like a question of, uh, am I working on something that someone else is working on? Am I going to step on their toes? You know, if there's a bug, it's like, Oh, okay, that's, that's my bug. I got to go fix it. And, uh, and there was less discussion around decisions. We could just make them more quickly. I say like, if you want to go fast, go small. Uh, and I'm a strong believer in small teams as like really the best way to operate. Um, it's definitely not the only way to operate, but it's my preferred way.

38:04Ryan Olson:And, uh, yeah, so we, we went through that and, um, we built it just over two to three months. It was pretty quick. I never worked so hard in my life. I was working, yes, like 16, 18 hour days, seven days a week. in the office every weekend. Yeah. I would like leave at like one or 2 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 like, you know what? I'm always going to go home, see my girlfriend. And it was kind of silly because I was spending this extra time driving. I really should have just slept in the office. But yeah, it was intense, but it was fun.

38:50Ryan Olson:It felt like we were building something really important. And we were using the product ourselves. We were really enjoying it. It also was like this bonding experience amongst this small team. So our PM on the project is now my co-founder at, at my company. And, um, you know, I'm very close still with, with, uh, the other folks that worked on it. And it also, it felt, it's funny because in some ways we were kind of the incumbent to, to Snapchat, but in other ways they were very much winning in terms of this kind of like everyday sharing. And so we actually kind of felt like the underdog. We, we had a poster up, a Ghostbusters poster up in our, our war room.

39:38Ryan Olson:Um, and yeah, just, it felt like we were kind of, um, in this, in this war against them. And, uh, and I thought, you know, maybe we, maybe we could win. What was it in your opinion that like, when you look at those two products, what was it that the Instagram version was doing so much better than the Snapchat one? Yeah, I think we, we had a sort of unfair advantage in that people already had their friend graphed on Instagram and the people that they wanted to share with, but we just kind of weren't giving them the right outlet, um, to, to actually do that sharing. And so as soon as we had that, I think it really stopped the outward flow, um, to, to go to Snapchat for that type of sharing.

40:28Ryan Olson:Um, you know, I think we also did push the, the format forward. Um, certainly Snapchat deserves all the credit for coming up with this container that was a lot more comfortable. Um, you know, it's kind of 24 hour, the content doesn't stick around forever. Um, full screen, immersive, all those things. Uh, but at the time there was like a lot, uh, that exists in both stories products today that was not there in Snapchat. So, um, you know, even being able to navigate backwards by tapping left on the screen, like that didn't exist. So I think we brought a lot of nice touches like that. Uh, the hold to pause, something I mentioned in the career notes.

41:12Ryan Olson:So, you know, I was using this early version that we had built and these things were auto playing and they were kind of going by too quickly and just like intuitively put my thumb on the screen and wanted to pause it and it didn't pause. So I was like, Oh, I can just do that. So then I, I built the hold to pause and, you know, now that just feels like a core part of the navigation and the, and the format. Um, so yeah, that, that's another, uh, thing like when I mentor engineers, um, I mean, you just have this power as an engineer to just build your ideas. Like if you are using something and you think it should work a different way, you can just go do that.

41:52Ryan Olson:And that's, that's such an awesome thing. Um, And so I encourage, you know, for sure product engineers, it's like, if you have ideas, just build them and put them out and have people try them. And it's such a cool thing to be able to do. It's insane that you were commuting from San Francisco to Menlo Park. So that's like almost an hour in each direction. And 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. I still wonder, were there times where you were thinking, you care about the work, but that just, as a human, I can't imagine surviving that kind of work schedule.

42:40Ryan Olson:I mean, it probably wasn't 16 to 18 every day, but it was working a lot for sure. and I definitely sacrificed other parts of my life. Like I used to be a very serious rock climber. I was on the US team. I competed in World Cups and I basically gave up that part of my life, you know, for sure in that time. But it was also such a unique opportunity to like be able to build this thing that was just going to go out to hundreds of millions of people. And, you know, one of the things I loved most when I was working on Instagram is I'd be like riding the Caltrain and I'd look over someone's shoulder and I'd see them using the thing I had just built like a week before.

43:26Ryan Olson:And like, that was such a cool experience. So, uh, yeah, it was like, you know, you sacrifice certain things, but I was kind of happy to do so. Uh, definitely not a sustainable model. So I wouldn't, you know, I wouldn't recommend doing that over a long period of time, but in, in stints, it can, it can make sense. And I think by doing that work with that intensity, it paid dividends later on. So the Instagram Stories product came out. It was much better executed, I think, 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.

44:12Ryan Olson:It contributed to its success. I think the reception on launch was very positive. I actually was really worried about it. I thought the whole thing was just going to crash and burn just because I could see all these cracks in it. You know, you, you see the crash reports, you see all the bugs, like you're kind of your own harshest critic. But then when it went out, people were like, wow, this is so polished. And I was like, really, are we using the same thing? Um, but, uh, yeah, it was, it was nice to have that reception. And so I think it helped the product. And then, you know, personally for my career, having kind of demonstrated that I could deliver this project on a tight timeline with this level of craft helped me get onto, you know, the most interesting projects going forward.

45:02I saw at the end of the notes as you started at IC4 at Instagram and you got to IC6 by the end of, after this gauntlet of these projects of whiteout and stories, that's incredible. Like one promo per half, per two halves straight. What was that like?

45:21Ryan Olson:There's a bit of a funny story. So the promotion cycle happened in July. We shipped stories at the beginning of August. So calibrations were kind of happening in July. And so we were in the middle of this like very intense project. And I think like the, there was a lot of recognition of how hard we were working. I think the managers, like they were being cautious around us and I knew, so I felt fairly confident that I'd been misleveled on higher. I just wasn't that familiar with levels when I came in and I kind of looked around and I was like, you know, I'm executing a lot higher than IC4. My Android counterpart, who is an incredible engineer, Will Bailey, he was sort of the tech lead for the whole stories project.

46:17Ryan Olson:And he really like set the example for me of like how you could be a successful product engineer. And he was incredible at getting me into the meetings and, you know, being in the room with Mike and Kevin as we made all the decisions. And so he was an IC8. So I kind of like, you know, he certainly had a bigger role in the project, but we had somewhat similar roles. And I was like, okay, I'm here at IC4, you're at IC8. And so that kind of opened my eyes to some of the leveling stuff. So I told my manager at the time, Eddie, he was the director. So I was reporting the director just because, you know, it's kind of a unique project at the company.

47:01Ryan Olson:And I was like, hey, I think I got misleveled and I think you should promote me from four to six in this cycle. And to his credit, like he didn't just totally brush me off and be like, you know, just dismiss it. He said he actually went and talked to HR about it. And they came back and they were like, we've done this twice in the history of the company. In both cases, it worked out terribly. The people left, you know, very quickly. So he's like, we're not going to do it. But I kind of wanted to seed a little bit that like, you know, probably the correct level for me is a higher IC6. And I knew it was unlikely that they were just going to do that one step.

47:46Ryan Olson:But I had a guess that like, if I was just on that normal cycle, you know, it would come up the next time and they'd be like, well, he just got promoted last half. Like, um, you know, we, we can wait. Uh, and I think it's good for people to recognize that ultimately these levels and promotions, they're an incentive system. I think in the long run, like there's really an effort to make it fair. Um, but there's also an element of like, it's the carrot that's being dangled in front of you. Right. And so it can actually make sense even if somebody is performing at a higher level that like the promotion gets delayed, um, just so that they're not happening in quick succession.

48:28Ryan Olson:So I kind of wanted to like seed the idea that like, Oh, you should probably, probably get me to six pretty soon here. Um, so yeah, they, they, uh, you know, the, the first half on Whiteout, the redesign, and some of the infrastructure stuff, I got the IC5 promotion, and then the 6 came for Stories. It's interesting you say like your high performance. I mean, you know, of course, the promotions are one thing. But one of the things that you took away personally was that it gave you freedom to work on whatever projects you wanted. How does that play out? Yeah. I think it's just like demonstrated that like, you know, if you put me on a project, I'm going to do a good job with it.

49:11Ryan Olson:And so when there is a new effort at the company, you know, it's just kind of a natural, like, okay, let's take the people that have done well on the new efforts before. And, um, yeah, so, I mean, I was very lucky to have the opportunity, but then like executing well on it set me up well for the future. Yeah, you already left before Instagram threads, but I noticed a similar model, which is you pull together all the top Instagram people and you got this small kind of similar like the stories team. And, you know, all those people have proven themselves repeatedly. So, yeah. And it's a very fun environment to be a part of that kind of team.

49:51The next promotion actually came from IGTV, which my understanding, it's like a, I mean, I was at the company at the time. So it's kind of like a YouTube clone almost or like, but vertical video first and Instagram. Could you talk about that project that got you promoted to IC7 or senior staff?

50:08Ryan Olson:So it was very much like, came from Kevin, the CEO, him and Ian Silber, who's another amazing designer. they before like an end of year all hands had um kind of designed this thing together laid out this vision for uh instagram getting into kind of longer form video was was the pitch and it was going to be mobile native so it was going to be vertical the way that you hold your phone and uh so it came actually with like a fairly developed vision to all hands and kind of surprise presented it to everybody. It's like, here's what we're going to do. Yeah. I saw that. And again, I was like, I got to work on this thing.

50:54Ryan Olson:This looks cool. It ended up being a bit of a weird project in the beginning because, yeah, it was like the surprise reveal. If you read through some of the recent antitrust litigation with Facebook, there's some insights into tensions between Facebook and Instagram during this time, like we were told not to work on it for, for a while was kind of like the end of the founder's time at Instagram. IGTV was kind of like the last thing that they were last major thing they were there for. Um, but it was again, a really cool group, very small team, myself, Will Bailey, Thomas Dimson, um, and, uh, you know, kind of like iOS Android and, um, server leads.

51:41Ryan Olson:and then we each had like one or two other uh people per platform and uh yeah just like super talented group um great engineers great designers uh we moved super quickly i mean the product doesn't exist anymore today it didn't it didn't end up doing that well and it's kind of interesting to reflect on why i think like it had some things that uh ended up becoming the future like vertical video is very much a thing today. But it was kind of trying to mix like this 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.

52:27Ryan Olson:We tried some interesting AI techniques to take landscape content and reformat it for vertical. I've got a patent on that. That's kind of one of my more interesting patents. Um, but, uh, we showed that to create video creators and they were like horrified. They're like, you're destroying my content. Like why I've spent so long making this nice landscape video. Now you've just ruined it. So we tried to push people to produce this original long form vertical video. And I think the inventory just never really showed up. And there was maybe a little bit of hubris. It was like, you know, Instagram can just change industry we can just people will just start making this because we have this platform this audience and that didn't totally materialize so i think it probably did inform a lot of like you know what ultimately ship does as reels um but uh yeah igtv itself didn't didn't totally work out yeah i was because i was working on the like video infrastructure team at the time so actually That was one of the things that I got plugged into at some point.

53:35I remember the energy in the San Francisco office and the war rooms, et cetera. Yeah, totally. You mentioned antitrust. And what's the antitrust component you're talking about?

53:47Ryan Olson:A lot of the sort of internal communication has now become public through this antitrust lawsuit where the Justice Department, I think, is suing Facebook to unwind. the Instagram acquisition. Um, and so certain things that were kind of confusing to me at the time, like why, why were certain things happening, um, are less confusing now that I read some of the internal communications that was previously private, including private to me, you know, I didn't, I wasn't exposed, uh, to it, but, um, yeah, I mean, I think basically Instagram, you know had been acquired it was 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 like a peer to facebook and was kind of like the new popular kid in terms of like you know the instagram stories was received better than the stories in Facebook.

54:55Ryan Olson:And so I think that created some tension between the Instagram leadership and the Facebook leadership. And there was concerns about Instagram cannibalizing or taking users from Facebook, um, which, yeah, just kind of guided some of the, the strategy decisions, I guess. I remember that too. Cause I was, I mean, I was also on the Instagram team. And I remember there was some confusion about, you know, why are we turning off the, I guess, somehow like followers are being forwarded from Facebook to Instagram, or it was like cross sharing or something like the direction from Facebook to Instagram was getting turned off or something like that.

55:39And yeah, 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, you know, all of that and all the tensions between, you know, the Instagram founders, Mark and I say he wants to keep them and they're great at building products, but, you know, he's like trying to navigate his side of the equation. Super interesting.

56:03Ryan Olson:It'd be really interesting to know how, you know, how he thinks about it today. That was now seven years ago. Mark or the Instagram founders? Mark, um, because I sense in those communications, like something of a very understandable emotional attachment to the Facebook product, right? This was like 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. Um, and yeah, I just wonder, uh, does he view that differently today than he did now? Uh, you know, seven years on, um, he owns both of these things. Um, I always had the view that like the best, the way to get the best outcome for the overall company was actually to have these things compete with each other because it's like you own both.

57:03Ryan Olson:They're going to make each other better. And, you know, one of them will win versus like, if you don't, if you've kind of stifled that competition, somebody from the outside is like more likely to come up with something better and, and take over. Um, but, uh, yeah, I don't know. I mean, he's the one running a multi-trillion dollar company and I'm not so armchair CEOing over here. yeah maybe one day if this podcast scales up and I ever have Mark on I'll I'll ask him that and then lastly at Instagram I know you started a group called IG labs I'm curious the story behind you starting that group and I also understand this is your promo to IC8 or like director equivalent at Instagram so yeah what's the story behind IG labs after IGTV We definitely spent some time like Thomas Dimson has this phrase like wandering the impact desert, like just looking for for things to do and and not necessarily finding anything great.

58:12Ryan Olson:Um, and I was actually pretty close to, to leaving the company at that time. Um, and kind of the new effort became reels and I didn't feel good about working on like passive video consumption. Um, my manager was, was over the reels org. So it, you know, would have made sense for me to work on it, but I was, I was fairly certain I, I, I didn't want to work on that. I helped the team a bit, but like, um, yeah, it wasn't going to be my project through that time. There was a lot of like culture change. The founders had left, um, you know, the leadership kind of came over from Facebook, uh, the new leadership, um, a lot of kind of like the old Instagram culture, it felt like was being kind of pushed out.

59:02Ryan Olson:and I was talking with like 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 kind of the scope of what we worked on. So, you know, we were very focused on like the existing Instagram app and the existing features within Instagram and just kind of like iterative features on that very like incremental improvements. And I kind of made this pitch that like we have this great brand. We could do other things under the Instagram brand. Like, let's let's go try that.

59:53Ryan Olson:Let's, you know, explore like location ideas, maps, ideas, places. And again, 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. And the idea was just to have kind of this like Delta Force, like small group, very high talent density that would work on new product initiatives and things that just didn't slot cleanly into the org. Like Instagram had grown to such a size where you really needed like a lot of structure in the org just to keep things sane. But that meant that projects that like didn't slot cleanly into one of those orgs were probably underinvested in.

1:00:46Ryan Olson:And so part of the idea of this team was that we would span across, you know, we wouldn't have a focus area. We could kind of work across many things. Um, we, we tried a lot. I mean, a lot of it didn't ship or tested, um, probably one of the more lasting impactful things that it seems small, but I think it actually gets used quite a bit as the collaborative post feature where, uh, you can have multiple authors on a post. Um, it's another of the more interesting patents I have is, is on that one. Um, and, uh, and so, yeah, I think, I think we found good impact. And then we were also this concentration of talent that like when there was a new important initiative ultimately ended up being threads, um, you had this group that, that could go work on it.

1:01:34Ryan Olson:And, uh, and yeah, just trying to, uh, I don't know, kind of encourage innovation, trying new things and, and push that at the company. The last thing on your Instagram journey was that you tried management at some point or as an ICA, you switched to, I guess, TLD or tech lead director. Well, what was your thinking behind that and how'd it go? It's a very unusual or rare role within Facebook. Even like TLM, I think it's quite rare or was at the time. Then like tech lead director, probably even more so. Thank you. 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.

1:02:34Ryan Olson:You know, I could probably represent them better in calibrations. I mean, I was in the calibrations anyways. So it was kind of like doing a lot of this work. So, um, yeah, in some ways it was just kind of like a formal recognition of like what I was doing already, um, to, to have these people report to me. Um, Facebook is, is very much of the school of thought of like individual contributors and management should be separate. And I don't subscribe to that. Um, other companies work differently. Like my wife is a senior staff engineer at Tesla and like, um, they're very flexible. It's like, I see, have people report to them all the time.

1:03:16Ryan Olson:Um, managers are expected to be like pretty competent, uh, technical contributors and like doing individual contributions. Um, and I think I prefer that model. Um, and so it was interesting for me to, to try it. I think like another one of my sort of controversial opinions is like, I think senior engineers should be involved in coding. Um, there's overlap between that thought and like the thought that like, um, managers should be still somewhat involved. There's, uh, an author. I really like Nassim Taleb. Um, and he talks about having skin in the game and um yeah i think like if you're a senior ic who has to do some coding like you have more skin in the game like you're not going to come up with some architecture that like you just hand off to somebody else and it's their problem now right like you're going to be involved you're going to see more hands-on what the issues are um and i think like similarly if you're managing a team and you're much more like with them in the day-to-day stuff, I think that you will operate better.

1:04:31Ryan Olson:So yeah, it's maybe a bit against the grain at Facebook, but it was a philosophy I had and I wanted to try it out. And then 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, right? So you're just a software engineer through your whole IC time. And in some ways I like that for like engineering discussions that there's no like pulling of rank, like, hey, I'm more senior, you know, just take my idea. Like it's a little bit more meritocratic perhaps. But in cross-functional situations, say you're working with like a PM, like I'm trying to ship this, collaborative posts thing.

1:05:21Ryan Olson:And I have to like meet with PM, all these different PMs on these different teams. There was an element where having a little bit higher of a title, I think just made those conversations easier. Like I had a higher baseline where they were like, okay, this person, like maybe they like know something they've been here a bit. Like they're not just, you know, totally new. And, um, you know, you, you build up some reputation in a company, but when it gets so big and there's new people joining all the time, like you're actually having to like reestablish that a lot with, with folks. So, um, yeah, I think like it, it, it was somewhat helpful to have that title.

1:06:03Ryan Olson:There would be discussions in the, in the senior engineering group about like, should, should there be some form of, of public levels, um, within the company. And I was supportive of like maybe like a two, maybe not like the full level is, is public, but like there's like a senior designation or something. Um, just, uh, yeah, I think largely for like when you're working with people outside of your normal working group so that they start from a slightly better baseline on, you know, whether, whether you know what you're talking about. The number one thing I hear people say is that this is not optimal because it's you're doing two jobs at once and you're going to drown and your career will not flourish in either direction.

1:06:51What do you say to that? I think it's probably correct.

1:06:54Ryan Olson:Like at that point, I was really not optimizing for career. You know, it was never my intent to stay long term. uh i mentioned this in the career note like facebook does these internal employee sentiment surveys every six months i think or year and one of the questions on there is how long do you intend to to stay with the company i never put more than one year like it was always like okay this is my last year i'm gonna i'm gonna get out soon um and so yeah i think like i didn't have aspirations to get to IC nine. Um, and so it kind of freed me up where it was like, you know, um, well, I don't want to get fired for performance, but I kind of knew I wasn't going to get fired for performance.

1:07:45Ryan Olson:Um, and so, yeah, there was just a little bit less pressure on that. And, um, yeah, so I could just kind of like do the thing that made sense for our group, our team, um, and, and worry a little bit less about the career stuff. But yeah, absolutely. I think like I saw firsthand, like I think my ratings were probably lower than they would have been if I was just an IC maybe. It was like, okay, you're exceeding as an IC, but you're meeting as a manager. So you're just meeting. That's kind of like the full journey from start to finish of Instagram. And 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 that I kind of recognize in Instagram as well.

1:08:36I'm curious, you know, what made you want to leave to start that? What's the story behind creating retro?

1:08:42Ryan Olson:So around the last few months of my time there, I was talking with Nathan, who's my co-founder. We had worked on stories together. He had gone over to the Facebook side. He started Facebook dating. And then he was working on some of the virtual reality products. And 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. And we really wanted to be in the driver's seat of that. And we would talk about starting a company, but it was always like the timing wasn't right for me.

1:09:28Ryan Olson:I was on a project that I was engaged on and then I'd be like, okay, I think I'm ready. And he was on something new. Um, and so finally our timing kind of aligned, um, where we were both ready to leave. And I had a conversation with, um, this investor friend, the same one that connected me with Flipboard, who's, he's kind of a mentor of mine. And he was like, it's time. You should really take a bet on yourself. And that stuck with me. I was like, yeah, I should like take a bet on myself. And so we left to start the company. And actually our goal with the company is really to create this world-class product studio.

1:10:10Ryan Olson:And Retro is our first product, but it's not necessarily like the reason for the company existing. And we, yeah, we just want to kind of create this 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, and also to create a successful business. So retro is our, is our first product and it's a social app, but it's actually quite different from what are called the social apps today, I would say in that it's actually social. So you, you, you see people, you know, on it friends it's, it's all focused around friends.

1:11:00Ryan Olson:And you know, I'd say like the traditional social media is maybe, well, the derogatory word I would say is like brain, brain rot media. Um, entertainment is maybe like a more favorable term. But if I open Instagram today, I don't see a lot of the people I know. Um, even if I actually go to seek that out, I tend to end up down a rabbit hole of, uh, kind of short form video, entertaining content. And, um, it's definitely entertaining, but it, it kind of hijacks my attention. I get sucked into it. And so 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 kind of picking out the highlights.

1:11:52Ryan Olson:And in some ways, it's a throwback to kind of 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. And 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. So we've been working on that for the past few years. It's become very popular in Taiwan. Oh, interesting. is not something we expected, but, um, you know, social networks are so much about the network, whether your friends get on it.

1:12:38Ryan Olson:And we, we managed to hit the critical mass in Taiwan and sort of all of the usage patterns end up looking different when, when you hit that critical mass. Um, so we were number one on the app store there for a period last, uh, last year. Um, and we still are at the top of the, of the photo category. We were number two when I looked this morning. Um, so we've kind of shown that like it, when it works, it works. Um, and we had just have this challenge of making it work in more places. And, um, it was very challenging to get people to try a new app. Um, but if you miss seeing your friends and people, you know, on social media and staying connected with them, I, you know, very much encourage you to, uh, to try out retro and, uh, and yeah, it's, I, I think it's a really delightful app.

1:13:30Ryan Olson: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 philosophy you went for with this app, is it more challenging to get people to use it because it's less addictive? So one of the key decisions that we've designed around is that we don't have an ad based business model. And I actually, I don't think like 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.

1:14:25Ryan Olson:Um, you know, 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. Um, even past, you know, what you wanted to get out of the app, I show up to see what a friend is doing. It's going to try to keep me there for the next hour, two hours, whatever. Uh, and so I, I think ads fundamentally kind of like when combined with an algorithmic feed, uh, make products that aren't super aligned with people. Uh, but there, there is definitely a challenge, uh, in terms of like growing retro. So, you know, we don't have, uh, creators, the, the model is mutual friending.

1:15:13Ryan Olson:So, um, 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. And we have a limit of 250 friends. And so you can't build an audience on this platform. And so a lot of the ways that like Instagram grew was through creators that were financially incentivized to spread this app and get more followers. And so those pathways to growth are not open to us. Um, but we've, we've seen examples of like, you know, be real, uh, managed to get a decent growth. They had kind of a nice viral, um, mechanic built in with this notification that everyone got that was weird.

1:15:58Ryan Olson:It's time to be real, you know, that created a lot of conversations. So that certainly helped. Um, but I think it is possible to, to grow a friends only, uh, social network, but in many ways it is, it is harder. And also the business model is harder. That's something that we're very open about. Like this is a 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 very much taking an opinion on what this product should be and what we want to see in the world. Some people say just build what people want. And, you know, maybe you could say like in Instagram, people are demonstrating that it's what they want because they spend more of their time there.

1:16:47Ryan Olson:And we're taking a little bit more of an opinionated stance saying, no, we think like, actually, that's not great. And this is better. And even if it's more challenging, something we strongly believe should exist in the world and should be an option there for people that want it. I think we also actually coexist really nicely alongside Instagram. Like I still have it. I still open it, but I'm getting sucked into it a lot less and it's helped me kind of break this like phone addiction that, yeah, I just didn't feel good about. How do you monetize if you're not using ads? We have a subscription, a premium subscription.

1:17:25Ryan Olson:And so 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. So video, as you know, from video infrastructure, like the storage and bandwidth for that is quite a bit more than than photos. And so you have to subscribe if you want to share out video. But the free version of the app is like actually great. You know, you can share photos. You can remember your own life. And it's like 93 percent of what people share on retro is photos anyways. ways. And so, yeah, if you want to kind of like support the mission and get those extra features, you can become a subscriber.

1:18:11Ryan Olson:That's awesome. I love like the intention behind it and like the mission. It's really cool. It's definitely a product that's fun to work on. It feels good. Like, yeah, it's very, very feel good. We had a tagline for a while, like feel good social media. it. And yeah, it's very much that. Coming from big tech and starting your own company, I'm curious, like looking back on, you know, across the various career axes of maybe like, you know, learning, satisfaction, compensation, you know, the things that people look at for their career, how has it been so far working on your own thing? Yeah. Compensation is quite a bit worse.

1:18:53Ryan Olson:we we pay nathan and i pay ourselves less than all of our employees and we have more ownership in the in the company which i think is the right way it's how it should be um uh but that means that yeah i've you know kind of um certainly put off that short-term compensation we hope to become a very successful company and that that equity is going to be worth a lot both for us and for our employees it was always the thing i wanted to do like i i was a bit surprised actually that I ended up in, in, in big tech, you know, talking about like those early days in, in Flipboard and, um, kind of this like entrepreneurial culture, like it was always exciting to me.

1:19:33I would read tech crunch all the time, um, about the new startups and, uh, yeah, I just

1:19:39Ryan Olson:always wanted to kind of build a company, you know, be able to, to bring the best people together, work on the things that we thought were cool, um, do the things, do things in the way that we wanted to do them. And, uh, yeah, it's been, it's been awesome for that. Um, and, uh, and definitely like have 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. Like a lot of my work became kind of like convincing, uh, you know, layers above me that we should do something. I, I would say there were probably more people working on that app than there needed to be.

1:20:28Ryan Olson:And so actually there was a lot of gatekeeping, um, where it was like, is your team allowed to ship? So you would do this work. And then there was like, you have to convince somebody that like this is a good enough thing for to ship in the product which is understandable because you know it becomes very complex if you just let everybody go but it means that there's a lot of work in just kind of like that political wrangling and like how do i how do i make this person feel like this is their idea not my idea um and and i'd spend none of my time on that now um you know we we do a one hour standup, uh, every day.

1:21:09Ryan Olson:That's basically the only meeting, uh, on my calendar. So, um, I get almost the whole day to, to just, uh, build, think about, you know, what people want and try to make it. Um, so, um, yeah, I'd say like satisfaction is definitely higher. Um, learning is definitely higher. Compensation is definitely lower. I think throughout the conversation, you mentioned that, you know, smaller teams can move faster. Do you think that the company would be better off if you just like laid off half the people? I would say yes. We used to talk about this a lot when the company was much smaller. Like this thought experiment of like, you know, the Thanos, like you just snap your fingers and Like half of people are fired, even if it's a random selection, um, do things go better?

1:22:02Ryan Olson:And frequently we felt like, yeah, maybe I think they would. Um, so yeah, um, I mean, it's tough because with a business like Instagram, you know, if you can make a 0.1 % improvement, it's actually like hundreds of millions of dollars to, to the business. And so sometimes, you know, that incremental person, maybe they they're able to find those things. But I think it's less appreciated the cost of each person you add. And there's sort of like maybe the more obvious just organizational communication overhead. You know, you just have more stakeholders, more meetings, more coordination. But even just like writing more code, like having more code in the app.

1:22:53Ryan Olson:I remember right before I left, they had this tool where you could see how much time you were spending compiling the app. and I was spending more than four hours a day waiting for the app to build just because there was so much code and you know the tooling just had not kept up with basically the the velocity at which people were writing code and so that's a huge cost that's kind of you know it's not noticeable with each incremental person you have but now you have this you have a thousand engineers And all of a sudden, like everyone's just like so slowed down because, um, yeah, because of this overhead.

1:23:37Ryan Olson:So, um, yeah, with a, with a smaller team, you know, like when we were 10 people and the app was tiny, it was like so much easier to get things done. Like a project, like, like whiteout, um, you know, would be like a massive project for Instagram today because there's so many more surfaces or so much more code. There's so many more people. was actually like a lot easier at the time that I did it. Yeah, I guess, you know, Twitter is kind of an interesting case study of that because they kind of went through that and the app's still operating. I do get the sense that there's a lot more breakages, but I'd be curious like on the product development side, you know, is it, how has that been being on those teams?

1:24:20Ryan Olson:Totally. Yeah. I mean, I think there were projections when Elon came in And I think he cut like 80 % of the staff or people left as well. Right. That like, oh, this thing was just going to a hundred percent fall over. And I mean, my experience is somewhat buggy. There's definitely some issues. But I mean, you know, it's very much continuing to run. I think also I saw like the economics of the business have actually become much better. it's actually profitable now whereas you know through almost its entire history it was operating at quite a loss and so yeah somebody coming in and and with a machete cutting things like maybe it's okay.

1:25:10Towards the end of the conversation I just want to wrap up with a few career reflections I think first thing is you throughout your projects you worked with like a lot of very talented people. I think you mentioned, you know, Thomas Dimson, Will Bailey, a few incredible designers. Also sounds like you worked with the founders of Instagram. And I'm curious, do you have any stories that you'd share that illustrate what made them exceptional?

1:25:36Ryan Olson:Mike Krieger is definitely something of a hero of mine. And it was like such a privilege to get to work with him. They say like, don't meet your heroes because you'll be disappointed. But I think like you should meet Mike Krieger. He's, he's actually an awesome human. And, um, a lot of the ways that I think about engineering leadership and engineering philosophy came from him. Uh, so I mentioned earlier, the simple thing first, you know, that's really stuck with me. I think the attention to detail and craft. Um, but 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, or I call it like lead from the front way of operating where he never put himself above the team and he would just jump in to whatever team if an effort needed help.

1:26:33Ryan Olson:So at the end of stories, I had brought in a friend of mine from Flipboard actually, who was then working at Facebook, not at Instagram, very different team to do the drawing tools just because he had worked on a drawing app before. And I was like, Hey, we need drawing. Like, can you work on this? Um, it's kind of an interesting insight into like how Facebook operates that I could just like go to this random, you know, person on a very different part of the Oregon and pull him into this project. Um, so he worked on it for a few weeks and got it reasonably far, but, uh, then kind of got pulled back by his team.

1:27:10Ryan Olson:Um, so we were in, we were in a bit of a pickle and, um, Mike just came in and was like, okay, well, I'll finish it. Like, um, so he, you know, he's in there coding the, the neon brush and, uh, you know, we were working those insane hours. He was there working with us. Um, he's up at 2 AM reviewing my diffs. Um, and, uh, yeah, just seeing that and how that felt as a team, uh, really has informed like the way I think about leading teams. Um, and, and so, yeah, that he he's, he's awesome. Um, some of the other folks you mentioned, Will Bailey, I talked about him a little bit But before, he has just this product vision that he sticks to very strongly and frequently it's quite good.

1:28:05Ryan Olson:He, at the kind of like, I would say like dark days of development of the stories project when it was spinning in circles, it was taking different forms. None of them felt very good. He just kind of outlined this full vision in a document for like how this product should work. you know, the things that we could do with it going forward. And I looked back on it five years later and I was like, wow, this was like the five-year roadmap for, for what we ended up doing. Like he basically nailed it all from the start. And, and yeah, he was such a good example for like how you could succeed as a product focus engineer, which actually was fairly, it was much more of a thing in Instagram than it was in Facebook.

1:28:52Ryan Olson:I remember being in bootcamp and people were saying, okay, if you're junior, you go work on a product team. And then if you're senior, you work on an infrastructure team. And that was kind of the culture was like, you know, product is easy, but like, you know, real engineers, they work on infrastructure. And, uh, and Instagram actually prioritized more in some ways the, the product side. And I think that was reflected in, you know, the various versions of stories, for example. Um, and so Will was such a great kind of mentor and, um, example of like how you could have the successful career as a, as a product engineer, um, how you could influence product direction as an engineer.

1:29:37Ryan Olson:And then Thomas is, uh, it's probably just like the smartest person I've ever met. Like he, he, He's incredibly smart, but not in like a savant kind of way. Like he's also like, you know, got great social skills and understands people. And so he did the feed ranking or, you know, basically started all the ranking at Instagram. He started his own company, OpenAI, bought his company. He's a researcher there now. Maybe Zuck's coming to him with a million dollar offer. I don't know. Um, but, uh, but yeah, I, again, like, you know, he actually had like this skill on the infrastructure side, um, you know, built a lot of the infrastructure for the ranking stuff, but always approached it with a product mindset.

1:30:29Ryan Olson:And I think would probably consider himself like a product person. Um, I have always been interested in technology as like a means to create things for people. Um, I've never been that interested in like the technology itself. Um, it's like only interesting to me, to the extent that like I can create interesting experiences for people. Uh, so yeah, I think like, um, Thomas and, and Will, um, you know, kind of had maybe a similar approach, very like human oriented, um, thinking about the psychology, how people use these things and how it makes them feel. And then your last question is if you could go back to yourself after all this experience that you have and talk to yourself when you were just graduating college and give yourself some career advice, what would you say?

1:31:28Ryan Olson:Like just invest in the tools of your time to build things for people, like build products for people. And I think if you, if you do that, you'll be pretty flexible and adaptable. And in many ways you have a unique opportunity as a new grad because you, you aren't sort of stuck on this path of like, I'm, I'm an iOS person. I know this technology really well, like it's all new to you. And so you can pick up the latest thing. Right. And so I think like with these AI tools that are coming out, um, you can do incredible things with them and you're probably going to be more skilled at those than the senior engineers.

1:32:10Ryan Olson:Um, because it's just not the thing that they, you know, learned natively that they've invested their time into. And I had that to some extent with iOS where it was a, it was a newer thing. And so like the senior engineers were like writing Java or something, you know, they were running our backend and I could actually stand out and Excel on this thing because it was the first thing I learned. And, um, you know, I was eager, hungry. And, uh, I think there's, there's something to that with like this new set of AI tools. So yeah, I think my advice for new grads, just like, you know, learn the tools of your time and, and, and get good at them and, and make things, make good things for people.

1:32:51Ryan Olson:And I think, I think that will work out. I imagine it's, it's a bit scary probably because it's hard to say how it's going to play out, but like, it seems like there's reducing demand for like junior software engineers because of some of these AI tools. But I think if you can yourself get really good at using those tools, there will definitely be roles for you. Awesome. Well, yeah. Thank you so much for your time, Ryan. And I was really, you're a legend at Instagram and I worked there for so long. I'm super excited to talk to you. At this point, is there anything you want to redirect the audience's attention to?

1:33:26Ryan Olson: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 into their lives, but maybe they've stopped posting on social media. So get them on too. If you're a designer, you're an engineer, definitely reach out. I think we have some interesting ideas in how we're building this company. I mentioned before, our goal is to become a world-class product studio, multiple products. We have Retro, but we have two more in the pipeline right now. And I think we have some interesting ways we're structuring revenue you share with employees.

1:34:09Ryan Olson:So as these apps start to make money, even if the company's ambition is to kind of like take that and reinvest it into growth, you can see some of that upside right away. And we're building infrastructure that helps support products across the portfolio. So we're building growth tools, analytics tools, all of that, that I think are going to really help us Excel as a product studio. So if that's interesting to you, you know, reach out for a conversation. And yeah, it's just been a pleasure chatting and thanks for having me on. Thanks so much, Brian. Really appreciate your time. Thanks for listening to the podcast.

1:34:47I 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. and if there's any guests that you want to bring on to please let me know i feel like sourcing very senior ic's there's no well studied list out there on google that i can just search this up so 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