The Stack Overflow Podcast

A flight simulator for developers to practice real world challenges and surprises

Episode Summary

On Freund was one of the minds behind the scenes of the now-iconic WeWork startup story. He held three roles at the company: VP of Engineering, VP of Product, and Global Head of Markets at WeWork Labs. The software his team built demonstrated rigor, engineering grit, and strong logic. It’s the reason why WeWork is, at its core, a tech company. Now, Freund has entered into a new season of his career as co-founder and CEO of Wilco, which is a platform for developers of every skill level to advance in their talents and career journeys. Like a flight simulator, it offers challenges that are meant to prepare developers for the realities of what they will face on the job, moving beyond what they might learn in a classroom or boot camp to scenarios taken from real workplace experiences.

Episode Notes

Freund reflects on his early days at Applied Materials, where he worked on a machine that inspected silicon wafers.

It was in this early role that Freund gained an appreciation for rigorous software testing protocols in the manufacturing process.

At WeWork, Freund was fascinated by the idea of a full stack business, which is a business building itself.

While Freund officially launched Wilco in 2021, the origin story for the company dates back to 2013 when he was hiring and managing a team of engineers—he saw a need in the market to help developers build critical skills to problems-solve in real-time.

You can think of Wilco as the equivalent of a flight simulator for engineers.

Shoutout to Lifeboat Badge winner Zico for their awesome answer to the question, “Hiding sensitive information in response

Follow On and Ben.

Episode Transcription

[intro music plays]

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BP Hello, everybody. Welcome to the Stack Overflow Podcast, a place to talk all things software and technology. I am Ben Popper, Director of Content here at Stack Overflow, and I am flying solo today but I have a great guest, On Freund who is the ex-VP of Engineering at WeWork, and now the CEO of a company called Wilco, which is focused on upskilling for devs, giving them hands on experience through simulated real world engineering challenges. We talk a ton on this show about developers' need for learning and growth and development and how important that is for them in deciding what job they want to take, so we're excited to have On on the program. On, welcome. 

On Freund Thank you so much, Ben. Great to be here. 

BP So the first thing we do when we start is we always just ask folks to tell us a little bit about how you got into the world of software and technology. What got you started as a kid coding and what led you to sort of your early career? 

OF Sure. So I must have been something like six or seven when I wrote my first line of code. It was in Basic on an IBM-XT, and we had an XT in the house which was not common and I was just fascinated by what could be done with it. And I wrote a few lines of Basic with the numbers at the front. You had to do like 10, 20 to leave spaces for other lines of code to get in between, and just started doing things and ever since then I've been loving it. 

BP Very cool. So did you study computer science or engineering at university or did you go straight into working? 

OF I did study computer science. I worked in tech after high school for a bit just doing customer support and things like that. But just like any Israeli, I joined the IDF, and then after I completed my service I went to Tel Aviv University and studied computer science. And about halfway through the degree I got my first job at a real company, that was Applied Materials. I was there for about a year and then I realized that I belong in the startup world and I didn't look back since. 

BP Very cool. So for folks who don't know, we've had some other guests on from Israel. There is sort of this amazing pipeline from doing the compulsory military service to learning technology and cyber security to going into the startup ecosystem which is quite rich in Israel and I guess specifically Tel Aviv. Do I have that correct? 

OF Yeah, you do have that correct. But that's not the only way to get into tech. So even though I was in a good place in the army, I did not work with anything having to do with software. But like we said earlier, I did study computer science after that and that sort of helped me land my first job. 

BP Gotcha. And you said you worked at Applied Materials. That's like actual hardware, semiconductors, stuff like that? 

OF That is hardware and semiconductors, but I worked on this machine that would inspect the wafers in the manufacturing process to make sure they have no defects and to measure the distance between two conductors and things like that. So it was really cool. It was connected to an electron microscope and lots of hardware that was just moving wafers around, and everything would crash every once in a while. It was a pre-production system. It would crash and sometimes it would break a wafer. 

BP Were you working at the embedded level there? You were kind of working close to the metal?

OF So most of the code was C++ algorithms for image processing, but then the application layer was C# so I did a lot of that, .NET, C#. Yeah, that was fun, but when everything you do breaks a wafer and then you need to it vacuum and it can take like two hours for the machine to spin up again, you really learn how to be very careful with what you do. 

BP Right, got to have some extra testing before you push that to production. So yeah, that was your early career. Talk to us a little bit about the role I mentioned. You were a VP of Engineering at WeWork. That was an incredibly fast growing company. I'm sure there were lots of people being hired and lots of different ideas about things to build all at once. How did you find yourself in that role and what was it like to work at one of those rocketship type startups? 

OF Yeah. WeWork was fun, boring, nothing out of the ordinary happened. It was all just smooth sailing.  

BP Very calm, boring CEO, always behind the scenes. 

OF Exactly. So at the time before joining WeWork I was at a company called Handy. We were doing home services on demand. And I was fascinated with the idea of WeWork and I had a few friends working there and at some point I decided that I wanted to leave Handy and after that I pretty quickly realized that WeWork is the place for me. What was cool about WeWork was that it's what I call a full stack business, meaning technology is building the business itself, not some shrinkwrap product that you're then selling. You're actually building that business. So maybe a great analogy would be that there are two ways for you to be working on software for clinics, let's say. One way is that you could be working for a software company that is building software for clinics and selling it to clinics. And then if you're asked how much the company is selling, you probably have no idea, and how it's selling is also something that you probably don't know. But you probably know a lot about doctors and patients and nurses and the ratios between them, et cetera, et cetera. Another approach would be the company that actually is owning clinics and operating them at a high scale using software. And when you do that it's really cool because then software engineers are actually very aligned with the business. They know what's happening. They know how the business is running. And I found that to be really cool and that's true for WeWork, it's true for companies like Amazon and Uber and Airbnb and a few others. So I really like that model. We were building software that was basically running a thousand buildings around the world and that was really cool. 

BP Right. I like the idea that you're building software but also you understand how that's going into operations, how that's affecting everything from real estate, to the way people are getting reservations for rooms, to the way people are booking events. And WeWork introduced a new category for this kind of flexible on demand office space which now we're seeing a lot more of. I guess one of the things I find fascinating and I would love to ask you is, you mentioned what a ‘boring’ company it was. It kind of struggled its way towards the IPO at the end, but fundamentally it feels like the thesis was correct, or at least post pandemic the thesis was very correct. I myself have moved to a co-working space. Many people I know are moving to a hybrid system. It really feels like the vision at least is much closer to what work looks like today than it was 10 years ago or something like that. 

OF Totally. And when I joined WeWork, one of the criticisms we would keep hearing is, “What's going to happen in a downturn? You're going to be stuck with very expensive real estate and you won't be able to do anything with it. No one's going to want to come to WeWork.” And we always said, kind of like how Bane was born in chaos– Bane from Batman, WeWork was born in a crisis. The seeds of WeWork were started in 2008, and then WeWork was started in 2010. So we always thought that it's not actually going to be a problem. During a crisis you'll actually see more people becoming freelancers and wanting to work out of a place where they can actually meet people. You'll see new businesses popping up. And you know what? Covid was probably the worst nightmare you could think of for a company that's doing shared spaces, because Covid was a problem both from the space perspective and the shared perspective. It actually targeted both aspects of it. And guess what? Yes, occupancy went down, but it didn't go down that significantly. And the expense of real estate was actually easy to restructure or make more profitable when we did it. So in a way we were vindicated. Not completely, it's not as if the company has lived up to its crazy valuations during its heyday. But I think the fundamental business model was vindicated.  

BP Yeah. And what's interesting is my experience of WeWork early on was, “Oh, this is for small startups or solopreneurs or people who need space that don't have a traditional company.” Now post pandemic, a lot of big companies with a remote and a distributed workforce are getting these subscriptions to a WeWork so that all their employees, whenever they feel like using an office, can go into a WeWork. So kind of interesting how the model has almost flipped on its head where large companies now want to avail themselves with that.

OF I actually remember mid Covid, I can't say the name of the company, but there was this one company who paid an exit fee of I think $90 million to get out of its current real estate lease and join WeWork. 

BP Wow. Yeah, I'm a former New Yorker and I've written a bit, living in New York City, a bit about the challenge that's facing cities fundamentally if they can't refill those commercial office districts. They'll have to transform them into something new because they made up such a big portion of the city's lifeblood, its tax revenue, its daily commuters and everything like that. So tell us a little bit about your decision to leave WeWork and create something new and then what was the sort of genesis of your new company, Wilco? 

OF Yeah. So I left WeWork at the end of 2020 and I was actually joining a VC firm for a while, I did that. But the origin story of Wilco starts way earlier. So in 2013, I joined Handy and I recruited a team. A lot of them were recent grads or people who just graduated from either a boot camp or university. And I thought I was going to hire the best and brightest and they'll be amazing engineers. And in a way I was right, but I was also wrong because those really smart people were great code writers, but they weren't necessarily great engineers. Because if you put them in a team, they don't know how to act in a team setting, for example. And if all of a sudden they have to maintain a production system, that's something they've never done before. But if you put them in a function and you say, “This function should be doing this and that,” they will write amazing code to get you there. 

BP Right. In a vacuum they can operate, but on a team it's a little bit different you're saying? 

OF Exactly. Someone once gave me a great example. He said that if he wants to understand the state of the art in medicine, he's going to go to a recent med school grad. But if he needs someone to operate on his shoulder, he's going to go to a surgeon with 15 years of experience. And it feels kind of the same way in engineering. If you want to get the smartest solution to a coding problem, you want to go with a recent grad. But if you have a production system to maintain and a software development life cycle– 

BP Go with the grizzled experienced engineer.

OF Exactly. So I was trying to figure out ways to get them to gain that experience really quickly and I reached out to a few boot camps and I said, “Why don't we create this sort of evening school where they get exposed to simulations of real world events, and that way within months they'll gain the experience of years.” And all the boot camps said, “This is a great idea, but we're not going to do it because we focus on zero to one and what you're saying is one to a hundred.” So in 2016 I moved back to Israel and I tried the Israeli boot camps after the New York boot camps wouldn't take the bait and I got the same response. And then in 2020, I left WeWork and I said, “All right, this is it. Even though I'm joining a VC, I am going to run this as a side project and I'm going to find someone to actually manage the daily operations.” And I spoke to a few CTOs and they all said, “Great. We're sending students your way. This is amazing.” So I reached out to a former colleague of mine and I told him about this idea and I wanted to get him involved and he told me I was stupid. So I went ahead and asked him why and he said, “Well you're going to get a class of six, maybe 10 students if you're lucky per semester. You're not really making a dent in the universe. Let's figure out a scalable way to solve this. And by the way, another mutual friend of ours is thinking about the same space so why don't the three of us get together and brainstorm?” And that's how we got together, the three co-founders of Wilco, and we started talking about this and we realized that this is bigger than what each one of us thought initially. So I came with my idea, and my co-founders came with their ideas, and we realized that this is not just about taking recent grads and giving them accelerated experience. There is actually a bigger problem in tech, which is that developers don't have a way to practice. The only way to practice is on the job. But what happens when you practice on the job? First of all, it's very slow. It's going to take you years to gain the initial experience, and after that it's even slower because the more seasoned you are, the less likely you are to combine new types of scenarios. B, it's very error prone. People make catastrophic mistakes. And C, it doesn't provide equal opportunity because too much depends on the mentors that you get access to and the type of workloads that you're having in your team. Do you get exposed to production often? How often do you touch design rather than just write code? And so many other factors. And then another thing we noticed is that everything else that has to do with training of developers is usually top down, and developers hate it. So we thought to ourselves, “All right. We're looking for a way for developers to practice and it has to be fun.” And we said, “All right. What do other domains do?” And the best example that we came up with was aviation and flight simulators, and we said, “All right, why don't we create the equivalent of a flight simulator for software development. What would that look like?”

BP Right. You kind of mentioned that you wanted people who had sort of been in the fire. If you were to say a surgeon, they've been there, done that. If something goes wrong in the surgery or they find something unexpected, they know what to do. Flight simulator, same thing. You can simulate a flight that's going perfectly, but then you can introduce some variables. Oh, what if this engine goes out? What if the landing gear doesn't deploy? So when you are offering this to users now through Wilco, how do you stimulate the idea of being a working engineer on a team and what are some of the different variables and challenges you can throw at them so that they can learn?

OF Yeah, so I think what you said makes a ton of sense and I guess the best example is when you need to land on the Hudson, nothing is going to prepare you if you just fly regular flights, right? You need to get on that simulator and try out different things. So we started doing that for software engineering and the obvious place to start was our pasts. And we said, “All right, what are some interesting scenarios that we thought were really important in our professional development?” And we started building on those. And then we said to ourselves, “All right. Why don't we take every type of scenario that happens to us and turn it into a quest?” So if you think of the life of an engineer, one of the things we love doing, or at least love to say that we're doing is postmortems, right? Something happened, good or bad, we analyze what happened, we try to make it blameless, try to come up with interesting lessons to be learned and implement it in the future. And then the product is a document that probably no one is going to read. A week after the document was prepared, no one else is going to read it anymore. Hopefully the lessons were also logged in some sort of ticketing system, which means they might be learned, but that's it. What if instead you would build a quest and actually allow every person on the team, whether existing or new people joining, to just experience that scenario again and come up with what they would do differently or some of the things that worked well but also some of the things that didn't work well. And if people actually experience it, then lessons are really internalized. So that was our approach to building everything so far. 

BP Nice. So if there are developers listening and they want to go check this out, they want to see what it's like, what's the best place for them to get started? 

OF They go to and they get to try Wilco. And signup is free for the Community Edition and you can try it out. Of course we recommend getting your entire team on board and really making use of some of the advanced features that we have there. But if it's just for your own personal use, go ahead and sign up on the website.

BP Very cool. All right, everybody. If you're listening and you want to see if you've got what it takes to pass some of these quests, or you want to get some new skills by trying out some sort of simulated real world experiences, try Wilco. That's really cool. One other thing I would ask before we end the show is what to you are some of the funnest and most exciting challenges you have there? I'm sure you have lots, but for folks who are listening, what are some that you would recommend, do you think are particularly interesting, and are they drawn as you said from people's real world experiences?

OF Yeah. Some of them are actually drawn from Wilco experiences, which is really cool. We encounter a problem and then we say, “All right, let's turn this into a quest so others can play it.” One of the quests that I've seen to be very popular is the one we call ‘Search Party’, and it's all about taking your application and adding search functionality to it. I think people like it because search is first of all, one of those things that is cool. As a user you immediately get to see the result of what you've done. And it touches both the front end and the back end and it just lets people go wild. And especially on the front end side, you can decide what it looks like and you have sort of the requirements from the product and design team, but you can take your freedom within those guardrails. So people really like that one. I'm a big fan of all of them. We have one that I think is really awesome but it's one of the toughest, which is data seeding. A lot of people get stuck into it. It's where you're supposed to seed your database with information so that new people coming in would have that script available to them as well, so they can see their local database. The type of thing that you would encounter on your first day in a job. And that's one that's been really hard, so if people are looking for a tough challenge, I would say go for that one. And we have some cool quests together with New Relic, for example, where you can test your observability skills and touch not just the code, but the whole understanding of how you even know that something's wrong in production, the tools you have to investigate it, et cetera.

BP Right, okay. Very cool.

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BP All right, everybody. It is that time of the show. I want to shout out someone who came on Stack Overflow and help to spread some knowledge. Today we are shouting out Zico, who was awarded a lifeboat badge for providing a great answer to the question, “How do you hide sensitive information in a response?” All right, if you want to know how to do that you can check it out in the show notes. And appreciate you Zico for coming on and giving an answer and spreading some knowledge around the community. 

OF Awesome work, Zico. This could be a quest. 

BP This could be a quest. Yeah, exactly– How to hide sensitive information in a response. All right, everybody. I am Ben Popper. I'm the Director of Content here at Stack Overflow. You can always find me on Twitter @BenPopper. Email us with questions or suggestions, And if you like the show, leave us a rating and a review. It really helps. 

OF I'm On Freund. I'm a Co-founder at Wilco. You can always go to to try us out. You can find me on Twitter. You can find me at my home, but that will be weird so Twitter is probably best. 

BP What's your handle on Twitter? 

OF @OnFreund. 

BP Very cool. All right, everybody. Thanks for listening and we will talk to you soon.

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