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Hello, hello, this is, uh, Tom from Chief of Staff Network, and I've got with me Andrew, who's the co-founder and CEO of Taxwire. Uh, welcome, Andrew. Hi, sir. It's good to see you. Good to see you too.

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So tell me, what does Taxwire do? We do global sales tax compliance.

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So if you sell taxable stuff in multiple US states or countries, we do all of the stuff that goes into understanding what you need to do, registering, and ultimately, like, calculating, filing, and remitting those taxes all around the world.

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So it's effectively like a, a, like, SaaS platform for automating most of the ongoing stuff, and then we kinda have, like, a AI-enabled, like, in-house tax team that kinda, like, manages some of the services around it as well.

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Cool. Everybody hates taxes. Why is this important? What... Like, is- Yeah. Is this even an issue for most companies? It's...

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I'd say, um, we'd probably be the worst business in the world if it wasn't, like, literally, uh, illegal to not do taxes. Yeah. Like, I don't think it would be one of those things that no one would ever, ever wanna do.

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And it's, it's like a pro and con of being in the space, but because it's a legally required thing to do, like, you have to do taxes. So effectively, like, it's like cover... You have to... It's like CYA, cover your ass.

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Like, you have to do it. Um, it costs you big money, in our case, if you don't do it.

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Um, and so-- and then, like, you kind of probably get fired if you'd, like, do it super, super incorrectly as, like, a, a controller or CFO person. And so, um, yeah, but that's like, that's it.

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A-and it's also j- it's become a lot more complicated in the last five to 10 years with a bunch of changes in US and international tax laws to where now companies have to collect sales tax or va-value added tax in way more places than they used to.

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Um, and s- a bunch of the existing solutions on the market are, are pretty terrible, um, at least in my experience, were pretty terrible, and that's, that's why we started Taxwire. Nice.

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So you must-- You work with a lot of early stage finance teams. What do you think the ideal early stage finance team looks like? Yeah. Yeah.

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So most of our, just for context, m- the majority of our customers are either accounting firms, like the fractional finance team, like fractional controller or something like that- Yeah...

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um, or, like, controller and CFO at, like, a growth, growth stage company of some kind, like mid-market. And so I'd say these days, it's interesting. The...

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I think, I, I think honestly it usually starts with, like, there's probably a chief of staff or biz ops person that, like, takes it off the founder's plate early on, um, or they're just like, they've got, like, a really great full stack accounting firm doing everything, the founder just oversees.

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That's kind of what you see at seed stage and maybe, like, Series A. Probably around, like, Series B plus, you see a head of finance, a VP of finance, someone like that come in, and they're gonna...

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Still an accounting firm in place. They're overseeing everything. Um, and the, like... A-and then at some point, as it, like, you...

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And you li-literally I've, like, watched this happen now with some of our customers, you'll see a controller come in probably around that time.

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But they might go, like, with, like, VP of finance just or VP of finance plus a controller for, like, a really, really long time.

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Like, these days, I think you're seeing companies, like, do that up to, like, even in some cases, like, seventy to a hundred million in revenue in, in a few cases without any...

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They might have some, still some fractional help on, like, tax and stuff like that.

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But it's, it's pretty lean these days, and I think a lot of the tooling, this is a thing people are excited about now is, like, more tooling to effectively, like, make it easier for those companies to go as far as possible with a, a very lean team.

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Makes sense. And, uh, especially if it's ideal that you're running at a negative gross margin, right? Then- Yeah. Yeah. Literally. Yeah. [laughs] Literally. Yeah.

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Uh, so, you know, obviously kind of the stack is gonna s- change a lot as you scale up as well.

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What are the, what are the tools of choice that you're seeing across the best finance teams today, other than Taxwire, of course? Yeah. I... Yeah. Yeah. Of, of course. Yeah, yeah, yeah. Of course.

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Gotta, gotta show ourselves there. Yeah, yeah. Um, yeah. I'd say the, um... There's, like, there's kind of, like, the back office HR, like com-the compliance side, so, like, sales tax compliance, back compliance.

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There's, like, you'll usually see for payroll and HR, you might see like a, like a Rippling, Justworks, um, on, in the US side, maybe, like, Deel if they're doing a lot of stuff internationally. Those are the...

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I'd say, like, once the finance team is in charge, honestly you do see Rippling replace, uh, Gusto quite a bit. So it's, like, probably Rippling, um, is...

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Rippling or Justworks, I'd say are the two most common, um, and then maybe something else for the international side of things.

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You might have like a Mozy or something like that in there for doing, like, uh, like, secretary of state and stuff.

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And then, um, you'll probably see like an account, like a, a tax firm, like a Ribbet Tax or s- or someone like that out there for, like, or like, uh, maybe a bigger, bigger, more traditional firm doing income taxes.

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Um, and so those are, like, mix of service and software. And then Ramp is by far the one you see everybody using in the, uh, on, like, the, uh, the cards and expense management side of things.

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It is, like, hands down, like, probably the most loved product in the stack right now for, like, uh, controllers and, and finance teams. And they're just, like, their customers love them and it's really impressive.

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Rippling actually probably not as lo- Uh, maybe I shouldn't say this. Probably not as loved as it used to be, but, like- At least-... people, like, are on it, but I, I do see a lot of unhappiness with it these days.

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Uh, I... Then I think, I think Relay is one we're seeing a lot more of.

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Like, those guys have done a really, really good job on the ERP side for, for tech companies, and we're seeing a lot more folks move, move over to them.

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So Relay is, like, really up and coming and giving NetSuite a run for their money.

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Like, usually it's QuickBooks, and people are, like, hanging on to QuickBooks for as long as possible 'cause no one wants to go to NetSuite.

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And then, um, and then at some point, they either go to NetSuite when they hit that, like, maybe, like, multi-entity point or, or, or now you're seeing people start to look at newer ERPs like, like Relay.

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Um, and then at some point when, like, the, the transactional complexity is getting up high, you might s- like around, like, fifty, seventy, a hundred million in revenue, depending on the business model, you might see like a close management tool, like a FloQast or a- That's great.

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Yeah. Definitely, uh, if, if you haven't made the move to NetSuite yet, I would strongly consider not doing for anybody who's listening. [laughs] Coming, coming from someone who knows the pain. Yes. Exactly. Yeah.

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Exactly. So one thing I, I think most of those companies are, are s- building a narrative around, uh, and you're seeing it kind of across the ecosystem, like the finance plus AI thing. How real is that?

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Are you seeing companies actually use AI to do any mission critical tasks, or is that- Yeah... we're not there yet? It's both real and it's a little bit bullshit, um, is, is like what I would say.

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There's, on the real s- I think right now, like, AI, this is probably true in other industries as well. I, I think, I think it is not...

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In actual practical use cases, I don't think we're as far as, like, definitely software engineering or some other fields, uh, like legal, for example, in, in the finance accounting stack.

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And I think the reason for that is because it is so deterministicAnd so, like, often you can't be wrong or you, like, need to be highly precise.

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That large language models hallucinate, they're not always right, getting all the context there is really hard. And so I think that- Generative AI there. Yeah. Yeah. And so, like, you don't wanna do...

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No one wants their tax engine to be like, you know, like, uh, maybe it's, maybe it's w-wrong ten percent of the time. No one, no one wants that. And so, like, it's- Yeah... um,

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that, that-- So I think that's one of the things holding it back.

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And so even where you do see AI being effective in that side of things, it's usually from someone who actually controls a very key deterministic workflow, um, or, like, source of truth at the bottom.

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So in, in, uh, in expense management, like, the reason Ramp has been so good at automating a lot of the stuff in and around the ex- the expense process or, or bill pay process, has been because they have deterministic financial rails that are, like, not gonna be wrong.

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And so they're ta- they're able to, like, build, like, mini agents or, or, like, use, use large language models around those deterministic rails, and they can be much more effective because you're, you're, uh, you're effectively constraining the, the ability for hallucination and just, like, con- con-confining it to this, like, very specific problem on top of something that won't be wrong.

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Same thing in, like, ERP, Relit is, like, built a lot of small agents around their, their rails. Like, we're, we're doing some of this to an extent around, like, just we-- our engine won't be wrong, but we can...

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What we've found is that's really, really effective with taking unstructured data and putting it into your structure. A lot-- I honestly think a lot of the things are small, actually.

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Small workflow that maybe takes, like, an hour a week or two hours a month. But it's just- But adds... a lot of small, small things that you see where it's being effective versus, like, the whole product.

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I think the other... And then I-- So I think that's, like, the stuff that's working on the software side. Uh, but I, I think the couple other observations, the, um...

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I think the, I think a lot of i- people-- I had a guy in SF at a very high, um, office of the CFO, like, AI-ish company t-like, tell me this, of like, a lot of the features they have that are, like, um, AI-oriented are great for marketing and great for getting people excited on demos, but are really not the re- the, the biggest actual value of the product.

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But they, like, lean into it really aggressively in marketing and sales because it's like, it is, like, bringing in a lot of business.

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And so I think you're seeing right now that, like, everybody has to tell the narrative, because to some extent, there is some truth there.

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But even if the narrative is larger than, like, what's working today, it's what people wanna hear, and people are excited about it.

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And so I think there is, like, a lot of hype for, for good reason, but also 'cause it works from a marketing perspective.

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Um, I think the thing that's even more real than, like, what software vendors are doing is that, like, just individual people at, like, these, like, smaller finance teams are, like, just kinda, like, vibe coding stuff or, like, using ChatGPT to, like, do a lot of their own, like, automation.

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I think there's just as much happening, um, with, like, the out-of-the-box tools just to make stuff faster, easier, et cetera, as there is from, like, your SaaS tool is getting agentified or something like that.

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Yeah, that makes sense. We're, we're definitely seeing a lot of that in other, uh, in, like, the chief of staff and biz ops roles as well. Um- Yeah. Yeah. Yeah. Okay, cool.

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So, um, we're gonna do a little bit of a, a tweet review 'cause you've been putting out some bangers recently. Um- Oh, gosh. [chuckles] All right.

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So- I'm always, I'm always nervous when someone's like, uh, actually making me, uh, back up, back up the, the random stuff I say on the internet. Look, that's the, um, that's the whole point, right?

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We're gonna hold you accountable. [chuckles] Uh, cool. Okay.

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So starting out here, y-y-you, you, uh, tweeted that more young people should posit-position themselves to join companies as interns or AI ops people to automate stuff across businesses. What's...

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What are you seeing there that's been interesting? Yeah.

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Uh, and this was almost, this was prompted a little bit by just, like, I get enough, like, inbound and pitches on, like, "Let me come work at Taxwire or do this role" or whatever. Do strategy for you. Yeah. Yeah, yeah.

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Yeah. Yeah. Uh, like, you could see that, but then also just, like, looking at what seeing some customers hire for.

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I actually just did an accounting conference, acc-accounting firm conference, and it was really interesting to see there were a couple, like, young kids there who were, like, not even, one of them hadn't even graduated, but he was, like, super, like, AI native and, like, knew...

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Was just, like, really, like, way advanced on, like, how to use AI to, like, automate a lot of small stuff. And he was actually, like...

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I bet he probably walked out of that conference with, like, five job offers from different firm owners- Okay... who wanted that in their firm.

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And so I think th-this tweet to me was just like, I think if I was young and getting started out today and I didn't know what, like, the hell to do, you have t- you have time, honestly, uh, more so than a lot of other people.

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And, uh, and, like, there's, there is no, like... You're not behind a bunch of people that are AI experts, um, 'cause, like, everybody's, like, figuring this stuff out.

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So if you actually wanted to, like, get an opportunity and you don't have, like, much on paper to offer, learn how to use these tools, like, like, the out-of-the-box ones, ChatGPT, um, the, the vibe coding tools like Lovable.

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Actually, like, our, our chief of staff, like, pitched, pitched me initially on working together off, like, a prototype he built on Lovable. Yeah.

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Um, and, like, and then, like, figure out, like, how to automate stuff and just come in and pitch yourself as, like, "Hey, I may not have a lot of traditional experience, but I know, like, how to use all these tools.

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I can prove it with some of the, like, proof of work that I've done here, here, and here. And I think I could come in and, like, just make the whole company way more efficient and automate a bunch of stuff."

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I'd be like, if someone sent me a cold email, like, with some pitch to that effect and, like, s-the smallest bit of proof of work, I'd be like, I would totally respond to that.

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I would, like, 100% respond to that, and I get a lot of cold emails. And it's, and I think, like, no, I don't see a...

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I'm aware of a few people doing this, but I think it, this is, like, a huge opportunity if you're just young right now and want an opportunity to just go do this.

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And this is way better than doing what everybody else is doing, or they're just spamming out the same emails at, like, effectively offering no value and, and, like, trying to cut through the noise.

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It's like, it's, it's a losing battle versus you could totally do this. And I think, I actually think a lot of companies would be very excited to hire young people, um, op- like, positioning themselves this way.

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That's super smart. It's not, it's not a volume game. It's showing that you actually care about the company that you're, you wanna go to. Yeah. Yeah.

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And I think, and I actually think it's hard to find, and it's not easy necessarily to find people that are super well-versed in all of these tools because many of them are so new and changing so quickly, that I think this is actually an area where you can build some pretty differentiated value that you won't have as, as much competition in.

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Absolutely. So speaking of caring, uh, talk a little bit about how you're building Taxwire and, and the company culture that you're, you're trying to build. Yeah. Um, I think culture's funny.

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Like, I, I, I, I think I, we care about it, but it's one of those things thatI think you think you're gonna write some stuff down in a document, in your careers page, whatever, and you're gonna have...

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And that this is gonna be our culture.

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And I think what actually happens, or I found to happen, is that you have some intentions, but, like, what will actually happen will be emergent of, like, who you already are as a person, the company you're building, what you try to do somewhat intentionally, but then also what happens unintentionally.

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And then, but very much the early people you hire, all of that stuff kind of forms and molds into the culture that you have. And I don't think any... I don't think you...

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This is I- why I actually think you see a lot of companies where they, like, write their mission, uh, statement or their values, and it's to- totally unaligned with what is, like, actually reality, is because it, it...

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all of this stuff, it's not like in a... You can write it down and-and it not totally be true. It's really, like,

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Graham and David and, like, all of the people we've hired and, like, the first 12 or so folks at Taxwire have influenced the culture maybe not exactly as much as me and Steven as founders, but, like, close, and they've been really, like, involved in that.

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And so, and I don't think you can just, like, take one, one person. So a- anyway, I think that-that's just been, like, a more of an observation that it's, it is emergent.

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It's not necessarily something you just do purely tops down.

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Um, I think what I've found is that there's, like, there are, like, threads of, like, what we've had to do to succeed as a company and the type of people that we brought on that have emerged as, like, big, big values.

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And as we see those things, we've tried to get more explicit about what those are. So for example, like, we are, um, we are an industry where, like, being wrong is, like, big cost both to us and to our customers.

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And so we, like, really, really care about swe- like, sweat the details, for example, because we have to sweat the details or, like, our customers aren't gonna trust us. Um, and so, like, that, that's, like, an example.

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But that was, like, that was not a thing that I think I would've written down at the start of the company.

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It was a thing that emerged from the, the type of company that we had to build and the type of people we had to recruit.

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So I, I think just, like, figuring out, like, what those things actually are and then trying to crystallize them such that you can then, like, once you kind of see, "Oh, this is a thing we do care about even if we didn't write it down at some point," then you write it down, then you make it clear, then you talk about it to future recruits, then you make it a thing that you communicate to the company, and everybody can kind of rally around.

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I, I think that's probably, like, one big one. The other one is, is probably more of just an observation that I think we have from right now in tech, and I think that's what this tweet is about.

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There's a lot of, like, talk about 996 and working tons of hours, and, and it's very, like, it comes from China, uh, and Chinese culture, and especially in tech is big on 996.

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You work nine hou- uh, like, uh, I think it's, like, nine to nine, six days a week effectively. And, and I, I honestly probably work more than 996 right now.

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And so, like, it's not even that, like, that inherently is a bad thing. But I think, I think it really is, like, missing the point a little bit.

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And the, the point is, all that matters is the outcome kind of in the grand scheme of things, and you need to work as hard as it takes to win. And at a certain point, actually working more is, like, not effective.

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Because if you... Generally, most of us are not just like, like, working in factories these days. We're, like, working knowledge work jobs. We're, um... Like, leverage matters.

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And so I think what we've found is, like, it's, um, the outcome matters. Um, driving people to work a ton of hours just for the sake of it isn't useful.

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Like, sometimes the best thing for your team to do is to, like, go sleep and go get rest. And I'm a, I'm a- actually a big fan of sleep.

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Whenever I've not slept enough, I'm, like, definitely not my best, the best at what I do.

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And so I could wor- I could theoretically cut two hours of sleep a day and get more hours of work a week, and I'd probably be way shittier at my job even though I've, like, picked up, like, extra working hours.

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And so our, our take on this is... And so we, we've, we've literally never once, like, set, like, "We expect you to work this many hours a week. We need you to be working this weekend."

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We just, like, we hire people that we think care, that we think are gonna work, like, work hard.

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Um, and then we, like, try to, like, communicate, like, this, like, shared mission and that we all have, like, equity and compensation and, like, a, a, a desire to go, like, accomplish.

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And then it's just like, "This is what we need to do. Like, let's, let's go do that thing."

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And the desire to work hard and work extra hours and work on weekends and, like, be thinking about work outside of when you're actually working all emerges from that. I've never...

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Like, people at Taxwire do sometimes work weekends and are, like, I think do care a lot about their work and do work really hard.

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But it's not like, it's not because I ever sat down one day and said, "Guys, we're going 996 now because all the YC kids are doing it, and therefore, um, like, we, we have to do this to, like, win in this, like, era."

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Like, I think you see a lot of that now, and I, I just think that's, like... I don't know. Maybe it's 'cause I'm a shitty CEO. Like, that, that could be it.

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Um, but I, I, I don't, I don't even think I could do that authentically 'cause most of the people that work at Taxwire are older than me. And so it's like they're gonna, like, look at me and like, "Are you a dork?"

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Like, uh, I'm, I'm, like, rambling here, but you hire great people, set, like, you align incentives, and you set, like, a correct, like, vision that everybody's, like, aligned around, and then the, the work will emerge, um,

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organically from that. And I think just, like, I think a lot of this, like, stuff around, like, 996 and stuff is, uh, it's, it's, it's, like, focusing on the wrong thing.

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And, and I think if anything, it's dangerous for, like, a lot of young founders out there 'cause I think a lot of people are just doing it because it's become a meme now, and they think it's, like, what they should do versus for...

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And I, I think if anything, you're just gonna come off like a very inauthentic leader.

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I think it's the classic Silicon Valley thing of, like, once something seems to be working, then everybody copies that thing regardless of whether they're actually copying it the right way.

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They don't think about the- Right... they think about just, like, copying the pattern, not about, like, why it matters. Um- 100%. Yeah. Cool. Okay. We'll, we'll pause it there. Um,

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we, uh, we're having this conversation in part because you're coming to Chief of Staff Connect, our chief of staff network conference in New York, October 23rd, 24th. Um- Super pumped. Chief...

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Yeah, we're pumped to have you. Chiefs of staff, are they thinking about sales tax? Are they thinking about building finance teams at companies?

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Um, funnily enough, like, we're seeing more of this, um, which is, like, been surprising for me. We have, like, a d- we have a handful of customers that are, like, are chiefs of staff.

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There's, like, effectively kind of... The, I think the thing, and you, you would know this even better than me, but about being a chief of staff is you end up, like, owning, especially at an early stage company.

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This is probably not true at- Bunch of random shit... Series, Series C. But i-i- Yeah... at, like, a Seed or Series A or even Series B company- Yeah...

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a lot of times you own-- you wear, like, so many hats, and effectively can end up, like, owning the finance hat because there is no head of finance or there is no controller in-house.

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And so you're overseeing all the stuff that has to get done at the, the company and that being one of them.

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And so we've, we've got several customers that are chief of staff, uh, chiefs of staff at different, different high growth companies. And so I think that, that's, like, been, like, one thread of, like, well, like, um...

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And we've, we've kind of introduced some, like, startup pricing and stuff too to, like, try to, like, be ideal for, for those folks. And so I think that's, like, th-that's part of it is just, like, pragmatically.

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It's like there's a time where it-- they can, can make great customers for, for Taxwire.But it's usually 'cause it's like, "Oh, hey, like we have to-- We're like growing really fast, and we don't wanna hire a finance person yet, but like we're-- should probably be collecting sales tax, and I don't know anything about taxes, and I have like no time."

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And so effectively, we can like take that off their plate, hopefully. But then, and then I think, I think I've actually come around to the existence of the chief of staff role more than I had.

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I, I, I used to be a bit of a hater, at least- You're skeptical.... pre-traction. Yeah. Yeah. Like I, I always felt, I felt like it was a very like not bullshit role, but like I, y- I felt like I...

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It was a role where I, I just, I felt like it... It's hard to put it exactly, but I, I felt like a lot of the people that wanted to do the role were like the wrong- Yeah... people to like d-do that thing.

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But, but if I should be hired- And you're not building, you're not selling, you're not- Yeah. You know, what, what, what are you doing? Yeah. But there is actually like, there's is a...

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Generally, people say build, sell, and I... That is true, and I-- but I, I think, and I actually would say a lot of chiefs of staff do actually sell. Yeah.

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Um, and so like that is like one common thing that people- And some build too. Yeah, totally. Build, sell. I think AI is making this even more interesting now because the- Yes...

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shit David on our team f-can do, for example, 'cause he is probably one of the most AI-native people in our team, he like did the first pass at like our...

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We were like looking at d-like expanding into international tax, and our head of tax was like very busy with another thing, and we were in the middle of hiring a full-time international tax person, but she wasn't gonna start yet, and he ended up doing the first pass at like getting everything going on like international tax research before like our tax team could focus on it.

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It was like, it was like, it was like pretty good. It was like our head of taxes was like, "That was like pretty good. That saved me a bunch of time." Right.

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And so like, and it's like he, it like he doesn't even know anything about tax before this.

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And so I think like great chiefs of staff at early stage companies, it's less about the like status that I think that role sometimes has, and it's more about you just do whatever it takes to win.

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And I think the chief of staff role is interesting 'cause you, it's very hybrid across... You're effectively like what...

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Besides building and selling, one thing that is valuable is giving leverage to the people that are building and selling, and great chiefs of staff do that for founders. They do that for the rest of the team.

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They will give like the team leverage to just do more of what they're doing, but do it with higher velocity and higher scale. And then, and then actually part of that is like building.

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Like, like David's like fixed a bunch of our rev op stuff because like I, I had like no time to do it.

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Um, and sometimes, sometimes I think like s- I know a bunch of great chiefs of staff that are like really, really great salespeople or, or BD people or whatever.

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And so I think it's like a really interesting role for like the generalist in startups.

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And, um, I think like, and I think the best, and I think David, David, who's like part of the Chief of Staff Network, and another reason why we're excited about this is he's had a great experience, is just like it's, uh, those, those people work super hard, and they, they eat like a, a lot of shit for the company.

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And it's, um... And those are like the warriors in startups that like help you win. Amazing. Well, um, excited to see you at Chief of Staff Connect. If you haven't gotten your- Send the beta...

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ticket yet, you should definitely get it. Um- Buyers market... talk to Andrew and, and David- Yes... and, uh, check out Tax Wire so you don't get, uh, you don't get the government gun af- coming after you.

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Yeah, yeah, yeah. Yeah. We will protect you from the government. That's good. That's good. All right. Well, thanks, Andrew. Appreciate it. Cool. Thank you for having me, sir. Yep. Bye.