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[upbeat music] Hey friend, it's David Nebinsky, the community lead here at the Chief of Staff Network.

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We help chiefs of staff through the three Cs: cohorts, curriculum and community via Slack with over nine hundred people in it. Learn more about our membership and upcoming events and programs at chiefofstaff.network.

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There you can learn about our fundamentals course and our AI fellowship and so much more, including our three Chief of Staff Connect conferences, with the first one being in San Francisco on May fifteenth to May sixteenth.

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Hope to see you there. Okay, so are you also interested in learning more about how a chief of staff and a principal work together? Well, this episode is for you.

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This episode is with Taxwire Chief of Staff David Moon and Taxwire co-founder and CEO Andrew Rea.

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In this episode, you'll learn about how David got his chief of staff role, how this chief of staff role may be different than others, their communication style of constant communication, and so much more.

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Excited for you to level up as a chief of staff. Here we go with David and Andrew. So, um, we'd like to just dive right in on how chiefs of staff, um, get their chief of staff roles.

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So, uh, as we kind of-- let's just start there.

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Like, David, how would you say, like, you got your chief of staff role at Taxwire and, and I guess An-Andrew, obviously you could share your side of the story too, but maybe like David, from, from your perspective, like how, how, you know, was there a posting and like, did you apply?

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Like how would you kind of like frame that up? Uh, no.

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So I guess it all kind of started because I was actually looking at like startups that could get really big in America, like coming out of Asia, and one of them were like sales tax and VAT compliance.

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So when Lovable was kind of blowing up, I made like a landing page and, um, tried to kind of whip up a little bit of a product demo for whether like this would stick in Asia to kind of get feedback from Andrew and like that's kind of, I think, where at least the initial conversation started.

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Does that sound about right? Yeah. I would say we, I mean, we knew each other. That's probably useful context, I would say, is that we've known each other for like five years, some- Five years. -something like that.

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Um, and so we, we met through mutual friends back, back in the day before, like probably two jobs ago for you. Um, and then I think we've just kind of been friends over the years since then.

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You spent a good bit of time as an investor, and obviously I, I knew you, knew you through that. You knew me since like starting Taxwire. And so you knew I was working on this.

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You knew a decent bit more than maybe most people do about, about the business that we're in. Um, and so you-- and so then, yeah, you would like-- we obviously like-- it's not like we never talk.

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Like we, we do talk on something of a consistent basis. Um, and then you had just texted me one day, like this, this idea that you, you prototyped up in, in Lovable, and I thought it was interesting.

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And I mean, that we had actually like, I think, taken on a couple customers that had that use case already, and it was, it was in the back of my mind as like, this is a vertical we could go deeper on at some point.

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So I think you texted me that, and I put it in our Slack and was like, "Oh, this is interesting." And I, I actually shared the, the link.

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Um, and I don't know, one of our engineers was like, was, uh, like just impr-impressed that you opened up pretty quickly. And then I think we talked later that day just about like the idea and what it would look like.

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And then I think at some point I just asked you, "Yeah, so like are you trying to like start this yourself or, or like, do you wanna come do this here? Like, would you come do this here?"

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Um, and you were like, "Potentially." And so then that kind of started it, and I think we, we kicked around the idea for like a week or two, and then I think actually no, maybe not even that long, like maybe like a week.

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And then I think you just, you kinda came on as a contractor to start, just to like for us both to like test and see if like this, this was gonna be fun. And, um, pretty quickly we realized we, we had to work together.

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At least I, I felt like, okay, this is, this is gonna, gonna work out well. So, but there was no jo-job description. There was no-- I never like had like, oh, I'm hiring a chief of staff.

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I, I had like a back of the mind thing of like, I need help. Um, and then I trusted David, and I think da-- very highly of David. David's very smart. David works really hard.

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Um, and he kind of pitched me on, on like, on the idea, and we just organically, I think we both started thinking about like what it would look like to work together. And then the role kind of came out of that.

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There wasn't originally like a search going on necessarily or a role.

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It was like you kind of find a great person, and you get the chance to work with them, and then you, you, and you have, have a need, and you figure out the role from there. And, and Andrew, you said, "I needed help."

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Like what, what kind of like... What, what, what, what did that look like? How many, how many, uh, employees did you have? You-- it sounded like you said you had like a couple initial customers.

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Like what was kind of like- Yeah. Yeah. Yeah. Our, our history in the business today, we've been around about a year and a half.

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We've raised like close, close to four million bucks, um, in like most like pre-seed seed, I guess. Um, and we spent most of last of like kind of...

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So we raised that first round in December of twenty twenty-three, spent basically a year building. We, we like did like a soft launch to like our first customers in like late November, early December of last year.

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Um, and so the business is like relatively young and like most of last year it was like four or five of us that built like the entire foundation of the co-company.

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Um, so like all like engineering and, and tax and, and, and for the record, like we, we do global sales tax compliance.

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So all the stuff that goes into understanding, access, doing registrations, doing calculations, and doing like end filing and remittance to countries in different US states.

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It's a pretty complicated problem, especially if you're a business that sells, sells stuff everywhere and has just like a, a very across the United States or a very global, global footprint.

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Um, and so we've actually, actually talked to some of the folks that I think you, you work with David, David about this. Um, so, um, I think, um, so anyway, um, I was, I was tying that together in-into a loop.

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So that, that was the business. There was like five of us. Um, we'd had some pretty like good early traction late last year, and so we, we, we ultimately were like, "Okay, we need to... It's, it's working.

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We're like growing, growing pretty fast. Um, we need more engineers." And so we, we've-- so the team had grown pretty quickly. We, we're now about like ten of us now.

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Um, but it's still, except for me and-- David and I do everything that's not engineering or tax related. Um, and tax for us functions-...

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closer to engineering than, than, than like, I guess like being a CPA, um, for, for reference. And so yeah, I was just doing everything.

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I was doing like onboarding, implementation, sales, marketing, trying to wear like at least part of the product hat.

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And, um, it just was like, there's like not enough time, and we're growing fast, and, and we need to keep growing faster.

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And so, um, I think that was where I was at when David like messaged me is I felt like I was already like, there's too much going on. Um, and so I think the, the need was there.

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I wasn't exactly sure what I was hoping to hire for necessarily, but I think I, I knew I trusted David, and I think the, the path of that turning into like a chief of staff role developed from there.

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A-and then David, like after Andrew's kind of like reaction to the, to the link and all like, and obviously it sounded like you were excited about the product and the industry and stuff.

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Like what was it like on your side when you were like, okay, like, you know, I know, I know Andrew for a while, this, I like this company. Like

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now it seems like there's an opportunity to work together here on a more like official full-time basis.

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Like how are you kind of thinking about that in terms of like, okay, like this sounds exciting because like I'll get to work on this or like what, what was it like on your side after that like initial kind of like reaction of like, okay, wait, like s-see there's, there's, [chuckles] you know, there's, uh, An-Andrew seems excited about this.

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Like what did you... how were you thinking about kind of carving out your chief of staff role and, and your overall kind of role in the beginning? Yeah. So I think two things were really important to me. Number one,

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I, I came from mostly an investing background, um, early stage. Um, th-that itself, um, it was pretty grindy 'cause I came from Korea. I didn't have family in America.

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Like, you know, to break into that entire industry, you have to kind of work really hard to like kind of hack a way, hack a, hack your way into it in some way or another.

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And, um, from an operating side, I previously worked for like a founder that went from C to Series D at YC in four years. Um, you know, his second startup, everything from like the zero stage. But

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for, for Andrew's case, you know, for, for Taxfire is different because, um, w-we weren't at the zero stage when I joined. Uh, we, we had quite a bit of traction. And

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what I really knew that was important at the time were like i-it's still at a company's stage where you, you cannot be managed. Uh, you have to be an individual contributor.

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So what have I done and what can I bring to the table that is suited as an individual contributor, so I'm not acting as a dead weight to the company because the company cannot afford that?

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Uh, I think that was kind of the first question that jumped in my mind as I was, you know, thinking and looking about this, 'cause I've wanted to invest in Taxfire for a long time, um, ever since it was a company actually.

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It, it, before it was a company I wanted to invest in. But, you know, the, the VCs that I, you know, generally work for are more conservative, so, you know, um, couldn't.

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But, you know, the opportunity that I did come as an operator, of course I wanted to jump in. But I think, I think those are like the realistic, uh, questions that I had to answer to the back of my mind.

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And I think it was the question that I also wanted to make sure that, um, Andrew could also justify bringing kind of the non, uh, technical hire to, to the group. So,

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um- And I don't know if it's just the resume for you, David, but I also think having very briefly earlier in my career been like a junior investor, um, I think it's hard coming from that role into startups just because it's, it's like, uh, you, you have maybe like you've done some things that are relevant, but it's not like as clean cut.

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Like if you did growth somewhere and you're like talking to a startup, "Oh, I can join this like growth role," it's like very straightforward, like one-to-one jump.

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Whereas I think couple things we tried early stage, one, there's just like, there's more blurriness between roles anyway.

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And then two, you're not like bringing at least like something of a like, "Oh, I can easily grok like what I did here and, and translate that to this."

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And so I, I don't know how much you, you've felt that, but I think that's like always like one of the tricky things about potentially joining an early stage startup when you've spent most of your career as an investor.

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I, I think, I think that's right. Um, the closest role that I had in like hacking away something from when there was nothing into something as an investor was my first job out of college.

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I worked at like a sub $10 million pre-seed fund. Uh, it was basically like a family office that was operating as a VC. So this is when I actually met Andrew.

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I was sleeping through my friend's living room couch, sofas, meeting LPs in New York, anyone take a meeting so I could fundraise.

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I, I created that entire outbound process and I closed a little over $3 million, um, you know, six months out of college.

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So like that I knew how to do, but like on, on a startup side, you know, when, when, when the go-to-market function needed to like go jump, you know, when, when things needed to pump out even more numbers, um, I, I just wanted to make sure that I had enough conviction in myself that I can deliver to the standard that the organization needed.

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And, and from that moment, I think it was just kind of, um, like this is something I want to do. Do I know if I can grow into it is a question mark.

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Uh, maybe I can throw away, you know, 20 hours a week to see if I can go through the brutal process of just constant iteration to like see if I can pull it off.

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And I think that's kind of how the conversation at least started. Were you about to say something there, Andrew? Um,

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I think, I think just, I think the full end-to-end thing, just 'cause I feel like we've touched on like some of the in the weed stuff, is that like David and I have known each other. Um, David's obviously very talented.

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We kind of-- he had like, had some familiarity with the space, kind of pushed me on it, and I needed help at the time and was like starting to think in the back of my mind about hiring.

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Um, and then we did basically make a role for him. Ultimately, we landed on chief of staff.

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I'd say what he actually does right now, and you can ask him, is everything from like, he's helped us spin up how we're gonna handle, like a lot of the infrastructure for how we're gonna handle international taxes.

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He does like, he does, spends probably 50, 60% of his time on go-to-market. Um, like, but, and then, I don't know, like I'm sure there's like half a dozen other just like random-...

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things that, like, have to get done that I'm running out of time for.

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Um, so I think the way I'd, like, sum up his role is that he has been-- he has come in and ultimately helped to give me leverage on my time, um, which requires someone I trust who's got, like, enough context too for that to work.

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Like, you have to have a lot of context for that to be effective. Um, and, and just willing to, like, hustle and eat, eat glass 'cause I'm eating glass, our whole team is eating glass.

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We're just at a stage of company where, um, everyone is just, like, grinding through it to try to get, try to get to where we wanna be. Um, so I'd say, like, David...

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And I think, like, your, at least for early-stage chief of staff, like, role, if that does exist, um, probably done best looks something more like that even if it sounds very glorious.

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It's like I, I don't know, David could tell you, but I think a lot of it is, like, not glorious. It's just, like, doing whatever it takes to win.

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Um, and he, he's, he's said that he's willing to do that, and I think I was impressed through the process of, one, just working with him. It was clear he was down to, to do that and could, could do that.

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But then I also, like, I, I did know about David that, like, if you had just been another junior V-... I've met plenty of junior VCs that, like, wanted this job.

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I've had some of them reach out to me about, like, jobs like this before. I would not have made that hire because frankly I don't think most of them want to grind like that.

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Um, and I think something I did know about you, I've always been impressed by you, not only that you were able to, like, potentially get into interesting deals as an investor, but, um, very few ju-junior VCs can network with successfully or, like, help raise capital from LPs, and that's something you have, like, a track record of doing oddly enough.

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Like, you've, so you, you've had, like, some interesting experience, like hacking things someone of your age should not be able to, to hack. Um, and, and you've, you've done that before.

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And then I did know, I, I went through one weekend, I didn't, I didn't tell you this, but I... when I was thinking about finalizing the decision, I just read through your entire Twitter history.

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Um, and I think I found, like, a thread about, about, about you, like, that you were, like, taking notes on, like, having sent, like, 1,000 cold emails or something like that to LPs and just being like, "Okay, yeah, this guy, this guy can, like, can definitely..."

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I mean, he's already showing me he can grind, but if, like, I was, like, building my mental model on, like, what I thought of you and then, like, what I...

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could you kinda, like, come in and figure out all of the things you would have to figure out to do it? Um, and so, and it's, it's, like, worked. We made the bet.

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Um, we did, like, a quick speed run of just getting him to meet the rest of the team, but it's, it's obviously been, been fantastic or we wouldn't, uh, we wouldn't, uh, we wouldn't both, both be here right n- right now, so.

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David, is there anything you want to add to the, to the 1,000 cold emails [laughs] or anything else that- [laughs]

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Uh, I, I, I think, like, the, my, my, my role and responsibility as of today if I summarized it in three sentences, um, if it's something that we need to do but, like, it's not being done yet, I have to cold start it and, like, try to systemize it and, like, get it to kick start off and working.

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And, like, that's kind of, um, repeatedly sending 1,000 cold emails but, like, in different types of processes is, like, what I do.

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So I think from, from that perspective, like, every new opportunity is both exciting but daunting at the time, but just kind of have to digest it and chew through glass, as Andrew said. I, I think that's just it.

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It's not, it's not like- You do more than send cold emails to, to be, to be clear. [laughs] But, uh, but yeah. Um, yeah.

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But I mean, like, just, like, everyth- I mean, he, I think he's, like, taught himself how to, like, edit, like...

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Like, we, we, we've, we create a good bit, or we've been starting to create more, more content and so, like, I don't know, you've taught yourself how to use a ton of, like, AI tools I didn't even know exist to, like, help us just edit that without paying an editor.

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Um, and we're, we're gonna, like, pay, pay editors at some point, but it was just like we don't even wanna mess with finding an editor. Let's just, like, do this and see if it's any good.

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Um, and so y- I think you, I can just kinda, like, throw you at something and you'll, like, figure it out, and that is, um, that is more rare than it...

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Like, it j- it sounds like people talk about startups and they go, "Of course, like, that's, like, startups," but, like, most, most people are not capable of, of doing that, nor do they wanna do that.

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That's, like, scary and uncertain and often quite, quite a bit not fun, especially 'cause you're doing that while you also have, like, eight other things to do. And, like, and I'm sure I'm not easy to work with either.

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I pro- I, like, am constantly, like, my, my life is like a triage machine of, like, what is the most important thing and trying to make sure I'm working on that and not getting at least too derailed by just, like, the sheer amount of stuff that happens on a, on a day-to-day basis.

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And, um, because that's my life, you also get affected by that, so it's like you also have to triage and figure out how to, like, how to prioritize the most important thing.

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Um, and so but you've just, I don't know, like, a lot, it's like you're willing to suffer, and you're willing to, um, like, do whatever it takes to win.

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And I think, like, at an early-stage company, that's kind of what you want 'cause, like, there's, there's no way to win without some level of suffering, and you gotta do whatever it takes to win.

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Uh, and how have you been thinking about the, like, the chief of staff role, uh, Andrew, and, like, has this, like...

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It, it sounds like, you know, this kind of, like, organically kind of emerged and, you know, were you thinking- Oh, yeah, totally. I, I'm, like, a hater, I was a hater on this role in the past, so.

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[laughs] What, what, what was the, what was, uh, like, behind some of that thoughts before and, like, how are you, how are you, like, kind of, I guess, like, more broadly thinking about it now? Yeah.

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I think before, I think some of it is more grounded in the stereotypes than it is, like, is, is there any utility to the role?

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Like, some, some people, it was you, David, and some, some people you and I both, both know and, and are friends with who are, like, I, I...

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that I think really highly of who have been chiefs of staff, who are chiefs of staff, who are just, like, involved in that community. So I think, I think it's a useful role.

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I'm not, like, I've never been a pure hater on the role. Um, but I think for early-stage companies I've, I've, I've had a l- little bit of, bit of shade towards it.

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And, and the reason for it is that I, I'll get DMs from, I don't know, like, some kid who working in venture or some person that's, like, I don't know, trying to pivot from consulting, banking, an MBA student, like, what-whatever, like, trying to, like, be, like, work at a startup, and they pitch me on s- like, strategy or chief of staff role, and it's, like, and it's, and they're all, like, often, like, the same thing, like, at, at the same time.

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And fu- fundamentally, like, at its core in an early-stage company, you're, there's, like, two main things, and I'll maybe add, like, a third, but there's two main things you're doing, you're building or you're selling.

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Um, and then there's, like, a little bit of just, like, a, a general third thing of just getting stuff done that enables the, the first two.

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Um, and so you need to be able to build, you need to be able to sell, and you need to be able to get things done, um, and make sure the things you're getting done, like, are hopefully, like, enabling, like, the, the top two things.

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And so I think that is just, I think at the e- early stage-A lot of what pe- attracts people to the chief of staff role is a lot more of, like, the prestige of being chief of staff to a CEO, the, like, you're gonna, like, get all this exposure to all this, like, strategic things and executives and cross-functionalness.

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Um, and I don't think any of that's bad, but I think that what that actually looks like is it's more of, like, a series A, B, C company probably.

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Um, e-even, even series A might, might be too early, where it's like you are starting to have an executive team, and there, there is, like, stuff like that, and maybe there's, like, more need for that kind of role.

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Whereas in an early-stage company, it's like there's, um, there... every single person is an IC to some degree, like, like David said earlier. Um, and so you need to be able to contribute in that way.

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And if all you're doing is... If, and there's, like, not a lot of strategy to be done. Um, and so I think...

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And, and then I think just a lot of the work is unglorious because you're probably gonna be, like, I don't know, like, a lot of chiefs of staff at early-stage companies probably own, like, finance.

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They own, like, billing, like, making sure, like, like David has sent me two reminders in the last two days that, like, we are, like, behind on, like, send, actually a-asking our customers to pay us.

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Um, and so, like, [chuckles] 'cause I, I, I always, I like signing contracts, then I totally forget, "Oh, yeah, like I haven't sent that invoice yet."

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Um, and so it's, it's just, like, uh, it's, like, thing, things like that.

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Like, I'm, I'm, I'm half in jest, but it's like, it's like, so it's, like, some of it is like, yeah, it's, like, helpful to keep the trains running.

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But, like, like if, honestly, if Da- uh, if David, I could hire an A- EA to help me keep the trains running, whereas, like, David, David is, like, fundamentally, like, someone I trust.

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So I, I think, I think what it works for chief of staff and why I changed my mind is, like, generally I bucketed most people. They don't really wanna do the work.

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They're attracted to it for the wrong reasons, like status, um, a type of learning they're not even gonna get. And just generally, like, I don't...

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And also too, it's, like, not clear to me how are you even gonna be able to roll up your sleeves and get anything done, because if you just wanna sit around here and, like, be smart and do strategy, like, I don't have any use for that.

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Whereas, like, David came in and was like, like, he actually originally pitched me on being, like, a, like, a sales, sales, like, an entry-level sales person. It was like, he was like, "I could potentially do this."

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Uh, he didn't really pitch me on it, but he was like, he was like, "Well, if we were gonna work together, I guess this is, like, one way it could look like," is, is kind of how he positioned it.

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And so, like, that's not the title or role we ended up going with, but theoretically, I mean, he was, like, down to just go be, like, one of the first, like, not, not me sellers at the company.

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And that, like, s- I think says a lot about someone, 'cause most people look at an entry-level sales role and they're like, "Oh, I would never do that."

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And so, like, he was willing to sell, he was willing to roll up his sleeves, he was willing to do stuff.

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And I think if you're willing to be a jack of all trades who just does whatever it takes and is, is sm- or, but, like, also, I think the thing about chief of staff and why I changed my mind is, like, he, he fit a lot of the things you'd look for in a chief of staff, but also the willingness to just eat glass and, and do the work and actually figure out how to do the work reasonably well.

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Um, and I think he brought the kind of, like, he's, he frankly could probably have, like, much more fancy jobs than, than, than this one if he wanted to at, like, later-stage companies. But I think, um,

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I think what gave me additional confidence is that he's smart enough and, uh, I, I guess, like, I, I trusted him, and I think that that is important in this role specifically, 'cause you do get a lot of, like, access to sensitive things around the company and just, like, how you're thinking about the company.

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Um, that, like, if I just hired, like, someone to do operations, for example, they probably wouldn't get access to most of that stuff. And so I think,

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I think because of the fact that he brought, like, a willingness to do whatever it took to win, even, like, the most unsexy or most un- like, boring, difficult tasks, but also he was, like, extremely smart and had good judgment, and I could just, like, generally trust him with, like, the more sensitive stuff that is a little more strategic.

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I think, I think that combination is a bit more rare at the early stage at least than you, one would think.

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Um, and so, like, I don't think most chief people applying for chief of staff roles necessarily wanna go take demo calls, you know, and, and do a bunch of selling.

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And so I think, I think it's just, like, an int- rare mix of enough of the right things that made sense for at least what I, I would want out of a chief of staff at, at this stage of company.

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David, anything you wanna add to that? Yeah. I mean, honestly, the only other chief of staff that I knew before this was Zach Davidson, and he just kind of, like, did everything to, like, get things done.

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So, like, to me, like, I just [chuckles] never, never really understood it as, like, a strategy, like, high-level role. Even now it's just like, I just go do it. Like, just, just, just do things.

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I mean, that- that's all I do. Just do things. Like, what- yeah, just, just do things.

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[chuckles] Like, if, if there's a body that needs to be thrown in, like, just doing things right now because we need this done today, I just go do it. That's all I do. Amazing. Okay.

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Uh, so I think we've, we've kind of, like, teed up the role a lot here and, um, I guess, like, from a practical perspective, um, it's been about, I'm not, I'm not entirely sure when, like, the, the contract kind of thing started and stuff, but generally a couple of months, uh, of working together.

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Um- Yeah, full-time for, like, two months, I'd say. How would you...

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Like, what, in terms of, like, um, like, one-on-ones or text messages or huddles or, like, what would you say is, like, your, like, your cadence of communication in terms of just, like, making, of getting stuff done?

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Um, like, is there, like, okay, every Friday we get together and, like, make sure that, you know, these things on the, on the to-do list got done.

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Like, what, what, like, have there been things that you tried that didn't work?

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Like, what, what have you all, uh, found in working together, uh, in terms of communication and getting things done that's been working well? You know, if you've got to take David, feel free to share.

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I think, I don't, I think we're actually pretty light on structure. And generally, th- maybe this is because I am default.

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No, I wouldn't actually, I actually say I'm a relatively structured person, but I'm light on, on, like, we are gonna have, like...

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Like, I, I don't love standing meetings, and so, like, we are very, I'd say, like, very standing meeting light as a company.

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Like, we have one single, I think, I guess two technically, one single standing meeting across the company, which is all-hands, and then we have one,

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um, I think, like, engineering has, like, a, a stand-up once a week or something like that, but that's it. And so we, so what we do though, we, we, so I, I think we just default to, like,

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um, a lot of, like, just, like, constant communication I'd say is, like, a better way of looking at what we have going on.

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And so it's, like, like, we Slack, we text-Sometimes we have two different threads going on at the, the same time over Slack and text. We're on email threads together.

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I'm generally trying to, like, dump, dump stuff to David, keep David looped in at all times. And then if we ever need to go over something, he calls me, I call him, we huddle.

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Um, and then, th- then if we have, like, external meetings with customers and, and stuff like that, he's, he's involved in, in quite a bit of those.

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Um, and generally he has, like, unfettered access to my calendar and, and all that kind of stuff. But I'd say in terms of how we work together, it's just, like, this is...

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I think the only maybe, maybe one thing that would stand out is we d- we do, we communicate constantly. We have a Slack channel, um, that we,

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like, a, an async channel where we're just, like, kinda, like, constantly sharing, like, what, like, the other's priority is and, and, like, what's top of mind or what needs to get done.

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Um, and then I think, but I think we're, I think it's just, like, constant other, other than that.

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'Cause we, even that, like, Slack channel, like, half the stuff that, like, I said was top priority, like, two days ago is probably, like, not true. Or it's probably, it's probably shifted a little bit since, since then.

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And so, um, that, that's, like, how I feel like we handle it at least. And then if we need to get on the phone and hash something out, we just do it.

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Um, I, and, and we've not, I think we've stayed away from complicating it more than that. Um, yeah, Da-David, anything you'd a- you would add to that? Yeah. Sounds about right.

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If I'm not sleeping or if Andrew's not sleeping, um, we're on call. That, that's kind of how, how it works, you know.

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And this, this one Slack channel, it's, like, a specific, like, call, like, workflow or, like, get stuff done, just do things channel or like- We just have a...

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So we have, like, a bunch of channels in the company, but, like, we, I'd say there's, like, probably, like,

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since David's pretty involved in go-to-market, we have, like, we have, like, a couple g- like, a go-to-market and then just, like, an active deals channel that we, like, hash out a bunch of.

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Like, it's more of, like, and we, even though he and I are doing most of the work there, um, it's, we, we kinda do that publicly just so the rest of the s- team has insight into what's happening.

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And then we have, like, an async. It's literally, like, we, we use this for a lot of our Slack channels. It's, like, async dash, like, whatever.

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And so, and that's usually for, like, a, like, not, like, unless, like, I tag you, it, like, probably doesn't have to happen this minute.

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It's, it doesn't need to be a DM, but it's, like, a place to just keep track of, like, work that's going on.

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And so w- I, my co-founder and I have, like, d- done this in the past at different companies, and so we, we, we use these channels. Like, I have, like, two or three of them with a couple folks on the team.

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Um, and so we just, like, it's, like, a private channel. It's just us, and it's kinda, like, we can just, like, share whatever.

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Like, it's usually project-based, and so maybe it's, like, we need to go invite, like, 50 CFOs to this event we're hosting in a month.

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Um, so I, I might, like, do almost, like, a subject line level sentence and be like, like, "Hey, we need to invite 50 CFOs to this event. Thread it."

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And then I'll, like, in the thread, add contacts, add what's going on, and then we'll kinda, like, hash out, like, what needs to get done from there.

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And then, and then the nice thing about that is you can come through and just, like, track what's happening and relink to stuff so you don't lose contacts. It k- keeps it a little bit more organized.

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Um, so I think that's probably, like, the main, main thing there. O- one thing I have been trying to get better at, I would say, that's, like, not, less, like, of a...

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I don't think it's, like, a, oh, it's, like, a cha- channel or something like that.

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A thing that I think, I mean, I haven't even told you this, David, but I, I am attempting to be better about how I communicate just on general work that's happening across the company, especially with David.

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About, I think I have a tendency to just co- I, I just, like, stream of consciousness whatever's on my mind or whatever I'm, like, thinking about, about a given thing. And I think I sometimes,

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everything I say can come off as, like, either urgent or, like, I want this done now or, or whatever.

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And I'm trying to be a little more explicit about, um, staying when something is, like, actually top priority versus, like, this is... Or, or, like, this is, like, a drive-by thought.

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This is, like, not necessarily something that needs to be actioned on right now.

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And I think it's, like, but, like, generally it's, like, just easy for me to, like, say stuff, and I say stuff in a pi- in an opinionated way, and so it, like, can come off as, like, oh.

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And it's not even just with David. This is with, like, other people on the team.

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Um, so I think something I've been attempting to do, actually, is, like, I think in David's role, it's hard because technically, like, you're just, it's, like, it, everything feels like it needs to get done all the time.

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And things that I feel like are obvious to me, like, he has to kinda, like, do his best to, like, always understand, like, what I'm thinking about and what I think is the most important thing.

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And, um, and we've had not any huge issue with this, but it's, like, I've, like, noticed at times it's like, wow, like, we thought that was the most im- David thought I th- was saying that that is the most important thing, or s- or somebody else on the team thought.

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And I was like, that was, like, a total drive-by just thought that I threw out there. And I was not, I didn't take it that seriously.

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And, and I, and I, looking back, it's like, well, I didn't really give more context than that.

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So I just think, like, trying to be more explicit on just, like, especially when you're remote, and it's, like, you're, like, you're doing a lot of the stuff in, like, like, text, Slack, whatever.

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If you con- It, it's easy to lose the tone or context by which someone is saying something. So that, that's been a, a more recent change I am at least just attempting to make. Nice.

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And I, and just to, with the, the async channel, I, I think I remember some, like, viral threads or some threads about that with, uh, like, from OnDeck back in the day.

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I feel like I remember, like, some of that being shared about- Yeah. Yeah, that's probably where we got it originally.

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Yeah, there's a thread, there's a, there's a thread, I could find it, um, that went vi- did, did go viral back then.

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But it, it's, I f- I find it, I'd say for Slack management in general, I just, I find it, like, having... It's, it's both, like, the channel names.

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Like, there's some channels that are, like, async specific that, uh, I've, I've seen people do for, like, one-to-ones.

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Like, if you're managing someone where it's, like, you, for us or any work we do together, like, we're gonna have this channel for that. Um, but I think generally just as a company, we try very hard to structure.

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Like, uh, it's not perfect, but to try to keep things, like, where, like, you make people use threads because it does make it a lot easier to track information and, like, keep channels from getting too noisy.

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Um, and then the, a more, a third one that's more specific to TaxFire that we've started doing is that I think a great thing about in-person work is you just kinda can always, like, get everybody together for something, versus when you're remote-I think there's a, there can be this tendency to like, "Oh, we gotta schedule a meeting for this," or, "Oh, we've gotta like, whatever."

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And like half the time the scheduled meeting, it just needs to be like a two-minute conversation.

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Um, or even if it does need to be a longer conversation, it's like now, now because we've gotta schedule it, it's like we're like essentially putting it off versus doing it now. And I think we have...

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And this is coming from my co-founder, but he kinda has this habit of just being like, "We don't set a lot of meetings, but also like I'll...

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Like, you can just call me in Slack or call my cell, like whenever, it's fine."

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So he, he just kinda operates that way, so if like we're like dealing with something and clearly we should probably talk about this, instead of like, "Okay, we're gonna schedule a meeting for 4:00 PM tomorrow to talk about this," it's like, "Cool, let's just huddle right now."

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And like, and it might be a five-minute huddle, it might be an hour huddle, but it's like, we'll just like, "Okay, we're gonna like hash this out." And I think that's like making...

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And this is like a, such a touchy thing, but you wanna like culturally lower the barriers to just getting stuff done and just like, like, like cutting through noise as much as possible.

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And I think in a remote environment, you have to be more intentional about that, because you do have to be more structured in a remote environment for it to work, um, than, than you might have to at the s- as the same size of company if everybody's in person.

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But you also, you wanna make sure it's not so structured that like we just, everything turns into like a, like, like a process to just like get a thing done.

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Um, I don't, I don't know if you have a perspective on, on, on that, David, but I, I think that's something we've done like an okay job at rel- relative to some of the other remote companies I've been a part of.

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I think so.

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And one of the reasons for I think also in me kind of making the decision to join full-time after the two weeks of, you know, 20 hours a week is it's, it's run very professionally versus a lot of startups that I've seen as an early stage investor.

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And like that, I think drove a lot of conviction into kind of how, like, is this gonna, company gonna survive and like make it?

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And like, uh, like make it and like success, succeed and thrive and like grow into like something really big.

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Um, and, and I think those types of, um, patterns of how people operate within a company are like very hard to set, um, especially when, you know, it's, it's such a young company, was I think something that I was like very drawn into.

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Love. Cool. Um, anything else that we wanna share, talk about, about the role, about like learning so far? Obviously, it's only just been a couple of months.

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Um, anything else that you wanna share to either like existing chiefs of staff or aspiring chiefs of staff that might be listening to this?

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Um, I guess for me, I mean, uh, so I, I, I work currently like remotely out of Korea. Um, Andrew's in New York. Um, if you're an engineer, you can maybe make that work, um, easily.

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If you're not, then like you have to kind of stick along with where the CEO is. So I've been working, um, you know, kind of like an owl in the past, like past two and a half months. But, um, it's what it takes.

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Um, you have to do it. Like, if you, if you don't do it like that, um, the company's not gonna make it.

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And like, if the company can't make it, and like, if you can't do it, then like, you know, probably not the right role for you.

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But like, if you still can like pull through and like grind through it with like eating glass, I think, you know, definitely could make it possible and work.

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And people freak out, um, when, when I, when I say that like I, like what time, what time is it in Korea right now? Just like, don't, don't think about that. Like I'm working in New York.

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Like, you know, it's just like y- you have to do it. And I don't know, it's, um, time goes by really quickly if you're putting your heads down and just like grinding through glass. Like it just...

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And, and, you know, you try to make the numbers go up, right? So. David is exceptional.

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Not a lot of people would be willing to do that, and I think that, that, uh, that level of like just commitment and willingness to, to grind and go just m- like help, help us win, um, it means a lot.

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It, it's also embraced I think a lot of like trust and respect with like not ev- not only myself, but a lot of the rest of the team.

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And I think like very, very quickly he kinda went in from like nobody on the team, like we're...

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Like Andrew just like, especially 'cause everywhere else we'd run a very structured process to, to bring anybody else onto the team. So David's like the only person we just kinda shotgunned in.

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And, um, we didn't, it wasn't fully shotgunned. Like he, he met everybody else normally before we went full time.

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Um, but I think he just like really, really, really impressed people really, really quickly with just like how hard he worked and how much, how much impact he had fast.

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Um, so I'd say for if you're gonna do the role, I think that's... And it's an early stage company, probably even if it's a later stage company, like that first impression you make is kind of gonna set the tone.

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And so just like, whatever it takes to like come in, make impact, get stuff done, take something off people's plate. Don't, don't ask for permission kind of thing, I think is important.

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And then I think second, I think Da- David does a really good job of is he is, he is good about trying to understand like where my head is at all the time.

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And I think, I think for this to role, role to work at this stage of company,

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probably any stage of company, you do have to just get inside whoever you're working with's head or, or else like it's just like you're just gonna miss so much context.

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'Cause especially for us, like at our stage, like my brain is kind of like the c- is like kinda like the company in some ways, and we're, we're trying to scale out of that over time.

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But David is like a bridge helping me scale out of that. And, and so it's, um, I think just like being literally willing to like double-click on, like un- trying to understand the, the person you're working with.

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And if you're like a chief of staff working with like a founder, um, we are not always the best, as good of communicators with this like operational management stuff as we should be.

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So getting into that person's brain will, will I think go a long way. Um, and just like don't be afraid. Like no question is too dumb.

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Um, but like ask the questions and like force, force someone like me to be specific about what we mean and, and you'll, you'll probably just be more effective more, more quickly. Cool.

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And, uh, if people wanna stay in touch, uh, Andrew, you're pretty active on, on, uh, Twitter and LinkedIn. Taxwire, taxwire.com.

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Yeah, taxwire.com is, uh, the website if you need any help with, uh, global sales tax compliance.

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If you're a sales company or commerce brand, uh, accounting firm, just like anybody that sells stuff all over the place, we, we can probably help.

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We are very good at cleaning up the mess, and we offer like, um, like, uh, we, we do like free consults all the time. Um, and then David's at david@taxwire.com. I'm andrew@taxwire.com.

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Um, I'm on Twitter, I'm on LinkedIn. I think David's on both of those places as well. So DM us, whatever. We're, we're pretty, pretty easy to reach. Sounds good. Thanks, guys. Really appreciate it.

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