Chris Oliver: Building a Life (and Businesses) on Rails

• Build Your Saas Episode: Nobody in SaaS wants to talk about this
• Build Your SaaS Episode: Super Fun SaaS Sales Tax (Part Deux)
• Die With Zero book

• GoRails
• Jumpstart Rails
• Hatchbox Hosting
• The Remote Ruby Podcast
• and many other things you can find at https://excid3.com/

CJ: Welcome to Build and Learn. I'm CJ

Colin: And I'm Colin, and today we are hanging out with Chris Oliver. Welcome Chris.

Chris: Hey, thanks for having me. Good to see you guys.

CJ: You too. I, I think we should probably just run down the list of all the things that Chris works on in case you don't if you haven't already.

Chris: all that?

Colin: Do you have time for all that?

Chris: Yeah. It doesn't feel like it. Some days

CJ: I mean, the, the biggest thing right now is that you've got a baby, right? Which is like taking all of your sleep.

Chris: That's been, it's been wonderful. But yes, it is very, he's been a really good baby though, so like, I feel like he sleeps really well. He eats really well. He doesn't really cry that often unless he's hungry. Or, like yesterday he got his shot, so he was like quite fussy compared to normal. But you know, I think we've been very lucky. He turned seven months old today actually.

CJ: Okay.

Chris: I'm enjoying it, but it, it does take like the routines all change. So like in the morning, get up, feed him, change him, take him to daycare and like that was my prime time for recording videos and stuff. And now that's gone. And then some days I gotta pick him up from school early cuz like, he got his shot, so he had a temperature yesterday and they were like, oh, we gotta send him home just to be safe. And I'm like, Ugh. So now I gotta go take out an hour of my day in the middle of the day to go get him. And then I've, I haven't been home the rest of the day, so it's not like I'm be doing much recording then and stuff. So it's, it's definitely squeeze work in where you can find it now, but at least like I work for myself and I can, I can work weekends or nights or whatever, you know, works out.

Colin: sounds like a little bit of a forced work life balance though. You got

Chris: Yeah, it is.

Colin: gonna happen.

Chris: It is great. It's also been, you know up until February of this year, it was me and Colin, Colin started in January of last year. So 2022 Colin Giber yeah, he, he was the first employee last year and then in February this year ended up hiring Kent and Andrew, and so now we're a team of four, which was like a much easier decision cuz like in the past I was just kind of like, well, there's more support, I'll just like do it and. I had some time and it wasn't a big deal, but now it's like I have way less time, so time to like reinvest the money into the, the business and grow the team and it'll take some time to train them and me to learn to be a manager and whatever. Like I'm, I'm doing a very different job now than I was but still trying to also do that same job I was previously doing with recording videos and maintaining code and projects and stuff. But you know, it's time to spread the load.

CJ: is everyone on the team recording videos? I know Colin did a bunch.

Chris: Yeah. Colin's been doing he's been doing like the entire Ruby for Beginners series on our new learning path. So we're trying to give. Go Rails for the longest time has been like Rails Cast was, which was like, here's the feature and we just kind of jump around to different features and you know, some of them may be a multipart thing that's like four or five videos long, but it was just kind of like, here's a random topic every week. But there was a lot of in, in order to like help beginners more and get more people in the Rails community, we ended up like, let's go build a sort of curriculum. And so we're gonna have like intro prerequisites which will cover like Ruby sql, html, C s s, JavaScript, you know, basics of all those. Then we'll build, like, I'm in the middle of recording our second rail series, which is gonna be building a forum. We built a blog originally and just did like all the little things of like, here's H T D P requests, here's how routes are mapped, and everything in, in rails. The forum is like, Assume you learned a lot of those things. We'll, repetitively do these things so you understand it as you go. But like we will be little less detailed on some of those and like, you know, jump into more complex things as we go. And a forum generally is like a blog, but there are all these other little nuances. Like a blog didn't need associations really, but now the forum needs a topic in forum posts and categories. And, you know, you may want to, like the feature I was building today was like opting in or out of a thread to get notifications. Not one's like, well if you posted. In the thread, you're by de facto like subscribed. But if you're subscribed through that, then you might want to opt out, but you also might not have interacted on that topic. You just want to see any new posts so you can opt in and you know, there's like four different states or whatever you could be there. And so we're, you know, eeking our way into those like more complex topics and stuff, but start out, do all the basics of the forum, then like here's notifications. Turns out they're not as simple as everything we've done so far. So, you know, it'll be a challenge when you get to that part, but that's the point. Like, do the repetitive work, ingrain that in your head and then like do some. Expansion stuff that's a, a challenge or whatever for you. So I've got at least 10 different projects like that on the to-do list to do for like Rails for beginners. And then we're gonna do some other stuff too, like building products and integrating Stripe and, you know, doing more complex stuff and we'll probably have like three or four levels of different content for it. But trying to, you know, give sort of a curriculum and still also on top of that, do our weekly Screencast and maintain Hatch box and maintain jumpstart and all of the open source projects too, and is kind of nuts, but,

CJ: Yeah. That's wild. Have you ever considered, yeah. And having a baby, I mean, it's great that you're growing the team too, cause that'll take a load off. Have you considered teaching or like having a course about building a business? Like I feel like you've kind of figured the business stuff out pretty well too.

Chris: that's a really good one. I haven't thought about doing exactly that, but sort of in that sense like because what I want to do with Jumpstart is like give people more than just code for like starting your business. So that would fit in really nicely there. Cuz I've thought about, like, I've actually written up, I haven't published it yet, but, you know, go use Stripe Atlas and then, you know, go find a lawyer and, you know, Consider an S corporation if you don't want, you know, if you don't want investors, then, you know, just having sort of like this whole detail thing about like, make sure you set up an email list and get people on there and automate the welcome emails and have, you know, an evergreen sort of thing going on there to pitch your product to those people. And then, you know, trying to get into all that. So that would definitely make sense to do like a course with that. So yeah, I'll definitely have to have to think about that and what it might, what it might look like. Yeah, I like it. That would be really fun. Because I would definitely, what I like making is stuff like that where I'm like, I wish I could have bought that 10 years ago when I was starting, if I could've paid 500 bucks or whatever for the, you know, complete course on all of those, like, little decisions you have to make along the way. Even little things that are like here, how do you deal with, with sales tax? You know, do you even need to deal with sales tax? I had no idea, but we can use, you know, Stripe Tax or whatever to figure that out now. Much easier than, I like, read a bunch of crap on Missouri's website about sales tax and was like, well, if it's like they don't charge sales tax for Netflix, go Rails is pretty close to Netflix, so I assume I don't have to charge sales tax in Missouri. And like, they eventually sent me a letter in the, in the mail that was like, you owe us $5,000 or something. And I was like, for what? And then I had to call them and they were like, You know, you explain your situation and they're like, yeah, just send us a note that this is why. You know? Yeah. And they, and they basically just do that as a tactic to scare you and, you know, taking it seriously and stuff. But they like estimate what you probably would owe. And I was like, oh God, I don't like have $5,000. And I was like, and also I'm pretty sure I don't, I'm not supposed to.

Colin: I would pay attention to that cuz states are becoming aware of SaaS. The opportunity of sas and they're starting to come after, even down to the state level. I think it was Chicago that is now doing like a, I don't know if it's, you have to have customers in Chicago or if you're based in Chicago. Transistors running into this because John Buddhas in Chicago. And so part of the transistor team is there. And so Justin Jackson has a whole bunch of episodes on their podcast. Build Your Sass about the trials and tribulations of just trying to, just trying to stay on the right side of the line is so difficult. Yeah. And you don't know what you don't know. And so like having that, that bulleted list of, you know, this is how Jumpstart recommends you run your business would be pretty useful.

Chris: Yeah. And a lot of that too, you can rely on, you know, if you have a good accountant, then they will know somebody who's a good lawyer for tax law and, you know, can refer you to somebody to get advice and whatever. Cuz we had them reach out again, I think it was, and it was like, or no, when, when we launched Jumpstart, my accountant was like, Hey, let's just go talk to a tax lawyer and have him look at your product and like write up whatever document. And it was basically like, you know, this is not taxable in Missouri. And if. There ever comes contention with the state of Missouri than like the tax lawyers. It's, it's on his shoulders. So you're basically paying him like a thousand dollars for insurance to protect you in case something does happen. So it's like, if he made a mistake then okay, then he will deal with it. But we. You know, just paid, we paid a thousand dollars for a document for no reason, unless something becomes a problem in the future, which it shouldn't, but it better safe than sorry. And, you know, you're on the, the right side of things there. But yeah, it's a pain. When Colin Gilber join, he's in Louisiana. So Louisiana has different laws and so we have to collect sales tax for just Louisiana customers, for just some products. Because not all digital sales in Louisiana are the same. So a platform is a service like Hatch Box. Not sales taxable, but like Jumpstart is to Louisiana customers. And then also he lives in a, not a county, but a parish in Louisiana. They have their own sales tax there. So you gotta do it on the state level and the county level or the parish level. And some states, like you mentioned, Colin, that are like where you're selling to, not where your company is based, they want to collect sales tax too. So technically there's a lot that. Even like having one sale in the UK or in Europe or whatever, can like put you over the threshold. And so you're supposed to do that and it just is making it awful for like entrepreneurs because you're gonna have to have just like a, you have to use something to help you because there's no way you can like do all that work because you're trying to make the business and make a salary period. But it's like, oh, great, now you have all this overhead to even begin before you can make your first dollar. You'll have to like figure out all that. It's just, it's I don't know, barriers to entry that are not great. Doesn't really encourage people to create their own companies or anything. It's not good,

Colin: It sounds like a good business opportunity for somebody out there if anyone's listening and wants to pull up their sleeves and get into tax. You know, I mean, a new government would be useful. I mean, we, we are like 50 unique countries, right? As the United States. It's like we, CJ and I ran into this when we were doing e-commerce with, I mean, it's a physical product, but it was a subscription. And are you in Nexus or are you not? And do you use, which vendor do you use? This was pre-trip text too, so it was like, you know, which other a p I do we have to pay for? And I think Justin concluded there wasn't really a good bulletproof service for this yet. So it's an opportunity out there for somebody.

Chris: Yeah, yeah. Stripe Tax was probably the easiest piece for me cuz I went in and created the products and then like read through all of the options for what tax category it was. And then I found ones that were like, platform is a service. That's pretty much what Hatch Box is. Just select that and then like, okay, now I know in the previews it would show like zero tax from Missouri, whatever for Louisiana. And you know, any other future states we have added, it'll show that. And I would just kind of know where before I was like trying to read the Louisiana, you know, law rulings and whatever for stuff. And it's like, good luck, you'll, you will never find what you want. Or you might find what you want but you can't understand it because it's written in some obscure language, legal ease.

CJ: Yeah. Need some chat. G P T to translate it into simple whatever. I, I remember when I was working outta the collective Colin, a Anne, like, sat down with me and like helped sh you guys have like a bunch of cheat sheets and stuff for getting hooked up in Nevada. That was pretty cool. I don't know if that's still like a, a thing that you offer at the collective.

Colin: it, it's something we should do more of for sure. It, it's one of those things where, I mean, I didn't expect that we were gonna, this is, this is the tax episode for everybody who is just joining us. But even with the co-working space, we're a weird one where like every time we had to switch accountants for filing our taxes and they were like, you guys are passed through income. And I was like, if you change our. Our income to pass through. Like it affects us in such a weird way and we're not passed through income. Like a co-working space is not someone buying property and then renting it out to somebody. We, it's like a whole service on top of the space. And there's obviously like, Probably a spectrum of co-working spaces where some of them just rent to somebody and call it a day. But like, we have a team, we have a whole bunch of services and things that we offer, including like what you were just talking about. So, you know, I was like, this is how we should be classifying our, our revenue. And the, the accountant wanted to fight me about it, and it's like, we've been in business for 13 years. We are not doing this every year that we have to file our taxes. We did this then. And you know, even the city was like, we don't really understand what you do here. And it's like, okay, let's, let's make business a little bit easier for everybody. I, I know every new Secretary of States, like, we're gonna make government better for business, so let's, let's actually do that. Please. Like better websites, better like, let's get an a p i for all the State Secretary of State websites. Like that's, that would be, you know, in 2023, you'd expect that

Chris: It'd be written in like soap though.

Colin: it would be, yeah. Like can we just get a web hook? Can we get.

CJ: Yeah. I think like co-working spaces are pretty, pretty new, like and also a lot of the companies that are being created with tools like Jumpstart are kind of like, a lot of people have new ideas and so sometimes they don't fit nicely into these tax rules, whatever. And I heard this quote on a podcast recently and I thought it was really funny and it's that. We have paleolithic emotions, medieval institutions, and God-like technology. And I just think about this all the time with like these politicians who are these old, you know, crusty people who lived in a completely different era than we are right now. And like, just the thought of them trying to regulate something like AI or regulate something like, like

Chris: Yeah. Like that interview with the TikTok ceo, that was like, the guy was asking about like, do you have access to my home network? And he was like, well, duh. Like it run, like if you're at home. And you have, how do you think you get internet at home? Like it's on your home network. That's what that is. And it's just like, yeah, how, how could they possibly, well, and you read some of those, some of those tax categories are hilarious cuz it's like this one really obscure little one-off thing and you're like, why is their sales tax for like chocolate chip cookies in this one location or whatever. It's like some weird thing that happened and, and then there's like just these very vague like electronic service and you're like, well, I don't know, maybe that's it. But yeah, it's a, it's a mess. Everybody in governments like super old, don't really know technology. We don't even know a lot of the stuff that's going on as people. It, like, we do one thing, but it's not like, you know, all the stuff that's going on in tech, there's just too much. So

CJ: Our, yeah. And our kids are gonna have to grow up in like a completely different, they're, they're already growing up in a completely different world. I'm looking over my monitor at my son, who is building a Google sheet of components for his own, like custom PC build. And he's using Bing, g p t, like, to confirm the, like compatibility of different components. So as an eight year old, he's able to like copy and paste from e-commerce websites to tell like, is this a TX board compatible with this power supply compatible with this like ram? And so like this is, this is like a thousand times in the future or like, you know, a thousand steps in the future from where I was when, when I was eight. So like, this is, it's it's moving at a pace that's just like yeah. I, I don't know how government is gonna keep

Colin: we're just gonna have to, we're gonna have to get into politics, guys. We're gonna have to,

CJ: Yeah, I mean, I, I almost wonder like if I'm already outta date, you know, like there's, there's a few things where I'm like, okay, I, I feel like I missed some stuff with that whole crypto wave. And there's definitely some details in there where I would not have an informed opinion about how to regulate it well, and so like even I, as you know, I'm in my thirties, like I already feel uncomfortable about making policy around those, like, new things. And so, yeah. I don't even know.

Colin: I think that's a, that's a good baby step from eighties though, like eighties to thirties

CJ: True.

Colin: you, and you have this learning mindset. I think that's the difference. It's like we, we learn these tools, we play with them, we. There needs to be a way to, to, to think about those kinds of things. I really like, like the 18 F, which is the digital service as an option. They are not big enough to deal with all the government tech problems that exist. Like I think they've started with just making the websites accessible. Right. Which is a big. Pain into itself. But here in Nevada, they're like, they spent a lot of money on this new, like all-in-one business platform thing. And it is garbage. And I will publicly say that any day they are now talking about doing an R R F P for redoing it. And I'm like, how much money is allocated for this? And either a, can I bid on it

Chris: Yeah.

Colin: I, like, I have a whole bunch of accountants and bookkeepers and businesses that we've seen the problems. We know what needs to be fixed. Or like, are you gonna have a transparent process for picking the next person? Because it's like, is it just to rebuild the current one? Is it to refactor it? Is it to start new? Because we all know what happens when you try to do a full rewrite. Like we're gonna lose a lot of the context that happened in the first one, and no one's gonna know why the thing exists. And they're like, oh, why does this thing do this? It's like, oh yeah. Some random weird rule in some county somewhere.

Chris: Yep. Yeah, there's, have you guys watched that movie war Dogs or whatever, where it was like, where like they have the, the government contracts that they're like, we just need to buy like a thousand Berettas from anybody, and like anybody could submit a proposal and they start like selling random stuff and whatever to the government and making tons of money. It's, you'll have to

Colin: I'm gonna have to watch

Chris: you can be the next war dog.

CJ: Yeah, it's pretty funny. They've also, there's like a, there's a book too that they one of them wrote I have a buddy that, that works for a government contractor, and we used to talk about this all the time. Like, we should just submit for government contracts to like, make screws or

Colin: give more governments on rails, right?

CJ: Yeah. I mean, I'm sure there's tons and tons of

Colin: jumpstart, government,

Chris: you

CJ: Yeah. Solving all the, all the world's needs here.

Colin: just a little bit of device and you know, a little bit of

CJ: when you, when you deploy with Hatch Box, like have you run into anything where people have to be like HIPAA compliant or have like any like crazy compliance

Chris: People have asked and it's pretty much like, we're not gonna be HIPAA compliant. I'm pretty sure like, it's such a vague set of rules too. It's like hard to know that you're really compliant. So you probably need to go through some company that can certify that you're actually HIPAA compliant and stuff. And it was like, I'm one person you know, I don't need to do this for a one-off customer, unfortunately. And like a Heroku, I, I looked into it at one point cuz a couple customers had reached out about that. And I was like, looking at Heroku's. Version is like, starts at $2,000 a month. And I was like, oh, that's that's tempting. But it kind of brings you back to like the points that like Basecamp has made where they're like, we don't wanna make a oversized amount of money from one or two customers. Cuz if they ever leave us and like our business goes out the window, like we lose half our business or more. And then what do we do? And we gotta fire all these people or whatever. Like we're we're un like diversified. So that was kind of the same thing where I was like, you know what, we could end up with a few customers that are paying us, you know, most of our customers are pretty small, under a hundred dollars a month. And then you come in with a couple that are like 2, 3, 4, $5,000 a month. And then if they disappear it's like, oh, that's a lot of customers to replace them.

Colin: Or they start throwing their weight around,

Chris: yeah.

Colin: Like they have other requests that you have to do cuz they're paying you more money.

Chris: And then it's basically you're a consultant company for these two, three big customers and you're not really running your own ship anymore. You're just getting dragged behind their boat. And it's like you're not really independent anymore running your own company.

CJ: Mm-hmm.

Chris: that's pretty much where I left it. It was like, yeah, you guys are better served at Heroku or whatever, like, we're not gonna provide that much better of a service or whatever. But yeah, somebody was trying to use AWS gov cloud and other things and like, cool, but you know, it's, it's just not worth it. So I'd rather and I like helping the, the small like Jason Fried and DH h just post like tweets and blog posts about like helping the underdogs. And I really like, I like that a lot. I want to help the, that's why Hatch Box and Jumpstart and Go Rails all exist like. And rails, I feel like is why I'm, I like Rails and Laravel and things like that because it does help the underdog succeed. And it can be one or two people building cool stuff. And like, you know, even if they don't build a company that can employ 50 people, who cares if they ever like having a wonderful living by themselves or with a small team, they win. Like, that's amazing. That can be life changing. So, you know, they're the underdogs and I really enjoy that sort of, that sort of stuff.

CJ: Totally. Yeah. I think that that was one of my favorite parts of my job at Stripe was just helping people earn their first, like money online is, I think that was, it was so, so powerful.

Chris: this is the best feeling in the world. Like, I, I tell the story regularly, but like, I with a friend built this little not so. Not so like compliant with the Apple terms of service, but he was like buying these templates for iOS apps for like a Flappy Bird clone. And then he changed the graphics and make it like Flappy Panda or something stupid thing and like put his add network IDs in there. And then the only way he could actually make money was like finding people to review his game. So it got rated in the app store enough to like get some downloads and get some people playing it and get, you know, ad views. And so he had these Facebook groups who were, people were sharing their apps with each other and reviewing them. So we like built this little rails app. And you would pay $5 for every app you wanted to put in the pool and then you would review other people's, and yours would get. Pushed up the queue, so then other people would review yours first and then you get this little review group going and we made like 30 grand on that, but before it kind of got shut down by Apple and stuff. But it was like the first time we made like $25 and I think you, we had just used PayPal for it back in the day, cuz this is a pretty long time ago, but I was going to the movies, I sit down and it's like, turn your phone off. And I like opened my phone and I see a notification that I just made $25 and I was like, wait a minute. I didn't do any work. And I'm the movie's free. Like what? This is nuts. And like I was, you know, always trading time for money until that point. And then I was like, oh my God, like I'm sleeping and I woke up and I made a hundred dollars. Like, what is this? This is insane. So that, yeah, I, that feeling is wild. If you've never experienced that before and you like wake up and made money, it is insane. And that's, I want as many people to like experience that as possible. Cuz it, it starts to really just like change your, per your perspective or you're not, You're not trying to do things trading your time anymore, which has like a natural limit. You can only work so many hours a week and you're only gonna ever be able to charge so many dollars per hour. Like as a developer, you might get lucky and be able to charge two 50 an hour or something crazy. But you can still only work 40 hours a week. So like you're limited there. But if you're doing something like our Screencast at Go Rails, like I can make one video, 10,000 people could watch it and pay 19 bucks a month for it and like, I only had to do it one time. But that same value was able to be like reused for everybody. So it just like starts to. Open your eyes to those, like those business ideas that are scalable like that or whatever. And then, then you start to realize like, that's where people really make a lot. They like figure out something like that that can be done without trading time for it.

Colin: I have a follow up on that that I'm curious about because I'm like having previously been a consultant, like you become habituated to trading time for money, and I know people who start to think about their time as money. And so now that you've kind of disconnected your time from your money, like do you ever find yourself like thinking about like how much like, oh, I just spent eight hours on this and I could have been made. Like, have you been able to separate yourself from that?

Chris: So now, we built our house and we have a lawn now that I have to mow that takes a lot longer and we have a pool that needs maintenance every week cuz we got trees around and it's like random leaves and other crap and frogs and I found a turtle in our pool and whatever, and it's like, okay, if I was doing all of that, I'd have to spend four hours on every weekend mowing the lawn. I'd have to b be spending at least that during the week, like cleaning the pool and whatever else. So like I've started very much now being like, all right, I can pay somebody to do that, get that time back and I can. I can choose to spend that time trying to make more stuff, or I can like spend that time with my son or whatever and like, choose that. That's like a, I'm gonna pay the money so I get time to spend with the family instead of like, okay, it's worth this much money and I could go back and like record another course in that eight hours I save every week and like in the three months maybe, you know, publish a new course or whatever. Sometimes I think about it that way. It does help me rationalize, like spending more money on things. But you also like, at a certain point probably make enough money that you can do that. And so it's like, it's, it's one of those benefits where it's like if you, once you get to that size, you're like actually now. I'm making enough money, I could just shovel it into savings or whatever. But why don't, my parents were always really bad about this, like saving money and not actually spending it to enjoy their life in the moment. They're always just saving it. And then like my dad had colon cancer years ago, and it was like all of a sudden he almost died. He's recovered and he's fine now, but like he almost died and they're like, Holy crap, life is short. We actually need to, like, we've been talking about traveling, like we've been, never been to New York City. Like we should go do that. It's not that expensive. Like, why didn't we never do, why didn't we never make the time to do that? So they like are doing those things now and like it was great for me to see that when I was younger and be like, yeah, what the hell? Like, I'm 25, my dad almost died. I don't want to like be 50 and then regret that I didn't do those things. So, you know, like I'm just trying to spend as much time as I can with my son when he's little and I don't want to be the dad that's like always working and whatever. So yeah, it's, it's, you know, a tool. That's how I try to think about it now is like the money's a tool. Allocate it where you want. You're in a here in tech, so chances are you'll never really have a trouble finding another job in like worst case scenarios. So it's not like you have to shovel everything into retirement and be scared about it. But you know, you should still do some of that, but you should also enjoy your life in the moment too. But what are you gonna say, cj?

CJ: Oh, well the first thing I was gonna say is like, soon enough, your son, you could just make him mow the lawn and clean the pool. But also like, it's like, yeah, I mean, that's gonna be a few years, right? Yeah. The other thing before I forget is I want to, to recommend the Die With Zero book. It's so good. And like, the whole point of the book is basically like, try to Yeah. Like squeeze every ounce out of your financial life as possible so that you don't end up like, with a bunch of money in the bank dead and like not have any experiences or whatever. Obviously you gotta like, have a balance, but,

Chris: Yeah, you, you need to be able to retire at some point, so you need some retirement money and it's good to plan for that. But it's also like you might not make it to retirement. And then what was the point of having 5 million in the bank by the time you're 78 and you can't use any of that cuz you're stuck at home or something. It's

Colin: And you didn't experience any of those things that you wanted to do, Right, You're like, oh, only when all this stuff is super perfect, I'll go take that vacation and

Chris: Yeah. Yeah. My grandparents did that and they went to like Russia and stuff, but as they were after they were retired, so it was like they couldn't really walk very far. And you know, just, and my grandpa was a farmer so he was like beat up from doing all the stuff outside in the farm for years and years and years. And my dad's kind of the same way. He's got a bum knee and whatever from doing all that too. And I'm like, you know what? It makes it. Virtually impossible for you guys to like go explore cities now without like, you know, riding in a car to go around a lot. And I'm like, I want to go wander around. I had the most fun wandering around like New York City and just any place. So it's like, do it now while you can

CJ: Mm-hmm.

Chris: your kids on those experiences, cuz that will really like open their eyes to things.

CJ: It totally changes your perspective too about when you think about how, oh, in the future things are gonna probably cost way more money. Right? And so you think, oh, maybe like over time my expenses are gonna increase. But the counterintuitive reality is that as you get older, you can't actually spend the money as easily because, because of these physical limitations that your body has as it's breaking down. And so like when you are in your fifties, you'll be able to spend a lot of money, and then you'll be able to spend less in your sixties, even less in seventies. In like, like even less in your

Chris: Your healthcare expenses through the roof, though,

CJ: True, that's true. Yeah. But like, yeah, if

Chris: at least here in the

CJ: fixed income Yeah. Stuck in, stuck at home or whatever, and you're not actually going, going anywhere, like,

Chris: Yeah. Yeah, it's it's one of those things that I was like always. Every time I had a job with a salary, I was working on the side to like, just go build something because I knew like the only real career for the most part that's uncapped is like sales where you get basically free reign to make as much money as you want, as long as you bring in the business and whatever. Then you get paid the commissions and stuff and you, you have no real cap. You, you have sort of a minimum, but it's kind of like being a, you know, a bartender or waiter and it's like you get this like really, really low salary or minimum wage and then you, you're free to be as charming and you know, as good as you want at the job and you can make as much as you want. And that doesn't really generally exist in a lot of software developer careers. You got a salary and, you know, they, they can't tie your work directly to revenue that comes in like they can with the salesperson. So it was always like interesting to me to like, At least do consulting instead because then I could choose to work my butt off and do quarter million a year or half a million a year or something crazy. Cause it was entirely up to how much time do I put in, how good can I be at sales and actually get the work done and everything. And you know, sky's the limit, but at a certain point you're like, well, I can only do so much as one person. And like in the past couple years with Go Rails, like I've been on my own for what, seven, eight years when Colin joined and it was, it, it was coming to the point of like, I'm burning myself out trying to do all this work myself, but I've kind of hit my natural limit of, and I had a chip on my shoulder just to figure out like, how far can I get by myself? And it was like, Crazy numbers, you know, per year, but with one person. And I was like, this is sweet, but this is also unsustainable. Like this is great. But then you get to a point of now your decision is, do I shut things down and stop and cut things out and get my life back, or do I change what I do and hire a team and we continue building stuff. And you have to think too, like, I've been doing this for eight years. Do I want to do this for another eight years or 20 years or whatever? And I'm not really bored of building stuff and rails and, you know, helping the community and whatever. So. The, the appeal was more to like, well, I guess if we have a team, then we can do more stuff and we can accomplish more things and contribute even more. But if I, like, am just myself, I gotta shut things down and like simplify and like, just focus on the, maybe the stuff with the best roi, which maybe isn't the thing that helps the community the most. And so it was kind of like conflicting itself if I was to go that route. So I ended up like, all right, my job's gonna change, becoming more of a manager and you know, a leader in the company. But also it might make the business more like sellable in the future where it was a hundred percent dependent on me. I now have really an asset that I could sell, that someone could take over. They could hire teachers and record stuff and keep doing the Go Rail screencast and like, this is now a business that's not just. Me that isn't really valuable for anybody else unless they hire me as an employee, which would not work because why would I want to do the same thing for somebody else if I'm already doing it for, for myself, just fine. So that was, there was a lot of different decisions there in the last couple years that made it, having a kid makes it very obvious, like, which path you want to take? Because I just kicked the can down the road for like five years just thinking about like, what do I do? I don't know nothing. There was not enough pros or cons for one way or the other. I'm just stuck in a limbo of like, comfortableness where things aren't so bad, you have to shut it down. Things aren't so good that you're like, I am going to just throw everything at this. I'm just like, ah, just keep chugging along. It's, it's going fine. Keeps growing and you're like in a weird spot there where it's like things are. Decent. Pretty good, but they're not like blowing up out of control where I have tons of money and have to go hire people and grow the business. But I al it also doesn't suck. And it's not a point where you're like, why am I doing this? Let's just shut it down and do something else. So that took a long time, but I think it, it eventually got to the point where it was like, it makes plenty of money and I need some, some quiet times. Some like just, you know, share the burden with somebody else. You know, and, and so that's what. I ended up doing in the past couple years, and it's been great. It's just now like we doubled the company from two to four in February and that's that's a big move, a very big move. And what went from, like, most of our meetings in the past were basically like this where we just hop on two pool and chat for whatever, like 15 minutes or an hour or the whole day about anything. And we always knew what everybody was doing. And now it's four people and it's like, well, you're working on this, I haven't talked to you for like three days. And like, it is a totally different experience now with, with four people. So I'm learning all of that and trying to be, you know, cognizant about what do I need to get better at and how do we become a well-oiled machine? And just now you got more personalities and you know, people with different. Responsibilities and other time zones and all these different things to figure out how do we all work together well and efficiently and make sure that everybody has their own space to just go do work without, you know, like I need a lot of quiet time to just poke around at a problem and explore it. And it may not turn out to be anything, but you know, I gotta go just mindlessly think through something by myself without interruptions. And that is like a lot more rare now. So it's interesting to like see that and maybe over time I'm not contributing code as much or something. Or like D HH is kind of like, At least in Rails as an example, he like shows up, does a whole bunch of stuff, and then disappears for like a year or something and does that again and kind of like, you know, does it when it makes sense and whatever. So I don't know if I'll end up in that situation or whatever, but it's, it's interesting to, to go through this change and actually like, have to grow things. But I want to keep it slow and, you know, steady, but, It's it's good. I think it's gonna be very good in the long run, but also it's one of those two where if you make mistakes, you make mistakes and you can like reset. It's okay. Like if you hired people like Adam Wathan did that for tailwind and like realized it wasn't working. He hated it. And, you know, pulled the plug and shrunk the company back down and, and was like I have to, like, it's my company, it's my life. I can make it whatever I want. So if I'm not happy, like I need to go fix it and just not deal with it. Like, this is, this is my life, so I wanna make sure I'm enjoying it.

Colin: We've all had startup experiences where, if you have investors, you don't necessarily always get to go slow and steady like you're talking about and seeing what Adam's doing, seeing what you're doing. Like, I mean we got to hang out at Rails Conf. It was fun to see people react to seeing Go Rails, like you know, the whole four four of you, it's like you have a bigger footprint now and honestly there's some resiliency there too, right? Like if you were sick, go Rails still has three people who can work on stuff. It's not just a thing you can sell, it's a thing that, you know, doesn't need to have Chris show up every single day in order for it to exist.

Chris: I mean that was, that was just before Rails Comp. When I went on vacation for nine days. I didn't touch the computer for nine days. Like, that was the first time in probably nine years that, that I had that long of a stint without working. It was crazy. And now, yeah, I got my bodyguards at Rails Comp and whatever, so,

CJ: Is there, like I assume there's, there's like a back channel that you have with all these other business owners. Do you have like a, a chat thread going with a bunch of ballers that are like, oh, what are you doing, you know, with your marketing this month, or

Chris: a few people, but it's not really like, and, and I probably need to make it something more formal like that, like a mastermind or something where we either just have a discord and we just use that, or I don't know. We've tried, I've tried a few masterminds or it's like a weekly meeting or even biweekly and it's like, I don't know, we're a small business. A lot doesn't happen in two weeks. Like nothing major changes that often, so you really, yeah, it's, it's kind of tough too, cuz some of the, the learnings you get from, if somebody's got a company. That's, say 10 times where you are, if you're like building an agency, what you really, you need to be really in with the person who's like 10 times ahead of you so you can see like, oh, we're doing these things and that really doesn't make sense. But oftentimes, like they're not gonna get any benefit from talking to you. So it can be interesting to try and find the right balance. Where as long as you can provide something in return value wise those really work out well because you can pick up a lot of things. It can be not as useful if everybody's kind of on the same level and it's like, we're all here. We're not sure how we get to there, but here's what I tried. And they can still be useful definitely. But I feel like it's just kind of more like you really want to see the person who's like two steps ahead of you, but it's maybe harder for you to like, Provide anything in return. Cuz they're like, yeah, you're, you're behind me. I need the, I need the guy 10 steps ahead of me.

CJ: Mm-hmm. Sometimes it's energy, though, just like being pumped and like being excited and talking about new, shiny things, and I mean, I think that's probably valuable for those, the folks that are ahead.

Chris: yeah. That is definitely a lot of fun. Yeah. So, yeah, I, I like that for sure. And it's, it's a way to, sometimes you just don't have anybody who's Understands the problems that you have. Like, okay, if you're worried about paying salaries, like you can't talk to employees about that, like you need to talk to another business owner or whatever that understands like, oh God, yeah, we had this issue and like we ended up opening a line of credit with the bank to like smooth things out over time. And it's like, oh, I never even would've thought that I could do that or whatever, and that makes a lot of sense. I'll go do that and try that. And so sometimes, yeah, there's really helpful things and just the energy of like, you have peers to, you know, vent to, or whatever it is, be excited with and stuff. In general, like the education space is just like rough. So I feel like that's not everybody I end up talking to in that, that's doing something similar. It's like, yeah, this just sucks. Have you listened to the hackers Incorporated that Adam Wathan and Ben Orenstein are doing, they're, they nail a lot of those. Like it feels like they're talking to me when I'm listening to that cuz I'm like, everything Adam struggles with basically doing an education business even though it's like a open source CSS thing. It's very similar to what we do in all the struggles we've had. Cuz the thing that made Go Rails like unsustainable for the longest time was like, oh, I want, people are asking me to do these videos for these topics. So I try and cater to those and like, I don't have any interest in doing like a, a backbone js and rails api, whatever. But people were asking for it and I was like trying to accommodate everybody and like I'd burn myself out cause I gotta go teach myself backbone and learn all the ins and outs and then in 40 hours still may not really understand it very well to the point where I can teach it. Or I might end up teaching it in a way that's just like really janky cuz that's how I learned it from these other tutorials. And then people are asking you questions about how, how am I supposed to fix this thing? And you're like, I. I don't know, like I just learned it last week, you know, as much as I do. So I have tried to pivot and just like build stuff and then teach what I'm building and like that, I'm usually very excited about those things and then I can also much more easily teach that content cuz it's fresh in my mind as opposed to like trying to learn something brand new and teach something I don't fully understand. It's much easier if you already know something deeply and go teach it that way. So that's made it, that's made the whole business like sustainable. But it sustainable is relative to, because it's still publish a video every week and it's, you know, the, the, yeah, the grind of same, same thing that all the Twitch Streamers are stuck with. You gotta show up every night, play video games for 10 hours straight and never miss a day and like, That becomes a job real fast, even though you're playing video games, it's a job.

CJ: Yeah, I burnt out real hard, just like making tons of content last year and like, yeah, I like couldn't do it anymore

Chris: and, and you had to, like, you had to do that of using JavaScript frameworks and P h P and Ruby and like you were doing something that seems to me like is extremely hard cuz you, you have to go so broad, whereas in Rails, I can go real deep on Rails and only care about Ruby and Rails things, but you're like, you're deep on stripe, but broad on every language, which is like crazy to me. That sounds very, very hard.

CJ: Yeah, it was, it was tons of fun to learn, like the frameworks and stuff. And in the beginning I had a blast just like picking up all the, like the same patterns in different languages. But yeah, to your point, I would make a video in Ruby having fun with something, and someone would be like, can you do the same thing in php? Now? I'm like, oh my gosh. Like, like, I don't know.

Colin: We need some some elixir. We need some rust.

CJ: Yeah. Yeah. Same. Same Yeah. All right, well as always, you can head over to Build and learn.dev to check out all the links and resources in the show notes.

Colin: Bye friends.