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

Speaker A: In this video interview, I sit down with Simon Stern, who started off as a self taught developer, moved into being a bootcamp 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 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.

Speaker B: Yeah, for sure. Thank you. Uh, thanks for having me, first of all. Really appreciate it. Um, so my career journey is relatively side windy. Um, I graduated with a degree in biochem. And originally my plan was to be a doctor, go into medicine. And I spent two years working as a research, um, assistant and scientist, uh, after graduating. And I found out like, I hated every part of that life, part of that job. I, uh, 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 life, don't go into medicine. Uh, 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? Because I really.

Speaker A: They came together and this was the event for, for you to kind of.

Speaker B: 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.

Speaker A: And because that's not, that's not a small thing, right? That's like you, uh, up to this point you're like, is what I'm doing? And now all of a sudden it's like, no, it's not. But what is what?

Speaker B: Like all of university for 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 two weeks later I was in Australia and with no job, I 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 bricklayer, a truck driver, uh, a cleaner, a driver. Um, I cleaned up a racetrack for a big race. Uh, uh, I've 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. Cause 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 ah, 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 m value having like some sort of skill, something that actually is a tangible 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, uh, esoteric knowledge that is only useful in very, very like niche verticals that are not well paying. So Interesting.

Speaker A: Okay.

Speaker B: 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 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 this 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 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 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 just asking 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's kind of perfect. They had lots of different projects. And after the first day there and they were cool, they're 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 three months straight, nine to five. 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 six months, like a proper full, like, junior dev role, and the rest has kind of been history, I eventually started my own agency. Um, and then I got a really cool job that I did for the last five years, uh, for a big pharma company in the States, and really, really enjoyed that react native role. That sort of became my. My breadbasket 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. 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 three months at network school, which, if you know what that is, it's like, biology.

Speaker A: No, no.

Speaker B: So the former CTO of Coinbase, Balaji Srivanasan, is like this big crypto, um, personality 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 it's met founders from all over the world and kind of we all, like, pitched together and like, worked on ideas together.

Speaker A: Wow, that's really cool.

Speaker B: Yeah, that was like, by far the coolest thing I'd ever done. I got to, like, meet, um, biology 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.

Speaker A: 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, uh. 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 adult. 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,

Speaker B: 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 can make stuff, you know, I've learned how to build things and I like to build kind of. 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.

Speaker A: That's very cool though. That's awesome. I have a, ah, couple of questions about your career journey that I think would be helpful, uh, 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 going to go learn this. That I'm going to spend time doing that, like, for some people. And I feel like 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 gotta 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?

Speaker B: 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 because 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, uh. 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 bootcamp instructor. And I kind of have a lot of opinions about boot camps, but this was like, pre bootcamp, and it was very project based because 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 the list of tweets? You know, I want to click on one of those items in the list. 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 9pm at night, and then know what you have to do the next day. Um, but I did feel a very strong sense of like, I can see the finish line.

Speaker A: Right.

Speaker B: And that, 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, a different kind of thing. Yeah.

Speaker A: 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 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 do it. Um, 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, ah, kind of normal. And I think that maybe as. As humans, like, we're very Much like what, what is the shortcut?

Speaker B: Right?

Speaker A: 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.

Speaker B: Yeah, yeah. 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 three months and then you get a tech job. And um, I worked at a bootcamp for a year and then I worked at the U of T boot camp, which was unfortunately uh, like just worse. And I think there is definitely the 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, three months and then, um, 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 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 whole kind of industry suffered from it. I think there was too many people now at a skill level that was at the tutorial stage, as you said, which I don't believe in tutorials too much. I think they're a good way to learn the API or 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 teach you.

Speaker A: 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 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 step by 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 set. That is great. But to tell people do this for three months, you will get a six figure job. I'm like, you can't guarantee anyone that unless you're the one hiring them after for six figures. Then, yeah, 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.

Speaker B: Yeah, and I do think, I, uh, mean, there's a lot to be said about accelerating your learning. And a lot of really successful colleagues 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. Uh, I think because 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 impressive, uh, things and, and aesthetic things because they have that outside, like, idea for it.

Speaker A: Yeah, they bring different perspective into what they're, they're building in code and yeah, 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 m purely focused on, on writing code. So I think, um, 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 five years old and like, things are going pretty good. Like it's okay to have a different journey.

Speaker B: Yeah, no, I totally agree. And it's interesting nowadays too because everything has kind of been flipped on its head with, uh, Vibe coding. Uh, I'm m curious what your thoughts are on that as someone who likes, makes this kind of content with career journeys tutorials. Like, how has that affected your perception?

Speaker A: Yeah, it's uh, I think it's interesting. I have a handful of different perspectives and I think the challenge right now is like, given that it's early, um, 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, if I don't have it backed by like data, then I'm like, I must keep an open mind. So to give you an example, uh, with like Vibe coding, 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 preview of what I'm going to do. And 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 were in C. We have uh, the Roslyn compiler and we can build analyzers that do 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. 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 code base. So, like, I should now, like, go spend time, like, learning about them. They're operating, but that's fine. But 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, uh, 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 M. We didn't build a compiler, but we built, uh, like, we built a, like, uh. I can't remember what 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 five, 10 years that there were people that came into software development, literally vibe coded their way through the next five to 10 years, and they're doing great? Like, I don't personally want to believe that because 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.

Speaker B: So I actually, I have um, a lot of opinions around it as well, I think, because, um, of like my background 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 the 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 uh, I'm kind of DMing people randomly and just being like, what are you working on 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 MRR 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 just built this basic thing. Um, it looked very Vibe Cody, like the purple gradients and all of that. And uh, but it worked. And so, and then he was. It worked. And like, probably the API keys are just like right there, you know, hard coded. Um, he doesn't care. He's making money, he's very happy. And I think there is a lot of that. Maybe not as like publicized or published, but even Peter Levels 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, 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 he built it and it actually works. And it's like, very impressive. Um, and he still doesn't know what he's doing. He just knows how to talk to the machine. And 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 there's going to be more and more of that. And it's kind of uncomfortable for people like us, who went through a lot of pain, uh, and suffering to be able to do these things. And there'll always be a role if you know what you're doing. You have a higher bar of what you can say to the machine. But, um, I do think if someone else just has a better idea, you're now on an even playing field. So it's crazy times.

Speaker A: Yeah, I do think that it's fascinating. I think this is why I was trying to say 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 kind of talking about some of those things that have been vibe coded and put together, you made the, you know, the joke. Like, all the API keys are probably like, you know, fully exposed. And it's like, I wonder genuinely, like, ah, 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. Uh, 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 we're 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 guardrails 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 feel like there is, ah, 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? 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?

Speaker B: 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. 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 code base. 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 something 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, 10k mrr. No mistakes please. And I'll do that maybe two or three more times and if it's still not working, I'll be like, ugh, uh, and then go and look at the code 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 is an anecdote to just be like, there's so at the top level there's lots of problems. There's still 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 problem solved? No. So that means there's still value to be accrued 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'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 Cal AI is a great example. Um, you know, Blake Anderson did not know how to code. He Vibe coded Cal AI 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 onboarding. I've studied it a lot for my own apps and um, the idea that MyFitnessPal or um, lose it or any of these have solved people's calorie tracking needs is not true. This new upstart came, did a slightly better job with a slightly better angle and um, earned a ton of money from it. I think as you get down from the hardest problems to problems like that, where there's room for a lot of solutions and then there's also room for um, taste and people want to do it in different ways. Um, there's ways to earn value from that. So that's my answer in that sense. I think in terms of big companies and how that works, I really have no idea. I think companies in general, it's like a whole other topic. Like I worked at a relatively large bureaucratic organization where and uh, 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 all of that and work becomes very weird where it's like, you know, you get tickets 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 billion dollar software.

Speaker A: 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 7 or 8 and by the time I left it was like 250 people. So yeah, not a, not a huge company by the end but like uh, 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 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 uh, 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 uh, oops, like you know, the, the no users we have are going to interact with that. Like that could be like 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'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's, there's there's

Speaker B: 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 making. 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.

Speaker A: 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 um, 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 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 100 people just to make up a number. Like you're not having a hundred person single engineering team. There are 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 at 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 gonna have people that are very much focused on themselves. Like you're kind of incentivizing that.

Speaker B: 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 had a chance to be a TPM for a bit actually and kind of run our teams like board and like interface with other teams. And um, I really wanted that experience just to see what that is like to like have to deal with dependencies basically 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. 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 see that there's something there because I think like orchestration is probably one of those problems where you can really create miracles from really high quality orchestration. And uh, companies like Tesla or SpaceX are good examples to me of very, I think SpaceX more so where it's like if everyone is super aligned on this thing that is kind of 90% failure and you have it in these tranches of 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 coherent 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.

Speaker A: Yeah, uh, it is truly fascinating. Um, yeah, I'm curious and one of your notes that you had sent over was like for big companies and moving faster, do you envision that AI can or is already playing a role in that or uh, wouldn't 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.

Speaker B: Um, 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 if, if you can monitor the entire slack conversation ecosystem of an organization of arbitrary size, any size, and an AI can look at every single conversation and every single pull request and every single ticket all at once. Um, and we're not far from it being able to do that with much, much higher clarity. It should be able to draw kind of uh, I don't know what the right where it is but like draw the relationships or the conclusions that make uh, the most sense for like insights to like actually, you know, it's that joke of like, oh, we extract business insights and

Speaker A: what do you do here?

Speaker B: 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 comms 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, 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.

Speaker A: But that's, uh, 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 a handful of questions. It's a pretty light survey and it's to try and gauge like, I mean uh, the words kind of there. It's like to gauge your engagement and like how, how much you're enjoying work, if you're aligned 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 multiple choice survey questions. Like I don't know, I'm not trying to say it's like a bad tool. I actually get a lot of value from that. But 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 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 start uh, to see more stuff like that. But I think people get scared.

Speaker B: I, I find it. 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 and 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. 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 know, he's just like. And. And that's the thing. It's like, is he just.

Speaker A: He.

Speaker B: 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 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, uh, 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, we're doing great. Everything's looking good. Um, 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? And they sort of can 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 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.

Speaker A: Yeah, it's, uh, a. It's definitely an interesting challenge. Right? The. I. I think people just, uh. 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.

Speaker B: Um, so that's sort of the difference. Yeah, it's like. Because 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.

Speaker A: Yeah.

Speaker B: And that's, that's the difference. It's not like it's passive data being put out. It's reactive and.

Speaker A: Yeah, well, how is 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.

Speaker B: Yeah.

Speaker A: 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 way? It's a, it's a slippery slope. And I think that makes people concerned, which is fair.

Speaker B: 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, independence, uh, 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 a ladder there today are tons of companies that make it really kind of onerous on their employees. So. Right. Um, yeah, that. And that's maybe what like, abundance and, you know, the future look like 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'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.

Speaker A: Right. And I think, um, you used a great word, and I think that's a good focus, um, 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, uh, 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 going to 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 I, um, think abundance is a great word for that. But, 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.

Speaker B: Uh, yeah. Thank you. Yeah, this was a really, really fun conversation. So, um, my website is simonstern Ca if you want to, like, see some of the stuff I've worked on. I'm currently building a mobile app called Cut Log, which can measure your body fat from just a couple of pictures, um, using m, like machine models and so looking for beta testers for that if people are interested. And you, uh, can find me on Twitter @simystern s I m I stern. Yeah. At Twitter.

Speaker A: Awesome. Yeah, thank you so much. Yeah, this is super cool. I think there's a lot of insights for people that we're listening through. And, uh, yeah, 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.

Speaker B: Thank you. Appreciate the chat.