Quitting the Plan: How One Developer Reinvented His Career from Scratch

In this video interview, I sit down with Simon Stern, who started off as a self-taught developer, moved into being a boot camp instructor, from there had gone into big tech, and is now looking at things from the entrepreneurial perspective. So, I think it's really cool to sit down and talk with Simon through this because we get to see a different perspective that I don't think that I generally capture in these interviews. I think there's a lot more to software development than just coding and and all that kind of stuff that we normally go over and that really starts to kind of come through in this conversation. So, I think that you're really going to enjoy it. So, sit back, enjoy, and I'll see you next time. Simon, right before we started recording, I had said career journeys. Um, one of the things I love asking guests about. So, if you don't mind, as early as you would like to kind of go back in time or is laid up to you, if you want to give us a little bit of background for who you are, where you started, and how you got to where you are currently. >> Uh, yeah, for sure. Thank you. Uh, thanks for having me first of all. Really appreciate it. Um so my career journey is relatively sidewindy. Um I graduated with a degree in biochem and originally my plan was to be a doctor going into medicine and I spent two years working as a research uh assistant and scientist uh after graduating and I found out like I hated every part of that life part of that job. I worked for a doctor. He like pulled me aside one day and he's like don't go into medicine. He's like, "If you value your your life, don't go to medicine." Um, and it really struck me. So, um, I kind of had this one day with some friends where we all got really drunk together and it was like the theme was like, "What is Simon going to do with himself?" Cuz I really >> they they came together and this was the event for for you to >> kind of I just invited some buddies over and I was like, I think I'm going to quit my job and also my entire career path. um let's get drunk. And they're like, "Okay." And >> because that's not a that's not a small thing, right? That's like you if this up to this point you're like, "This is what I'm doing." And now all of a sudden it's like, >> "No, now it's not." But what is what is >> for like all of high school, I sort of had that plan and um so it was like eight like almost 10 years actually from from being a kid and um like working in the field and I think yeah it was it was pretty tough. But two weeks after that night, um, I basically booked a actually the next day after that night, I booked a one-way ticket to Australia. And that was my answer to that question. Um, and then 2 weeks later, I was in Australia. And with no job, I'd quit my jobs and was just kind of like, okay, I'm just going to live here for a bit and kind of reset. And when I was in Australia, I had um like 12 different jobs. I lived there for a year. I was a brick layer, a truck driver, uh a cleaner, a driver. Um I cleaned up a racetrack for a big race. Uh I managed a carnival or helped manage a carnival. I I did all kinds of crazy things. The best job was delivery driver by far. Uh and because it's awesome. You like are just kind of on your own listening to the radio outside all day. Um I got very fit. Uh and on that in that year I decided I'm gonna when I go home like what do I value? I value kind of my independence as much as possible and I value having like some sort of skill something that actually is a tangible skill which >> for a degree in biochemistry you don't actually get. So you get like a bunch of knowledge but it's like very weird esoteric knowledge that is only useful in very very like niche verticals that are not well paying. So >> interesting. Okay. >> It sort of led me to software development. I decided, okay, when I'm done with this year, I'm going to go home and I'm going to learn to code. And um that's what I did. I went home after the year and I started with JavaScript. I learned about um APIs. I learned Angular and a little bit of jQuery. jQuery was was not working for me, but I learned Angular and then eventually React and um slowly kind of built my way up from there. Like it's it's kind of a funny story. When I started, I had one friend who had a brother who worked as a dev. Nowadays, everyone's a dev or at least it feels like there's devs everywhere. But at the time, I had zero technical friends. Uh all my friends were in med school or trying to go to med school. So, >> okay. >> Um one of those friends, her brother was a dev. And so I asked him like, "Hey, can I just like hang with you and and just kind of learn from you?" And then that turned into me being like, "Hey, can I like go into your office at your workplace?" And kind of ask them and just see what it's about and like like I I knew nothing about what a dev was coding. I started going to every single meetup in the city. Uh luckily there's a lot and and just asking and and seeing like is this something that is approachable? Um, and so I went into my friend's office and they were like a studio, so it was kind of perfect. They had lots of different projects. And after the first day there, and they were cool. They were like, "Yeah, come like see what it's all about." And then after the first day there, I was like, "Can I come back tomorrow?" And the next day, and I basically went in for 3 months straight, 9 to5, um, treated it as a job and eventually they're like, "Hey, like do you want to try adding some code to this feature?" I'm like, "Sure." Then they're like, "Okay, do you want like a little internship?" And basically after six months I uh after three months I had a job there and then after 6 months like a proper full like junior dev role and the rest has kind of been history. I I eventually started my own agency. Um and then I got a really cool job that I did for the last 5 years uh for a big pharma company in the states and really really enjoyed that React Native role. That sort of became my my bread basket was React Native. Um, and then this year I decided that I really want to try something new because I sort of had been like kind of like scrambling to be in the business and then to stay in the business and then I had this great job and this year I'm like okay let me like really reset and um I have been building like my own apps and kind of exploring different ideas and um I lived in Malaysia for 3 months. at network school which if you know what that is it's like biology >> not no >> so the former CTO of Coinbase Bji Shanasan is like this big crypto um personality on on Twitter and he started a he he sort of believes that there's going to be like this >> um like as as societies get more and more unstable people want like smaller communities so he started like a startup society in Malaysia And yeah, we went me and my wife went to go live there for three months and met met founders from all over the world and kind of we all like pitched together and like worked on ideas together. >> Wow, that's really cool. >> Yeah, it was that was like by far the coolest thing I'd ever done. I got to like meet um Bology and and kind of hang out with this guy a bit and all of these like really hardcore hardcore people. I met like Vitalik, the founder of Ethereum and uh >> all kinds of people. So yeah, and then that's what I've been doing. So now I'm kind of like building um my own apps with some friends and trying to make that work. It's definitely humbled me. It's very very difficult to make money on the internet. >> And I have I have some questions on that because I think that that is uh I think for some people it comes very naturally and for other people like I know for myself absolutely not. Like I if you told me before we got on this call you're like I have a problem doing this. If I had the perfect coded solution to to give you and I'm like and it costs even a dollar, I would feel very uncomfortable being like, I'm trying to help you, but it's only a dollar. Like I everything about that interaction would feel very gross to me. Like I don't know how to do it. And that's something I have to get better at. But that's like I think some people really find it easy and they're like no problem. Like you need me to talk to someone to sell something? I got this. And other people are very much like kind of like me where it's like no. >> Yeah. I've sort of learned that. And it's it's sort of interesting because I've also seen like my voice, my ability to like talk to the world as it needs a lot of work basically. Um, and I think selling things like I I can make stuff, you know, I've learned how to build things and I like to build kind of I I try and I try and build things that I find interesting, but um I find communicating the second I put it out in the world, it's met with like a what like what is that? Why do I want that? Why do I need that? And so it's an interesting case of >> um not building to the market or building to maybe there is a market but like not being able to communicate with that market. So that's been my learning and very humbling learning. >> That's very cool though. That's awesome. I have uh a couple of questions about about your career journey that I think would be uh helpful to to kind of hear your perspective on because one of the things you said uh when you're kind of doing that transition into coding was you talked about the different things that you kind of just jumped into where you're like I got to go learn this. I'm you know going to go learn this that I'm going to spend time doing that. For some people, and I feel like for for arguably most people, it's like people are aware they're like, I need to go learn a language. I need to learn a tech stack. But the act of going through the steps and spending time doing it, that's it's a pain in the butt. And it's like a lot of the time it could be demotivating. It can feel like, you know, anytime you're trying to pick up something new, you're like, I'm back to a newbie. Like I it's it's just uncomfortable putting yourself through that. What if you I don't know if you this is something you've reflected on, but like what um what kind of drove you during that time where you're like I got to do it or or was it just a pain in the butt the whole time and you kind of just made it through to the other side? >> Uh yeah, that's a really good question. So it was sort of like I had to do it or I had no other option cuz I felt like the world of going back to being like a clinical researcher or working in a lab just felt so just that door was closed to me like I couldn't go back. um I didn't have any other kind of skills but this was something I knew I it it was sort of like you it's it's very deterministic like if you learn this you can get a job doing that and that was like very comforting to me so I just decided like and I made it very project based so I actually also spent like a year and a half as a boot camp instructor and I kind of have a lot of opinions about boot camps but this was like pre boot camp and it was very project based cuz even right at the beginning I was like oh like I'm on Twitter a lot so I want to build like a bot that organizes different Twitter groups or lets me do that and I didn't know if that was a possible thing to do but I just started building in that direction and basically until I'd exhausted that idea or exhausted that direction but really basic stuff like okay how do I show a list of tweets how do I style that list of tweets >> you know I want to click on one of those items in the like these are things that would take me days, but it felt and it was it was painful like it was wake up, do this, do it until 9:00 p.m. at night and then know what you have to do the next day. Um, but I I did feel a very strong sense of like I can see the finish line, >> right? >> And that would that kind of kept me going. This this year is very very different because it's you can't see the finish line. There's like it's it's not as obvious. there's certain steps that you can do in >> um like outside of writing the code, but it's uh it's a different kind of thing. Yeah. >> Yeah. And I think for different people, they'll have different motivators, right? So what you're describing is like at least from what I'm hearing is that if you know there is a finish line and you and you believe that there are a set of steps to get you there, it's like okay, the steps might not be easy, they might not be fun, but like you're like, I can get through these steps if I keep putting in the time. I'll just keep doing that. And uh along the way, you can feel and see that that finish line is approaching. So like that that's like a I don't know like a good sort of feedback loop for you to be like it's moving in the right direction. Whereas for different people, they might say like maybe that finish line isn't so obvious because they're like I'm told that this is supposed to happen. I don't see it getting any closer. And then getting that that motivation could be more challenging. But I I think that's really cool to hear that that that really clicked for you and then you were like, "Okay, like I got to put in the time and and do it." Um the I I don't think for everyone, but I've definitely seen like a theme and I feel like this is kind of human nature where it's like, you know, I hey, like I did the tutorial and like I spent the week doing this and like I don't know, I don't have a job yet and like, you know, I was kind of expecting that I had to put in my week or my my month of coding and it's like it doesn't quite it's not quite that easy. It's not like you just, you know, do it for a little bit and then it all just falls into place. It's like this for some people this takes a very long time and >> that's kind of uh kind of normal and I think that maybe as as humans like we're very much like what what is the shortcut right? You've done this before so like tell me the shortcut so you can save me all this time and I think that sometimes it just really doesn't work like that. It's got to put in the time and the effort. So >> yeah. Yeah. I I find like it's also kind of changed a lot since then because uh then boot camps uh proliferated and sort of sold this kind of fake dream, fake promise like 3 months and then you get a tech job and um I worked at a boot camp for a year and then I worked at the uft boot camp which was uh unfortunately like just worse and I think there is definitely this sense of it was it was very different um the expectations and sort of the way that people approached it. Um, I think because of that structure, it almost like the incentives were all misaligned where like for me like I had to make that job work or I wasn't going to have a roof over my head. I was very much like backed into a corner, but I think it became this false promise of like, oh, 3 months and then you can get a tech job. And I just don't think it's ever worked that way. I think you have to like fight for your life for anything that is worth having. And you know a a six figure tech job that you can work from home tapping away at a computer screen is like that's a big deal. That's that's actually a really you know it's a very like prestigious like nice quality of life that you can have for yourself. So, um I I do believe that trying to sell that as like an easier thing to achieve kind of watered down the the whole the whole kind of industry suffered from it. I think there was like too many people now at like a skill level that was at the tutorial stage as you said which I've I don't really I don't believe in tutorials too much. Like I think they're a good way to, you know, learn the API or like the syntax of a certain feature, but you have to build your own thing. You always have to build your own thing. And that is the only thing that will actually like teach you. >> Yeah. And I and I it's funny. I fully agree with that. As someone who makes a lot of YouTube videos that are a lot of tutorials, I'll have people that will say like, "Hey, like we're like, can you give me the code for that?" And I'm like, I I actually don't want to. Not because it's extra work to do, but like I don't want to because I don't think that that's actually going to help you in the way that I've intended. Like my goal with the tutorials is like there's some where I'm like if I can unblock you doing something great. Uh but ideally it's just to get you thinking about things. Like I don't I don't want to give you the stepby-step thing uh you know on repeat for all of these things and kind of make it feel like a false promise even with tutorials. But um yeah, I I I I think I I agree with the boot camp um points you're making. It's not I'm not like I don't think boot camps are a terrible thing, but I think that a lot of them started kind of being a little bit misleading with the expectations. And I don't think that that's fair. Uh I think that there are plenty of people that have gone through boot camps and that absolutely accelerated their learning and their skill sets and that that is great. But to tell people do this for three months, you will get a six-f figureure job. I'm like, you can't guarantee anyone that unless you're the one hiring them after for six figures, then >> then sure, guarantee whatever you want. But if it's not you, then like that's just not it's just simply not fair and it's misleading. So >> yeah, and I do think it I mean it's it's there's a lot to be said about accelerating your learning and a lot of really successful colleagues I I know started in a boot camp and then they were very >> something about like coding um drew them in and it's always interesting to me when I meet people from like really different backgrounds. I think cuz of my own very different background who you know I have a friend who was an architect and then she really liked design and um she got into coding and found the design like saw the design in code and would never have made that connection you know but uh stuff like stories like that are really interesting and then those people always go on to make like really uh impressive things and and aesthetic things because they have that outside like idea for it. >> Yeah. they bring different perspective into what they're they're building in code and I yeah that I think that's super cool. It's one of the things like when I talk with guests especially that have sort of come from different backgrounds um or had careers for a while in something and you know whatever life event and they switch over um I think the perception is that it's like oh well I'm starting late I'm going to be worse I'm disadvantaged and like sure you're starting late compared to someone who was coding at a young age and that's that's one thing but you're also bringing in completely different perspective completely different skill sets and It's not like those are zero value. In fact, those can be, you know, tremendously valuable compared to what some other people kind of have in their uh in their skill sets from purely focused on on writing code. So, I think um yeah, the more people I talk to, like one of my goals with with doing sessions like this is to is to kind of expose some of that to be like, see, like this person wasn't coding when they were 5 years old and like things are going pretty good. Like, it's okay to have a different journey. >> Yeah. No, I I I totally agree. And it's interesting nowadays, too, cuz everything has kind of been flipped on its head with vibe coding. I'm curious what your thoughts are on on that as someone who like makes this kind of content with career journeys, tutorials, like how has that affected your perception? >> Yeah, it's I I think it's interesting. I have a handful of different perspectives and I think the the challenge right now is like given that it's early. Um my one of my like sort of philosophies in general is like I try to keep an open mind about things and try to challenge my own perspective from different angles. I might have a strong opinion about something but I'm like I if I don't have it backed by like data then I'm like I I must keep an open mind. So to give you an example uh with like vibe coding uh I think there are absolutely opportunities to leverage it that I think work really well um and might vary from skill uh from skill level. So for example, I've been programming for a long time. I will vibe code things that like I don't have a genuine interest in spending time learning right now. Uh, sometimes I vibe code things where it's like um to give me a little bit of a a preview of what I'm going to do in a good I'm trying to think of a better way to explain this. It might be something I want to learn about some of the videos I was making recently for YouTube where in C we have uh the Rosland compiler and we can build analyzers that do like static analysis of code. I'm like, I wanted to learn about this for forever, but I simply have not made time to go do it. So, I vibe coded a bunch of these because I needed some. Now, I'm at this point where I'm like, "Oh crap, I don't know how these work and I have a bunch of them in my codebase." So, like, I should now like go spend time like learning about them. They're operating, but that's fine. But that the skill level I have in my experience, I feel okay doing that. That I'm like I'm not in a spot where I'm like, "Oh crap, I'm screwed." Um, I get a little bit more concerned when there are people that are more junior vibe coding that um, they're not taking the opportunity to try and learn what's being produced. So, they see it as a way and I don't mean to I'm not saying all juniors do this. I'm just saying this is a sort of one of the trends that makes me a little nervous is yes, you know, you can use AI tools to produce code. That's great. But if your sort of pattern is produce the code and then produce more code and produce more code and every step you're like further and further away from understanding what's going on, that part makes me nervous. Um, so the the the point I want to bring up about challenging my perspective on this is I don't think that that's a good approach personally for someone who's more junior. I think that you should be trying to you know as soon as you don't understand something go talk to the LLM ask it questions ask it to explain things that's what I would recommend so you understand some of the fundamentals but the thing I want to challenge my own perspective with is like even when I was going through university and stuff for for computer engineering they were teaching us we had you know some classes on uh doing some assembly we had some classes on building Um, we didn't build a compiler, but we built uh like we built a like uh I can't remember what the the names of the the tooling is called. Like basically like we worked with grammar of languages and stuff and like is that useful information? It's like it's interesting. I'm sure it was helpful, but could I have literally left out that part of my learning and been okay 100%. And I'm wondering will we see in 5 10 years that there were people that came into software development literally vibecoded their way through the next 5 to 10 years and they're doing great. Like I don't personally want to believe that cuz I think it's a bit of a stretch but I'm trying to keep an open mind because I just I genuinely think that we could see something like that and no one has a crystal ball. So like >> Mhm. So I actually I I have um a lot of opinions around it as well. I think because um of like my background and and even my focus like I've learned this year especially I love products. I love product design and >> um like UX. I I don't mind coding. Sometimes I like coding I think when I'm solving a specific interesting problem but I don't love coding for the sake of it. And that was like really hard for me to get to because it sort of becomes a part of your identity that you have this skill and this ability and um that's your job and career and all of that. But I realized this year it's like I would actually if I could be like a product manager who codes that is my probably my ideal. Um I find the business side very interesting and all of that. But um to your point, I think we're already really seeing that. Like I hang out in a lot of Discords of um all the vibe coding tooling and I'm kind of DMing people randomly and just being like, "What are you working on?" And and how's it going? And these people are really interesting. Like there'll be someone whose background is sales in commercial insurance and he has built a platform and he has users and he has MR because it's like a simple CRUD application that you know it's not like anything special that he's building but he understands the shape that it needs to be for other commercial insurance salespeople and already knows how to sell. So he he just built this basic thing. Um, it looked very vibe cody like the purple gradients and all of that, you know, and uh, but it worked and so and then he was a it worked and like probably the API keys are just like right there, you know, hardcoded. Um, he doesn't care. He's making money. He's he's very happy. And I think there is a lot of that maybe not as like publicized or published but even Peter Levelvels is like a great example where he built a flight simulator and you know didn't have any experience in that. I think he vibe coded the whole thing whole way through and it kind of sparked that like mini wave of AI games. Um, I think the abstraction kind of keeps climbing up higher and higher until it just >> is like a direct interface with our creativity and our ability to express ourselves. But um, yeah, people will be building things and have no idea what is happening under the surface. And it really just comes down to like their ability to talk through it and um, express their ideas. And like another anecdote uh to that is I have a friend who he runs like seven Airbnbs and he really is convinced that he can build a better like um guest management software. Uh zero coding experience and he asked me for help and I was like ah um not really like my thing. Um but I was like why don't you go on lovable and just start seeing the shape of it because that's a good place to start. and he got the shape of it and then he got the dashboard and he got authentication working and he has a database and it and it actually is like now quite complex where it can read incoming emails from Gmail. You can connect your Gmail account. It can parse just the emails from Airbnb, respond with an LLM um and then reply and it it he built it and it actually works and it's like very impressive. So, um, and he doesn't he still doesn't know what he's doing. He just knows how to talk to the machine. And like I don't think he's ever opened cursor. I think he's done the entire thing in lovable, never seen the code. >> Um, and I think like there's going to be more and more of that. And it's it's kind of uncomfortable for people like us who like, you know, went through >> a lot of uh pain and suffering to to be able to do these things. And there'll always be a role if you like know what you're doing. You have a higher bar of like what you can say to the machine. But um >> I I do think like >> if someone else just has a better idea, you're now on like an even playing field. So it's it's crazy times. >> Yeah. I like I think I do think that it's fascinating, right? I think that this is why I was trying to say like I need to keep an open mind because I think you you said it very well. It's like it is uncomfortable to think of a world like that. Um, part of me is like when you're you're kind of talking about some of those things that have been vibe coded and put together, you made the, you know, the joke like, oh, the API keys are probably like, you know, fully exposed. And it's like I wonder genuinely like is are we just getting to the point where we're going to be kind of pointing fingers and laughing at people that have security vulnerabilities like this? And if so, like is the like genuinely is the solution instead of hey man like you have to know the fundamentals and like avoid this kind of stuff up front like you're making stupid mistakes and if you just knew better you would do better like are we going that path or is it like hey like people are going to keep doing this so like let's build things into the AI tooling that that literally go and like attack this kind of stuff and make sure that it's not proliferating in code bases >> and like I feel like were going the second direction because it's very easy for us to sit back passively and just kind of point fingers at people being like, "Oh, clearly vibe coded. Like, I see, you know, your credit card information's like fully exposed." It's like, okay, like, how do we build the guard rails into the the AI tooling to prevent things like this? Now, is it always going to be bulletproof? Like, no. But, I mean, like, humans screw this stuff up, too. So, um I don't know. I I feel like there is uh there is a future where this stuff becomes more rock solid, that we have more people able to build things. It's just uncomfortable to think that um you know that might be the case. And I think that some people hear that and they get concerned that like well does that mean that my job isn't relevant anymore? Like am I going to be obsolete? And I'm like, I don't I'm well, maybe before I even answer that, what are your thoughts for people that are like more they seem concerned because they feel like they're going to be obsolete because of AI and how it's being used? >> Yeah, that's a really good question and that was like a big theme that I had for myself this year. Uh when I started the year, I was like, I need to learn a trade because that's sort of where I started. And I'm like, "Oh my god." Like, it's sort of easy to see the trend line and say, "Okay, today it can make components, tomorrow it can, you know, refactor files. The next day it can refactor an entire codebase." Um, and it can and like I do 90% of my coding now through chat, like through chatting with cursor. And I have cursor open and I'm like add a scratch card feature to the app here. And then it'll do some thing with you know React Native Skia and you know gesture handler and pan responder and I won't even before I would look at the code and now I'm just like I just try it and um if it works I'm like good job if not I'm like no mistakes you know 10k 10k mr no mistakes please. Um, and and I'll do that like maybe two or three more times and if it's still not working, I'll like be like gh. And then go and look at the code and and try and fix it. And it's usually something simple and I can fix it pretty quickly. But it is still quicker for me to just do that like texting part. And I think that as an anecdote to to just be like like there's so at the at the top level there's lots of problems. there's still, you know, hundreds of thousands of millions of problems to be solved and to be solved with software. And I'm trying to think of it from that perspective like are all software problems solved? No. So that means there's still like value to be acred and and earned by solving these problems for engineers. And the best engineers can solve the hardest problems always. So that's kind of like evergreen. So they will always be compensated highly for that. um as the problems get simpler and simpler there are there's like less value to be earned for that um and then some of the problems are like interesting because like cal calorie trackers and cali is a great example um you know Blake Anderson did not know how to code he vibe coded calai into like the top charting calorie tracking app and and a good calorie tracking app it's at First it was like kind of a gimmick like take a picture of your food, this is how many calories, but it's actually a very high quality app. Um, great on boarding. I've like studied it a lot for my own apps. And um, the the idea that like, you know, My Fitness Pal or um, Lose It or any of these have like solved people's calorie tracking needs is not true. like this new upstart came, did a slightly better job with a slightly better angle and um you know earned a ton of money from it. So I think as you as you get down from like the hardest problems to problems like that where there are there's room for a lot of solutions and then there's also room for um like taste and you know people want to do it in different ways um there's ways to like earn value from that. So that's my answer in in that sense. I think in terms of like big companies and how that works, I really have no idea. Like I think companies in general, it's like a whole other topic. Like I worked at a relatively large bureaucratic organization where and I saw it was a startup when we started. it was like 50 people and then it was like 300 people and um which is still like small but it was within a bigger thing and you just see >> how decisions get abstracted away and and all of that and work becomes very weird where it's like you know you get a ticket and just the management of this ticket is like half the work week and the actual work is like so I don't really know what's going to happen at companies I would hope that they get more streamlined but I don't like that's a human problem and Maybe that's a human problem that gets solved by someone building billiond dollarar software. >> Yeah, that's a that's an interesting kind of segue. The um that kind of growth trajectory at a company I we didn't chat about this beforehand, but before I worked at Microsoft, I worked at a startup, I was employee like seven or eight and by the time I left it was like 250 people. So yeah, not a not a huge company by the end, but like what you're describing, like very familiar with that going from like it feels like, you know, there's, you know, work that has to be done. So people are just doing the work and as the company's growing, there's more there's more red tape around things. There's more process. There's more, yeah, bureaucracy. And it just kind of happens because there are more people. I don't think it's ever the intention where people are like, you know, let's just add more layers of complexity for no no good reason. like there's, you know, usually motivation for it. I see it exaggerated at Microsoft, but just to like to give you an example, it's like there's stuff that's like compliancy concerns or security concerns. And like at Microsoft, if I had someone on my team who spun up a new service or something and there was a compliance or security issue, like that's not like a oops, like you know, the the no users we have are going to interact with that. like that could be like a a big security breach where you know there could potentially be many users impacted. So like we have to have those levels of like red tape and things like that. So um it it's kind of like a I feel like it's a it's a natural thing to happen. I don't I don't love that kind of thing and I'm not saying there's no way to make it more lean, but you know I think we do see some of that stuff kind of creep up more naturally. But um I guess there there's there's so much to say about that stuff because there is what you say of like there is good reason for it sometimes but um I've also seen like it can be the case of like territory and politics and >> you know just like weird decision-m and I just I found that so fascinating because it it's like the the curse of success is that you have to have more people to manage a bigger thing but then the thing itself like does start to degrade in various ways >> 100%. Yeah. And like the when you get into situations where there's like politics, where there's like territory is such a good word for it. Um it starts to get kind of bizarre and I feel like there's the incentives are misaligned. So I feel like it's smaller companies. Uh it at least to me it it felt like it was easier to kind of have everyone rally behind this is the mission of the company. You might have uh sub teams and stuff. It's not like you know a 250 person engineering team or something. But you know obviously even if the engineering team is like a smaller part of the company say it's out of a 250 person company it's say it's a 100 people just to make up a number >> like you're not having a 100 person single engineering team there's sub teams working on different products or feature sets whatever. >> Um but even with that like people are very much aligned to the business. it seemed like people it was easy to do that when you have like different business units uh and like you have people that I find find it big tech everyone's like extremely focused on like their career path which I don't think is >> wrong I think it's good to be like how do I progress in my career but when the incentives for your career progression do not seem to be aligned with like the mission of the company I think you're going to have people that are very much focused on themselves >> like you're kind of incentivizing that. So >> yeah, it's a really interesting thing. I found it to be like by the end I was still like an IC. I was contributing on you know very like specific features but I because I had seen it all kind of um like every aspect of it. I got really fascinated with how things slowed down in various ways like and and that sort of became a bigger interest of mine at the company and I I I had a chance to be a TPM for a bit actually and kind of run our team's like board and like interface with other teams and um I I really wanted that experience just to see what that is like to like have to deal with dependencies basically and and manage people's expectations and it's like we want to release on this date, but we have this feature that has to go into the app. So, like you have to wait for us, but we can't wait. Like we have this marketing thing and the marketing team is now and yeah, I found that very very interesting. I don't know if I would want to make a career out of it, but I I see that there's something there because I think like orchestration is probably one of those problems where you can really create miracles from like really high quality orchestration and uh companies like like Tesla or SpaceX are are good examples to me of like very I think SpaceX more so where it's like if everyone is like super aligned on this thing that is like kind of 90% failure and you you have it in these like tanches of like we are going to work towards this thing and it's either success or rapid failure. Most people if it's like rapid failure they would leave or blame each other or whatever but it's like if you can maintain coher and then every one of these parts has to like fit together perfectly. >> Um I think maintaining coherence in a company is one of those things I've become very interested in. Yeah, it's uh it is truly fascinating. Um, yeah, I'm curious and one of your your notes that you had sent over was like for big companies and moving faster, do do you envision that AI can or is already playing a role in that or uh when in from your note is this more like an open curiosity where you're like I wonder if this is a kind of solution. I'm curious your thoughts on that. Um I think I think it's like right now it's still open but I think it has to be like it eventually has to be because what we can do you know if if you can monitor the entire Slack conversation ecosystem of an organization of you know arbitrary size any size and an AI can look at every single conversation and every single like pull request and every single ticket all at once um and we're not like far from it being able to do that with you know much much higher clarity. It should be able to like draw kind of uh I don't know what the right word is but like draw the relationships or the conclusions that make the most sense for like insights to like actually you know it's that joke of like oh we extract business insights and >> what do you do here? >> Yeah. Like if you had something that could actually do that and be like looking at all your tickets in a sprint and say like actually these three don't need to be done this week. And um you know it doesn't I don't know if it solves a problem because then you maybe have someone who's like oh but those tickets like mean something for my career so I'm going to override the AI and push them through. Um but it's I do feel like the tools are actually there. I think one place where it's used really really well right now is like customer review uh summarization and like contextual extraction >> and that's the same thing as like a company like a company's internal coms are basically like kind of customer review for that business. So, I feel like there's some level there that we're not quite reaching where these things can be extracted and like higher value can be um you know drawn out from these from these bigger complex orgs. But I just you I think the person who's going to do that or the team that's going to do that like needs to have really good insight into how these orgs work with like a lot of experience working with them. Uh, so it's like a problem I find interesting, but like I would not be able to solve it because I I don't think I'm built to like work at Microsoft for for 10 years. It would not work for me. >> But that's I think a really interesting point, right? I think a lot of us, especially as developers, the the focus is the LLMs are working the other direction for us. We're telling it stuff and we're saying go go write code, go make things. And what you were just describing is actually the other direction, which is here's a lot of data, like draw insights from it. And I I guess I'm curious like the I I do think that AI has been very effective at that kind of thing. I think there's still lots of room for improvement. But if you think about it, like it's like almost like standard features now we have in like Slack, Teams, and whatever. It's like the your meetings recorded. You get automatic like summary transcription kind of stuff going on. like that that's super effective to be able to go back and you know I think I work at Microsoft so I use Teams but like having you know different parts in the recording where it's like who's talking you can jump to things and like it's just like that that kind of insight from a conversation so powerful. I I do think what's very sort of interesting as a next level is like I don't know if we have the right signals or if we do if we're properly feeding them into like AI tools yet to be able to like to get the insights from that. So >> it's like if the AI is very good at summarizing things are we even giving it the right sets of information to work with? I don't I don't know if that's something that's been solved necessarily. Um, an example is like at least I don't know if I can't speak for all of Microsoft because it's like a a billion people, but um, at least in our org, we do something that's called like a signals survey and we do this a couple of times per year and it's like a handful of questions. It's a pretty light survey and it's to try and gauge like I mean the words kind of there. It's like to gauge your engagement and like how how much you're enjoying work, if you're aligning with work, if like if things are kind of moving in the right direction for you and like therefore your organization is like a good place to work. And so we have a survey like this a couple of times per year, but like the questions are always evolving and they are just like multiplechoice survey questions. Like I don't know, I'm not trying to to say it's like a bad tool. I actually get a lot of value from that. But is that is that the best kind of thing that we could do to get data like a couple of times per year a handful of multiple choice survey questions versus like >> could we and people might get spooked by this so just fair warning. Um you know is there more more that we could be doing on a regular basis? Like could something be watching team chats and being like that you know the the tone in this chat seems to be like it's positive and like no you know what we hit I'm just making this up we hit April of this year and since April to you know uh October like the tone has been very negative and whatever like maybe there's indicators like this where we can be doing it more regular we have more signal and we can just draw more conclusions from that. I I wonder if we can uh start to see more stuff like that, but I think people get scared. >> I I find that Yeah. And that's such a great example. That's such a great example because there's so many elements there to like unpack where it's like on the one hand um people are like they don't listen to us enough and then you're like okay give us feedback weekly and they're like oh this is too burdensome. >> So it's like kind of people are never really happy with like there is no happy medium. It's also you have such a large amount of people at that point to need this tool that you're going to have distribution of like how people feel about it and you are not going to make everyone happy. You kind of want to aim for you know 60 to 75% of people enjoy it. um we had similar tools compliance um I don't know if compliance is the right word but like the the usage of them was very low >> and every quarter or whatever we'd have like a or maybe it was like once a month it was like this meeting an all hands like hey like you guys aren't filling out this form you know how can we get you to fill out this form and everyone's like >> get rid of the form >> form yeah I hate the form but also listen to me more um and then so then it's like okay what if you had like a clippy who was just your personal concierge at work who you could just always talk to. He's always there. Um he's not going to bug you too much, but sometimes he'll be like, "Hey, like I really need some insight from you." And he's like friendly and great, but you also know that he is like HR behind him. He's like this monster that you you don't act he's not actually your friend and you don't trust him and uh you probably don't even respect him because you you know he's just like and and that's the thing. It's like is he just he he is by definition just trying to extract the most amount of value from you and he's like I only want you happy because then you'll do your best work. Like if I if there's a research study tomorrow that people do their best work when they're miserable like I will make you miserable and and then you'll so it's like so it's like and then there's the whole like surveillance thing like people don't like to feel like they're being watched. They want to feel like they're being trusted. And so it's it's hard. And maybe whatever we have right now is that just doesn't have the right um shape to like actually help in in this way. But I think the thing that would help is coming. And there's there's lots of like like we live in the age of miracles now. It really is. And there's lots of new ideas that we are kind of on the stepping stones of that we could maybe reach. But even things like a personal agent and there is still Clippy maybe, but you have your own agent. And so instead of you talking to Clippy all day, your agent, which does not belong to the company, you bought it from a separate service who manages personal work agents and that agent advocates for you every day. And so you're working, you're doing your thing, you're having your meetings, your transcripts, whatever. And then your agent is like, "Hey, Clippy, like we're doing great. Everything's looking good. Um, you know, because look at what we said here. look at this work and it's basically like your daily advocate and then Clippy's like are you sure like and and they they sort of can like go back and forth stuff like that I feel like is pretty sci-fi right now but I think we could start to see versions of that where the it's sort of like an allowable interface for how we can do better as bigger bigger teams but like in a way that works for everybody. Yeah, it's a it's definitely an interesting challenge, right? Um the I I think people just there's concerns about how much effort goes into stuff. There's concerns about privacy there and and I'm not saying these are like invalid concerns. Like everyone is absolutely entitled to all of these different opinions. So, um yeah, it's hard to do at scale. Like if you were to talk to me and maybe a couple of other people, like there's some stuff like if it's at work, I'm like I don't I assume I don't have privacy. So like if you want to monitor my personal chats like okay like I'm talking at work like that's fine. I also worked at a digital forensics company for eight years and like I'm I'm like I just kind of I have a different view of like data and and sort of privacy associated with data because of that. And I acknowledge that's not the same opinion that everyone else has. But for me I might be totally fine doing that kind of stuff. what I don't want is something bothering me all the time because I would be like, "Don't distract me. Like, leave me alone." Um, so >> that's sort of the difference. Yeah. It's like cuz obviously like you're on a work computer anyway at work and like all of that is obviously their their property, but it's it's sort of the difference is it's like it feels like there's somebody in the room just standing there like watching over you. And that's that's the difference. It's not like it's passive data being put out. It's reactive. And yeah. >> Well, how was that data going to be used? Right? Because it's one thing to say that they can access it, but sometimes uh when you use the analogy of like someone else being in the room, that makes it feel like someone is waiting for you to do something so they can go ah like got you. >> Yeah. >> And that's like% not supposed to be the intention for what we were just talking through. It's like can we get insights to figure out how to make people happy so that they can work better. Not we're waiting for you to slip up so that we can go do something. But then the problem is like I mean if you have technology that can do one like why would you not have technology that can do the other? It's a it's a slippery slope and I think that makes people concerned which is fair. I think it'll just come down to values and like where you work and different companies will do different things and I love I love the free market for that. like there'll be different approaches and I think if you are lucky enough to find a company that like values your you know um independence and ability to just like work on your own versus a place that feels like it needs to like kind of watch you through the camera and like have like a heart rate monitor on you to see you know like tracking your your eyes. Um there's there's different places and so hopefully there is enough of the former that it is like still you know there's there's a lot of people that get to work at places like that. I know there's like there will be tons of the latter there today are tons of companies that make it really kind of ownorous on their employees. So >> um yeah that that and that's maybe what like abundance and you know the future look like is is not that there's no bad. I think that's kind of impossible, but that is that there is like a lot more good and I think we we're getting like a lot more entrepreneurship and solo um builders because of like AI tooling. So maybe more people can build their own things and work for themselves and kind of earn money without having to join something that isn't aligned with how they want to live. >> Right. And I think you used a great word and I think that's a a good um focus for my thoughts for kind of wrapping up is like abundance, right? I think a lot of people see AI as something that's quite the opposite of abundance. They're like it's the end. There's no more software development. Like, you know, it's very much like confining and restricting and closing off. But I I personally think abundance is is a great word. It's literally the opposite of what I was just describing. And it's like there's more opportunities. You said earlier in this conversation like there's always problems to solve. Like >> yeah, we we're not gonna turn the AI on and we're like, I guess we ran out of problems to solve. Like there's problems always. So um and that means abundance, right? We have tooling that can help us get through this stuff faster, more opportunity for more people that never had that before. So um I think abundance is a great word for that. But um Simon, I wanted to say thank you so much. I want to make sure that if folks want to reach out to you, what's the best way they can get in touch with you? What are you working on? Tell us. >> Uh yeah, thank you. Yeah, this was a really really fun conversation. So um my website is simon.ca if you want to like see some of the stuff I've worked on. Uh I'm currently building a mobile app called Cut Log which can measure your body fat from just a couple of pictures um using like machine models and uh so looking for beta testers for that if people are interested and uh you can find me on Twitter at Siame Stern Sim Stern yeah at Twitter. >> Awesome. Yeah, thank you so much. Yeah, this is super cool. Well, I think there's a lot of insights for for people that were listening through and uh yeah, I think uh I think there's an abundant future ahead of us. So, thank you for using that word because I think that's going to stick with me for a little while. >> Thank you. Appreciate the chat.