The Developer Red Flag Most Founders Miss

You can now hand a brand new developer a You can now hand a brand new developer a codebase you've built alone for months codebase you've built alone for months codebase you've built alone for months or even years and get them up to speed or even years and get them up to speed or even years and get them up to speed fast. An AI agent reads the whole thing, fast. An AI agent reads the whole thing, fast. An AI agent reads the whole thing, the history and the reasoning included, the history and the reasoning included, the history and the reasoning included, and hands over the context that used to and hands over the context that used to and hands over the context that used to live in your head. That onboarding live in your head. That onboarding live in your head. That onboarding process used to take weeks of manually process used to take weeks of manually process used to take weeks of manually walking someone through a codebase. So, walking someone through a codebase. So, walking someone through a codebase. So, one half of hiring your first developer one half of hiring your first developer one half of hiring your first developer just got a lot easier. What hasn't just got a lot easier. What hasn't just got a lot easier. What hasn't changed is the other half, actually changed is the other half, actually changed is the other half, actually picking the right person. get that wrong picking the right person. get that wrong picking the right person. get that wrong and there's no tool that saves you from and there's no tool that saves you from and there's no tool that saves you from the wasted months and the wasted runway the wasted months and the wasted runway the wasted months and the wasted runway you just burned. So I sat down with you just burned. So I sat down with you just burned. So I sat down with Derek Rhyr. Derek and I started Drip Derek Rhyr. Derek and I started Drip Derek Rhyr. Derek and I started Drip together, built it up and eventually together, built it up and eventually together, built it up and eventually sold it. And along the way, we hired an sold it. And along the way, we hired an sold it. And along the way, we hired an entire engineering team. He's since gone entire engineering team. He's since gone entire engineering team. He's since gone on to found Savvy. So between the two of on to found Savvy. So between the two of on to found Savvy. So between the two of us, we've hired a lot of developers and us, we've hired a lot of developers and us, we've hired a lot of developers and learned a lot about what to scream for. learned a lot about what to scream for. learned a lot about what to scream for. Let's start with a question from Let's start with a question from Let's start with a question from Michael. I founded an accounting source Michael. I founded an accounting source Michael. I founded an accounting source for Swiss freelancers four years ago and for Swiss freelancers four years ago and for Swiss freelancers four years ago and I'm currently at around 24K MRR and I'm I'm currently at around 24K MRR and I'm I'm currently at around 24K MRR and I'm thinking about hiring my first developer thinking about hiring my first developer thinking about hiring my first developer and I have so many questions around and I have so many questions around and I have so many questions around that. So I thought I'd ask you first of that. So I thought I'd ask you first of that. So I thought I'd ask you first of all, what qualities would you look out all, what qualities would you look out all, what qualities would you look out for in the first developer you hire so for in the first developer you hire so for in the first developer you hire so that that person can actually take that that person can actually take that that person can actually take things off my plate and free up my time things off my plate and free up my time things off my plate and free up my time and hopefully take ownership of the and hopefully take ownership of the and hopefully take ownership of the codebase in the long run. Also, how do codebase in the long run. Also, how do codebase in the long run. Also, how do you effectively onboard someone onto a you effectively onboard someone onto a you effectively onboard someone onto a codebase you've been the sole codebase you've been the sole codebase you've been the sole contributor to? Would you try to create contributor to? Would you try to create contributor to? Would you try to create some sort of documentations or just dive some sort of documentations or just dive some sort of documentations or just dive into it and try to teach them on the go?

into it and try to teach them on the go? into it and try to teach them on the go? And also, do you have any other tips on And also, do you have any other tips on And also, do you have any other tips on how I can derisk choosing the wrong how I can derisk choosing the wrong how I can derisk choosing the wrong person and wasting time and money and person and wasting time and money and person and wasting time and money and making the onboarding process as smooth making the onboarding process as smooth making the onboarding process as smooth as possible so that the person can get as possible so that the person can get as possible so that the person can get effective as soon as possible? effective as soon as possible? effective as soon as possible? >> So Derek, I'm going to kick this to you >> So Derek, I'm going to kick this to you >> So Derek, I'm going to kick this to you first. He has several questions. So first. He has several questions. So first. He has several questions. So let's maybe tackle first. What qualities let's maybe tackle first. What qualities let's maybe tackle first. What qualities would you look for in the first would you look for in the first would you look for in the first developer you hire so that person can developer you hire so that person can developer you hire so that person can actually take things off your plate, actually take things off your plate, actually take things off your plate, free up your time, and hopefully take free up your time, and hopefully take free up your time, and hopefully take ownership of the codebase in the long ownership of the codebase in the long ownership of the codebase in the long run? run? run? >> As I was thinking about this question, I >> As I was thinking about this question, I >> As I was thinking about this question, I pulled up my most recent job description pulled up my most recent job description pulled up my most recent job description when I was hiring uh my latest full when I was hiring uh my latest full when I was hiring uh my latest full stack dev who replaced my first stack dev who replaced my first stack dev who replaced my first developer for Savvy. So, kind of running developer for Savvy. So, kind of running developer for Savvy. So, kind of running running through the list of things that running through the list of things that running through the list of things that I was listing in this cuz I sort of use I was listing in this cuz I sort of use I was listing in this cuz I sort of use the job description as my spec for the the job description as my spec for the the job description as my spec for the things I'm going to be evaluating things I'm going to be evaluating things I'm going to be evaluating against. You know, I guess first piece against. You know, I guess first piece against. You know, I guess first piece is like experience obviously like if is like experience obviously like if is like experience obviously like if you're hiring somebody to kind of be in you're hiring somebody to kind of be in you're hiring somebody to kind of be in this technical founder handing off this technical founder handing off this technical founder handing off control of the codebase or part of control of the codebase or part of control of the codebase or part of control of the codebase to somebody, you control of the codebase to somebody, you control of the codebase to somebody, you want them to have a decent amount of want them to have a decent amount of want them to have a decent amount of experience. Obviously, budget experience. Obviously, budget experience. Obviously, budget permitting. If you're super early stage, permitting. If you're super early stage, permitting. If you're super early stage, maybe you can't afford that. With Drip, maybe you can't afford that. With Drip, maybe you can't afford that. With Drip, we ended up training developers um we ended up training developers um we ended up training developers um because we were budget constrained.

because we were budget constrained. because we were budget constrained. >> That's something I would recommend. >> That's something I would recommend. >> That's something I would recommend. Yeah, if you can avoid it, I would avoid Yeah, if you can avoid it, I would avoid Yeah, if you can avoid it, I would avoid it. it. it. >> So, I was looking for someone with a >> So, I was looking for someone with a >> So, I was looking for someone with a minimum of 5 years experience as a minimum of 5 years experience as a minimum of 5 years experience as a software developer just sort of as it's software developer just sort of as it's software developer just sort of as it's an arbitrary number, but you know, an arbitrary number, but you know, an arbitrary number, but you know, senior level and someone with a full senior level and someone with a full senior level and someone with a full stack skill set. So this was like really stack skill set. So this was like really stack skill set. So this was like really trying to hone in on someone who is a trying to hone in on someone who is a trying to hone in on someone who is a generalist who's comfortable generalist who's comfortable generalist who's comfortable conceptualizing a feature from front end conceptualizing a feature from front end conceptualizing a feature from front end to back end and not somebody who's a to back end and not somebody who's a to back end and not somebody who's a specialist. I think about like when we specialist. I think about like when we specialist. I think about like when we were later stage at Drip, we started were later stage at Drip, we started were later stage at Drip, we started hiring, you know, backend engineers and hiring, you know, backend engineers and hiring, you know, backend engineers and JavaScript developers and these people JavaScript developers and these people JavaScript developers and these people who were like hyper specific on their who were like hyper specific on their who were like hyper specific on their skill set and could really own, you skill set and could really own, you skill set and could really own, you know, part of the stack, but that's know, part of the stack, but that's know, part of the stack, but that's going to work against you if you're going to work against you if you're going to work against you if you're trying to like offload trying to like offload trying to like offload any and all development tasks to uh to a any and all development tasks to uh to a any and all development tasks to uh to a number two. I put thrive working number two. I put thrive working number two. I put thrive working autonomously um because I think that's autonomously um because I think that's autonomously um because I think that's interesting. my previous podcast co-host interesting. my previous podcast co-host interesting. my previous podcast co-host Ben Orinstein, founder of Tupil pair Ben Orinstein, founder of Tupil pair Ben Orinstein, founder of Tupil pair programming app. A lot of uh a lot of programming app. A lot of uh a lot of programming app. A lot of uh a lot of developers enjoy pair programming developers enjoy pair programming developers enjoy pair programming regularly. Some people are accustomed to regularly. Some people are accustomed to regularly. Some people are accustomed to doing it all the time or just, you know, doing it all the time or just, you know, doing it all the time or just, you know, constantly collaborating on features.

constantly collaborating on features. constantly collaborating on features. >> And so, you know, this is something like >> And so, you know, this is something like >> And so, you know, this is something like you probably as the founder don't have you probably as the founder don't have you probably as the founder don't have time to be pair programming all the time time to be pair programming all the time time to be pair programming all the time on stuff. And bringing in a a lone on stuff. And bringing in a a lone on stuff. And bringing in a a lone engineer, you know, not everyone is cut engineer, you know, not everyone is cut engineer, you know, not everyone is cut out for that like flow of working. Like out for that like flow of working. Like out for that like flow of working. Like some people just really thrive on a team some people just really thrive on a team some people just really thrive on a team and don't work so well independently. and don't work so well independently. and don't work so well independently. So, um, I think that's another important So, um, I think that's another important So, um, I think that's another important one, assuming that you're just hiring one, assuming that you're just hiring one, assuming that you're just hiring one developer to start. Um, one developer to start. Um, one developer to start. Um, >> for sure. >> for sure. >> for sure. >> And then confidence to ship. What I'm >> And then confidence to ship. What I'm >> And then confidence to ship. What I'm trying to get at with this is sort of trying to get at with this is sort of trying to get at with this is sort of like a a a tamed perfectionism. Like, like a a a tamed perfectionism. Like, like a a a tamed perfectionism. Like, you want someone who pays attention to you want someone who pays attention to you want someone who pays attention to the details and cares a lot about the details and cares a lot about the details and cares a lot about quality, but also is willing to accept, quality, but also is willing to accept, quality, but also is willing to accept, you know, better done than perfect and you know, better done than perfect and you know, better done than perfect and and just get stuff shipped. Because I and just get stuff shipped. Because I and just get stuff shipped. Because I think a lot of times on larger teams um think a lot of times on larger teams um think a lot of times on larger teams um maybe where there's less of a sense of maybe where there's less of a sense of maybe where there's less of a sense of urgency or just more hands involved like urgency or just more hands involved like urgency or just more hands involved like you can just spend weeks on one small you can just spend weeks on one small you can just spend weeks on one small task and making it perfect and making task and making it perfect and making task and making it perfect and making sure it checks all the boxes and um when sure it checks all the boxes and um when sure it checks all the boxes and um when you're when you're tiny startup phase you're when you're tiny startup phase you're when you're tiny startup phase you don't really have the luxury of you don't really have the luxury of you don't really have the luxury of being able to do that. So someone who's being able to do that. So someone who's being able to do that. So someone who's very very very >> biased towards action. I think the other >> biased towards action. I think the other >> biased towards action. I think the other thing I would add, tell me tell me if thing I would add, tell me tell me if thing I would add, tell me tell me if you think this is accurate still, but you think this is accurate still, but you think this is accurate still, but there's something to me about an a there's something to me about an a there's something to me about an a general agreement on the the ethos of general agreement on the the ethos of general agreement on the the ethos of how you as the founder code. And what I how you as the founder code. And what I how you as the founder code. And what I mean by this is back in the day, you may mean by this is back in the day, you may mean by this is back in the day, you may have been doing TDD, whether you're t have been doing TDD, whether you're t have been doing TDD, whether you're t test first or whether you're we wanted test first or whether you're we wanted test first or whether you're we wanted tests in the codebase. There were folks tests in the codebase. There were folks tests in the codebase. There were folks who were like, nah, don't believe in

who were like, nah, don't believe in who were like, nah, don't believe in that. Don't want to do that. I would not that. Don't want to do that. I would not that. Don't want to do that. I would not have hired them if they're not willing have hired them if they're not willing have hired them if they're not willing to do that. and and test is just one to do that. and and test is just one to do that. and and test is just one example I'm bringing up, but there's a b example I'm bringing up, but there's a b example I'm bringing up, but there's a b there's tabs and spaces. No, there are a there's tabs and spaces. No, there are a there's tabs and spaces. No, there are a bunch of things though, right? And some bunch of things though, right? And some bunch of things though, right? And some for some people, they're just super for some people, they're just super for some people, they're just super flexible, right? And they are willing to flexible, right? And they are willing to flexible, right? And they are willing to kind of go, h you want tests, great, kind of go, h you want tests, great, kind of go, h you want tests, great, I'll do it. You want tabs, great, I'll I'll do it. You want tabs, great, I'll I'll do it. You want tabs, great, I'll do it since that's, you know, the right do it since that's, you know, the right do it since that's, you know, the right way to do it anyways. Um, way to do it anyways. Um, way to do it anyways. Um, you didn't you didn't have a reaction to you didn't you didn't have a reaction to you didn't you didn't have a reaction to that. Is that not a thing anymore? that. Is that not a thing anymore? that. Is that not a thing anymore? Because I thought you were spaces. Because I thought you were spaces. Because I thought you were spaces. [laughter] [laughter] [laughter] >> Oh, I am spaces. Yeah. Yeah. >> Oh, I am spaces. Yeah. Yeah. >> Oh, I am spaces. Yeah. Yeah. >> Yeah. I just said tabs. I just said tabs >> Yeah. I just said tabs. I just said tabs >> Yeah. I just said tabs. I just said tabs is the right way to do it and you had no is the right way to do it and you had no is the right way to do it and you had no reaction. reaction. reaction. >> [laughter] >> [laughter] >> [laughter] >> you you're not even listening to me. >> you you're not even listening to me. >> you you're not even listening to me. You're backgrounding me. You're backgrounding me. You're backgrounding me. >> Anyway, >> Anyway, >> Anyway, >> running along. [laughter] >> running along. [laughter] >> running along. [laughter] >> Yeah, totally. I'm like, why? I'm >> Yeah, totally. I'm like, why? I'm >> Yeah, totally. I'm like, why? I'm waiting for the reaction. Um, but waiting for the reaction. Um, but waiting for the reaction. Um, but whatever. And you know, tabs and spaces whatever. And you know, tabs and spaces whatever. And you know, tabs and spaces and tests are just examples of this, but and tests are just examples of this, but and tests are just examples of this, but there's something I think about being in there's something I think about being in there's something I think about being in alignment and potentially having some alignment and potentially having some alignment and potentially having some flexibility and willing to change. Like, flexibility and willing to change. Like, flexibility and willing to change. Like, let's be honest, if you'd hired a senior let's be honest, if you'd hired a senior let's be honest, if you'd hired a senior first developer, you're working with first developer, you're working with first developer, you're working with them and you know, a cursor, Cloud Code, them and you know, a cursor, Cloud Code, them and you know, a cursor, Cloud Code, Windsurf, like all these tools. tools. I Windsurf, like all these tools. tools. I Windsurf, like all these tools. tools. I know wind surf like gold news now, but know wind surf like gold news now, but know wind surf like gold news now, but you know these tools came out. There are you know these tools came out. There are you know these tools came out. There are devs out there who who refuse to use devs out there who who refuse to use devs out there who who refuse to use them. So what do you do then? Like do them. So what do you do then? Like do them. So what do you do then? Like do you want that person on your team? You you want that person on your team? You you want that person on your team? You know there's some there's some type of know there's some there's some type of know there's some there's some type of flexibility and willingness to it's flexibility and willingness to it's flexibility and willingness to it's having opinions because they should have having opinions because they should have having opinions because they should have opinions if you're a senior but being opinions if you're a senior but being opinions if you're a senior but being willing to willing to willing to >> to go with the flow to let you make the >> to go with the flow to let you make the >> to go with the flow to let you make the final call to have whatever it there's a final call to have whatever it there's a final call to have whatever it there's a collaborative nature of that. Do you collaborative nature of that. Do you collaborative nature of that. Do you feel like that's a like that's something feel like that's a like that's something feel like that's a like that's something you look for?

you look for? you look for? >> Yes, for sure. And I I think it's kind >> Yes, for sure. And I I think it's kind >> Yes, for sure. And I I think it's kind of hard. It can be hard to pin that down of hard. It can be hard to pin that down of hard. It can be hard to pin that down exactly because it's like on the one exactly because it's like on the one exactly because it's like on the one hand, you don't want someone who doesn't hand, you don't want someone who doesn't hand, you don't want someone who doesn't have any opinions or any taste about have any opinions or any taste about have any opinions or any taste about things. But on the flip side, I've things. But on the flip side, I've things. But on the flip side, I've definitely spoken to developers before definitely spoken to developers before definitely spoken to developers before who are so opinionated and so strong who are so opinionated and so strong who are so opinionated and so strong willed in their convictions that they're willed in their convictions that they're willed in their convictions that they're almost hung up on that. So, like I think almost hung up on that. So, like I think almost hung up on that. So, like I think this is something that maybe would come this is something that maybe would come this is something that maybe would come out even more if you were to do like a out even more if you were to do like a out even more if you were to do like a test project with someone, which I test project with someone, which I test project with someone, which I highly recommend during a during a highly recommend during a during a highly recommend during a during a hiring process to like, hiring process to like, hiring process to like, >> okay, let's work on something together >> okay, let's work on something together >> okay, let's work on something together for an afternoon or a few hours for an afternoon or a few hours for an afternoon or a few hours >> and let's see how you react to >> and let's see how you react to >> and let's see how you react to encountering something that is maybe not encountering something that is maybe not encountering something that is maybe not done the way you would have done it, but done the way you would have done it, but done the way you would have done it, but like this is the norm established in the like this is the norm established in the like this is the norm established in the codebase and are you willing to go along codebase and are you willing to go along codebase and are you willing to go along with those norms and maybe you know with those norms and maybe you know with those norms and maybe you know recommend shifting recommend shifting recommend shifting pragmatically in a new direction if pragmatically in a new direction if pragmatically in a new direction if there's something that is truly better. there's something that is truly better. there's something that is truly better. But like also recognizing like we can't But like also recognizing like we can't But like also recognizing like we can't stop the world and rewrite the codebase stop the world and rewrite the codebase stop the world and rewrite the codebase or or or >> it doesn't make sense to fight against >> it doesn't make sense to fight against >> it doesn't make sense to fight against the conventions that we've established the conventions that we've established the conventions that we've established in such a way where like now it's super in such a way where like now it's super in such a way where like now it's super confusing anyone coming into the confusing anyone coming into the confusing anyone coming into the codebase is not able to you know to know codebase is not able to you know to know codebase is not able to you know to know how to how to operate. So how to how to operate. So how to how to operate. So >> yeah that's a tricky one. What you don't >> yeah that's a tricky one. What you don't >> yeah that's a tricky one. What you don't want to find yourself in the place of is want to find yourself in the place of is want to find yourself in the place of is like arguing small small things all the like arguing small small things all the like arguing small small things all the time because opinions are too strong you time because opinions are too strong you time because opinions are too strong you know know know >> you know this you know the person we all >> you know this you know the person we all >> you know this you know the person we all do we've worked with them not and some do we've worked with them not and some do we've worked with them not and some are developer a lot are developers some are developer a lot are developers some are developer a lot are developers some are not you know there's people in other are not you know there's people in other are not you know there's people in other [laughter] parts of the company yeah and [laughter] parts of the company yeah and [laughter] parts of the company yeah and then the other one I thought of that I

then the other one I thought of that I then the other one I thought of that I do whether they're a developer or not do whether they're a developer or not do whether they're a developer or not when hiring at even tiny seed micro comp when hiring at even tiny seed micro comp when hiring at even tiny seed micro comp these days it's almost a hard pass for these days it's almost a hard pass for these days it's almost a hard pass for me if they've only worked at big me if they've only worked at big me if they've only worked at big companies companies companies >> if they've never worked at a let's say >> if they've never worked at a let's say >> if they've never worked at a let's say sub 50 person company cuz tiny se sub 50 person company cuz tiny se sub 50 person company cuz tiny se Microsoft's 10 people right and in this Microsoft's 10 people right and in this Microsoft's 10 people right and in this case we're talking about a two or three case we're talking about a two or three case we're talking about a two or three person company or whatever I mean it'd person company or whatever I mean it'd person company or whatever I mean it'd be great if they work at like a 10 or 20 be great if they work at like a 10 or 20 be great if they work at like a 10 or 20 person company but man if someone's only person company but man if someone's only person company but man if someone's only worked at say a fortune 500 or five you worked at say a fortune 500 or five you worked at say a fortune 500 or five you know 1000 or whatever I the the change know 1000 or whatever I the the change know 1000 or whatever I the the change of mindset is so dramatic it's such a of mindset is so dramatic it's such a of mindset is so dramatic it's such a big deal that it is something I big deal that it is something I big deal that it is something I absolutely scream for absolutely scream for absolutely scream for >> do you ask folks about that >> do you ask folks about that >> do you ask folks about that >> oh for sure Yeah, I similar criteria >> oh for sure Yeah, I similar criteria >> oh for sure Yeah, I similar criteria where I'm just kind of not willing to where I'm just kind of not willing to where I'm just kind of not willing to entertain if someone exclusively has big entertain if someone exclusively has big entertain if someone exclusively has big company experience like you said because company experience like you said because company experience like you said because yeah, I think dev teams just operate so yeah, I think dev teams just operate so yeah, I think dev teams just operate so differently. I mean, even watching Drip differently. I mean, even watching Drip differently. I mean, even watching Drip grow to a team of what was it 20 20 plus grow to a team of what was it 20 20 plus grow to a team of what was it 20 20 plus when we left when we left when we left >> and then 20 25 somewhere in there. Yeah. >> and then 20 25 somewhere in there. Yeah. >> and then 20 25 somewhere in there. Yeah. Event that was just the engineer product Event that was just the engineer product Event that was just the engineer product team. team. team. >> Yeah. Yep. And so even watching how work >> Yeah. Yep. And so even watching how work >> Yeah. Yep. And so even watching how work gets organized, how things, you know, gets organized, how things, you know, gets organized, how things, you know, the pace that people work at, it just it the pace that people work at, it just it the pace that people work at, it just it morphs into a different thing, you know.

morphs into a different thing, you know. morphs into a different thing, you know. Um, Um, Um, >> yeah, >> yeah, >> yeah, >> and that's not necessarily a bad >> and that's not necessarily a bad >> and that's not necessarily a bad experience to have, but exclusively experience to have, but exclusively experience to have, but exclusively having that can be a culture shock. And having that can be a culture shock. And having that can be a culture shock. And I think some people have a harder time I think some people have a harder time I think some people have a harder time adapting to that. And it it can be a lot adapting to that. And it it can be a lot adapting to that. And it it can be a lot to reorient someone towards the small to reorient someone towards the small to reorient someone towards the small smaller company mindset and maybe you smaller company mindset and maybe you smaller company mindset and maybe you don't have the luxury to do that if don't have the luxury to do that if don't have the luxury to do that if you're if you're hiring your first dev. you're if you're hiring your first dev. you're if you're hiring your first dev. >> I remember hiring someone and and they >> I remember hiring someone and and they >> I remember hiring someone and and they got in the first day and they're like, got in the first day and they're like, got in the first day and they're like, "So, what's the process for da da da?" "So, what's the process for da da da?" "So, what's the process for da da da?" And I was like, "There isn't. ask me, And I was like, "There isn't. ask me, And I was like, "There isn't. ask me, you know, and what's the what's the uh you know, and what's the what's the uh you know, and what's the what's the uh do you have a form that I fill out cuz I do you have a form that I fill out cuz I do you have a form that I fill out cuz I I want to get like a new mouse and a I want to get like a new mouse and a I want to get like a new mouse and a keyboard and I'm like, no, just buy it keyboard and I'm like, no, just buy it keyboard and I'm like, no, just buy it on Amazon, tell me the total, I'll on Amazon, tell me the total, I'll on Amazon, tell me the total, I'll PayPal, I'll Venmo you, you know, out of PayPal, I'll Venmo you, you know, out of PayPal, I'll Venmo you, you know, out of the company account or whatever or I can the company account or whatever or I can the company account or whatever or I can >> come to my computer, put it on the >> come to my computer, put it on the >> come to my computer, put it on the thing, I'll do with the company card, thing, I'll do with the company card, thing, I'll do with the company card, you know, it's like that's that's the you know, it's like that's that's the you know, it's like that's that's the process, you know. So, it's just process, you know. So, it's just process, you know. So, it's just different mindsets. And so, his next different mindsets. And so, his next different mindsets. And so, his next question then was around he said, "How question then was around he said, "How question then was around he said, "How do you effectively onboard someone into do you effectively onboard someone into do you effectively onboard someone into a code base you've been the sole a code base you've been the sole a code base you've been the sole contributor to? Do you try to create contributor to? Do you try to create contributor to? Do you try to create documentation or do you dive in and try documentation or do you dive in and try documentation or do you dive in and try to teach them on the go? How have you to teach them on the go? How have you to teach them on the go? How have you handled this? And I'm sure this has handled this? And I'm sure this has handled this? And I'm sure this has changed over the years with with AI and changed over the years with with AI and changed over the years with with AI and all that stuff.

all that stuff. all that stuff. >> Yeah. Yeah. I think this has changed >> Yeah. Yeah. I think this has changed >> Yeah. Yeah. I think this has changed almost completely from my first almost completely from my first almost completely from my first iteration of hiring pre-AII versus post iteration of hiring pre-AII versus post iteration of hiring pre-AII versus post AI. Um so I think before before AI like AI. Um so I think before before AI like AI. Um so I think before before AI like I I recall drafting some documents where I I recall drafting some documents where I I recall drafting some documents where I was like giving a lay a high level lay I was like giving a lay a high level lay I was like giving a lay a high level lay of the land of the codebase like these of the land of the codebase like these of the land of the codebase like these are the major subsystems. I don't think are the major subsystems. I don't think are the major subsystems. I don't think I tried to put too much in writing I tried to put too much in writing I tried to put too much in writing though. It was more like on calls like though. It was more like on calls like though. It was more like on calls like let's together walk through the codebase let's together walk through the codebase let's together walk through the codebase and let me you know show you kind of in and let me you know show you kind of in and let me you know show you kind of in the editor where things are and how they the editor where things are and how they the editor where things are and how they fit together at a high level. But I fit together at a high level. But I fit together at a high level. But I think these days that is squarely in the think these days that is squarely in the think these days that is squarely in the sweet spot of an LLM and I think it's sweet spot of an LLM and I think it's sweet spot of an LLM and I think it's just so much easier in general to get just so much easier in general to get just so much easier in general to get onboarded into a codebase because you onboarded into a codebase because you onboarded into a codebase because you can literally fire up an agent and just can literally fire up an agent and just can literally fire up an agent and just start asking questions about the start asking questions about the start asking questions about the codebase. I was going to ask that codebase. I was going to ask that codebase. I was going to ask that because I haven't done I mean I've used because I haven't done I mean I've used because I haven't done I mean I've used claude code to do some little you know claude code to do some little you know claude code to do some little you know pitly projects and stuff index all the pitly projects and stuff index all the pitly projects and stuff index all the podcast episodes blah blah blah but I podcast episodes blah blah blah but I podcast episodes blah blah blah but I have not you can just ask it like what have not you can just ask it like what have not you can just ask it like what are the major subsystems and yeah of are the major subsystems and yeah of are the major subsystems and yeah of course of course you can that is course of course you can that is course of course you can that is incredible wow incredible wow incredible wow >> it's [laughter] like we live in the >> it's [laughter] like we live in the >> it's [laughter] like we live in the future future future all right and so that's it so at this all right and so that's it so at this all right and so that's it so at this point you'd be like point you'd be like point you'd be like >> it's ask cloud code or ask your ask your >> it's ask cloud code or ask your ask your >> it's ask cloud code or ask your ask your coding tool coding tool coding tool >> basically and you give them a you'd >> basically and you give them a you'd >> basically and you give them a you'd obviously give them an overview I mean obviously give them an overview I mean obviously give them an overview I mean we used to pull someone in for an power we used to pull someone in for an power we used to pull someone in for an power on the whiteboard, right? And be like, on the whiteboard, right? And be like, on the whiteboard, right? And be like, "Here's here's some boxes and here's "Here's here's some boxes and here's "Here's here's some boxes and here's some stuff. Here's the general some stuff. Here's the general some stuff. Here's the general orientation. Here's the servers, orientation. Here's the servers, orientation. Here's the servers, whatever."

whatever." whatever." >> Yeah. You know what? You're going to get >> Yeah. You know what? You're going to get >> Yeah. You know what? You're going to get a kick out of this, too. It will, of a kick out of this, too. It will, of a kick out of this, too. It will, of course, read git history. So, it'll it course, read git history. So, it'll it course, read git history. So, it'll it can look at a file and know like this can look at a file and know like this can look at a file and know like this was introduced by Derek in 2023. And was introduced by Derek in 2023. And was introduced by Derek in 2023. And it'll read the the git, you know, commit it'll read the the git, you know, commit it'll read the the git, you know, commit comments and the surrounding, you know, comments and the surrounding, you know, comments and the surrounding, you know, it'll look up the pull request that it it'll look up the pull request that it it'll look up the pull request that it was attached to and read the surrounding was attached to and read the surrounding was attached to and read the surrounding tickets from around that time. So that tickets from around that time. So that tickets from around that time. So that its ability to gather context is just its ability to gather context is just its ability to gather context is just insane. It'll say like yeah this was insane. It'll say like yeah this was insane. It'll say like yeah this was this was put in in 2023 as part of this this was put in in 2023 as part of this this was put in in 2023 as part of this workstream to optimize workstream to optimize workstream to optimize >> uh this part of the you know slot >> uh this part of the you know slot >> uh this part of the you know slot calculation engine cuz that's always the calculation engine cuz that's always the calculation engine cuz that's always the thing is we'd be like why does this code thing is we'd be like why does this code thing is we'd be like why does this code operate this way and we're like nobody operate this way and we're like nobody operate this way and we're like nobody remembers you know where we'd have to go remembers you know where we'd have to go remembers you know where we'd have to go back through and go through notes or back through and go through notes or back through and go through notes or wipe holy crap that's amazing. wipe holy crap that's amazing. wipe holy crap that's amazing. >> Yeah. Yeah. [laughter] Well, remember >> Yeah. Yeah. [laughter] Well, remember >> Yeah. Yeah. [laughter] Well, remember remember when when you were starting to remember when when you were starting to remember when when you were starting to code drip? I was like so we had a code drip? I was like so we had a code drip? I was like so we had a conversation and I was like um so you're conversation and I was like um so you're conversation and I was like um so you're going to I don't know how we got here going to I don't know how we got here going to I don't know how we got here but it was like you're going to add code but it was like you're going to add code but it was like you're going to add code comment you know comments you used to comment you know comments you used to comment you know comments you used to add comments in code people to like say add comments in code people to like say add comments in code people to like say what it says and you're like I'm not what it says and you're like I'm not what it says and you're like I'm not going to do that because it's rail it's going to do that because it's rail it's going to do that because it's rail it's Ruby and Rails and it's supposed to be Ruby and Rails and it's supposed to be Ruby and Rails and it's supposed to be written so simply that you can read it written so simply that you can read it written so simply that you can read it and that comments go out of date and we and that comments go out of date and we and that comments go out of date and we had this whole conversation I was like had this whole conversation I was like had this whole conversation I was like fine I believe you and with tests it's fine I believe you and with tests it's fine I believe you and with tests it's it's less brittle anyways now that would it's less brittle anyways now that would it's less brittle anyways now that would be laughable to like write comments in be laughable to like write comments in be laughable to like write comments in your code there's no there's just no your code there's no there's just no your code there's no there's just no reason to you know Yeah. Yeah. But it's reason to you know Yeah. Yeah. But it's reason to you know Yeah. Yeah. But it's funny too like even even these days just funny too like even even these days just funny too like even even these days just writing a commit message by hand feels writing a commit message by hand feels writing a commit message by hand feels archaic because it's like these days archaic because it's like these days archaic because it's like these days you're building with an agent generally you're building with an agent generally you're building with an agent generally the agent has so much context and the

the agent has so much context and the the agent has so much context and the agent can summarize so much better what agent can summarize so much better what agent can summarize so much better what we did and why we did it. we did and why we did it. we did and why we did it. >> So it's it's crazy how much better the >> So it's it's crazy how much better the >> So it's it's crazy how much better the commit history has gotten about commit history has gotten about commit history has gotten about capturing context. capturing context. capturing context. >> In a minute, Dererick and I get into how >> In a minute, Dererick and I get into how >> In a minute, Dererick and I get into how to make sure you don't hire the wrong to make sure you don't hire the wrong to make sure you don't hire the wrong person and waste months of time and person and waste months of time and person and waste months of time and runway. But first, hiring your first runway. But first, hiring your first runway. But first, hiring your first developer is a big milestone. It means developer is a big milestone. It means developer is a big milestone. It means you've already cleared the riskiest part you've already cleared the riskiest part you've already cleared the riskiest part of the journey. You found an idea worth of the journey. You found an idea worth of the journey. You found an idea worth building, and you got people to pay for building, and you got people to pay for building, and you got people to pay for it. But if you're not there yet, that it. But if you're not there yet, that it. But if you're not there yet, that early part is exactly what my new book early part is exactly what my new book early part is exactly what my new book is about. It's called [music] Idea to is about. It's called [music] Idea to is about. It's called [music] Idea to Traction. It's a step-by-step guide to Traction. It's a step-by-step guide to Traction. It's a step-by-step guide to finding an idea worth pursuing, finding an idea worth pursuing, finding an idea worth pursuing, validating that people actually want it, validating that people actually want it, validating that people actually want it, and launching something they'll pay for. and launching something they'll pay for. and launching something they'll pay for. Basically, how to stop building SAS Basically, how to stop building SAS Basically, how to stop building SAS nobody wants in the age of AI. nobody wants in the age of AI. nobody wants in the age of AI. Pre-orders open in a few days. They Pre-orders open in a few days. They Pre-orders open in a few days. They might even be open now depending on when might even be open now depending on when might even be open now depending on when you're watching this. Either way, head you're watching this. Either way, head you're watching this. Either way, head to idea toractionbook.com and get on the to idea toractionbook.com and get on the to idea toractionbook.com and get on the wait list. You'll get my 9to5 audit wait list. You'll get my 9to5 audit wait list. You'll get my 9to5 audit right away that walks you through how to right away that walks you through how to right away that walks you through how to find a 10K a month SAS idea at your day find a 10K a month SAS idea at your day find a 10K a month SAS idea at your day job. You'll also get an invite to a live job. You'll also get an invite to a live job. You'll also get an invite to a live Q&A where I'm going to answer your early Q&A where I'm going to answer your early Q&A where I'm going to answer your early stage questions. Plus, you'll get access stage questions. Plus, you'll get access stage questions. Plus, you'll get access to some other bonuses that won't be to some other bonuses that won't be to some other bonuses that won't be available after the book is published.

available after the book is published. available after the book is published. All right, let's get back to Michael's All right, let's get back to Michael's All right, let's get back to Michael's last question about making the last question about making the last question about making the onboarding process as smooth as onboarding process as smooth as onboarding process as smooth as possible. Would you pair program like an possible. Would you pair program like an possible. Would you pair program like an hour or two a day for the first week or hour or two a day for the first week or hour or two a day for the first week or two with like a new a new hire? two with like a new a new hire? two with like a new a new hire? >> Yeah, I've always done that. I feel like >> Yeah, I've always done that. I feel like >> Yeah, I've always done that. I feel like it's um you know, especially early on, it's um you know, especially early on, it's um you know, especially early on, that's your time to really infuse the that's your time to really infuse the that's your time to really infuse the the ethos of like what we do and how we the ethos of like what we do and how we the ethos of like what we do and how we do it. Um and getting some of those do it. Um and getting some of those do it. Um and getting some of those particular patterns that we like to particular patterns that we like to particular patterns that we like to follow when we do things infused into follow when we do things infused into follow when we do things infused into that person is really crucial early on, that person is really crucial early on, that person is really crucial early on, I think. And some of that can come from I think. And some of that can come from I think. And some of that can come from an AI agent reading the codebase and dis an AI agent reading the codebase and dis an AI agent reading the codebase and dis and trying to discern some of that. But and trying to discern some of that. But and trying to discern some of that. But also there's the element of like also there's the element of like also there's the element of like building the rapport, building the building the rapport, building the building the rapport, building the here's how we work together on things, here's how we work together on things, here's how we work together on things, here's how we disagree on things and how here's how we disagree on things and how here's how we disagree on things and how we resolve those disagreements. And so we resolve those disagreements. And so we resolve those disagreements. And so there's a lot of that kind of human there's a lot of that kind of human there's a lot of that kind of human level collaboration value in spending level collaboration value in spending level collaboration value in spending time together pairing. So yeah, I've time together pairing. So yeah, I've time together pairing. So yeah, I've always spent a good couple weeks, you always spent a good couple weeks, you always spent a good couple weeks, you know, kind of each day for an hour or know, kind of each day for an hour or know, kind of each day for an hour or two or whatever. um pair programming two or whatever. um pair programming two or whatever. um pair programming >> and then in terms of not choosing the >> and then in terms of not choosing the >> and then in terms of not choosing the wrong person I mean obviously this is wrong person I mean obviously this is wrong person I mean obviously this is this is the big risk of hiring anybody this is the big risk of hiring anybody this is the big risk of hiring anybody this is tough the things there's a this is tough the things there's a this is tough the things there's a couple things that come to mind like couple things that come to mind like couple things that come to mind like when I'm looking to hire a developer when I'm looking to hire a developer when I'm looking to hire a developer specifically I think we have technical specifically I think we have technical specifically I think we have technical acumen we have interpersonal dynamics acumen we have interpersonal dynamics acumen we have interpersonal dynamics and that includes do we get along the and that includes do we get along the and that includes do we get along the thing we said earlier are they flexible thing we said earlier are they flexible thing we said earlier are they flexible in their thinking you know will they are in their thinking you know will they are in their thinking you know will they are they good team player there's a ton of they good team player there's a ton of they good team player there's a ton of stuff you can wrap up into that one and stuff you can wrap up into that one and stuff you can wrap up into that one and then the third is Like I guess it's just

then the third is Like I guess it's just then the third is Like I guess it's just reliability. This is for any employee. reliability. This is for any employee. reliability. This is for any employee. Like are they do they ship stuff on Like are they do they ship stuff on Like are they do they ship stuff on time? Do they do what they say they're time? Do they do what they say they're time? Do they do what they say they're going to do? And do they show up to work going to do? And do they show up to work going to do? And do they show up to work and do they you know not call in sick and do they you know not call in sick and do they you know not call in sick all the time or whatever, right? There's all the time or whatever, right? There's all the time or whatever, right? There's like this kind of consistency, like this kind of consistency, like this kind of consistency, reliability cuz I've had folks who are reliability cuz I've had folks who are reliability cuz I've had folks who are great technically in different roles great technically in different roles great technically in different roles whether the dev or copyriter, marketer, whether the dev or copyriter, marketer, whether the dev or copyriter, marketer, great technically, great interpersonally great technically, great interpersonally great technically, great interpersonally and they're super flaky. Yeah. Right. So and they're super flaky. Yeah. Right. So and they're super flaky. Yeah. Right. So you need all three of these. So, the you need all three of these. So, the you need all three of these. So, the thing you can't test is the third one, thing you can't test is the third one, thing you can't test is the third one, the flakiness. You just have to work the flakiness. You just have to work the flakiness. You just have to work with someone and whether that's for a with someone and whether that's for a with someone and whether that's for a couple weeks on a probationary period or couple weeks on a probationary period or couple weeks on a probationary period or whatever, aside from asking someone when whatever, aside from asking someone when whatever, aside from asking someone when they're going to tell you the right they're going to tell you the right they're going to tell you the right answer, you know, but the other two you answer, you know, but the other two you answer, you know, but the other two you can test in conversations and in pair can test in conversations and in pair can test in conversations and in pair programming. So, when you and I started programming. So, when you and I started programming. So, when you and I started hiring engineers for drip, remember it hiring engineers for drip, remember it hiring engineers for drip, remember it was go it was a take-home project. Now, was go it was a take-home project. Now, was go it was a take-home project. Now, that is laughable because they will do that is laughable because they will do that is laughable because they will do it with AI, which they should, but like it with AI, which they should, but like it with AI, which they should, but like it's just you're not going to do that. it's just you're not going to do that. it's just you're not going to do that. And so, we but we switched to pair And so, we but we switched to pair And so, we but we switched to pair programming once we really started programming once we really started programming once we really started hiring engineers because we found it was hiring engineers because we found it was hiring engineers because we found it was so much more productive, not just to see so much more productive, not just to see so much more productive, not just to see the results, but to see how they the results, but to see how they the results, but to see how they thought, to see what it's like when they thought, to see what it's like when they thought, to see what it's like when they were challenged. You would challenge were challenged. You would challenge were challenged. You would challenge them. Usually with one thing, you're them. Usually with one thing, you're them. Usually with one thing, you're like, "Oh, I'm a really good throw for a like, "Oh, I'm a really good throw for a like, "Oh, I'm a really good throw for a loop here. I'm going to tell them to use loop here. I'm going to tell them to use loop here. I'm going to tell them to use suddenly use spaces instead of tabs or suddenly use spaces instead of tabs or suddenly use spaces instead of tabs or whatever and see if they like completely whatever and see if they like completely whatever and see if they like completely go you know go postal or whatever. So go you know go postal or whatever. So go you know go postal or whatever. So those are my thoughts like you know we those are my thoughts like you know we those are my thoughts like you know we we would have one or two conversations we would have one or two conversations we would have one or two conversations usually two usually two usually two >> that was after an initial HR screening >> that was after an initial HR screening >> that was after an initial HR screening but then you and I think we have one or but then you and I think we have one or but then you and I think we have one or two then we bring them in for we would

two then we bring them in for we would two then we bring them in for we would bring them in in person because we were bring them in in person because we were bring them in in person because we were hiring in Minneapolis but now you do it hiring in Minneapolis but now you do it hiring in Minneapolis but now you do it remote right with Tupel or something uh remote right with Tupel or something uh remote right with Tupel or something uh for what was it a twoh hour was it for what was it a twoh hour was it for what was it a twoh hour was it usually two hours a pairing I don't usually two hours a pairing I don't usually two hours a pairing I don't remember. Yeah, I think something like remember. Yeah, I think something like remember. Yeah, I think something like that. I ended up going maybe three hours that. I ended up going maybe three hours that. I ended up going maybe three hours on my last one. It went really fast in on my last one. It went really fast in on my last one. It went really fast in my recollection. Like I thought we were my recollection. Like I thought we were my recollection. Like I thought we were going to make so much more progress and going to make so much more progress and going to make so much more progress and it we didn't make a ton of progress on it we didn't make a ton of progress on it we didn't make a ton of progress on what we were doing, but it was still a what we were doing, but it was still a what we were doing, but it was still a high value exercise. You know, high value exercise. You know, high value exercise. You know, >> here's the thing with this. This is >> here's the thing with this. This is >> here's the thing with this. This is someone I'm basically like, yes, they've someone I'm basically like, yes, they've someone I'm basically like, yes, they've said all the right things. They get I said all the right things. They get I said all the right things. They get I like this person. I think they're going like this person. I think they're going like this person. I think they're going to be a good fit for the team. As long to be a good fit for the team. As long to be a good fit for the team. As long as they're a decoder, they're in. You as they're a decoder, they're in. You as they're a decoder, they're in. You know what I mean? This is the last step know what I mean? This is the last step know what I mean? This is the last step for me before we hire someone. So, cuz for me before we hire someone. So, cuz for me before we hire someone. So, cuz you might think two to three hours of you might think two to three hours of you might think two to three hours of pairing, wow, that's a long time. But pairing, wow, that's a long time. But pairing, wow, that's a long time. But most of the time, not all actually, I most of the time, not all actually, I most of the time, not all actually, I remember there was one or two that you remember there was one or two that you remember there was one or two that you paired with and you were just like, paired with and you were just like, paired with and you were just like, "No." And it was great. That saved us a "No." And it was great. That saved us a "No." And it was great. That saved us a ton of time. Um, but most of the time by ton of time. Um, but most of the time by ton of time. Um, but most of the time by the time they got there, you know, we we the time they got there, you know, we we the time they got there, you know, we we did wind up hiring them. did wind up hiring them. did wind up hiring them. >> Yeah. I will say, uh, using a recruiter >> Yeah. I will say, uh, using a recruiter >> Yeah. I will say, uh, using a recruiter was super helpful on this last round of was super helpful on this last round of was super helpful on this last round of hiring. Um just cuz you know you you hiring. Um just cuz you know you you hiring. Um just cuz you know you you ideally you're you're promoting this ideally you're you're promoting this ideally you're you're promoting this widely that you that you're hiring you widely that you that you're hiring you widely that you that you're hiring you know to to get it in front of know to to get it in front of know to to get it in front of >> hopefully a good amount of people so the >> hopefully a good amount of people so the >> hopefully a good amount of people so the right fit can emerge but then you just right fit can emerge but then you just right fit can emerge but then you just have so much uh so many applications to have so much uh so many applications to have so much uh so many applications to wade through so much sifting and and wade through so much sifting and and wade through so much sifting and and initial screening initial screening initial screening >> with AI now AI generating applications >> with AI now AI generating applications >> with AI now AI generating applications and all that.

and all that. and all that. >> Yeah. And I often recommend remote first >> Yeah. And I often recommend remote first >> Yeah. And I often recommend remote first recruiting. It's Dan and Ian's um recruiting. It's Dan and Ian's um recruiting. It's Dan and Ian's um recruiting service for I think it's flat recruiting service for I think it's flat recruiting service for I think it's flat fee and or I know it's flat fee and a fee and or I know it's flat fee and a fee and or I know it's flat fee and a lot of tiny seat companies use that. lot of tiny seat companies use that. lot of tiny seat companies use that. There are other options out there who There are other options out there who There are other options out there who I'm curious who you use. I'm curious who you use. I'm curious who you use. >> I use them. Yep. >> I use them. Yep. >> I use them. Yep. >> Use them. Okay, great. And they were and >> Use them. Okay, great. And they were and >> Use them. Okay, great. And they were and they hire so folks know they hire around they hire so folks know they hire around they hire so folks know they hire around the world. They hire developers. They the world. They hire developers. They the world. They hire developers. They hire like any role at a SAS for sure. hire like any role at a SAS for sure. hire like any role at a SAS for sure. Customer success and sales and stuff and Customer success and sales and stuff and Customer success and sales and stuff and they've helped uh and they hire they've helped uh and they hire they've helped uh and they hire marketers and freelancers and all kinds marketers and freelancers and all kinds marketers and freelancers and all kinds of stuff. So remote first recruiting if of stuff. So remote first recruiting if of stuff. So remote first recruiting if you're interested. Thanks again to Derek you're interested. Thanks again to Derek you're interested. Thanks again to Derek for joining me to help answer Michael's for joining me to help answer Michael's for joining me to help answer Michael's question. If you've got your own question. If you've got your own question. If you've got your own question, head to robwalling.com/quests question, head to robwalling.com/quests question, head to robwalling.com/quests and we'll consider it for an upcoming and we'll consider it for an upcoming and we'll consider it for an upcoming episode. Hiring your first developer episode. Hiring your first developer episode. Hiring your first developer means you've made it further than most means you've made it further than most means you've made it further than most founders. You got real revenue and now founders. You got real revenue and now founders. You got real revenue and now you're building a team. But there's a you're building a team. But there's a you're building a team. But there's a good chance your first hire shouldn't be good chance your first hire shouldn't be good chance your first hire shouldn't be a developer. In this video, I give a a developer. In this video, I give a a developer. In this video, I give a talk that walks through how to think talk that walks through how to think talk that walks through how to think about who your next hire should be and about who your next hire should be and about who your next hire should be and the different directions you can go the different directions you can go the different directions you can go depending on the skill set of the depending on the skill set of the depending on the skill set of the founding team. Go watch that one next.

founding team. Go watch that one next. founding team. Go watch that one next. If you found this video helpful, please If you found this video helpful, please If you found this video helpful, please give it a like and a subscribe. Thanks give it a like and a subscribe. Thanks give it a like and a subscribe. Thanks for watching. I'll see you next time.