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From Data Entry Nightmare to Automated Workflow in One Demo Session

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You’re ten days away from the 1099 and W-2 deadline, and you’re still wrestling with QuickBooks, fielding a flood of W-9 request emails, and dreading the inevitable data entry marathon. Sound familiar?

You’re not the only one. As David Leary admitted during a recent Earmark Expo webinar, “I’ve been procrastinating on issuing 1099s. It’s just not a great experience.” He described the dual frustration that many accountants know all too well. “It’s annoying work on both sides. I need to do my 1099s, but then, as a business that receives them, I get a slew of emails from other companies asking for a W-9.”

In the webinar, David and co-host Blake Oliver took TaxBandits for a test drive with Nikita Sullivent, the company’s Support Specialist, to explore how this IRS-authorized e-file platform handles over 70 tax forms. The live demo included the authentic technical hiccups we all face with real-world software and shared practical solutions for the compliance challenges that hit every January.

Getting your data in: from hours to minutes

Manual data entry for hundreds of 1099s is a bottleneck that keeps you from serving more clients. TaxBandits tackles this with multiple import options that meet you where your data lives.

The platform offers three main paths for getting data in. You can:

  1. Enter forms manually one at a time (perfect for that forgotten contractor),
  2. Use bulk upload templates for larger volumes, or
  3. Connect directly with accounting software (current integrations include QuickBooks Online, Xero, Sage Intacct, and Zoho, with Karbon integration coming soon).

The bulk upload process stands out for its simplicity. As Nikita demonstrated, “You’re reviewing the columns at the top and inputting the data beneath them. Once we have all of that data input, we’ll just download it as a CSV and drag and drop it in.”

David particularly appreciated one detail. “I like how on your templates, in the header of each column, you give the instructions for the values you accept in that field.” No more guessing whether to use “CA” or “California,” or whether TINs need dashes.

The workflow breaks down like this:

  1. Download the Excel template with clear column headers
  2. Fill in your data following the built-in instructions for each field
  3. Drag and drop the file into TaxBandits
  4. Review the automatic error check that flags issues like missing digits in EINs or duplicate records
  5. Fix any problems by either editing in the app or exporting just the error records for correction

For QuickBooks users wondering about the process, David confirmed you can export your vendor list, filter for 1099 vendors, and use the “upload your own file” feature. The first time requires mapping your fields to TaxBandits’ fields, but that mapping saves for future uploads.

One webinar attendee asked whether they needed to re-enter last year’s payees. “Absolutely not,” Nikita answered. “Everything stays in your account and rolls over year after year.” When you import this year’s data and the system finds a duplicate, you can either delete it or update the existing record with any changes.

The platform also distinguishes between importing only recipient data and importing both payer and recipient data. If you maintain TaxBandits throughout the year, importing just recipients during filing season works best since you’ve already set up your payers. But if you’re adding everything at once, the combined import saves steps.

With data flowing smoothly into the system, the next challenge is ensuring that data won’t bounce back from the IRS.

TIN verification: the new compliance reality

Getting data into the system efficiently matters only if it passes IRS validation. The agency’s transition from the FIRE system to IRIS (Information Returns Intake System) brings stricter requirements that every accountant needs to understand.

“The IRIS system is going to be far stricter on TIN matching than the FIRE system was,” Nikita warns. “Which means if the SSN, the EIN, the TIN, and the recipient name don’t identically match the IRS database, it’s going to kick the form back to you as accepted with errors, and you have to file a correction.”

The keyword is “identically.” A contractor who goes by “Mike” but whose Social Security card reads “Michael” could trigger a rejection. Even punctuation differences in business names can cause problems.

TaxBandits builds TIN verification into multiple touchpoints:

  • When collecting W-9s throughout the year
  • When adding recipients to your address book
  • During the 1099 workflow as a final check

The smart approach starts early. “When you get a W-9, when you get a new employee or contractor, you go ahead and do the TIN matching on that prior to the filing season,” Nikita advised. This prevents last-minute surprises when deadlines loom.

Verification typically returns within two to four hours during normal periods. But during peak season “it can be up to 24 hours,” Nikita warned. If you’re verifying TINs within the 1099 workflow itself, the system waits for results before transmitting, which is potentially problematic if you’re filing on January 31st.

For those worried about the cost of corrections, TaxBandits offers some protection. Their “TaxBandits Commitment” covers correction filings at no additional charge. But even free corrections cost you time and stress.

The platform also streamlines W-9 collection. Instead of chasing paperwork, you can send electronic W-9 requests. Recipients complete them online, and the data flows directly into your TaxBandits account, ready for immediate TIN verification if desired.

Once your forms are prepared and verified, you still need to get them into recipients’ hands compliantly.

Distribution flexibility that actually works

The old choice between hours at the post office or forcing everyone into electronic delivery is over. Modern distribution needs flexibility, and TaxBandits delivers exactly that.

“Everything is very customizable to your needs,” Nikita explained when asked about mixing delivery methods. “You can choose some postal mail, some online access, and some want both.”

The three distribution paths each serve different needs:

  • USPS postal mailing handled entirely by TaxBandits
  • Electronic recipient portal requiring just an email address
  • Both options for recipients who want backup

The electronic portal solves a critical compliance issue. The IRS requires formal consent for electronic delivery, so you can’t just email a PDF. TaxBandits automates this. Recipients receive a secure link, enter a PIN for verification, and provide documented consent.

If someone ignores that email, the system tracks everything. You can see who consented, who declined, and who never responded and then handle postal delivery for the holdouts.

For returning recipients, the portal builds value over time. “If you file for that same recipient next year, they’ll use the same link, and they’ll access all of the documents from the same portal,” Nikita noted. Recipients get their own organized tax document archive without any extra work from you.

State filing adds another compliance layer, but TaxBandits simplifies this, too. The platform tells you exactly what each state requires:

  • States requiring direct filing (you handle separately)
  • Combined Federal/State Filing participants (automatic forwarding)
  • States requiring no 1099 filing

Throughout the process, you get real-time status updates so you can see which forms were transmitted to, received by, and accepted by the agency. For postal mail, statuses are submitted to USPS and en route to the recipient. When a client claims they never received their form, you have documentation. After transmission, watermarks disappear from your copies, and you can reprint professional versions anytime.

For firms with multiple preparers, the platform offers even more control through team management features.

Scaling with teams and support

Larger firms need more than just bulk upload; they need workflow management. TaxBandits’ team management features let you maintain control while delegating the actual work.

The system offers three permission levels:

  1. No roles: Any team member can prepare, approve, and transmit
  2. Two roles: Preparers create forms, approvers review and transmit
  3. Three roles: Preparers create, approvers review, transmitters handle payment and filing

You can also create location-based groups. Nikita shared an example. “Say you have a group in Indiana and a group in Tennessee. Anytime you add a new payer and assign them to the Tennessee group, then all of the team members included in the Tennessee group have access to that payer.”

Support is critical when things get complex. During busy season, TaxBandits extends hours to 8 a.m. to 8 p.m. Eastern. They offer phone, email, and chat support, plus an AI assistant that pulls from both their knowledge base and IRS guidelines.

The platform’s YouTube channel provides step-by-step videos for specific workflows. For Sage Intacct users who asked about integration, Nikita recommended checking their channel for detailed walkthroughs showing the complete process from Sage to TaxBandits.

Pricing works on a credits system with bulk discounts. Buy more credits upfront, pay less per form—and credits never expire. As Nikita confirmed when asked about rollover, “Your credits will never expire. So if you want to purchase for the next five years now and get the best price we can give you, go for it.”

Making next year easier starts now

The strategies demonstrated in this webinar show a fundamentally different approach to information returns. TaxBandits treats compliance as a year-round process rather than a January panic.

The IRS’s push toward e-filing mandates and stricter validation isn’t slowing down. The IRIS system is just the beginning of modernization efforts that will continue tightening requirements. But the webinar demonstrated real workflows you can adopt immediately, from template imports to electronic W-9 collection to role-based team permissions.

Ready to transform your 1099 and W-2 workflow? Watch the full Earmark Expo webinar to see TaxBandits in action, including the complete demo of bulk uploads, error checking, and team management features. The platform offers over 70 tax forms beyond just 1099s and W-2s, making it a comprehensive solution for year-round compliance needs.

The End of Data Entry and What It Means for Your Tax Practice

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Elizabeth Beastrom left public accounting 30 years ago because she was sick of rekeying data into tax returns. Now, as President of Tax and Accounting Professionals at Thomson Reuters, she works to make sure no accountant has to do that mind-numbing work ever again.

“I was a lazy CPA,” she admits with a laugh during this episode of the Earmark Podcast. “I didn’t want to spend my time doing work that I didn’t think was necessary.”

In this conversation with host Blake Oliver, Elizabeth and Kirat Sekhon, Thomson Reuters’ Head of Technology, map out their vision for automating the entire tax workflow, from gathering documents to delivering returns. They want listeners to know that AI-enabled firms are going to outcompete everyone else, and the shift from compliance to advisory isn’t optional anymore.

Why Tax Firms Can’t Keep Doing Things the Old Way

The numbers tell the story. Fewer people are taking the CPA exam while more accountants retire every year. Meanwhile, tax complexity keeps growing, which means more demand for services with fewer people to do the work. Throw in private equity firms buying up practices and pushing for efficiency, and you’ve got a perfect storm.

But it’s not just about headcount. The new generation of accountants expects modern tools that actually work together—not the clunky desktop software their predecessors put up with.

“They expect to use intuitive and connected tools,” Kirat explains, “so they have a better experience while they deliver value to their customers.”

So why has tax software stayed stuck in the desktop era while cloud accounting tools have taken off? Kirat points to two reasons. First, tax calculations are hard to get right, and once you build something that works, nobody wants to break it. Second, accountants themselves haven’t pushed for change. When you’re working 80 to 100 hours during busy season, the last thing you want is to learn new software.

“The term SALY—same as last year—still comes through,” Elizabeth notes. “You found a way to do it and you like to replicate that. Change is hard, especially when you have to introduce that to the firm when you’re working 80 to 100 hours a week.”

But resistance to change is becoming dangerous. Elizabeth’s own exit from the profession 30 years ago shows what happens when the work becomes too tedious. Back then, she discovered she loved the advisory side, including talking to clients, understanding their businesses, and making recommendations that actually helped them improve. But she was stuck doing data entry.

“I would spend time talking to my customers,” she recalls. “Some of my best inputs came from the people in accounts payable or accounts receivable. I would get a detailed understanding of their process.” But then she’d have to go back to rekeying tax data, and the contrast was too much.

Building the “Bookends” Around Tax Prep

Thomson Reuters isn’t trying to fix one piece of the tax workflow; they’re automating the whole thing. Their strategy focuses on creating what Elizabeth calls “strong bookends” around their core tax engines (GoSystem Tax, CST, and UltraTax).

The front bookend came through their acquisition of SurePrep three years ago. Practitioners dump all their client documents into the system, and SurePrep automatically classifies them, pulls out the relevant numbers, creates a binder for review, and fills in the tax software. No more manual data entry.

“That’s a huge time savings when you don’t have to spend time doing all of that manual data entry,” Kirat says, “and they can actually focus on the return.”

The back bookend arrived with SafeSend, acquired earlier this year. It handles return delivery, e-signatures, and payment collection, eliminating what Elizabeth remembers as the nightmare of printing, mailing, and faxing documents back and forth 30 years ago.

What’s different about Thomson Reuters’ approach is they’re keeping these tools open to work with competitors’ software too, not just their own tax products.

“It is an open, curated ecosystem,” Elizabeth emphasizes. “If customers find value in part of their workflow, we want to make sure we connect to it.”

Beyond just automating existing steps, they’re trying to eliminate unnecessary work entirely. Take the client questionnaire—that paper organizer Blake’s mom still fills out by hand every year. Thomson Reuters wants to “kill the questionnaire” by using AI to pre-populate information from prior returns and only ask for what’s actually new or missing.

The next frontier is what Kirat calls “agentic AI,” systems that don’t just handle one task but orchestrate entire workflows. These AI agents can use multiple Thomson Reuters products in sequence, making decisions along the way to get a return from start to finish with minimal human intervention.

But everything the AI does needs to be auditable. Kirat stresses that any AI handling tax work must show exactly what decisions it made and why.

“Our customers expect the work product of an accountant to be 100% accurate,” she explains. “Without providing that audit log with the decisions and choices and confidence levels, we’re missing the mark.”

Blake agrees enthusiastically, sharing his frustration with current AI tools that don’t show their reasoning. “I want to know why it matched this transaction,” he says. “There’s an AI conversation for each one of these transactions. Why not give that to us?”

The Shift to Advisory Can’t Wait

If machines can prepare returns faster and more accurately than humans, what exactly are clients paying for? Two-thirds of Thomson Reuters’ customers say they want to shift to advisory services, but most don’t know how to actually do it.

Enter Ready to Advise, launched in June 2024. The tool takes everything from a completed return and analyzes it against potential tax strategies based on that client’s specific situation and goals.

“It will quantify the savings,” Elizabeth explains. “It will ask for more information to get to a range. It will allow you to have that discussion where you can say, ‘Hey Blake, I noticed from your 1120-S filing some potential strategies you should take.'”

Then it walks you through implementing those strategies and produces client-ready documentation. For firms struggling to move beyond compliance, this is huge.

But technology alone won’t fix the business model problem. Clients have been trained to expect strategic advice for free. “I might call my accountant and say, ‘Hey, tell me what this big beautiful bill does for me this year?,’ which is code for don’t charge me for this,” Elizabeth says, capturing the conundrum perfectly.

That’s where Practice Forward comes in. It’s Thomson Reuters’ tool for helping firms understand their worth and develop advisory pricing models. The goal is shifting from hourly billing for returns to year-round advisory subscriptions.

Ready to Advise also solves a talent problem. Traditionally, you needed years of experience before you could offer meaningful tax advice. But with AI assistance grounded in Checkpoint’s content (maintained by over 4,500 subject matter experts), newer staff can contribute to advisory work much sooner.

“That junior associate’s experience, paired with all the knowledge that there is available in generative AI today, is incredibly powerful,” Kirat notes.

Blake shares a personal example that drives home the value of advisory over compliance. His tax preparer advised setting up a C-Corp to potentially qualify for QSBS treatment, which could save millions in taxes someday.

“I can’t even quantify the value of that,” Blake says. “But that’s why I’m willing to pay thousands of dollars for a tax return. It’s that insight, not the return.”

Meanwhile, DIY tax software keeps getting better. Blake describes doing a business return himself using consumer software with ChatGPT open for research. The same process would have taken hours of manual work just a few years ago.

Firms that stick to just preparing returns are going to get squeezed from both ends.

“AI-enabled professionals and firms, they’re going to outcompete and outperform,” Elizabeth warns, “because they’re going to be able to do it faster, better and get to this advisory, which our clients want.”

What to Do Right Now

So where should a traditional tax firm start? Elizabeth recommends figuring out what you hate doing.

“What are your pain points that you hate to do?” she asks. “There’s a pretty high likelihood that I or a talented person on my team is going to be able to say, ‘This is how we can solve that for you.’”

The technology exists today. SurePrep can handle document gathering. SafeSend can automate delivery. Ready to Advise can help you identify tax-saving opportunities. CoCounsel can answer complex questions using curated, expert-verified content. The audit logs are there to verify everything the AI does.

The harder change is mental: accepting that the compliance work that defined the profession for decades is becoming commoditized, and the future belongs to firms that embrace automation as the foundation for higher-value advisory services.

Elizabeth even suggests bringing these concepts into accounting education to attract new talent. Currently, tax courses focus on rules and calculations rather than strategy. After all, accounting is still “the language of business,” as Elizabeth was told as an undergraduate. The difference is that AI can now handle the grammar and spelling, freeing professionals to focus on telling the story.

The transformation won’t be easy, but it’s not optional. As Elizabeth learned when she left the profession out of frustration with mundane tasks, talented people won’t stick around if the work doesn’t engage them. The good news is that automation finally makes it possible to eliminate the drudgery and focus on what really matters: helping clients succeed.

Listen to the full conversation with Blake, Elizabeth, and Kirat for more insights on preparing your firm for the automated future of tax.

Why This SWAT Team CFO Says Your Legacy Systems Are Costing You Millions

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When Ximena Velazquez Maynard stepped into her role as CFO of Legacy Management Group in early 2023, she found exactly what she expected: a disaster. The company was juggling 30 separate QuickBooks files while their 11 nursing homes operated in a financial system where facilities couldn’t even talk to each other. Basic financial tasks that should take hours were consuming months.

But for Velazquez Maynard, this was familiar territory. Throughout her career, she’s been the “SWAT team” CFO who gets called in when companies need their accounting rescued, she explains in episode 32 of The Unofficial Sage Intacct Podcast. And she’s turned several of those disasters into companies that sold for huge profits within just a few years.

A Healthcare Empire Built on Shaky Financial Foundations

Legacy Management Group’s story begins in the 1980s with two nursing homes run like a mom-and-pop operation. Everything changed in 2018 when the current leadership took over with a vision to do something greater.

Since then, Legacy has expanded to 11 nursing facilities (nine in Louisiana, two in Texas), plus a pharmacy and mobile X-ray company. They have five holding companies, property companies, and a management company, all with slightly different ownership structures that need to stay separate for legal and financial reasons.

When Velazquez Maynard arrived, she inherited a patchwork of systems trying to manage this complexity. The 11 nursing homes were using PointClickCare’s financial module—a system so limited that facilities in the same software couldn’t communicate with each other. “It was not created by a very good accountant,” Velazquez Maynard says bluntly.

The remaining entities were scattered across QuickBooks files. At one point, they had 30 separate files to manage.

When Manual Processes Strangle Growth

The impact of these disconnected systems went far beyond inconvenience. Consider what happened when Legacy needed to split a bill among their 11 facilities. The accounting team had to make 11 different entries into 11 different files, plus create corresponding due-to and due-from entries. “They would never, ever reconcile in the end,” Velazquez Maynard recalls.

The lack of visibility created expensive blind spots. Floor spending requirements—a critical metric where nursing homes must spend a specific dollar amount per resident annually—went untracked. Without proper monitoring, Legacy once found themselves owing $300,000 to the government because they couldn’t see their spending trends across facilities.

“We could not see easily on a month-to-month basis where we were trending on our floor spending requirement per facility, which varies greatly,” Velazquez Maynard explains. This meant they couldn’t make informed decisions about staffing levels or resource allocation until it was too late.

During her interview for the CFO position, Velazquez Maynard didn’t sugarcoat the situation. “I hear your issues, I hear what you’re doing. It’s not working because you don’t have the software you need.” Within three months of starting, she confirmed the current setup couldn’t support Legacy’s growth plans.

The Complexity of Healthcare Finance

Healthcare organizations face unique challenges that make financial management particularly complex. Legacy deals with monthly audits, manages resident trust funds under strict regulations, and navigates billing across Medicare, Medicaid, hospice companies, and workers’ compensation.

“It’s a very complicated system,” Velazquez Maynard notes. The company often guides families through Medicaid applications that can take one to six months while providing care regardless of payment status. They serve some of society’s most vulnerable populations, including residents without family who cannot make their own decisions.

The St. Christina facility acquisition shows how operational and financial challenges intertwine. When Legacy bought this facility with “the absolute worst reputation,” Velazquez Maynard discovered a wheelchair ramp that, instead of being repaired, had padding on the adjacent wall to catch wheelchairs that might slide into it. “I was amazed. I was like, this is terrifying,” she recalls.

Legacy invested millions transforming the facility, adding private bathrooms and making it safer for residents. But such strategic investments require a level of financial visibility that’s impossible with 30 separate QuickBooks files.

A Rapid Transformation

Having implemented Sage Intacct eight years earlier at NTT Testing, Velazquez Maynard knew what was possible. This time, the implementation was even faster. “We implemented everything within two to three months,” she confirms.

The team kept it simple, using core Intacct functionality rather than trying to do too much at once. “We wanted to get everything in there. We got all the basics in flowing well first, and then we looked at adding purchasing and other things that may be available to us,” Velazquez Maynard explains.

The transformation wasn’t without challenges. Legacy invested in EMRConnect to pull financial and statistical data from PointClickCare into Intacct, hoping for complete visibility through dashboards and reports. Unfortunately, that integration hasn’t delivered as promised. “The most we’re getting out is basically journal entries coming over,” Velazquez Maynard admits. “That’s probably been our only challenging point throughout the integration.”

Despite this setback, the core implementation delivered immediate wins. Within months, Velazquez Maynard created custom floor spending reports that transformed how Legacy manages compliance. “It’s an easy report that we can look at every single month. And we do. We analyze it,” she says. “Each quarter, we’re able to make informed decisions on staffing.”

Life-Changing Automation

The most dramatic improvement came from Sage Intacct’s handling of inter-entity transactions. What once required hours of manual entries and reconciliation now happens automatically in the background.

“One thing that was life changing for us was the way that Sage Intacct handles due-to/due-froms in the background,” Velazquez Maynard shares. She still reminds her accountants they don’t need to create these entries manually. “Sage does it for you. It handles it all for you. Just put it in and pay it and call it a day.”

Legacy created targeted dashboards for facility administrators, the people Velazquez Maynard describes as “on the front line every single day trying to run those buildings and running in circles.” These administrators now see their facility’s financial performance in real-time, allowing them to fix issues before month-end close.

The dashboards help administrators review accounts payable, correct miscategorized expenses, and monitor budgets as things happen, not after the fact.

The finance team itself is lean—just two main accountants (a senior and staff accountant), an AP team, and the executive leadership. This small team now manages complex financial operations that previously consumed far more resources.

Building an Integrated Tech Stack

Sage Intacct’s integration capabilities allowed Legacy to build a comprehensive financial ecosystem. They use SmartLynX for scheduling (critical when labor is their biggest expense), iSolved for payroll and HR, and Divvy for credit card management.

“What Sage Intacct does really well. is integrating with other software, and there is always some kind of solution that they can find you,” Velazquez Maynard notes. If Intacct doesn’t have what you need, “there’s someone out there that can team up with Sage and it can become part of the platform that will make you a winner.”

The Real Cost of Standing Still

When asked about advice for other healthcare finance professionals considering modernization, Velazquez Maynard is direct: “They can’t be afraid of the cost, because in all reality, the cost of not doing it is probably greater.”

She points to the hidden expenses of staying on legacy systems. “The hours that are going to be spent by your CFO, controller, and accountants trying to do manual things or in Excel that could be automatic—it’s going to end up paying for itself.”

For organizations worried about implementation complexity, Velazquez Maynard offers reassurance. The implementation partners “point you in the right direction. They tell you step by step what you need to do.”

Looking ahead, Legacy faces the same challenge Velazquez Maynard identifies as healthcare’s biggest issue: the labor force. “Finding good labor is hard,” she admits. The company regularly evaluates wage scales, trying to determine if higher pay will attract better talent or if they’re “just throwing money at something.”

With facilities sometimes forced to use agency staff at $55-65 per hour, having clear financial visibility through SmartLynX metrics helps them better control these costs. “You have to be staffed. So sometimes there’s just nothing you can do.”

Lessons for Healthcare Finance Leaders

Legacy’s transformation from 30 disconnected systems to a unified platform offers clear lessons for healthcare organizations. The speedy implementation proves that transformation doesn’t require years of disruption. The immediate benefits, from automated inter-entity transactions to real-time floor spending reports, demonstrate tangible returns on investment.

Most importantly, Velazquez Maynard’s experience shows that the right technology enables growth rather than just supporting operations. Legacy continues expanding, confident their financial infrastructure can scale alongside their ambitions. When Velazquez Maynard took the job, she told her boss, “If you’re planning on selling in the next 20 years, I am not taking this job.” With the foundation they’ve built, she might just keep that promise.

For healthcare finance professionals wondering if transformation is worth the effort, Velazquez Maynard’s journey provides a clear answer. The question isn’t whether you can afford to modernize; it’s whether you can afford not to.

Listen to the complete conversation with Velazquez Maynard on The Unofficial Sage Intacct Podcast to hear additional insights about managing multi-entity healthcare organizations, building effective financial teams, and navigating the unique challenges of the nursing home industry.

From OnlyFans Audits to AI Cheating Scandals: Inside Accounting’s Strangest Week Ever

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In episode 465 of The Accounting Podcast, hosts Blake Oliver and David Leary tackle one of the most bizarre unintended consequences of recent tax legislation: IRS agents may soon need to review OnlyFans content at work to determine if digital creators qualify for tax deductions. This absurd scenario perfectly captures the chaos unfolding as artificial intelligence and new regulations collide with traditional accounting practices.

The IRS’s Awkward New Job Requirement

The new “no tax on tips” deduction allows digital content creators to deduct up to $25,000 from their taxes. But conservative groups successfully lobbied to exclude “pornographic activity” from this benefit, leaving the IRS to determine what qualifies as pornography—a definition the Supreme Court has never clearly established.

“Are IRS agents going to have to sit in their offices at work and look at OnlyFans accounts and determine whether or not this content qualifies?” Blake asks. “Supreme Court Justice Potter Stewart famously said, ‘I know it when I see it.’ So that’s my question.”

The timing couldn’t be worse. The IRS just closed hardship telework requests, forcing employees back to the office while the agency faces a backlog of over 8,000 accommodation requests and has lost 25% of its workforce through voluntary separations this year.

David raises another complication: “If somebody did one video that got determined to be pornographic, do you lose the whole deduction or can you claim all the other days that you got tips?”

Tax professionals face their own dilemma. “Let’s say you get a client who says they want to claim the tips deduction, and they’re an online creator,” Blake explains. “Are you going to check out the content and decide whether it qualifies?”

When AI Meets Ethics—The KPMG Scandal

While the IRS grapples with content moderation, KPMG Australia is dealing with its own technology-related embarrassment. Multiple auditors were caught using AI and group chats to cheat on mandatory compliance training during 2023-2024. This happened after KPMG had already paid a $50 million fine for exam cheating from 2015-2020.

“AI is really good at taking these kinds of tests,” Blake notes. “Just copy paste all the questions into ChatGPT and you’ll pass in a heartbeat.”

The consequences were light: formal warnings for most, one verbal caution, and one person who left months later. The firm didn’t report the incident to regulators.

“They got fined $50 million for it before and then they just continued to do it,” David points out. “So the fines don’t work, obviously.”

The PCAOB is now warning it will closely scrutinize AI use in accounting firms. They’re particularly concerned about private equity-backed firms, fearing pressure for short-term results will compromise audit quality when combined with AI automation.

The Death of the Billable Hour

Beyond scandals, AI is reshaping how accounting firms operate and charge for their services. The billable hour, introduced in the early 1900s as a management tool and dominant since the 1960s, faces extinction.

“When AI can review thousands of contracts in minutes instead of weeks, charging for time spent becomes economically absurd,” writes Rita McGrath of Columbia Business School in the Wall Street Journal.

Blake experienced this transformation firsthand as a freelance bookkeeper. “I billed hourly for keying transactions into accounting software. I then figured out how to automate 90% of it. I had a choice: bill 80-90% fewer hours and lose all my revenue, or switch my clients to fixed fees and take ownership of the process.”

The efficiency gains are already here. Ramp has AI approvals handling 80-90% of transactions automatically. Xero’s new auto-reconcile feature uses AI to match transactions with high confidence. According to OpenAI’s survey of 9,000 workers, employees save an average of one hour daily using AI, with heavy users saving ten hours weekly.

But not every company succeeds at this transition. Pilot raised $118 million at a $1.2 billion valuation, betting it could automate bookkeeping and achieve software margins. Today, they have just 2,500 clients and recently launched a partner program to offload the labor they couldn’t eliminate.

“The fact that they’ve launched a partner program indicates they’re trying to push labor costs out of the company so they can be a software company,” Blake observes.

The irony isn’t lost on David. “They have this headline, ‘Tired of endless QuickBooks updates breaking your workflow.’ But the very first app they list in their integrations is QuickBooks. It’s built on QuickBooks.”

AI Writing Reports Nobody Trusts

Companies are racing to use AI for financial reporting even while harboring deep doubts about its reliability. Twenty-eight percent of financial executives already use generative AI for external reporting. ON Semiconductor’s AI writes entire sections of management discussion and analysis. Hewlett Packard Enterprise plans to use AI for first drafts of financial statements starting in January.

“Take financial statements, drop them into ChatGPT and ask for the narrative. It does a spectacular job,” Blake says. “Taking numbers and turning them into a story that non-accountants can understand, highlighting what’s important, it’s really good at that.”

Yet Harvard Business Review’s survey of 603 business leaders shows only 6% of companies trust AI for core business processes. Most limit AI to low-risk or supervised tasks.

“The work accountants do requires near 100% accuracy,” Blake explains. “Research shows AI achieves 80% accuracy at 30-minute tasks but 100% only for tasks taking a few minutes.”

Meanwhile, Meta’s creative accounting for its Hyperion data center—using complex structures to keep it off-balance sheet—shows human financial engineering still outpaces AI. As the Wall Street Journal called it, “Artificial intelligence, meet artificial accounting.”

What Comes Next

Interesting research is challenging assumptions about what drives audit quality. Studies show offices with less competition deliver better audits with fewer errors. “Competition pushes down fees, which incentivizes auditors to cut corners,” Blake explains.

Another study found audit teams with more women deliver higher quality at lower fees, but only in supportive environments with good work-life balance and female partners.

President Trump, meanwhile, claims tariff revenue will eliminate income tax entirely. “We’ve taken in literally trillions of dollars,” he stated, though actual tariff revenue was only $258 billion last year versus $2.7 trillion from income taxes.

“Doesn’t anybody prep him?” David wonders. “He just makes up numbers.”

The accounting profession is at a crossroads. Will accountants become the quality control layer ensuring AI meets professional standards? Or will they cling to outdated models until technology makes them irrelevant?

To hear Blake and David’s full discussion, including details about the new Trump IRA accounts for kids and Senator Jim Justice’s $5 million tax settlement, listen to episode 465 of The Accounting Podcast.

Your Excel Data Never Leaves Your Computer With This AI Automation Method

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While 58% of professionals have tried AI, only 17% use it regularly. Kyle Ashcraft sees opportunity in that gap.

In episode 108 of the Earmark Podcast, host Blake Oliver sits down with Kyle, a CPA who built Maxwell CPA Review and helped over 1,500 students pass their exams, for a live demonstration that might change how you think about Excel automation. Their conversation shows how any accounting professional can start automating their work in under an hour. No coding experience required.

The AI Gap Nobody’s Talking About

“The more advanced AI becomes, we can take one of two directions,” Kyle explains during the demonstration. “You can continually veer away from it, and the more that comes out, you step farther and farther away from it. Or you can make it a goal to learn, let’s say, one new tool a week.”

The problem isn’t that accountants don’t want to use AI. It’s that they don’t have dependable strategies for implementing it. Kyle describes the typical approach as, “Opening up ChatGPT, throwing in a spreadsheet, and then giving it a prompt and seeing what it comes up with. Sometimes like a Hail Mary, where you just want to see if it gives you an acceptable output.”

There are two major issues with this approach. First, it often takes multiple attempts to get the output you want because ChatGPT can’t read your mind. Second, and this is crucial for accountants, when you upload a spreadsheet to ChatGPT, “your Excel document is going directly to OpenAI. Your prompt is going to them, and the prompt that they output to you is going to them as well.”

This matters because OpenAI’s data retention practices are questionable at best. They’re currently in a lawsuit with The New York Times and required to permanently retain logs. No wonder 70% of accounting professionals cite data security as their primary concern with AI adoption.

Enter “Vibe Coding”: When Everyone Becomes a Developer

Kyle’s journey started with a challenge. Could someone with zero coding experience build something that traditionally required a development team?

Four months later, he had his answer. Using Cursor, ChatGPT, and Claude, he built a complete assessment platform that identifies students’ weakest areas, emails follow-up practice materials, and provides analytics dashboards for professors. All with no programming background whatsoever.

“This really shows it’s possible to not have any idea what the code itself is saying, but with clear communication and patience, you can accomplish things that would have been impossible just two years ago,” Kyle tells Blake.

This phenomenon has a name: vibe coding. It’s coding without being a coder, using everyday language to generate complex scripts. During the demonstration, Kyle shows how Cursor generates hundreds of lines of Python code based on simple English instructions. You don’t need to understand what those lines mean, you just need to know what you want to accomplish.

Kyle offers a metaphor that reframes the entire relationship with AI. “Picture it like an orchestra and a conductor. You’re the conductor. You are in control. You set the tempo. You set the vision of what you want to achieve. And it’s the orchestra that’s doing all of the hard work.”

“There’s this assumption that AI is going to eliminate a lot of work,” Blake observes. “But what we find in reality is that it shifts the work from doing to reviewing. So that job is not going away, but now we review the output and provide feedback.”

The Script Solution: Privacy and Reliability in One Package

During a live Q&A, one attendee asks the question on everyone’s mind: “When you load the project into Cursor and it shows you the Excel files, does this AI platform not retain that client data? How is this different than uploading the Excel into ChatGPT?”

Kyle’s answer reveals why scripts are game-changing for accounting work. “It does not retain this data because with this process, it created this Python script, which is just Python code. It’s offline. There’s no record of this script.”

Your Excel data never leaves your computer. Instead, AI creates a script—basically a recipe—that runs locally on your machine. Think of it this way: instead of handing your sensitive client data directly to an AI company, you’re asking AI to write you instructions. The AI writes the instructions based on your request, but it never sees your actual data.

Blake highlights another advantage: “When Cursor communicates with AI services like Claude, it does so through APIs that have zero data retention policies. That’s in stark contrast to the chat interfaces most people use.” As he explains, these companies want large enterprises to be comfortable, so API interactions have much stricter privacy protections.

But privacy is only half the equation. Scripts also solve the reliability problem. Blake shares a cautionary tale about a Big Four firm in Australia that had to refund a government contract because its AI-invented citations didn’t exist. “They send an entire report to the government, the government clicks on the links for it, and they don’t exist. It’s disastrous if you don’t actually review the output.”

When another attendee asks about the risk of hallucinations, Kyle explains why scripts are different: “You’re not having an AI model interact with the Excel information. You’re having this step-by-step script that says, ‘do an auto sum of column B.” The script uses Excel’s own functions, it just automates the clicking and typing you’d normally do manually.

This deterministic nature means the same script produces the same result every time. As Blake notes, “We can reuse the script we created, apply it to a new Excel file and get the same expected result without having to check everything over again.”

The Three-Part Formula That Makes It All Work

“Goal. Steps. Output.” With these three words, Kyle unlocks the secret to making AI do exactly what you want.

During the demonstration, he tackles three real-world Excel challenges that every accountant faces. First up: a messy data export with empty rows, headers in row three, 14 different date formats, and inconsistent spacing.

His prompt is elegantly simple:

  • Goal: Clean up this Excel file
  • Steps: Identify any inconsistent formatting. Add basic color and style. Analyze each column to better understand its format
  • Output: A new Excel document

Within moments, Cursor generates hundreds of lines of code. The result is a perfectly formatted table with consistent dates, proper headers, and professional styling. “It looks clean, smooth, with some nice shading,” Kyle observes. “It’s just easier to look at overall.”

When Blake asks whether Cursor can do its own checksum, they quickly add both files and ask Cursor to verify nothing was lost. The response: “All 20 transactions are present. All amounts were correctly processed. The sum of $19,000 is maintained.”

The second demonstration scales up the complexity. Kyle shows a General Ledger detail export with 400 rows spanning every account. Manually organizing this would require hours of filtering and copying. His structured prompt creates a summary tab showing account codes, transaction counts, debits, credits, and net amounts, plus individual tabs for each account’s detailed transactions.

“Instead of going to each account in your accounting system and exporting the GL individually, just export all the accounts together and then run this through,” Kyle suggests. What might take an hour completes in under a minute.

The third example addresses bank reconciliation, comparing statements to GL detail to find discrepancies. No more scrolling row by row. The automation identifies matching items, missing transactions, and differences between the files instantly.

Blake connects the dots for viewers. “I picture our listeners who work with some older ERP systems that don’t have very customizable reporting and who are doing a lot of manual formatting. Now you can automate that recurring task every month or every week.”

Getting Started Is Simpler Than You Think

The transformation begins with two downloads that take five minutes each. First, download Python, then download Cursor. Start with the free tier. Kyle uses the $20 monthly plan for daily use, but the free version is powerful enough to begin.

When you first open Cursor, it will ask you to install some packages like “pandas” for Excel interaction. Kyle recommends, “Click the dropdown button and choose ‘run everything’ so you trust the platform. It’s very reliable, and then anytime it needs a new required package, it automatically downloads that.”

Don’t forget to adjust your privacy settings. In Cursor’s settings menu, scroll to privacy options and select “privacy mode” with “no training data used.” This ensures your work isn’t incorporated into AI training datasets.

The key to success is to start small and be patient. “Try it with some information that is not private at all, maybe one of your own documents,” Kyle suggests. “The more patience I have, the more I follow up on that review step by giving it tiny pieces of feedback, the more it improves over time.”

Blake adds perspective on managing expectations: “When I try new tech, 80% of what I do doesn’t have a payoff, but then the 20% has a huge payoff. So don’t get discouraged if your first few attempts fail.”

For recurring tasks, the payoff compounds quickly. “Private roles always have month-end closing. Public end clients always need amortization and depreciation schedules for their notes,” Kyle notes. Even creating client checklists based on prior year information becomes a candidate for automation.

The Bottom Line: Your Move

The tools are accessible. The knowledge is available. As Kyle demonstrated with live examples, you can go from messy data to polished reports in minutes using nothing more than clear English instructions.

So, will you step away from AI as it advances, or learn one new tool at a time and stay connected to this movement? Because as Kyle reminds us, “It’s not going to go away. It’s just going to become more integrated into everyday work culture.”

To hear these demonstrations in action, listen to the full episode at podcast.earmarkcpe.com/108. Kyle has also offered to help early adopters, so reach out to him at kyle@maxwellcpa.com with questions or to brainstorm how this could apply to your specific work situation.

As Kyle challenges at the session’s close, “Try your first task with it this week and see how it works for you.” The revolution in accounting work is here, waiting for those bold enough to embrace it.