536 Fireside: Accounting Firm Trends and 2026 Tech Predictions

Special treat for you today, my friends. I recently hosted just over 50 accounting firms out to an event in New York City. It's actually at Ramp's headquarters in the Flatiron district. Dinner, drinks, a lot of fun. But we also did like, a fireside chat. And the themes ended up being centered on kind of some of the biggest trends that I see today for tax and bookkeeping firms, but also where I think we're headed in 2026, both in terms of tech and also firm strategy, ended up being a fun conversation moderating this one. None other than Brad Gustafson. So Brad is the head of Ramp's accountant channel. He's been in this for a long time. He spent eight years at Xero before Ramp. Super sharp dude. Very in tune with the needs of accountants and accounting firms today. And I think it's what made this actually a fun discussion. We were on the fence, actually, about bringing a media team out for this one. In hindsight, I'm glad we did. Cause I think going to like this one. So without further ado, this was what we've been calling Firm Night Out, New York City edition.

All right. Good afternoon, everybody. Welcome to the New York rendition of Firm Night Out. Ready to get into it?

Can I. Can I thank everybody tremendously for being here? Everybody has a hundred reasons to not come out, especially in New York. Like, 200 reasons. But thank you very much for being here. Like, there's. We've done a few of these this week, and it's amazing, like, the serendipity of just getting folks in a room. I don't know if this is how it is just in any room for accounting firms or if it's like, the common thread of, like, you got here, you know, through the content or whatever, whatever. However you found this. But I've seen so many amazing things the last few days from, like, people that are on the fence of starting a firm and, like, finally committing and, like, other firm owners coming around that person and being like, oh, oh, no, no, no, no. We got plenty of work to send you. Like, if you want to start, like, we will help you start to, like, I just. Just, like, so many cool stories is coming out every single one of these nights. And I would just super encourage you, like, be the person to, like, make the awkward ask or, like, give me a number or shoot them a text tomorrow and, like, just recognize everybody's. That's weird for everybody, but that, like, this is such a cool crowd. Like, if you think about how people got here, like, just consider the context Everybody has that's here, here right now that you know your spouse is like, goodness sakes, you watching that again or listening to that guy's podcast again, like, it's very rare you're gonna be in a room of people that like, aren't annoyed by that. Right? So like it's, it's super unique. Like, recognize everybody has the, myself included has like the kind of uncomfortable side of that. But like, if you can kind of push through that, like there's, it's just, it's amazing the things I've seen this week. Week. But thank, thank you for being here and hopefully everybody makes a couple friends.

Awesome. All right, first question. These events that you're putting on and organizing, you're clearly very passionate about creating a strong sense of community with accounting firm owners and leaders. Would love to just have you explain kind of the why behind this. Like, what's the why behind running these events, getting these groups of people together.

Like, there was nothing more transformational for me in my own journey than meeting some people who like, just super understood what I did because they did the same things. And for whatever reason. And I grew up in Salem Morgan. That was where my firm was. We had a physical office there, for whatever reason. I didn't know a single other firm in that town. There are probably 30 or 40 firms in that town. I didn't know a single other one. There was like some people that you would bump into. There was this monthly CPE thing we'd go to, but the whole reason we went was because they had these twice baked potatoes that were super, super good. And you would bump into some of the same people and be like, oh yeah, hello. But I didn't have a relationship with a single one. Now I know like 10 firms that are in Salem from my content and I don't know why it is that way. I don't think most accountants are like inherently competitive or something. I just don't think anybody's creating the room for that to happen. Like, if you, if you think about like, I don't know that many people, but you consider where would you even meet them? Like for whatever reason, it just doesn't come up in the course of day to day stuff. But there's so many benefits to it from just like the support of getting to talk with other people and how it kind of just like recharges the soul when they can relate in a way that nobody else can relate to. Just very practical business reasons too, like being able to send work back and forth and, and all that. The content that I do, there's a, there's a certain like thinness to stuff online where everybody is shouting for your attention. And if I'm winning, it's because I'm better than brands or other people at shouting, at shouting for your attention too. And like, you gotta play the game and you gotta do the stupid YouTube thumbnail and you gotta package that thing and write that hook in a dumb way. And I don't know, I've personally, I've just been getting burned out on social media lately and it's just so refreshing and recharging to just like hang with people and talk and I don't know, do, do the human thing with people that just have a deep understanding of it.

Right.

So if I rewind time to 12 years ago when I first started working with accounting firms and I was at Xero accounting Software. Xero was pretty early in trying to foster community, host events, get accountants out to a happy hour to collaborate. It was a big part of my job. I was very early in my career. And back then there was definitely instances where I'd call up an accounting firm, you know, that I was partnered with and started say like, hey, we're hosting a happy hour in the area with a bunch of accountants, do you want to come out? Sometimes I'd get a response like, Brad, why would I want to do that? That's my competitor, I'm not going to do that. And so I'd have to like handle that and handle that. Objection. Curious. Like what, how would you respond to that? I know times have changed since 12 years ago, but how would you respond to someone who's like, ah, I'm not going to make time for that because that's my competitor and I'm not down to collaborate.

You know, there's an element of like self selection there where the people that opt out of that stuff, like, I don't know, I think they ultimately they're the ones to pay the price for that. As opposed to the people that will opt into an event like that. Who do you want to be in a room with? The people that are like, yeah, no, I can get it. Like it's pretty big pie. The entire world. And there's probably enough for both of us. In fact, there's probably opportunities to be leveraged by us being connected. There's, I'm sure there's still those people out there for sure. And I think the bigger you go in firms, the, the more of those people there are. It's part of why I like working with smaller firms is like, I just find the vast majority of people these days, and I would say the most closed off people are the ones that haven't experienced it at all and just don't know that many people. And they maybe default into the assumption that because they're in the same industry they ought to be competitive. But once you've had a few conversations and like had a few of those mutual relationships, like for me that I probably came up ingrained with the same expectation of no, like we're in the same town doing the same stuff, we shouldn't talk to each other. And it probably wasn't until I had a really cool experience with other folks that I don't know, it changed my mind. So maybe they just haven't had that experience yet.

Love it. Yeah, I'll definitely say the frequency of those types of conversations are now few and far between compared to what they used to be. So it is really cool to see how the accounting profession and accountants have become more open minded to collaborating and spending that time together. Another question I have for you, you run realize the community so you have a unique perspective and insight to what very large number of leading accounting professionals are talking about. I'd love to hear like some of the trends that you've picked up on. This could be common challenges in the profession, could be big opportunities in the profession, could just be themes that you're picking up on in realize these days.

Oh, themes. Yeah. So realize it's an online community and I think because the only place that's talked about it is in my content. That's a, it's a pretty progressive subset of firms and that's kind of my North Star for like my app recommendations and all that. Like what are the, what are the progressive firms saying and what do they love? Big trends right now for tax firms, scheduled work. So moving to a fully scheduled year where the expected time frame when the client brings you their work and when you do the work is all nailed down. And man, I mean I had a 40 person tax firm and boy, would that have been a foreign concept to, to me it's one of those things where you hear it and so like they're going to the level of every single tax return is scheduled like on the calendar and we plan the entire year's capacity like down to every single return. It's one of those things where you hear it for the first time and you're like, okay, like I don't. That's like I. That feels so far out of reach that reality is just not possible for me until you just start talking to a bunch of people that do it and swear by it and they're like, this changed my life. Like it's not until you can actually see that from real practitioners that you can almost even believe it. My CPA that does my stuff now didn't work an hour of overtime all year. And nobody I came up with in this profession like when they, they would have, I mean they would have heard that and just let that Teflon right off of them. Like they would have been like, there's something there we're not seeing or they're trying to sell me something or like it was, it would just be so incredibly foreign. Other really big thing in tax right now is tax workflow tools and the adoption of like this entirely new category of tech mainly around 1040. Intake automation is the most real aspect of all that tech right now. That's really, really powerful. Dan's in the room, right? Stanford. Who uses Stanford Tax here? The founders and the row behind you there. That's really exciting. Big trends on the, on the bookkeeping side, tech wise, I mean Keeper has been massive. Ben and Kenny are here somewhere. Who uses Keeper here? Yeah, we got some happy keepies. Where are Ben and Kenny? Oh my gosh. Are they not in the room right now? Holy cow. I was going to say something nice about them. On the bookkeeping side, I would say, I say Keeper's been a real big trend, just tech going more deeply into the ledger integration. Like you know, client hub's done some cool stuff with this financial sense done some cool stuff with this, but just more like deep ledger automation. And then I would probably say like, and I would say this even if we weren't here, banking and spend management, like just more bottom up, really good financial tooling rather than always having to bodge something new on and needing an app to do xyz just like the spend been happening in a more intelligent way being a big help to your workflows. Those are probably big things I call out.

So tax trends. We talked about, talked about bookkeeping trends, tech, anything in like CFO advisory style service space.

A lot of cool AI stuff around advisory. So what you do with your meeting transcripts and the way that's becoming a tremendous tool for doing advisory and training other people on your team and like you think about somebody, maybe think about a new person stepping into taking the monthly advisory call with a client and like having transcripts for the last 12 months of how those conversations have gone. I'm, I'm super geeked on the idea of how we're kind of coming into an. An age where knowledge automation is. Is possible for the first time because we have, you know, we think about my example. We have a chat assistant that can see into all of my podcast episodes, and you can have an interaction with that. And it's an incredible facsimile of the way that I talk about things and the advice that I give, like, it's shockingly good. And automation to date has been around what we do with data, how we get it from A to B and apply some sort of logic in the middle. But we've never really had any form of automation for our expertise, but now we have that, and we're still figuring out what to do with it. And it's not like. And I'm a great example. We've had this AI assistant trained on the podcast for years. Has anybody here ever used it? Have you ever interacted with this assistant that we have? Okay, we have one person. I'm going to meet a lot of y' all tonight and we'll have a conversation and it'll be super cool. But you've never gone off and had a conversation with this chat assistant. So we're almost still, like, working through kind of the human condition of it all is like, well, how much is it about what they're saying versus the interaction? Almost right? And there's situations where the. What they are saying is. Is really valuable on its own. And when we think about training our teams and a team member going through a situation where they're like, wow, what do I tell the client here? Being able to go to an assistant and be like, what are all the situations where people in my firm have had this conversation in the last year and see a bunch of examples, that's really powerful. I mean, when you go back to your early days in the profession, like those sleepy afternoons when you're just afraid to ask another question and you're stuck and you're spinning your wheels like juniors. Oh, my gosh, the resources they have available to them now with AI, especially for capturing a lot of organizational context and meetings and all of that, you could see where your career would have really been fast tracked. Have you had access to this stuff? Right. So that whole, like, that's a whole wild paradigm of how do we extend our expertise in an infinitely scalable way. It's not the real deal. It's not you. But it can also do things that you can't do where it can interact with any number of people. This almost like 80% version of you. Are there ways that, that we can use that to kind of work while we sleep and reach more people?

What would you say to a firm owner who is sitting there right now feeling overwhelmed by AI, knowing that this is something that they need to start thinking about and strategizing around, but they just, they just don't know where to start and they're kind of like have that paralysis by analysis where they're just in this place where it's like, what do I even do right now? Like, I'm hearing about AI everywhere. There's so many technologies to evaluate. I know this is important. What advice would you give that person right now?

How many people that listen to the podcast?

Yeah, these people can give this answer every bit as good as I can. It's like all things, you just gotta do it. And like the easiest on ramp to me is ChatGPT for business. It's almost like those tasks that hang out on your task list forever and they just haunt you for weeks. And then you do it and it takes like 20 minutes and you're like, oh, I probably should have done that a while ago. AI is kind of the same thing where it's like, just do it, man. Like, just start playing with it, watch a couple YouTube videos. The stuff is out there now. Like, there's content. There's no shortage of AI educators now, which is good. We need those people. But it's. I think there's a trap here because every other type of tech we've ever rolled out in our firm has been top down. Like, you go to a new practice management system and you, you get training and the whole team is trained on it and they know what every single button does and then you roll it out. But AI, like the magic of AI assistance is the open ended nature of it, the fact that it can be a very nuanced assistant for you and the specific thing that you're doing right now to do that thing in 10 minutes instead of 30 minutes. And there's no way to like universally train on that. Like, you can give people inspiration and give them ideas, but they just have to start and put it to work in ways that make sense for them. Like, I think you have to, you have to force a feedback loop here. And my take here is we need to be meeting with our teams every single week for say 30 minutes just to be like, what'd you try this week? What worked and what didn't work. The more of those touch points you have with other people, you get to see what, what they're doing and what they're trying, you'll get some new ideas from that. But it like the whole like we're going to make this big massive mega plan and invest X number of dollars and all, like it misses the point. In fact, I was at a dinner with the CFO of a very big like company. Everyone in the room would know their names. And we Talked for like 90 seconds and he's like, can I have you come in and do some work with our finance team to, to figure out how to use AI? And I'm like, what AI assistance does your team have access to right now? And he said they don't have access to anything. And I'm like immikal when like they have actually been able to use an AI assistant. And this is, we're so far down the road and this is a very cool like progressive company. Just got to do it. Like she's got to get in people's hands. Some folks will take to it really fast, other people won't. But there's no replacement for just doing it.

So like tying all that in a bone tactic and I'm going to press you on this like tactical next step that a firm owner can take. Is it creating a feedback loop and like encouraging their staff to explore new uses of AI and be reporting back on that? Is that like the tactical next step?

Yes, I think, I think you set a standing meeting every single week. You get chat GPT for business in people's hands. You send them two of my videos, they watch it for 30 minutes and say let's meet every Thursday and just share what's working and what's not working.

Shifting gears a little bit. We just got past the tax deadline. We're going into year end. Where should accounting firm owners be spending their time right now? Like what should they be prioritizing over the next 2 and a half ish months?

There's so much stuff to do. It sucks, man. How many people here do tax? Bless your hearts. Cause you want a break so bad. And the last thing that you want to hear is your next 12 months is kind of made up by how you spend the next two months when you want to be like on holiday and all that tech. Gotta lock down the tech stuff for next year. Please use tech that's already been proven, not tech that's being released over the next three months. So a lot of folks that will sit on their hands for years because this thing is coming or this feature from another tool they use is coming when there's a tool on the shelf that already does that job very well. We got to get through that as fast as we can. That is where peers can be tremendously helpful. The whole tech FOMO and not knowing if you're on the right thing. The only solution to that that I have found is being able to ask your peers who use that stuff. It's the only way to cut through the BS of what works and what doesn't work. And it's why my recommendations are 100% based on what do people tell me that they love? And sometimes like founder types will be like, oh, we've got this feature and that feature and that feature. And I'm like, I kind of don't care about your features. I care about are firms raving fans of what you do and is it actually working for them? And you're going to, you're going to deal with this every step of the way. Even if you had the luxury of throwing out your whole tech stack and going to the tech stack that you think is perfect today, and you roll that out six months from now, you're going to see something new and you're going to be like, is that better than what I'm using now? And the only solution I found for that is having people that you can ask. And that's the value of stuff like this and why I'm so passionate about community and like get somebody's number where it's like the guy that raised his hand and says he uses Stanford and you'd be like, oh man, I could ask him if that makes sense for me. Like that's, that's, I think, how you cut through the BS and all the marketing and all that stuff. The other huge one, which everybody that listens to the podcast knows is, is renewals. And on the flight out here, I was responding to text messages and several people had sent me like example proposals. They were like, can you give me feedback on this proposal and how we do it? And I'm a believer that there are so many small things we can do to squeak more money out of every single engagement. I mean, the big one being three tier proposals. Like you've heard me rail on about a lot. What shocks me still about the accounting firm ecosystem at large is still the majority of firms don't do a formal annual renewal. Like they don't send any sort of proposal or anything like that to a client. The assumption is that they will be forever clients and at some point they'll just give an engagement letter, something from the insurance carrier, right? And that's how my firm used to be back then. We did hourly billing after the fact and there was no renewal. Like they were just on the list indefinitely. And maybe we got an engagement letter signed, maybe we didn't. But the power of being able to put a proposal in front of somebody up front is to give them those three options and let them self select into whatever option they identify as. And so one of the interactions I had earlier today, Gal had a kind of a three tier proposal. And I think the tiers were called like basic, standard, and something else. And I'm like, let's change the bronze package to minimum. Let's call it minimum. Let's call it something that hurts to click on because nobody wants. And this is the power of three tier proposals, especially the first year you roll them out is whatever they've been on in the pat in the past needs to be the bottom tier. And it hurts to opt into the minimum. And you can definitely do more for them. And that can be a trap too. Like, you don't want to, you don't want to, like stack up those bigger tiers to be too much. Then you got a problem on your hands trying to fulfill all that stuff. But the whole three tier proposal thing is unbelievable, unbelievably real. There's been a guy, he actually used to be my accountant back in Oregon. When I first sold my practice, he was rolling out three tier proposals for the first time. And it keeps messaging me. The first one was like, just got my first silver. The first 12 were all bronze, but just got my first silver. And the other day he's like, I just got a gold. He's all right, I got another gold. And everyone, he's. He set this up so that everyone's prior year's fees were basically bronze with like a bump. And he's doing this the right way, in my opinion, where the higher tiers are not a ton more scope, they're just more premium delivery. They are like faster access to him and like, it feels more premium. His gold is 2.8x his bronze and his silver is 1.8. Every gold that he takes on, he can effectively cut six bronzes if he wanted to. And there's so many examples of this in the wild that we encounter every single day that impact our buying decisions. From the brands we buy to the type of airplane ticket you get where you make the buying decision based on, like, what you identify as. Am I a premium buyer or not? Like, am I going to wear the cool brand name thing or not so the optimized way to run your accounting firm can never be give them a price. Give them one price, right? Just think how much money we're leaving on the table.

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Let's go off script a little bit. So I jotted down some questions and I checked with Jason like 10 minutes before we got on stage. Can I ask you some personal questions to get to know the Jason behind the Jason?

The Jason behind the Jason. Yeah.

So here they are, Random assortment, unprepared. Your bucket list. Travel, destination.

Ooh. I've got too many young kids right now for this to even take up any part of my mind to even think where I would go. I can tell you what, I went to Sydney, Australia a couple years ago and Bondi beach and just the whole Sydney vibe. Like, big clean city, like SoCal beaches everywhere you look, but with way fewer people, less needles in the sand, a lot more sharks, but probably Sydney. Like, if I go spend a month in Sydney right now, that'd be pretty great.

Okay, your most embarrassing memory.

Embarrassing memory? Yeah. Oh, geez. I had to give a speech in a class in high school. I think it was my junior year. And I knew every single person in the room. Like I'd known them for years. And it was just something where you had to get up in front of the class and do this thing. There's maybe 20, 25 people in the room. And I got so nervous that my voice was like uncontrollably shaky. I was like, like talking like this, like to the level where everybody, like, it's not like you can hide it. And it was this weird thing where like I. There was nothing that I could do. And I'm like a minute into this and I'm like, is the teacher gonna bail me out or like, is this just gonna happen? And I had to plow through like a full, like 10 minute presentation staring into, into the faces of all of these people that I've known for a very long time. And everybody knows I'm having like a full on meltdown and went through the whole thing, totally humiliating, and it ended. Nobody ever said a thing about it, but it was very obvious that I was like losing my crap up on stage. And every time I go and spend. Not every time I go and speak now, but like, I will think about that. Like, man, that was the same person like, that was me. Like, is that gonna happen this time? But I don't know. Like, even. And maybe that's helpful to hear that. Like, you know, we all have a version of this, and we kind of pretend that we don't. We find our own ways to cope.

I feel like you can go in one of two directions after that. You can either be afraid to speak ever again, and you never get on stage, you never speak, or you're like, okay, worst case scenario just happened. So now I'm more comfortable speaking.

Yeah.

So pretty cool you took that route.

Yeah.

Favorite television show or movie that has a main character or character that is an accountant.

Oh, God. Accountants portrayal in media is awful. Awful. Like, you'll be watching a show just trying to relax, and you'll catch a stray when there'll be some character where they're like, yeah, he's an accountant. And you're like, does it have to be that guy? I don't know that there. The whole, like, you know, the accountant movie, like, it's so extreme that it's. It's not relatable. I don't know. What would you say to that?

Maybe there's no good answer. Maybe that's an opportunity for Hollywood to make a new movie that has an accountant that's more relatable.

Who's got a good answer to that? I think it's cool that, like, hip hop stars reference accountants a lot like Lil Wayne would be like, an accountant handles that a big, small. Yeah, yeah. I'm from the Bronx, so whatever. Okay. I like it. Yeah.

Who's the accountant from Parks and Rec? Yeah, the Gotham. Parks and Rec. The main character in Severance just now. Oh, Adam Scott. Yeah, yeah, yeah. I don't know what his character is called. He was great. And he had the board game that he made. What was that called? He would. That was pretty great. Okay. Parks and Rec. For people who have seen Parks and Rec, one of my favorite scenes in TV ever, when he goes to this accounting firm and there's, like, the owner of the accounting firm, and he just thinks he's hilarious and does just the ugliest laugh at everything he does where he's, like, snorting and it's like everything you don't want accountants to be portrayed as. Right. But Adam Scott's character is, like, this cool accountant, and he's, like, incredibly impressed with him. I can see, like, three or four people that are like, yeah, I've seen that scene. It's good.

All right. On a slightly more serious note, where would you Say you get your strongest sense of purpose or fulfillment in what you do. Where does that come from?

Events. Events. Events are terrible for my business. So really hard thing about being a visible personality and this is all gonna sound very privileged, but like content creators, it's very rare you will see anybody make YouTube videos for five years even, let alone five years. Like, it is like, you think of like professional athletes. Like, you go into that and you know you're gonna have a very, very like, short run. It's just not a sustainable thing. It's an awful business in many ways because if everything is just built around this one person and in all likelihood they're gonna burn out in five years. Like, that's, that's a real short term business. So we, we are, we're very mindful of like, what are the things I'm enjoying and not enjoying. And last year I did some events and it was so energizing. Like, I came back from that stuff and I'm, I'm. Believe it or not, I'm very much an introvert, but I came back from some events, meeting a bunch of folks that, that consume the content and just had a bunch of conversations. They told me their stories of, you know, what, what they're doing and what they're working on. And I was like, we got to find a way to do more of this because it's kind of what's keeping me alive. Like, my reality is spending a lot of hours staring into a camera. The day before I flew out for this week's events, I was in front of camera six and a half hours in one day. And the nature of doing content online is not unlike managing your clients, where the people that take up all your headspace are the squeaky wheels, the people that complain. And so every day you're visible online, you, you got people saying all sorts of crap about you. And if that's all you do, like, I can 100% see how that is soul sucking. And it's just missing part of the human experience where you just need to have real interactions with people. So this stuff is far and away my favorite. We're still figuring out how to actually make it a business and not just throw away a bunch of money. But this is incredibly fulfilling for me because I can hear y' all's stories, but I can also host an event and, and it's like we're able to bring people out, but then the energy and the excitement is what y' all are doing with each other and having the interactions and the cool people you're meeting and the connections that you're making and all of that. And that has absolutely nothing to do with me. But I feel like I'm almost, I almost feel a sense of duty to like enable that stuff. Stuff because so many cool things come from it. And in a world where like the whole online, social media and all that stuff just feels thin as ever, it's. I love it because it's the other end of the spectrum. It's like as, as deep and meaningful as something can be, I think.

And you have some new workshops coming up, right? Could you, could you share a little bit more about those workshops and what people can expect?

Yes. I'm terrified. It's the scariest thing I've done. It's the first time I've been like, so, so scared. Like need a gummy every night to sleep scared. And probably two years. So we will have 14 of these between now and the end of the year. We're doing one in the city here in December. They're half day events, so half day workshop, we're calling them Jason on Firms Live. And that's kind of the idea is it's kind of the live in person experience. And those events end with like a live podcast recording. Every city has a special guest, a surprise guest that are going to be really, really good. But then it is, it's a full afternoon that is CPE eligible. And I'm. The way we're designing these events is there will be programming from me for sure, but it'll also be facilitated stuff where you have an abundance of time to like work through stuff with each other because oftentimes, you know, everybody's having a great time out there and you're like, everybody stop having a great time and come in here and listen to me. Accounting conferences are so much this way, right? Where it's, it's so slide deck after slide deck after slide deck. And a big part of that is actually because of the, how restrictive CPE is and the format that CPE has to be in. And it has to be 50 uninterrupted minutes. And there's so many accountants who will only go to a thing if they get CPE for it. Drives me nuts. And so these events, there is no av, there's no slide decks, there's nothing. It's programming for me. It is structured facilitation with the people in the room. It is a rad surprise guess. And then it is a podcast recording. And then after that the whole thing rolls into a dinner where at that Point, the vibes are off the charts. And then you get to go to dinner and you, like, lock all that stuff in with a whole bunch of new local people. Because in my opinion, the problem with big accounting conferences today is leaders go out to conferences and they get all pumped full of inspiration. They're all excited and they're like, oh, my gosh, so many good ideas. And they go back to the office and they're like, gang, this, this, this, this, this, this. And they're like, can you just. Can you go respond to the emails that we sent you when you were gone? And they're like, just give him a week. Give him a week. He does this every single time. Everyone go back to normal. Give it a week. Next year goes to the same conference, exact same thing, all pumped. Comes back, you got all the good ideas in the world. If anything, it just makes you more frustrated with your inability to realize your new vision, which is now more ambitious because you've been inspired. Right? So what are you ultimately blocked by at the end of the day? Your team? Change management. So how do we inspire the team if that's what you're blocked by? Because wouldn't it be great if you were surrounded by change agents who were pumped to do that thing to the degree that it just happened because you didn't have to force it, because they're just as excited as you? Right. So how do we make that happen? Well, you're not going to fly your entire team out to Vegas. I started taking my team members out to conferences, and it was still reserved to kind of just a few leadership, and it was really expensive. The only way I figured out how to solve for this is you run a whole bunch of local events and you make them cheap so you can bring your whole team out to it. Because I think the best gift that I can give a firm leader is not to inspire. Inspire you one more time, to inspire your team so you can finally actually do it right. You have people around you that have finally escaped kind of the group. Think of your accounting firm and they see something cooler and bigger and they're like, okay, like, I might actually be excited about my job and what I do for the first time in a while. And when you're surrounded by people that'll buy into that and, like, finally have a shared vision, man, like, that's really exciting. So that's the whole idea behind these workshops. Why they're only a half day. We could justify only losing a half day of billable hours, but to get the whole team out you have a really cool experience. You go have a dinner and have like the coolest night of the year with your team and then hopefully when you go back to work the next day, like you got everybody at a different energy level. Can you tell I'm excited about it?

I can. I'm just still thinking about your comments on CPE credits and how restrictive they are. I remember being right here where the audience is last year brainstorming with my team, like, how can we deliver more value to accounting firms? How can we make CPE credits and getting CPE credits like a more enjoyable experience than it is and not just be dev by slide decks? Still working on it. But we have Ramp Academy and I encourage you to get into it, get some CPE credits, learn about Ramp. That's my only plug for tonight.

Cool.

Well, I have one more question for you and then I'd love to set it up for Q and A from the audience. Final question for you is thinking into the future. 2050. So about 25 years from now, what does the accounting profession look like? Would love for you to just start riffing, like what do you think it looks like in 25 years, 2050.

I don't know what it looks like two years from now. There's a really old video that we did that was like all these different possible timelines. And there was one timeline where the world is like just, everybody just hangs out, lounges around all day, like, everything's good, everything's cool. Except for the accountants. The accountants are the only ones that are still working and they're all like, we told you so. We told you AI could never replace us. We told you we were irreplaceable. And everybody else is having a great time. They're poolside, are playing a lot of pickleball. But the accountants are still like working, you know, 55 hour weeks. I hope I have young kids, you know, I hope with all this AI conversation and the, and the fear and the US versus AI of it all, I hope there's a timeline where like it could just be better and people could maybe just work a little bit less and AI could actually lead to a better, a better world and a less work obsessed culture. The best thing I ever did for, for my business was have, have my daughter. That was a very universe realigning, sort of forcing function. And my personality is so geared around, I need to be spending my time in high leverage ways. And this could be, this is a video. We need to put as many people as possible, can see it and benefit and all that and you get so sucked into that stuff. And I go downstairs and my, my six year old boy is like stuck on a Lego build and he's like, hey, can you help me with this? I'm like, that's such a low leverage task and it sucks. I don't want, I don't want to be, you know, wired that way. So I hopefully, hopefully some part of this journey gets us to a better place. And there's, you know, always this conversation of what's on the other side of something that does automate all this work. And it's like, man, hopefully it's more of this, right? Like I was on a flight to, to Miami last year and I get on the airplane and very quickly realized something's wrong. I think I told you this story, didn't I? At scaling, I very quickly realized something's wrong. Turns out there's a Taylor Swift concert in Miami that night and it's just a plane full of 11 year old Swifties. Like they're playing it over the intercom like, like surely the FAA would not allow for this flying to Miami to consume Taylor Swift music. That's the least efficient way you could possibly consume Taylor Swift music, right? Like less than 10 seconds, Brad could be blasting that out of his phone. Why in the world would you fly to Miami to listen to Taylor Swift? I, like, I don't know. Why does nobody want to talk with my AI chat assistant? I don't know. But the same people that won't talk with it will come here and inconvenience themselves on a night when they could do so many other things. And I love this stuff. So, like, hopefully on the other side of not having the key W2s into my tax software or do whatever, you know, inane document management we do to close a set of books, hopefully on the other side of that is just more of this stuff. Even introverts, like, we're not extroverts, like most of us don't pride ourselves on going out and doing all this stuff. But here we are, we're having a good time because we found people that are, they're kind of. We have kind of a common thread in what we do that makes us get into a room and the vibes just kind of happen. So hopefully there's more space for that and whatever changes in the next few decades. Love it.

I'm optimistic too.

Funny thing happened recently when I was at a conference with one of this episode's sponsors, Maker's Hub. So Makers Hub, they're like An AI accounts payable platform. The party trick is they're using like AI vision models to do extraction at a level that was kind of never before possible with OCR technology. But I was doing something at their booth. Some of their customers came by like it is one of those tools where the customers are kind of raving fans. But a funny thing kept happening. Like people kept throwing out these ridiculous document situations they have where they're like, I got this client, I have X, Y and Z problem. It's a total mess. We spend so much time on it and they just start riffing on it, like with the Makers Hub team and they're like, oh yeah, no, I can see like you can do this potentially. Like our product doesn't really do that. But actually if we change this or that, this could potentially work. The team is just like, they're just a bunch of like document processing geeks who are also AI nerds. And the product very much is like the marriage of those two things. And so what Maker Sub does best right now? Like the biggest, ugliest accounts payable stuff that you got, man, I had some gnarly clients where Makers Hub would have saved us so much time. If you're out doing conferences at all, you'll see Makers Hub a lot add into a connect. I'm going to be there. I think. I'm actually co hosting a thing with Maker's Hub. But if you got any ugly bill pay stuff, class tracking projects, inventory, manufacturing, stuff like that, definitely worth giving Makers Hub a look. To learn more, check out the link down in the show notes. Hey, real quick. I write a weekly newsletter, goes out every single Thursday and let me tell you, it is a banger. You ever struggle to keep up with like a high news updates? Things are happening so fast, Jason. Where do I learn more? What is the most up to date tippy, top hot goss in the industry and tech advice and all that? It's the newsletter, buddy. Straight to your inbox Every single Thursday, 2pm Eastern. Thousands and thousands and thousands of thousands of accountants read it. I'll put a link to it down in the show notes. If you aren't on that list yet, you better get on it.

All right, Q and A from the audience. Do we have a microphone that we could pass around? Who has questions for Jason.

First?

How would you cultivate a team that's resistant to AI, like using ChatGPT to elevate their workflow in a sense? Like what are some strategies that you would recommend? Yeah, I mean just from a real practical Standpoint, that standing weekly meeting to me feels like a minimum. I think it ought to be a factor in how we hire. So the same way we're looking for aptitude and skills, I think we need to at least make sure that there's an openness to change. And learning new stuff like that's kind of the scary thing right now is just how fast change is happening. So being mindful of it with new people, you bring in having forcing functions to make sure everybody is using it. Like, when I realized that video was a great hack, I had several recurring tasks I had to do every single week. And I told myself I have to do it on video. So at a very minimum, I was making like three videos a week for this kind of internal thing, a low stakes way. So you kind of have to like build that structure in somehow to make sure people are learning. But third, I would just say, like a lot of people, a lot of accountants need to be inspired. And that's a really hard thing to do. They're tough folks to get excited about things sometimes. But that inspiration doesn't always need to come from you. In fact, oftentimes a lot easier if it comes from somebody else. Like, how many times have you sent a video of mine to somebody where it's like, let him tell you instead of me? Right. I think it's really beneficial to get the people on your team thinking, not like staff, but like entrepreneurs, like get them outside of your internal kind of group think. And that's a big push in the workshop is like, what does it look like to support the business owner and to think bigger picture about, like, what are we all trying to do here? So hopefully kind of you're, you're a window into like an expanded worldview and kind of opening a window to a cool version of the future. Because I think the more you actually roll your sleeves up and use the AI stuff, the less scary it is.

And sir, what was your name? Eric. Thank you, Eric, for the question. Who else has a question? Hi, my name is Sam. Jason.

I found your content because I'm getting.

More involved in running my 30 person firm.

And that's like a lot of the.

Stuff you talk about that's not the tech and AI. And you talk a lot about this legacy firm that you worked at and bought and now you don't work there. So I'm just wondering what happened to that firm? How did you get out? Where are they now? See, this has always been a question in my mind.

Yeah, that's a great question. When it was kind of the final decision that I would be leaving. It was a few months before year end, and we, like, we had to do it quick. It was like it was going to happen, and I didn't want it to string on, string on for a year or something like that. I think beyond a certain time horizon, hard stuff like that. If you say we're going to do that 12 months from now, it doesn't actually happen until a month before it happens. And so I'm like, we just need. We know we're going to do this. Let's do it. It was me and partner. Me and my partner were very different, complementary in many ways, but the business was going to be very different without me. At that point. I would go to Twitter when I needed to hire somebody. I said, I'm hiring somebody, and I would get DMs and we'd hire somebody off Twitter. And that doesn't work when I'm not in the picture anymore. So when we announced that I was leaving, there were clients that left their staff that left. There was like, the reality was we just had to get to a version of that firm that worked for my partner. So I make no bones about me having a successful or glorious exit or anything like that. Like, my circumstances. The way I see my circumstances in that situation was I had an amazing new opportunity that had somehow become a business that I could follow this. And I've. I was helping more people than I could have ever helped in a service business in my accounting firm. And the people that I felt still a tremendous amount of responsibility to were like. I mean, some of the people that came to work for me were like the super fans, like, they were the OGs, like, the most hardcore people that were bought into my vision and they wanted to come and work with me. And those were the people I was leaving. So consideration number one for me was like, how do I not leave the firm in a lurch? Like, this was not like a. Like, Jason's cash now did this big, cool, impressive, successful thing. It was not that at all. It was, how do we make sure that they're in a place where they can continue forward with my partner and his vision for what that firm would be. And so that.

That.

That was ultimately what it was. The firm changed definitely because I had a big influence on the types of folks that we brought in and all that. But hopefully, in the end, like, they were kind of on a path to being a very different firm. But the firm that was designed around his personality and the type of firm he was excited to run. That's kind of the, like, it's. I talk about, like, an influencer business. Being a content creator. Like, running a small firm is not too dissimilar where the. What that firm looks like is very much a reflection of you. And there's goods and bads to that, but it means that you can build it around the stuff that you're excited about and, like, the stuff that you're. You're pumped to solve. But then the downside of that is. Yeah, when the owner changes, when there's. There's turnover there, then that's. You're kind of. It's a bit of a rug pull on the system. If it was built around, you did that adequately answer the question. Yeah. Okay. Because that's. You never say, like, how you left or what happened. It's just that you bought it, you.

Ran it, and then now you're doing this.

Yeah, I sold it back. I mean, I effectively gave it back to my partner. I sold it because I had a big old note that I was paying off. But, yeah, I basically gave it back to my partner to try to leave them in a place like, I didn't there. That was not a good feeling doing that. Like, it was very, very hard to go away from that situation. Honestly, part of why I don't talk about is probably, like, there's probably some guilt there. Like, I don't have any. I don't have any regrets. And I think I handled it just tactically, trying to do right by people as best as I could, but still a very hard thing. And I don't know about you, like, there's. There's people that know me from this stuff. There's people that know me from real life. There's real life people that will stumble into my YouTube videos and they're like, I don't know who that person is because we're all kind of playing a character when we're in those different contexts. Right. And. And anytime sometimes I'll get an Internet comment from a person that I used to work with, and it's like you get this, like. I don't know, this, like, shot of adrenaline, of, like, it's kind of like different things crossing over. So. Yeah, I know. It's kind of odd.

Great question. Who else here?

You talked about being an introvert. Can you speak of what are the biggest challenges that you faced of being an introvert and then being on camera all the time? Yeah, that's a good question. I actually think there's something about being on camera. That, at least for me, was not as problematic as being visible in person. In fact, I think there's some introverted people where they can. They feel like they can actually be more of themselves and private in front of a camera. And I've probably got a degree of that. So at least in my experience, I can say I don't know that those two things totally cross over where, like shyness or discomfort in social. Social situations. I don't know that you'll always ultimately feel the same thing in front of camera. In fact, in some ways, it can kind of be an escape. It's almost like you're able to be the person you wish you could be in front of other people. I heard some other creator frame this really nicely. I heard it recently just that having an audience and going to events like this is a really great, like, short circuit for social anxiety because most people, they already know something about you, and it kind of bridges through that initial awkwardness. It's still awkward. And I always tell people at events, like. Cause it's like we had an event in Chicago last night, and there's so many people that came and left, I never even talked with them. And it's super frustrating to me, but it's awkward to come up to me. And like, I tell people it's just as awkward for me like it really is. But it's just like any other social situation where you're having an interaction, something awkward happens and you feel it 100% yourself, and you're like, oh, I'm awkward when they're feeling the exact same thing. And it's like, that's just how everybody is. So I don't know. I don't know if other folks who are introverted have maybe had a hard time getting on camera. There's also a whole other skill set of your comfort level with being visible online and how resilient you can be to the things that people will say and how you're just inevitably a target when you're visible like that. And that's not just an online thing. That's. That's speaking. That's all sorts of things. I mean, I've. I have the perspective of a. A white man, which is not going to be everybody else's experience when it comes to this. But if you can find a way to compartmentalize the problematic aspects of that and kind of build a thicker skin, which I've definitely, over the years, I've gotten better at not letting that stuff bother me. It's such a hack because there is no serendipity machine. There has never been a serendipity machine like we have today. Being able to put stuff out online and be visible and make all these connections that you never could have otherwise, like, willed into existence yourself is so, so powerful. It's such a hack. But you've got to manage those things of, like, people are going to try to tear you down. It just like in any sort of success, people will try to try to tear you down. So I don't know, there's almost, I think there's almost for me, an element of that introvertedness that was kind of liberated a little bit in the content because it was a way to make those silly ideas come to life in a way that personally distanced me from, like, the execution of that. Like, I could not jump up on stage and do the silly things we do on video. That would be so uncomfortable. So in some ways, it almost kind of sidestepped that introvertedness.

I have something to share too. I know the question wasn't for me, but as an introvert who has spent their career needing to network with people, be on stage, present. I really like your question, and I have a response that may be helpful for someone in here. Like, what I've been able to realize over the years is what makes me most uncomfortable in these social settings with people is small talk. Specifically. Like, what I've realized is when I can connect with someone on, like, a deeper level and talk about something exciting and real and authentic, I'm an extrovert. All of a sudden, I'm like, okay, I'm an extrovert. Like, let's go. I have this energy. But if it's just kind of like the small talk and just like this social etiquette, I get uncomfortable and I actually, like, avoid it. Like, I don't know if you guys saw me earlier, but I was kind of, like, running around. So I'm like, small talk, small talk. Like, I'm not comfortable with this, but, like, if. If it's a conversation where I can actually, like, deeply engage with someone, like, a different side of me comes out and it's more exhilarating.

I don't.

I don't know if anyone else feels. Feels that way, but it's definitely true for me.

That's the fun of this stuff is I think it compresses the small talk. It's quicker to get through and then you get to the thing you're both into and then you can just geek and an hour goes by, right? It's like When I go to something, when I go to one of my kids things and you're just desperately trying to find that thing that you can connect on that may never come. That's brutal. But here it's like, it's so easy. It's like, tell me about what you do and before you know it, you're off to races.

Other questions in the back.

So this is maybe a little bit of an immature question for some of the folks in the room that are running more mature firms. But you kind of teased recently, if you were to start a firm now, kind of like, what, what should you do? Should you buy a firm or whatever? So as an imposter syndrome, big four, moonlighting on my own firm, that's very small. What would you do? What are your top concerns? If you were to start a firm top tomorrow and start working on that and maybe leak a little bit if you are actually in a follow through, you know, the big blocker I have there is like the purpose of doing it would be to show and document it so people can kind of see that journey. The problem is if you start thinking about that in practice, I think it very quickly breaks down and people are like, well, I don't have all those advantages that Jason has and so I could never actually do that. My answer would be like finding a very nuanced, expensive pain that we can just go really hard on. And that probably starts with just going to loads of trade shows and talking with a lot of people. And even that documenting all that I think would be fascinating because you can see like the work that goes into finding those things. And I think it's really hard for a lot of us to get out from behind the desk and think about those bigger kind of business positioning things where it's like we can. The easiest thing to do sometimes is work another 12 hour day and run smack into the same wall again and again and again and again. And if you're not careful, you'll convince yourself that you're doing your best. When the harder thing to do is to stop and be like, oh, should I actually be doing this over here? And this fundamentally different thing. So that the part of that that I may be most excited about is, would be documenting going out and like even just trying to discover like what's the thing that I'm into, where I can find somebody that will pay me really well to do this thing. And then how do you build the marketing around that and show up and get a software vendor to give you a free ticket to go to that trade show and stand at their booth for a couple hours and make friends with them and then let them get them to let you write a blog post and put you in front of a bunch of people in that niche. Like, just that whole arc, I think, would be really fun. Fun. That's. That may not be the answer for everybody. I had an event in Chicago last night, and there's a guy who's like, I was telling people this a little earlier. He was like, I want to start my own firm. I'm thinking, hopefully by, like, after next April, I'll be able to do it. And There were probably 35 firms there, and this was early in the night. Throughout the night, he's meeting other firms that are more mature firms, and they've got all sorts of work. Work that they don't want. A bunch of clients right now that they're like, I love these people, but they're not a great fit for me anymore. What do I do with them? There was enough work in that room for that guy to be 10x over capacity. So I actually think the right answer for a lot of people is, you're in a room full of a whole bunch of accounting firms, Some who are just about to get going, others who have been going for a while, and they're like, how do I get rid of the clients that I had earlier days that are no longer a fit for me? Me. For a lot of people, I think that answer is like, building a network where you can be useful to someone. A tax firm that just wants to do tax, but would love to have a bookkeeper that could send all their work to. Right. Vice versa. A bookkeeper who just wants to work with veterinarians and they're trying to find more of them. Working with a tax pro that works with veterinarians. That might be an easier way in for a lot of folks who are like, I'm not a marketer. I can't do X ray. I would say, like, you still got to push back against that. But a lot can be solved with network for, you know, stuff like this. Finding other local people and building your starting client list, which will never be your forever client list. We talked about how you're getting into tattoo. Tattoo. Did you call them tattooists? Is that what they're called? Tattooers. Okay, sorry, Tattooers. I think everybody has this vision of, like, what's the perfect thing that we want to build? But when you're in the. When you're starting out, you're like, I just want to be building my Own thing and not somebody else's thing. And so you do whatever is going to get you started. And I think that might be the easiest way for a lot of folks is through network.

All right, I know we're coming up on time, we might be out of time, but one more question. Anybody have one more here?

My name is Betty, I'm from San Diego actually.

The heck are you doing here?

Just fly out from yesterday after taxi season.

Just enjoy, just hang out in New York City.

Yes.

Awesome. Great. Everybody here is like, can we go back with you?

Yes, yes, absolutely. It's beautiful weather, running that small boutique farm and obviously going back to the AI and obviously great idea. We are using AI and you know, mostly our staff using chat GPTs or something along the way looks like obviously responses and everything from the client or we're providing looks like AI generated which sometimes concern for us and concern for the client and especially the boutique firms we're using people wants to be a high touch like the way they engaging us. So you guys, how do you guys feel about providing those answers or analysis that look like generated AI? Do you guys lower fees or how do you market yourself? Do you still consider yourself as high touch or do you actually wanted to go in a direction that where we're providing really good services but automated or quick. But because of that we're lowering services fees to attract more clients. It's kind of away from how we have been, you know, operating at a firm as a high touch. So I just wanted to see your perspective. How do you guys feel about and as of course is your feel your answer as well.

So yeah, my take is clients don't want to see AI generated stuff like for the same reason that y' all won't interact with my AI chat assistant. In fact, sometimes I'll get stuff from my team where they put a bunch of useful information into it. But it's very clearly a chat GPT formatted doc that's like three or four pages. I'm like, I'm not going to read this man. Like I don't like. I just have this, I have this reaction to it where I'm like this is. It's like irritating. There's cool uses of AI where that can be deployed where there was not previously humanity in the human touch. I think that's cool. But to replace something that was delivered personally is a big time risk. I think.

Even if the AI gets really good at doing the work in a way that it's not capable of right now, but say it gets really, really powerful. Like there is still, there is so much value and just the connection that honestly has gotten pushed away in many ways because we're so busy with the doing of the work. I personally, I struggle with the idea that there's going to be this like deflation in the value of what we do. It ultimately depends on what you're in the business of doing. And that's actually really important is to think about what is it that we do. Because if you go to most people's websites, you'll see a list of services and there's a world where AI can do all of those services. But that's not really what most people do. Like it's like I tell bookkeepers, like my hot take on bookkeeping is bookkeeping has already been largely automated and everybody talks about like, oh yeah, it's going to replace bookkeepers. I think bookkeeping has already been largely automatic. Bookkeeping was entry of transactions and classification and we don't do entry anymore. And the vast majority of classifications, automated bookkeepers are really like controllers. And so it's the narrative of what we're in the business of selling becomes more important. Because if we sell filling out your tax return and you know, AI agent can go and fill out a tax return which are kind of already there, then if that's what they think you do, if they think that's the value you're providing, then yeah, they're probably going to look somewhere else. But that's not what we do. Like even, even if we're struggling to still find that language, what the client gets excited about is the opportunities that, the things that they can do because you've taken that work off of your plate and when you have that conversation that, that new idea where for the first time maybe they're able to come to a more data driven version of a decision, be it hiring the next person buying a machine, something like that. So all of that is to say, I do think it makes it very important for us now to be very intentional about how we communicate what it is we're delivering. Are we selling the trip or are we selling the vacation? Right. I think right now if you look at a lot of firms messaging, it is very detailed. Like if you look at a proposal and it's like this includes X number of transactions a month and X number of bank statements and all the minutiae of what you're doing, then you're kind of, you're kind of selling like the thing itself rather than the experience and the opportunities associated with you taking that work off of your plate. That said you could do a whole, I mean you could do like a whole day on everything you just outlined there. There's a lot, there's a lot there.

To add to that. I think a helpful framework to think through. And this is coming from a place of I'm not an accountant, but I lead an accounting channel that works with accountants. The people on my team are managing 100 plus accounting firms as partners in a, in a similar way that an accountant would be managing clients.

Right?

They're consulting, they're meeting with these firms. And when I think about AI, I kind of use the framework that you mentioned earlier, like thinking about high leverage task versus low leverage task. Human interaction, in my opinion is a very high leverage task. It's very special. It's getting increasingly valuable as the world around us automates. And so the more we can preserve human interaction and prioritize that, I think the better and it's the more we can differentiate ourselves, whether it's with clients or with accounting firms as partners. And so when you're thinking about how to apply AI and automation in your firm or if you're a vendor like in your accounting channel or go to market strategy, maybe automate the lower leverage tasks that aren't the human interaction, which is high leverage, hopefully that's helpful. Time to wrap things up. It's been a great night. Again, thank you everyone for coming out and enjoying the Ramp headquarters. I think we've got room out here to chat and ask more questions if you guys want to stick around. Otherwise, have a fantastic night and hope you guys get a good dinner in the city.

Thanks y' all for being here.

A heads up for my podcast friends. We put together the biggest, scariest project my team has ever worked on. A big old run of live events around the country headed up until year end to to ensure that your 2026 is just the best year ever. Let me run you through the cities real quick. We're coming to Austin, Oklahoma City, Phoenix, Seattle, Portland, San Francisco, Los Angeles, Atlanta, Nashville, Chicago, DC, Philadelphia, NY City and Boston with some super cool half day workshops that roll into dinners. You get CPE for it. It is an event that is built for your entire team to get the whole squad feeling inspired so that if you are a firm leader, you're not feeling like you got to put everything on your back. Headed into 2026 going to be a super fun experience. It's going to be a surprise guest at every city. We're going to record an installment of the podcast live at each of these events, you're going to be part of the podcast itself. What? And, man, I would love to see you there. To learn more, head over to jasononfirms.com events and I hope to see you there.