Giant Robots Smashing Into Other Giant Robots

449: Welcome, Will Larry!

November 17th, 2022

Will Larry, Software Developer at thoughtbot, joins Giant Robots as host! ๐ŸŽ‰

Will talks about how he got into tech, how everything is going so far at thoughtbot, interviewing at thoughtbot previously, but not getting the job, and why he decided to interview again (and snagged the job!)

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CHAD: This is the Giant Robots Smashing Into Other Giant Robots Podcast, where we explore the design, development, and business of great products. I'm your host, Chad Pytel.

VICTORIA: I'm your other host, Victoria Guido. And with us today is our brand new third co-host, Will Larry. Will is a React and React Native developer at thoughtbot. And we're so excited to have him join us as a co-host of the show.

CHAD: Will, thank you so much for joining us. Congratulations and welcome. Woo-hoo.


WILL: Thank you for having me. I'm excited.

CHAD: Will, I was so excited when I put out the call for people to join as co-hosts, and Victoria raised her hand, and then you did as well. You were on parental leave when all that started to happen. And so congratulations again on your new family member, and I'm glad we could finally have you join us.

WILL: Yeah, I was excited about it. When I thought about joining, there are two things that came about: the excitement of joining and just the fear of it.

CHAD: [laughs]

WILL: And I was like, I need to do this. I need to do this because it will make me better. So I'm excited to be here.

VICTORIA: That's a lot of change to navigate in one year, Will. [laughs] How's that got going for you, and how's everything so far in your first time here at thoughtbot?

WILL: Yes, change, change, change, that's what has been this year. I changed and started working at thoughtbot, our third kid. This year, we moved to Florida, just a lot of change. But I've learned along the way that change is life, and so we just embraced it. And I'm hoping that we're kind of settling out a little bit, but it's been good. It's been great for our kids. I think they're ready for some consistency and just the same thing over and over for a little bit. But it's been good. And we made it through. We're on the other side.

CHAD: Was there a grand plan to all the change? Like, did you have everything planned out in advance? Or did it all sort of just happen one thing after the other?

WILL: Yes. If you know anything about me, I'm a very big planner. My wife, my spouse she is the one that pushes me to be more spontaneous, but this was too big to be spontaneous, so it was definitely planned. It actually got changed. We were supposed to move in September, but with the birth of my son, we decided to move it up and move sooner.

VICTORIA: Right. I'm going to ask you the same question but about your career. So you made a big change from operations into mobile development, and was that part of a grand plan, or did you happen upon it? How did you make that change?

WILL: That change was kind of out of desperation. I was in operations working for a nonprofit; I loved it. My spouse was working at the same company, and I was a promotion ahead of her. It was an amazing opportunity. But the teams are so small that we couldn't be on the same team. So they had multiple locations throughout the country. And you don't have to step off the team, but if she's going to take this promotion, you have to step off the team. There potentially is a way that, down the road, you can come back.

And Katie is my spouse. She has been so supportive of everything that I've ever done. And I just felt this was a time, a great time for me to show that I support her in everything she did. But it was probably one of the toughest times in my life. I didn't have a job. I thought that I can easily jump back into it and find a job. I ended up working at a clothing store, which is not my strong suit. I really struggled working there. I think I worked there a month, and I was like, I can't do this. And then, I went to work at a different company, a travel insurance company, and so I would process the data.

I was miserable, and that's an understatement. I was so miserable. One day my spouse came in, and she said, "Hey, we got to change this. You're not doing well. Let's dream a little bit." And normally, that's not my personality. Normally I'm like Xs and Os. I know what's coming. And I was so out of it. I was like, let's do this. And she asked me a couple of questions. And one of the questions was, "If you could do anything, what would you do?" I thought about it.

And I came from a small town in Louisiana. And I never had the opportunity to work with computers. It was just the resources weren't there. And so that was one of the things I said, "Hey, I want to work with computers in any way that I can." She was like, "Go figure it out, whatever it takes." And then I told her I was like, "It's going to cost some money for me to do this," because I went to bootcamp. And she was like, "Go do it. Let's invest in you. Let's make this happen."

I ended up going through the bootcamp and came out on the other side. Interesting story; it's interesting how things come back around. My first interview was at thoughtbot. I bombed it. [laughter] I wasn't on thoughtbot's team at that point. But the way that it was handled, I got a glimpse of the culture.

I remember walking out that day and saying I'll be back. I will be back to be a part of this company because I bombed it. But they still spent time with me explaining things, teaching me the things that I bombed. And so I was like, wow, that's what I want to do in this field. So yeah, that's how I got into development. Here I am.

CHAD: Was there anything that surprised you about development, about the tech world?

WILL: Yes, yes. I think the biggest thing was the growth in development. So in any of my other jobs, I was able to take in expectations and make a plan and, like, okay, check off. I can knock that out and be successful. And I tried that in development, and every one of my bosses would say, "Slow down. It takes time. It takes time." And I just didn't realize how long it would take for me to grow in my coding skills.

That was the biggest surprise for me because I just couldn't come through, and okay, I got it, let's go. Because I'm very big on I know my expectations, okay, I can meet those expectations, and then I'll go over and beyond. But I couldn't do that in this field. And I think that was the biggest surprise for me that I couldn't just show up at work and do my task and still be a great developer.

VICTORIA: Right. And I love that you're sharing that story. Because with the people I've worked with at Women Who Code, it's a very common struggle when you're starting out in your first time as a developer and getting comfortable with being not great for the first six months or a year, or however long it takes. And I think that it's important to share that and make sure that other people feel the same way. And you might feel that way for a long time and maybe forever [laughs] if you keep switching up your roles in tech.

WILL: Yeah, definitely. And it was a very humbling experience also because, in most of my other jobs, I was the leader. I was the person that had direct reports and leading people. But in this job, I started at the very bottom. I remember there were days when I couldn't even get through my tasks and had to really lean on others to help me through it. You know, my senior developer, I was like, "Hey, it's that time. I got some questions for you." And so, I had to learn how does Will learn and what's the best way for me to excel in this field? The things that I've done before, I couldn't do it going forward.

CHAD: Bootcamps are pretty popular. And they are an avenue that certainly didn't exist when I was learning. You said when you were having the conversation with your wife that it sounds like that was just right there as the path forward. But did you consider an alternative path?

WILL: Yeah. So at that time, I felt like there were probably three paths: there was the bootcamp, there was the college degree, and there was the self-learning path. So the college degree, I thought about it because, at that time, I felt like a lot of companies were still like, hey, you have to have a degree to be hired and be a part of it. So whenever I thought about going back, I didn't know if it was going to cut me off from other jobs, so that was one of the reasons why I really decided, or I really thought about going the degree route.

And I decided against it because I did a lot of research, and there were companies at that time that were like, you don't need a college degree because I already had a college degree in sports medicine. And so most of them were like, you just have to have a degree. And I was like, okay, I don't think I'm going to be stuck in this position because I didn't have a computer science degree.

The other way was self-taught. I didn't think that I could put in the time and the work. One thing I learned very, very early on is there were a lot of things that I just didn't know about the field. I didn't know HTML. I didn't know CSS. I didn't know how to get a server started. I didn't know anything. If I knew anything about computers, it was more about the hardware side of it and nothing about the software side. So I knew very quickly that the self-learning aspect wouldn't work for me, and so that's kind of why I decided to go the bootcamp route.

I asked a lot of mentors, "Hey, what's the best way?" And they're like, "Bootcamp." And they're like, "Go to the one that teaches you the most." And so, at that time, the bootcamp I went to was two years long, but I was able to probably eight months in get a job in tech. And then, I completed it while going to work at that tech company.

VICTORIA: Oh, that's great.

CHAD: I mean, this might be a little bit of a hot take, but I'm going to say it anyway, which is I think that if you don't know how to code at all, or very little university programs, computer science programs aren't really set up to teach you that in a great way. It's more likely that someone with that level of experience will really struggle going into a computer science program not really having coded before.

Bootcamps are much more conducive to learning from scratch along with other people. It's not even necessarily about the programs, but going into a CS degree, so many people already do know how to program. And so it's really hard for them to make a well-balanced program that works for everybody.

WILL: I totally agree with that.

VICTORIA: I could see it. It's both ways. The way I've always heard it explained is a computer science degree will teach you a lot about the underlying principles that you might wish you knew later after you have finished your bootcamp. But a bootcamp will prepare you for on-the-job performance like day one, more likely to just give you the full breadth.

I mean, I've taken computer science 101 at University of Maryland, and I learned HTML, CSS, how to get a basic website up, some simple things that can get you up to speed. I think you could start from scratch and go that route. But it's hard to keep it up to speed with current technology trends in a college atmosphere. And so I think you'll see a lot of partnerships with universities now. And obviously, bootcamps were created to address that gap.

You got a job while you were still in bootcamp, and I'm curious how that went for you, that job search. That's a huge hurdle to just getting from the bootcamp to the first job; if you have any advice for people who are in a similar situation right now.

WILL: Yes, it was very challenging at the time. I think I applied to over 400 positions. My biggest thing that I would say is stay the course, hang in there. Keep going. There are a lot of down days that I was like, am I supposed to be in this field? Am I supposed to be here? The other thing that I learned very quickly was resources. Who did I know in the tech field? Who could I reach out to help me with it? Because that was another thing that I learned. I thought whenever I first took my junior dev job that I would come in and be able to really implement tickets and items.

And I quickly realized that they hired me because of my character and who I was going to be long-term and that I can offer very little at that moment of, hey, coming in, and doing a ticket, and really shipping a feature I cannot do that as a junior dev. But hopefully, in six months or two, three months, however long their time period was that I could ship a portion of a feature.

VICTORIA: Right. And that's always been...for me, someone hiring for technical roles and the entry-level point, sometimes I would prefer someone who has professional experience. Especially working in consulting, you have the ability to communicate your ideas well and work with clients, but you're still learning the technology side of it. That's a lot less than hiring a new college graduate who hasn't ever worked before [laughs] but may have a computer science degree. It's a totally different value that you're bringing to the role, I think.

CHAD: And that persistence really pays off. Just to make sure that timeline is clear, I think you interviewed with us for the first time five years ago or so, so I really appreciate you sticking with it and eventually coming back to us. That makes me super, super happy.

WILL: Yeah, and one thing that I learned along the way is there are different companies out there, and depending on your purpose and your goal, there are great fits depending on what your goal is. And my goal in my career was to learn and to be with a great company that had a great culture.

And I felt like thoughtbot was a good fit for me with that because I want to enjoy the people that I work with. I want to get to know them. I want to help them be a mentor, be a mentee, and thoughtbot was a good fit with that. That was one of the reasons why I put it on my list of hey, whenever that opportunity comes back, apply, apply, apply back to them.

CHAD: You originally interviewed with us as a Rails developer for a Rails development position. But along the way, you joined us as a React and React Native developer. So tell us a little bit about that journey along the way.

WILL: Yeah, so I did as a Rails developer, and I quickly realized that at that point in my career, Rails was harder for me to comprehend. There was nothing visual that I could really understand. And going back to what Victoria said with universities being able to keep up, at the end of my bootcamp, that was when React was on the rise. And so they actually released a module for React, and so I was able to really pick up that module.

And at that point, I thought React and front end was going to be a lot easier for me to comprehend and easier to get a job in the field, and so that's kind of why I went that front-end developer way. And then it's interesting now because I'm coming back around learning more Rails and, hopefully, be able to contribute to client work with the Rails side.


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CHAD: thoughbot's not the first agency that you worked at. Before you joined, you were working at another agency. Was there something in particular that gravitated towards this kind of work as opposed to working at maybe a technology startup working on a specific product?

WILL: Yeah. The two first jobs that I had in tech was typical software as a service products. I enjoyed it, but I felt like we were building on the same thing over and over again. And it was okay, but I know for me that I'm a big-time learner. And so I felt for me, I'm a big-time learner, and so I felt going the agency route would give me the opportunity to be exposed to different aspects of tech.

So at the last agency, I did some Rails work. It was very, very minimal, but I was able to do that. I was able to learn a lot about React Native and React and probably worked on a handful of jobs. Even at thoughtbot, I've worked on jobs and contracts that range from a month to six months. And I know potentially, I can work on a contract for two years, but it still gives me enough change to where I feel like the tech field will not leave me behind.

So I can work on a job or a contract for a year and then reset and say, "Oh, React released XYZ." And I can implement that into this new product or contract I'm working on. So that part right there is what really excited me about working for an agency and being a part of the company.

CHAD: Yeah, that's a big part of that variety, even both on the tech side but also just being able to work with different people and not be bound always to the same thing is one of the reasons why I've been able to do this so long I believe.

WILL: That's a good point because I love meeting new people. I love getting to know them. And it gives me that opportunity to work for a client, get to know them, and stay in contact with them but even go to a new client. If I was working at a product, I'm with the same company inside the four walls of that company. And so I love that aspect of getting to meet new people and getting to help companies deliver their dreams to the world. I really enjoy that.

CHAD: And that's what you're going to get to do as part of the host of the show too.

WILL: Yes. I'm excited about that too.

VICTORIA: I was going to say the same. You're going to meet so many cool people. [laughs] I've already met a lot of really interesting people in the last two months. So let's ask you a fun question. You're meeting new people; maybe you're introducing a new podcast guest. What's your favorite icebreaker question to ask?

WILL: I think my favorite question to ask podcast guests is why they do what they do. And the reason why is because it's very interesting seeing what propels people to go and do the things that they do. I guess I'm a student of people and humans. I love understanding the greatest people like Tom Brady, Michael Jordan. I know that may be up for debate.

VICTORIA: [laughs]

WILL: But just what makes them click. Also, for our guests, there are so many different aspects and products that people are coming up with, and so it's amazing to hear why they're doing what they do. And a lot of them, I'm like, oh, why didn't I think of that? That's a great idea. [laughter] And so I think that's my favorite question by far is why do you do what you do?

VICTORIA: I like that, yeah. As soon as I come on, I'm like, "So you're the founder of this. And why did you do that? [laughs] Tell me." But it's always an interesting story, just the right person, and the right place, the right problem to solve, and the right group of people around them to figure it out.

WILL: Yeah, and definitely the sacrifice that they're making. Being a CEO or founder of a company is not a nine-to-five job. You're sacrificing a lot of time, a lot of effort, resources. So yes, why do you do what you do? Because you're sacrificing so much. So why did you do that to get to this point? I love it.

VICTORIA: We could ask Chad that. [laughs] Why did you start thoughtbot, Chad? [laughs]

CHAD: I ask myself that every day.



CHAD: No, I'm kidding. Oh, we have a whole episode on that we recorded for our anniversary with the original co-founders that I had, and we did the history of thoughtbot. So I like to point that out every once in a while, Episode 262 from February 12th, 2018. Time flies when you're having fun. I didn't think it was that long ago.

WILL: [laughs]

CHAD: We're currently on Episode 442.

VICTORIA: I will say it is a productive podcast. There are a lot of great episodes that come out. I'm excited to have Will on to help share the experience of [laughs] creating them.

CHAD: Yeah. And speaking a little bit of meta, this is the first time we've ever had three co-hosts. We have an appetite, the three of us, for trying some new things with this new sort of season that we're embarking on. But we also love the show as it is, and so we're going to keep things sort of going like they are with some rotations and doing some joint episodes and that kind of thing.

But I wouldn't be surprised if, after a couple of months, we start to layer something new on. I'm not quite sure what that will be yet, whether it will be just maybe episodes with just the three of us, and not a guest, talking about some thoughtbot stuff or some things we want to talk about. Or maybe it could be something else. What do you all think?

WILL: I love that idea. I love being able to have different options and opening that out. I think it's a great idea. Like you said, I don't know what that looks like, but I'm excited that we have the opportunity to bring different aspects, different podcasts to our guests.

VICTORIA: Yeah, I'm already thinking of people I can voluntell at thoughtbot [laughter] and talking about topics that I'm interested in. [laughs] There's a lot we could do with that. And yeah, I think it'd be good to mix it up. How has working at thoughtbot supported your work-life balance with your family?

WILL: It's been amazing. At the time of this recording, I have three kids; their ages are three, two, and a couple of months. And so, from the very beginning of parental leave, being able to take that time and be with my son and take care of all his needs was amazing. And not having to worry about work, yeah, it was top-notch because I was able to really just focus on him and my other two kids. Because when you have a baby and other siblings, it gets tough, so I felt like most of my parental leave was just keeping my baby alive. [laughter]

The older siblings were amazing and actually surprised me. I thought that they would be jealous, and why is this new human in our house taking your attention? But it was actually the exact opposite. They wanted to hold the baby.


WILL: They wanted to be with him. And so it was like, okay, I'll let you hold them, but I got to be here with you, and I got to help you. And my two older kids are very independent. And so that was tough, but it's amazing to see how much they love their younger brother.


WILL: Yeah. So that has been amazing. But to continue on the work-life balance, it has been really amazing working at thoughtbot because we are a remote culture, and especially the clients that I've worked with the flexibility of the schedule. So yes, we have meetings that I have to make it to and be a part of the team. But for the most part, as long as I get my work done, I am in a good position.

So, to be honest, with the newborn, sometimes I'm up at midnight. And I'm able to work while I'm up with my son because that's the time that he wants to get up and eat and hang out, so I'm like, okay, let's hang out. So that flexibility has been amazing for me. I love the remote aspect of it because I am a big family person. So I love being able to be home with my kids as they're growing up, eating lunch with them, going on a walk with them. So yes, it has been amazing. To be honest, I don't know if I can ask for anything more than what thoughtbot provides to me as a parent. So I'm really thankful for that.

CHAD: That brings back a lot of memories for me because when our son was born, I also was up with him, and it would be one of those scenarios where you finally get him to sleep in the bounce chair or the chair, and you're like, okay, what do I do now? Because he's going to be up again at any moment. I was like, okay, I'll do some coding now, and it's like midnight, one in the morning, or whatever.

And I got a little bit of a reputation for these pull requests coming in at night but this general sense of understanding about why that's happening. And like, okay, now I'm not in in the morning because this was the schedule that I was on and a real flexibility and understanding of that. But it really brings back memories for me. I'm glad I'm well past that point now.


WILL: And I am thankful that thoughtbot is thinking about those things. Like you said, you're past that point, but you still are thinking about those things. And that means a lot to me that it's not in your forethought, but it's still very important to have that culture. And you're remembering how it was when you were a parent. That means a lot to me.

VICTORIA: Yeah. And I think that if you look at the state of the October's reports and see when developers are actually submitting pull requests, the windows are much longer. So post-pandemic with that giant shift to remote work, you will see them in earlier hours of the day or later hours in the night, but there are longer breaks in between. And I think for knowledge work especially; it's hard to just work an eight-hour block and be able to constantly be outputting during that time. [laughs] So it makes sense from a work-life balance but also a productivity overall balance as well.

CHAD: That's really interesting. I hadn't seen that report, but it resonates with me as true or resonates with me. And we've always talked about the concept of sustainable pace, and when we were in offices, that often meant Monday through Friday, eight to five, nine to five. This is the schedule we're all keeping. And if someone was deviating from that, it was like, oh, you may not be working sustainably.

Now, in a remote environment, it is much more about flexibility and recognizing that as long as people are working in a sustainable pace, variety in hours and flexibility is totally okay. And like you said, Will, it's about the work that you're getting done. Like, if there's a problem with what I'm delivering or what I'm able to do, let's have that conversation. Conversation shouldn't be about when I'm working or the hours that I'm working, the amount I'm working.

WILL: And as a human, your first thought is, is this person working the hours they're supposed to? And I think that's the first thought for a lot of people. But the one thing that I do like about thoughtbot is that trust that we have with our developers. Okay, there may not be their eight-hour block during the day, but are they getting their work done?

If they're getting the work done, why should I even say anything to them? Because they're being successful. That's what we asked them to do, get the work done. Are their clients happy? If their client is happy, I'm happy. And so I think that's one thing. The trust that thoughtbot has given to me as a developer means a lot to me, too, because I can work at midnight and still be productive and get my work done.

CHAD: I think it's telling. It's very rare for us to have a conversation with someone about maybe not working enough. It's almost always the opposite which is checking in with people and making sure that they're working sustainably.

VICTORIA: And I'm curious, Chad, about the policy of the four days of consulting and having Fridays for investment time; how that decision was made at thoughtbot. It's been a policy for a long time.

CHAD: Well, it comes from our value of continuous improvement. When we were 16 people, all designers, and developers, working client work five days a week, there was no time, strictly speaking, within a sustainable pace to reflect on the way that we were working, to make improvements, to learn new things, to create the open source that we were doing and the blogging that we were doing.

And so, if we were honest with ourselves, a lot of that stuff was happening outside of normal working time in addition to the five days of client work we were doing. And so I think it was Joe Ferris who said, like, if we believe in continuous improvement, we've got to carve out time and sustainable pace. We've got to carve out time within the week in order to be able to do those things.

The truth of the matter is a lot of our most popular open-source projects were actually created at a time when we didn't have investment time. And so, like I said, I think if we're honest with ourselves, we were really stretching ourselves thin at that point. So working on client work four days a week made us not only more sustainable but ultimately because it's continuous improvement...and so when you have a feedback cycle where short iterations, you can reflect on the way that you're working or that you have time set aside for making improvements, it makes you better the rest of the time as well.

And so now it's part of our secret sauce is the reason why we're able to be as productive as we are in that time that we have is because of that time set aside for improvement. The reason why we're able to make the open source and the blog posts that we do which make us have a bigger reputation and make our client work faster because we're able to use open source is because of that schedule. And so it's a self-fulfilling virtuous cycle of improvement. So that's where it comes from and why we've been so successful with it.

WILL: And that's actually a huge reason why I wanted to work at thoughtbot because one of my first jobs in tech, I would come in and knock out tickets, and I really thought that that was enough to be successful in the field. But then I quickly learned that yes, I was learning the tickets that I was working on, but there was so much more that I did not know, did not understand. And at that point, that's when I had my first son, and we were working five days a week.

So the biggest question for me was, with a newborn son and working five days a week, when do I fit in that investment time? When do I learn the outside aspect that we're not doing in the everyday grind of our tickets? And I quickly learned that I had to do it on the weekends. I had to do it outside of the hours that I was working. And it was hard. It was not a sustainable pace.

With thoughtbot, one of my criterias was being able to learn, being able to be mentored, and thoughtbot checked that off. But not only did they check that off, but they gave me the opportunity, the space to be mentored and to learn. So I love Friday's investment time. It's been huge in my career.

CHAD: I'm giving away all the secrets here, but it's okay because it's the execution that matters. But the reason why at your previous places you weren't necessarily able to do that is because that's not their product. Their product was the SaaS product that you were working on. And so when a company like that thinks about where they're investing, the investments that they're going to make are in their product.

It's one of the reasons why we call investment time investment time because I wanted to communicate that we are investing in our product, but our product is the way that we work. It is our people and our process, and the tools that we use. And so when we think about making investments as a company, that's what the product that we're in the market with is. And so we can afford to invest in improving that product in the same way that a company whose product is software can afford to invest in that software and has trouble investing in making the people, and the process, and the tools, and the culture better.

VICTORIA: That makes sense to me. And what I've found so far in having that four-day workweek and the way it comes out from a pricing perspective for clients is that you're paying maybe a premium for hours. But your team is able to get more work done in less amount of time because it's so focused. And then overall, you're getting a higher quality work product in a short amount of time. And I think it just makes a lot of sense to me.

And I've been working in many consulting companies, and they all have this problem. They all want to put out a lot of knowledge articles and blog posts and be known for their expertise but don't commit to making that time to it or spending the money on investing in people to build those products. So it's something I was really excited about for thoughtbot too. [laughs]

CHAD: This is great fodder for future episodes with just the three of us. [laughs]


WILL: Love it.

CHAD: Will, thanks again for joining the show. If we don't get to play D&D again together for a while, this will be a secondary substitute for that.

WILL: Yes, I do plan on coming back. That was huge also, so don't count me out.


CHAD: I won't count you out.

You can subscribe to the show and find notes for this episode, along with a complete transcript, at

VICTORIA: If you have questions or comments, email us at

CHAD: You can find me on Twitter @cyptel.

VICTORIA: And you can find me on Twitter @victori_ousg.

CHAD: And, Will, if folks want to follow along with you, where are all the places that they can do that?

WILL: Yeah. You can follow me on Twitter @will23larry. And I would love to interact and chat with you.

CHAD: Is the 23 for Michael Jordan?

WILL: Always.


CHAD: This podcast is brought to you by thoughtbot and produced and edited by Mandy Moore.

VICTORIA: Thanks for listening. See you next time.

ANNOUNCER: This podcast was brought to you by thoughtbot. thoughtbot is your expert design and development partner. Let's make your product and team a success.

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