How Sam Leon Uses Claude Cowork to Prep Tax Returns 5x Faster

0:04David Leary: Anybody who says they've built autonomous AI and accounting or finance is full of crap, right? Nobody has figured out how to do that yet.

0:11Blake Oliver: Coming to you weekly from the OnPay Recording Studio.

0:16David Leary: Hey everyone, and welcome back to the Accounting Podcast, your weekly roundup of news in the profession. I'm Blake Oliver.

0:22Blake Oliver: And I'm David Leary.

0:23David Leary: And in this episode, David, we have an interview with Sam Leon, founder of the Millennial CPA, a firm of one who uses Claude Cowork to do tax prep five times faster than he used to do it. And it's this 30 minutes we spent with him. We're going to talk to him. You'll hear from him about how he uses Claude Cowork, what he does. It's actually really simple and really inspiring. So stay tuned for that in the second half of this episode. But first, David, let's thank our sponsors.

0:57Blake Oliver: Yeah, our sponsors this week, we have Digits, Value Builder System, OnPay, and Cloud Account and Staffing. Let's be honest, accounting software hasn't changed much in decades. The prices keep going up, but the software still expects you to do all the work. Digits is different. Digits is the world's first AI native general ledger with built-in AI agents trained on your firm's standards across every client in your book. They code transactions, prepare schedules, reconcile accounts, run quality checks, even chase clients for open items. So your team moves out of prep and into reviews, advisory, and the work that actually grows the firm.

1:34Blake Oliver: And because everything runs inside one platform, your ledger, reconciliation, schedules, reporting, bill pay, client collaboration, there's no more stitching six tools together just to close one client's books. Firms on digits are reporting a 70 % gain in workflow efficiency, shipping annual cleanups in days instead of weeks, and running monthly bookkeeping in one to three hours per month. Running monthly bookkeeping in one to three hours per client. Accounting software that actually works for your firm. To see why hundreds of firms are making the switch to digits, head over to accountingpodcast.promo.digits.

2:09Blake Oliver: That is accountingpodcast.promo.com forward slash D-I-G-I-T-S.

2:16David Leary: and let me get that uh url up on the screen there please do visit those urls accountingpodcast.promo slash digits it lets them know that you heard about them on the podcast really helps us out and helps our sponsors know uh who and uh or where people are coming from so david let's get into our first story of of this episode i mentioned the sam leon interview we're going to play that in the second half, we're going to start with the Trump IRS immunity deal.

2:48Blake Oliver: Yeah, I think after we recorded last, when our last episode recorded, I went out to the living room, sat on the couch for a second, and I saw a newsflash that it was basically the Trump IRS suit has completely basically been dismissed. And I think I texted you because it wasn't really clear. It happened when we were recording the show, but I do have some information on this. So a federal judge basically demolished Trump's$10 billion IRS lawsuit. Yeah. Called it a sham that was designed to manipulate the courts and funnel taxpayer money into his allies. Ultimately, the main part of this that's essentially been voided is because there's no, and we talked about this early on, there was no actual, you can't sue yourself.

3:31Right?

3:31Blake Oliver: And that was actually fundamentally the issue.

3:33David Leary: So the issue is that, yeah, Donald Trump as the executive, as the president, is in charge of the IRS. And so he's both the defendant and the plaintiff.

3:42Blake Oliver: And the plaintiff, right? And you can't do that. And then on top of that, you create this thing called a settlement, but he didn't settle with anybody. So he's no longer about to refer to it as a settlement. He settled with himself. He settled with himself. So there's no actual settlement. So you can't use that terminology. and this judge pretty much voided the entire thing. So the protections from the IRS and future audits, like it's all basically been voided. It's like this never happened now.

4:10David Leary: And in case you're just tuning in to all of this, this is the settlement that Trump and the IRS agreed to around the leak of his tax information to the press back in 2019.

4:23Blake Oliver: And not only did she void that, she actually referred one of Trump's lawyers in the suit to the Florida bar for potential disciplinary action and then limited the ability of another lawyer, Daniel Epstein, and the practice for the Southern District of Florida. So it feels like lawyers should know better not to file a lawsuit when both parties are on both sides, the same person, right? Now, one thing I saw in one of the comments on the story, and this makes a lot of sense. So when Trump's no longer president, in theory, he could bring this lawsuit up again, right? And sue, because now he's not going to be on both sides of the, he can't be plaintiff and defendant at the same time.

5:03Blake Oliver: And if he, once he's not president, he's not the defendant anymore. He can just do the complaint.

5:10David Leary: I guess so. I don't know. We'll find out. Nobody else has ever gotten a deal like this before. So I somehow doubt that if he wasn't president, he would get this deal. Yeah. I've got some follow-up in the tax world, tax news. In California, that billionaire tax is moving toward the ballot. And I spotted a story from the Los Angeles Times by Nicole Nixon in CPA Practice Advisor about how Democrats are split on this issue. It was supposed to unite them, but now it is dividing them. This is California Proposition 40, which would impose a one-time 5 % tax on the state's roughly 200 billionaires, just 200.

5:52David Leary: And supporters say it would raise$100 billion to offset Medicaid cuts, signed last year by Donald Trump. It is being championed by the SEIU, United Healthcare Workers West, and it is now opposed by the California Teachers Association, the State Building and Construction Trade Councils of California, Teamsters California, and AFSCME, California, are supporting it, but other labor groups have not weighed in. And Governor Gavin Newsom has aggressively opposed the tax and has tried to negotiate its removal.

6:27Blake Oliver: Which makes sense because he basically worked for the Getty's or has worked for the Getty's or is part of the Getty family. He has connections to billionaires. Of course, this makes sense.

6:36David Leary: Well, and if he has presidential ambitions, then a wealth tax like this is not going to Yeah, you can't be like... ...look really good. Yeah. Yeah. And so there was a poll recently on support. So do Californians support this even? A March poll said that 52 % of registered voters supported the billionaire tax, 33 % opposed it, and 15 % were undecided. So very, very slim margin on support. That was from UC Berkeley Institute of Governmental Studies. So the push is to put this on the ballot and let the citizens - Well, it's on the ballot as a proposition. It's going in November. Yeah.

7:17Blake Oliver: So the 40 million non, 45, 60 million non-billionaires that live in California are going to vote against the 200 billionaires. This doesn't make any sense. I guess if you did some serious marketing, you could convince the common man to vote in favor of the billionaires.

7:37David Leary: So I've got some more follow-up in tax, this time in New York, that PA de terre tax, in other words, the luxury second home tax. It is being rushed into place after the state added it to the annual budget in May. And now real estate lawyers, brokers, tax attorneys, and industry groups are complaining that the rules don't make sense. they don't have enough information to actually file these taxes. It's estimated to raise$500 million this fiscal year to help balance the city budget. And commenters have said that the rules leave major practical questions unresolved, including how residency will be proven, whether temporarily vacant apartments count, and how the tax applies when an apartment is rented to someone without a New York tax return.

8:28David Leary: Peter Blonde, a tax attorney, called the tax a confiscatory and half-baked money grab. One of the other big concerns is co-op liability. Under the statute, co-op buildings may be liable if a PA to Terra owner doesn't pay, even though co-ops have no authority to force that owner to pay the surcharge. And there's 11 ,000 properties that are estimated to be affected by this, which includes 515 co-ops. Zal Kumar, an EY tax principal and former finance department official, said the statute does not account for common ownership structures, including spouses using a trust to own a residence. And under the current language, only a trust's sole beneficiary can prove the property as a primary residence for exemption purposes.

9:17David Leary: So lots of issues for New York attorneys, and I'm sure accountants at some point too, to deal with when it comes to this luxury second home tax. All right, David, let's go ahead and thank our next sponsor, and that is Value Builder System. Are you ready for today's magic number? It's 12%. That's how many of your clients received a written offer to buy their business last year, unsolicited, out of the blue. And when that offer lands, it triggers a wave of high-margin advisory work like tax planning, estate planning, and quality of earnings. These engagements often run into six figures. The problem is to most of your clients, you're the tax pro.

9:55David Leary: So all that lucrative advisory work goes to someone else. The estate plan goes to an attorney. The wealth work goes to a financial advisor. You find out about the deal when the K-1 hits your desk. The end game conversation is upstream of everything. Whoever has it first wins all the work that follows. That's where Value Builder comes in. It's the exit readiness platform built specifically for accounting firms. You can assess every client across operational, personal, and financial dimensions, benchmarked against data from over 80 ,000 business owners. You'll spot who's closest to a transaction and exactly what gaps need fixing.

10:29David Leary: Ready to start leading the endgame conversation with your clients? Head over to accountingpodcast.promo slash value. That's accountingpodcast.promo forward slash V-A-L-U-E. And welcome to our live stream viewers. We've got Tate here and Siobhan, boring accountant with three coffee emojis. Boring accountant says, is it Thursday already. Yes, it is. We're recording on Thursday instead of Friday this week because I am taking a little vacay. Vacation. Yeah. And I'm going to be scrambling to get out of here on time. So, David, I'm going to leave you to close out the episode at the end.

11:04Blake Oliver: I think I can handle it. Okay.

11:05David Leary: I think after 497 episodes, you're ready to push the - Push the button, the end button. I think you actually had to do that once a long time ago. I think before. I'll be all right. Something went wrong. I can handle it. Yeah.

11:18Blake Oliver: Have you been following kind of the drama around Xero's CEO and the pay? No. Fill me in. It's been going for a while. The Xero's board, well, let's rewind further. Xero has now a U.S. tech CEO. And CEOs of U.S. tech companies have very huge compensation packages. And apparently, investors in New Zealand and Australia are just not comfortable with this. Like it's just, it's way too much money. So they've been negotiating, especially since ZERO's price stock has dropped because the Sesc apocalypse, right? Intuit, ZERO, all these stocks are being demolished.

11:59David Leary: Yeah, ZERO's price is, I want to check it out while you keep going.

12:01Blake Oliver: So they've been basically trying to negotiate paying her less. They want to reduce her total compensation package. Well, things just got even more complicated now this week because she sold 100 % of her remaining shares for$2.2 million. It said it was because she had to pay taxes. She had a tax liability, so she had to sell the stock to pay her tax liability. But I'm wondering if this is a little bit of a negotiation tactic, because the stock price is down. So if she was getting heavily reimbursed or paid through stock, she's not getting paid very much. And so she's almost like nukes it. Like, fine, watch this.

12:41Blake Oliver: I'll sell all my shares and now all of you will take a hit. right? If you go to the five-year, it's almost at a five-year low now.

12:50David Leary: I'm looking at one year, and we're down 58 % over one year. And five years, it's down 53%. Which is almost a five-year low. Yeah. And if we look at the max, it's back to around where it was in November of 2022. and then before that it was like at 45 bucks in April of 2020 and we're at 47 now so but it doesn't

13:17Blake Oliver: like you think about the the bigger thing with this is the image right you have arguably people arguing zero it's over for zero it's over for QuickBooks they can't do this because all the new AI players are going to destroy them they've destroyed the market has destroyed the stock price of these companies, and then you have the CEO selling all their shares, it makes you question, is there faith in this?

13:42David Leary: I think the markets are wrong on this. I kind of do too a little bit. I do not believe, I mean, for this to make sense, you have to buy into the theory that small businesses are going to start vibe coding their own accounting software.

13:59Blake Oliver: Or switching to all these AIGLs, these new startups that exist.

14:02David Leary: Or doing it with Cloud Cowork in Excel. And having done that, which I just did this as an experiment a couple weeks ago, having done it, yes, it's doable. But the problem is then you have to review so much. And everything looks so good that it's hard to know if it's right. And it's just not easy to guide the AI to do this. So you need Rails, right? You need a system like a general ledger like QuickBooks or Xero to put your numbers in so that whoever looks at them for the tax work can trust them.

14:40Blake Oliver: And also, I think these investors are punching the stock. There's some mindset that like, well, Xero and Intuit are not capable of taking advantage of AI. But if you think about the size, and I think I said this on the show before, if you think about the size of Intuit, But if they just get a 1 % bump of efficiency from AI on the development side, customer-facing side, wherever, it adds up because of the massive scale. I actually think they're probably set up to win because of AI. If we truly believe AI is going to do all this accounting stuff, they're probably set up to win.

15:10David Leary: I think so. Because if you think about it, the hard part about building software, the truly difficult part, time-consuming part, has always been the user interface. Yeah. And what AI lets you do, if you plug your app into Cloud or into ChatGPT or whatever with the MCP, so that your users can just do stuff in Cloud, and then magic happens in Xero or QuickBooks, if you do that, you don't have to worry about building these complicated interfaces. The product design has always been, I believe, the hardest part about building software. So like you said, David, this could actually really help them. But they just have to do that.

15:48David Leary: They just have to enable these MCPs to edit transaction level information across the whole GL.

15:55Blake Oliver: Allow people to get to this data as fast as possible and do things with it as fast as possible.

16:00David Leary: And I think it's a winner. And if they don't, then you've got companies like Digits and the other AI GLs that are just going to come after them and take their business. But I really don't think we're going to have small business owners vibe coding AI GLs anytime soon.

16:16Blake Oliver: so yeah and ultimately at the end of the day this is just optics it's just bad timing like like like there's no confidence in these companies as it is and then when the ceo sells all their stock even if it's personal and it's a planned stock sale whatever it might be it just doesn't look good on the optics like the street's going to panic even more and it actually caused the

16:37David Leary: stock to fall a little bit more so so here's something to back up my uh thesis that it's going to take a lot of review to check these AI outputs. And that's why the small business owners aren't going to vibe code their own accounting stuff. Accounting Today technology editor Chris Gaetano is reporting that AI's promised productivity gains in finance are being consumed in large part by the time required to check, explain, and govern AI outputs. He highlights a recent SAGE survey that found that nearly half of finance professionals are spending over 15 hours a week on verification, and 19 % of them spend more than 30 hours a week verifying AI outputs.

17:27David Leary: And SAGE is calling this the verification tax of AI. only 9 % of respondents plan broad autonomy for transactional finance. They are not moving into letting it just do the work on its own. So that means if you are not going to let it be autonomous, which I don't think anybody has figured out how to, anybody who says they've built autonomous AI and accounting or finances is full of crap, right? Nobody has figured out how to do that yet. And so it just creates a ton of review work. And that's your bottleneck now. And so if you increase the throughput of the prep work, you just increase the load on the reviewers.

18:09David Leary: And we have a shortage of people who are qualified to actually review that. We don't have enough managers and directors and partners. We don't have enough controllers and CFOs. And so, you know, it's...

18:24Blake Oliver: We're just shoving the bottleneck to a different spot, right? Right. The bottleneck in theory was the data entry. Now we've moved it to the review of the data. Yes.

18:35David Leary: Now you can use AI to help you review faster and to become more productive. You know, like that's how I use it, right? Like AI enhances my judgment. It allows me to make decisions faster, to figure things out quicker, but I have to still think a lot. And I have to have the ability and the experience to do that thinking.

18:57Blake Oliver: If it's doing work for you, at the end of the day, you don't want it to represent you poorly, so you have to review the work. Yeah. That's a cognitive load it takes time to do.

19:08David Leary: And so that's why we're not seeing jobs get displaced. CPA Practice Advisor syndicated a Los Angeles Times story by Nilesh Christopher that features There's new research from Ramp and Revelio Labs that suggests that companies making serious AI investments are actually adding workers, not cutting them. So the more that your company spends on AI, the more they are likely to be hiring. It's not cutting jobs. And this was a study that tracked AI spending and workforce records at nearly 22 ,000 US companies from 2021 to 2026. Firms that spent more on AI increased total headcount by an average of 10 % in the two years after rollout.

19:54David Leary: Companies with the largest AI investments expanded entry-level hiring by 12%. Heavy adopters spent more than$100 per month per employee on AI and used more advanced tools, not just basic chat GPT access, for instance. So we are not seeing jobs go away. We have not seen this in accounting. We've seen the accounting job market hold firm, even though everyone says accounting and finance can be automated best by AI. There are parts of it that can, but the review part, the checking the numbers part, cannot at this point.

20:29Blake Oliver: So an article I saw from Indeed's Hiring Lab. So Indeed's like a job posting board. So they have their hiring lab. But they have a new report that came out. And basically, it's the percentages of job titles and job descriptions that now include the word AI in them. or include AI in these jobs. It's more than tripled since 2022. So these are other positions at companies that are not, it's not the AI job, right? It's another job at the company says you have to have some AI. You have to have the skillset of AI in it. What's interesting though, is the shift where 63 % of titles that have AI in it are not in tech companies anymore.

21:09Blake Oliver: So this is just mainstream businesses or hiring somebody in the business. Maybe you're hiring an accountant and you're going to put in the job description, you need to have some AI skills or wherever it might be. So you're right. The humans that have AI skills now, that's who's going to get jobs. So it's creating jobs, creating, replacing, I don't know, up-leveling. I don't know what the right word you've honestly called this.

21:33David Leary: Yeah, I like up-leveling, right? Up-leveling, yeah. The workers we need are higher level. Higher level. Tate in the live stream says, there is a technical gap with tech. there always has been. With Excel, for example, we have had macros for the longest time, but most accountants, more than 99 % can't use them. Worse with AI. That's true. And that's why this interview with Sam Leon is great, because the way he uses Claude is actually very simple. And it's a great example of how you can do tax prep work in a faster way. So can't wait to get to that in about 10 minutes here. David, I'm going to go ahead and thank our next sponsor.

22:08Blake Oliver: Yeah, while you do that, when you come back, we're going to play a quick little game. So I'll get it right.

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22:49David Leary: Their seamless QuickBooks and Xero integrations eliminate manual journal entries, and they support any type of business you serve. Farms, restaurants, nonprofits, you name it. OnPay can handle unique requirements without adding complexity. And OnPay keeps pricing simple, too. Everything your clients expect, from multi-state filing to off-cycle pay runs, it's included. no hidden fees and no surprises to book a demo head over to accountingpodcast.promo slash onpay that's accountingpodcast.promo forward slash o-n-p-a-y all right david what's this game you got what's this game okay i feel like every time you have a game for me i never

23:25Blake Oliver: get the right answer so i'm nervous i found a thing so this thing that it does but and tell me what you think it could be an app it could be ai etc so it sorts transactions into groups It can add and subtract amounts. It can maintain running totals and balances. It can generate subtotals when an account, department, customer, and employee changed. It can print formatted reports, statements, registers, and summaries. Like, how does it sound? Like, this is exciting tech, right?

23:52David Leary: Yeah, it sounds riveting. You'd want to get this, right?

23:56Blake Oliver: What this is, this is IBM's 402 accounting machine that was introduced in July of 1948. And what surfaced this is there was an article I found on scienceblog.com that talks, tells a story about, there's a Texas filtration company called Spark Roller Filters. So they make water filters of some type. And they've been, they used this computer until 2020. The world computer slash, it was a punch card system, right? They've used it. So they used it for, I mean, this computer is now like 72 years old, right? They've been using it since. since they acquired it in the 80s. And the reason they couldn't replace it is because it meant retraining staff, decades of processes.

24:41Blake Oliver: So your processes are built around your tech, right? So there's risk of errors. If you've been doing your business the same way for decades, why replace a system that's working, right? And we've talked about this in the show. There's companies that have started up just because ERP migrations are nightmares, right? They probably would be struggling still trying to replace this. But you figure there's no RAM, there's no storage, there's no software. It was either punch cards or these little module electronic things you'd shove in there.

25:14Blake Oliver: So it took them like 70 years to like abandon this, essentially these old procedures. And so if you think about like this in the current world, right, we're basically, oh, AI will do all these things. It's great. AI is basically doing what IBM's card punch machine did in 1948. It's kind of doing the same thing. So this is why it's so hard, right? Like starting from scratch, you could totally implement some new technology, new AI tools, et cetera. But if you're on a system already, be it QuickBooks Desktop, which there's still what, half a million people running QuickBooks Desktop, just on Rightworks, I think still, there might be 2 million people still using in QuickBooks Desktop.

25:54Blake Oliver: So how do you, it's very hard to migrate to these new technology stacks, right? And that's the lesson here. And if it's working, it can work forever, right? I mean, almost forever. And you know, that's one of the things

26:07David Leary: that's kind of tricky about AI that I've realized over the last year. We have AI workflows that I built two years ago now. And some of them have started breaking because the models that I had selected are no longer available. Or just for whatever reason, something has changed about these integrations that doesn't work anymore. And I'm the only one who knows how to fix it at our company. And I'm realizing that's a risk. And so if you're building AI workflows, tools, vibe coding at your firm, you're going to to end up having to spend on a team that can maintain those tools. You are now a developer or an engineer.

26:55David Leary: And so that's one of the costs I don't think that people are really thinking about right now.

27:02Blake Oliver: And that was one of the thoughts that went through my head. So when everybody listens to the Sam Leon interview, I was like, how much is this scales? Is this scalable or is this just Sam in his firm? And that's that tricky part.

27:16David Leary: Tate is asking in the live stream if I ever have hired a developer. And the answer is yes. We have developers who work on the Earmark app, but all the no-code stuff that is not part of the app that creates the stuff that goes in, that's all me. And so I have workflows that I've built in Zapier and Process Street to create all that, to take a podcast and turn it into a CPE course. And then once that happens, it goes into our app, and that's what the developers work on. But we haven't hired somebody who just does that because it's always been me. And I think at some point we're going to have to.

27:55David Leary: And the other thing, too, is that—

27:55Blake Oliver: But we also have a system that's working. For us to replace the system now is mind-boggling. It would be almost impossible. It's very, very hard to replace everything.

28:04David Leary: And upgrading them is challenging, too. And you need to do that every now and then. So like, for instance, we have this workflow that writes articles about podcast episodes. So when this episode gets published, we take the transcript and that goes into a workflow that creates an article about the episode. And they're very well written. I mean, and this is something that we just, like I built it because I wanted to create that content to put that out there on the internet so people could find it. but we didn't have the budget to hire a writer to spend hundreds of dollars on every episode to create a good article.

28:42David Leary: And I was able to build that with AI, but I had to build it in kind of a different way than I would do now. And so when it broke last week, actually it was this week, I went back in and I realized not only do I need to fix it, but I have to spend time upgrading it. Because now - What about that?

28:59Blake Oliver: Technical debt is what you call that. Yeah. Technical debt.

29:01David Leary: There's technical debt in all this AI stuff too. And I think that's also a big challenge. So let's go ahead and get to our interview with Sam Leon.

29:11Blake Oliver: I was going to say one more thing on this. This ties back to the, oh my God, it's zero and QuickBooks are just toast. They're done because of all this AI stuff. Literally people are still using IBM 1940 accounting machines in the year 2000.

29:29David Leary: And that's the thing is like these businesses that are already on Xero and QuickBooks, they're not like very few of them are going to - They're just going to rip it out. It's not worth it, right? Especially if your business is growing. So they have really, really sticky businesses. And I just think the markets are totally missing the mark on this. But maybe I'll be proven wrong. We'll see. I should put my money where my mouth is, buy a bunch of stock. All right, David, let's get to the interview. Actually, first, let's thank our final sponsor of the episode, and that is Cloud Accountant Staffing.

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31:14David Leary: Sam Leon runs the Millennial CPA, a digital tax practice in Richmond, Virginia, with one office, zero employees, and about 70 % of his budget spent on technology. Accounting Today named the firm to its 2026 Best Firms for Technology list. His model, AI does the prep, he does the review. He treats AI like a junior preparer and casts himself as the senior reviewer. He also writes about AI for Accounting Today. and is even building his own software. And his plan is to not hire until he hits a wall. And that wall keeps moving. Sam, welcome to the show. Thank you. Thanks for the intro, Blake.

31:57Blake Oliver: The reason we discovered Sam, right, Blake, is he made some top list.

32:01David Leary: Yeah, the Accounting Today Best Firms for Technology list.

32:04Blake Oliver: But he's a one-man firm.

32:06David Leary: And is that still the case, Sam? yeah no i i still work with with just me um you know and and like i mentioned that that's kind of my plan for for about as long as i can swing it and you know also you know i can get more into it but you know there is so many different firm models and i do happen to take clients that are more complex. So I feel like there's a bit of a ceiling anyway, but with the things I've been working on and like the, the workarounds and stuff that I was discovering in Claude this tax season, I think a lot of what I've been doing is applicable, whether you're a firm that does like lower volume, complex clients or super high volume.

32:53Um, cause there's just use cases for AI in any of those cases.

32:59David Leary: Well, I would love to jump into what you're doing, what you're actually using AI for? Or your firm.

33:06Blake Oliver: Who works for your firm? AI agent A, AI agent B? Yeah. So it's interesting you say that. So I can also just give the super brief background on myself of how did I come to start this firm? So yeah, before this, I've been in tax and accounting for like 13 years. And most of that was just some diverse tax experience. You know, I started with more like general tax, you know, one of these shops that where there's just like tons of W-2s and Schedule Cs. And then later on, I went to like high net worth and trust and estate tax. And then for the past like seven or so years, I was working almost exclusively with startups, especially yeah, venture backed C-Corps and started doing R &D credits for them as well.

34:00So just as a little background, I got kind of deep into the tech world on just purely the accounting side. And so it really built up my interest and understanding of how tech companies in general run. So, you know, when I was at the last firm that I was at, you know, not any issues per se, but I did want to go start my own firm partially because of this interest in being tech enabled. And, you know, at that time, you know, that firm had, well, we had a tax department. It was probably like 20 people, you know, doing like six or 700 returns. And yeah, there's just so much room for improvement, like with the software and AI.

34:44And that's not something that you can just get signed off on. So I had to go do it myself.

34:50Blake Oliver: So you're working with these tech founders and you caught the bug, the entrepreneurial bug to start your own firm. Yeah. No, I definitely did. That's definitely part of it. Was there like a learning you had of like watching different tech founders and be like, oh, I like how these guys who are doing it on their own, were they solo founders versus people that have this huge team and a board? Was there anything that caught your eye that said, if I ever go on my own, I'm going to do it this way? How did you decide to be a one man firm versus a traditional model? yeah i guess um yeah in terms of what i saw you know i think the biggest thing i saw which is anyone who gets slightly into the tech world sees you know there's you know so much money being raised and so much venture capital and not everyone makes it so i think it's not so much about whether you raise money or not it's probably more about conviction which i definitely had so So yeah, to go back to something that I think you just said, David, because you were like, well, do you have AI agent A and AI agent B and such as kind of employees?

35:53And so that was actually my first idea like one year ago when I decided to start this and I was like experimenting with it, you know, and like chat GPT probably. And I just feel like the technology like was not quite there. it's like I would try to create like different like GPTs or projects or whatever and say like you're the marketing person you're the you're the tax expert um but it was still like a lot of copying and pasting so I was kind of like okay I'm gonna table this for a while and then just focus on you know just opening my firm which I knew I was gonna call the millennial CPA because I had been sitting on the domain for a while because I was trying to use it as a blog like five years ago and just didn't end up doing that, but I still had the domain.

36:40And so I was like, okay, I'm going to, you know, be the millennial CPA and be totally tech enabled. But, you know, two things do come up, which is, you know, how much do we as practitioners care about AI and being tech enabled? And then, you know, how much do your clients actually care? And I feel like that's something that came up a lot that I'm still thinking about is like, the clients don't necessarily care that much. So I kind of got more focused on just how do I implement it, you know, for myself to, to streamline what I'm doing.

37:15David Leary: And so it sounds like you're using it mostly for tax prep. Is that right? Yeah, definitely. Mostly tax prep. Yeah. And especially like during this tax season, you know, it's like getting my clients and I started to get more into like, because I guess what, I guess back up, what started to really interest me is, you know, for a little while now there's been some prominent like tax tech or tax AI software that's literally putting the numbers into the tax return. And that's great. And I've tried it out a little bit myself. But like I said, I had complex, I have complex clients and the use case wasn't really a hundred percent there for me.

37:58So I ended up being the most interested on how do you automate everything except for that so that you reach a point and then you're just spending a short time, you know, just putting some numbers in the return, but they're all there for you already. So I started to get really invested in that. And just in my view, there's so many things about the tax firm process that can be automated. And of course, I've seen it firsthand myself over the years. It's like just the process to the point where you're even sitting down and putting accurate numbers in a tax return. There's like seven hours of work that already had to happen just to get to there, you know, three to seven hours, let's call it.

38:42So I started thinking like, how do we automate that? You know, how can you automate every step? You know, how can you, you know, have your client sign the engagement letter and populate, you know, into your CRM, you know, how do you make like make the request for tax documents in as automated as possible of a way. So things like that. And then getting to the point of tax work, getting deeper into the tax work, that's when I started to hit the wall and start to like brainstorm and experiment of how do we actually use Claude or Claude Cowork, you know, to help make work papers and things like that to prepare for the tax return, because obviously you can't just drop these into Claude, you know, with all the sensitive information.

39:30And so that became a problem that I was really interested in solving, and it pushed me more towards the creating my own software path that I'm sort of on today as well.

39:42David Leary: all right i want to talk about the software but like first can you just walk us through what you're doing with one return end to end what are the yeah what are the what is the ai doing what have you built like i i paint a picture for us like of your yeah so so end to end um yeah once you get to the point where you know where you've collected the tax documents which again is like

40:09Blake Oliver: some more yeah admin type can you go further back to the beginning than that sam because i'm on your website and it's very clear that like it's attractive it looks like it's effective marketing like it's well done but you have this monster button this huge button on your website that says smart intake like so start there talk about that yeah start start from the beginning of the workflow not just when you start working on the return no that that's fair yeah no i can start there because that was actually the first like piece of tech, I guess you could say that I built. And that's kind of how I, I marketed the whole firm back in December, uh, when I, when I started.

40:46So yeah. And, and that was basically, I designed that to, uh, solve a problem that, you know, I had seen over and over again at my old firms, which was like, as the clients are flowing in, you're trying to scope the client, you know, and for tax that that's happens in, I feel like a pretty specific way because, you know, a problem that, that we would always face is just, okay, it's, it's underscoped or it's overscoped. Like we didn't understand how much this client actually had going on and we didn't charge correctly for it. So, and then of course there's like the, the translation to the layman's, you know, the, the clients don't want to hear about all the forms And, you know, you have to like break it down for them of what's of them hearing what's going on and us hearing, OK, that means that there's these like seven forms we can expect.

41:39We know how complex they are, et cetera. So it's an intake design to do that. And it did you know, I did have several people fill it out, you know, and it definitely provided me valuable information about them. And I think, you know, for them, I'll put it this way. No one complained about it. No one, none of them came to me and said, like, I love doing this intake because I think at the end of the day, you know, your prospective clients don't want to have to do too much to get the engagement going. But they did seem to fairly appreciate it. And, of course, I appreciated it because I had, like, a ton of information about them and could scope them and can scope them really quickly.

42:22Blake Oliver: And that's a custom app you built, this intake form? Yeah, yeah, I built it. Yeah, it's, it's built on this.

42:31David Leary: It's built on like a platform that allows you to build like intake forms or funnels called involve me. But yeah, I, I went with that ultimately, just because I wanted like a first differentiator, you know, in this being a tech enabled firm. And that was the first problem that I was really thinking a lot about is like, how do we automate intake better? Okay, so you've got the intake form. I fill it out as your client. What happens next? Yes. So then what happens? You fill the intake. You know, it's going to invite you to book. We'll just assume you're a client that's heading toward becoming my client.

43:16So it's going to send you like my, you know, potential calendar time. So like, then let's say they just schedule it, you know, we get on a call. That's where I determine that everything on the intake form is accurate and see what else is going on. So like, let's say our call goes well, like 15 minutes, half an hour. I'm going to send, you know, one of my engagement letters, you know, which I made as many templates as possible. And I've been using Ignition, which I do like. And I was like, okay, eventually I'm going to figure out how to automate this more. But, you know, I had my templates. So let's put their info in a template, send it out.

43:57Because then billing is going to be automated from that point too. And then that's when I started building more. There's more custom features, which, because just backing up one more time, before I built like the software that I'll eventually mention, I was just building my own apps, I guess you would say using Slack. So I would then literally type the name into my Slack bot, into Slack. And the Slack bot would take that and populate my CRM with the relevant information and like open a profile on them in Taxdome, which I was using. And then, you know, there's some automation features that I sometimes use the TaxStone features, but I eventually moved into using my own of basically then like either drop it into TaxStone or redact my own PDFs and get the list from Claude of what documentation we're expecting.

45:04and then you know cross check that but like come up with the list of the expected documentation pretty easily send that over to the client you know open their portal so that they have access to all that and then from there pretty much just wait for the documents to flow in it's gonna like check off at the end when it's when they're all in and then I'm gonna go check it And then, yeah. And so then that's the moment when it's like, okay, it's time to prep. Okay. Okay.

45:35David Leary: Can I stop you there? So that's the first AI step is you're using Claude, is it, to create that PBC list? The client docs. Okay. So that's okay. And then you load that into the portal and then you wait for the client to submit the docs and then, and then, then that's where we're at. Right. So then what, what happens? Yes. Yeah. So, okay. So let's say you've got all your docs, which sometimes, you know, for a while, but that's like a different story. But let's say we got all the docs, and then it's time to create a work paper, or that's how I like to do it, and I think makes it more automated. And that's basically then taking the docs, redacting them in the way that I need to redact them.

46:22And again, Claude is able to say, like, here's the expected schedules, here's the expected totals, and why all that kind of information, you know, which I can again, cross check. And then I have my information to take and input into the tax return, which again, I then do because I haven't yet seen the perfect solution for me and my more complex clients. And that's not necessarily the same if your client base is like W-2 and we have like a 1099 interest. You know, it's going to work, be a lot. There's going to be certain automated off the shelf solutions for that already. But yeah, that's what worked for my complex clients.

47:05And then the other big thing that I got into was creating the AI reviewer, which is pretty much the inverse of the work paper preparer and saying like, okay, these are all the documents and this is all the information and this is the tax return redacted. And is everything making sense here? Are the schedules making sense? And at that point, you should even put in the prior year's return as well and say, like, what's missing? We had all this last year. What's missing? Once you can see that from AI, you'll know whether some of it's relevant or not based on what you know about your client. Okay.

47:45David Leary: So we've got the AI preparer and the AI reviewer. Can you dive in more on this AI preparer? How does it work? Is that in Claude? is that Claude co-work is it like how did yeah like in terms of yeah like the prepare in terms of yeah the the step that i was just mentioning with like the creating of the work paper yeah how does that work how did you build that yes you built that that is yes what you built that that's

48:13Blake Oliver: not third-party app you you built yeah no no that's not third-party i mean it yeah and and it's something that i'm like productizing i guess you could say but like just purely how i did it during tax season was I, you know, wrote out, honestly, sometimes using Claude to help, like wrote out like the SOP of like, what are we doing here? You know, and I think we are at the point where it's like, Claude does understand, you know, what a tax return and it understands that there's like 250 possible schedules or whatever, you know, like there's a lot that Claude understands. And I think in my opinion, it's like, it's almost like programmatic what it understands, you know, of course, what it does not understand is like, necessarily, like, why does this certain number belong here?

49:04And that's part of what the work paper does is it just organizes a little better. So instead of like, trying to guess like, okay, where does this go? Where does this go? It's just more guardrails where it's like, okay, you know, all the investment income, you know, can go to this schedule, you know, this, this certain home sale, you know, we expect on this schedule so basically like guidelines um general guidelines for claude

49:30David Leary: in that case okay so so you have like how is it set up in claude um how i had it set up was um like through some co-work projects like there was like the return review you know there's like that well there was the return review project i found that easier to do a project because it's more uh like automated process every single time this is what a review is the prepare one i would do more so by client so it's like i have my client folder of redacted information um and then just kind of saying like almost like prompting claude to be like tell me what you see you know see if i agree you know say this is the schedules we expect you know just it was honestly more of a dialogue just because i think it's a little bit uh like bespoke you know these these okay got it so it's like a project folder for each client you've got all of the client documents in there that you've collected and then how does this you're having a conversation with claude to complete this work paper is this a like an excel template yeah so ultimately what comes out is yeah like an excel uh template and honestly you know this is where i feel like there's a room you know as a preparer you know everyone or like just as a tax person who's like doing people's tax returns you know everyone has like kind of their ideal work paper their ideal workflow or you know some people wouldn't even use work papers.

51:19So yeah, for me, like, especially being a one person firm, you know, I'm a bit flexible about it. You know, when I worked at bigger firms, there's like, this is the required work paper, this is what you do, this is how you do it. But you know, it's my, you know, it's my records, you know, I'm the only person who needs to be referencing them. So a lot of times, you know, I would iterate a little bit with Claude, but you know, just the Claude saying like, okay here's the excel with all the schedules and and the numbers and why and i would look at it and say like okay this this makes sense to me you know this works i don't need a super specific

51:55David Leary: template here so it can even just generate the work paper on its own you don't even need to necessarily give it a template and it gives you what like in my opinion no i mean okay so you do give it yeah yeah i mean yeah it's it's a kind of like don't try this at home unless you've been a tax preparer for a while, but yes. Okay. So basically you, you have a conversation in a client project folder with Claude to generate the work paper that has all the numbers by schedule that you would then enter into the return. And so then you go do that manually, which I mean, like, I guess that makes sense because you need to like check the work at some point, right?

52:37David Leary: So you, you enter in the numbers. I mean, of course, there's room for that to just push in, you know, at some point. I personally didn't solve it. You know, I think it's a solvable problem, probably. So you said that process of just like putting together that work paper took how long in the past? To put together, yeah, work papers usually takes at least two hours, I would say. um and again there's like a couple things because again you might in the past maybe you wouldn't have created as detailed work papers as i now do i'm almost creating more detailed work papers because it's easy now whereas in the past i might have said like okay let me just type literally type the numbers into the tax return and then tick and tie and you know there's all these like you know tick and tie tools for tax um but yeah like to make especially for corporations like to make like a C corp work paper can take like six or seven hours for sure.

53:39David Leary: And how long does that six or seven hour prep take now? And how, yeah. And how long it took me. I mean, the C corps always take a little longer, but honestly, I feel like the maximum amount of time I was ever like iterating on it in this cloud process was probably like an hour. Wow. So six to seven hours down to a single hour. yeah and then for like a easier return one of those returns that would take two hours how long would that take with Claude I mean that would just yeah I don't like to to make a work paper something that normally would have taken two hours like I don't know I feel like 15 minutes I'm just kind of spitballing but yeah yeah well but that makes sense because what you're getting like uh over 5x productivity boost on the corporate returns when it comes to creating that work paper and then kind of similar for the, I assume that's like a personal return, right?

54:34David Leary: An individual? Yeah. Yeah. Especially an individual with like not, not too much going on. Okay. So then you put the numbers in the return and then you said you also have a review project that you used to check the work. Yes. And I became a big fan of my review project. Cause I just feel like it combines like it combines even more so than the prep things that ai and claude is already really good at you know like here are the inputs like officially and then you need to just match it and you need to tell me the differences um and and that's that's like a three-way match um and that that's something that i you know i i think a lot of tax preparers always kind of do this but that's how I started thinking about it.

55:21And so that's how I set up the project is like the three-way match. Like there's a return I just did. There's last year's return and there's a pile of documents and let's, you know, the pile of documents is like, are the numbers correct? But last year's return is like, did we just miss something? Um, we see what, what, what was there last year?

55:41Blake Oliver: So you silo the prep and Claude as with a project, then the reviewer is also in Claude. you just siloed out the project as well. You don't use two different AIs like, hey, I always do use Jacksonville to review the cloud work. Yeah, and that was just, yeah. I mean, I'm trying to think of how big a difference it makes. I feel like that was just my preference. It just made sense to me because, like I said, it was more like the review process always goes kind of the same every single time. So it made sense in my head to make it a project.

56:14David Leary: And for these projects to work, you have to create instructions. And that's the SOP you were talking about. So you've got an SOP that's a standard operating procedure, instruction manual that you created for the review. And then also for how to do, do you have one for the prep as well? Or is that just more of a conversation that you're having? That was more conversation. Yeah, I think it would be interesting. And that's what I started doing partially as well during this creating software is like making SOPs like for that for the prep um i think it's just more time consuming because there's so many potential uh things that might get prepped have you tried creating any skills in claude or are you just having a conversation so yeah you know i i did some skills um i never in like co-work which i guess i probably could but i i it was always like prompt it would prompt me to create skills more if I was like, like times that I've been like talking to the Claude chat.

57:20So, so as part of these processes, I didn't use any skills.

57:25David Leary: What Claude model are you using for this work, this type of work? Yeah, I've been using, I'll kind of usually just use whatever's like the best or second best model that they're putting out there. Like I tend to do that. I did eventually like, you know, I started like with the pro plan and then I was like maxed out. So I max plan. And now I think I have like the 20 max plan. But honestly, like that's$200 a month. And there's like so much value that it's just it's completely worth it, in my opinion. Yeah. So I tend to just use pretty much whatever is newest unless unless Amthropic is putting like a way more restrictions on it.

58:09like they have like the fable five one now and I feel like it eats through uh your like your

58:15David Leary: credits too quickly yeah so so let's talk about the cost right in the accounting today feature um on your firm the best firms of technology list they said that you spend like 70 percent of your budget on tech so what is all of this ai costing you yeah so and that's kind of interesting thing because, you know, there's obviously like other softwares that I'm using as well, you know, like tax softwares, like huge line item, you know, like different project management tools that I was using, you know, the software that runs my intake, which I was kind of mentioning, you know, and then there's Claude, then there's the fact that I still have my like chat GBT subscription, because I just use it sometimes and haven't canceled it um so like all those and then just yeah other you know there's like so i've always been like a huge like software person as you can kind of tell so like i love trying and testing all these different softwares so i definitely tried my share of stuff for a couple months and canceled it uh that probably ate into the budget but yeah the biggest thing is like probably not that clawed ai spend itself but it's like the other the other stuff So basically, Claude, 200 bucks a month, and you're saving hours on every return.

59:39Yeah.

59:40David Leary: Yeah, that seems like a no-brainer. Exactly. Yeah, no, to me, it was a no-brainer. But yeah, it's like when I see people sometimes talk about like, oh, I don't want to pay for a higher Claude subscription. It's like, why? Because you're going to save so incredibly much time. So when you've compressed the prep work for both a complex and a simple return, how do you decide what to price the return at? Because we sort of, in tax, right, the return complexity has generally correlated with the amount of time it takes to do the return. But it sounds like that is not necessarily as true anymore. So how do you decide what to bill?

1:00:22Yeah. So, yeah. And I think that's pretty much correct. I would say, yeah, obviously the complex is still taking more time. But I mean, since this is so new, the thing is also too, I've never charged by the hour. Um, uh, obviously it's, that's a mixed opinion in this industry, but for years, even the firms I've been working at, we haven't been charging by the hour we've been doing packages. Um, so that's something that I brought right away to my own practice. Um, so when I was thinking about pricing, I was honestly thinking about it, like, okay, what do I, what would we normally charge? Like at any of my firms for, for this scope of work.

1:01:04And that's partially where my intake tool helped, because as you're scoping in more and more stuff, you know, it is taking more and more time. Like, sure, it's taking less time. But, you know, for instance, if I find out a corporation has like an international subsidiary and three international partners, you know, sure, it's going to take less time to like literally get the numbers into the return. But I think there's still a lot of, you know, judgment and there's still a lot of like basically professional experience going into it. So I'm not yet seeing the reason to do like price cuts on this.

1:01:40I mean, you know, we'll see what happens, I guess. But this is all pretty new. And like the judgment side of tax, in my opinion, is still still takes a fair bit of time. Like all the stuff that is in AI that I just mentioned.

1:01:54Blake Oliver: Have you had clients request cheaper prices? Because like, hey, you're using AI stuff, you're using these tools. You know, I actually haven't. And that being said, I've had certain people be non-starters because my minimum price is not cheap. And that's partially, like I said, that was partially by myself.

1:02:15David Leary: Sam, what is your minimum? It's like$1 ,500. That's the new one. I guess last year it was more like$1 ,250. 50. But it's 1500, which, you know, again, that's probably going to be more so for a personal tax return of, again, a certain level of complexity. And, you know, like I said, I felt like that was also kind of like a decision for what niche I'm going for, because I have a lot of experience, I'd rather take the complex cases and just charge more accordingly. All right, Sam, I want to talk about this software that you're building. What are you working on? Yeah, so I am calling it TaxWeave. And what it is and what it came from was kind of the accumulation of not only everything that I was working on that I just discussed with you all during tax season, but also the pain points that I had been seeing for years as I was kind of mentioning.

1:03:20I tried it early on, I tried to solve that intake problem and created this tool, which I felt like was working well. The next thing that I was really interested in solving was the basically organization problem almost at the practice management level. Obviously, there's a ton of practice management solutions out there, but something that I realized at my past two firms in a row is they had tried all these practice management solutions and they were sometimes using them to some degree, but they never were comfortable enough with these solutions to stop maintaining like a master Google spreadsheet.

1:04:01So they have like these huge spreadsheets with hundreds of clients, hundreds of situations going on. And I was just like, this is the next thing that is going to become my passion project, I guess you could say, to try to automate and apply AI to. So So it ended up being this segue into building more so of a platform where it's consolidating your client list. It is your client list, but it's integrating all the other things that you need to know about your client, making it so you can kind of click on a client and understand where they are in a tax process. So I'm doing this by letting it feed in with your email, letting it feed in with your docs portal, you know, your Google Drive or your share file or whatever you're using, you know, space for your team to make notes and basically create like a one-click shop for how do you know what's going on with your clients?

1:04:59And that to me, I started thinking more about it and I was like, okay, that's the perfect foundation for the AI and the agent type actions that, you know, I've been talking about that I've found ways to apply. Like, what if this can be part of a product where not only are you clicking on your client and seeing what's going on, but you can also click on an agent action and say like, okay, we have all the documents. Let's prepare the work paper. You know, we did the return. Let's review it. You know, it can iterate on and on from there. You know, there's so many things that are like templates at tax firms, you know, there's email templates.

1:05:37It's like, okay, let's fill out the email templates. So once I said, and I have successfully now built that layer of here's your list of clients and here's everything feeding in. And I've been building the integrations. And then I've recently, then I sort of hit the limit of what I can do as a novice software coder. And I started working with a couple more tech forward individuals and a software engineer in particular to help me push this whole agents thing to the next level. Because like I said, I feel like I kind of proved it out in Claude already and like with this Slack bot that I created.

1:06:16And I think it's in a place where it can be wrapped into this bigger platform.

1:06:21David Leary: That sounds really fascinating, Sam. Thank you so much for joining us today, sharing what you're doing. If our listeners want to follow you, connect with you, stay up to date on what you're doing, where's the best place for them to go? Yeah, no, they should add me, add me on LinkedIn, because I post about this stuff, I talk about it. And yeah, I would love to just chat, you know, with people about what they've been doing with AI, and hear their thoughts on things I've been working on, too. It's like super helpful getting feedback from fellow practitioners. Follow Samuel Leon CPA on LinkedIn. He's the Millennial CPA.

1:06:59David Leary: Sam, great chatting with you. Hope to talk to you again soon. Yes, great to meet you both. Thank you.

1:07:08Blake Oliver: Well, if you're still tuned in, thank you for listening. Just a reminder, you can get CP for listening to this episode. You can just go to earmark.app in your browser. And if you're on your phone, it'll take you to the app stores to download it. you get one free cp a week for listening to this episode and you can tune in every week and get another cp and another cp and if you're interested in getting unlimited cp you can actually sign up and purchase the an unlimited subscription subscription of earmark for$199 a year i'll see everybody next week thank you

1:07:46Blake Oliver: time for the classifieds

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1:09:16you