mergeconflict265
James: [00:00:00] conflict. Our good friend, Frank Kruger is missing an action. He refuses to text me back. So he's not on the podcast this week in the United. Don't want to text me. Oh, be safe. Frank. If you're out there, if you're listening, if you're out there, hope. We love you. Please come home. We'd like to see you on the podcast.
Um, but in Frank Kruger's place, uh, is an amazing individual that I've had the honor to work with for the past 3, 4, 18 years of my life. Uh, I work every single day side by side for, for, for many years and, and now, um, get to see all the amazing things that she's doing with Madonna Maui and beyond, um, a good friend, Mandy.
how's it go. 
Maddy: [00:00:50] Hi, James. Thanks for having me on. I, I cannot quite fill Frank's shoes, but hopefully I am a, uh, entertaining substitute 
James: [00:01:00] for him. Nope. Nobody can fill his shoes. In fact, he 3d mapped his 3d shoes and then he sent me that 3d map. And then he said, now you can map your foot and then you can see that you can not fill my shoes.
So, yeah, classic Frank, you know, he's probably somehow magically has mapped with AI and machine learning, some magical algorithm that, you know, based on how many times I tweet you can calculate the size of a foot and then figure out if I can fill in his shoes, which the answer is no, I mean, without Frank, what am I.
Maddy: [00:01:31] Just hang out. Where's the conflict? Where's the merge 
James: [00:01:35] names, James? Well, I'm pretty excited. You know, I was, I was thinking a long time ago, we did this. Life and time of Frank Krueger. And he had a really interesting background story, just like ridiculous stuff that I had never known about. And since we don't have guests on very often to me, like we could talk about technology, you can do something.
People they'll listen to other podcasts. If you like, you want to get updates on the stuff that Maddie's working on. Like, man, I will tell you. Where to go. I mean, I was like streaming every single day. Like do one of those guys she's everywhere right now. He's just everywhere. So I figured like, it would be cool, Maddie, if you're down with it, it's like kind of a life and time of how you got to where you are today.
Maddy: [00:02:14] Yeah, that sounds fun. I definitely shout things about tech on the internet a lot. So I guess it's nice to shout about something else. Yeah. 
James: [00:02:22] Well, let's start with, before we even get to the story, the journey, if you will maybe just give like the 32nd, like, who is Maddie today? Like what are you doing in this car?
Cause I kinda, I kind of just assume that every, all the hundreds of thousands of listeners of this podcast, like obviously know who Maddie is, but if they don't, who is. 
Maddy: [00:02:43] Great question. I could talk about this for 45 minutes now. Um, yeah, I guess I like to still talk about myself as the, uh, productivity PM for.net mobile developers, but that's not really what I am anymore because things keep changing and growing and expanding.
Um, but yeah, I'm, I'm, I work at Microsoft. That's how I have the pleasure of knowing you. Um, and I'm on the Xamarin slash.net magnesium. And my job has just kind of been making developers hopefully more productive in their day to day while they're building apps. Um, a lot of people, if you know me, you definitely know my counterpart, my partner in crime, David aura.
Now who's like the SDK group guru of things. Um, but I'm more of just like the oh, visual studio Hart reload. Let's make sure everything works nicely. And, um, it's really fun. It's a cool job. I, I, as you will, hopefully shortly. I have no idea how I ended up here, but I really like it. So I think we did a good job.
James: [00:03:42] That is the best type of, of answer to like, oh, how did you get to where you're at today? I have no idea. I just, I don't, I don't, once one time someone asked me like, oh, how did you get this job? Like, when I moved to Seattle is like, oh, just Twitter. Like just dumb luck, you know what I mean? Uh, but I think that you probably actually have a lot more interested, sorry, of a tweet, which is actually how I got one of my jobs.
Um, but I know a little bit about like your background, like a little bit of, I really only know, like Maddie at Microsoft. That's really all I know because you know, like a good colleague. I like to keep the separation of work and, and home completely separate and, and respect boundaries. Like a good, oh, I don't 
Maddy: [00:04:28] have those, but I appreciate it.
James: [00:04:32] I think that's what I'm supposed to do. I don't know the manager now, so I'm not, I'm not allowed to talk about anything. Um, but you know, I think that will be kind of cool to start as kind of like, you know, what would I say is like your humble beginnings? Like not, not like here's Maddie year one, but kind of like, you know, what did you grow up around?
Obviously, you're now here in the tech scene at Microsoft for several years, working on. You know, frameworks and tooling and PM-ing program managing we'll get into that too. But like, you know, what was w what kind of brought you up and even got you interested in technology at all? 
Maddy: [00:05:11] Oh my goodness. Well, I'm an, I'm a nineties kid.
I'm a nineties baby. So everyone's always like, you're so young, but I very distinctly remember. Our first PC, which had windows 98 on it. And my parents got me Barbie fashion show the video game to install. I don't know if this was the same year. Obviously childhood all gets mushed together, but I put the disc in and it was like, oh, installed direct X.
And I was like click and it had the big blue background. And then all of a sudden I had like Barbie fashion show on my computer. And then I got Barbie Rapunzel and I got age of empires. And then I was like, wow, this thing is crazy. All I had to do is like, click this button. And then the screen had this really horrible, giant Italian text on it.
And then my game showed up, so cool. Um, and this was age, like, I dunno, like two to seven or eight. And I just remember being like, wow, like I want to build this thing, not the games necessarily. Although, I feel like that would have been cool. I don't even think I understood or comprehended that people had to build the games.
I think they just existed in my head. Um, but I just remember being like, wow, this box is like so smart. I wonder how that works. Uh, but neither of my parents were technical at all. They were both actually in real estate and, um, Pretty quickly put on the, the mindset that I was going to go into something businessy, maybe law.
I kind of wanted to be a pediatrician for a bit. I really had all these kids have this great, like I'm going to be an astronaut, you know, like I have this great idea and I was like, I'm going to do something at some point, I think not quite sure. Um, so I like knew I kind of liked science and I knew I kind of liked math, but I just thought that computers were built by people.
Under the, like, you know, um, the, the Hoth base in the beginning of episode five, like that is what I imagined, what computers were built. Like you, you were under the snow and it was a bunker and there were these really smart people. And I had no idea that there was anything that involved a career there until I was probably, yeah.
16 and someone was like, yeah, you have to like pick a major and start applying to colleges at some point. And I was like, oh, absolutely not. Like I have no idea what I want to do. Um, and I had started to think back like, well, what did I like when I was little? I don't think I can be a doctor because I absolutely sucked at science in high school.
It was horrible. Um, but I was like, okay, well I think I liked computers. Maybe I'll go build like chips, you know, like I, they have hardware in them. I have a game, boy. That's cool. There's circuits. Like I can do that. That sounds awesome. Um, and one of my friends actually had started taking apart people's X boxes when they got the rings of death and replacing the heat sink and putting that back in the Xbox.
And I was like, that's really cool. Show me how to do that. So I learned a bunch of like electrical engineering skills and I was like, that's what I'm going to do. I'm going to be an electric. Computer engineer. I'm going to go build chips. I'm going to go solder stuff. It's going to be awesome. 
James: [00:08:15] Kind of like what Frank does.
Like that's like the electrical engineering part of Frank radios. I circled all these things. There's this, there's this fundamental, you know, fascinating part of, of your, of what you just said, right. One is, is like, you know, there's the software aspect, which a lot of people don't really think about, but then you can see the thing, like you can see.
The computer, you can open up the computer, you can see the parts inside of it and like, oh, there's, there's, there's things physical here. We're software. Like you don't see the, you know, you don't see the, the code behind the scenes and Ida. Similar interaction to it. One of my first games I played was like a Lego world game where I was like this 3d character moving around besides math blasters, which is like the best thing, love that.
Lester's so good. So good. Uh, but same thing, right? Like you didn't really realize it's there, but I think it was also interesting, you know, my parents also like your parents weren't into tech at all. Right. My parents were in stainless steel and stuff. And um, but when you talk about the career aspect of it, that's, what's really fascinating because.
If people are doing the things, or it's really popular in that point of time, like, there's the standard, like there's the doctor, there's the accountant, there's the XYZ, like things that are, are staples, but when your parents or your, your, your guardians or whoever they may be, or your parental units at the time, and even in, in, in school, they they're sort of guiding you in a bit.
But if they're not into that scene, you don't even know that thing exists. Like that's even a possible. 
Maddy: [00:09:44] Oh, yeah, both of my parents were first generation Americans and, um, neither of them had went to college. My mom actually got her GED when I was in college, which was awesome, but they had just, you know, figured it out in real estate.
And so they wanted their kids to make money. So they said, Okay, kids, you're going to get a job that makes money. So you're either a doctor or a lawyer or a business woman miscellaneous. And I was just like, okay, that's how you, that's how you have a life. Like I had never even considered anything outside of that.
I think until I was in high school and it was mind boggling to realize the opportunities there are on this earth. 
James: [00:10:19] So you saw that computer parts, electrical engineering was a thing at least. Is, were there things in like high school that got you interested in that? Or was it just like, Hey, like you said, I have to apply for universities.
I have to pick something. Would you, you know, you don't have to pick, you should pick, but also now you don't have to pick and use your probably pick, should they pick shit? Cause I don't know. Well, it's like you apply 
Maddy: [00:10:46] to a school. That's good at the thing that you think you want to do. Yeah. There you go.
But like, if you don't know what you want to do, 
James: [00:10:54] no good 
Maddy: [00:10:55] point. Yeah. My high school was. Technically 20 years behind. That's how I like to call it. Um, without doxing myself, I guess are my high school is, was built in the sixties and our Bunsen burners leaked so bad that they actually almost didn't recertify us in time to get my high school degree.
So our computer lab was one room with a bunch of windows, XP PCs. And this is like early 2010s. I'm talking like windows, windows seven was out. Okay. Um, and it was not air conditioned. So if you went in the computer lab on a day, that was above like 70 degrees, you had to have like a fan at everyone's desk because the computers would overheat and shut off.
So I did not have a lot of exposure to. Science and tech, I guess, like I had a really good physics teacher. I learned about like how circuits worked. Right. But it's not like we were doing these like crazy labs. And, um, the only code I had written was like MySpace and tumbler page customization. So then I was thinking, well, I'm a hacker, you know, so cool.
I like played video games. So I was like, you see, I like tech, I totally know everything that's going on here. Um, but I had a couple of friends who were a little bit more like. Independent, I guess, than I was. And they would have cool things they were working on and they'd let me like watch them and bother them about it.
So I think I slowly like osmosis in a lot of information over probably three or four years. So that by the time that I was a senior in high school, I could pretty confident and be like, oh, I'm going to be an engineer. And that sounded very impressive. So people were like, oh, obviously like, that's great.
She's going to do so well 
James: [00:12:36] expectations. I know at least from my, my, my parents were so incredibly high and yet I still don't know if they know what I do at all, which is okay. 
Maddy: [00:12:49] My mom, uh, works for the city and she sends me it like job listings all the time. And she's like, This, this guy's leaving. He was such a sweetheart.
I'm like, mom, I, I would be no help. I would be the worst person for that job. I promise. 
James: [00:13:02] They're like, I think, I think we're proud of what he does now. Now I just go in and they're like, boom people. I don't know what you're doing. I'm just a manager. I'm like, oh, okay, cool. Like we understand what you do. Okay.
Let's let's just keep, it makes it easier. That's all. So it's good. So you now have this, this thought process that like, Hey, there's engineering and there's hardware. Right. But what do you do with that? Like how does that help guide your decision on where you want to go or do 
Maddy: [00:13:28] I. I'm from the Boston area. I was pretty adamant that I was going to stay in the new England area, mostly because I am just like really a home body, which I never, at the time, I really thought I was adventurous and cool and not lame at all.
But looking back, I was like, oh man, like even New York, I was like, that's a little, that's a little far for me. I don't know. Um, but I really wanted to go to a school where I could. And, you know, a because money cause college is expensive and horrible, but also because I knew that I was not quite sure what I wanted to do.
Um, and so a lot of the schools I had applied to were ones that had like co-op programs or like really, really integrated internship programs so that I would kind of be handheld into forcing myself to work like a legit corporate job early in college. Um, just cause I kind of. Looking back. I had the gut feeling that I wasn't quite sure, even though I told everybody I was a hundred percent sure.
And I knew exactly what I was doing. So I guess that was a good choice. But I ended up going to a co-op school in Boston where after like your first year. And the second year, either in the spring or like your third year fall, you do a six month internship. So yeah, so I was like, great. Like, this is perfect.
I'll go to a couple semesters of classes. I'll be a genius by the end of it, I'll go work and then I'll have a job lined up and I'll be all set 
James: [00:14:53] game plan, game plan, clearly laid out. Can execute this game plan, get paid at the end. Like at the end, there's a finish line. That's like page. 
Maddy: [00:15:02] Yup. That's it get a job life ends.
That's it. Uh, but as you can tell by the fact that I am here, uh, that did not happen at all. Um, I mean, I went to, I went to Northeastern. I loved it. Go Huskies. We have a great Northeastern presence at the Microsoft office in Cambridge. Um, and I fell asleep in calc. On my first semester, probably once a week, my professor was this very nice man, but every day he would put on individual latex gloves on his fingers because he didn't like touching the chalkboard.
And then he'd say, okay, I think we shall begin now. And the same voice and it just put me to sleep and I did not do well in that class. And I was like, oh man, I really need that to be an electrical engineer. Okay. Well, computer engineering doesn't require calc three. But it's almost the same degree. So I guess I'll just switch to that.
That was the beginning of like an existential crisis for me. Um, cause the first programming language they had us use was C and I was like, yeah, I was like, this is cool. Right? Like this makes sense. And then they were like, okay, here's an algorithms class and here's C plus plus. And I was like, oh. Not as cool.
This is much more difficult. Okay. Pivoting, I'm going into robotics because everyone on robotics uses. See, that's where we are. Now. I'm a firm where a person. Oh. So as you could tell, um, my life was just a bunch of me just deciding something and then being very confident about it. And then that not at all.
That's worked great for me clearly. So, 
James: [00:16:40] I mean, no, that's super cool though, because you know, when you leave high school and somehow you're expected to have figured everything out and that you're, you're making a decision before you learn about what's all involved in the specific topic. It's like not realistic at all in any, in any form.
It doesn't make any, if I look back on college, like it didn't make any sense. I did the same. I changed. I changed. Programs and like my last year, and I did the same thing, which was like, oh, like almost all of these credits apply, but like, I can just do these other credits that seem like way more interesting, you know?
Maddy: [00:17:14] Yup. I mean like long story short, my first year and a half of college, I went like full send on computer engineering and I got really into high-performance computing and I got really into GPU's and using things like open cl and like Kuda to do math. And which is funny because I am not good at math, but you know, that kind of math I was good at.
Um, and I had all these really cool friends and they were working for like AMD and Nvidia. And so I started to apply for my first co-op and I was like, I had a handful of robotics companies. Like I robot is, has a really big presence right outside of Boston. So that's a place that in shark ninja, which makes like the Roomba competitor.
So I was like, that's a place I'll throw some applications into. And then, you know, maybe I'll go into GPU's, I'll go into AMD. I'll go into Nvidia. And I did all these interviews and they were like, and I actually remember my co-op advisor being like, you're not technical enough for any of these jobs we're applying.
And I was like, but all my guy, friends who do the same research that I do apparently are technical enough. So whatever, no biggie. Um, and that was when I started to realize what being a woman in tech was. But, um, I got an interview with Microsoft, the garage program, which is basically, um, God, I hope George Ben, if you're listening to this, I'm sorry, but it's a summer camp for kids who are getting paid too much.
Um, the whole premise of it is it's like a startup accelerator, except you're working on ideas that product teams inside of Microsoft pitch. So for example, um, my first summer we worked on something that, uh, you know, the Intune team that has a presence in Boston, they pitched an idea to one of the teams and were like, you should build this.
And then when you're done, we'll tidy it up and. And then a team of like four or five developer, interns, and a PM intern, and the UX intern would go and like build it over 12 weeks and ship it. So I got this interview and I, and it was like software engineering job must know, object oriented programming.
And I was like, Hmm, C plus plus is object oriented. Right? I think so. No. And, and I actually, I, in one of my interview loops, I was like, just so you know, I'm like three quarters of the way through my first algorithms class. I have no idea why they picked my resume up for this. Really interested. It sounds like an awesome program.
People here seem really cool, but, uh, I've done a couple of hacker, whatever questions online and they haven't gone well. So I don't know how I passed that interview. Uh, luckily I think there were more along the lines of like systems design, which I could fudge my way through a little bit easier, but I got that job and I started in January and, um, I was a developer and I was doing node and we were building a slack bot and I thought that was the coolest thing in the world for like two weeks.
And then, uh, Yeah. Like two, three, maybe a month in. I started to be like, I don't think I like this, but you know why it's because it's JavaScript and everyone in computer engineering says that JavaScript sucks. And then I was like, ah, that doesn't make sense because this is actually not that bad. Yeah. And then, you know, I kind of was going through this thing and I think maybe like three months in, I was talking to my manager and I was like, I think I suck at this.
Like, I don't think I can be a developer. I don't know who I was trying to kid like. I this sucks. I don't like it. I'm a little too add for it. I guess I'm a control freak. And I was like super hard on myself and I, for some reason, my brain jumped to, I guess I'm not cut out for tech at all. I need to get out of here engineering.
James: [00:20:40] So, so this is, so this is a world. This is a whirlwind tour because if I recap, I don't know if this happened over like a year, a year or two. It sounds like. So you get in to this. Co-op you start off on this. I'm going to make. I'm gonna make like, uh, electrical engineer, I'm going to make like soldering stuff.
And then you're like, no, okay. Now I'm going to switch over to this other. I'm going to get into programming, but I'm going to do high-performance GPU program because some friends influenced kind of that, that area. And then you're like, no, I gotta do that. I'm gonna apply for internships and see what it's like.
And then you get an internship, not doing anything that you learn, because by way, whenever you learn stuff in college, you apply. None of it applies like what? You never know. No, none of it does. And, um, maybe like, there's something that sparks your interest. Like, oh, I like this thing. I'm going to go find things adjacent.
So then you come in and you're doing something completely different, but you, you sort of made it though. Like, you've like you, you accomplish a lot by pivoting a lot all over, but I still don't understand, like, what is a co-op. Like I understand like a co-op grocery store, right? Like a co-op what is a co-op university?
Because I, okay. My university, for example, it goes, it was also unique. Mine was a year round university, so I was able to finish really fast, um, and just never stop. But I, to graduate, there was a forced internship, basically like, Hey, if you want to graduate, you have to internship in industry. Is that like the essence of a co-op or is it like a.
Montessori type of situation. Like I have no idea. I don't know anything about anything pretty much. That's 
Maddy: [00:22:18] now you do. I mean, there's like three schools in the U S that do it, which doesn't make sense because to me it is awesome, but that's exactly what it is. It's like a forced internship, but it's during a semester.
So you basically don't take classes like this was January through June. And instead of getting, you know, sitting in class, I did an internship and that kind of like counted towards my degree as credit. Um, and so you have to do a certain amount of them to graduate, but of course, like everybody's journey is different.
And with tech, a lot of the times internships are focused around the summer. So co-op, doesn't always work out, but especially in like the new England area, a lot of companies like having co-ops cause it's six months instead of three. Um, you can really like engage on stuff a little bit more, and then you come back to school, um, and you only have to do one semester of classes and then you to go work again.
So that's really 
James: [00:23:06] so, so you, it's a bar in Boston. I've been in Boston a lot. Boston is a big tech hub. You know, people mostly think about like Seattle or mostly San Francisco, New York or Austin now, but like Boston's a huge scene. There's all sorts of stuff. There. And, you know, you threw out a lot of names, your name dropping, all the places that you are looking at, and that were in the area.
What, and, and, and like this re this reactor, not reactor, the garage program that, is that a, like, is that a special thing? Like what got you to Mike, like, even to that Microsoft program, was it just like, I was on monster.com and I was like internship program and it was like, with this co-op was there some, like, help.
Like guidance there type of thing. Like how did that, how did, how did that connection happen? Or like growing up, you're like, I'm always going to work for Microsoft. I'm migrant. I'm going to intern at Microsoft because it doesn't sound like that. You know, that that was your, uh, your dream. 
Maddy: [00:24:05] Though. Yeah. I, we actually had an internal like job site.
Um, and so we had co-op recruiters or whatever, they call themselves coordinators and they would work with companies to like, say, Hey, this is what a co-op is. This is why it can be more valuable than an intern for your company. Do you want some, um, and the Microsoft garage program was started. It was originally called the Foundry or something.
Um, and it was started in the Cambridge office because there's a couple of co-op schools. Uh, and they thought it would be nice to have kind of these off cycle. Um, so they had a single job posting on our internal job board. I would've never thought to apply to Microsoft. I mean, I saw it and I was like, cool.
Like that's what I used to use for Barbie fashion show. Like windows is a thing, obviously. Yeah, exactly. Like I was like, I remember being a little kid and being like, wow, windows is cool. I wanted to go do that one day. But like I had, it just never had materialized into anything for me. Um, So I applied to like the internal job and I got a hit and they were like, yeah, like, come up, we'll interview you.
You seem like you're a good candidate for a co-op because co-op is really not about, um, you like fighting that much for the company, but they're really pitched to the company as a way to teach students and kind of teach them the way that your company works and prime them. If they do want to come work there, full-time, it's like a six month job interview, which is really what all internships are.
It was nice that they kind of had those individual connections. Cause I think that definitely helped. And I was also the last semester that the Microsoft garage ran out of band. Basically they went back to summer only, literally the summer after I had done it. Um, so I got very lucky, like that was just entirely time.
James: [00:25:48] Because Microsoft internships and I don't know too much about the internship program I'm working with. Uh, I don't, I don't have an internship, an intern on my team, but, um, up one level does, I'm almost a fear right now. She was interning and I barely, I work with her. I barely have any idea, like she's there and then she's gone.
Right? It's like, it's like summer months, like, do you know how it, it differs basically, like now that you've been internal, I think you've maybe had some interns. 
Maddy: [00:26:12] Yeah. I've worked with a couple. Yeah, we did insurance. Yeah. Jason intern. And now he's not an intern anymore, but he wasn't it. Yeah. Um, and he lives in Boston now.
I, I converted him. Um, yeah. Internships are the reason they stopped doing the garage. Internship is because out of, out of cycle, the reason they focused it back on the summer is because recruiting. Wants to put on a show for interns, um, and internship is as much for. Recruiting as it is for the intern, um, in big tech at least, right?
Like obviously different companies are different, but you hear about like those crazy parties they throw in SF for like Google interns and intern a Palooza and all this crazy stuff and like internships or when they roll out the red carpet and say, you should come work for this company because we're awesome.
Um, co-ops were not really, I guess, sexy is the word. Like, they were just kind of like, you're here. Hang out, do your work. Okay. Well, we have interns coming in, so they're like the ones that are like really fancy, but you guys are here and you're doing cool stuff. So that's cool. Um, yeah, so it was really like, so I get so halfway through my co-op in like March, I was like, I think I need to quit software engineering and go to business.
And one of my managers who was a pH was like, you don't have to leave tech if you don't want to code every day, like you can still be technical. Be a full-time developer. And I was like, bullshit, like there's, excuse me, sorry. A bleep. 
James: [00:27:49] Leave it out. 
Maddy: [00:27:50] Yep. The broadcast I'm like, there's no way. And he was like, oh, we have this role at Microsoft called program manager as like, I'm not a manager and I'm very bad at timelines.
So this is not because I thought it was project manager. I thought it was, I had a team. I thought it was, I don't know. And he was like, just hang out for a few more months. Do the regular internship experience with the rest of the Microsoft interns who roll in and these are, you know, like the MIT and Harvard kids that come in and are super smart and like, you know, went out of their way to find this internship.
And I just kinda like fumbled into it accidentally. Um, and all of a sudden I'm here and I'm a PM intern and he's like, there are these six intern projects, help them out. There you go. And I was like, okay.
James: [00:28:37] So, so, so there's, there's, there's two types of interns. Chips is what I'm hearing like you were in the garage when you were, you were like, I'm an engineer. I am right. I'm slapping the keyboard writing code. And you're like, no, fam this is not my, this is not my jam, but obviously you're highly technical, highly skilled and enjoy somewhat of tack because not even doing it for a little bit of time and it doesn't sound like you hate it.
The experience. You're just like, Hey, this thing that I'm doing every day is not for me. 
Maddy: [00:29:07] Exactly. Yep. 
James: [00:29:09] So you're not a manager though, right? 
Maddy: [00:29:11] No, no. So this was, oh, this is where I feel like the real transition into the second half of my like college life came in because I was like, okay, now I have to figure out this whole new career thing, which is PM, which what I just, what basically the way it was described.
Is engineers and customers and UX and sales and marketing, and all these people have to work together. And sometimes in small companies that just works out well, but with bigger companies and bigger teams, like that can be kind of a really challenging thing. So we just need people who are there to kind of coordinate.
And I was like, ah, great. I'm a professional coordinator. Sounds awesome. Like I had no idea I, and anyone who's a PM or works with a PM knows that like every PM job is entirely different. Yeah. Um, and it depends on your, your team and your engineers and your manager and your product and all this stuff. But I had kind of thrown myself into, um, learning about what a PM like was supposed to do.
And then of course, like a weekend, I was like full send on this career. Like, I'm the best I'm going to do this. Um, also fun fact while I was at that internship, Xamarin was acquired by Microsoft. I do remember watching the build keynote where they announced visual studio. And being like, so they just took this thing and they called it something else.
And, uh, by boss at the time it was like, yeah, but that Miguel guy is like really, really cool. So I'm super excited cause they're in Boston and like, they totally am. I come to this office and I was like, wow. What, um, that's a 
James: [00:30:48] big deal, you know, like at the same time, like everyone is Xamarin is just like working with Nat and Miguel and Joseph, like no big deal.
Right. It's just like all we know. Cause there's like really down to earth, it was like no big deal, but then it's, it's, it's interesting to like, hear like, be like, whoa, like. That person could be in our office. 
Maddy: [00:31:06] Yeah. Like that's the open source.net guy. And I was like, I have no idea what you're talking about.
Like please, 
James: [00:31:15] that, that that's, that's awesome. Because you know, when I it's, it's, it's like a similar story. Like I remember like when I went to go interview at Xamarin and like, I didn't, I didn't know. I got to know who Miguel was. I knew who now I know Joseph was. I mean, don't tell them that now, but like I wasn't in the scene.
Right. I was, I was a type of developer. Like I got hired to do a job. So like I was in the documentation every day. And this was before like mass videos and live streaming and all these different types of where you'd see the people. And I never went to a conference. Like I never went to conferences and, and if I did it, wasn't open source conferences.
I, everything I did was closed source my entire life. And I didn't, I didn't understand that world. So. Uh, it's, it's always funny to me when, when, when I hear stories like that and be like, whoa, like in awe and just, I don't know, just like worked with that person. I remember one of my buddies is like, you were out to dinner.
He's like, where do you work? I was like this. I was like, yeah, I was just like hanging out and, and, um, Miguel was in town and I was like, yeah, I'm going to go like, hang out with Miguel or whatever, blah, blah, blah. And it's like, you're eating dinner. Miguel. And I was like, yeah, like, you know, got to eat, you know, six 30.
And he's like, but with Miguel and I was like, I was like, Yeti was like, I'm going to, or we're going to go to the, the steak house in Bellevue because that's what Miguel likes or whatever they're like, but with the, can I. Come to dinner with Miguel. And I was like, I wouldn't see why not? Like, he's just a, just a person.
I mean, like, do you eat? Cause like if you eat, Miguel's going eat and I'm probably gonna eat too, but like with them again, and then like, I remember like picking up the Gail again in the. And, uh, just to pick them up in our car or whatever the rental I had or whatever. And they're like, he's like, is Miguel going to get into the car?
I was like, yeah, we're going to, while we're all driving together, it's all happening. As a normal 
Maddy: [00:33:11] human, he has like the ability to walk, you know, and eat and he's going to get in my car and then get out of my car and then go into this restaurant. 
James: [00:33:21] That's happening. It's all happening. 
Maddy: [00:33:25] Oh, gosh, and looking back, I was just like, cool.
Like whatever this guy seems cool. But like, yeah. So, so out of that, and most of the intern projects were using.net to be fair. Like, I, I did actually touch C-sharp before starting this job, which I feel like I have to remind myself sometimes, but I would like go into the XAML and I'd be like, oh, this is gross.
Like, and anyone who is followed by work knows I am all about the XAML life now. It's really a 180 on that. But, um, at the end of the summer, the way the garage worked was because it wasn't a traditional internship. The way that Jay Kirsch, who was an intern art on our team, he came, he entered for our team.
And at the end of the summer, we said, Hey, Jake, you're great. Come back full time if you want to. And he said, absolutely. And we said, great. Since you're not actually on like a products team in the garage, since your projects are just kind of like sponsored, they don't have the head count to hire all the insurance that worked with.
So you have to go and find another team that has a spot and then interview with them. And so I thought I was like the coolest person in the entire world. And here I was like, oh yeah, I'm a PM. Now. Like I did this for 12 weeks and I read cracking the PM interview and I'm the best. And I'm going to go interview for all these teams.
And, um, I bombed that whole interview loop so bad. And like, I, I thought I did really good. And I was like, oh my gosh, like I really bombed this. Oh, no. Like, I guess this isn't what I'm cut out to do. And so I'm like, you know, I'm 20. I can't, I can't drink yet. I'm in the U S so I'm just kind of sitting there in my dorm room, like September, like, I guess I have to go back to software, like this sucks.
Uh, what am I do? Um, and luckily like both of my managers in the garage are peaches and I love them so much. And, and they were like, well, you know, maybe we didn't prepare you enough for the interview. Like it was kind of frantic. Come back next summer for the garage, but you should go do it an actual co-op again, first.
Um, so then I like really full send into robotics and stuff. And I, I went to Amazon robotics, which used to be called Kiva systems, but they do the warehouse stuff for Amazon. Oh, cool. Um, yeah, and it was awesome, but I went and I was like, I'm interested in this PM thing. So like, I like to like have a project, but I can kind of own on my own as well as, you know, write code and get to know all these systems and stuff.
And, um, I didn't really like the culture, I guess that much. Just my computer just fell asleep. Oh, it's back. Um, yeah, like it, Microsoft is really like go home at 5:00 PM and. I don't know if that's because they still kind of felt like a startup because they had just really started to become Amazon or what, but it was like everybody worked all the time and all people cared about was metrics.
And if things got faster or slower and some people, like some of my friends that worked there too, like loved it. And I was like, oh no, like, no, I really can't be a PM or a software engineer. Cause I've tried these two totally different things. And I sucked and hated at them fault. Like this is horrible existential crisis mode every semester in college was its own existential crisis.
So I went back to the garage that summer and I was like, okay, I got more involved with entrepreneurship stuff on campus. Um, I started working with like our art Northeastern, like startup accelerator thing. Like it was a product development studio where we basically did what we did in the garage, except it was unpaid.
And it was people who were in class and it was. Really stressful, but it was really, really fun. So I felt like I kind of had a better grasp of product development and like what goes into customer obsession and what all these things actually mean in practice. So that time around, I felt, um, a little bit more like I was actually doing a PM job instead of just being like, that would be cool.
Let's do that. Um, and Mikayla Hutchinson, who is on the Xamarin team or was on the San Mateo. And it's, I just kinda thought net PM was my women at nerd, new England research and development mentor. Oh, cool. And so that was my luck, like, literally, like, all right, you're paired up with this person who's on the Xamarin team.
Cool. I don't know what that is. Oh, that's the one that got acquired. Oh, everyone thinks they're cool. Great. Whatever. So talking to McKayla, I learned a lot about Xamarin and also one of the intern projects I worked with was, um, ink to code. I don't know if you remember that. I do. 
James: [00:37:54] Yeah. I interviewed, uh, uh, I think.
Whoever like the lead of it was like the garage lead person that, you know, did a bunch of stuff and worked probably with, with you. I think they like came on the Xamarin show at some time to show them 
Maddy: [00:38:08] you don't have to go Google that. Um, and I bet, you know, Alex Corrado, who's like a Xamarin celeb for back in the day or whatever.
And it's like, oh, like these people seem cool. Maybe they'll hire me. 
James: [00:38:22] I don't know. Yeah. And I 
Maddy: [00:38:26] like. We sat on the same floor as them this summer. Um, and I know you weren't, you were probably in the office just to visit, but the Xamarin team absolutely hated the garage and turns cause we were so loud and so annoying and we had like razor scooters and we'd scooter around like these little punk interns, and we'd be like shouting at each other.
Taking calls. And I remember Pierce Bogan, like now I'm just name dropping, but like Pierce Bogan, you know, like be sitting there in his cube, like death glaring at the interns and I'd be like, wow, these guys are like, so uptight. Um, and Pierce is the least uptight person I've ever met. So that's really funny, but I, like, I met McKayla, introduced me to, you know, Joseph Hill and, um, Miguel.
And she was like, we don't really have like the PM role. Like we're kind of figuring out what we are in Microsoft right now. Um, but you know, we, we definitely have room to hire and we'd be interested to kind of see if you'd be a fit like you like startup stuff. You seem to like tech in some capacity. So that's.
I don't know. And I was like, okay, cool. Like, great. I guess I'll talk to you folks. So then I kind of went and learned a ton about Xamarin those last couple of weeks. Um, and it, it helps that we were working on ACTA to code too. Cause I was like, okay, like this is actually developed. Like it was the first developer tool I worked on.
Like I was like, oh, that could be really cool. Imagine if me some PM who hated writing code could go draw a UI. And then spit out XAML, which is literally what this product did. And it used the inking API for windows and whatever. Um, and it was a UWP app, which I think is funny that we didn't build it as a Xamarin app, but whatever.
But, um, yeah, so I, I like went through this interview loop and Joseph was like, so what, why do you want to be a PM? And I was like, Uh, I like helping things work better. Like, I don't know, you know, about Xamarin. And I was like, well, it's for apps. And it's like, uses the C-sharp thing. And he was like, okay, like, cool.
Um, and so I really thought that there was no shot. I was 
James: [00:40:39] like, nailed it. Nailed this interview. This is going great. Yeah. Yeah. 
Maddy: [00:40:42] Like I was like, I Googled it for like so long. I really thought I knew what I was talking about. And I went in and I was just like rip. Um, and I don't know what the heck you saw in me, but I was at Grace Hopper a couple of weeks later, like, you know, schlepping around the career.
Fair. Like every senior in college, like, please hire me. Please hire me like, hello, please hire me. Hello? Oh, I'll take a sticker. Are you hiring? And, uh, Joseph called me and I was like sitting on the ground doing homework at a hallway, Grace Hopper. And he was like, Hey, we're going to offer you a job. I just don't know how recruiting works yet.
So like, if you're going to accept a job, they're just like, wait until you get our office.
And I was like, what? Who this guy? Nuts. Like why are they offering me a job? Um, so I spent the rest of my senior year. Like eventually I got the offer and I had a couple other things I interviewed for it, but I was like, you know, I love Microsoft. I will be able to stay in Boston and I kind of spent the rest of the year, just like learning about.net and literally Googling.
What is the difference between.net and C-sharp like, these are the questions that a senior in college is asking themselves, like, what is mano, Y mano different than.net.net was open source at this point and just become it. So I was like, what's the situation here? Like I had used visual studio. I had used IDs before, but I just had no idea like the space of developer tooling.
Um, so when I started that one. That was kind of like, it was almost by accident that I ended up in developer tooling, but within a couple of months, I think I was probably like this. The perfect place for me, because I still feel technical. And like you said, like I do a lot of technical stuff. I demo in code.
I get to write code and write my own apps and play around with stuff, but it's not like I'm contributing to visual studio and I have to deal with things that are important that I complain about all the time, like testing and like. All these compliance work stuff that you have to do. And like, all my code is never pristine.
Like if you've seen me demo it, you know, that I'm like, I just slap it all together and I call it a day, but I get to still do that. And then I also get to like work with developers who are technical people, who are the people that I love. And that I like such a big reason I stayed in tech was because there were so many developers that I just like liked being around.
Um, Yeah. So it was completely by accident. And, uh, I was very, very fortunate. And of course I met you and you kind of were the person who got me into like streaming and talking. And that's a huge part of my job since that. I really love that part. Um, and customer getting to talk to customers is probably the only thing that keeps me going sometimes, like when everything's broken and I'm just like, I can't do this anymore, but someone's like, oh my gosh, like this random thing you worked on.
It's so helpful. It's like, oh, I remember why I do this job now. Like, this is great. Um, and yeah, so I've been at it for a little over three years now, and I know what.net is. Believe it or not, it happened 
James: [00:43:53] three years, but you figured it out. Nice. 
Maddy: [00:43:56] Uh, and, uh, I, I, yeah, I just, I guess looking back at it all, I'm like, okay, well, lots of accidental injury.
Falling into things and then just going full send on them and then them either not working out or working out well, 
James: [00:44:14] I mean, I think that's, that's the beautiful part of it, right? Is I, is that tech is I almost like don't like when people use the word tech, because like, all right. As a tech company, what does that mean?
Right. All right. Oh, they, they build some piece of software. They building the software. I was like, really? Here are the things that I like doing. And there's a lot of different types of jobs in and around that. Right? Like you look at a grocery store. It's like, well, there's a lot of jobs in and around the grocery store, you know, that are here and there.
Or like construction. Like there's a billion jobs in around construction as the same thing, like any company. But I think it's so cool that how you pivoted, uh, S. Here and there be based on like, Hey, I like doing this thing. I don't like doing this thing. Like you figured out the thing that you like doing, and that's the most important part is like, you want to come into work and work for a company that you want to work for.
But like the thing that you do every day, you also want to ensure that you like, and it sounds like as a PM program manager, you're doing a lot of different things. I mean, you kind of said at the end, like you're not. Writing codes doing demos, you are doing customer engagement, developer engagement, um, onstage keynoting things, uh, be willing, have seen Maddie doing that, which is, have you ever, did you ever think right.
Sitting down. Like, you know, playing that game when you were like five years old, like, oh, I'm going to be on stage doing keynotes at huge developer conferences and demoing plant applications, uh, that I built 
Maddy: [00:45:45] never in a zillion years. I mean it, and I have friends from college who were like, why do you have so many followers on Twitter?
Like I don't, I used to tweet about the Patriots and the batch. And now I tweet about net, so that's cool. Uh, but sometimes there's some bachelor thrown in there, but yeah, I it's, it's mind boggling and I love my job so much because every single day I wake up and I do something completely different. I mean, I will complain about my job until the end of time don't get me wrong because I am a human being and I will be like, everything is a disaster, but, um, I don't know, like I woke up today and I was like, oh, we have some team demos and I have a couple of one-on-ones and then Monday I'm going to wake up and I'm going to do a bunch of customer interviews.
And Tuesday I'm going to have to go back to the drawing board for all of our visual studio, 2022 features and see. You know, like the whole scope of everything we're working on. And then Wednesday I'll probably have to dive deep into one of them. And then Thursday, I'm probably just going to be like, I'm taking a nap.
Like every day is so completely different. Um, and it's, it's all technical in its own way, but I've been able to turn it into what I want it to be. Um, and I mean, sometimes obviously it's not right. Like, I am so bad at writing blogs. And we have so many people on our team who are so good at writing blog posts, but I know I have to work on that skill.
So I will like suffer through a blog post every once in awhile. But. You know, it's just one part of my job. I'm not a blogger. It's just something that I've done. 
James: [00:47:11] Um, yeah, very many. Uh, it's like Swiss army knife. There's very many different pieces in your toolkit of odor and things that you're, some of them you're super good at and you super enjoy doing some of them.
You only have to do on occasion. You want to get better out and keep improving or some things you're like, I didn't like doing that. I guess I'll get it done. So, um, yeah, this is awesome, Maddie. Thank you so much for coming on and telling the life and time of, of Maddie. 
Maddy: [00:47:36] Thank you for having me. I hope this is somewhat interesting to people.
Hopefully a 
James: [00:47:41] little inspiring too. I'm inspired. I think it was a really cool journey and you know, I think the biggest thing I take away is. Is, you know, especially for kids that are going out, looking to be like, what does it mean to be in tech? Like, you know, you, you went and you experimented, right? Like you almost experimented with your career.
Like you experiment with building features for the product. Um, and that's a, you're good at it and that's what you're doing here, but, um, as great. Yeah. 
Maddy: [00:48:08] If I could go back and say like one thing to myself, it would be, yeah. Just say yes, as you are doing, like, don't feel stupid about changing your mind on things and just diving into things head first.
Cause that's how you're going to figure out what you like and what you hate. 
James: [00:48:21] Totally. Well, Maddie, thank you so much for coming on. I will put links to your Twitter and to all the other things, all the places. And don't forget, you can join Maddie on Donna Maui, community standups and Donna comp and all the things, you know, she'll tweet it out.
So you just follow her over there. And I thank you so much again, I really appreciate. Thank 
Maddy: [00:48:39] you talk to you soon. Hi, Frank from afar. 
James: [00:48:43] Yeah, I know. I need to like insert Frank's voice at the end of this. All right, let's go do it for this week's merge conflict. So until next time I'm James Montoya, Magno and Frank is somewhere in there enjoying life.