Scott Hanselman: But that’s going to make my little side hustle more helpful, if I don’t have to do the show notes… Or at least they give me draft show notes that I can then zhuzh up a little bit.

Jerod Santo: I just want to code

Zach Bellay’s life-long enjoyment of both a) computers, and b) hustle culture, has cultivated in him the classic angel and devil on the shoulder.

I constantly find the devil on my shoulder trying to convince me to start a new side hustle. Starting a new monetizable side project is like a latent addiction. Giving in feels like relapsing. The angel says don’t worry about some side hustle, just do well in your day job and code for fun as a hobby. But the devil keeps telling me that you can “be your own boss” and “earn what you’re worth”.

Zach has decided (when this was written in 2023) that he must manage the devil, not vanquish it, because the bills will never stop coming. But he’s also learned:

that I can no longer force myself to work on things that I don’t like forever, since I will burn out. As I mature, I am better honing perception for when and when not to give in to the devil’s call to build something for profit.

Suz Hinton: And a pretty depressing example of that too is if you’re in forensics, there are a lot of really nasty stuff that you can have to sift through in forensics. It’s the same as content moderation. You’re seeing similar things. And so I’m really interested in forensics, but I don’t think that I – again, if I can’t watch Mr. Robot, if I can’t watch scary movies, there’s no way that I can work in forensics without feeling psychological damage from that, and it affecting my mental health. So cybersecurity has a lot of mental health problems, just because of the nature of how things have really messed up… And I think that it’s a tech community too, so it has its own sort of toxic parts, which we’re all familiar with in coding communities as well. Yeah, I think that tech has a lot of immaturities that still haven’t resolved as well as they could, and I see very similar patterns in cybersecurity, to be honest.

So it does come with a warning, but I think given that cybersecurity is such a broad field, there are a lot of things you can do that can either keep you out of trouble, or can find your niche without really being exposed to some of the darker parts of cybersecurity. But I think that’s a really good point that you bring up. It’s not all sunshine and rainbows, that’s for sure, and you can ruin your hobby if you’re not careful. I think that if I did pentesting as a hobby, it would be way more fun than doing it professionally. Such as like bug bounty, right? Like, you can make quite a bit of money from bug bounty; if you find a particularly bad vulnerability, you can have a $10,000 payout. And so I know a lot of people chase that as a bit of a game or a side hustle, and that can be really satisfying.

Gerhard Lazu: So I really love the emails. It’s one of the few newsletters which I read. Whenever you send the newsletter, Jerod, I really enjoy it. I have clicked on the View in Browser button, and I noticed – I think until about 90, like issue 90, it had previous design. That was [unintelligible 00:18:58.29] side hustle expose. That was the last issue, which had the new design. And then, 91, it was the new one. So all you have to do is literally drop the email part, and you’ll see the previous design. So news/94, /89, so on and so forth.

Adam Stacoviak: Obsidian version one, that stays there, versus version two that adds the AI, or adds the bells and whistles. Because I think the challenge is that these things - they start out simple, and that’s probably why you have the passion for Typist, is you want to keep it simple, and you also want to satiate that engineering side of your brain to kind of like tinker and have fun and have those boundaries on a side thing; not even a side hustle, just a side thing, just something you do for yourself. And then at some point it just turns into something else, and it’s not the original thing anymore. But my experience is very similar to Jerod’s, is like Command+N for New, obviously, Command+O to find things… I put everything in there; literally, everything that I can ever think of goes into Obsidian because of how fast it is and how simply it’s just driven on type, whether it’s docs, code, anything. Not like literally code, but code blocks, and stuff like that… Just sort of like mostly Linux stuff, like “How do I set up a new Ubuntu machine?” or “How do I do this or that?” I document my own processes and refer to those documents for various things.

So that’s a lot of how I use Obsidian personally… But it’s been very, very, very, very organizing, whereas it’s been disparate; things have been in iA Writer, or at one point Dropbox Paper, or just various places that were not fast. And obsidian is just fast.

Saron Yitbarek: It’s really pricey. And back then there were no payment plans, there were no loans… You had the money or you didn’t. And even I didn’t have the money; I had to borrow some of the money from my mom to help me pay for that program. And so I felt like if you didn’t have a bootcamp, it was really hard to find that support system that to me was so crucial to me learning how to code. And I wanted to create a community for people who were learning, and so I started doing these Twitter chats; this was back when Twitter chats were all the rage, everyone had one… And you’d pick the hashtag, or hashtag was codenewbie, and I would tweet out questions every Wednesday night at 9pm Eastern Time, and I would ask “What are you excited about? What are you learning? What are you stuck on?” and people would respond, and kind of talk to me, and really talk with each other and get to know each other. And there’d be a lot of just this love in these Twitter chats, and this support, and just really good vibes all around.

And I did that week after week, and after about six months of doing that, I said “I think we have something here, but I really want to dig deeper into the stories. I really want to focus in on these developers and inspire people in a deeper way.” And I thought “Podcast. Audio. That’s the right way to do it. That’s a great medium for that.” And so we launched The Code Newbie Podcast. And I think it was maybe two months into doing the podcast, that I got an email from a company who said “Hey, I’ll give you 200 bucks if you run an ad on your show”, and I was like “Whoa, I can make money from this?!” So that was really the first time I started thinking of it not just as this fun side hustle I was doing while I was a developer full-time, but actually had the potential to be a sustainable business.

[08:04] So that launched just – my thinking shifted from that, from “How do I make this into a media company?” It’s kind of funny, because I guess content creator was the right term, but I never thought of myself as a content creator, because my content was never centered around me. It was never about me being in front of the video camera, or me talking about my opinions. I wasn’t trying to be a thought leader. It was really about shining a light on other people and bringing people together. So I thought of myself as more of a community/media company than a content creator.

And so we did the podcast, and then over the years launched another podcast called The BaseCS Podcast, which was me and a good friend of mine, Vaidehi Joshi, who did this series on computer science, and we basically turned her blog posts into an audio format, into a podcast. And that went really well, that got really popular. We launched a conference called Codeland that we do every year, we had meetup groups all over the US… And so just trying to listen to the community and figure out what’s needed and what people wanted support on, and trying to turn those into some type of content, some type of product to help people has been kind of the name of the game.

And so I ran that for three years part-time while I worked as a developer, and then three years full-time, and then I sold it a couple years ago to Dev.to, which was renamed Forum, is the official company name… But they run the Dev.to platform. And after I sold that, I thought “I think I want to stay on the business side of things. Let me go to business school, so I can learn business things, and I can learn the proper way to do business.” And I got into Colombia and did the Executive MBA program for two years, and I think it was like six months into the program I was like “I think I just wanna start another business.” [laughs] And so after spending a ton of money on this degree that I didn’t really need to start a business, I ended up launching Disco as part of a class that I took, this entrepreneurship class. And Disco was meant to be audio courses. So it was taking my love of podcasting and my love of audio - and audio at that time, if you remember, Clubhouse was poppin’. They raised like billions of dollars…

Juan Andrés Guerrero-Saade: Exactly. Well no, it’s just like, you don’t get Superman and then like all he does is just get cats off of trees. That’s a nice side hustle, but the idea that you have superpowers, you can break into these systems, you can just traverse through places you’re not supposed to be in, and get your hands on things you’re not supposed to have… And you just kind of choose to rob a candy store. Right? It just – it doesn’t make that much sense to me. So I’m happy on the defensive… Like, that’s the worst answer to – I think it’s much more exciting to be on the defensive side of things, but it’s just like a Rubik’s cube that’s kind of turning itself.

Kevin Powell: Yeah. So when I was teaching, when I got called for the school and when I was teaching there, it started with part-time work. So I was doing part-time teaching and still freelancing… And then eventually, my hours got up to be enough to be full-time. But the problem on that was I finally had a decent-paying job, with job security, and that side was good, but teaching introduction to HTML and CSS for two years straight - after a while, it’s a little bit boring. It’s amazing seeing the progress, because that’s when you’re really taking a student from “I’ve never even looked at how do you do a triangle bracket on your keyboard”, to within a couple of weeks they’re able to make a website on their own. So that’s really exciting to see. But two years of just going over the basic stuff, at one point I was getting a little bit bored… And so I decided to start my YouTube channel as a way of being able to talk about things that weren’t extremely simple, and sort of take the next – you know, sometimes I’d do it to like answer common questions that I was seeing from my students, just because I figured if they’re struggling, other people would be as well… But it was more of just this hobby project for me that gave me an excuse to continue doing things that were beyond the very basics.

[09:52] And yeah, about four years into the channel was when things started really taking off. It took a long time before the channel really got any momentum… But about four years in is when I realized that, “Hey, maybe this is something that– it’s bigger than I expected it to be.” Because it really went from like purely a hobby project, to a hobby project that would make me $12 a month, to a hobby project that was “Oh, this is a nice little side hustle.” And then at one point, I was “Well, maybe it could be something a bit more than that.” So two years ago, I ended up going full-time with content creation around the channel, and courses that I created as well.

Ricardo Sueiras: And actually, I’m doing a lot of stuff with students at the moment, because I’m very passionate about education. I used to do a side hustle running a school… Not technology though, just as mainstream school.

Adam Stacoviak: A side hustle, yeah.

Jerod Santo: The reason why I ask this kind of question is because I think a lot of people try to go from zero to one. They have their Chef, but it’s like their open source project, their side hustle… And they’re wondering, “Am I going to be able to do this thing or not? Where are the field goal posts? Is it not full-time, or is it a 200-million-dollar exit?” Those are different ball games that you’re playing there.

Sau Sheong Chang: It would not include sourdough. I mean, people keep trying to give me their starters, like sourdough starter like no I don’t want that. I say no I don’t really like that. I like to do this stuff. And it’s the same thing with some of the stuff that I do, the code that I write as well. It’s totally a side hustle because sometimes I go into projects that I do because I like programming. And some of the things I write, it’s like, “Yeah, because I like writing.” Books don’t really earn much. In fact, they hardly earn me anything. But I like doing it, because I enjoy doing it. So I don’t want to turn that into a side hustle, because I have a day job, and I earn enough from my day job to feed me and my family, and that’s good enough for me. But my day job is not my entire life. I like to do some other things which are hobbies. I don’t need to turn those things into the money-making ventures.

So I just get a little bit annoyed when some people – I mean, they’re all very good-natured. They’re all trying to say, “You know, there’s other good stuff you could do….” But it’s sort of annoys me. It annoys me even more, because I can only smile… And that’s sort of like – I guess, that’s my unpopular opinion.

John Nunemaker: Yeah. It’s funny, because I don’t think back of like what my lessons are, but when I was writing that post, a bunch of them – you know, as I was writing it, I was like “Actually, there’s some things that I’ve learned. I should maybe highlight that.” So there’s definitely some things.

[01:03:48.28] Some of the obvious ones that come to mind we’ve already talked about. It’s like, you don’t know unless you ask. If you’re not feeling fulfilled in your job, or things like that, just find out. “Can I do a side project? Is it allowed?” Make it above board, make it obvious. Say “I’m gonna do this, but I won’t do it on work time.” Start something on the side. I think that’s one lesson.

Another lesson is “Always have a side thing.” Financially, people always talk about investing, like do index funds, and diversify, and this kind of stuff. It’s the same thing in your career. Your career should be diversified. You shouldn’t just have – and I think I learned this the hard way. For a long time – I mean, it was all just on paper. Any financial net worth or something - it was just on paper, with GitHub. There was no diversification. And obviously, I was saving for retirement and things like that, but when everything is just in one company, whether you have options or not, if you just have a job and you work for that company, still everything is in that one company. Always have a side hustle. I think we definitely did that at Orderedlist. We consulted full-time, and we did products on the side. And it wasn’t like, “Well, I have eight hours, so I’ll do six for consulting and two for this.” It was like, “Well, we’ll do six or eight hours of consulting every day, and another two to four of app development.” We worked kind of two jobs for quite a while. And I don’t know that that’s healthy or whatever, but I definitely think having something on the side is a good thing. It keeps you learning, it gives you something to control and make a large impact on, which is nice…

I think those are two really nice things - always negotiate/always ask, always have something on the side… Always focus on long-term value… I feel like saying “always” is probably the wrong way, but hopefully everyone knows what I’m saying. Take everything with a grain of salt. That’s how I take everything everybody else says, so please do that. Don’t just “Okay, he said this, so do it.” That doesn’t make any sense.

But focusing on long-term value, I feel like I’ve seen, just from me, and then also for people around me, and stuff like that - it always seems like it’s the good thing. Long-term is the thing that really matters. Short-term if there’s some suffering, or short-term there’s some financial implications or stuff like that - that’s fine. But focus on long-term value. I feel like that’s something that I’ve picked up.

And then I think another thing that’s kind of interesting (or maybe not) is the kind of two different paths you can go on, at least from like me looking at [unintelligible 01:06:17.19] as a programmer… One side is a startup, and it’s high-impact, you can make a lot of changes… Probably not as good a benefits and salary and things like that. But that’s one path. And the other path is you’re just – I don’t wanna say “a cog in the wheel” in a bad way, but you have your one thing that you do. You don’t wear a lot of hats. You’re on the security team, or you’re on the high availability team, or whatever it is. So those two paths have different pros and cons… And I think it’s actually really good to do both of them. That’s one of the things – when I look back at the 10-15 years that I’ve been doing this, I actually really like that I started with some small consultancies, and then worked at the University of Notre Dame, which was really big. So there’s thousands of employees, and there’s a lot of really great benefits, a lot of nice pros and cons for working there… But I was like, “Oh, I don’t have control over anything. I can’t make an impact because I’m limited by X, Y and Z”, which are just institutional things that aren’t gonna change.”

So then I was like “Okay, pop out to Orderedlist.” Now I have a lot of impact again; everything I do directly affects my bottom line, and the people that I’m working with, and that’s really neat.” And then working at GitHub, same kind of thing, but then eventually it became kind of more like Notre Dame, where again, you don’t have that impact, you don’t have that ability to do it… And I feel like getting that oscillation between the two - now I feel like I’m in a nice place, where I have a really good idea of what I like to do. And if you don’t do both, I feel like you can’t really get that.

[01:07:54.09] That’s the thing I’ve been thinking about a lot lately, is that I’m really thankful that I’ve worked at both big companies and at small companies… And not just small companies, but small companies that I don’t own. I think it’s nice to be an employee, it’s nice to be an employee at a big company… There’s lots of different pros and cons and you should go out and do both of them. If you’re brand new, go out, get a job at a big company, make some money, and then go out and build your thing on the side, and then switch over to your side thing when you feel like you can make it happen. I feel like those are good paths, that aren’t necessarily risky, but they’re focused on long-term value, and they give you a lot of experiences, which will shape what you can actually do on your own later on. Those are probably the main things that I can think of off the top of my head.

Justin Searls: So DevOps, just like so many things in open source, became a hot and trendy buzzword that was heavily marketed and associated with either products or sort of halo projects when it comes to recruiting in like big tech companies. And the original idea that DevOps would be like test-driven development, and if you just gave developers testing, they would incorporate it into their team room, they would automate away a lot of the pain around testing and quality assurance, and then the intrinsic quality would increase at a marginal decrease in that team’s ability to deliver things quickly… And in part, accelerated by the fact that they no longer had other people to have to communicate requirements to, so that things can be tested. So like the theory went, if we just did that with operations, we would get the same lift.

And to me - I had that experience, and it was called Heroku. You know, it was the most DevOps thing that I had ever used in my entire life, was being able to say “git push heroku”, not have to think about my operations at all, but know that it was like taken care of, that I had answers to every question about scale, and about adding on additional components, without necessarily having to turn it into my side hustle or my day job or my identity.

But DevOps as a term has changed, as I think the Agile era of the aughts sort of undervalued and played down the importance of operations as a practice. I think a lot of the people who are the Linux sysadmin archetype of the late ‘90s might be seen as sort of getting their comeuppance now or their day in the sun of lots and lots of new innovations and technology that are focused on meeting the same kind of just core desires… You know, some of it’s like “Hey, how big can we make things? How fast can we make these? How can we automate all of these very fancy and cool, but maybe a little arcane and unnecessary at small volumes and scales, like orchestration of like lots and lots of real and virtual systems up in the cloud?” So DevOps and automation tools have enabled and empowered lots and lots of really cool stuff.

And my experience, of “I just want to be able to “git push heroku” and have my app work in the cloud and not have to worry about it ever again” is, I think, still the pinnacle of what I would want as a developer. And of developers that I’ve talked to that have had that experience in real life, they all wish that we could still have that.

[28:10] And Heroku still exists and it’s still a thing, and I love the people there and I love the product, but clearly, it’s not a flavor of answer that the market is searching for, because everyone thinks that they’re going to need Google scale and Facebook scale kind of tools for the job that’s in front of their very straightforward CRUD app, with very few users. And this is all of a piece with sort of startup culture that everything needs to be a billion dollar unicorn to be valuable, and so you have to presume the conclusion that of course they’re going to reach that scale, so then you may as well just on day one reinvent the universe in AWS through all this automation.

So DevOps as an overall meme in the industry I think has been net negative, and slowed down a lot of teams by way of distracting them, where the fact that teams now have to hire a certain number of DevOps people, quote unquote, “to full time just keep the hamster wheel spinning of their cloud-based computing”, whereas before you might even have had an on-premises server that was just sort of sitting there and was just on and worked…

That’s what I, in spite of the poll results - I think like 44% of the people saying sped up… I think some percentage of those people are just people who like really geek out about DevOps technologies and kind of don’t care and are just team pro-DevOps… And some percentage are just people who like living in the ideology that we live in and probably just never had the experience of what if you could just set it and forget it and not have to worry about it again? Because if it’s a means to an end, why would you want the thing that required a ton of effort and thought and complexity and specialized skills and so forth, and constantly having to read up?

So I’m coming across as pretty anti-DevOps here, but I think that when you look at the replies, the number one point of contention is that no one has a shared understanding of like what we mean by the word “DevOps”. And so just to focus on automation here, it’s - yes, I love real automation, but I don’t think that what we’re typically describing around DevOps related activities is like actually automating anything, in terms of actually automating away a problem.

Linus Lee: The true side hustle…

Chris Ferdinandi: It’s all things vanilla. There’s not necessarily a super-focused “I’m just gonna double down on this one aspect of it.” It’s all of the pieces of vanilla JavaScript. But for me, always with an eye towards simplicity. My primary audience is typically people who are early career developers, or people who have been working on the web for a while, but as designers, and are now looking to transition into learning a little bit of development.

It is currently a side business. It started off as one of those things where like I wrote a couple of things, and I was like “Oh, if I can make a couple hundred bucks off this, I’ll feel happy.” It is increasingly evolving into something that I hope will become my full-time job at some point… But yeah, for now it’s my side hustle.

Eryn O’Neil: Well, my side hustle, my actual passion is blues dancing, which is the dances that people have done – since the beginning of blues music, people have been dancing right alongside of it… And I am a huge nerd about it. I have gotten into primary source research, where I’m reading, going through library archives and stuff like this - super, super-unforgivably-nerdy, but I love it… And I was teaching a workshop, and my now-husband attended it. It’s kind of funny, because a friend of mine and him kind of like noticed each other, so we were like “Okay, we’re gonna get Joe and Amanda… It’s gonna work.” And spoiler, I did not.

Daniel Vassallo: Yeah. And I think one technique that I really like is the idea of negative visualization, that I think applies to everyone, no matter on what end of the spectrum you lie, whether you prefer the structure, stability, whatever, or more chaotic sort of arrangements… You should be thinking of what would happen if what I’m living right now gets disrupted? What if I were to lose my job? What would the consequences be? Would I be able to recover easily? Will I be able to find another job quickly? Would I be able to keep my current lifestyle? Would it affect me significantly? And if you convince yourself that things are fine, then you’re in a good spot. I think you sort of suddenly realize that there’s not much to worry about, and whatever happens, happens. That you will be able to react.

[45:53] But if you realize that you’re in a bad spot, that you’re unlikely to get hired maybe because your skills are now – you know, something I realized for example when I was working at Amazon, in these senior positions, at big companies… There’s probably only maybe ten companies in the world that would want that kind of level or that speciality, because they’re senior executive directors for some specific thing that maybe only Amazon, Google, Microsoft, and maybe Facebook would ever want. So what if those five companies were suddenly to realize they don’t care about this act function anymore? What would it make to you? Would you be able to do something different? Would you want? Would it affect your dignity, or your pride, or would it affect your lifestyle, because you’ll make significant less money? Are you prepared?

So it’s not a pleasant thing to think about the bad things that could happen, but I think it’s a technique to, paradoxically, improve your peace of mind. In my course I like to use the example of the preppers, the survivalists, who worry about a volcano erupting… What do they do? They don’t just worry about it and say, “Oh, hopefully it won’t happen.” They prep. They stock their bunker with food and medicine and water and fuel and whatever… So they don’t want it to happen, but if it were to happen, they know that they have reasonably prepared.

So I would recommend everyone to do this… To think about the worst-case scenarios and how you would react to them. Sometimes you realize all you need is a little bit of planning; maybe you can buy some insurance, maybe if you have some emergency fund savings, you’re in a much better spot… Maybe you realize you need to reskill yourself, to retrain yourself, you need to know some other things to be able to fall back to them if they were to happen.

Some of the people in our community like having some side hustles for this season, to know that if I were to get disrupted, I have something independent that’s going on. Yes, it might only be 10% of my income, not something significant, but if I were to get disrupted or affected significantly, there’s something I could fall back to, and eventually I could [unintelligible 00:48:02.29] which is much better than going back to square one, starting from scratch.

Shawn Wang: So at my day job I’m a head of department now, and I work with creators, and some of them have very valuable side hustles… And I just had this discussion yesterday, of like “Why do you still have a job if you’re an independent creator? Like, isn’t total independence great.” And I had to remind them, “No. Like, career progression is good. You’re exposed to new things etc.” but that’s just me trying to talk him out of quitting. [laughter] No, I have a serious answer, but we’re not here to talk about that.

John-Daniel Trask: But you do gain more and more say over yourself with time. And I think that’s the thing… You could sit down and you could draw a line down a piece of paper and look at the things that you can and can’t control… To give you an example - again, in that first job I started as a graduate software developer. I moved to Wellington with $200. Because frankly, while I’d made a little bit of money through high school and uni with these jobs and things that I’ve been doing, the side hustles, I was also quite aware that the last vacation at the end of university was probably the last time I was gonna get two months of nothing until I retired… Which I may never do. So it was kind of like “Alright, I’m going out big here. I’m gonna spend everything I’ve got.”

[19:54] So I moved down to Wellington with $200 in my pocket, I got this job… And then, of course, I’m in an environment, and you’re going “Okay, so what do the shareholders want? Okay, cool.” Now, somebody might go “But what if I don’t want what the shareholders want?” Well, the next thing I did was kind of go “Right, we have a staff share program. How many shares do I have to buy in this company before I could start to make a credible argument for pointing me to the board of this business?” I do wanna have a say on the environment. Firstly, I don’t wanna alienate the people that are the directors and operators of this business. Secondly, I wanna find a path so that I can be one of the directors and operators of this business, start to look at the shareholders list, figure out who I’m gonna have to try and buy out, figure out how I’m gonna get the capital to do this…

I was fortunate that while it was a fast-growing business, it wasn’t a massive business, so it did look like it was something that was within my capability to do over a few years. And the other thing, too - I’m gonna keep coming back to Bill Gates, since we’ve touched on this topic…

Chris Coyier: Yeah, it’s like a bit of a cheat code for staying on top of the industry, without too much work. I get to benefit from Dave’s insights, and people write in, and… It’s not so much of a lift. We’ve made so many choices over the years of like “What’s the easiest possible thing we can do to keep doing this show? We could have somebody else edit it. We can not change the website very much. We can just stay on this host, instead of change around.” It’s really – it’s to the point where Dave and I throw something on the calendar, and we both show up in a Riverside room exactly like this, we use the same app… And then I forget about it. Our guy, Chris Enns, from Lemon Productions - shout-out Chris - just like logs into Riverside, extracts the audio, edits it all together, puts the MP3 on our host, goes into WordPress, gives the show a title, writes the links… All this, and then hits Publish on the day that – or schedules it for the day it’s supposed to be published. I literally do nothing.

I work with the advertisers when we have one, which is not very much these days, because it just has fallen ,through and I don’t hustle for it, because it’s just – I don’t have the time for it at the moment. Even our transcript lady, Tina Pham, has access to the WordPress site. So when she’s done with the transcript, she logs in, pastes it into the right text area, and hits Save on the show.

Justin Searls: Yeah… Which was closed down, and shuttered and no longer exists, and now there’s another thing called C.com, which owns the twitter.com domain. So on that site, there was an argument about the word “passion”, about like nine years ago. And I think that the people complaining about the word “passion” as used to describe programmers, either in like job postings, or as a descriptor of how somebody sees themselves about their job… You know, Chad Fowler wrote a book called “The passionate programmer”, and I’d read that book, and chatted with him a bit about it just a couple years prior… And I liked that I felt passionate about software. And then there was a group of folks on Twitter who tended to be younger, tended to be more from the Bay Area, where I’m sure the cacophonous sort of trilling sound of like really, really hustle bro recruiters trying to get people – just squeeze every ounce of energy out of the stone to work overtime on their startups, in sweat equity and so forth, was like a big kind of part of that. It was like, you know, you don’t want to take people’s joy and sort of use it like an olive press, and just get some sort of resource out of it… But there was a valence, I think, to a lot of the argument that was like “Hey, this is just work. Let work be work. how up at nine, out at five. You get paid for that labor”, and to expect it to be something more, it bleeds and blurs those lines. And all of that was a completely valid debate to have, but the debate had this subtext that wasn’t communicated, which was if I looked a couple years prior to teams that I was on, let’s say six out of eight of the people on any given team I would join were folks like me, who programmed for fun in their spare time, and we’d have all these really deep and nuanced debates about editors, and tabs, and we would go out of our way and spend weekend time going and like “Oh, I spiked this thing out” or “I tried out this refactor, I did this other thing”, and we’d butt heads with lots of toxic alpha male energy on a really geeky topic… And to the two out of eight in that team, it was probably not a super-fun time most of the time. But being the majority, what I was experiencing as one of the people who kind of treated software development as a full-contact sport when I was at work, and like this personal kind of journey that I was always on in my spare time…

On Freund: Exactly. No one has even managed a real estate inventory at that size, with that model. Right. So the hotels have what’s called PMS, property management systems. And we looked at a lot of them; we couldn’t get them to work for our model. It just doesn’t fit. And even hotels - when they go through mergers, let’s say Hilton buys a property somewhere… Now they have to integrate all the systems, and that’s actually really complicated in itself. But then every property is kinda like its own domain, whereas at WeWork you wanted everything to be part of the same system. A guest at a Hilton doesn’t book a room somewhere else and has to go seamlessly with the same key card the next day, right? But at WeWork, everything is connected.

So just managing that scale, managing that model - nothing like that ever existed before. And you see that in other co-working space companies, where they might do well on the first building, maybe second one, third one, but then you realize that those buildings are actually running on the hustle and grit of the founders, and it’s really hard to get over that five-building hump; definitely not 10 or 12.

Jerod Santo: Yeah. But I couldn’t – and I appreciate the hustle, but I do not appreciate somebody who’s going to send the same person five unanswered emails. What’s your limit, Zeno? How many emails would you send somebody if you don’t get a response?