Changelog Interviews – Episode #498

From WeWork to upskilling at Wilco

featuring On Freund

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This week we’re joined by On Freund, former VP of Engineering at WeWork and now co-founder & CEO of Wilco. WeWork you may have heard of, but Wilco maybe not (yet).

We get into the details behind the tech and scaling of WeWork, comparisons of the fictional series on Apple TV+ called WeCrashed and how much of that is true. Then we move on to Wilco which is what has On’s full attention right now. Wilco has the potential to be the next big thing for developers to acquire new skills. Wilco aims to be the ultimate simulator to gain new skills on a real-life tech stack. If you want to skip ahead, you can request access at — they are moving our listeners to the top of the waiting list.



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Well, we are joined by someone whose name I literally cannot pronounce, so I’m gonna – I’ve been allowed to call him On, like he’s always On. On Freund. On, welcome.

Thank you. Thank you so much. That wasn’t too bad, by the way, with the name.

Very impressive, Jerod. Good job.

I’ve been practicing for minutes now.

Behind the scenes, listeners, we’ve been practicing how to say his name, and it is hard.

I can actually confirm that really happened behind the scenes.

Yes. Two letters, very hard.

It’s always – the simplest things are the hardest, right? It’s like software. [laughs]

Yeah, that’s true.

Like, that’s a one-point story, and then you get into it and you’re like, “Oh, it’s more like a 13.” [laughs]

I like it, I like it. Dovetailing right into things.

So let’s get right into it. You’re with Wilco, a new startup helping people to upskill, which I think is also maybe new tech jargon, I don’t know… Has that one been around a while? But I’ve started to hear more and more people talking about upskilling, which I just thought was learning… But help us out maybe there, On - is upskilling like this new, cool learning lingo?

That’s a good question. [laughter] Actually, now that you’re saying it, maybe we invented the word, maybe we didn’t, but we thought it existed. But I think what really differentiates upskilling from learning is that learning is usually focused on theory, whereas upskilling is more about the skills and bringing them up. It’s how you take your skills and take them to the next level, rather than learn some new theory.

[06:02] Yeah. I guess it also kind of implies there’s some sort of skills in the first place, and you’re going up from where they are… Whereas sometimes learning can be like from a complete scratch, complete baseline.

Correct, yup.

Too, just fast-forward a little bit, it kind of rounds out all the skills you want to build to be a good developer. So not just writing code, or understanding computer science, or different aspects… It’s communication, it’s a lot of different things that come into play, as it’s sort of layering on like a cake. You’re learning.

Exactly. It’s all the stuff that you learn by experience, not the stuff you learn in college.

Well, speaking of learning by experience, you had a heck of an experience as the Vice President of Engineering at WeWork before this startup of yours… WeWork’s been in the news, it’s been fictionalized…

Oh, you’ve heard about it.

Yes. [laughter] Actually, what’s funny was I was pretty ignorant of WeWork. I just thought like, it’s a startup that does co-working, for a very long time, until it hit Apple TV Plus with Jared Leto and Anne Hathaway, and I’m wondering how ignorant am I have it still, to this point, having watched the series? Did I learn anything that was real, or was it just all inspired by true stories?

So I think I think the series was actually really good. Not a big fan of the Hulu documentary, but I thought the series was really good. But it still is fiction. It’s based on a real story, but it is fiction. Characters have been merged, eliminated…

Made up…

…butchered, made up… Timelines have been completely mangled… Things that happened in 2014 show up as 2019, and vice versa. Or things that never happened at all are there. I think it’s a good show, I think that they managed to capture some of the spirit, but not all of it.

Will there be a season two, or does it conclude? Jerod, did you watch the whole thing to the end?

I watched the whole thing to the end. I do not believe there’s another season, because the story was kind of over at the end, right?

Yeah. Well, at least what we know already has already happened, and it’s done. It was actually funny, we have a WhatsApp group of WeWork alumni, and someone wrote something about not watching it, and no spoilers, please. And everyone’s like, “Dude, exactly how this ends.” [laughter]

That’s awesome.

Well, the fictional version of it, at least.

Yeah. But you shouldn’t expect any plot twists if you’ve been through the ride.

Yeah, I suppose. The overarching theme is sort of set in stone based upon reality… Hopefully. So it’s interesting seeing where you’re at now with Wilco, and what you did there… How much parallels – like, did you go through the pains that Wilco now solve there, scaling? I think one of the big things, as Jerod was saying, with understanding what WeWork – I almost called WeCrash now, just because… I’m sorry. [laughter] But I do know it’s WeWork. WeWork was more of a real estate company than it was a tech company, at least from the outside. And having been in your position while there, was it a tech company, and what did you experience there to sort of take into what you’re doing now? How much translated to what you’re doing now?

So I think that these two things aren’t necessarily mutually exclusive, right? So Uber is a ride-sharing company and a tech company, right? Amazon is a logistics company, and it’s a tech company, ignoring the AWS section and looking just at the commerce part of Amazon. And just like Amazon, just like Uber, WeWork’s technology is what enabled it to work at scale. And there was absolutely no way you can open the amount of desks that we were bringing to the market every month without really solid technology, that does everything from finding the neighborhoods that should be the next locations, managing the real estate process, from prospecting, to contracting, and all of that… The buildout of the day-to-day operations… And then of course, things like the member network that every member had access to, or the app that actually let them do everything… But just thinking about a day, the first of the month, and you have 30,000 people coming in and moving into WeWork that day, you just can’t do it without the right kind of tech. And sometimes the tech is invisible… Like your key card that you walk into WeWork, you get it on your first day; you don’t even need to do anything to activate it. You use the app to activate it, and then it just works. And it works in your building, and it works when you change companies, or when you change buildings, and it works when you book a room in a different building… It just works when you need it to, and it doesn’t work when you don’t. Like, it doesn’t give you access to buildings that you’re not supposed to have access to.


That sounds super-simple. That actually got us invited into hotel conferences… Because they can’t get it right. Like, how many times have you checked into a hotel, got up to your room, realized the card doesn’t work, went back down and then they inserted into this machine that reprograms it… At WeWork a card never goes through reprogramming, ever, in its entire lifecycle, even when you return it and it switches to someone new.

So a lot of internal tooling, really. A lot of bespoke, brand new, innovative – brand new because nobody had really done what you had done at WeWork at scale. Like, sure you’ve had office buildings with access and shared desk spaces and whatnot, but not at the scale, globally, like WeWork had been, in comparison.

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.


Yeah. What was your time period there?

So I joined in the summer of 2014. We had about a dozen buildings. My employee ID I think was 114, or something like that…

Pretty early.

But we were less people than that, because not everyone stayed. It was a very different company than what it had become when I left in October of 2020. And it went through crazy highs and crazy lows, and eventually you could say I did nothing at the company, because it ended up being worth the same as it was when I joined in 2014. [laughs] So I contributed nothing to society for six years. [laughter]

I wouldn’t put it like that, but I get what you mean.

[14:09] So one of the things that WeCrashed show portrayed, which I love your take on - in light of some of the things that you’re talking about, the things that you worked on while you were there… Of course, you were not doing nothing for six years; you built a lot of things. And there was this plotline where it was like “Adam Neumann had to continue raising more money, and he had a harder time raising money around a co-working real estate company than he did around like a software startup company… Because of course, VCs want to invest in things with like huge margins, right? And so he had like this whole – it’s like, it’s a tech company, it’s a software company… And the insinuation from my take of watching the show was like “But he was kind of making all that up, and it never really was.” And I’m wondering if in light of what you’ve been telling us - like, does that sentiment offend you, or do you think it’s like made up whole cloth, or what are your thoughts on that?

It does, because it’s close to home, and it’s one of the most inaccurate parts of the show.

So the whole show is Adam talking to Masa sometime in 2017 I think, or 2018, and then making up a technology department for the company, calling it WeWork Labs.


Now, WeWork Labs was a completely different thing, by the way, which I also did at some point, and loved, and it had nothing to do with technology. It was a startup program for members who were running their startups…

Like an incubator?

Not really an incubator, but more like an ongoing program where you can get more than just real estate. If you join WeWork, you get more support, and access to – investors help with BD etc.

Oh, I see.

So that was WeWork Labs, and it was a great program. We had like 87 locations worldwide, and we were helping quite a lot of startups.

So it was like a customer perk. Like, it was a perk of their customers.


Okay. That’s cool.

Yeah. But WeWork Technology existed since way before I joined. when I joined, we already had like nine developers or so. When I left, or let’s say before the whole show… [laughter] So before the show, we were I think 1,000 developers at some point…

Wow. That’s scale right there.

That’s scale. It’s not as if Adam said, “Oh, we need a technology department. Let’s hire 1,000 people.” That grew organically from sometime in 2012, I think, all the way to 2019.

So you said nine when you began in 2014. Is that correct?

And it was founded in 2008. So that’s six years of growth before you joined. I mean, rough founding date.


Okay. Google says 2008, so I was based on Google’s “When did WeWork get founded?” It says 2008, in SoHo.

So 2008 was GreenDesk. That was Adam and Miguel and a third partner… The third partner ended up buying Adam and Miguel’s share of GreenDesk, and they went on to start WeWork.

That was in the show.

That was in the show, yeah.

Yeah. Okay. So let’s just say 2010 then. So you’ve got four years of business growth and the need for technology. You’ve got nine developers when you begin, and that’s in 2014. And 1,000 in 2020. Is that accurate?

Yeah. But also, we’ve had a dozen buildings when I joined in 2014, and we had about 1,000 in 2019.

Yeah. The scale was insane.

So a developer per building - that doesn’t sound too bad, I don’t know.


I would say, yeah.

So we found on WeWork Technologies’ blog, Matt Star went through the history of This was written back in 2017, and I think you’re thanked for helping contribute or something to this post. And that’s a nice kind of run through of – that’s just the .com. The technology behind that started off as WordPress, and there was a new WordPress theme, then Ruby on Rails, then there was like “We’re rewriting the whole thing” and it was like now it’s Node.js, and then it’s a static site generator… Like, this thing was iterated on, almost just like thrown out and started over, it sounded like. I’m sure you had something to do with that as well. Was this part of your job there?

[18:19] Yeah. I mean, obviously, when you make it sound like that, it sounds like all we did was just rewrite the website, but…

No, not all you did, but like somebody was doing that work, for sure. Right?

Someone was doing that. But the goal wasn’t to rewrite the website, it was just - the website, our front-facing website went through several changes of a) brand, and many of those brand changes were also an opportunity to rewrite the site in a way that we thought was more maintainable.

And b) also a big part of joining WeWork happens on So this was actual business logic on the website, that was going through a lot of changes. But it’s not as if every one of those iterations we went ahead and said, “Alright, let’s dump everything we’ve done so far, and do something completely new.” It was more iterative than it might sound. we have this backend working, we have a new brand… Let’s use the opportunity to maybe switch over to a static website on the frontend, with an API… What today is called JAMStack, but back then I don’t think had a name yet. But it’s not as if we started it from scratch.

Sure. It’s a really nice post. I will link it in the show notes. One of the things that’s cool about it as he goes to each iteration, which I think is called John Quincy Adams, because he was like the sixth president, and this was the sixth major revision of the .com…

I’m not an American, so don’t ask me to quote presidential names and numbers… Not going to work.

I am an American, but please don’t ask me to quote presidential names, or numbers…


I’m just reading from the blog post. I will say, what’s cool about it is, to your credit, the logic and reasoning goes along, and what we’re trying to improve on each version, and what things we’re experimenting with. And he even goes as far as listing how many current buildings you all owned at the time, and then how many countries you were operating in… Which is a nice way of telling that story.

By the way, countries are one of the biggest hurdles, and one of the biggest needs for technology. So just being able to bill in multiple countries is super-complicated, especially when you have customers that are cross-border. you have Amazon in Germany and Amazon in the US, or something like that, and you need to bill them… It’s super-complicated. And what - we actually went to a lot of billing companies, and we asked them, “Let’s say we decide on a new market we want to open. How long would it take you to add that country’s billing to your system?” And they said, “Well it would take us about two years to add a country.” And we’re like, “We’re going to open a building in six months. Actually build it, and do everything around it… And it’ll take you two years just to do the billing?” And we ended up having to write our own billing system because of that.

Well, when you scale beyond the speed of others, other vendors, in this case you have to. You have to build the team to innovate, you have to do the innovation… Because they’re not motivated necessarily to move faster than the two years. I mean, sure, they’d like to, of course, but if they just can’t, you need to; you’re already building the building, there’s ground broken, so to speak.

Exactly. And that’s why Amazon started AWS - they needed all of those computing primitives to work for them, so they can run their business on top of that.

So the scale is obviously a huge factor, but in addition to that, or beyond it, I guess, what were some of the biggest challenges that you faced in your tenure at WeWork in terms of engineering?

[21:57] Well, I had to explain why WeWork needs an engineering department about ten times a day. That was one of my biggest challenges.

[laughs] Who did you have to explain it to?

Everyone. My parents… [laughter] I had to explain it to my parents every day. And just reporters, candidates, peers… Anyone would basically come up and ask me, “Why does WeWork need a technology department?” And everyone seems to think it’s so easy to run all these buildings. If I had a penny for every time someone said, “Oh, that’s easy. I’m going to open my own co-working space at a building.” maybe I could have funded the WeWork instead of having to go for an IPO the next WeWork round.

Wow. Well, as you said, it’s so invisible; the technology you built was so invisible, because I guess you just assume key cards just open doors, and that’s easy, right? Or that you never have to reprogram it; like, the tech involved in not having to reprogram it every single time like a hotel might, for example.

I actually think that a transparent product is sort of a perfect product. So there’s a difference between perfect and best. Because perfect is kind of like a local maximum; everything you do is going to make it worse. And a transparent product is just like that, because everything you do is going to make this worse. If we changed anything with our key card algorithm, it would have made things worse, but no one notices it. And that’s amazing. The things in your life that you don’t notice are the things that are really working well. And someone who would try to replicate WeWork would get that wrong.

It’s like if you ever moved into a house that you were involved in in the construction phase, then you sort of think about all these things that you’ve got wrong, and you’re like, “Oh, next time, I’m building a house–” I mean, people don’t build houses that often… But like, next time I’m moving somewhere, I’m going to make sure that the kitchen has this and that. But what you don’t take into account is all the things that actually worked. And then if you had to redo everything, you’d probably get a lot of the basics wrong, because they just worked the last time and you didn’t notice them. They were just there. All the pipes are in the right place. Amazing. But what guarantees they’ll be there the next time if you don’t pay attention to it?

Yeah. I’ve used this analogy before, mostly around open source infrastructure, and how that’s invisible, and therefore it doesn’t get the attention that it needs in order for it to thrive. And it’s the analogy – maybe this will be lost on you, On, because you’re not from the States, but in American football… I don’t know if you ever watch American football.

Oh, I’m a huge fan.

Oh, you are. Okay. So this will work out just fine. So the offensive line–

I did live in New York for five years.

Okay, good point. But then you’ve got the Giants and the Jets, so I’m not sure how you became a football fan in that case…

Oh, of course Giants…


Go Big Blue, come on. Easy.

Somebody out there listening is like “Of course, Jets – oh, what?! Come on, On! Wrong team!” [laughter]

Somebody’s out there rooting for the Jets. Probably Gary Vee.

Gary Vee, yeah.

The only Jets fan left… Just kidding, Jets fans. So the offensive line - it’s very much like that. When the offensive line does their job just right, which - let’s just simplify it down to protecting the quarterback. There’s other things, on running plays, and stuff… When they protect the quarterback and he gets the pass-off, the cameras are not on them. the quarterback’s thankful to them, but the fans aren’t paying attention to them… Like, the only time the offensive lineman is featured with his big ol’ mug on the television zoomed in is when he just missed his block, and the quarterback got sacked. That’s like the transparent feature. That’s like the software that nobody notices; when it does its job right, there’s no glory there.

Being a Giants fan, I actually don’t know what a functioning offensive line is… [laughter] I haven’t witnessed one for about 12 years now.

I’m loving it… Yeah.

Fair enough. But if you did, you’d ignore it. You’d take it for granted, right?

I think we had an offensive line at some point, back in 2008 or something.

[26:02] Yeah, that’s tough. Some roles, they’re just like – there’s no glory there. And it sounds like running the software team for a co-working company, regardless of the scale of like one building to 1,000, people don’t give you any respect; they just think that’s like just an easy thing to get done.

That’s why you go ahead and you start a pure software company afterwards, because then people are gonna –

I was gonna say, this leads us into Wilco, right?

People are gonna want you on podcasts all of a sudden, and the news cares about you in a non-gossipy way… Yeah, software is great. Who needs operations…?

It sounds like you’re learning and adapting.

**On Freund: “**Never stop developing”, yeah. Which also works for real estate, by the way… Never stop developing.

So now you are here with a software startup that’s right in your face, no more transparency behind the scenes… Wilco, “Never stop developing.” You’ve raised some money, you released a product, number one on Product Hunt for the week, and I think it was like number three for the month, which is a great launch by darn near any measure… Tell us what you’re up to, what are you working on? Gamifying upskilling is what I would call it, but what would you call it?

Yeah, it’s not a bad way to call it… We spoke about upskilling in the beginning and what it means… But it all started with the realization that the only real way to gain experience for developers is on the job. But when you gain experience on the job, it’s a) very slow; people take years to sort of gain the initial experience that they need, but after that it’s even slower, because the more experienced you are, the less likely you are to come across new types of scenarios.

b) It’s very error-prone. I’m sure you first-hand witnessed many production outages, deleted database tables, etc. And c) it doesn’t provide equal opportunity, because you and I could be starting at the same company, same time, both of you are way more talented than me, but I get to a team where I get better access to production, or better mentors… And I’ll very quickly open up a gap that’s going to be really hard for you to close. And if we’re talking about groups that traditionally are underrepresented in tech, they already have an experience gap, and they tend to get to teams that don’t actually allow them to close it.

[30:23] So you have this problem with gaining experience, but everyone in the world is trying to teach you the theory of writing code… But who cares about that? Like, why is writing code that important? you start your first day on the job, your manager is not coming up to you and saying, “Hey, write me some code. Here’s a function. Do something with it.” Your team lead is probably going to say, “Hey, get yourself acquainted with the team, first of all.” But guess what - nothing has actually prepared you for working on a team if you went to college, or a bootcamp, or definitely not an online course. And they’re going to say “Get acquainted with the build system, and with the architecture of our product”, and then you’re left kind of speechless on like, “Wait, where’s all the stuff I learned in college? Where’s the list I’m supposed to reverse?”

Bubble sort! Did you write bubble sort?

Yeah, exactly. [laughter] And you’re completely unprepared. That’s what happened to me on my first day on the job. And I, by the way, got to a very dysfunctioning team on my first job. This was kind of a blessing and a curse, because on the one hand, I had to touch production on almost a daily basis, because something was always breaking… But on the other hand, I didn’t have good mentors. I didn’t really have a good team that I can bounce ideas with. I had other colleagues and other teams that helped me out quite a lot… But that experience shaped a lot of what ended up being Wilco, I’m not gonna say how many years down the line.

And then everyone’s so obsessed, like I said, with writing code, and a friend of mine gave me this great analogy. He said, “If I want to know the state of the art in medicine, I’m going to go to someone who just graduated from med school. But if I need someone to operate on my shoulder, I’m going to go to a surgeon with 15 years of experience.” And it’s kind of like that for software engineers. If you’re fresh out of college, you’re probably doing bubble sorts way better than someone with 20 years of experience. But if you need someone to write a production system, if you need someone to maintain it, if you need someone to build the team, and the culture for that team, and the workflows, and have things like an on-call rotation, and all that, you need someone with practical, hands-on experience, and there’s just no way to get it.

So how is Wilco going to give you that? Because - is it actually real? Is it? I mean, it sounds like there’s no way to get it… But is this going to close that gap somehow? I know what you’re up to, but at the end of the day, how real can it be, if it’s not real?

Well, it’s not real-real, but we try to keep it as close as possible.


Yeah… I mean, we looked at other domains and tried to see “Alright, what are other people doing to solve that problem?” And we looked at pilots, and they have a flight simulator, because guess what - a regular flight is not going to prepare you for that time you need to land on the Hudson.


a captain’s call - you had to train on the simulator to do that. And we said, “Alright, let’s do the flight simulator for software developers.” And then we came up with this idea of joining Fantasy Company. But we really wanted all of the complexity of real life in it, so that Fantasy Company has a production-like system, with logging and monitoring and analytics and load balancing… And it has a real dataset, not just five records in a single table. And it has the biggest mess of all, which is other people.

[34:04] So you have your team lead, and the DevOps person, and colleagues, and product managers, and all of that, and now you need to figure out how to work at that company, and run through all sorts of scenarios that we call quests. So a quest could be – we have a performance problem in production; figure out what happened, what’s the root cause, what’s the extent of the damage, fix it, and communicate it to stakeholders. Now, you might have learned how to fix it in college or at a bootcamp, but how do you even know that something’s wrong in production? What do you do to investigate it? When do you go for a quick and dirty fix? When you go for something more meaningful? How do you ensure that lessons are learned and implemented? All of these things… These are the things that you can only really get by playing around and making mistakes.

Learn by doing is the old adage, right? Like you had said before, you learn on the job, that’s learn by doing, in many ways. Either you’re gonna pick up a side project, a thing for you to play with while you also work, to gain that experience. You might play with a brand new framework, just to see how it works, whatever… But you have to learn by doing, and I guess that simulation is that doing, in probably the most comfortable way possible - joining an actual company, or a fictitious actual company, which is sort of an oxymoron there… But you’ve got Vanessa, also known as Ness, awkward if you call her mom, you’ve got Navi, you’ve got Ben… These are some characters you find. And maybe I’m jumping the gun a little bit, but the first thing you do really is you get invited into Snack, which is a play on Slack, I’m assuming…

I think that’s a fair assumption…

Probably exactly that, right?

It’s a corporate messaging tool, that may or may not be related to some other brand but… It’s its own corporate messaging tool. [laughs]

Sure. What I think is interesting though is that such a real-world scenario. It’s a real perfect simulation of what will probably happen. I was just telling Jerod before this call, I have done what we’ve been doing here at Changelog for a while, so our Slack (our Snack) is – I’ve never joined it as a new person to join the organization, so my empathy and my familiarity with doing that is so foreign, because I haven’t done it. But if you’re a new engineer, going into a new role out of college, or changing jobs, or whatever - like, this is every new change job scenario… Meeting the new team, finding the repositories, understanding the codebase, what is the domain knowledge, what are the complexities? How mature is the team? Is it a monolith, or is it microservices? Is it many repos? All these different things you have to figure out to sort of understand the foundation you’re standing on. And some of that you learn in the interview process, and may actually be part of your criteria use to select your job, and choose that team, and go that direction… But this is so, so similar to what it would take to join a company. I think it’s kind of profound that that’s how you landed, that’s what you’re doing here, because that’s exactly what you do when you join Wilco.

Yeah, exactly. And all these side projects are great, but they usually don’t actually get to flex your team muscles, right? Because you’re working on your own on the side project. Or maybe it’s a very big open source project, but then in many cases it actually doesn’t operate like a company; it’s very different.

I contribute to open source a lot, but there’s no production instance that I have to take care of. It’s usually things that other people run on their computers, or maybe it’s libraries that people use, but it’s not an actual system I have to maintain. And there is no team in the traditional sense. And all of these things are what we really wanted to make sure that you get exposure to with Wilco.

[38:02] So I’ve also met Vanessa, aka Ness, and Adam and I have gone through the first-run experience with Wilco. I love the concept, I love what you’re doing. A lot of the reasons that Adam also explained resonate with me. Snack is very clever. I wonder how much –

It’s completely original. I don’t know what you’re talking about. It has nothing to do –

[laughs] I wonder if you need to change some more letters for you guys to stay out of any sort of –

All of the characters are completely fictitious. And any relation to everything is made up. Yeah.

Okay. Disclaimer aside…

The next time I’m bringing in my legal team for this podcast. [laughter]

Let’s talk about the uncanny valley, because flight simulators have to be incredibly realistic for them to be effective and useful. And I know this is a just-launched product, and you guys are on your way. Once you start trying to talk with Ness, for example, as you would… Like, if I join a team - and maybe I’m just a weirdo, but my tech lead or my boss is like talking to me, I try to build a little rapport. And the first run was like, “Oh, I’m loving this simulator. It’s all like a real company.” So far, I’ve gotten to install Dockerface. I’m not very far in. It’s like, this first quest can take an hour. It’s like, “Well, I don’t have that much time, but…” I have Docker installed, but I haven’t got to where I’m actually doing things yet. I love the different quests you have laid out; search party, fixing a bug, funnel drop, these different names, performance etc. But you’re still at a phase where it feels real until it’s not real anymore, and you’re like, “Oh, Ness is like a pretty simple chatbot.” If that. Like, maybe at this point it’s like a few hardcoded answers. Now, I’m not trying to call you out here, I know you guys are just getting started… I’m curious what the plans are in like fleshing out this universe, because it seems like you have like all these hooks to hang and things on, and you maybe need to get us further across that valley before it’s like – it doesn’t need to be believable, but I have to be able to suspend my disbelief a little bit and feel like I’m part of a team, ?

Yeah, sure. So first of all, Ness is one of my favorite characters; not that we have that many, but she’s one of my favorite characters… And I can actually envision her responses to different scenarios, but you’re right, the product is still not completely there. She’s not the most sophisticated AI bot out there. It’s good for now, but she’s obviously going to become better as time goes by… And you’re also going to get other characters involved. And each one of them might have their own quirks.

So here’s a scenario from real life - you’re rewriting a legacy component, and the person who wrote that component actually feels very attached to it, and doesn’t want to help you. And that’s something you have to deal with, right? But that person is going to be an NPC, and non-playable character. And we will try to make that, obviously, as realistic as possible. And one of the things you’ll have to figure out is how to get that person on your side, or how to get their support, despite the fact that you’re trying to destroy the very thing that they love so much.

Real-world office mechanics… The power struggles, the passive-aggressive circumstances…

Exactly. And maybe there’s a developer with a big ego, and you find a production bug, and they say that their code is perfect… And it can’t be there. It has to be somewhere else. Right?

Right. It’s a feature, yeah.

When I was young, I used to tell product managers that – they would ask me, “What would the product do if this and that?” and I would tell them, “Just tell me what it does, and I’ll tell you why it’s the right thing.” [laughter]

You used the term AI bot - is that accurate, or is it a misnomer at this current state? Is it truly an AI bot, or is it a complicated if-else statement?

[42:05] It’s on the spectrum between a very simplified, automated canned responses, and a full-blown AI bot. And it’s getting better, by the way, all the time. So we’ve picked up on quite a few things…

Well, talk about transparent - that’s the kind of feature that could get better now that you have the framework in place. All you’re doing is modifying the responses; everything else is there.

Exactly. And you really need that corpus of conversations to make it better. It’s really hard to make it perfect the first time.

Oh, for sure.

You really want Ness to interact with a lot of people, hear how they respond, how they try to plant all these traps for Ness, and then you can make her better.

So we mentioned the simulator… I brought up gamify, because in addition to this faux reality that you’re working in, you also have a lot of the game mechanics of badges, and XP, and Wilcoins, which - I’m not sure if that’s a web three thing, or just a cool name for a web two thing; maybe you can help us understand that. But tell us some of the other ideas that you have at play. I know you’re getting these things out there and they’re not all fleshed out, but what are some of the ideas?

So actually a lot of it is fleshed out, even if it’s not there in the product just yet… But I also don’t want to give away too many spoilers.

Ah, true.

But let’s say anything – the Fantasy Company that you’re joining has way more than meets the eye to it. It might not be the company you think it is.

Oh, so this is gonna get even more interesting as I get further into this, that’s what you’re saying.

Exactly. Developers, they have an intrinsic motivation to become better. I was listening to the podcast you did with Lee Robinson, and he talked about education quite a lot, and how that’s the part of the job of a dev rel, and he mentioned how developers are always eager to learn more. But the thing is, all of it is usually very boring; all of it is very top-down, and that’s why we wanted to do something very different, and do it in a game-like environment, so they actually feel like they’re having fun along the way.

We brought in an amazing game designer, and we brought in amazing graphic designers… Not that our game is like 3D shooter/graphic-level, of course, but… You know, getting all the graphics down… You mentioned the quest names, but also their covers, and all of that - it really had to be a very specific design for it to work, for it to feel fun, yet genuine and inviting.

I think Jerod said that before, suspend disbelief. I think that’s a key ingredient here. One, you’ve got to have fun. But then it’s got to look good and be believable to suspend that disbelief. You know it’s a game, because you signed up right? Like, you opted in. Somebody didn’t make you do this; maybe we’ll get into that, because there are team involvements, so maybe there’s –

It’s just like that movie, The Game, with Michael Douglas, but then it’s just a little bit more–

[laughs] Yeah, I hope I don’t find a clown in my living room. [laughter]

With a key, yeah.

With a key, exactly…

It’s got to be believable enough though, right? To suspend that disbelief, you’ve got to have a believable enough – that is one, quality; two, having fun… Actually how it looks, how it responds… That’s a necessity to, I guess, suspend disbelief, but then also let go a little bit and have fun, which is really where learning really is key. That fun component is a psychology thing; you learn way more, and you get more immersed in it, and you retain that knowledge much more if you actually have fun and enjoy the process. It’s kind of like exercise. I get better results when I enjoy the process of exercise.


[46:02] I’m not a big fan of just going and lifting weights for the sake of lifting weights, I’m more of a fan of going and being active, riding my bike, or doing different things. That’s where I exercise better, and that’s because fun’s a component of it

Exactly. And that’s why we sort of have two brands, which is - Wilco is the fun brand, and it happens in between the quests. And then when you’re in a quest, you’re in Anythink, the Fantasy Company, and that is trying to be more real. And it’s kind of like, if you play a first-person shooter, then between encounters it doesn’t feel very real; like, you’re never preparing for an encounter, you’re never having to deal with defects in your gun, or anything like that. But when you’re in an encounter, everything is real, and they try to mimic reality as closely as possible. And you have to get aiming to work right, and you have to get the action of the gun, and all of that… The worst metaphor ever, sorry. But that’s kind of what we went for. When you’re in a quest, it has to be very realistic; you’re talking to your colleagues on an actual chat product, you’re using your IDE, you’re using your command line. But then in between quests, you have that fun, Wilco brand and design that ties everything together.

I was thinking before too, familiarity. When you’re new to the workplace, you have no experience to say “This is normal.” Right? And it’s almost like that, like - this simulation is a version of what might normal be… And so the fact that it’s so similar to what normal might be is kind of like reassuring, because if you have no experience to know what normal is, then it’s kinda like, “Well, this is pretty close, and this prepares me, despite my lack of experience, my lack of having a first engineer job”, or whatever it might be, as you upskill, so to speak. You’ve gone through a bootcamp, but have you actually worked somewhere before? And it’s not just about coding, it’s about team interaction, it’s about understanding the codebase, it’s about domain knowledge, and all these different things that are involved in doing your job, not just “Can you reverse a string?” for example.

I couldn’t have said it better. Thank you. [laughs]

So as you all are imagining this world and creating this world, there’s a lot of different aspects that you’re talking about… And psychology, and storytelling, and design… I’m just curious, where are these skills coming from for you and for your team?

I know, before the show you mentioned you’re a film buff, so I guess somewhere in there there’s like storytelling hooks. But how do you know that what you’re doing is compelling, is going to work, is going to actually pay off at the end of the day? Do you have history in building immersive games like this, or you’re just like, “Well, we’re gonna give it our best shot”? What’s the deal with that?

Well, luckily, I don’t have to do everything myself. We do have a sizable team, and we have a game designer, and she’s built a lot of immersive experiences, both online and offline, so she knows… In the beginning, she would keep saying, “We should really do this and that”, and we were like, “Oh, that’s never going to work.” And eventually we said, “Alright, we trust you. Do it.” And guess what - we were always wrong, and she was always right. Game designers apparently know what they’re talking about…

And our graphic designer is a big game buff. She actually writes for an Israeli publication about gaming, so she knows what are the right graphic elements to make a game work. And even though it’s not your typical game, and you can’t really put it in any genre of game per se, but the mechanics, like you said, need to work. And having the right people who’ve built these types of things obviously helps a lot.

So you said this is a software company though… So far we’ve been talking more about games.


Where’s the software? What’s the software stack? Give us a glimpse into the software stack. What powers this cool simulator?

Well, what powers it is an engine that we’ve built, that takes a quest in a domain-specific language and turns it into a quest in multiple different stacks. So we write a quest once, and then you have the Python and PostgreSQL version of it, but you also have the Node.js and MongoDB version of it. And it doesn’t work for all of them, right? If this question is specifically about adding indexes to a SQL database, then obviously the Mongo version is not relevant. But in most cases, it’s a write-once-run-anywhere kind of engine… And we just added Python support last week, at least at the time of this recording. And we don’t have to build every quest in Python anymore. We just build new quests, and they’re available in all the languages that we support.

So that is, I would say, our main piece of technology. And eventually, we’ll have an editor that actually lets anyone create quests on top of that engine. And this could be the individual that wants to show off “Hey, I built a Kobayashi Maru.” Or this could be a company that for employer branding purposes is saying, “This is what a typical day at our company looks like. And by the way, when you’re done, send us the output and let’s see if you’re a good fit.”

Or this could also be a company that is reaching out to developers or catering to developers. A lot of these companies are already spending a lot of time and money on advocacy; it’s blog posts, and it’s videos, and it’s conference talks, and manuals, and references, and you name it… But we give them something that actually allows them to give their third-party developers actual practical hands-on experience with their product.

[54:18] That’s really interesting, to go from this upskilling opportunity to a not just upskilling, but also great-fit opportunity. Like, I might be able to, in the future, simulate what it might be like to work at XYZ. WeWork for example - they may eventually be a client, which would be so cool, honestly…


…you know, to use your simulator to simulate the possibilities of working at WeWork. That would actually be such a cool thing. Call us when that happens.

Exactly. And the interview process is – obviously, everyone knows it’s broken… But one of the reasons it’s broken is the same reason that developer education is broken, is because it’s too focused on one specific skill - writing code. And I know amazing coders who are really bad developers, and vice-versa. Writing code is just not the most important skill. But that’s what you test in a job interview.

The issue though might be where you get this Instagram effect where the artifact for which you test against to consider the employment opportunity or the joining of a team may be flawed in the fact that it’s filtered. Like, who’s going to actually design a quest that is the perfect version? Like, they’re going to round the corners of certain things. It’s not going to be the unfiltered version of the company, let’s just say. I’m curious how accurate, if you get to that point, that that will be true.

Of course.

Maybe in that case you can hire an auditor or a third-party person… I’m just saying, somehow it won’t be accurate.

Now you’re just trying to increase my burn rate… [laughter] I need auditors, and all that. But seriously though, obviously, any–

I mean, auditor in terms of like somebody to audit the company to see how true it is, before designing it.

I totally get it. But obviously–

It’d be part of what they buy. It’d make money. This is a revenue-generating thing. I’m making products on the fly.

Every representation of a company is always somewhat falsified.

True, yeah.

I mean, falsified maybe is a very harsh word, but like you said, corners are being rounded. And the same goes for a video that they produce about working at Company X, right? So don’t blame the medium… It’s just another medium, and people are still going to, like you said, create that Instagram effect and make it look perfect.

Well, the one thing it could do accurately is simulate a stack, right? Because you point yourself to a repository, you pull that down, you install Docker, you spin Docker up, you go to a local host URL, you simulate chat with some people, maybe those are NPCs and examples of people, not so much people that work there… But you can simulate the stack and what it might be like. And it might even improve the dev setup potentially even. Like, pick out all the flaws. There’s a lot of really interesting permutations how this could work out, but…

I was thinking about it for that same angle, Adam, but from the side of the stacks. So this, of course, On, assumes that you have success, and there’s like this gravity effect, which we hope you get to, because it’s cool stuff, but…

I like that assumption. Yeah, I’m gonna take it.

Yeah, it assumes that. Let’s just state that as future reality. Imagine, now that you have this like in between, this engine that goes between technologies and games, quests… Well, you can have people write in the quests - of course, now you’re like Super Mario Maker, and that’d be rad…

Oh my gosh, yeah…

Or you can have people who have the technologies. Imagine a brand new startup technology like Deno, for instance… And they’re like, “Oh, there’s a Node.js track. We want people to have “real-world experience” with Deno. Deno is brand new, nobody has that yet… We have now a motivation to go ahead and create a Deno stack that you can plug into this game.” And now you can say, “Yeah, I went through Wilco, this quest in Deno, and I have six months experience” or whatever that would equate to.

[58:19] That’s true.

That’d be kind of cool.

Exactly. And we’re doing similar things. So if you go on our platform, you’ll already see quests that were developed together with New Relic. And those quests practice observability. Not just with New Relic tools, but mostly with New Relic tools.


And that’s an important –

Now Adam’s dreaming. I can see him dreaming over there.

Yeah, I am dreaming. I’m sorry. [laughter]

You got him!

I almost cut him off to throw in a dream, but I can’t do it. I’ll just be quiet.

Keep going on. I get to see Adam dreaming. You got him going. [laughter]

And that’s an important skill to have, right? Understanding how to instrument production, or even understanding that production needs to be instrumented is a skill of its own. And by partnering with New Relic, we’re able to do that. And yes, we can partner with companies that do their own tech stacks, or do their own database, or whatever it is. As long as you’re trying to get developers to use your product and to train them on your product, it definitely makes sense to do it on Wilco. I feel I feel like a salesman now.

What’s the closest thing we have in the technology world that is a simulator? Is there anything like that out there currently, aside from maybe like an ad-hoc version of something that might be like this? Like, a platform. This is a platform to do it. Or at least that’s the dream, the ambition that you’re driving towards. Some of these things will become true or not true, but is there anything that simulates any of this currently?

So there are things that try to be sort of a sandbox environment within your browser. But that usually ends up being very simplified, over-simplified, and is always designed to get you as quickly as possible into a function you need to write or rewrite. But it never actually gives you the simulation of a real system, let alone a real company.


We tried to look for something like that, and as Alan, one of my co-founders likes to say, if Wilco had existed… You know, we didn’t set out to start a company. If Wilco had existed, we would simply join it. But we couldn’t find anything like it.

What made you want it to exist?

For me, it starts in 2014. We were three co-founders, each one of us has their own journey that brought them to where Wilco is today, and eventually Wilco is the synthesis of this vision of three different people… For me, it started in 2013. I just joined handy as a VP of engineering, and we raised a nice seed round, but we didn’t have a lot of money. I was rather new to New York, and I didn’t have a strong network just yet… And we were just starting to build out our engineering brand. So I realized I’d have to compromise on something as I’m building my team, and I said, “Alright, I’m going to hire a team of the best and brightest, from the best schools, but they’re going to be inexperienced… Because they can write amazing code, so what’s the problem?” And guess what - like I said many times today, writing code is not that important, so I had to mentor them very closely. And at some point, it became unscalable. Luckily, by then I was able to hire more people that would help me with the mentorship burden.

But I reached out to a few bootcamps and I said, “Let’s do this evening class where we expose developers to simulations of real-world events. I believe that that way, within months, they can gain the experience of years.” All the bootcamps said, “We’re focused on zero to one. We don’t really want to do 1 to 100.”

[01:02:05.13] And then at some point, I moved back to Israel, and I tried it with Israeli bootcamps, and I heard the same response. And then at the end of 2020, I left WeWork and I called up one of my former colleagues, and I told him about this school that I’ve been meaning to open for a while now. And I said, “You know what, I’m gonna go for it as like a side project. I have a little time off, I’m going to do this as a side project.” And I had already called up a few CTOs, they all said, “This is great. We’re gonna send students your way”, and that former colleague told me that I’m stupid. So I asked him why, and he said, “Well you’re gonna have six, maybe ten developers per class. You’re not really making a dent in the universe. Let’s figure out a scalable way to solve this. And by the way, a third former colleague who’s a good friend to both of us is also thinking about the same space, so let’s get three of us to brainstorm and figure out how to solve this.”

We looked at everything that existed, and then we realized that everything is so top-down, and developers hate it. And we realized that there’s nothing that actually simulates all the warts and all. Not just the perfect codebase with a simple function that you need to write. We need to actually simulate all of the bad things as well.

And then we realized that it’s not about taking juniors from 1 to 100, but you don’t really have a way to practice throughout your career. Going back to the flight simulator analogy, it doesn’t matter how many years of experience you have, or how many hours of flight you’re logging every week. You still have to go through the simulator. And the fact that we don’t do it as software engineers is pretty crazy to me. And apart from not letting us advance, it’s also very demotivating.

I have a lot of friends who are senior engineers. They love the company they work for, they love the team, and they’re telling me, “I think I might leave.” And I’m like, “Why? You love everything about this job.” “Well, I’m not being challenged anymore. I’m not seeing anything new.” So I ask them, “Are you going to switch to a different company that you’re most likely going to like less than the company you’re in right now, just because you’re going to gain new types of experiences?” and they say yes. And this is somewhat tragic, right? What if they could have access to new scenarios without having to leave the team they love so much? What if they could continue to practice and become better at the same pace that they could become better when they just started out? That really guided a lot of the thinking behind Wilco.

Well, it’s this idea too of being able to mess up I think is kind of key, too… Especially in that scenario where you’ve got a senior who is sort of perceived by themselves as being stagnant in terms of their new experiences, and new learnings, and growth and whatnot. It’s this ability to do things, and mess up. And in a career, you can’t mess up, right? Like, if you mess up, you can not get your bonus, you can lose team members, you can lose trust, you can lose all these – there’s a lot of loss possibility in the real world, and I think the one interesting thing here with this is that you can have an area where you can actually mess up. And if I mess up in Wilco, what happens in Wilco stays in Wilco, so to speak. [laughter] And that’s a good thing. I think it’s the same thing for pilots. I would love my pilot to have so much experience on the simulator, and mess up so many times, because they learn all the things Sully did, which you mentioned… We’ve talked about Captain Sully before on the show, in terms of learnings… And it’s such an interesting thing of like what it takes to make those choices on the fly. And it was just all the years of experience, all the years of having these different scenarios… And even when trying to do it again, they couldn’t – there was a lot of speculation on the flight, and how the choice was made, and all that good stuff… All the most skilled pilots took the same simulation of the same crash and making different choices, and many of them crashed.

[01:06:14.27] Yeah. They never crashed in real life though, right?

Right. Exactly. That’s the point I’m getting to, is that it’s in a simulation, and so that’s okay. No one was hurt. But there was skills; you still upskilled. And we didn’t talk about Wilcoins; maybe potentially you’re also getting some true reward. I don’t know what you’re planning to do with the Wilcoin aspect, or… Jerod was saying “Is this Web 2 or Web 3?” Is it truly on a ledger? What is it?

Or Web 5. Web 5 is the new web.

Web 5, yeah. The new web.

Web 9. It’s three squared.

That’s how you raise money, is you just raise the number.

Yeah, exactly. Oh, you have to add .0 to make it sound cool. So it’s Web 5.0. Otherwise, it’s just 5… Who cares about 5, right?

There you go.

But yeah… You’re in a simulator, no one gets hurt, and there could be some reward.

Yeah. So Wilcoins are gonna have their fair share of ways to redeem for the really cool stuff. Even today, you can actually use them to buy hints. So when you tell Ness that you need some help, you might have to pay for that with Wilcoins. And that’s the difference between Wilcoins and experience points, because the experience points stay forever. It’s kind of like some airlines have the miles stay forever guarantee. But the Wilcoins are this stuff that comes and goes. You earn them, you use them…

The point is not to have – like, we’re not a social game that’s supposed to take all your money to buy fancy avatars or stuff like that. We’re not going to have you pay just to advance in the game. Our revenue stream is going to come from completely different–

You could pay for a certain quest though…

Um, potentially… But –

Like, you’ve gotta have enough experience points and have enough coin to go on a certain quest. Because that would motivate me to 1) be immersed longer if I’m really enjoying myself. I’ll want to upskill to get there… And I’d want to make sure I have a bank account that can support my quest habits, so to speak. [laughter]

So gaining enough experience points to gain access to a quest is definitely something that’s going to be in the platform. Having enough Wilcoin is an interesting question, and like I said, this is not the revenue stream we’re planning on. We would much rather have teams that are genuinely interested in becoming better as our customers.

And we think it’s a great value proposition to those teams. But Wilcoins are going to be this great bonus for you to do really cool stuff in the game, and maybe get some Wilco swag.

I was gonna say… You’ve gotta bring some of that into meat space, and get us some T-shirts and stickers and stuff… Being able to trade that stuff in for something that’s real is – that’s just fun.


And fun is at the core of what you guys are trying to do, right?


True, yeah.

In the future, we might have specific pieces of swag for specific achievements in the game.

It’d be cool. That’d be cool.

You could be like one of only five people in the world to actually have that piece of swag.

Now I want in.

That’d be cool. Limited edition.

Ooh, when you write your first changelog, then you get a changelog T-shirt.


But only the first five people that write a changelog… [laughter]

I was thinking back to that colleague of yours who told you you were stupid for this idea, and the size of the impact, right?

He’s my co-founder now, you know…

Co-founder, okay. There you go. That completes the story. So we obviously – when we put our best work out there, impacting a few you can be deflating in terms of your motivation… And so the larger the impact, positively, is a net positive for the world. And I’ve gotta imagine that at some point you might be able to interface with, let’s say, like – not so much bootcamps themselves, but those who truly care about educating the future generation of the world’s hackers, of the world’s engineers.

[01:10:24.01] I have good friends in the space, Launch School, and Chris, and others that do this stuff; they care deeply. Is there a world where these two intersect? Or are you competitors with them? Are you parallels to them? How will those who are educating – can they play? Is this a world they can be involved in? Is there room for them?

I think these two things are very complementary. So if you want to upskill, if you want to practice what you do, you need to know the basics to be able to start doing that. You can’t start going on Wilco unless you actually know the programming language. Now, you don’t need to be an expert in it or anything like that, you just need the basic knowledge of it. But if you don’t have that, you’re not going to be making the most out of Wilco. And I really think that you need this combination of knowledge and wisdom to be able to create real proficiency, right? And what we try to do is give you that wisdom. Whereas what the other schools are trying to do is give you that knowledge. And it’s not that one of them is more important than the other. You really need both. Being complementary goes both ways, right?

I think that a lot of these, let’s say, bootcamps could really benefit from sending their students to run quests on Wilco, play quests on Wilco once a week, or something like that. But I also think that Wilco players could benefit from a class after having played a quest and realizing that maybe a specific skill is something they need to work a bit more on. Or maybe they’re actually missing the very basics of that skill, and they could go take a class somewhere. So to me, these two elements need to live together for our industry to really get better.

As you were describing that, I was thinking about one of my most favorite games ever in the world, and it’s the original Castlevania from NES, way, way back in the day. And like any gamer or anybody who really enjoys a game, you don’t just play it once. You don’t just go and quest all the way to Dracula, if you can ever get there, or Medusa, or these other folks, bosses that are along the way. I’ve played those levels numerous times. Sad to even say, I’ve also watched others who are really good at playing that game get their best time ever on YouTube, or on Twitch, or wherever. I’ve watched the world record holder, for example. And so I’m wondering if in the future you’ll have people who go back and play a level again to get even more sharp. Practice makes perfect, right? Doing makes perfect, so to speak. So I wonder if this is a thing where you might enjoy what you do so much you go on a quest once a week, but it’s the same quest every single week, you just get better and better and better.

Yeah, definitely. Athletes continue to do the basic drills all the time, right? The fundamentals matter. And for me, it manifests itself in two ways. First of all, you’re absolutely right, and there are games like SimCity, for example, that I could play forever. And the more open a game is, the more it makes sense for you to play it again and again, because you can do things differently, and you can try various strategies to winning it. And then in some city, if you manage to get everything in those domes, eventually, or whatever they’re called, then - you know, jackpot. But there are different strategies to go about it.

[01:13:59.16] So you could play the same quests again and again and again, and try to do different things, but in the future, we also think we will have multiplayer quests. And then at some point, you might play that quest again, but as a different character within it. So maybe the first time you played it, you were the engineer responsible for a specific element of it. But then the second time you played it, you’re actually taking a very different part, and doing something completely different. Maybe the first time around you were doing the backhand and the second time you were doing the UI for it, or–

Right. Like roles, yeah. That’s interesting. I was thinking of it in a similar vein to you, which is like the anti-player. So you might be doing a class - and correct me for how accurate this may or may not be… In the future you may be doing the quest, but I’m the person who’s the opposite role, which - I take production down, and your job is to keep it up.

[laughs] Yeah.

So the quest is for you, really, but I’m the anti player. I’m QA, essentially. I’m taking you down…

Yeah, adversarial mode. Yeah. I love it.

…which kind of gives a different facet to it.

One of the passive-aggressive coworkers.

Really, really interesting. I mean, there’s a lot of possibilities, probably so many that we can just keep talking through all the different permutations… But one thing you said in regards to Wilco was “That’s not our business model” and you kind of alluded to certain things. What exactly is the business model you’re building? You got funding, you were on TechCrunch, you were covered on that… So this is a funded startup, you’ve got runway, you’re making a dent, or you’re attempting to… What is the business model, and how will you succeed?

So you said making a dent, which to us is more important than the business model. Eventually – it’s very cliché, especially coming in from WeWork, but we are a mission-driven company, and our mission is to empower every developer, regardless of their background or skill level, to unlock their full potential. And if we do that, I think we’re also going to do really well from a business perspective. Because if you provide real value, people are going to want to pay for it, right?

But teams do have learning and development budgets already, and they, in many cases, don’t know how to use them. So you could be sending developers to conferences, you could be buying online courses for them… But everything is very ad-hoc, everything is dependent on someone finding a good use of that budget. Whereas what we’re saying is, “Hey, just get a Wilco subscription for your team members, and they’ll be able to practice all the time, whenever they want, at their own pace.” And the platform is going to have enough content that they can choose what they want to become better at. And you’ll actually know what they become better at as well.

I guess you could even say like a manager, or somebody can motivate them by saying, “Hey, take that quest again this week. I would love to see how you do that quest in this role, with this concern.” Is there gonna be that kind of lever involved? Or is it sort of like very hands-off to that person to make their own choice to do the quests whenever they want (or the quests) and it’s very a-la-carte to them? Or is it sort of guided, to some degree? Like, what do you have planned for teams?

So it’s a mix of both. But when we say guided, to me the most important aspect of it is I’m a manager, and I want to know how to help my team get better at their job. So this isn’t about grading, or anything like that. Not that I think that software engineers could be graded. If I did know how to grade them objectively, that would probably be a company of its own. But I do want to help managers be better at their job as well. And if I’m having a one-on-one with you, Adam, and I can tell you, “You know what - I think you’re doing really well on databases, but everything frontend-related, it seems like you’re stuck… So why don’t we figure out some ways to help you? Or maybe we pair you with Jerod; he’s doing really well on frontend, but actually needs some help on databases… So why don’t the two of you pair for a while, and kind of try to rub off each other and help each other out?” So that’s another tool in my arsenal as a manager to make my team better as well. But it’s not about me trying to decide the path for them.

[01:18:28.22] I almost see it too, like “When was the last time you simulated a database failure? Or when was the last time you simulated production being down because of an unknown error that you have to investigate?” And you might actually –

It’s crazy that we don’t exercise that all the time, right?

Well, that’s where I really see the sweet spot for this. Because if you leave it up to the individual - sure, I want to upskill myself, but I’m also going to be lazy. Any developer is going to be lazy. That’s just a natural artifact of just being human. But if I have somebody who cares about me and the direction I’m going, and I’m at a company who truly cares about me, and someone says “When’s the last time you stimulated this?” or – it’s just maybe almost mandatory, even… Like, simulate failure of some sort that matters to you, and pick your own version of failure, and correct it. That’s going to make me better at my job; it’s going to make sure that my company performs well, it’s gonna make sure my product gets bought by people, it’s gonna make sure that my bonus is there when it’s time to collect it… On the quarter, on the year, my RSUs actually get to be cashed in. Like, these are things that you care about when you’re in a technology company. And if you can simulate those things and be better at those, I feel like it’s sort of necessary if this is an existence in the world. If this thing exists, then it should be something people can do.

Yeah, I absolutely agree. And going back to the beginning of what you’ve just said, I find it crazy that we don’t practice on a regular basis. Can you think of an NBA player who doesn’t practice free throws every day? It’s nuts, right?

Check out Kobe. All the documentaries on Kobe, and –

Shaquille O’Neal? [laughs]

Yeah, Shaquille is a different –


But yeah, I mean, you’ve got to put the hours in, you’ve got to put the practice in?

Well, going back to your mission, real quick, I just want to say that as somebody who’s been in the field for a long time, I appreciate the part where it’s like for every person or every developer, no matter where you are in your career, because a lot of these tools and educational resources, as somebody who’s been in the business for a long time - I’m never their audience. And the fact that as you sign up for Wilco and the onboarding experience is like “Where are you in your career, and what are you interested in upskilling?”, the fact that I have an answer there, and I don’t feel like I don’t belong here is awesome. Like, “Oh, actually, just because I’ve been doing this for a long time doesn’t mean I don’t need to simulate some stuff, or learn something new.” And I think it’s very welcoming to expert-level or long, long-careered people. I think that’s really awesome.

Long-careered people. I love that.

I don’t wanna call myself an expert, but I’ve been around the block a few times. I don’t need the beginner level content, but I still need and desire to get better at certain aspects, right? So I think it’s cool that you all are providing resources for us, in addition to people who are just getting started.

Yeah. It started, like I said – back when I first thought about it, it was just “How do I make these very junior developers better, and how do I help them gain experience?” but then we realized that the problem is even bigger for the more seasoned developers… Because for them, it’s really hard to find new types of experiences.

Well, On, thank you so much for sharing this story with us, and sharing I guess a glimpse into even your experience at WeWork, too. This is a first for us, to kind of – I mean, it’s an elusive type of company, and all the things that happened there, the TV show… A lot of interesting things, but getting a glimpse behind the scenes, just a little bit, was interesting. All the technology, the invisible technology that made it work, and then also how that translated into just how you’re working now and you care about every developer, no matter where they’re at. I think that’s such a cool story, so I appreciate you sharing, I appreciate –

[01:22:20.25] Is my version better than Anne Hathaway’s and Jared Leto’s? Or you don’t think it’s gonna get picked up…?

I’m three episodes in, so I’m not a full WeCrashed watcher yet. I’m on my way. But Jerod, I think he has completed the series.

Final question, who would play you in the Wilco straight to fiction Apple TV+ dramatized version?

I don’t know, maybe I have aspirations as an actor, and I could play myself.

[laughs] There you go.

Keanu Reeves.

Yeah, Reeves. Nice. [laughs]

Ooh, that’s actually a pretty good one.

Yeah. And you can also throw in some Kung Fu, and that would be really amazing.

That’s right.

It would turn into this actual ninja.

That’s right.

No, but I actually – I was told once that I look very similar to Andrew Garfield. That was when I had shorter hair, so maybe he would play me, I don’t know.

I’ve only seen the longer-haired, pixelated version of you that I see here on recording, but I was actually just starting to think a younger Shia LaBeouf. Like, not Shia LaBeouf now, but like maybe a few years back.

How old is he?

You’re probably older than he is, but he’s changed his look up recently. [laughter]

Well, he’s got more scruff, for sure.

He’s gotten scruffier.

I don’t know, throwing it out there. But I think Keanu Reeves would be sweet.

I would almost say Adam Driver even, especially here on camera today right now. Adam Driver, yeah.

Adam Driver… Oh, why?

Good actor.

Interesting. Why? Are you typecasting because I’m Jewish? No, just kidding. [laughter]

Is he Jewish, too? No, not at all.

I’m just kidding.

I didn’t even know Adam Driver was Jewish.

Me neither.

Learn something new every day.

But he looks similar.

Yeah, I would love to have Kylo Ren play me. Come on, that’s, that’s awesome. And we could have like a lightsaber–

That is actually a good pick. I don’t know though, Keanu Reeves? A little bit better…

So maybe Keanu Reeves and Adam Driver can both play… You know, we’re three co-founders. Both of them can play, and we can have like a Neo versus Kylo Ren scene at some point…

Just for fun.

Because what tech company doesn’t have that going for it, right?

And then randomly Shia LaBeouf comes on and just starts yelling stuff. [laughter] “You can do it! You can do this! Just do it!!”

I actually prefer Rob Schneider’s version of “You can do it.”

I’m not familiar. I’m gonna have to go look at that. Oh, “You can do it” from Waterboy. “You can do it!!”


Now I’m with you. I thought he made fun of Shia LaBeouf.

A meme as well…

So I think there was like a period in which every Adam Sandler movie had Rob Schneider come in and say “You can do it!” at some point.

And that’s like his only line in the whole move, pretty much.


[01:25:02.20] “You can do it…!”

The website is a .gg, right? No, it’s trywilco dot c-o-m, which is .com. I don’t know why I read it “dot c-o-m.” So weird. [laughter]

It’s t-r-y… No – [laughter]

HTTPS, colon, slash-slash…, you’ve heard it here first, .com. Check it out. Number one on Product Hunt. “Never stop developing”, a fantastic tagline, and pun.

Yeah. And guess what - by the way, if you go to, you’ll actually get access that cuts the waitlist and you’ll be able to get right in, at least the first few.

Oh, nice.

I see you’re trying it now. It’s not up yet. I’m assuming there’s going to be some time until this thing actually airs…

No, this has been live the whole time. We didn’t tell you…?


I do enjoy the 404 page. Hopefully our listeners will not see that. It is cool, though.

No, they won’t. It will be out by the time they get to it.

Okay, excellent. So there you go,, or dot c-o-m, whichever you prefer, /changelog to - I guess jump the waitlist… Is that right? Jump the line?


Fantastic. Fantastic. And while you’re, there upskill. Simulate. Practice.

Never stop developing.

Get better. Be a better teammate. All the things. On, thank you so much for your time today, and sharing all you’ve done. Really appreciate it. It’s been awesome. Thank you.

Thank you so much. I had a great time. Thank you.


Our transcripts are open source on GitHub. Improvements are welcome. 💚

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