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December 13, 2022 · 46 min read

Season 2, Ep. 25 – Our outlook on remote and distributed work

In this episode, Faith, Teja, and Abbey sit down to talk about the changes made prior to going remote, the numerous benefits of distributed and remote teams, and why it’s totally okay to tell people you love your job. A few other tangents will keep you laughing through this one.


Read transcript

Abbey (00:05):

Teja, what was the shirt you were wearing in the recording with Chris? I was like, somebody looks fancy today. It was like a white shirt with like a nehru collar.

Teja (00:16):

Oh yeah. Yeah. So I was still, I went to Arizona for like a wedding, just like a Desi wedding. Like a Pakistani wedding. We wore the kurta, which is like, that’s like what it’s called, just like that shirt with the nehru collar. And I was like, this shit is actually comfy and fly as fuck. So I just wore that on that day.

Abbey (00:36):

It looks awesome.



Faith (00:38):

I love that that’s the thing you notice, I don’t even–I talked to him for like an hour and I did not notice the swag change.

Teja (00:45):

Well, cause we’re just, you know, we’re just talking, so it’s like hard to notice that stuff. Yeah. You know, but it, I guess if you’re watching,

Faith (00:53):

I also like, don’t pay any attention to men’s fashion. I think it’s one of my only, like bad personality traits is like, I don’t, I don’t notice what dudes are wearing.

Abbey (01:02):

<Laugh>. I got to finally give my card to somebody, which is very exciting.

Faith (01:08):

No way. You brought cards to Denver with you?

Abbey (01:10):

I put ’em in my wallet. (Faith: Oh, nice.) And I was sitting next to this couple and they were like, oh, you know, do you work for a remote company? And I said, yeah, you know, we do like tech hiring for like mid to senior level software talent, like a freelance marketplace. And she was like, ‘really? I’m a CTO.’ (Faith: AH!) Do you guys have DevOps people and stuff like that? Like, I need someone not necessarily full-time. I was like, ‘Girl, our wheelhouse!’

Faith (01:36):

Do we have DevOps people who can help you out, not necessarily full-time? Indeed we do. Yeah. That’s our website copy <laugh>.

Abbey (01:45):

I’m making an ad.

Teja (01:47):

That actually, like how you articulated that, that’s like so clear. That’s clearer than I articulate it. So kudos.

Faith (01:55):


Abbey (01:55):

I got words.

Faith (01:56):

Sometimes I feel like I’m so on point with how I explain what I do for a living. And other times it takes me like three or four tries. I’m like, why? It’s literally my job.

Abbey (02:07):

<Laugh>. Yeah.

Teja (02:08):

You know, ok. You know what, you know what the vibe is like? So if somebody’s not excited about their job, I feel like an asshole for being excited about mine (Faith: Mm-Hmm. <affirmative>), you know? If somebody’s like ‘I work here and it’s like, okay.’ I feel weird being like, ‘Well I love what I do. I get to work on a tech platform that gets mid to senior level engineers hired. And it’s amazing cause we all work remotely and it’s like everybody’s smart and it’s a really exciting industry.’ And they’re like, ‘Okay, that’s cool. I guess.”

Abbey (02:43):

I feel like I’ve had enough jobs that I hated that I’m totally fine being like, ‘I like this one.’ <Laugh>

Faith (02:50):

<Laugh>. Your friends are used to being like, ‘Is Abbey okay?’

Abbey (02:54):


Faith (02:55):

I was at a Christmas party last night at a friend’s place and she’s a business manager for all kinds of country artists. And so everybody there was in the music industry too. And in those contexts I’m kind of like, like everyone’s bitching about their jobs and man, it’s so high pressure and working with artists and you know, the music industry doesn’t pay anything, blah, blah blah. But like, deep down, they actually think what they do is the coolest. And so when people ask me what I do and I’m like, I actually do something really cool and explain it to them, they’re all like, that sounds lame as hell. <Laugh>. You know? It’s so weird. I’m like, you guys don’t like, you don’t like what you do. You know? And all the things you’re complaining about I don’t have to deal with. But I don’t know. Jobs are weird.

Abbey (03:42):


Teja (03:42):

That, yeah, totally. What’s a good way to be excited about your job but not come off like you’re bragging? What’s a good articulation framework?

Faith (03:51):

I’m a bad person to ask because I brag. Like that’s like, something that’s true about me is like Faith’s a bragger. She’s a big old bragger.

Teja (04:01):

<Laugh>. Alright. Are y’all humble braggers or just straight up braggadocious? Like ‘I’m the shit.’?

Faith (04:08):

That’s a good question for like, maybe my most honest friends. Maybe we can get one of them on and you can ask them. I don’t know. I feel like humble bragging is like dishonest. It’s like, no, if you like something or you think you’re good at something, just say it. I can’t imagine Abbey being a bragger though.

Abbey (04:24):

Oh no. I feel very uncomfortable doing that. <Laugh>.

Abbey (04:28):

And it’s one of those, which is weird cuz it’s like, I talked to people who are, you know, like we were somewhere the other day and there was this little craft fair and this, this check was selling earrings. And one of the pairs of earrings I got was like 25 bucks and the other pair was like 50. She was like, ‘Sorry, those ones are more expensive.’ And it was like, ‘Don’t apologize, this is your work. Like–own it. These are cool. I wanna pay for this.’ (Faith: Mm-Hmm. <affirmative>), but I would not do that for myself. I dunno. <Laugh> Weird juxtaposition.

Teja (04:55):

Do you accept compliments well or no?

Abbey (04:58):

I’ve gotten better, thanks to therapy.

Faith (05:02):


Teja (05:05):

Okay. I, I’ll send you, I’ll send you guys the sick interview that I listened to by this dude, Kapil Gupta. He was having this interview with this dude Kapil Gupta, and he is very similar. And what’s really interesting about him is like he has a, he has a point of view, like I’ve done therapy. It’s, it’s helpful, but he has a point of view on therapy, which is, which is super interesting where he’s like, once you kind of process like the trauma and like you understand it, continuing to rehash and re-litigate and bring a lot of things back to it. Like you’re reliving the trauma every time.

Abbey (06:22):

Oh, lucky for me. I’ve got years worth!

Teja (06:26):

<Laugh>. Yeah.

Faith (06:27):

Abbey’s like ‘We’re not even through the greatest hits yet. We’re not doing reruns here.’ <Laugh>.

Teja (06:33):

Yeah. It’s really interesting. Like his, I mean, his whole takeaway is like, if you can observe your mind like an organ and you can observe it just like you observe like your heart or your lungs and it’s like you realize the thought pattern that it’s going in. Like is it even valid? You know, is like the neural pathways that you’ve really trained? The anxiety, or the whatever–in my case it’s anxiety–it’s like, is that, do you even want to honor it while like talking about it? Not suppress it, but just like observe it and just be like, okay. Like–

Abbey (07:07):

I mean, I’ll be honest, like when, when I got to the airport today and I got off the plane, I was like, oh God. I immediately was anxious over being back in Denver because I haven’t been gone very long. And I was like, just sit with this, just sit with this. And on the train ride into the city, I was like, nevermind. I don’t miss it here. <Laugh>

Faith (07:29):


Teja (07:31):

Were you, were you anxious? Cause you were like I maybe we made a bad decision? (Abbey: Yeah.) or were you just like, you don’t like, okay.

Abbey (07:39):

I mean, I’ve been battling a lot with home sickness, which is like yeah. It’s neither here nor there. It’s a, I think it’s a fact when you’ve lived somewhere for 20 years and leave, but (Faith: mm-hmm. <Affirmative>), I kind of got over it and then got on a plane and now I’m here. I was like, ‘Am I gonna feel all that again?’ And the answer is no.

Faith (08:00):

Yeah. I also feel like moving now is, it’s interesting because like previous to the world largely embracing remote work, moves–I would assume–a huge percentage of moves were because a job change happened, and in those cases there’s not as much pressure to make the right decision in terms of place because you’re going there because that’s where your place of employment is, right? Like it’s, it’s associated with a job, which then takes pressure away from you for like making the “right choice” of the place to live. (Abbey: Yeah.) And now that we’re in this space where, you know, our team is remote, we can really live wherever it’s like online dating, you know, <laugh>, there’s like endless options. And so like the Yeah. The anxiety around, like choosing the right one and the pressure to make a perfect decision is real, I think. And that’s a–I don’t know, I think that relationship is interesting. I’d be curious to see if other folks feel like that.

Abbey (09:02):

I think it is, but it’s also like on the flip side of that is like, being able to work remotely gives you the freedom to test those boundaries. (Faith: Mm-Hmm. <affirmative>) To be able to try somewhere new. Yes. With like the–I feel like calling a job a safety net is like really a lame way to describe it. Considering we all just talked about how much we like our jobs <laugh>. But it’s like to be able to have that, that safety of like, I can go explore places, I can check this out, I can see somewhere new and I still can be gainfully employed. (Faith: Mm-Hmm. <affirmative>), it gives you a lot more freedom to kind of like find what works. (Faith: Right.) If in a couple years I don’t like where I live, there’s nothing–there’s nothing about working for Gun that stops me from moving somewhere else.

Faith (09:46):

Mm-Hmm. <affirmative>. So I guess it’s like, it’s interesting cause I would file this under both benefit and liability of embracing remote work, right? Like (Abbey: Yeah.) The benefit is you can work from wherever and the liability is you can work from, from wherever. And so like what if we just like never feel settled because there’s so many options.

Teja (10:05):

Yeah. <laugh>, that’s, that’s, yeah. It’s interesting because, so in the first like couple years of like working on Gun, I remember feeling like, like kind of unsettled in Nashville. Because you know, it’s just like when you, when you’re working a lot, you don’t really have time to like develop deep social bonds and you can only, you know, like I think as the years have gone on, I’ve become like more comfortable, like being my work self and like the, the difference between my work self and my personal self is like pretty minimal these days, for better or for worse. But I think in the early years, like I would show up a certain way at work and it’d be kind of like, it’s different than like how I was. Plus, like, not having any friends really. Or like being able to really hang out a lot cuz you’re, you know, you’re working and (Faith: Yeah.)

Teja (10:55):

just focused on it. I found that like, if you can develop really rich social connections and you have like, you know, things to do every night or you have things to look forward to, dinners, things like that. It’s like, most places are great, you can live anywhere, you know? But, then the question is like, based on, at least for me, it’s like, based on where I wanna be are the like, baseline activities that people wanna do aligned with what I wanna do, if that makes sense. You know, so like my social circle here in Nashville, like, we train jiu-jitsu, we like to, you know, cook good food and grill. Like, you know, I’m not super into the Broadway scene that, like, doesn’t matter to me, you know? But I think if we had lived in Denver, I would’ve probably been like really good friends with people who hiked a lot and, you know, all that shit. So it’s not much here. It’s not many mountains here. So <laugh>

Abbey (11:55):

Yeah, the mountains are actually surprisingly far from Denver. So hiking is like a full day event.

Faith (12:01):

Oh, it’s a commitment.

Teja (12:02):

Totally. Yeah. The Front Range is pretty close. Go hit that Bierstadt or something.

Abbey (12:07):

I mean, where I was, where we were living before we moved was like we backed up to mountain parks but we weren’t in the city.

Teja (12:15):

I wanna go back to Telluride or Durango. I met an older gentleman on the plane to Arizona. He was looking like a freaking cowboy. And oh, this is actually a really good story, I’ll tell you guys. So, so this was like Thursday morning and I had stayed up really late just like wake up and our plane leaves at like 6:55. So I wake up at 4:00 after going to bed at 2:00, and I’m like, I’ll just snooze for like 30 minutes. And then I was like, wait, what am I doing? I have a flight to catch. So I pack, get everything ready and drive to the airport and there’s like 30 minutes before the plane leaves at this point. And I’m in the TSA line. And so I’m like getting into the line.

Faith (13:01):

We gotta get you precheck, first of all.

Teja (13:04):

I have precheck, but–okay, but, but with my name, sometimes it doesn’t. Like sometimes there’s an s and if you miss a letter, it doesn’t. Anyway. (Faith: Yeah.) This older dude next to me, we were just talking, I’m like, dude. Like, my flight leaves in like 20 minutes. He’s like, yeah, me too. And we were like, oh yeah, we’re headed to Phoenix. I’m like, oh fuck. Okay. So then I, I just went for a Hail Mary and I just like yelled like, ‘Hey guys, like our plane leaves in like 20 minutes. Can we just cut the entire line?’ And like, everybody was super cool. So we got through the thing through TSA, we skipped the whole line, got to the front, put our shit in, and then like, we just sprinted together to the freaking gate and we made it. And so I was like, if it was just me, I would’ve been an asshole. But because I had this other dude and I felt like I was being altruistic while also being selfish and like, lemme be an asshole, but like, in a way that was helpful.

Faith (14:03):

What a life hack!

Teja (14:05):

Totally. I was like, I’m being an asshole on behalf of somebody, which feels good. It’s like, man, I would’ve probably missed this flight. Like I was resigned. I’m gonna pay $50 flight change fee. Like, ok, I’m ready and I’ll show up there. Late, <Laugh> miss the first hike that we do, but I was, I was so jazzed. I was like damn!

Faith (14:23):

You did it.

Teja (14:24):


Faith (14:25):

One day when we’re not recording a podcast, I’ll tell you the story of when I was 19 years old, flying from Nashville back to Colgate and was so hungover, I very nearly missed my flight. It was before the days of Uber or Lyft. I stole someone else’s taxi. And ended up having a super eventful flight back to Utica, New York. So one day–just put a pin in that.

Teja (14:50):

What–what was one event?

Faith (14:57):

<Laugh>. It’s too gross. I can’t tell you. I missed the, there were no, there were no puke bags in the in the behind the seat compartment. And that was a huge issue for me. I did a lot of growing up between 19 and 30 years old. You guys

Teja (15:16):


Faith (15:17):


Teja (15:19):

How old are you, 28?

Faith (15:20):

No, I’m 30. (Teja: I’m just kidding.) Come on, let’s get into it.

Teja (15:25):

So when we first started, I was in Nashville and I was in Nashville because I had just come back from China and I needed to get shoulder surgery. So I was like, okay, let me chill at my mom’s house and get my shoulder repaired. My buddy JP, he was in Pennsylvania. 

Faith (15:43):

Phil. Yeah.

Teja (15:44):

Yeah. Like Harrisburg. Actually technically New Cumberland, which is even smaller. (Faith: Nice.) Yeah. Smaller than Harrisburg, y’all know? Yeah. If you know Colgate, you know Bucknell this is like, yeah, totally. Rich, he was in Berkeley and so yeah, so we were all remote initially. I mean this is, this is like really honest, so don’t hold this against me. We basically drew straws to figure out who would be CEO <laugh>. That was–it was just like so random. It was like, there’s no decision making process, there was no weighing of skill sets. It was kinda like, okay: this person. So I was like, okay, well now it’s my job to find money or like find customers, I guess? I’m like, that’s like what I need to do. So we just started like, you know, I Googled like Nashville startups and I found the entrepreneur center that’s like, that’s how we became kind of Nashville based.

Faith (16:44):

Mm-Hmm. <affirmative>. And I feel like between that time and when I joined, like most of what was happening was happening in Nashville, but we had folks kind of like sprinkled in here and there who were distributed, but like the culture is very much like we’re in the office and that’s how we do a lot of our collaboration (Teja: Mm-hmm. <Affirmative>). And I think like collaboration tools–I don’t know, even when I joined four years ago, I don’t know that we would’ve had the kind of like practices and infrastructure to continue moving fast remote.

Teja (17:19):

I think it just made sense in the early days to work together. You know, a and I think like when there’s not a lot of like market validation, like the social validation of like seeing your peers and like, just like grinding, like you felt like it was more real than, it’s like working for a computer. (Faith: Mm-Hmm. <Affirmative>) and that’s like two people, you know what I mean? And so yeah, we definitely took every opportunity to like, you know, JP would come in and like, stay with me at my mom’s house or like we’d fly to the Bay Area and stay in an apartment that Jumpstart had to go see Rich. Or we’d, you know, we’d meet up here and there in DC. That was pretty valuable. And then obviously when it was Tyler, Lynch, and I, and you, it was cool to come into the office, and Tracy and like (Faith: Mm-hmm. <Affirmative>). That was cool. Same thing. I felt like it was validating.

Faith (18:09):

It’s making me think of like, one of the things that I often think that I miss, which is like the osmosis of being in the same place, right? Like, there’s things that I would learn and pick up on and kind of flag as like, wait a minute. Like, that’s an interesting problem. Maybe we should solve that. Not because anybody said it directed at me, but because we were like all working in the same place and it just kind of like surfaced. At the time, just like at the phase we were at, that was really valuable. And even like before we officially went remote at the start of the pandemic, we were getting to the size where that was really no longer helpful because we were big enough that we really needed people to be siloed. And it was like, ‘No Faith. Please don’t jump into the sales process right now. Like, we actually like, need you to be doing marketing. You know? 

Teja (19:00):

Oh, I’d get too stimulated at work. (Faith: Mm-Hmm. <Affirmative>), like I’ll legit get too stimulated. Cause I, I like, I like the vibe and I like talking and being around people and I would just like leave the office at like 5:30 or 6:00 and just be like, I, I like had so much caffeine and I had so much social stimulation. (Faith: Right.) I can’t function. I like, I’m not– 

Faith (19:23):

I didn’t, I like never got things done. You know, like I talked about like a lot of different ways to do the things that needed to be done, but I never felt like I was leaving being like, ‘Cool, I can check that off my list.’

Teja (19:35):

No. Yeah. It totally, it wasn’t consistent, like a productive burn. Like I could maybe do that if I was like really disciplined. Like, ‘Okay, I’m gonna go to the room and I’m gonna sit in there and I’m gonna knock these things off the list and I’m gonna be rude to anybody who needs to have a conversation with me. (Faith: Mm-Hmm. <Affirmative>) and just focus on this. But then I’m like, then why am I here? Like, what am I doing here? You know? Right. I think part of that is the space and part of that is like, we like each other and like we kind of just like got people that meshed well (Faith: Mm-hmm. <Affirmative>) as a company. But I think people generally wanna look like they’re productive.

Faith (20:13):

Oh yeah. And not even–there’s something about looking productive that like, calms my anxiety <laugh> that it, it’s not like, oh I look productive so no one else, no one’s gonna think that I’m not productive. But it’s like, I don’t know, I almost trick myself into like going through the motions of productivity is like a good day.

Teja (20:35):

There’s another sense too, or I should say there’s another consideration where I felt like, let’s say we weren’t doing well, you know, or we were struggling with like a course of action in terms of execution. I felt like it was my job to like make sure all the potential reasons why were like checked. And it’s like a very natural inclination to be like, well okay, if we’re not performing well, like you don’t wanna have a company fail because you didn’t have people in the office just as an example. Right? (Faith: Right). Like, what are people doing? Are we being maximally productive? Are the communication lines open? And so if the company fails, you’re like, well this is like an obvious and glaring thing that I didn’t do. (Faith: Mm-Hmm. <Affirmative>.) And so part of it I think also in the early days came from like, just like my personal need to like fit our company into like the established norms of how a company functioned. Because if I didn’t it, it would feel like, like an obvious error on my part. (Faith: Right). If that makes sense. Right.

Faith (21:45):

It totally does. And I think it’s like a function of the time too. Like there were several companies that one of their–it’s basically like a value proposition for what they did. They were like, look, we’re a fully remote company and that’s why that’s actually good for our customers. But everybody else is like, you know, it would’ve been weird to have that be part of what you do.

Teja (22:11):

Totally. And I mean, you know, a lot of it was like, I mean, I have to say like it was, it was me taking understanding from people who scaled their businesses and like have, you know, exited or gone public and like now they’re chilling and they’re like, okay, like in our day it was really important to have people in the office. And I’m like, okay, yeah I guess that’s still true. But then the pandemic happened and then I think everybody was like, yeah, nobody wants to get COVID. (Faith: Mm-Hmm <affirmative>.) So not, I mean I remember when the day, the day the first Williamson County case happened, like okay shit, it just got real <laugh>.

Faith (22:51):

Yeah, I know. I feel like that’s seared into my memory cuz we also had just had a tornado in Nashville. (Teja: Yeah.) So it was like, it was just like a week of also–Teja, in January of 2020, you were like, ‘Guys, I think COVID is gonna be a thing’. And you had like this whole contingency plant, you were like, this is like, you know what might happen and blah blah blah. And then COVID was a thing, but it was like after the tornado, so everything was so–it was just a crazy couple weeks. I remember that. I think I’ll remember that forever. <Laugh>

Abbey (23:37):

Do you think that you guys would’ve eventually gone remote or like what do you think the timeline would’ve been to going remote if the pandemic hadn’t happened? Or would you have?

Teja (23:46):

Hmm. I don’t know. Honestly.

Abbey (23:52):

I think one of the things also with like, with a new, new business is like, it gives you, you know, where like you were saying that people will think that it’s like a, it’s a value prop that you work remote. I think it’s also like a, there’s a part of like a new company starting where it’s like a legitimacy thing where it’s like we have an office, we’re based here. This is where everything happens for like a newer company.

Faith (24:15):

I think we had flagged it as a liability and at least like the year leading up to the pandemic because one of the key when we did like sales practice, like how do you, how do you deal with you know, questions on the phone with a, with a prospect? One of them was, I don’t wanna hire remote. Right? So we would practice sales scripts of like, here’s why hiring remote developers is a benefit for you and you know, we can help you manage and blah blah blah. And so for like a year we were having lots of internal conversations like, is it a liability for us to not be a remote team and also have this be the core value that we’re trying to sell to folks?

Teja (24:58):

Totally. I also remember being like, okay, if we need to hire executives at some point and we need to hire them outside of Nashville, I don’t wanna make somebody’s family move here and then I have to let them go later cuz I’m gonna feel like an asshole. Like that was actually, I was like, how am I gonna like navigate that? Like, cuz this city is not, was not mature enough a couple years ago to have like a lot of sophisticated later stage executives (Faith: Mm-hmm. <Affirmative>) in the tech industry, I would say Healthcare? Sure. Every person’s in the revenue cycle management, but like, you know, not like tech shit, you know? And so I was like, how the were we gonna do this? So we were like, we had some remote people and stuff, but I think when we had the remote people who were in the office, there was always a disconnect. Right? Like, I, at least I felt that way. I’m like, this person’s over here on an island. (FaithL Right.) And we’re in the office. Right? And then I, so yeah, it was, it was interesting.

Abbey (26:06):

I do like working remote, but every time I hear that like people are like, oh, going into the office gonna see everybody. There’s this like that that little tinge of like–

Faith (26:16):

I wanna see everyone!

Abbey (26:17):

<laugh>. I miss it a little.

Teja (26:18):

I know.

Abbey (26:19):


Teja (26:20):

I hope that we would’ve been rational enough to eventually end up at remote. (Faith: Mm-Hmm. <Affirmative>) as of default.

Faith (26:27):

I think, and this came up in conversations like before we went remote, which is like if we do it, it has to be a hundred percent or 0%. (Teja: Yes.) Because the problems we ran into was like, okay, well if some people take remote days here and there and then we hire a couple remote employees, that was when we felt like we were slowing down, was because none of our norms and rituals like made sense in both contexts. Right?

Teja (26:57):

Totally. And it’s actually easier to be a remote company when you’re bigger than when you’re smaller. That’s like five people. It’s not easy to be remote cause 20% of your company may not be there. And it’s like, okay, we can’t talk about this thing without this key person. (Faith:  Mm-Hmm. <Affirmative>. But when there’s like, I dunno, 20, 25 people are working at different times, people are taking leave, people are going to lunch. It’s just a lot less friction. And so I feel like as the company is scaling, actually remote becomes like a lot easier. And then it also helps us hire without like a constraint. Yeah.

Faith (27:32):

You know? I’m curious like, and this could be in our context at Gun, but I mean Abbey’s worked at remote companies before as well. What are the things that we think make it work really well? Like whether they’re rituals or expectations or whatever.

Abbey (27:49):

It’s a super simple thing, but having like stand up every morning where everyone’s just like, here’s what I’m doing for the day. You know, like it sets the tone for the fact that like everybody’s got something to do. Everybody’s got something to contribute today and feels like a little bit less of a silo. Especially when you see things that are happening across teams where you’re like, okay, we’re both, we both need to work on that today. We’re both on the same page that that has to happen. I think things like that work really well. I know that there are a lot of people who like hate company wide happy hours. I like that ours is like, it’s no bullshit and it’s not like there’s no pressure for it.

Faith (28:26):


Abbey (28:27):


Faith (28:27):

You know, sometimes it’s like two people and sometimes it’s the whole company <laugh>.

Abbey (28:31):

Yeah. Like show up and show up and connect with the people you work with.

Teja (28:36):

I love that. I think that’s cool. I’m glad sometimes I think I’m like, is the daily standup thing is that like, I don’t know, does that introduce like cumbersomeness into people’s day? But I’m glad ‘cause I find value from it too. Mm-Hmm. <affirmative>. 

Abbey (28:49):

I mean I think we’ll eventually grow to the size we’re like doing that for the whole company in one channel is probably a little cumbersome. (Trja: Yeah.) But it’s like, yeah. We’re still small enough that it’s like having that visibility keeps people from being super siloed.

Faith (29:05):

Exactly. And I’ve like more than once, just by like reading everybody and we do this async that’s probably worth calling out. Like (Abbey: Yeah.) We don’t have a live standup with the whole team and we’ve got folks in lots of different time zones. So, you know, you can kind of read it throughout the day and but anyway, like more than once in the, in our like daily reporting channel, I’ve flagged like, oh shit, this person on a different team is actually working on the same thing as me. Like we both zeroed in on the same problem and we should probably collaborate or like this person is working on something that I think I could contribute to. And like, we just wouldn’t have those conversations otherwise cuz we’re not sitting in the same open office space. So I feel like that does a good job of like condensing what you would get by sitting across the room from another team during the day into one quick list of messages from your colleagues that you can run through, you know, while you’re refilling your coffee and get a sense of the world.

Abbey (30:03):

You know, another thing that I’ve noticed in other remote jobs that I’ve had is like having teams in different places offers you a different perspective. I mean this was, I think especially important when I was like, I, what the, the company, the first company that I was a dev for was an international money remittance company. And there are a lot of cultural differences around the world. Mm-Hmm. <affirmative>. And when you’re sending money to like hundreds of countries, you need the perspective of somebody who’s not in your office. Mm-Hmm. <affirmative> somebody who’s not like the 20 person dev team in Denver has no idea what’s culturally appropriate for the team in Bangalore. (Faith: Right.)

Teja (30:42):

When you pay a bribe in India, you don’t hand them the money.

Faith (30:45):

<Laugh>. That’s gonna be my thing I learned. I feel like we started doing this before we went remote and it kind of like just trickled through into our remote rituals. But every Friday when we do our daily reporting, people share something we learn that week and something they’re grateful for. And especially with new teammates on remote teams, people who don’t work directly with them every day don’t have an opportunity to learn like what are their kids’ names? You know, what do they do outside of work? What–just these things that, and again in the office you would absorb through osmosis. It’s really difficult to do that in a way that doesn’t feel like weird <laugh> on a remote team.

Abbey (31:29):


Faith (31:29):

Yeah. And this like, yeah because it happens every week and it’s a ritual. Like sometimes you can tell people like phone it in and sometimes it’s actually, you know, something that they really wanna share. And that’s okay because it happens every week. And I don’t know, I think that that’s like a really cool thing that we might have accidentally stumbled upon, but I think other people should do.

Abbey (31:52):

It’s cool also that like, you then learn the personalities of people by finding out what they think is interesting. (Faith: Yeah.)

Teja (31:57):

<Laugh>. Yeah.

Faith (31:58):

It’s, yes. Absolutely.

Teja (32:00):

I think going remote has taught me a lot of acceptance in a way where like my disposition is like when I have like anxiety or uncertainty about something, I wanna like really tightly manage the process. I wanna be like, okay, the, you know, we want to hit this growth rate, we’re not hitting this growth rate. I need to tightly manage every activity and make sure every unit of time across the entire company is efficiently allocated so that we can accomplish this goal. Like that’s like my default posture in like everything. Right? And so like when you’re remote, it’s actually impossible to do. And then like, it’s actually worse I think cuz there’s no way to be like: let me see your work on a Zoom screen for eight hours. Like then you can’t work. Right. And so, I don’t know,

Teja (32:56):

I think for me in particular, it’s like not being conflicted about that and it’s like accepting like, hey, okay, like we’re remote. That’s it. And like we will have to trust that people will allocate their time effectively to the extent that they can. (Faith: Right.) And that at least that lack of conflict for me has given me like way stronger conviction and like maintaining a remote company. And it’s, it’s good because I think like from a cultural standpoint, like you generally want at least my understanding is that people want to be left alone to allocate their time effectively.

Abbey (33:33):

And you know, like you should, are you comfortable with the people that you hired that they, you know, like you hired people who allocate their time appropriately?

Teja (33:42):

Not always. (Abbey: Yeah.) But that’s a personal problem.

Abbey (33:44):

And when you–<laugh>

Faith (33:47):


Abbey (33:48):

Fair. But it’s like something I think that when you, when you move to remote, you kind of have to like, it’s something you probably have to work on.

Teja (33:55):

I think the, the tough, I mean this is like super meta, but I think the toughest thing about management, even remote or not remote is figuring out how much of this thing that you don’t like is your problem versus somebody else’s problem. You know what I mean? (Abbey: Yep.) Like how much of this is internal conflict and something that you can control and better manage to, and how much of this is somebody else’s problem? And I think remote shifts the context a little bit for you to be forced on the more important things. Cuz you’re not really focused on shit like, are they showing up at 9:05 or 8:05 or leaving at 4:19 (Abbey: Mm-hmm. <Affirmative>), right? Like, you don’t really worry about that. You just can’t, it’s like impossible to worry about that. So you focus on like other things. And I think healthier things when you’re trying to manage a team.

Abbey (34:40):

Things like, did we meet the goals that we set for the team: (Teja: Hundred.)

Faith (34:45):

Which Yeah. Things that are measureable.

Abbey (34:46):

You know? (Teja: Yeah.) If you could meet those goals and someone was working at 6:00 AM and someone was working at 9:00 PM and the goals are still met.

Teja (34:53):

But then there’s this, there’s this meta level of are the goals people are setting, are they aggressive enough or are they pricing in a more comfortable and slower paced work? Like,

Faith (35:07):

Well also, like our goals are, so I I, it takes a while.

Abbey (35:12):

Well I’ll tell you, I overshot way hard <laugh> this quarter anyway. I was like, you shouldn’t have done that <laugh>. It was too many things. Yeah. It’s, that’s, and that’s kind of like where it comes back to like, are you hiring the people who you think are gonna allocate that time appropriately and set the right goals and you know, like, are they gonna be a contributor to the business in a way that meets your end goal regardless of where they’re working from?

Faith (35:36):

In the office, I felt like if someone on my team was working on something and struggling with it, I could see that they were struggling and I could watch the attempts, like the at-bats that they were having and like really easily jump in like when it was an appropriate time. (Teja: Mm.) But I feel like one of the challenges I have with remote has been like, how do I, how do I know when people are struggling? Especially if they’re not, you know, apt to like raise their hand and be like, this is actually the things that I’m trying aren’t working here. So we’ve started doing just like a H2O reflection at the beginning of our marketing meetings. (Teja: Mm-Hmm. <Affirmative>.) So like things that, like opportunities and you know, obstacles, things that are like giving us trouble. We service ’em then.

Faith (36:28):

But I don’t know, I think that’s still a learning area for me as a manager is just figuring out like, like how do you identify that and keep your team from like, turning on something that isn’t working. And I think the other problem is like, our metrics are so–they’re like any one metric is moved by maybe like dozens of initiatives. And so measuring based on metrics is sometimes a lagging indicator of what’s happening. So again, like trying to balance like how, what’s the right amount of like insight into the work that’s happening compared to just, you know, the stance of like, do whatever you gotta do to hit these metrics.

Teja (37:13):

I mean the way that I think about it is like, at least the way that I’ve like reconciled it is like when it comes to management, which is different than leadership, I think. I think when it comes to management, my ultimate loyalty professionally is to like the metrics of the business. Like I have to just make the right decisions to keep the metrics solid and up and to the right. And like, you know, it’s like we need to go remote during the time that we did. So like, okay, now we have to manage the metrics and that context. But then there was enough evidence to suggest like, hey, okay actually on these other measures of like quality of life and work happiness and this communication ease, it seemed like not only could we hit the metrics that we wanted to hit remote, like also made other metrics better.

Teja (38:08):

Right? And so it was like obvious I think to all of us in the company, let’s just stay remote. Maybe that’ll change at some point. I don’t know. But I think from a management standpoint, like I think it was like really clear. And then from a leadership standpoint, which I think is different, it’s like good leadership is like not about me, it’s about to what extent I’m able to meet the needs of like the team and like to what extent I’m able to balance. Like I think people need safety in work, obviously, but also there needs to be some level of uncertainty, challenge and like change. Hmm. Right. And actually people exist on different spectrums. I mean, they exist on different points on that spectrum. Like some people want a lot of safety, some people want a lot of uncertainty. Right? And a lot of growth and a lot of change.

Teja (39:02):

And so like how do you kind of balance that organization from a cultural standpoint and how do you kind of give people that, and I, and I feel like remote has helped the business metrics and then from a leadership standpoint, it’s like people are actually able to trade off on the growth versus comfort spectrum more autonomously than in an office. (Faith: Hmm. That’s interesting.) Yeah. Like you establish your own work patterns. Right? And like then it’s our job as leaders to figure out like if where they naturally fall is in accordance with the culture of the company. (Faith: Mm-Hmm. <affirmative>), I dunno it’s been, it’s been good. I would say, well we aren’t getting an office, we’re gonna buy a building and put a gym in it and put some jiu jitsu mats in it.

Faith (39:50):

Is that an office or is that like, an offsite for Teja? <Laugh>.

Teja (39:56):

Why not both?

Faith (39:57):

Why not both?¿Por qué no los dos? <laugh>

Teja (40:01):

Yeah, it’s happening. I mean maybe next year, maybe the year afterwards, but yeah, we’re gonna get a spot and my hope is that it’s got a little bit more private meeting rooms (Faith: Mm-hmm. <Affirmative>) and like it’s in a sick part of town and people can come in and work. People can do whatever they want there. (Faith: Yeah.) Hopefully mostly working.

Faith (40:23):

Well I was gonna flag that as like kind of the next, like if, if this is a state of the world today and we’ve got a couple challenges, but we also have a few things that we’ve done as a ritual that have helped us perform really well remote. I think like the next horizon for us is figuring out how to meaningfully get the team together physically on some sort of regular cadence, whether that’s like annually or twice a year. Because I don’t know, I feel like the teams that are often highlighted and like ‘people who do remote the best’ have some sort of like, get together on a regular basis.

Teja (41:03):

No, we should do it. I mean there was like a virus that was killing a lot of people. So I’m doing it now.

Faith (41:09):

<laugh> I know. Yeah. This is like the first year where comfortably be like, yeah, we should buy flights for people. <Laugh>. Yeah.

Teja (41:15):

Yeah, and I don’t get me wrong, I was over covid pretty quickly to be very politically neutral, but like, also like you have to respect the inclinations of other people. (Faith: Mm-Hmm. <affirmative>.) And it’s like, you know, you don’t wanna have an offsite and then half the team is uncomfortable traveling. It’s like (Faith: ) Right. This doesn’t make sense, you know? Yeah.

Faith (41:35):

So Yeah. Well hopefully we’ll be able to do that soon and maybe get the–(Teja: Next year.) Yeah. Get the team in the whatever this new office space is.

Teja (41:44):

Yeah. I mean, aren’t you in charge of planning the offsite? Like… 

Faith (41:47):

Yeah, exactly.

Teja (41:49):

So I, I vote two options. One of two and we can do both. Or one, one is like pretty easy. We should do like some sort of like thing in Tennessee. Like they’re like, like there’s like Blackberry Farms, obviously there are other ones like that, that are like retreats, you know, that are like, actually they have conference rooms and meeting rooms and like all this shit. Maybe you were telling me about one of these places. 

Faith (42:14):

Probably not.

Teja (42:15):

Okay. Yeah. There’s one that’s like run by like  a like a husband and wife, entrepreneur duo that had some business, but they like now manage this retreat for businesses. So (Faith: Cool.) Yeah. And then the second is like a music festival, like an electronic music festival.

Faith (42:34):

Veto, immediately <laugh>.

Teja (42:38):


Faith (42:38):

Immediately no.

Teja (42:40):

Like I would love to go to Vegas.

Abbey (42:41):

I wanna check out there’s a the Grotto?

Teja (42:44):

That is in the Playboy?

Abbey (42:46):

No, no, not that one. It’s like an underground music venue in eastern Tennessee somewhere.

Teja (42:53):


Faith (42:54):

Is that the caverns? You said underground?

Abbey (42:57):

I’ll look into it. I’ll send Teja some information.

Teja (43:02):


Faith (43:02):

Please do. I just made an Asana task, so I will plan the offsite soon.

Teja (43:12):

Oh, that’ll be sick. We’ll have people flying in from all over the world. I know, I, that’d be a legit, I mean I don’t envy…

Faith (43:19):


Teja (43:20):

<Laugh>. Yeah. Or, or or Deividi I mean…

Faith (43:24):

Right. Yeah. At least it’s like kind of the same-ish time zone. I feel like the hard part is trying to get from like Asia to anywhere in the US. I feel like one of the other benefits is by nature remote requires that everything is documented because you’re, you’re communicating async by default. Yeah. So this issue that we used to have when we were all in the office of like information silos and Right. Like things that were just like absorbed that nobody wrote down. And when we brought in new teammates it was a nightmare to try to onboard them. That has gotten exponentially better since we were went remote because everything’s already written, you know?

Teja (44:10):

That’s so true. And, and I think it makes you a better manager and I think it makes you more autonomous as well. Like, and I think those two things are like, I dunno ultimately how you probably find meaning in work.

Faith (44:26):


Teja (44:26):

<Affirmative> and it seems to be better for like life. Like, cuz you can integrate it better. Which I mean, I’m speaking strictly about the business benefits. Obviously I care about people outside of work, but it’s like even looking at just the P&L, I think there’s like real benefit to being remote cuz people are not having to be like fuck, I have to schedule this dental appointment on this day, but I gotta be at work here. And I just came back on this day, so blah, blah, blah. (Faith: Mm-Hmm. <affirmative>), it’s like a lot smoother.

Faith (44:55):

Just the time that you went back

Teja (44:57):


Faith (44:58):

Is incredible.

Teja (44:59):

Do you guys think that there is pressure, good or bad to look visible and active in Slack?

Faith (45:09):

All work happens not on Slack. Yeah. I don’t know. I feel like I’m in a bunch of Slack communities with like, you know, developers and marketers and I look at people who are constantly in those slacks and like, it’s not their company Slack, but they’re just like talking about things all day with people. And I’m kind of like, do you not have other things you wanna do or is this just your job is you get to like learn and discuss? Sometimes I feel immediate response in Slack to something that hasn’t been directed at you is almost a signal of like, you don’t have enough to do.

Teja (45:50):

Oh, that’s interesting. I bet you curved a lot of dudes who were overly responsive to you.

Faith (45:56):

<Laugh> I dunno about that.

Teja (46:01):


Faith (46:02):


Teja (46:04):

Hey, this nothing else going on. He’s texting me immediately. Fuck this guy. <Laugh>.

Faith (46:08):

Oh yeah. Oh, like breaking in?. Yes, a hundred percent.

Teja (46:13):


Faith (46:13):


Teja (46:15):


Faith (46:16):

Yes. I don’t, I’m like such a regimented person. Like even emails, I’m like, I check my email at 8:00 AM and at 6:00 PM and if you email me any other time during the day, like I’m not gonna, it just like interrupts your flow. And I feel the same way about text.

Teja (46:32):

It’s a good signal though. You’re right. If somebody’s like really responsive on Slack, you’re like, like what are you doing? I’m just, why are you talking to me? But then I’m like, why am I talking?

Faith (46:42):

Or just like happened to be on, I don’t know. I don’t wanna, I think the point is that judging, using Slack is like any sort of indicator of productivity is innately flawed because some people’s jobs are talking on Slack all day and some people’s jobs require that you actually are not on Slack.

Teja (47:02):

That’s so true.

Faith (47:03):

Like to be a, to be a really great writer and content producer, Abbey needs to be in a state of focus like 90% of the time. I don’t know, I feel like it, it depends on the job time, but it is like such a, it’s interesting that there’s pressure there to look like, to make sure that people see you on Slack. I think that was maybe like an early thing for me when we first went remote.

Teja (47:26):

Me too. I mean, I would all, I, I would, I would feel like it was like my obligation to a, to make that pressure known. Cause I’m like, oh, like where I work, it’s my job. I need to act like, you know, you need to be on Slack all the time. Cause it just felt like a variable that I needed to control (Faith: Mm-hmm. <Affirmative>) to get performance. You know, then you kind of mature and you’re like, eh, it doesn’t really fucking matter because like you said, how responsive somebody is on Slack doesn’t affect their work quality. So…

Faith (47:58):

And it might like negatively affect their work quality depending on the kind of work they’re supposed to be doing. (Faith: Yeah.) I think that performance, like poor performance is so incredibly obvious in the actual work product that we don’t need Slack to be like the indicator, you know? (Teja: Yeah. Yeah.) But that was, that was a lesson I think we had to learn because like you said, when you’re in the office, the ability to like see somebody tippy tapping away on their keyboard is such a mental, just like anxiety reducer, you know?

Teja (48:32):


Faith (48:33):

So we were trying to like recreate that via Slack. What feels like the easiest way to isolate, is it the thing or the person or is it me? Is what’s like visible to you. And in our case, if we’re talking about employee performance, the thing that’s visible is the little green dot next to your name on Slack <laugh>. Totally. Or how fast you respond to my message.

Teja (48:56):

Totally. And I mean, to your point, it’s like you actually get a more objective view at reality and of performance with like, like space, like physical distance and like, okay, I am not seeing this person, so what’s the work product output? And then yeah. The next level is like not caring about if their light is green or not. (Faith: Yeah.) Not green.

Faith (49:23):

I feel like the obvious question here for people listening who are like worried about the perception of their performance is like, oh shit, if it’s not responsiveness on Slack, and like, sure metrics make sense, but how do I make sure that those are getting surfaced at the right time to the right people? Like how should people be communicating their work and their performance in a way that’s valuable and also easy to consume from a leader’s perspective?

Teja (49:55):

Hmm. I think one level is proactive communication. (Faith: Mm-Hmm. <affirmative>.) So you know, whether that cadence is like daily or twice a day or once every two, three days. I think like there’s a lot of different tactics, but I think the philosophy is like, it’s better to communicate proactively about a roadblock or about progress or about stalled progress earlier on than it is to like, wait until there’s a problem and that there’s no progress

Faith (50:33):

Or wait until somebody asks about it.

Teja (50:35):

Hundred hundred percent. Okay, how’s this going then? Which is like fine. Usually like that, Hey, how’s this going? You need help. Like, that’s fine. But it’s like when it’s like, where are we? Or like, what’s going on with this? In that certain tone, then it’s like a little bit different. And that’s actually something like I’ve, I’ve noticed like that, that’s been really helpful, especially because, you know, we’re now three months, four months into like having a board and like having, and like, you know, from a governance standpoint, like the CEO works for the board (Faith: Mm-hmm. <Affirmative>), I’m on the board, but like, it’s like I have to put on like my, I am an executive and I’m hired by the board to execute the strategy that we come up with. And so like I take that kind of seriously. So trying to honor that relationship, it’s like proactively communicate even in between board meetings if there’s a problem, make sure that that’s addressed and like the light, you know, text message sometimes even (Faith: Mm-hmm. <Affirmative>)

Teja (51:30):

Hey, we’re struggling here, but I’m on it. Boom. Like done. And so proactive communication and then I think like the right cadence for the proactive communication. I think generally if you’re like, let’s even say like you fall on the median point of like the EQ spectrum (Faith: Mm-hmm. <Affirmative>) your instinct on how often somebody wants to be communicated with is probably right. So it’s like, you know, if you hit ’em every week and they’re texting you or slacking you every other day (Faith Mm-hmm. <Affirmative>) like, I think that’s probably not fast enough. Like, I need to maybe go every day until there’s enough trust built where they can, it’s kind of let go a little bit. So yeah. So I think that those are the two, two things is like proactive communication, that you can find out what proactive means for the person you’re working with. If you know, just based on reading the signals/

Faith (52:22):

Also pull out of that answer like flagging problems because I feel like nothing builds trust more with a leader than when somebody else calls out a problem before I have to see it. You know, because if I’m the one who discovers like, guys like, this thing is not working the way that we thought it was, and they’re like, oh yeah, well, you know, we’re, we’ve been addressing it, blah, blah, blah. It’s like, no, I, I shouldn’t have had to have called that out. So I think, I think it’s a, like a, a frequent mistake because it feels kind of antithetical to what reporting up should feel like. Right? Like we think of reporting up as like, look at all these great things that I’ve done when in fact the thing that makes leaders feel most like in the loop and comfortable with your work and performance is when you tell them about that actually is not working the way you thought it would.

Teja (53:15):

Totally. Yeah. Totally. And that’s interesting too because it’s like I’ve had, I’ve had to balance like maybe not being so problem oriented and being a little bit more success oriented because there’s a balance, right? Like, you don’t always want to talk about problems, you wanna talk about progress because it’s exciting and like, you know but yeah, I think, I think you’re right in terms of leading early and often with problems is like, it is the way to build trust.(Faith:  Mm-Hmm. <affirmative>), it does feel very good to know that everybody in the company like sees these specific problems. At least ones that I, people that I work with directly. (Faith: Mm-Hmm. <affirmative>), it’s nice, it’s very comforting when somebody’s like, I’m keyed in on this problem and it sucks, but I’m on it. It’s like amazing.

Faith (54:02):

So one of the founders of Maven, which is like an online learning platform, has just like really good consistent thinking around this concept of managing up. One of the concepts is like, your manager shouldn’t have to do the analytical work to piece together the story of (Teja: Mm-hmm. <Affirmative>) what you’re doing (Teja: Mm-hmm. <Affirmative>) and the themes from your work, right? Like (Teja: Mm-hmm. <Affirmative>), you need to make it so incredibly easy for your manager when your manager’s manager asks them what you are doing, they should be able to quickly be like, okay, these are the three things that are most important to them. Here’s a problem that they’re working through right now. And they can’t do that. Like they’re managing too many people to be able to do all that analytical work on their own. Like, you need to feed them something very easy to consume.

Teja (54:50):

Yeah, totally. That heavy lifting has to be done.

Faith (54:54):

Right. And it’s hard because when you’re doing the work, it’s like, well, I’m doing so many things and I’m, you know, I’m starting at 6:00 AM and I’m finishing at 8:00 and I’m so busy, like, can’t you see that? It’s like, no, I can’t because, you know, we’re remote. So. (Teja: Totally.) It’s a really heavy lift for you as like someone who’s being managed to pull together to like actually distill your work into those key takeaways. But I think that that’s like more than being online on Slack, I think that’s a really powerful indicator of your quality of work.

Teja (55:25):

Yeah, I love that. That’s so true. And also like you don’t want your manager to see like all the inputs. You want to be focused on outputs, I

Faith (55:33):

Think. Mm-Hmm. <Affirmative>, Teja, I feel like we covered it.

Teja (55:37):

Let’s, let’s adjourn.

Faith (55:38):

Let’s adjourn. <Laugh>. Thanks for listening to the Frontier Podcast, powered by We dropped two episodes per week. So if you like this episode, be sure to subscribe on your platform of choice and come hang out with us again next week and bring all your internet friends. If you have questions or recommendations, just shoot us a Twitter DM at the Frontier Pod and we’ll see you next week.