Software Huddle - Navigating the Transition from Big Tech to Startups with Ben Popper from Stack Overflow

Episode Date: September 12, 2023

Startups can be a ton of fun. Also, it is sometimes very stressful and ultimately a very different experience than working at a company like Google, Meta Apple and so on. Benjamin Popper is the Senior Director of Content at Stack Overflow and is our guest on the show today. The background on today's episode is that both Ben and Sean have worked for startups as well as in Big Tech, and they have lots of friends and former colleagues who have struggled with navigating and thinking through the transition from big tech to startups, particularly for engineering roles. In today's show, we walk through the choices faced while making such a transition. We focus on what are the options you have and how can you align these options with the ultimate goal of becoming the best software engineer you could be. Follow Ben: https://twitter.com/benpopper Follow Sean: https://twitter.com/seanfalconer Software Huddle ⤵︎ X: https://twitter.com/SoftwareHuddle LinkedIn: https://www.linkedin.com/company/softwarehuddle/ Substack: https://softwarehuddle.substack.com/

And one of the things that I think is super commendable about Stack Overflow is the level of transparency employees have, you know, into the business and its goals and its targets and its results. I do think one nice thing, if you're able to educate yourself in the world of computer science and software development, is you can always say, well, you know, I might lose this job, but, you know, there's always more demand than supply when it comes to talented engineers. And so, you know, I'll find my way to something next. You know, I think that that is a really interesting strategy to approach for a company to embrace open source and to encourage their, you know, developers or engineers to work in that so that they can, in that way, reach a really broad community of folks who might be interested in working at that company and show their technical acumen.

Hey, everyone, this is Sean Falk here, and I'm super excited about this episode with Ben Popper from Stack Overflow. The background on today's episode is that both Ben and I have worked for startups as well as in big tech. And we have lots of friends and former colleagues that have struggled with navigating and thinking through the transition from big tech to startups in particular or engineering roles. Startups can be a ton of fun. Also, sometimes they're stressful. And it's ultimately a very different experience in a lot of ways than working at a company like Google or Meta or Apple and so on. And if you don't know anything about startups, it can be difficult to evaluate a company at an early stage. It's difficult to evaluate maybe the offer that

they're making if you don't know anything about options and what that all may mean for your career. So Ben and I share our thoughts, experience on these and more. Hopefully you enjoy the show. Please remember to subscribe and hit me up on email or Twitter if you have any questions or suggestions for the show. All right, now let's get to the interview. Ben, welcome to the show. Hey, Sean. Long time no see. I think you and I might have been recording a podcast earlier on my side of the house, so it's great to talk twice in one day. Yeah, awesome. Yeah, it brightens my Friday, to say the least.

Yeah, so thanks so much for being here. So I want to talk about startups and engineering, but maybe before we dive too deep into the weeds here, you can introduce yourself. So who are to talk about, you know, startups and engineering, but maybe before we dive too deep into the weeds here, you can introduce yourself. So who are you? What do you do and how did you get to where you are? Yeah, sure. So I'm Ben Popper. And at the moment, I'm the senior director of content at Stack Overflow, where I've been for five years. And so at Stack Overflow, you know, my job is working on the blog and the podcast and the newsletter, making sure it's full of stuff that's interesting to a wide range of like developers and technologists.

I came from a journalist background, so I did maybe 10 years covering startups and tech companies. I worked at The Verge for five of those years. And when I was working at The Verge, I became the drone beat reporter. We all had to pick like a gadget. I picked consumer drones and they kind of blew up between 2013 and 2020. They went from something that was like relatively obscure to something a lot of people knew about. And so around the middle, I think of 2018, I decided to make a change and move from journalism to working inside a tech company. So I joined DJI, which is the world's biggest manufacturer of consumer drones. I spent a lot of time in Shenzhen and China,

traveling back and forth. I got to do like product launches and videos with them about the way people are using drones around the world. And then ironically, I said, you know what I really miss is having a great office and culture with people because that wasn't something DJI really had. And so I found this job at Stack Overflow, which had an amazing office in New York City.

We used to have lunch together every day. It was sit with the engineers, sit with the salespeople. Sadly, the pandemic changed all that. I now live about two and a half hours outside New York City. But that's how I found myself at Stack. And kind of, yeah, I've been sitting at the intersection for a long time of, you know, business and technology and more recently diving more fully into like software development as my focus. That's one of the reasons I was really interested in having this conversation with you, because I think that you have sort of like a unique perspective as somebody who's been like, worked as a tech journalist.

You've seen a lot of companies. You've probably talked to lots of different people and kind of taking almost like an investigative approach to it. So you're a little bit outside of it, but not completely divorced from it. So you probably have a good sense for what makes for a successful company to some degree. And of course, with your experience at Stack Overflow, I'm sure over the past five years,

you've seen tremendous amount of like growth and change that's happened there as well. Oh yeah, for sure. Yeah, I mean, you know, I think we're coming to the beginning of a new era for startups. It was hard for me to realize it

when I came fresh out of, you know, school in 2010 to start covering stuff that we were living in this, you know, Zerp economy of zero interest rates. I didn't understand then that the way startups were getting money and the way they were getting valuations and the way big tech companies were able to, you know, borrow and acquire was, you know, wasn't normal. Wasn't, you know, to me, it was like, this is my introduction

to technology and business. I'm writing about it. I'm learning it. I didn't have that perspective that, you know, things aren't always this way. And so the pandemic in some ways even maybe amplified those trends, you know, made some of those excesses go even higher. And then more recently, you know, I think things have, the pendulum has finally swung the other way where, you know, companies from big and small are increasingly focused on the bottom line on profitability. And that has led to a lot of pain in the tech industry. A lot of layoffs at big companies, a lot of down rounds at startups, and a lot of uncertainty about whether or not, you know, this new normal is going to last.

Yeah, and I think because of the big change, and we've even seen like major, you know, layoffs from major companies, like companies like Google that is known, like, basically, they never never lay people off like you you don't get fired from google yeah yeah and it's really i think changed the the industry and it's changed i think the um you know an engineering perspective on you know where am i safe or what kind of job do i want and a lot of people are moving from you know maybe the comfort of big tech or a career in big tech and And now they're faced with like, do I go to a startup? So that's kind of, I think the, what, what I was interested in and trying to explore, because I think there's a lot of people that are in that space. I, even my, you know, former manager at Google, he's in that spot today. You know, he's, he spent over a decade at Google. And then now he's thinking like, you know, do I start my own company or what does that mean? And do I, or do I go join a startup and what does that mean? So in my own experience, you know, I've been a founder. So I've seen like the really early stages of a company. And I've also, as I mentioned, work for Google. So, and now I work for a series B startup. So I've seen quite a few different stages personally for a company and an engineering organization. And there's definitely big differences between those experiences. And from your sort of years of

working in the space, like how is, in your opinion, like engineering or working at a startup kind of different than working at like a big tech company? Yeah. So, you know, I've worked at three companies that I guess, you know, when I was there, you could have technically still describe them as startups in that like they hadn't gone public and they'd raise some venture capital. Right. So I started working at Vox Media and, you know, it was in growth phase at a point in time when I got there, they raised money and declared themselves a unicorn, which was the, you know, that was the fashionable thing to do. You had to be on the unicorn list to hire the best talent. And I think, you know, one of the things that's nice about working at a place early on, I joined The Verge, you know, six months, I think, after it's founded. So not founding team, but pretty early on, is that, you know, there's a lot of greenfield. Not every department has been created. You know, there's not maybe, you know, the same level of middle management or hierarchy that you find at a big company. And so, you know, if you're ambitious or, you know, if you have an idea, it's easier to get that in play to see it tested. And if it works, you know, I think to profit from that, maybe not profit directly in a monetary sense, but, you know, expand the scope of what you're working on, get a promotion, you know, become a manager, or take on new initiatives, you know, become the leader of a new initiative.

That's certainly one thing that maybe engineers, you know, who are eager to sort of grow beyond just, you know, what they do as an IC might benefit from at a startup, right? You might go somewhere, it's very early, four or five people, they don't have a chief security officer, but then they start signing up enterprise clients and they sure are going to need one. And so if you're the person who steps forward and raises your hand, that might be an opportunity for you to grow into some big shoes. podcast, Partially Redacted, where you hear about a lot of the engineers that sort of find their way into privacy. And a lot of times it is that experience. It's like, well, I was working for a company. We were starting to deal with like highly sensitive data, regulated data, and we had nobody to own this. And I was like, you know, kind of raised my hand and got interested in it and found out that I really love it. And then they essentially crafted that career in privacy. That's a harder switch, I think, to do in big tech and it i think you know there's of course value in in both types of experiences but they are

very different like uh you know from my experience at google and also working with a lot of young engineers that have moved from college into those those careers like one of the big things is you from an infrastructure standpoint like those those problems are solved like you're basically turning knobs that someone like already figured out a decade ago like oh i need this much scale okay let's let's tweak this parameter and it's you know there you go and your focus is generally more narrow as well because you just have more resources more people people and they've kind of like figured out a lot of this stuff. So you can be really have really specific, essentially, job role, and there's less sort of ambiguity with what you're doing. And I think you also have a better support system. Like they're used to nurturing talent. You know, they could take somebody who's, you know, 22 years old, straight from their computer science undergrad and invest a couple of years in turning that person into a great engineer. It's harder to do that at a startup

when you're under the pressure of getting product market fit, figuring out your go-to-market, generating revenue, raising that next round. It's hard to say, I'm going to put two years of investment into this person and turn them into a great engineer. But at the same time, there's this trade-off of, like, as you mentioned, less growth opportunity. Like, you can't, it's harder to step outside your swim lane and say, I'm going to take on this new problem or new challenge. And because essentially there's no one else to do that or it looks interesting to me and I'm excited about it. I like the way you frame it. I think, you know, there are opportunities to learn it both, but maybe they're a little bit different. At the startup, it's often way more self-directed or, you know, it's in the interaction with your team

trying to solve, like you said, big problems of we don't really have infrastructure, you know, if this thing takes off and gets a million downloads or, you know, we've never dealt with enterprise level security questions from a customer before. So you're learning, you know, sort of with your peers, maybe less a mentor, and I'm sure it could happen. Whereas at a large organization, some of them almost have a curriculum when you come in, you know, you're not going to touch any production code for the first six or 10 months. You know, there's a track here, essentially, that's going to get you up to speed on what it would be like to be an engineer who contributes here. And I'm sure a lot of that would, you know, apply across a number of big fang companies, right? If you get that training once, you'd probably be able to more easily fit

into a role at a large corporation like that. And then to your point, you know, yeah, there are probably more people who are in the role of mentor at those big places who have been there 5, 10, 15 years and, you know, maybe enjoy the cushier role of middle management and guiding young folks through and, you know, not themselves being day in, day out trying to build something specifically on the product side. Yeah. I mean, if you're an intern for summer at Google as an engineer, you know, you're going to end up most likely working on some sort of toy problem. Yeah. You're not going to be contributing to production code.

Like, it's just like the ramp up time is too long to get there. So they have to give you something smaller. That's probably never going to see the light of day versus a startup. There's no difference essentially between the intern contributions and like anybody else does a full-time employee because like, if you're not adding value, then, you know, kind of why are you here at this point? Right. I mean, you know, I like to know what you think. I, you know, I think some of it comes down to personality. Like, you know, kind of why you're here at this point. Right. I mean, you know, I like to know what you think. You know, I think some of it comes down to personality. Like, you know, we both have kids. I think of myself as being a little bit maybe risk averse. You know, I was never the person who dropped out of college because I had an idea and decided to found

something and slept on a couch. You know, that wasn't me. But, you know, there's risks to both sides, right? At a startup, the risk is a little bit more maybe financial. You know, you're taking a flyer on a lower wage to get shares, which I know what you want to talk about later, to get equity in the company that may end up being worthless, right? Maybe your healthcare is not as good. But your ability to contribute and probably to be light of day or get built, but just not get traction that, you know, is up to the global scale they were looking for. And so it just gets sunset, you know, so you may end up doing a lot of work and then feeling sort of unsatisfied that, you know, it didn't really lead anywhere. Yeah, absolutely. I mean, there's a, you know, just from my own, going back to my own experience at Google, like there's a lot of Google products that are, you know, dead somewhere because the bar for success is very, very high. You know, they have essentially a hundred billion dollar

ads business. And if it's not something like it takes a lot of money to make any kind of dent in that, whereas a startup, every single like dollar that you're collecting is impactful, especially in the early days. And they can afford to take a flyer on a lot of experiments. You may think it's great because they're like, yeah, of course, go out and build it. Like, let's see what happens. But, you know, it's, you know, for them, it's not even a rounding error. So, you know, it's not like they feel like they need to release it if it doesn't blow their, blow them away. Yeah, absolutely. And then I think from the risk perspective, at least, you know, I might have, maybe I just have like a high risk tolerance. Like even when I was founding my own company, you know, I left a career basically in academics to do that. And I never really felt the pressure of the risk, I guess, because I felt like I had a skill set that even if this doesn't work out, I could always go and find something, right? Like, of course, I want to work hard and make it successful.

But I always thought like, you know, I'm going to have an opportunity to make money. Those jobs are always sort of available. So it was worth like potentially putting some time into this where I am, especially as a founder, you know, in the early days making significantly less than, you know, market rate. But even from a startup perspective, I think now the amount of investment that startups are getting is much higher than it was back when, you know, I was doing my company. Like back then, a seed round was in the hundreds of thousands of dollars. Now you're seeing pre-seed rounds of like $50 million. So I think people are paying more close to like market rate in terms of salaries, but the trade-off is that you can't essentially cash in options until there's some sort of liquidation event. So there is, of course, so I think it's like, you're not quite

at the stage where you need to be sleeping on your buddy's couch and you're all living in a house, unless you're like maybe the first founding engineer and the company hasn't raised any money. But I think even for companies that are in the series A, B, C range, you can still get a lot of the value of being a startup engineer with the potential growth, the excitement of all the scale and the new challenges and problems without necessarily, you know, living on top ramen and not being able to save anything for the future. Right, exactly. I mean, you know, as someone who is formerly a journalist and worked in digital media, you know, I don't think I felt the same way, right?

Like, I do think one nice thing, if you're able to educate yourself in the world of computer science and software development, is you can always say, well, you know, I might lose this job, but, you know, there's always more demand than supply when it comes to talented engineers. And so, you know, I'll find my way to something next. I wonder if that's true right now. Like, I do know that, you know, for the last year across the big tech companies, there were layoffs and hiring freezes. And maybe for the first time in a long time, you know, it wouldn't have been as easy to make that argument to say, like, look, you know, you're going to get laid off today, but there'll be 100 recruiters in your LinkedIn inbox and you'll get picked up somewhere tomorrow. Maybe you could find something,

but it might not be commensurate with the salary or seniority that you had before. And I don't know if that's a blip or if that, like I said, is going to continue. Like, I think a lot of that has to do with big macro factors like inflation, you know, that don't know if that's a blip or if that, like I said, is going to continue. Like, I think a lot of that has to do with big macro factors like inflation, you know, that don't really necessarily have to do with the world of technology. But yeah, you know, I think like definitely from my perspective of that last 10 years, it was like software engineers can afford to take risks, right? That's one of the nice things about the career is that, you know, in the end, if it doesn't work out, there's every, every company needs software engineers, a supermarket, a car company, an airline, everybody's going to need a great

software engineer in the end. I wonder to what degree that's still true. Yeah. I mean, I definitely think that there's been, there's sort of normal, you know, economic things where you have these growth cycles and then you essentially have the contraction. You had that, you know, economic things where you have these growth cycles and then you essentially have the contraction. You had that, you know, even going back over 20 years ago to the dot-com boom and then the dot-com bust. But they cycle around again. Even if you look at, I think, the last year and a half where we've had a crunch in the market and a, you know, reduction of valuations now all of a sudden though there's the gen ai lm world that's like blowing up that those companies are getting essentially valued at those 2021 valuations like the rules don't apply to those companies all of a sudden so the it's almost like the contraction

happened but it was uh i mean i don't know i looked at the the full uh spectrum of things but it feels like the expansion is happening again already, even though it's only been, you know, maybe 12 months. You have to be the kind of, you know, resume Jedi who can move from mobile to VR to web three to AI and always, you know, be extremely qualified for whatever hype cycle we're in, you know, and some people are very good at making those transitions. So more power to them. That's one of the values, though, of I think having that startup experience is you are able cycle we're in, you know, and some people are very good at making those transitions. So more power to them. That's one of the values, though, of I think having that startup experience is you are able to essentially have more opportunities to kind of skill stack. So you become more adaptable. And I think, you know, actually, that's one of the things I wanted to ask you about is, you know, what are sort of the qualities or skills that you think make someone successful and thrive in a startup environment versus big tech? Because it's not for everyone. Yeah. I mean, like I said, I do think a

certain amount of it is about initiative and where you feel comfortable. You know, some people feel more comfortable getting an assignment from a manager. You know, this is what I want us to accomplish. And, you know, we have sprints and story points. And when you get to the end of that, somebody will tell you, hey, I think you did a great job. And that's a pat on the head and it feels good. And maybe it comes with some other rewards. Whereas when you're at a startup, you may try two or three or four things that go nowhere, and you're trying them based on the ideas that you and a few other team members have come up with. And that can be very harrowing to think like, are we going to figure this out? Are we going to get the product market fit? Are we finally going to get traction? Are we going to get noticed in the press? little bit and are a little bit, you know, more comfortable with taking the initiative, the startup role is more for them.

I guess the other thing I would say is like my experience inside of startups and, you know, you'd have to let me know compared to big companies is that, like we said, getting things done, right? You know, GSD is what matters in the end and is going to probably going to be very visible and hard to miss. And that was definitely true at DJI. You know, they really encourage people within the engineering department to come up with prototypes, you know, to like spend time at internal hackathons and, you know, see if they could bring to the attention of the executives something that might be the next big gadget. That was encouraged. DJI, I don't know if you would call it a startup.

It had a ton of employees, but that was certainly the culture there. And that's very different from I'm assigned to a product that's inside of a portfolio that, you know, generates billions of dollars. And we might incrementally move the needle by changing this part of the camera function, you know. And so, you know, I think, yeah, like succeeding in some of those bigger places is maybe as much about your political and social skill as it is about your technical talent, if that makes sense. Yeah, I definitely think that's the case, at least in my experience, is that as you level up, a lot of your job starts to become thinking about, you know, how do I essentially gain visibility for my projects to prove the impact that I have? But when you're at a 100-person

organization, if you're impactful, everybody knows it. Like, there's nowhere to hide. And if you're impactful, everybody knows it. Like there's nowhere to hide. And if you're not impactful, you know, there's a negative consequence to that where there's basically nowhere to hide. So people are going to know, but the advantage there is that your projects can have legitimate company level impact and it's not, you could focus kind of on the work rather than selling your work. Yeah. Yeah. It's interesting. We had a cat Hicks from plural site on the podcast. I think it was like last week and they had done a survey with developers about, you know, what, like what makes people feel like they're thriving at work. And one of the big things that engineers brought up was recognition and agency. And that for a lot of folks, especially in larger companies,

they didn't feel like the work they did really got noticed. And that might've been because it was the research work that went in ahead of time, or it was, you know, the testing that went in before production, or it was some code inside of a huge, you know, product where like, you know, there's not a list of, you know, it's not like a video game where at the end, you know, there's this titles credits that say everybody who worked on every pixel. Right. And so, you know, that was something that really made the difference for sort of developer happiness and productivity was like, am I getting recognition for the work I'm doing? And so, yeah, I think there's a big difference between a big company

and a small company when it comes to that. You know, I guess like maybe another thing to say about that is that's why open source is so appealing to everyone, right? Like you can go and make a little change in the doc, make a, you know, point out a typo in the documentation and now you're part of this big project and it shows up on your GitHub and, you know, you can put that on your CV. And as you grow more and more in the open source world, you know, it's up to you to determine how visible you are. And so I think that's one of the things that maybe draws developers to that, you know, that ecosystem. Yeah. I think the same thing in many ways that draws people i think to open source is what draws people to working at startups too because it's more sort of you know

passion driven or mission yeah like no one's that's unless it's your day job to contribute to open source like you're doing it because you're interested in it or because it's something that brings you like personal satisfaction and you know joining a you know 10 person or 50 person or 100 person startup you're making a choice to sort of buy into the vision of that company and and that's a great thing if you believe in it because it's fun to be part of a system where everybody feels passionate about it where in the world of i think like the fang companies or big tech like sure some people are there because they you know believe in the vision of, I think, like the Fang companies or big tech, like, sure, some people are there because they, you know, believe in the vision, but there's people there for lots of different

reasons and that's okay, but they're not necessarily there because it's like, oh, I love the, you know, vision of, of organizing the world's information in the context of Google, but like it's, they're there because they, they like the prestige or the benefits or the work life balance. And that's totally fine, but it's just a completely different beast than joining a small organization. Yeah, for sure. I mean, I guess like one of the things that I think about when we talk about like,

what is it that inspires you as an engineer? The mentality right now, I don't think, as you pointed out, is where it was in the dot-com days or where it was maybe in part of the web three days where you felt like I could land somewhere. And within a few years, like I might be on a rocket ship. Like I might have a lottery ticket. Even with these AI startups, I feel like maybe you think I'm going to be really well compensated

and contribute, you know, in a meaningful way to some technology that's going to be amazing. But I think right now, at least, you know, people realize that there's no like quick win. You know, I don't think that's the way the tech ecosystem appears right now. And maybe that's a good thing, like you said, to have those cycles and for that to be the cycle that we're in right now. Yeah. And I think if you're joining a startup because you're hoping for like the payday and that's like your main motivating factor, there's much easier ways to make money.

Yeah, I'm still holding onto some paper options that I bought from my former employers in the world of digital media. And it's been five years and they're worth less than what I paid for them then. So I'm not hopeful I'm not, I'm not hopeful. Um, and you know, I know you wanted to talk about some of that stuff, you know, like RSUs and, you know, startup equity. I mean, um, I do think that, um, it's very difficult to get to the liquidity event. Like you see the wins, you know, it's the confirmation bias. You see the wins, uh, they get touted in, you know, all wins, you know, it's the confirmation bias. You see the wins, they get

touted in, you know, all the, you know, the press and, you know, you hear about people who go from there onto the next big thing. But most startup equity, you know, goes basically to zero because even if, you know, and this is an important point, even if the company gets acquired, you know, there's a preference stack of investors and, you know, maybe executives who will get paid out, you know, before you do as just, you know, maybe executives who will get paid out, you know, before you do as just, you know, somebody who works there. Yeah, absolutely. I think though, the like one thing that's important to understand, and we can get into the specifics of some of the, like the, the stuff around options and RSUs, but there is also like the intangible values that you get from

being part of a successful startup, even if you don't necessarily get that big like paycheck at the end of the day. If you're part of a company that goes public, even if you're there really late, you know, it's, it's a credibility factor. Totally. And, uh, and people are going to look at sort of the pedigree of your resume to evaluate how much, how well they, you know, how great they think you are and, you know know, fair or unfair, that's kind of how the world works to some degree. So, and then the other thing is, there's also a lot from an education standpoint that you get, like we've been talking about,

you have this chance to like skill stack and make yourself more adaptable. When it comes to, you know, someone thinking about moving into the world of startups, whether that's from college or moving from big tech into startups, like how do you think they should be thinking about how do I evaluate the options I have? How do I know whether this

company is a good company to be a part of even beyond just like thinking about the potential financials of it, but how do they evaluate the experience? Right. I mean, I guess one thing I would say is that, you know, you never know, you know, if you're going to make the right bet and your startup is going to be the winner or not. So what's most important really is transparency. And I've worked at, you know, a few different places. And one of the things that I think is super commendable about Stack Overflow is the level of transparency employees have, you know, into the business and its goals and its targets and its results. And, you know, that I think gives you at least a clear sense of where you're at. So you its results. And, you know, that I think gives you

at least a clear sense of where you're at so you can make educated decisions, you know, on a six, you know, looking out, you know, six months or a year, like, is this still where I want to be? Do I want to commit and why? You know, I think if you don't have that transparency, you know, or if you feel like the startup you're at,

you know, is playing games with its numbers or, you know, if what they're saying in public doesn't match up to what you're seeing in private, you know, is playing games with its numbers, um, or, you know, if what they're saying in, in public doesn't match up to what you're seeing in private, um, you know, that's a big red flag that I think people should use, um, to probably say like, I, you know, I may not know where this is going to end, but, you know, chances are that, um, you know, I'm, I'm not going to have the, um, sort of, you know, fair warning I need to make a good decision for myself, right? Yeah, I think that's really good advice. Like I think, and there's lots of ways of testing that during the interview process.

Like you can ask about, you know, if they've raised money, you know, what was their last valuation? If they give you an options package, you can ask for, you know, what does that mean in terms of what the value of the company today and so forth. And if they are cagey about that, I think those are red flags. I think some of the other things that are useful to look at too is, you know, team quality. Like what is sort of the backgrounds of the founders? Like what is their story? Is this the first time they're doing this or is this, you know, the second or third time? And if they'd only done it the first time, like, what did they do before? And what gives you a sense for that these are the right people to solve the problem?

Just like, you know, someone who's investing in a company financially is going to look at those types of things. You should be looking at that, especially in the early stages. It's really hard, I think, to judge, you know, what it's going to be like to work at these companies when they're early because you just don't have that much information to go on. And you probably don't know somebody necessarily that works there. So there's some risk associated with that. But there are ways to kind of, you know, just like they're going to do background checks on you and reference checks, you should be doing that on them as well. It goes both ways. Yeah. One trend that I think is interesting in the world of software engineering is the idea that if you, you know, get into the later stage of potentially working at a company, they might

pull you in and say, you know, for a week, you're going to work with us on this project. Like we're trying to get from A to B this week. And, you know, we're going to share, you know, this repo with you and you're allowed to, you know, throw in some PRs or like see how we work. And that I think can be super valuable. Some companies even, you know, which is great, would pay people for that. Like Paul Ford used to be on the podcast with me in a post-light, you know, they would say, we want you basically to come in and work as if you worked here for a week and we're going to pay you for your time. And after that, you know, both of us, both the employee and the employer will have a chance to sort of say, like, I think this is a good fit, right? Yeah. It's like stonching at a restaurant, essentially. Yeah. I mean, it makes a ton of sense. And I think another way to look at it,

too, and I always guide this with people who are hiring, especially hiring for the first time, is like when you're evaluating a candidate, essentially essentially it's never probably going to be better than the phase that you're interviewing like because essentially the candidate is performing for you they're trying to put the best foot forward that goes the same way for the company so if your experience interviewing the company is like not that great well they're like performing for you at this point they're trying to essentially recruit you they're trying to do the best job so if that experience is not great it's probably not getting a whole lot better if you do actually join. Right. I mean, yeah, you know, a lot of people now spend a lot of time doing

essentially practice tests that they think are going to show up on the technical challenges in the technical interview. Right. So and another that's another reason why it might be good to actually have somebody kind of work with you on your own project, you know, try to figure things out in your own code base. Because people, like you said, are putting their best foot forward after having, you know, spent, you know, three, four or five weeks on the leak code, you know, trying to see if they can, you know, get themselves in shape to ace that technical interview. Yeah.

Yeah. So I think these are all like things that as a candidate, you need to be paying attention to. So we mentioned, you know, the sort of the idea of, you know, options and what those kind of mean in the context of a startup. So, you know, I have lots of friends

that went directly from college to big tech and they're kind of used to this, you know, getting a salary, getting a bonus, getting RSUs, it's kind of like all ways of essentially generating cash. And they don't really even understand how to think about an offer from a startup and what it means for them. So how should an engineer that's maybe moving from

big tech with RSUs or even for college think about evaluating options? Yeah, again, I mean, I think if you're going to a startup, you should, you know, in your mind say, you know, there's a good chance that these may be worthless or that they may be illiquid, not worthless, but illiquid for a very long time. And so maybe you have built up a financial cushion after working at a big tech company, or maybe you're early in your career and you don't, you know, you don't have a mortgage and a family to support. And so you're less concerned about that. You know, I think it would probably be stressful. Yeah. To go from a big tech company where you're getting uh you know like you said

compensated in ways that are kind of transparent you can look up the share price you know every day and see what it's going to be like um and you know you know when the quarter's going to end and things are predictable to a startup where you know they it's unpredictable when they may raise their next round and at what valuation right um and so i think that's something you have to do eyes wide open. It's not, you know, something that you can sort of just hand wave away. And then but there are a few things, like I said before, that I think you can do. And, you know, if a place has been around for a while, you can ask folks if, you know, during previous rounds, they let folks cash out a little bit. So some startups do try to give their employees some liquidity or, you know, if it's a well-known startup, you know, is there a secondary market for this, which is another thing that can happen where, you know, you can have that option to move your shares there to other people who want

to sort of take a bet on that company or they want to get into the equity before it goes public. And so that would be a way for you, like, you know, that'd be a way, like you said, to basically take cash out, even if the company itself doesn't get acquired or go public. Yeah. And I think the other thing to think about too is that there's, even within the world of startups, there's a huge variation in terms of what a startup really means. Like it's very different from joining a company that's like less than 10 people and they don't even have a product versus, you know, joining essentially a pre-IPO company where the IPO is like imminent and they don't even have our product versus you know joining essentially a pre-ipo company where the ipo is like imminent and they're just waiting for the right time to come public right so and the options that you have available for uh liquidity and cashing out like secondary markets

and so forth changes at the stage of the of the company and i think it's a good thing to kind of map like where you are what you want to get out of that journey and experience. And also what your comfort level is from like a financial perspective and risk perspective with where that company is in their journey. Right. I'm not going to, yeah, I think both those things are true. I'm not going to name any names, but some companies have been, you know, have filed their papers and are waiting for their IPO window.

And it's been years now, you know, it just, and it hasn't been the right time or when it was the right time, you know, their business was not in the right place, you know? So, um, you know, that is an unfortunate thing that can happen with startups. Um, and obviously I think, like you said, you know, the flip side is I was employee 10 at company X and everybody's heard of company X now, you know, that's a huge, uh, you know, blue ribbon on your resume and that's going to open a ton of doors for you right yeah i mean i think having the sort of the those things on your resume they get you uh basically an interview with any company in the world like it might not land you the job but it gets you sort of the goodwill to pass through you know whatever black box system they're using for evaluating resumes and it even gets to a point where people are like actively trying to recruit you rather than you having to go out and like source

those opportunities. Yeah. So in terms of, you know, a startup success, like recruitment is a big challenge. How do you, what kind of strategies have you seen that are effective for companies to recruit and nurture talent and sort of maintain the culture of their company through competitive cycles? Yeah. I mean, I think that you probably have some thoughts on this because you've been in this world, but I think great DevRel is about getting really talented people who have a passion for engineering and love building projects, but are also good up on stage and can give a demo or give a great talk, you know, are great on social media and don't mind sharing their work and having a back and forth with folks. So I think that's

probably one of the most effective ways is like an engineer sees another engineer that's built something cool that's, you know, they can contribute to, or they see a talk that they feel like they learned from that's going to build a lot of goodwill, you know, towards the organization. You know, I think that that's kind of what my job is inside of Stack Overflow, right? Like make sure we have a great engineering blog, make sure we have great guests on the podcast, make sure the newsletter is interesting. And hopefully that will be entertaining and informative to developers most of the time and every once in a while, you know,

they'll see that we're hiring or they'll see we've launched a new product or something like that. And then one thing that has come to mind recently, I did an interview recently with someone who's on the Python Steering Council and works at Bloomberg as part of the podcast. And, you know, he did not initially come in as a Python expert. He was a physicist, then he went to Bloomberg, then he started working more Python. And over time, like you said, that just became his passion. He essentially working two jobs he got all the way to the steering council now he's helping guide the future of this major language and so they essentially said at bloomberg you can take 50 of your hours and work on that you know like we're going to pay you to be partially internal

and partially external to this open source organization and that's a big draw people want to go to work at Bloomberg knowing on day one, when the new version comes out, we're already going to know all about it and get, you know, to play with it. Or, you know, like this is a place where the people who are guiding the future of this language that, you know, is my, is sort of my chosen one are working and I can, you know, give, give, give them ideas that might help shape it. So I think, you know, that has been a very successful strategy for companies, you know, but, you know, and you can name some, you know, that has been a very successful strategy for companies, you know, and you can name some, you know, your TypeScript, your React, your Go. You know, I think that that is a really interesting strategy to approach for a company to embrace open source and to encourage their, you know, developers or engineers to work in that so that they can, in that way, reach a really broad community of folks who might be interested in working at that company and show their technical acumen. Yeah, I think, you know, one of the things you touched on is on the developer relations side, but even for a business that isn't necessarily developer focused, the content, I think,

plays a big factor in people's perception of your company. Like, you know, we are a developer focused company at Skyfo, but we hear all the time from candidates that they you know learned about the company through the content or they got pinged by a recruiter and then they looked at some of the content whether it was a video a podcast a blog post or something like that and then they they basically it felt good to them they're like oh right these are my people so you know i want to work here now yeah exactly and i think as you are able to recruit more great people of course like a players attract other players and they know people within their network that they can refer which then becomes like a an engine for your your recruitment um arm and then

i also think that the uh having sort of everyone understand that there's a marketing component to recruitment and interviewing. Right. You're representing your company when you're doing that. So even if a candidate is not the right fit and maybe they're even a disaster in the interview, you want that person leaving feeling like they've been respected, that they had, that they, you know, were given a fair chance and they're excited about the company, even if that leads to a decision where they don't ultimately get the job. Completely. I mean, you know, if you go to our programming one day and you're reading a horror story thread about, you know, a really bad interview where the people

felt like, you know, they were bullied or, you know, like they just weren't listened to, you know, you're going to want to tune that company out if it gets, you know, if it's called out and that kind of thing. So I think that's super important. And yeah, I mean, to your point about content, you know, I think within a startup, it's maybe a little bit easier to sort of say like, this is exactly what we're working on and this is what we're all about. And if you care about these things, you know, you should come here at a big company. You know, I think that's one of the reasons that they, you know, may invest in that or, you know, come work with Stack Overflow. We do sponsor podcasts and blogs is to say like, well,

what's the developer experience really like inside this huge org? Like, can you tell us about a project that you worked on that, you know, got, you know, time from idea to production down from 30 days to, you know, a couple of hours. And if somebody hears a story about an engineer solving a problem, you know, that might give them perspective on what it's actually like to work inside that big organization versus kind of this, you know, vague, amorphous sense that it would be good to work at this place because it's well known and, you know, about high technology. Yeah, I think that there's something part of the interview process you should be looking, it's an opportunity for you to sort of test the people that are interviewing with you, whether you feel like you have,

this is a learning opportunity for you. You don't necessarily want to come in thinking that like, oh, well, I need to teach these people because I have no idea what they're doing. Like, that's probably not a good place to be versus coming in and being like, oh, wow, I could really learn something here, especially if you're early in your career. Yeah. And we've talked about this a few times on the podcast, but it can be really great. You know, I know a lot of engineers get frustrated with the amount of recruiters in their inbox, but take interviews when you're at a point in your career where you don't want to leave the job, or you don't need to leave the job just to practice that. And interviewing the interviewer

and turning things around where it's like, I don't need to feel any stress in this interview. You know, it's not, I'm not going in here because I want this job. I'm going in here to like, just stay sharp in this mode, right? Like to be able to talk organically about what I would want at a company and, you know, what would make me really happy there. And, you know, that's different than like you said,

well, I got to perform, you know, I need this job. I have to put my best before I'm going to say what I think they want me to say. Yeah. So, you know, as we start to wrap things up,

just kind of looking big picture, even outside of, you know, as we start to wrap things up, just kind of looking big picture, even outside of, you know, career advice for people looking to move to startups. In the world of startups, what kind of, is there, you know, a big problem that you would love to see a startup, you know, try to solve essentially? Like what is, you know, some issue that you would love to see somebody, you know, come up with a product that would ease your life or you'd be excited about? I think the one that I was most interested in was TXYZ, I think it's called T. It's from the creator of Homebrew. And the problem he was trying to solve essentially was how do you compensate the contributors and maintainers of open source projects? How do you make sure that the people who have built, you know, this widget, which now is holding up 90% of the internet as XKCD would tell us, you know, don't get burned out and leave that and just leave that project, you know, sort of flailing in the wind. So I thought that was a cool one. I think it combines, you know, a little bit of blockchain, but not in a bad way with the idea of supporting open source, which I think we can all get behind. And that has been, you know,

a problem that's been discussed in the five years I've been here a number of times on the podcast is like, what, you know, what's the best way to have an open, a healthy open source ecosystem? So I think if a startup thinks that's, you know, the product they can build,

that's a cool idea. Yeah, that's really cool. I love it. Ben, thanks so much for being here. I think people are going to enjoy this. I know I enjoyed it. So, you know, at the very least, I'm satisfied and happy. Great.

Hopefully we're able to help someone out there that's kind of navigating the world of startups and understand, you know, their opportunities that they have a little bit clearer. So thanks so much for being here. Cheers. Yeah. Thanks so much for having me on. I really appreciate it. And I enjoyed the conversation.