Episode 296: Business people don’t hate tech people with Nate Walck

The nature of the role of a Mac admin is different at big and small companies. Like many jobs, we have a smaller scope in larger companies – but potentially a larger impact. Every choice or line of code at a true enterprise scale has a resounding effect. At smaller companies, we take the blinders off given that we don’t step on other people’s toes. The role of a Mac admin might include security, compliance, developer operations, and even business analysis. Today, we’re going to talk with Nate Walck about his journey from a CPE at a large enterprise to working at a startup and how that transition has been.


  • Tom Bridge, Principal Product Manager, JumpCloud – @tbridge777
  • Marcus Ransom, Senior Sales Engineer, Jamf – @marcusransom
  • Charles Edge, CTO, Bootstrappers.mn – @cedge318


  • Nate Walck

Transcription of this episode brought to you by Meter.com

Click here to read the transcript

Meter is the easiest way for businesses to get internet, networking, and WiFi. Our full-stack approach combines hardware, software, and operations so that any company can seamlessly run on a reliable and modern network.

  • Streamlined installation: We take on the complexities to make designing and deployments easy, fast, and stress-free. We manage the entire installation process, and provide ongoing maintenance and support.
  • Network hardware, security & management: We design and build our own controllers, switches, and wireless access points. After the network is deployed, review your speed, usage, and security in one unified dashboard. No need to hire vendors in every location or have IT teams fiddle with manual configurations — everything is automated with our software.
  • Simple pricing: Pay one monthly rate with no up-front costs for installation, configuration, or hardware.

Sponsor Read:
This week’s episode of the Mac Admins Podcast is brought to you by Kandji. Automation in IT is a hot topic and for good reason. Automating repetitive tasks frees you to focus your skills on more strategic projects that move the needle for your organization. Kandji, the Apple device management and security platform features over 150 pre-built automations to multiply your effectiveness and impact daily. To see how to take the repetition out of your to-do list, visit kandji.io. That’s K-A-N-D-J-I.io.
Hello and welcome to the Mac Admins Podcast. I’m your host, Tom Bridge, and it’s great to be back with you, Charles and Marcus. How are you today?

Tom Bridge (00:00:45):
Hello, and welcome to the Mac Admins podcast. I’m your host, Tom Bridge. And Marcus, you have a fuzzy friend.

Marcus Ransom (00:00:51):
I do. And it’s not the pop filter on my microphone. So, um, I currently have an eight week old kitten sitting in my arms here, because that is in apparently the only way to stop said kitten from causing complete nutter chaos around the house.

Tom Bridge (00:01:07):
Nice. Well, you know, I was gonna say, if anybody hears the meowing or, uh, you know, I noticed that you did take the bell collar off, and James, thanks. You hang on. Uh, but, uh, yeah. Oh, there you go. Excellent. Foley work. Yeah. Uh, but, uh, you know, I was gonna say, we got a tiny friend, uh, we promised pictures in the, uh, in, hang

Marcus Ransom (00:01:24):
On. I’ll hold, I’ll hold daisy up and someone can all take a photo.

Tom Bridge (00:01:28):
I gotcha. I gotcha. All right. 1, 2, 3. All right. Done. Yeah. Um, so yeah, that will be in the show notes for everybody to see, uh, excellent podcast art for all of those things. Uh, and Charles, how are you? That hat looks very coldly and cozy.

Charles Edge (00:01:42):
It is very coldly. I, I, it, I, I, you know, what are you gonna do? Um, yeah, it’s winter, you know, so you do the things u unlike Marcus’s family who came home with a kitten that will destroy everything and then ran off to the beach .

Marcus Ransom (00:02:00):
I see what they did there.

Charles Edge (00:02:02):
. Yeah, . Yes. You know, I, I think every few years we forget that the little kittens are so cute and cuddly, and when you touch them, they pur and then they rip everything to shreds . So, good luck. .

Marcus Ransom (00:02:18):
Yeah. D Daisy has been doing cable management in my office, so, um, oh, no, no. . Yeah. If, if I disappear from this call at any moment, it’s because, you know, the temperature has changed and bits of copper that were previously the same bit of copper are now no longer the same bit of copper

Charles Edge (00:02:35):
. And it’s, it would be impossible to know if her fur was standing up, cuz she’d been into something she shouldn’t have, because little kittens, their ed always stands up, and so they get a little older and it sits down, so, yeah. Yeah, she’s very adorable. Yeah.

Marcus Ransom (00:02:51):
I’m, I, she, she’s, she’s lucky. She’s adorable, I think is what I’m starting to feel like at the moment. .

Tom Bridge (00:02:58):
Oh man, isn’t that the truth about cats?

Marcus Ransom (00:03:00):
But the, the good, the good news is, is that a moment Alfie hasn’t torn her limb from limb. Um, and we’re going on the theory that this will knock the edge off Alfie and that all this time, um, he hasn’t been an asshole, he’s just been lonely. Um, so we’ll see how that goes.

Charles Edge (00:03:17):

Tom Bridge (00:03:18):
, well, we’ve got an incredible guest tonight. Nate Walk. Welcome to the Mac Dance podcast. It’s so great to have you here.

Nate Walck (00:03:25):
Thanks. It’s, uh, it’s great to be here.

Charles Edge (00:03:27):
And I, I gotta just say real quick before we get started, so Nate was, um, Nate was probably someone who I assumed that we had had on, and then when we went to do the 3D printing episode, I, I said, oh, well, Nate’s already been on because he’s such a presence in the Mac community, you know, so I just kind of assumed, and every now and then, I think, you know, we forget that maybe we didn’t, so Nate’s like, maybe

Marcus Ransom (00:03:59):
We need to, maybe we need to do a diff of the Mac admin Slack, and then

Charles Edge (00:04:03):
Actually just

Marcus Ransom (00:04:03):
Get a list of the 12 people left from the 50,000 members.

Charles Edge (00:04:08):
So, so when I wrote up the show notes for the 3D printing episode, I, you know, in there I was like, well, since Nate’s already been on, we don’t have to have him do the, and then Nate commented in the Google Doc, I haven’t been on, and I’m like, oh my goodness.

Nate Walck (00:04:22):

Charles Edge (00:04:22):
We’d have had you on two years ago or four if we knew that, but, you know,

Nate Walck (00:04:27):
Not, not at all. So it’s like, it’s like Arrested Development and Buster, you know, it’s like, I, I’m, I’m from the school, I’m from the school where you should either be seen nor heard. So I’m very good at hiding. Uh, you know, I can go on family vacations and I will not be in any of the pictures because I see a camera coming out and I just run the other way. So it’s, it’s, it is in part because I’m just like, you know, I avoid, I avoid stuff. So, you know, it’s all good.

Charles Edge (00:04:49):
When you said it’s like a rusted development, I thought the next words outta your mouth were gonna be, because I shower in my shorts, but maybe not.

Nate Walck (00:04:57):
No, no, no. Not like that at all. Not like that at all. More, like, more like popping up to say things in Slack and then just disappearing for days, you know? Right. You know, it’s, um, when, when stuff gets busy, it’s, you know, it’s hard to, it’s hard to stay as, as engaged, so it’s very easy to, uh, to fall by the wayside and, and disappear for a bit. truth.

Tom Bridge (00:05:20):
Yep, for sure. Well, so the nature of the role of the MAC admin is different at big and small companies. And like many jobs we have, you know, uh, a smaller scope in larger companies, but potentially a larger impact. Uh, every choice or line of code at a true enterprise scale has a resounding effect. Uh, at smaller companies, we take the blinders off, given that we don’t step on other people’s toes. Uh, the role of a Mac admin might include security, compliance, developer operations, even business analysis in some cases. So today we’re gonna talk with Nate about his journey from being a C P E at a large enterprise to working at a startup and how that transition has been. So, you know, welcome. We’re thrilled you’re with us. And, you know, yeah, we just talked a little bit about the fact that we should have had you on years ago, and, sorry. Um, but you know, before we get on,

Nate Walck (00:06:08):
No apology necessary at all. No apology necessary at all. , don’t feel bad.

Tom Bridge (00:06:13):
We do love talking with people about their origin stories. And I want to get yours because you’ve got a really unique one. So, uh, take us through a little bit about how you got into being a, a McMan and, uh, where you’ve gone since.

Nate Walck (00:06:26):
Uh, sure. Yeah. So I feel like I need to start at the beginning. Um, so my background is very different, as you said. Um, and in that I grew up with, uh, PCs in the house, you know, PC clones. Uh, so for me, my first operating system was dos, dos six, um, and I had an eight year old, a brother that’s eight years older than me. Um, and, uh, he, uh, he always had priority on the computer, so I had the privilege of sitting and watching my brother use the computer, um, and, and learning that way. Uh, and, uh, and that was kind of how I got started with all this. But, um, then once I got into like, you know, uh, early teens, uh, I used Windows, I, I got Linux magazines, and I had Mandrake Linux, and I, I did Gen two Linux and in, uh, late high school and early college.

Um, and I did a lot more on the Linux side of things, uh, prior to getting on Mac os and, uh, when Mac OS went to a Unix space system that I became super interested. So I was doing all types of crazy things. I had a Lenovo that I was wearing running para PC on trying to run Mac OS on there and is awful. You know, it is like two frames per second or three frames per second. It was, it’s just impossible to use. Um, and there’s all types of things that I did like that just kind of like messing with, uh, Mac Os not on Mac hardware. Uh, and I was at the university, so I’d been supporting doing desk site support, repairing Lenovos and, um, and IBMs as it was that long ago. Um, and, and doing repairs on the PC side. And then I was on help desk, uh, doing phone calls for the university, and we didn’t have anybody to that did Mac stuff and the Intel Max just happened to come out.

Um, and I was like, oh, Intel Mac Suite, I can dual boot this thing. I can just play around with this thing. It’ll be fantastic. So I said, you know, I, I talked to my manager, I said, if you get me an Intel Mac, I’ll do all the Mac support and take care of all that. And that’s how I got into it in the first place. Now, I did have some ulterior motives. Um, I wanted a laptop that could play World Warcraft and the Intel Mac definitely was it. And, and, uh, and Blizzard was really good about doing, uh, Mac OS and Windows support for a lot of their games, uh, even all the way back then. Um, so yeah, so, uh, that’s how I just, that was my first, um, professional Mac. I had a, a Power PC mini before that. Um, but it wasn’t quite powerful enough to play while, so I sold it, um, , but the Intel MacBook Pro was fantastic and did a great job.

Uh, and then I got into that, I started doing all the, the dust side support for the back stuff, uh, and then eventually taking care of the labs, doing the cis admin work. And, um, my university didn’t wanna spend money as many universities are, uh, prone to, uh, a desire. And I was like, okay, well that means we’re not buying, we’re not buying that because they don’t wanna spend money, so we’re not doing that. So I started looking at, you know, because of my Lenux background, I just started Googling around for open source stuff, and lo and behold, I found Monkey, uh, and I started, you can actually see my messages from the earliest days of that still. Um, and uh, and that’s where I found it and just started asking a whole bunch of stupid questions. And, uh, and I was one of those people who was mentored by Greg Nagle via the school of Hard knocks.

And, uh, and, you know, asking dumb questions and getting and getting really concise answers back, you know, it is great and is, uh, is is a great education, uh, in so many ways. Um, cuz he did have that background that I didn’t have, you know, with, with Max. Um, so there’s a lot of knowledge there that I just didn’t have. So it was easy to, to just kind of pick his brain and dig in on that stuff and learn as much as I possibly could. But that’s how he got into all of this. Um, and then, yeah, like fast forward a couple years after that, a friend sent me a link to, to Hacker News for a position at Dropbox. I was like, why would I apply to that? They’re not even gonna respond to me. So I did and eventually got a job there, and that got me out to California.

Um, and, you know, networked and made a bunch of friends out there. Um, and that’s kind of where I’ve been ever since, you know, kind of, uh, in the, uh, the tech company, MAC management space, um, at scale, uh, you know, anywhere from, you know, 50,000 max at the, at when I left Facebook all the way down to where I am now, which is, you know, less than 50 . So 50,000 to just 50 top off three zeros there, um, . And it’s is quite a, it is quite a, quite a difference. You know, it’s a very different, uh, environment and very different considerations, uh, in all, all the ways that you mentioned. You know, like you go from doing this super specialized position, you know, making frameworks to manage all these things, to, to doing this stuff at scale to, you know, okay, now I need to care about the business and now I need to learn how to care about the business, and now I need to learn, okay, marketing makes the company money, so I should probably help marketing out and probably make sure that their sass is running well, I should probably do all these other things.

Um, you know, so it’s just kind of like this whole trail, uh, uh, here and this whole like kind of, um, uh, pivot, uh, down to a scale that I’ve never been at before, actually. So, yeah. Uh, like when I joined Dropbox, it was 300 people I think. So that was the smallest prior to this, and that’s still much different. You know, 300 is still a lot different than 50 and

Charles Edge (00:11:46):
They’d already been funded and were growing quickly. And, you know, I do feel like when we met you were a CPE at a pretty large and still growing at that point. Organization. Yeah. And as you mentioned, the the responsibilities are, are wildly different between any position and a large organization and any position in a small one, uh, almost any position, I guess. Um, so do you mind taking us through what might be on a position description at a gig, like at a big ooh firm, you know, rapidly growing, heavily funded, et cetera?

Nate Walck (00:12:24):
Yeah, so at a larger company, you might be super specialized into one area. So for instance, when I was at Facebook, I was writing almost entirely Ruby code and, you know, reversing as much as I could about Mac Os and then making it work with Chef as natively as possible. Uh, so for instance, that was the early days of config profiles actually being useful and using the profiles command in order to install them. So I had gotten to a point where I could dynamically generate the XML for that, um, and then shunted off to the profiles command to install it locally, um, and dynamically generate the whole thing, including the yid is a conflict specific yid. So if the conflict changed, I knew that the one installed didn’t match the one that we had now, and I knew that I had to reinstall it. So I had this kind of method by which I could determine the state.

And yeah, you have to have all the skills, you have to have everything from the lower level system stuff. Well, not super low level, but you know what I mean. It’s, um, it’s kind of like, how do I wrap the tooling? I need to know the tools that exist and the APIs that exist well enough in order to wrap them in a conflict management tool. And I think the reality of that is when you get to a company of that scale, imagine paying a SaaS company for 50,000 licenses of anything that’s so expensive. And from the business point of view, you look at how much that costs, you know, that might be, you know, over a million dollars, $2 million, whatever it is, depending on the company, uh, how many headcount can you hire for that? And you will get a more tailored solution for that company, for the money, and you will own it, you know, end to end.

And that’s, that’s kind of the big difference. Um, you know, now pivoting back to where I am now, I can’t justify spending that amount of time doing that. I just can’t, you know, like I literally will use whatever’s built in and if it works great, and if it doesn’t, I’ll just write a quick batch script, ship it off, job done. You know, and that’s, that’s okay because so long as I’m meeting the compliance requirements, that’s what matters. And so long as I am supporting the business on that side in the way that they need for now, then great. I don’t need to dynamically generate configs because we have, you know, 15,000 engineers that are all unicorns in their own way and need all these different settings and configurations and all this other stuff. I don’t have that. I can literally be like, all right, we have all this base stuff installed.

If you need anything else, feel free to do it yourself, , you know, because like, it’s not worth automating it for two people. It’s just not. So there’s like this economy of scale there that is different, um, between the two. So to go back to your question about the skillset, it’s, it’s more like a software engineering, not software engineering, like a production software engineer, but more of like this kind of hybrid systems engineer kind of role. It’s like coding, but not like super, I’m not writing crazy algo to make the website two milliseconds faster. I’m not doing that. You know, that’s what software engineers at larger companies do. Um, they are, they’re absolutely insane and there’s a whole range. But on the CBE side of things, it’s literally don’t break the fleet first and foremost, . Cause if you break the fleet every minute is like thousands or tens of thousands of dollars. So don’t do that number one or millions. There’s a lot of qi. Yeah. Or millions. Yeah, exactly right. Depends how bad you break it. Yeah.

Charles Edge (00:15:52):

Nate Walck (00:15:53):
, right?

Charles Edge (00:15:55):
Yeah. I saw, uh, for a managed service provider for breaking a fleet, I think their penalty was millions of dollars per hour. Um, yeah. Which, you know, I, I guess they’re making enough to cover it if they happen to do it, but, you know, um, and I think big fix, I, I I seem to remember not big fix, uh, F five, I seem to remember seeing, uh, that F five had a contract with Amazon, and this was quite a long time ago where it was like a million dollars a minute for any downtime that they incurred. So that does make sense. I mean, I, so on the Ruby side, why Ruby? I guess

Nate Walck (00:16:36):
So, um, at Facebook specifically, uh, they use chef in production, so they wanted to use it on the corpse side as well. And the reason for that is, um, if you level up your skillset and you want to move to production engineering, you have the mobility and the ability and the, uh, opportunity to do so. They do what’s called a hack a month. So if you wanna go work with another team, you talk to your manager, you talk to the manager at a team you want to go talk, uh, work on. And if you can work it out, you’ll go work for that team for a month and see if you like it. And if they all like you or what have you, and you like the work, you can, you know, initiate a transfer. If you just decide, okay, this is not for me, you can always go back to what you were doing. No, no harm, no foul. And that was kind of a, a cool mobility thing there.

Charles Edge (00:17:18):
Yeah. That is the best rationale I think I’ve ever heard for language selection, for device management specifically. You know, like they’re, they’re all about the same ultimately, but if they give you up that, yeah, I, mobility, whether you consider it upward or lateral is another story. , how

Marcus Ransom (00:17:35):
Does that work the other way then? So the ability to increase the talent pool where you, you know, need to look externally and find, um, candidates that don’t just have the domain knowledge understanding, you know, Mac OS and mdm, but also the, you know, know their way around the specific language you’ve chosen to implement in that organization.

Nate Walck (00:17:59):
Uh, so generally speaking, during the hiring process, if you can prove that you have critical thinking skills and proficiency in some language, it doesn’t matter if it’s that exact language. And like, I’ll rag on Facebook a little bit here, but there’s nobody in the entire world that writes hack. I’m sorry. There just isn’t. Facebook is the only company in the entire world that writes hack. So every engineer they hire, there’s no hack en uh, experts coming into the company unless they were at the company previously. So that’s how their bar works. It’s kind of like prove that you can think about this and, and are rational and can and can solve the problem. So yeah, we get people that have Python that, you know, think about universities. Some universities still just teach Java. Not just Java, but you know, like Java’s not as popular as it used to be. Let’s, let’s be honest. And, um, , sorry. I know Yeah.

Marcus Ransom (00:18:49):

Charles Edge (00:18:49):
The, the critical thinking thinking goal. Yeah.

Marcus Ransom (00:18:51):
The critical thinking bit is the bit that’s hard to find it. Yes. It sort of reminded me of years ago when we had Chip Pearson, um, on the podcast, and he was saying he looked for empathy because that was the thing that it was hard to teach people. And I’m guessing it’s a parallel to that where, you know, once you’ve, once you’ve deemed yourself to be a smart person who can understand what they’re doing and, um, prove that they can do things without , you know, and understand the implications of code that you write.

Charles Edge (00:19:23):
Yeah. And I guess picking up from, yeah, you know, if you’re a smart person who can potentially transition into other roles, but you still have that one role, so what’s the day-to-day look like at, at a, as like a c p E type of position in a large organization like that?

Nate Walck (00:19:40):
It really depends on the role. A lot of times it’s very much problem based. So here’s a problem, figure it out. And it might not be the same between one problem and the next one problem might need to use MDM APIs. One problem might need to be a bunch of local scripting, you know, using p and they’re completely different, uh, from problem to problem. Now that said, on larger teams, you do have a lot of folks who specialize in like the day-to-day, um, fire stuff and just like fixing, fixing things that broke because of this new version. Um, you know, improving the code base for chef or whatever you’re using, you know, chef SaltStack, et cetera. And those folks are specialized in, in more or less, it’s kind of like, it’s kind of like the opsi day-to-day side of cpe. Those, those roles definitely exist.

And the larger the org, the more folks you have like that, the smaller the org, the less folks you have like that. Um, even when, you know, when I joined Facebook at 12,000, we had a couple, we had like four people I think, that were doing the day-to-day stuff. And then, uh, we had two people that were doing the higher level architecture and long-term planning. Um, so even at 12,000 you might have that, but much smaller than that. I don’t think you, you would, I think everybody would just be day-to-day. Everybody have their own long-term projects, and that’s kind of how that would go.

Charles Edge (00:21:06):
Makes sense. And I guess having been based in the Bay Area and with companies like Dropbox and Facebook on the old cv, there’s probably a constant flow of head hunters looking to get you to consider a quote unquote new opportunity, right?

Nate Walck (00:21:22):
Yes. So with head hunters, it’s pretty all right. So I, I’ll preface this by saying I am in an extremely privileged position, and I understand that very well, . So for me, I, I live in Pennsylvania, um, I’m moved back closer to family back in 2016. Um, and yeah, like being able to, to say no to things is like a privilege that not many people have. And I completely recognize that. Um, but yeah, I look at the company, I look at what, whether it aligns some of my own personal interests and values and see if that’s a place that I would want to be. Um, but more and more lately, uh, I really like working with people I know, and I prefer working with people I know. Uh, and I think this is very common, you know, like even at my, the university, I have friends that are still there and they’re happy because they have friends there and they work with their friends and that’s what they do every day.

And there’s something to be said for that. So I tried to do the same, you know, I tried to follow folks, uh, this place I went recently, I, this is the first time I’ve walked into a company and not known someone since 2013, which is crazy. Um, but that’s how the networking works, especially within the Mac admin community. You get to know people and you spend the time, you can build relationships and, you know, and then be like, oh, now we have a job opening and I’m thinking of this person, cuz I’ve been talking to them about this other cool work they’ve been doing. And that’s how the networking works. It’s very organic, it’s very, uh, referral based. Uh, and I think that’s pretty, pretty cool about the way our community works. It’s, it’s not like when I see a head hunter, I’m almost not interested immediately unless it’s someone that’s really gonna put in the time and talk to me.

Um, for this instance, uh, I talked to the CEO for like two hours on a Sunday and chatted for a while and that’s, and that’s sold me on this. And that’s the only reason I even considered it cuz you know, I was working with Wes and Shea and all these other great people and I, and man, it is hard. Those, those decisions are never easy. Um, but yeah, so I think for me, um, yeah, kind of looking at the impact of the business, what type of impact will I be able to have there and are there people I know and, and like, and get along with already? Because having that, having that, uh, backup is super nice. And having, having those prior relationships,

Charles Edge (00:23:40):
And I guess if you decided to take a gig at a smaller company, then, especially if you didn’t know that many people or anyone necessarily, and I’m in the same boat, I don’t think I’ve had a job where I wasn’t recruited by a friend to come in since the nineties. Yeah. You know, because I’m old as hell. Right? Right. But, uh, , but how was that transition to a smaller company?

Nate Walck (00:24:04):
Uh, terrifying in a word. , you know, um, I, I’ve been good about, uh, taking risks, but only because I have support. You know, if I didn’t have support on the family side, I wouldn’t be taking risks. I would just be, you know, I wouldn’t do it. I wouldn’t even think about it. Um, but I have a lot of support there, so That’s good.

Tom Bridge (00:24:24):
That’s a great way to think about it. And, you know, getting a nudge from someone that you love, um, that’s like, you can do this. Go go and do the, I mean that my, I there’s no question in my life that, um, you know, my wife is my biggest backer. Mm-hmm. Um, and you know, she really encouraged me to take the leap to go to Jump Cloud when the time came. Um, because she’s like, you got this, you can go do this thing, believe in yourself, go do it. Go take this opportunity.

Nate Walck (00:24:49):
Meanwhile, it’s really nice in your head, meanwhile in your head you’re like, ah,

Tom Bridge (00:24:52):

Nate Walck (00:24:53):

Tom Bridge (00:24:54):

Nate Walck (00:24:54):

Tom Bridge (00:24:56):
We’re 18 months in and there are still some days where my brain is like, ah,

Nate Walck (00:25:00):
Yeah, yeah. And,

Tom Bridge (00:25:02):
But that’s totally normal. And you know, one of the things that I really want everybody to, to, to appreciate out there is that, you know, imposter syndrome’s a thing. Mm-hmm. , um, it is a real, real thing. Um, and sometimes you are far more capable than your brain is letting you believe.

Nate Walck (00:25:18):
Yeah. I I still don’t believe it. Like, people like you may not even believe me, but I still don’t believe it. Like, I just don’t, I don’t understand how I got here. I don’t understand any of that stuff. I just don’t understand. I just, I, I solve a problem when we move on to the next thing and I forget about everything that came before it because I don’t want to, I don’t wanna focus on the past,

Marcus Ransom (00:25:38):
But that’s probably a good thing though. The, the, I I’ve found the people who have that, I’ve got all of this worked out and I, I know what I’m doing, um, are often the dangerous ones because they’re not constantly questioning everything they do, whether that’s internally or externally, just knowing that someone has that internal fear going on of No, I’m gonna check that because, um, I, I really, I really don’t know whether I’m, whether I should be doing this or not.

Nate Walck (00:26:10):
Well, I mean, you know, you have those moments where you’re sitting and you’re like, this is shit. I know it’s shit, I know I’m gonna have to fix this in six months, but we gotta get this done so I’m doing it. You know, that’s, that’s just, that’s just how it goes. And sometimes you know it and sometimes you don’t, and the times that you don’t are the ones that kick your ass the most and the ones that you learned the most from. Because, you know, when you get blindsided by your own idiocy, , you’re just like, oh yeah, okay, I get it. Now. ,

Marcus Ransom (00:26:37):
I, I, I spent, I spent the morning dealing with that with, um, in install meter and the Oh, um, the, the testing, the testing flag where, you know how it is when you, when you finally

Tom Bridge (00:26:50):
That’s on by default.

Marcus Ransom (00:26:51):
Yeah. When you find for, for a good reason I might add. Yes. And when you finally see it, it’s like, ah,

Tom Bridge (00:26:57):
Uh, I, I literally played around with it for a full solid hour before I went hat in hand to Armon. And Armon would be like, I think this is amazing, but I can’t make it go. And he’s, and I said, I sent him the thing and he was like, you’re missing the debug flag. and . And, and I felt so dumb. I was ,

Charles Edge (00:27:19):
But Armon is so awesome in that very German ish way where, you know, it’s like just very factual. This is the way , you know,

Tom Bridge (00:27:28):

Charles Edge (00:27:28):
Is correct. No, no guilt.

Tom Bridge (00:27:29):
He made, he, he made me feel better about like having missed something obvious. Yeah. And that is the side of a good friend. Yeah.

Charles Edge (00:27:35):
So Armen, no guilt, thank you with him ever that I’ve encountered. So very kind.

Nate Walck (00:27:41):
I will say, like on that topic, I’ve seen people at every single level not know anything about what they’re about to go into . They’re just not, you know, the skill is learning, the skill’s not doing. And that’s what I’ve found a lot of the way, uh, you know, a lot of the times with, with higher end, you know, Suze even, but the skills learning as quickly as you can. And, and, but

Marcus Ransom (00:28:02):
It’s also this, this idea that we will, you know, something’s brand new. Things are constantly evolving. You have to do it for the first time at some time. Um, you know, we can’t have, you know, 15 years experience managing declarative MDM because

Charles Edge (00:28:20):
20 years of experience with Swift , I saw that description, I was like, oh boy, . Yeah. I, I mean, to to rephrase what you said, tech is changing so fast. I don’t care if you know mm-hmm. , I mean, I, I think there are some places where like if I’m hiring a, a true developer, I might look for specifically some kind of object orientation in their skillset, you know, because that, that’s just a hard thing to pick up. I think, uh, you know, if, if you’re coming from Bash or something. Um, but in general, yeah. It’s like, can you learn and, and do you get hives if you don’t know how to do something? Cuz I’ve had people on my teams that do, and no offense to any of them, they, but they freak me out, you know, because I’m always throwing weird stuff at people. And if you get hives every time, I’m gonna send you to the hospital within a week. But it’s also, do

Marcus Ransom (00:29:16):
You, do you want to learn? Because I’ve also worked with people that, um, I don’t know, maybe they did get hives when they were working on something they hadn’t used before. So they were trying to avoid it by only ever doing things they’d been doing for the last 20 to 30 years. And that was really challenging because, um, you know, it’s not gonna work anymore. Um, those, those days have moved on

Charles Edge (00:29:37):
And I would say, yep. You know, if, to be really fair, um, some people have different priorities, right? Like they don’t really care about the job. They want to show up, answer a bunch of phone call questions, go home and play with the kids or Exactly. You know, whatever it is. And I totally dig the priorities and the more power to them. Yeah. I could definitely stand to reprioritize things a lot more in life than I do, you know?

Nate Walck (00:30:06):
Yeah. I think as time goes on, I start drifting in that direction myself. I start drifting towards wanting to do other things of interest and like side side hobbies and, and things of that nature. I think

Charles Edge (00:30:17):
I, and then I start another book , you know? Right.

Marcus Ransom (00:30:22):
I just, I just made my, one of my side hobbies, my career. So it just kind of panned out that way.

Charles Edge (00:30:29):
And that is a thing for sure. For sure.

Tom Bridge (00:30:33):
Deploying, managing, and protecting Apple devices at work shouldn’t be difficult to require several solutions. Mosel is the only Apple unified platform for business. By combining enhanced device management, endpoint security, internet privacy and security, single sign-on and enhanced and apps management into a single apple only platform. Businesses can now easily and automatically deploy, manage and protect their Apple devices with one solution and add an affordable price with a solution for every business size and the best support in the market. Request your free account today and see firsthand why Mosel is more than an Apple mdm. Mosel is everything you need to work with Apple to learn more, visit business.mosul.com. That’s business dot mos y l e.com.

Marcus Ransom (00:31:20):
So you, you, you mentioned before, you know the, the specifics of, you know, making sure you don’t, you know, air gap a fleet of 50,000, a hundred thousand devices, which, you know, that’s a good skill to have. Um, so large organizations have a lot of change control by necessity because you want to prove that you’ve thought this through, so you don’t fall into the, well this worked the last 20 times, I’ve, I’ve done this, so it should be fine. So how have you found that’s changed moving into a smaller organization where, you know, the, the, the time it would take to, you know, initiate a change control process like that would probably take more than the entire IT department, but you still need to make sure you make considered choices or intentional choices. So how have you found that that sort of difference in a small organization?

Nate Walck (00:32:17):
So I guess this is confession time, but , the first like three or four months, I didn’t have anything checked into a source control for like my bash scripts or any of that stuff. I was so busy spinning everything up and just going at breakneck speed in five different directions that I, I just got it done and then I did, I did commit everything and now it is in source control and reviewed and landed to the Monte repo. Um, on the prod side, a lot of ex Googlers, so Monte repo very go heavy and, uh, and definitely code first. So I am being intentional about moving the corp bench side of things in that direction. When I say corp bench, I just mean me. Uh, but setting the stage , setting the stage for future hires to make sure that when we are building corporate engineering, we do keep that kind of culture and make sure that we, we do that from the beginning. I think it’s a very rare opportunity to be able to do that from the start and have other people that will support you in that. Uh, so that’ll be interesting to see how that works out. Um, I think it’ll go well, but, you know, uh, hiring people with very specific skillsets is very difficult. So we’ll see how it goes. And I might need to have more specialists and less generalists in that regard.

Tom Bridge (00:33:31):
Did you just specifically ask that you need people with a certain set of skills, a certain set of skills that might be make them a nightmare for a person like you

Nate Walck (00:33:40):
maybe. You know, it’s, it’s, it’s interesting cuz like I’ve, yeah, maybe , it depends. I, there’s some folks who are, who are really, uh, code first and, and good at that out of the gate, and that’s solid. But on the other hand, a lot of times when people are code first, they wanna focus on one thing until it’s done and they move on to the next thing until it’s done and then move on,

Tom Bridge (00:34:01):
Which is how processors work. So That’s understandable.

Nate Walck (00:34:04):
, right? I know. Yeah. They’re, they’re, they, they’re closer. They’re, they’re closer to neural link than I am, I suppose, in that regard. Um, but on the other hand, when you’re small like this, you can’t really afford to just focus on one thing and do it until it’s done. You have to, you have to juggle. And, um, so it really comes down to making sure that you, you get the right folks for that type of thing. And other people who are maybe like me, like have been at big companies and want to try it out and drive themselves crazy for a while, uh, and see how it goes. Uh, but I’ve been enjoying it a lot. And the reason for, you know, one of the biggest things that’s different about being at a smaller company is you do have a lot more impact. You do have a lot more say, you know, I’m on the culture committee for the entire company, so we get to talk about how things are, are going and how we’re doing, you know, peripheral views and what’s the philosophy behind that and what does it say to do it this way versus that way and all these other things that you would never have a say in a larger company.

Like if you want to have a say and you want to make change, real change, you have to be a C level or a VP or, or a director level at the minimum to really be able to move the needle. Because when there’s that much inertia moving it, it takes a lot to, to, to, you know, move it off that course. So that’s part of what makes this role different. It’s a lot more diverse even outside of it things, you know, I’m doing logistics for the first time and working with C D W and learning about palletizing max and drop shipping and all these things I’ve never had to do before, just never had to because we had a logistics person and I would just be like, Hey, can you go order me a thing? And they would order me a thing and to magically show up and everything was great. Um, well

Marcus Ransom (00:35:48):
You didn’t even need to tell them because it was, you know, there was a process and an automation. There

Nate Walck (00:35:53):
Was a process. Yeah.

Marcus Ransom (00:35:54):
The code would tell them that if someone’s been on board, that they need to order a thing and here’s where you get Yes. The information as to what thing and where the thing needs to be sent. Whereas now

Nate Walck (00:36:05):

Marcus Ransom (00:36:06):
That’s you on a phone or Slack, I’m guessing

Nate Walck (00:36:10):
It is. Yes. Me and me and, uh, me and Slack and, and, uh, sometimes angry emails, but only when I have to , you know, I really don’t like sending angry emails. It makes me feel bad before I’ve even sent it . And,

Marcus Ransom (00:36:23):
And have you reached that point where you’re like, I’m just gonna drive to the Apple store? Cuz

Nate Walck (00:36:29):

Marcus Ransom (00:36:30):
, yes.

Nate Walck (00:36:31):
. So especially with the last, um, couple years of course for obvious street. Yeah. Um, uh, when I joined it was November, uh, of last year and everything was sold out for like six weeks in the entire month of December. So I was just like, well, crap, what do I do? How do I, how do I prevent us from having major issues around, around this? Um, but thankfully I have other friends, uh, that I knew at Dropbox actually that are also at smaller companies. So I’ve been able to compare notes with them and that’s another community on the IT side, uh, that’s kind of outside the MACAB community, but still very similar in that regard. Um, so that’s pretty interesting. That’s been super helpful. I can just bend their ear one I need to and be like, how do you do this? I don’t know what I’m doing. .

Marcus Ransom (00:37:18):
So what things, yeah, what things have surprised you that haven’t changed? What, what are the things that you thought would be completely different but you’ve got that aha moment where it’s like, oh, this is, I’ve done this before, this is no different.

Nate Walck (00:37:31):
Oh, oh I have, I have a really great one for this. So, uh, compliance and a word. So you work at a big company here, let me paint a picture. So you work at a big company, you’re very specialized, you’re told we need to do this for compliance. And you’re like, this is stupid, why should we do this? This is terrible, blah, blah, blah. And then you eventually go do it because you don’t understand why they need to do it. Nobody wants to explain why they need to do it. So you just do it, you do your job, you go back to doing other things and then every year, you know, or or however often you have a, an audit and you talk to the auditor, you provide evidence and then that’s it. That’s all you know, that you show up, they grill you, you give them information, you leave, you’re done.

Um, but then when you’re at a small company, you actually see the business in action and you say, okay, we want customers, customers want us to have SOC two. And I said 27,001 for us to have SOC two and 20, so 27,000 a month. We need to do all these things if we don’t do these things. No customers, no customers, no money. No money, no business, no business, no job. That’s how it works. And we are at a really giant company that’s already been taken care of that’s already on, on rails, it’s already done. But here it’s like, okay, you know, we need to make sure that we have the security control supplied across all the laptops and in production and policies written down all these things. And yeah, so now I actually have a lot of uh, a lot more visibility into why compliance is the way it is. And it’s not just because the business people hate the IT people. It’s not that. It’s not just because security hates you and wants to make your life miserable. It’s not that it’s, there’s all really good reasons for it that are just several levels obscured when you’re at a larger company and several lever levels removed from you. And in a way you’ll probably never see it at a larger company ever cuz you’ll never have that type of visibility and transparency.

Charles Edge (00:39:18):
And that’s, that’s one way the role’s different. Um, are there any others or, I, I mean obviously there’s probably hundreds, but are there any other subs, substantial ones or would you say that’s the biggie, the, the breadth of what you do?

Nate Walck (00:39:34):
The breadth of what I do for sure. Um, right now I’m helping out on the product side for the Mac product that we have. Uh, and making sure that it’s packaged properly. Cuz like if I’ve winged about other vendors,

Charles Edge (00:39:46):
I’m confus

Marcus Ransom (00:39:47):

Nate Walck (00:39:48):
How, how much is my as gonna get busted if we don’t do it right? How, oh my God, am I gonna come kick my ass?

Tom Bridge (00:39:54):
The number of I I I had a very, I I I had a long conversation once upon a time with one of our packaging engineers about how we build our product and, and how it goes out. And I was like, okay cuz here are all of the things that we need to do instead. And so those are on a backlog someplace and we’ll get to them. Mm-hmm. , but like we have anything new is coming down in the right format. Anything I, you know, focused is coming down in the right format and you know, but it was like, this has to get

Charles Edge (00:40:21):
Better some someday we’re gonna have to do an episode on how various product managers prioritize backlog items and what gets picked up and what doesn’t and what doesn’t make the line. And cause oh

Tom Bridge (00:40:35):
Man, I I, the things that I have learned so far, um, that move me, uh, I feel like at some point I need to write the guide for how to write a product manager’s like feature request. Um, yeah. And uh, yeah, all sorts of good things.

Marcus Ransom (00:40:50):
Learning, learning to let go. Is that what it’s gonna be called ?

Nate Walck (00:40:55):
I would, I think

Tom Bridge (00:40:55):
It’s, it’s understanding that you are not everyone and everyone does not want the same thing. Mm-hmm.

Charles Edge (00:41:01):

Marcus Ransom (00:41:02):
You, you can’t die. I would love to see you can’t down on 12 Hills at once

Charles Edge (00:41:05):

Tom Bridge (00:41:06):
That is great . Now that’s

Nate Walck (00:41:08):
Said, I would love to see that. I

Tom Bridge (00:41:09):
Would love to see that. I know some people who are trying it and if

Marcus Ransom (00:41:13):
You get blown up into small pieces and those small pieces are scattered across various hills.

Nate Walck (00:41:19):
So that’s the other thing that’s very different. Um, working on the product side is different than working on the IT side. On the IT side. Nobody cares until stuff breaks on the product side. Everybody cares for every OID little thing you want to do do because all the time if, if you just do something and you don’t have like a request in for that, you’re wasting time and you’re not focusing on the things that need to get done. And that, that has been something that I’ve been learning that I’ve not had to do before. Because you know, it’s not that nobody cares about it, it’s just that there’s this expected baseline of things that work and it one, it needs to go smoothly and they want it. You know, that’s, that’s what they want. They want steady state. Whereas on the product side, you’re actually building something that’s going out to customers that has new functionality and you need to QA the crap out of that because once it goes out there, it’s not like, oh, I’ll just push another version. Nope. It might take you two months to get your customers upgrade to a new version depending, you know, and maybe even longer cuz like the long tail at a big org is like, you know, three to four weeks maybe at the most. But customers you don’t have access to their systems. You can’t push things for them, you can’t do all that. So it’s, some, some products have tried more intentional and

Marcus Ransom (00:42:31):
We always appreciate Yeah. Some products, you know, create their own little web servers that they’ll point themselves to to

Charles Edge (00:42:38):
Update things ,

Marcus Ransom (00:42:40):
See what they’re trying

Charles Edge (00:42:41):
To do. You sound facetious. Yes. Marcus

Marcus Ransom (00:42:44):
. Correct. Well,

Charles Edge (00:42:47):
Spotted . I’m not back dance anyways. Um, so I I do feel like at a big company you have full teams to do, you mentioned compliance, so to do compliance. Yeah. And I do feel like as you kind of alluded to, the needs are often watered down by the time they get to engineers that actually pull the levers in whatever the device management tool or other tool that that’s being used. And you, when we were writing up this uh, script, you had a great quote about that. Um, do you mind unpacking what you meant by business people don’t hate tech people? Cuz it was on a great quote to be honest.

Nate Walck (00:43:32):
Oh, absolutely. So, you know, business people don’t need tech people. They have, they have needs that need to be fulfilled in order for the business to be successful. And you know, when it comes down to it, if it’s very abstracted out and you don’t understand why they have the need, you just see it as they bought this thing, they didn’t talk to me about buying this thing. They want me to push this thing and this thing is terrible and now I hate my life for however long it takes to get this pushed out. And that’s normally how that goes. Um, everyone’s had that situation. Everyone maybe, maybe too often. Um, but when you’re closer to the business side, you can kind of see, okay, we need to start tracking X, Y, and Z to do that. We need these products for these products, we need to make sure that they integrate well with whatever we’re using for authentication.

Make sure the security’s good on that side. And there’s a lot of needs there that, you know, you need it to make a sale and making a sale to the point of having a business. So I can’t just sit there and, you know, draw a line in the sand and say, I’m not deploying this. This is trash. You can’t do that because it’s like, okay, so do you not wanna make money? Mm-hmm. , you know, what do you, what’s, what’s the goal here? And and on that side, the business is very complicated. It’s much more complicated of a system than one might imagine. I feel like there’s this very simplified view of business that people have. And until you’re right there watching it and like I, I know like, uh, Charles, you’ve, you started businesses from nothing, so you know all about this, but like, people don’t, people don’t have that experience.

I have never been an entrepreneur. I’ve never started a company and Tom too. Right. You know, um, and I don’t, I’ve never done that stuff. I, I just never have cuz I’ve always worked at a university or a big company. Uh, so you don’t have that visibility. So yeah. So back to that. Essentially if you have a customer that wants to sign a deal, okay, now you need something that you can use to sign the deal securely. Okay, we need DocuSign, we need it right now. You know, or whatever. You get it done and that’s what it is. You get it done and you make the deal happen. And, and that’s the goal. The goal is sales and it as, as much as I hate to say it, it serves the business and supports the business and it does not exist to support itself and it’s not just its own microcosm.

Tom Bridge (00:45:55):
Yeah. And, and I think that for me, the, the big thing, the, the big lever for smaller business is that it has to be an enabler. Mm-hmm. , you have to be a force multiplier in, in businesses that size is that, you know, for every person you have, you’ve got to make 50 people stronger. And you know, as, as you get into that state, whereas, you know, lord, you know, a lot of businesses may, may, may not be able to find innate and you know, they’re relying on, you know, what Tom used to be. Um, and you know, that is, uh, that it’s a, that’s another kind of trade-off. And, you know, being able to outsource to those kind of businesses is, uh, you know, a possible option for a lot of those organizations as long as they’re willing to deal with the trade-offs they come from.

Charles Edge (00:46:36):

Nate Walck (00:46:37):

Charles Edge (00:46:37):
You know, I I do feel like on the other side though, and I’ve, I’ve having been on both sides of this hundreds and hundreds of times, and in my career, luckily, and regrettably, you know, sometimes you just wanna say, trust me and we have to do this rather than have to unpack the exact same thing that you’re saying a dozen times mm-hmm. now on the engineering side, you have to say, well, I need to understand why, because that might completely change the way I write this or the way I implement this. Um, so there’s this fine lines sometimes between how many meetings do we have to get the camera on phones disabled on devices that are in clean rooms that have access to chip masks or something like that versus, you know, I, you know, whatever, whatever depth it is, because it does completely change the way that you choose to implement things.

And I know I’ve, I’ve tried when I’m on the engineering side and I’m accepting requirements to say, okay, I’m not trying to say no here, I just need to understand for technical implementation, you know, it will save a lot of time in the next two to three years if I do this along with your true intent rather than just Abu. And this is a line on a form and sometimes the auditor comes back and says, well, it just says run antivirus, so just make sure it runs antivirus. And you’re like, okay, clam AV enabled, done, you know, or whatever. Right. You know, it’s protect . Yep. Right.

Nate Walck (00:48:14):
Yeah. Define antivirus.

Charles Edge (00:48:17):
Exactly. Let’s,

Marcus Ransom (00:48:18):
It’s definitely not provirus ,

Nate Walck (00:48:21):

Charles Edge (00:48:22):
Until it is . Yeah. Those Yara rules. Nevermind , it’s,

Marcus Ransom (00:48:28):
It’s also about embracing the different personality types and different approaches to things. Whereas if, you know, engineers tried to run sales, um, in some organizations that works really well, but in some markets that would result in the most amazing product that never gets released, uh, never gets to a 1.0 release because it’s just constantly being iterated and fixed and resolved.

Charles Edge (00:48:55):
Oh, that’s easy to do .

Marcus Ransom (00:48:57):
Yeah. And if sales ran engineering, there’d be, you know, great marketing, um, great features. Just every single one of them would be on the backlog because, um, nothing would ever get done. And, and I, I know for me that was something where I had to really embrace that the people who were frustrating me, uh, much like this cat that’s climbing on my shoulder,

Charles Edge (00:49:16):
Which was very fun for me to watch

Marcus Ransom (00:49:19):
. Yeah.

Charles Edge (00:49:19):

Marcus Ransom (00:49:21):
The people in organizations that were, you know, starting to frustrate me is understanding what their motivation was, what they were trying to achieve mm-hmm. and that maybe they were, you know, approaching this task in a way that was very different to the way I would was because they were better at that, better than I was, which is why they were in that role, not me.

Charles Edge (00:49:41):
How do you always put things better? Like you ju you just rephrased , but you did it in a much more eloquent way, so thank you .

Nate Walck (00:49:52):
Yeah. And I, that’s actually something I’ve been doing much more intentionally here. You know, especially, it’s like someone has a request and I try to understand, you know, all right, so what’s the goal? You know, what, what do we want to do and why this product and what makes this one good? And how can I help make sure that this is smoothly for you? Um, and that’s kind of how I, how I want to approach things. I don’t want to be a blocker on things. Cuz the truth of the matter is if you’re a blocker, they stop asking. They stop talking to you. They just do it. And that’s true.

Charles Edge (00:50:22):
And, and here’s something that hopefully gives you permission to make bad decisions no matter what decision you make in three years, if everyone, if everything works out well, and there are thousands of people at the org, there will be people sneering at the decisions you made no matter how good or bad they are. Which isn’t saying you should just rush into things and do things right. But, you know, that’s just the nature of hypergrowth where there will be specialists in fields that you’ve not spent more than an hour thinking about at this stage and decision. And, and they will take over something that a decision you make changes, you know, they’re mm-hmm. what they do.

Marcus Ransom (00:51:06):
Seeing, seeing something you labored over and built and created and was so proud of, get ripped and replaced,

Charles Edge (00:51:13):
Um, with a sneer, not just rich and replaced mm-hmm. . But while fun of you, .

Nate Walck (00:51:19):
I’m completely numb to that because no joke, whenever something I touched at Facebook breaks something I get messaged by my former team there, with a gif that says, blame Nate . And, and it’s from, uh, I think it’s from Malcolm in the middle, and he’s like, Nate . And, and I get that every single time I’m completely numb to people hating decisions I’ve made. Now they, they’ve basically worn me down to nub on that side. And

Marcus Ransom (00:51:47):
The good thing is, is if there’s none of your codes still in production, then you can’t get blamed when it fail. That’s

Charles Edge (00:51:52):
Right. Deprecated

Marcus Ransom (00:51:53):
Code doesn’t.

Nate Walck (00:51:54):
That’s exactly it.

Marcus Ransom (00:51:55):
Air gap fleets. Well, as long as it’s deprecated completely.

Nate Walck (00:52:00):
Yeah. And I’m, I’m very cognizant of the fact that yeah, like decisions I made a year ago or two years ago, you know, uh, you know, a year into the future, two years ago, I will hate myself. I’ll be like, why did I do that? Who did this? And then, you know, you get blame yourself and you’re like, oh, it was me. Ugh. And that, that just happens.

Charles Edge (00:52:17):
The second it’s committed to GitHub or GitLab or whatever. I don’t want to preclude any potential future sponsors . But the sec

Nate Walck (00:52:27):
S spn.

Charles Edge (00:52:28):
Okay. Yeah. I do want to preclude a couple of potential exposures now that you say that. But, uh, but the second it’s committed, it’s technical debt , like it is hard stop. Like you pick it up six months later and either APIs have changed or your knowledge has progressed. Not that mine never has, but, you know, hopefully yours does. Um, but yeah, it’s, you know, things are just constantly evolving. Like, like we talked about in the very beginning of the episode

Tom Bridge (00:53:01):
Here at the Mac Admins podcast. We wanna say a special thank you to all of our Patreon backers. The following people are to be recognized for their incredible generosity. S Stu Bakka. Thank you. Adam sbe. Thank you. Nate Walk. Thank you Michaels. Thank you Rick Goodie. Thank you. Mike Boylan. You know it. Thank you. Uh, Melvin Vive. Thank you. Bill Steitz. Thank you. Aus Storyville. Thank you. Jeffrey Compton, M Marsh, Stu McDonald, Hamlin Cruin, Adam Berg. Thank you. AJ Petrek. Thank you. James. Tracy, Tim Pert of two canoes. Thank you. Nate Sinal, will O’Neill Sebash, the folks at Command Control Power, Stephen Weinstein, CHES Wa out. Daniel McLaughlin, Justin Holt, bill Smith, and Weldon. Dod, thank you all so much and remember that you can back us if you just saw head out, out to patreon.com/mac ADM podcast. Thanks everybody.

Charles Edge (00:53:57):
So taking your experiences at, at Big Corp, and I’m not saying Evil Corp cuz none of those companies seem evil to me. Um, although they might, some people, you know, what are a few things you can think of that would let others at big companies work with people in the business or, or business people or analysts?

Nate Walck (00:54:18):
It, it’s difficult, but, uh, try to peel back the onion and if people are not being cooperative, try to do the mental exercise yourself. Okay, so, um, they want this, what if I don’t do this? What happens? And then think through that entire logic chain. Um, and that’s hard to do because you don’t, you have limited knowledge, so you might need to ask questions, be like, Hey, so I don’t understand why this is, you know, so urgent. Is there something here that I’m missing around this? And how can I better understand this need? Um, you know, to help me prioritize this, essentially, you know, cuz I have to prioritize this alongside all the other tech did over the last, you know, 10 years or whatever. Um, so just asking questions, being curious. And of course being respectful. No hot takes no spice. You know, if you, if you have hot takes and spice, you’re not gonna get very far.

It’s just the truth of the matter cuz people will just shut down in, in 500 milliseconds, you know, they’ll be done. Um, so yeah, you know, being curious I think is a, is a really big part of that. And trying to understand, um, what the reason is for the things that are being asked. And a lot of times, like a lot of times people ask for things and they are handing you the solution, but if you talk through it and understand the actual need better, you can come to a better solution. You know, it’s kind of like, um, uh, hypothesis and synthesis, uh, and that form of, you know, Socratic reasoning and talking through things. It’s just like, you know, you can come up with a better solution by working through it and talking through the problem and, and figuring out where the edge cases are and, and how you might be able to do it better.

If you’re not very curious, then yeah, it’s gonna be rough cuz you’ll have these dumb asks and you’ll just do it and then they’ll get used to you just doing it instead of being a partner. You’re just being an enabler and a doer. And, and if you enable people who are have terrible asks, then they’ll just have more terrible asks. Whereas if, if you, if you show that you care, I think that you get a lot more, you get better relationships and more respect there and therefore they’re more willing to listen to you and hear you

Charles Edge (00:56:26):
Out. Good answer. Can you think of any other ways that we in general, I guess, can be easier to work with as nerds who maybe aren’t always, you know, like, because ultimately we need a, a discreet set of requirements and I find that if someone is working with an attorney, which a lot of SOC two for example, compliance, which I think is what you mean, or iso compliances. Yeah. Go through people with those kind of backgrounds. Like they’re not coming to us with highly technical needs. They’re, they’re effectively repeating what they read in a thing. You know, so how can we be easier for them?

Nate Walck (00:57:10):
I think being curious helps here as well and asking about the, uh, the compliance side that you’re trying to fulfill and understanding that better. And maybe even doing the research yourself. But, you know, like joking, not joking, like learn triangle breathing and maybe do that you when you get bad requests. Like that might be helpful. Um, , uh, mindfulness, whatever you need to do. Um, but no, but it’s more seriously, I do think that a lot of times it gets like, or, or corbe or whatever you wanna call it, they get this, this, uh, this reputation for being, you know, very grouchy cuz they’ve had to do all these things that they didn’t want to do. And I think understanding, understanding the other side and being more empathetic helps a lot with that. But like, you can’t just be empathetic. So it’s like, how do you be empathetic and, and I think just asking questions that are not accusatory is a good way to do that.

And, and trying to say, Hey, I, we have this, does that satisfy this control and then work with them, you know, work with it on them together. Um, I think another, a good example here, relevant experience. I worked with an IP lawyer when I was at Facebook when I was trying to open source stuff and talk about a disconnect. One, I’m not a lawyer, two, I don’t know anything about patents in ip. I just don’t. So we, we literally sat down and they’d be like, does this do this? And then I would be, I would say, I don’t think so, but what do you mean by this? And then just having to dig in and like, define even the terminology just to get through cuz like I didn’t understand the terminology and they did and vice versa. They didn’t understand my terminology. So it’s almost like, kind of like, uh, the start of a really good, I dunno if you’ve listened to many good debates, like, like very philosophical or or scientific debates. But they will define terms at the beginning just to make sure that they’re talking about the same thing and they’re connecting on the verbiage. Cuz everybody can have a different definition for different words. So I think that’s very important, just kind of getting on the same plane and making sure that you’re understanding that it,

Charles Edge (00:59:08):
It depends, doesn’t really work for patents, does it? ? No, no, no, no. . Um, and if you read an rfc, they are very clear about what sh what the word shell or must means. And you’re like, wow, that was a lot of time spent on the word shell. But then as it occurs later in the document, you know, you have a very definitive understanding. And as someone who did go to law school for a little while, you know, they, it it’s just a different mindset and, and not all together. Like when, when you’re negotiating a contract, it’s like, well I’ll give you that if you give me something and you’re like, in engineering, it’s more like, okay, you told me what you need. I have time, I will do it. Not I will do it for this quid pro quo down the down downstream somewhere. You know, it’s, it’s just a very different kind of, um, in the way that, that we communicate. I did always find that bribery helped quite a bit. Like, oh look, a bottle of wine showed up on this lawyer’s desk.

Nate Walck (01:00:15):
in in it. Not in law. Just to be clear, ,

Charles Edge (01:00:18):
Right? Lawyers earn a lot of money. They need a lot of bottles of wine. It

Nate Walck (01:00:25):
No, just, just very, very old bottles of this

Charles Edge (01:00:28):
. So I thank you so much for, for going through all of this. It’s, it’s, it is a very unique journey. I mean, having been sitting at that place where the wrong click of a button would impact tens of thousands of devices, but then on the other side, the wrong choice could impact the business. Mm-hmm. and they both probably have an equal impact on your livelihood down the road. You know, it’s just a, a, a different, um, a a completely different, uh, scope, you know, for lack of a better word.

Nate Walck (01:01:10):
And, and, and if you want to be really, really cynical for just a second, you could say if I break the 82 1 x profile, they can always tether to their phone . But if I, if I break something on the business side, they can’t just do something, plan B, you know? So like on the tech side, there’s always an out, almost always an out

Charles Edge (01:01:30):
Ish. But I, I have hit a button and had thousands of machines that, that where I broke login window ples and thousands of machines couldn’t log in. never did that again.

Nate Walck (01:01:40):
I can’t even talk about some of that stuff. I can’t even talk about some of that stuff. , you, you’ll, you’ll have to, you’ll have to liquor up some of the Facebook people to get some really good stories.

Charles Edge (01:01:48):
, that’s not hard to do. Cause when you do it three times in a row is when it becomes a real

Tom Bridge (01:01:54):
Problem. What is they, what is it they say? Once is, uh, once is ha is accident twice as chance. Three times as enemy accident . So three, three times his, uh, it department .

Charles Edge (01:02:07):
So Tom, we do have a bonus question and it changed in the last minute just to throw Nate off his game. No pun

Tom Bridge (01:02:15):
Anything. Well, so if you had a day with nothing, I mean, I mean like, no responsibilities, uh, you know, for me, uh, the other day my wife took my son and like they went off and did a thing and I had like four hours of unsupervised time. It was unbelievable.

Charles Edge (01:02:30):
So you did laundry and repaired things around the house, ,

Nate Walck (01:02:33):

Tom Bridge (01:02:34):
To God, I did. I did the dishes, right? Yes. Um, I did, I took care of the dishes. I then sat down and, you know, made, you know, made the Christmas plan. Um, so, but, but then totally goofed off for a little bit. But, um, so if you were allowed to only play a game, so I was gonna say, you, you can’t go and do those things that are on your list. Exactly. What game would you go play?

Nate Walck (01:02:58):
So I have, I have a clarifying question here. Yes. Can I listen to podcasts while I’m playing the game?

Tom Bridge (01:03:04):
Of course.

Nate Walck (01:03:05):
Okay, so then that’s an easy answer. That’s satisfactory. Um,

Charles Edge (01:03:09):
Multitasking is

Nate Walck (01:03:10):
Pretty, I will just, yes, I will listen to podcasts and play satisfactory and just, just zen out on that. That’s a lot of

Tom Bridge (01:03:18):
Fun. Satisfactory. Tell me more.

Nate Walck (01:03:20):
Okay, so, um, it’s like, uh, ooh, I can’t remember the name of the other game, but it’s like a 3d, it’s a third, uh, 3D first person perspective game where you build a giant factory and it’s, it’s um, it’s very pointed. Uh, you’ve got sent into, you’ve gotten sent to this planet and you work for a corporation and your job is to extract as all the resources from the entire planet. And they treat you like property. So if you ever get hurt, they’re like, company property damage, detective , you know, and stuff like that. Oh no. So it’s like, oh, you know, but the point of it is, um, you harvest materials, you make things and you make more widgets and use those widgets to make other widgets. And there’s conveyor belts and there’s like Jetsons tubes where you can like jump in and like fly across the map and all types of cool things like that. So it’s

Marcus Ransom (01:04:09):
Really just like being a client platform engineer. Really.

Charles Edge (01:04:12):

Nate Walck (01:04:14):
Except, except, uh, except I’m the only one there to see my failures , you know, so it’s all good. Um, but yeah, it’s, it’s a lot of fun. It’s kind of like, um, it’s like a Dyson sphere program, if you’ve ever played that. Mm-hmm. or, or any of the other, there’s another one that’s 2D and I can’t remember the name of escaping me. Um, but it’s very similar. It’s like a resource generation All right. Kind of thing.

Tom Bridge (01:04:34):
Awesome. How about you, mark? Can you

Nate Walck (01:04:37):
Clip game on crack? I don’t know. Yeah,

Tom Bridge (01:04:39):
It’s a hard

Marcus Ransom (01:04:40):
One, hard one for me. I’m, I’m not a gamer, so I’ve,

Charles Edge (01:04:46):
I mean, a game would be playing with the cat, I

Marcus Ransom (01:04:48):
Guess. Well, yeah, that’s like . Well this, this is, this is the scenario I’m in at the moment is the, the family of all golf. But that looks like the post. And so the game, I’m, the game I’m playing at the moment is let little daisy not destroy stuff. Um, and

Charles Edge (01:05:02):
Keep her alive. Cuz she can’t get hurt on your watch.

Marcus Ransom (01:05:05):
No, exactly. . It’s like, it does need to be a cute, adorable little kitten here on

Charles Edge (01:05:11):
And it’s not like one of those cartoon home. Yeah. It’s not like one of those cartoons where you can go get a replacement and pretend like it was the one. Like that’s not a,

Marcus Ransom (01:05:19):
It’s not , it’s not like the love birds that we took home from kindergarten for the holidays to look after and were told that if something happens to them, it’s like, oh, just go and get another one from the pet shop and keep the receipt. And like, this has happened before, hasn’t it? ? It’s like, yep.

Nate Walck (01:05:35):
So, so we’ll call that cat herding simulator. Yes. I think that’s what that would be.

Marcus Ransom (01:05:39):
I feel like we got Yeah, pretty much

Charles Edge (01:05:42):
. I I feel like a, I should write that. And B how about you Tom?

Tom Bridge (01:05:47):
. Well, so I’ve been looking for new games for a little bit. I’ve been, I’ve been playing some older games on the Xbox, uh, cuz I just got an Xbox Series X in February and I’ve been trying to play some more time, spend a little bit more time away from this screen on a different screen. Um, you know, doing

Charles Edge (01:06:07):
Something less stressful. Right. Because gaming is way less stress. No, it’s,

Tom Bridge (01:06:11):
Well, and that was the whole thing, you know, I played World of Warcraft for a long time and it felt like having a second job. Mm-hmm. . Um, and so I kind of stopped that, uh, you know, last year. Uh, and finally I’ve relapsed twice in 10 years. So, uh,

Nate Walck (01:06:24):
I might have been up until two in the morning last night playing World Warcraft with my friends maybe.

Tom Bridge (01:06:28):
Yeah, I was gonna say, that has happened to me before. It is perfectly fine. Mm-hmm. , I just can’t do it anymore. Um,

Nate Walck (01:06:34):
I only play his friends, that’s the rule. Oh, of course. No, no silhouette.

Tom Bridge (01:06:37):
No, Michael, I was gonna say play with friends is a good, is a good time. It’s, it’s a lot like going out for a round of golf or something like that. So, you know, totally, totally down with that kind of social gaming thing. Um, I have fallen into playing Star New Valley for the first time, uh, of late. Yes. And that game is surprisingly addictive. Um, and honestly a little bit fulfilling. I’m looking for a little less grim dark in my gaming. I’m looking for a little bit more positivity. I’ve always enjoyed, you know, the animal crossing of the, of the world, although I’ve kind of reached my limit on, on that particular piece of it for the moment. Um, but, you know, I love resource games. I’ve been kind of hoping that there would be a return to like, the strategies of the world.

The first internship that I ever had was working for a PR company in San Francisco the summer between my junior and senior year on Age of Empires when it came out to the market. And that was when Microsoft was opening up the Metreon store or the, the store in the, uh, oh gosh. Um, there is the big mall that is down there, I guess, I guess it’s the mat. Yeah. Uh, they’re now sadly defunct and gone and torn down and it’s probably like an Uber factory or something now. I don’t know. Um, but, uh, that, that building is gone. It was a lot of fun to go put up that Microsoft store. Um, and, you know, lots of playing around with, uh, with of age, age of empires. I enjoyed the heck out of that game. I’ve also been playing entirely too much civilization. Six. Ooh.

Charles Edge (01:08:04):
Um, now you got me. Yeah. .

Tom Bridge (01:08:06):
Yeah. I was gonna say now I, now I, I could tell I I’ve peaked Charles,

Charles Edge (01:08:09):
But you know, one day is not enough for six, so

Tom Bridge (01:08:13):
No, no. Correct. You cannot finish a game of siv six in less than like, I don’t know, 40 hours.

Charles Edge (01:08:20):
I guess if you only did like two or three opponents in Conquest, you might be able to take ’em out. Yeah. But ,

Tom Bridge (01:08:26):

Nate Walck (01:08:27):
I do not start SIV unless I’m ready to make an investment. .

Tom Bridge (01:08:31):
But that’s like my, that’s, that’s my turn my brain off game at the end of the day because it’s just like, all right, cool. I’m just gonna like wander around. Ooh. Resources. One more village. Let’s go get

Charles Edge (01:08:41):
The Village. One more turn.

Tom Bridge (01:08:43):
One more turn. I, uh, oh my God. The one more turn on that game is dire . Uh, and yeah. All kinds of bad.

Charles Edge (01:08:51):
I, but yeah, so I would say I have been a huge Zelda fan and you know, three, four years ago I had started writing way too many books at once and now I’m done. Um, so maybe it’s time to finally tackle Breath of the Wild. I’ve been putting it off.

Tom Bridge (01:09:11):
You should do it. It’s so good.

Charles Edge (01:09:14):
Yeah, so that’s probably where I would go with that. Although ultimately I’m probably too lazy in which I’ll sit around playing Tetris for eight hours.

Tom Bridge (01:09:23):

Nate Walck (01:09:24):
Te did, did the Tetris on the Switch, were you, uh, your versus a 99 other people?

Charles Edge (01:09:29):
No, I’d loaded up on a, uh, a I B m Good

Tom Bridge (01:09:33):
Old fashion One

Charles Edge (01:09:34):
Game Boy. Yeah. Or a Game Boy . Yeah. Although the Battery would never last on a Game boy that long , you know, like Yeah. Uh, on an Apple two maybe, you know, . So I’ve

Marcus Ransom (01:09:50):
Just realized what the game is that I’ve been hoodwinked into purchasing. It’s, I’ve just

Charles Edge (01:09:54):
Realized I’ve straight, I’ve, I’ve

Marcus Ransom (01:09:55):
Gone and bought myself a Tamagotchi. Haven’t

Charles Edge (01:09:58):

Tom Bridge (01:09:59):

Charles Edge (01:09:59):
Yes. That is truly what kittens are. . Yep, it is. Although they’re a little more expensive no matter how expensive the Tamagotchi cat was. Even, even

Marcus Ransom (01:10:12):
For even for a rescue

Charles Edge (01:10:14):
This. Yeah. And they don’t clean their own litter boxes. That would be the, I know. They, that would be So the product manager of Cats, we really need to push this as a feature request for Cats won’t clean their own litter box. Um, and also a feature request for dogs would be, won’t try to raid the litter box when no one’s working. . Yes. Cause that’s cause that’s nasty . It is. And my dog doesn’t believe me anyways.

Nate Walck (01:10:47):

Charles Edge (01:10:48):
I’m a cat person. . Yeah, we are. Regrettably both. So

Tom Bridge (01:10:54):
. Well it’s been another wonderful episode of here, of the Mac Admin’s podcast. And Nate, I’d really like to thank you so much for coming on tonight. If folks wanna find you on the internet, where should they go? Look,

Nate Walck (01:11:04):
Thanks for having me. It’s been great, uh, being able to be here and chat. As far as social media, I don’t do a whole lot these days, to be honest. Honest Slack, Mac admin, slack is still the best place. Um, Twitter, not so much. Facebook, not so much. None of those really. I am on a Mastodon, but Slack is the best place.

Tom Bridge (01:11:25):
Cool. Fantastic. Well, thanks so much for joining us week. Thanks so much for our awesome sponsors this week and Mosel. Um, thanks so much. If you’re reading this wonderful transcript, we are looking for a new transcription sponsor, so if you know anybody, we’d love to talk with you. Um, and, uh, thanks everybody. We’ll see you next time. See you next time. See you.

Tom Bridge:
The Mac Admins Podcast is a production of Mac Admins Podcast LLC. Our producer is Tom Bridge. Our sound editor and mixing engineer is James Smith. Our theme music was produced by Adam Codega the first time he opened GarageBand. Sponsorship for the Mac Admins Podcast is provided by the MacAdmins.org Slack, where you can join thousands of Mac admins in a free Slack instance. Visit macadmins.org. And also by Technolutionary LLC: technically, we can help. For more information about this podcast and other broadcasts like it, please visit podcast.macadmins.org. Since we’ve converted this podcast to APFS, the funny metadata joke is at the end.



Patreon Sponsors:

The Mac Admins Podcast has launched a Patreon Campaign! Our named patrons this month include:

Rick Goody, Mike Boylan, Melvin Vives, William (Bill) Stites, Anoush d’Orville, Jeffrey Compton, M.Marsh, Hamlin Krewson, Adam Burg, A.J. Potrebka, James Stracey, Timothy Perfitt, Nate Cinal, William O’Neal, Sebastian Nash, Command Control Power, Stephen Weinstein, Chad Swarthout, Daniel MacLaughlin, Justin Holt, William Smith, and Weldon Dodd

Mac Admins Podcast Community Calendar, Sponsored by Watchman Monitoring

Event Name Location Dates Format Cost
XWorld Melbourne, AUS 30-31 March 2023 TBA TBA
Upcoming Meetups
Event Name Location Dates Cost
Houston Apple Admins Saint Arnold Brewing Company 5:30pm 4th March 2024 Free
Recurring Meetups
Event Name Location Dates Cost
London Apple Admins Pub Online weekly (see #laa-pub in MacAdmins Slack for connection details), sometimes in-person Most Thursdays at 17:00 BST (UTC+1), 19:00 BST when in-person Free
#ANZMac Channel Happy Hour Online (see #anzmac in MacAdmins Slack for connection details) Thursdays 5 p.m. AEST Free
#cascadia Channel Happy Hour Online (see #cascadia channel in Mac Admins Slack) Thursdays 4 p.m. PT (US) Free

If you’re interested in sponsoring the Mac Admins Podcast, please email podcast@macadmins.org for more information.

Social Media:

Get the latest about the Mac Admins Podcast, follow us on Twitter! We’re @MacAdmPodcast!

Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.

Back MAP on Patreon

Support the podcast by becoming a backer on Patreon. All backer levels get access to exclusive content!