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When Tax Day Was Party Night at the Post Office — And Why AI Is About to Upend Everything Else About Accounting

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Before tax e-filing took over, April 15th was a public spectacle at American post offices. As Blake Oliver and David Leary discussed on their Tax Day episode of The Accounting Podcast, crowds would gather until midnight, with live entertainment, giveaways, and even Playboy offering “stress relief massages” in pink booths. In Philadelphia, there was a “dunk the IRS agent” booth for charity. Radio stations broadcast live. Fast food chains handed out samples. It was America’s weirdest annual party.

Those days are gone — 94% of returns are now filed electronically. But as the hosts explored in this wide-ranging episode, the accounting profession faces disruptions far more profound than the shift from paper to pixels. Within three years, KPMG expects routine audit testing to have “next to no human beings” doing the work. Hobbyist developers are cloning QuickBooks with AI over a weekend. And a third of workers aren’t even checking AI outputs before they submit them.

The IRS Can’t Keep Up — With Rules or Technology

The profession’s struggles with rapid change start at the top. Just five days before the filing deadline, the IRS finalized which jobs qualify for the new no-tax-on-tips deduction. Podcasters made the cut (Oliver and Leary were pleased), along with tattoo artists, ice sculptors, and golf caddies. Accountants didn’t.

“Five days after they finalized these rules to implement them for our clients,” Oliver noted with frustration. The deduction allows eligible workers to exclude up to $25,000 in tips from taxable income, but mandatory service charges don’t count. “This could be the death of the automatic gratuity,” Leary speculated, since those forced tips won’t qualify.

Meanwhile, Americans are spending 11.6 billion hours completing federal compliance forms — mostly tax returns. The value of that labor? Over half a trillion dollars. “That’s material,” Oliver said, noting it represents a significant chunk of the economy devoted to paperwork.

The IRS’s own modernization efforts tell a cautionary tale. The agency had 126 AI projects running as of last summer, up from just 10 in 2022. But after losing 25% of its workforce, 61% of those projects remain unfinished with no plan to close the skills gap. Even more puzzling: the IRS killed its Direct File program despite it costing only $16 million instead of the estimated $61 million and growing 78% year-over-year. “The program was gaining traction and was less expensive than they thought it was going to be, and yet it got canceled anyway,” Oliver observed.

The Big Four’s Radical Restructuring

While the IRS struggles with basic modernization, the Big Four are racing ahead with AI automation that could eliminate thousands of jobs and upend the billable hour model that has defined the profession for decades.

KPMG is moving fastest. They’re piloting AI systems this summer and deploying them next year for routine testing of transactions like payroll, receivables, and cost of goods sold. “Within 2 or 3 years, routine testing could become the first major audit area with effectively no human audit team directly doing the work,” Oliver quoted from KPMG’s audit chief digital officer. “Next to no human beings.”

The other firms aren’t far behind. PwC’s evidence-matching tool now processes 30 client document types, up from six months ago. EY is testing something even more futuristic: AI audit agents that talk directly to client AI agents to gather documents and prepare workpapers. Only Deloitte is publicly pumping the brakes, emphasizing AI should “augment not replace” human auditors.

The numbers are stark: Big Four leaders expect 20-30% of a typical audit to be fully automated by 2029. KPMG UK is already cutting 440 audit jobs. “I don’t see any other outcome than the Big Four just cutting massive numbers of staff jobs,” Oliver said. “If they do this right… that’s 20 to 30% of their billable hours. What are they going to do? Just raise their rates 20 to 30% to compensate?”

Leary had the line of the episode: “Agents are the perfect accounting firm employees. The partners are going to love them.”

The traditional career path is crumbling too. EY’s talent chief told Business Insider that linear career models are becoming “less relevant” as AI values skills over tenure. Oliver speculated firms might shift from hiring masses of new graduates to recruiting experienced professionals from industry, or moving to an apprenticeship model with smaller, more intensively trained classes.

Everyone’s Building Their Own QuickBooks Now

The disruption isn’t just coming from the top. A Reddit user built a full accounting system that runs inside Claude Desktop — no interface, just chat. You tell Claude what happened, and it updates your books. Another developer cloned QuickBooks Desktop using AI, creating a free open-source alternative. The motivation? “I didn’t want to pay for QBO.”

“You as an accounting firm had control over your tech stack and your clients’ tech stack,” Leary explained. “We’re a Xero shop or a QuickBooks shop… Now your clients are just building their own stuff. How do you as a firm manage this now?”

Oliver’s prediction, based on every past tech revolution: “We will end up with more work rather than less, because it will enable our clients to do way more accounting stuff that we’ll have to clean up.”

On the funded startup side, Juno raised $12 million to build AI tax prep that automates 90% of data entry while keeping CPAs in the loop. The key: transparency over autonomy, with source-to-return traceability and visual validation tools. Artifact launched Omni, which Leary called “a Zapier for accounting firms” — it trains AI agents to use your existing tech stack rather than replacing it.

Meanwhile, legacy players are scrambling. Xero published a blog post claiming to be an “AI native operating system.” Leary counted over 20 buzzwords and read them aloud in a devastating list: “AI native, intelligent SaaS, autonomous finance, system of action…” His verdict: “I don’t think this is written for customers. I think this article is written for the street in an attempt to move the stock price.”

The Quality Crisis Nobody’s Talking About

Here’s what should terrify every firm leader: 35% of workers rarely or only occasionally review AI output before submitting it, according to a Resume Now survey. Eighteen percent trust it straight out of the box. Only 40% review AI output every single time. And 15% use AI at work secretly without telling their manager.

“That should scare you as an accounting firm owner,” Leary said.

Oliver argued firms need systems with built-in controls: “If an employee is just generating something with AI… and they didn’t change anything or they didn’t spend any time looking at it, then flag that.”

The stakes are real. The episode covered two fraud cases that show what happens with weak oversight. A New Jersey preparer filed over 100 false returns seeking $170 million in pandemic credits, getting $55 million before being caught. A Pennsylvania preparer started a new $5.5 million fraud scheme while still on supervised release from a previous conviction.

What Separates Winners from Losers

A Hinge Marketing study of 133 firms revealed a massive performance gap emerging. High-growth firms are growing at 33% annually versus 9.6% for average firms. The difference? High-growth firms spend 9% of revenue on marketing (versus 5% for others), and over 90% use AI for content creation, automation, and research.

“If you have a firm that’s growing at 10% and you want it to grow at 30%, spend 10% of your revenue on marketing,” Leary summarized, though Oliver questioned whether it’s causation or correlation: “Is it just that the firms that are growing really fast have money to burn on marketing?”

The Reckoning Is Here

The accounting profession has always adapted slowly. As Leary noted, “Just ask Xero how it takes decades for them to barely make a scratch into the QuickBooks world.” But this time feels different. The changes are coming from every direction at once — Big Four automation, bedroom coders, funded startups, and clients building their own systems.

The irony is thick. Even as AI promises to make location irrelevant, EY is requiring US tax staff to work in-office 12 days a month. The IRS has 126 AI projects but can’t finish them. Firms are adopting AI while a third of workers don’t even review its output.

For firms willing to invest, experiment, and build proper controls, the opportunity is massive. For those hoping to wait it out, the message from this episode is clear: the profession that gathered at post offices until midnight to file paper returns is gone. The question isn’t whether AI will transform accounting — it’s whether the profession can maintain its core promise of trustworthiness while everything else changes around it.

To hear the full discussion — including the story of a disgruntled worker who burned down a $500 million Kimberly-Clark warehouse over pay disputes — listen to the complete episode of The Accounting Podcast.

These S Corp Election Mistakes Create Years of IRS Problems

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A sole proprietor registers a brand-new LLC, reuses the EIN from their old payroll account, files Form 2553 with an effective date of January 1 (months before the entity even existed) and waits for the IRS to bless the election. What they get back instead is a mess: a new EIN they didn’t ask for, returns filed under the wrong number, and IRS notices piling up about unfiled 1120-S returns. It’s the kind of procedural train wreck that Jeremy Wells, EA, CPA, sees regularly in practice, and it’s entirely preventable.

In this episode of Tax in Action, Jeremy breaks down the S corporation election from start to finish, including the eligibility requirements, the precise mechanics of Form 2553, the framework for late election relief under Rev. Proc. 2013-30, and the analytical rigor required before recommending the election in the first place. The episode is a direct response to the flood of oversimplified S corp content circulating online, much of it from influencers who reduce a major business decision to a single rule of thumb about income thresholds.

In reality, the S corporation election decision is loaded with procedural traps and downstream implications that demand careful analysis. Tax professionals who understand the mechanics of making the election and the full range of factors that determine whether it’s actually beneficial serve their clients far better than those chasing shortcuts.

The episode walks through the procedural mechanics of making the election, the common mistakes that derail it, how late election relief actually works, and what practitioners consistently get wrong about it. Finally, Jeremy digs into why the decision to elect S demands analysis that goes well beyond self-employment tax savings, including ownership structure, balance sheet consequences, QBI deduction impacts, and state and local taxes that can wipe out any benefit entirely.

Getting the election right: The procedural traps that create lasting problems

Before evaluating whether the S election makes sense for a client, you need to know how to actually make it correctly. The requirements look straightforward on paper. In practice, several mistakes can cause problems that last years.

Eligibility

The entity must be a domestic corporation or domestic eligible entity under IRC §1361(b)(1). It can have no more than 100 shareholders, although Jeremy notes he’s never worked with an S corp that came anywhere close to that limit. The overwhelming majority have one, two, maybe three shareholders.

Shareholders must generally be individuals, though certain estates, trusts, and organizations can qualify. Jeremy warns that including an S corp interest in an estate plan can be tricky. There’s a serious risk of inadvertently terminating the election when a trust or estate steps into a deceased shareholder’s place. No shareholder can be a nonresident alien. Basically, shareholders need Social Security numbers.

The eligibility requirement that actually blows elections in practice is the single-class-of-stock rule. An S corporation cannot have shareholders with differential rights to distributions. Voting differences are fine—you can have voting and non-voting shares. However, you can’t have distribution waterfalls, preferred stock arrangements, or any structure in which some owners receive distributions before others. That’s partnership territory. Jeremy points out this issue has been litigated repeatedly in tax court and district courts, with businesses forced to choose between their own governing documents and tax law. The S election usually loses.

The check-the-box shortcut most practitioners still get wrong

Jeremy emphasizes this requirement because many practitioners misunderstand it. An LLC electing S does not file Form 8832 separately. When an LLC files Form 2553, it triggers two simultaneous deemed elections. First, classification as an association (which defaults to C corporation status), and then S corporation treatment. Both happen instantaneously. “Do not file Form 8832 to elect a C corporation first, and then file the 2553. Just file the 2553 to elect S,” Jeremy says. 

Filing both confuses the situation and makes a mess. The only time you file Form 8832 for an S corporation is when the entity is revoking its S election and wants to revert to its default classification as a disregarded entity or partnership. Jeremy covers that process in episode 15, Breaking Up with Your S Corp Part Two.

Timing matters, and there’s no extension

Taxpayers must file the election by the 15th day of the third month of the taxable year to be effective for the current year. That’s March 15 for calendar-year taxpayers. Miss that date, and the IRS treats the election as effective for the following year. An election effective January 1, 2026, must be filed by March 15, 2026. File it on March 16, and you’re looking at a January 1, 2027, effective date unless you file for late relief.

Form 2553 details that trip people up

Jeremy identifies several issues drawn directly from situations his firm has handled:

  • EIN confusion. Electing S does not require a new EIN for an existing entity. That’s Treasury Regulation §301.6109-1(h)(1). But when a sole proprietor forms a new LLC to elect S, that new entity needs its own EIN. You cannot reuse the sole proprietor’s old payroll EIN. Jeremy describes exactly what happens when practitioners try. The IRS accepts the election but assigns a new EIN. The practitioner then files 1120-S returns under the old number. A couple of years later, the IRS sends notices about unfiled returns because nothing was filed under the EIN the IRS actually assigned.
  • Effective date before the entity exists. The S election effective date cannot precede the entity’s incorporation or registration date. If they formed the LLC in June, the effective date cannot be January 1. Jeremy notes that so many people made this mistake that the IRS printed a caution directly on Form 2553 itself.
  • Wet ink signatures only. Every signature on Form 2553, including the officer’s on page one and each shareholder’s consent on page two, must be wet ink. No e-signatures. Jeremy acknowledges it’s annoying, but his firm has a workaround: provide the form through a secure portal, instruct the client to print, sign, and scan it back using the portal’s smartphone scanner.
  • The shareholder consent grid. Page two requires each shareholder’s name, address, tax ID, shares owned, acquisition date, tax year end, and signature, all under a statement that reads “under penalties of perjury.” That language matters, especially for late elections, where shareholders also declare they’ve reported income consistently with S corp status for all affected years.

Even when practitioners know these rules, sometimes the deadline slips. The question then becomes whether late relief is available and whether practitioners should even pursue it.

Late election relief

Late election relief is one of the most discussed (and most misunderstood) aspects of S corp elections. Jeremy sees widespread misconceptions about the process of making a late election, and about whether practitioners should make it in the first place. Before you file anything late, you need to understand the legal framework and the IRS requirements.

The statutory authority starts with IRC §1362(b)(5), which allows the Secretary of the Treasury to treat a late election as timely when the entity has reasonable cause for missing the deadline. Treasury Regulation §301.9100-1 lets the Commissioner grant reasonable extensions for regulatory and statutory elections, and §301.9100-3 extends that to entity classification elections provided the taxpayer shows they acted reasonably and in good faith, and that granting relief won’t prejudice the government’s interests.

Over the years, the IRS issued various revenue procedures for different types of late elections. Rev. Proc. 2013-30 consolidated them into a single document that now governs late S elections, along with electing small business trusts (ESBTs), qualified subchapter S trusts (QSSTs), qualified subchapter S subsidiaries (QSubs), and late corporate classification elections.

The four requirements you must satisfy

Section 4.02 of Rev. Proc. 2013-30 lays out four criteria, and Jeremy stresses taxpayers must meet all four:

  1. The entity intended to be classified as an S corporation as of the effective date. Jeremy calls this “the most important to really nail down.”You can prove intent through board meeting minutes, corporate resolutions, communications with a tax advisor—anything that demonstrates the entity wanted S corp status even though it didn’t file the paperwork on time. The problem is most small business owners don’t keep these records. If your client doesn’t have formal documentation, look for email exchanges with advisors, meeting notes, or other evidence that the intent existed before the deadline passed.
  2. Request relief within three years and 75 days of the effective date. That gives you roughly three years, one month, and 15 days. This is the general window, although there is one exception, which Jeremy covers later.
  3. The only reason the entity doesn’t qualify as an S corporation is the untimely filing. Everything else, including eligibility, ownership structure, and a single class of stock, must be in order. If there’s an underlying eligibility problem, late relief won’t fix it.
  4. Reasonable cause for the failure, plus diligent action to correct the mistake. Jeremy notes the most common explanation is straightforward: owners simply didn’t understand the paperwork or deadlines until a tax professional advised them. There are no strict criteria for what constitutes reasonable cause, and Jeremy has seen various approaches, some successful, some not. The key is being honest and specific about what happened.

The procedural mechanics

You still use Form 2553 to request relief, but with modifications. Print “FILED PURSUANT TO REV. PROC. 2013-30” in all caps at the top of page one. Most tax software has a checkbox that handles this automatically. Include a reasonable cause statement either on the form itself (there’s blank space on the bottom half of page one) or on an attached separate sheet.

If the S corporation has filed all its 1120-S returns for tax years between the effective date and the current year, attach the completed Form 2553 to the current year’s 1120-S, as long as the taxpayer files that return within the three-year-and-75-day window. If there are delinquent 1120-S returns, file them all simultaneously. Jeremy admits this makes him uncomfortable. “I don’t feel good doing that. I don’t like filing that many returns on top of one another.” But he’s done it, and it can work.

His firm’s practice is to fax Form 2553 directly to the applicable IRS service center and attach a PDF to the e-filed return. “It can’t hurt to do it both ways,” he says. Just remember, filing Form 7004 to extend the 1120-S does not extend the deadline for the election itself. There is no mechanism to extend Form 2553.

The exception to the time limit

The three-year-and-75-day window doesn’t apply if all of the following are true:

  • The entity and all shareholders reported income consistent with S corp status for the year the election should have been made and every year after
  • At least six months have elapsed since the entity filed its return for the first year it intended to be an S corp
  • The IRS never notified the corporation or any shareholder of a problem within those six months.

Jeremy stresses this last point. Always make sure clients check their physical mailboxes regularly, because the IRS corresponds about S elections exclusively by mail.

If the entity can’t satisfy Rev. Proc. 2013-30’s requirements, the only remaining option is requesting a private letter ruling from the IRS. PLRs can get expensive, and they’re the last resort rather than a routine tool.

Both the officer signing Form 2553 and each consenting shareholder declare under penalties of perjury that the election is true, correct, and complete. For late elections, shareholders also declare they’ve reported income consistently with S corp status for all affected years. This is a sworn statement the IRS takes seriously.

When the S election is (and isn’t) the right call

This is where the internet’s favorite rule of thumb falls apart. The self-employment tax savings that dominate most S corp conversations are just one variable in a multi-factor analysis. Jeremy identifies several factors that can offset or even eliminate those savings.

Stop relying on rules of thumb

The typical logic goes that if you make more than a certain amount (usually some middle five-figure number), you should elect S corporation status. Jeremy calls these rules of thumb “very dangerous” because they omit critical nuance. Yes, the typical purpose of an S corporation is to replace a larger self-employment tax burden with a smaller payroll tax burden. But that single calculation ignores everything else that changes when you make the election.

Review the ownership structure and the operating agreement

S corporations don’t have the flexibility of partnerships. They don’t allow special allocations, differential distribution rights, or waterfalls. The practical problem is that LLC operating agreements are almost always written from a subchapter K (partnership) perspective, not subchapter S. The partnership language baked into those documents won’t translate well for an S corporation. It can set up owners to inadvertently terminate the election.

Jeremy taught a two-hour webinar for the New York State Society of Enrolled Agents on reviewing LLC operating agreements for non-attorneys. He strongly recommends that practitioners request and review operating agreements before recommending any S election. If you’re not already doing this, start.

Examine the balance sheet before you recommend anything

Unlike partnerships, S corporation shareholders don’t get basis for corporate debt, only for bona fide shareholder loans to the corporation. Personal guarantees don’t count. There are no recourse-versus-non-recourse debt considerations like you’d find in a partnership.

Transferring liabilities in excess of assets into the S corporation as part of the §351 exchange—the corporate transfer that happens when an LLC makes that deemed corporate election—can trigger a taxable event. Appreciated fixed assets, especially real estate, create built-in gains issues, and there’s no §754 inside basis step-up available. Jeremy published a detailed post that walks through corporate transfer accounting.

Don’t ignore what happens to the QBI deduction

Owner wages paid by an S corporation are deductible for the business, which reduces qualified business income. That reduction shrinks the §199A qualified business income deduction. Jeremy has seen cases where the QBI reduction offsets most and sometimes nearly all of the self-employment tax savings. “Essentially, it’s a wash.”

The Election Is Easy. The Decision Isn’t

The mechanics of filing Form 2553 may seem straightforward, but the decision to elect S corporation status rarely is. As Jeremy makes clear, the real work is understanding eligibility rules, avoiding procedural traps, and evaluating whether the election actually improves the client’s overall tax picture.

For a deeper walkthrough of the rules, real-world mistakes practitioners make, and the analytical framework Jeremy uses to evaluate S elections, listen to the full episode of Tax in Action.

From Spreadsheets to Raids: What Happens When We Defund Financial Oversight

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Three years ago, Fox News host Greg Gutfeld warned viewers that 87,000 new IRS agents would create a “police state.” Today, armed ICE agents are going door-to-door in Minneapolis without warrants, investigating financial fraud. In other words, doing the work accountants would normally do with spreadsheets and calculators.

“We’ve replaced armed IRS agents with armed ICE agents doing work for the IRS,” says David Leary, co-host of The Accounting Podcast, still trying to process this turn of events. “I’ve lost sleep over this.”

In their latest episode, David and co-host Blake Oliver connect the dots between the 2022 fight over IRS funding and today’s reality in Minnesota, where billions in fraud have led to what they call a predictable but devastating outcome.

Minnesota’s Billion-Dollar Fraud Problem

The numbers coming out of Minnesota are staggering. On December 19th, prosecutors announced charges against more than 90 people across multiple public assistance programs. The fraud schemes read like a criminal playbook: daycares that collected $110 million through fake claims, the Feeding Our Future scandal that stole nearly $250 million in pandemic food aid, autism services billing for work never performed, using unqualified staff, and housing stabilization fraud.

A federal warrant has flagged 14 Medicare programs with significant fraud problems. The potential losses are in the billions.

“This is fraud that has taken place over many years,” David explains. The investigation has been ongoing for a while, but the political fallout came fast. Trump accused Somali immigrants of widespread fraud. A YouTuber documentary filmmaker went to Minnesota and started visiting these daycares, creating viral content that painted Minnesota as corrupt on all fronts.

In response, Trump sent 2,000 ICE agents to carry out what he called “the largest immigration operation ever.”

But here’s where it gets interesting for accountants. As Department of Homeland Security Assistant Secretary Tricia McLaughlin explained on a radio show, “Right now, on the ground in Minneapolis, Homeland Security investigators are going door to door to these suspected fraud sites. It’s daycare centers or healthcare centers and businesses around them as well.”

No warrants. Just agents showing up at doors.

Compare that to what happened just 30 days earlier at Taco Giro in Tucson. ICE and IRS Criminal Investigation spent years building a case, got proper warrants, then executed 16 search warrants as part of their investigation into immigration and tax violations. That’s how law enforcement used to work: investigation, evidence, warrants, then action.

“Raids have replaced audits and guns have replaced spreadsheets,” David observes.

The Time Machine: Back to 2022

To understand how we got here, Blake and David take listeners back to April 18, 2022. As explained in episode 292 of what was then called the Cloud Accounting Podcast, that’s when the IRS was set to receive $80 billion through the Inflation Reduction Act, including funding for 87,000 new enforcement agents.

The political response was fierce. They replay a segment featuring enrolled agent Adam Markowitz, whose tweet went viral and got him attacked on Fox News. Markowitz wrote, “All of my GOP friends who are worried about the 87,000 IRS enforcement agents coming after the little guy. How about just don’t cheat on tax returns?”

Gutfeld’s response on Fox was brutal, calling Markowitz a “schmuck” and warning viewers, “If you have an IQ higher than an artichoke, you must see that by now, this country is heading towards a police state.”

“The police state still happened,” David points out. “We didn’t avoid it.”

The hosts then shared a detail most people missed. In November 2024, a federal judge blocked the IRS from further record sharing with ICE. But the court documents revealed the IRS had already handed over tens of thousands of taxpayer records to ICE, including home addresses. ICE had requested more than one million records from the IRS.

“This might be the reason Billy Long is out,” David speculates about the departed IRS commissioner nominee. “He might have been pushing back on this.”

Following the Money (Or Not)

The pattern is clear to anyone who understands accounting controls. Over the past decade, Congress repeatedly cut the IRS budget while increasing funding for ICE. They shifted from investigation and fines to enforcement.

“Taxes dictate social policies,” David notes. “Budgets also do that. What you fund and budget is what the government is going to do.”

The result is less nonprofit oversight, slower detection of payroll and benefits fraud, and fewer audits. The absence of all those controls that seemed expensive created billions in fraud.

“We’re in the golden age of fraud,” David warns. “Maybe the new Enron is not one company; it’s just billions and billions and billions of small frauds because we’ve cut all of the controls that might catch it.”

Blake connects this to broader economic concerns. According to a Harris poll, 45% of Americans believe their financial security is worsening. Even 45% of Republicans think the economy is in a recession, despite GDP growth of 4.3% in Q3.

“If you’re the president and you don’t want people paying attention to the economy, what do you do?” Blake asks. “You start foreign conflicts or you create internal conflict.”

The Profession’s Own Control Problems

The accounting profession has its own control problem. The AICPA recently proposed major ethics rule changes for firms backed by private equity, worried that outside money could compromise auditor independence.

Under the new rules, firms can’t escape independence requirements by simply creating separate legal entities. If a CPA firm depends on a non-CPA entity for staff and infrastructure, they’re treated as one unit for independence purposes. PE-backed firms also can’t audit portfolio companies in the same fund.

“As CPAs, we stand for independence, objectivity, ethics,” Blake emphasizes. “Nobody else can do audits.”

But existing controls don’t always have teeth. The hosts discuss WH Smith, the historic British retailer. Their audit firm, PwC, missed profit misstatements that cost shareholders 600 million pounds. Yet the board recommended keeping PwC as their auditor.

“An auditor can cost a company half a billion dollars and they keep their contract,” David says, incredulous. “If anyone else failed that badly, you would fire them.”

The Lesson for Accountants

“Everything’s an accounting story,” David insists, and this one hits close to home.

The Minnesota fraud crisis shows what happens when you defund financial oversight. The 2022 IRS debate shows how fear of government overreach led to the exact outcome critics wanted to avoid. The profession’s own struggles with independence and accountability show these patterns repeat everywhere.

“If you have underfunded controls and you don’t have preventive measures, it always shows up as a very big expense,” David explains. “One time it was Enron. Now the expense is humans getting shot.”

Accountants talking to clients about taxes can do their part by explaining where that money goes and why controls matter. Because the alternative—as Minnesota shows—is much worse.

Blake and David dig deeper into these connections in the full episode, including their take on California’s proposed billionaire tax, why wars boost economies, and what Excel championship winners can teach us about efficiency. Listen to the complete discussion above or wherever you get your podcasts.

The Nine Factors That Determine Whether a Business Is Real or Just a Hobby

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Susan Crile spent 25 years as a professional artist. In all but two of those years, she reported losses on her tax returns. When the IRS came knocking with a deficiency notice that could cost her tens of thousands of dollars, they claimed her art wasn’t a real business—just an expensive hobby.

What happened next became one of the most instructive Tax Court cases for understanding how to defend business deductions against IRS challenges.

In episode 16 of Tax in Action, host Jeremy Wells, EA, CPA, breaks down Susan Crile v. Commissioner (Tax Court Memorandum 2014-202)—a case he considers essential reading for anyone working with self-employed clients. As Jeremy explains, “If you work with small business owners, I strongly recommend reading through this opinion.”

When Your Business Becomes the IRS’s Target

The hobby loss rule creates what Jeremy calls a “heads I win, tails you lose” situation for the IRS. Here’s why it’s so devastating for small business owners.

When the IRS decides your activity is a hobby rather than a business, the tax consequences are brutal. “The income from these kinds of hobby, sport or recreational activities is still included in taxable income,” Jeremy explains. “But the reverse is not true. Those losses are not deductible.”

Think about what this means. If you’re an artist who sells $10,000 worth of paintings but spends $25,000 on studio rent, supplies, and marketing, the IRS still taxes that $10,000 as income. But if they say you’re pursuing a hobby, you can’t deduct any of that $25,000 in expenses.

Since 2018, when the Tax Cuts and Jobs Act eliminated miscellaneous itemized deductions (made permanent by later legislation), hobby expenses have been completely nondeductible. You pay tax on every dollar coming in, but can’t offset any dollars going out. The only exception is cost of goods sold (COGS), as the cost of raw materials can still reduce gross income.

The burden of proving your activity is a legitimate business falls entirely on you. Courts won’t just take your word for it. As Jeremy notes, “I can say I’m hoping to make a profit someday, but the courts look at all of the objective factors that go into how I’m operating that activity.”

Who’s at Risk (And Who’s Not)

The hobby loss rule applies to nearly every small business structure: individuals filing Schedule C, partnerships, S corporations, estates, and trusts. But C corporations are completely exempt.

Jeremy points to Amazon as a perfect example. “Amazon was a C corporation pretty much from the start,” he explains. The company famously took seven to eight years before turning a profit. “There was a long time there where investors were nervous that Amazon was never going to be profitable.” Yet Amazon never faced hobby loss scrutiny because C corporations don’t have to worry about this rule.

Simply forming an LLC or electing S corporation status won’t protect you. “Just registering an entity such as an LLC or just making a tax election, such as electing to be an S corporation, doesn’t necessarily guarantee that that taxpayer is not going to have to worry about the hobby loss rule,” Jeremy emphasizes.

For partnerships and S corporations, the determination happens at the entity level, not the individual partner or shareholder level. That affects how losses flow through to individual tax returns.

Susan Crile’s David vs. Goliath Battle

Susan Crile was a tenured art professor at a university when she received IRS deficiency notices in 2010. The IRS was challenging tax years 2004, 2005, and 2007 through 2009—five years where her losses ranged from about $37,000 to $63,000 annually.

The IRS made two arguments. First, they claimed her art activity wasn’t engaged in for profit. Second, they argued that even if it was a business, it should be considered part of her work as an art professor, making the expenses unreimbursed employee expenses rather than business deductions.

Crile believed this was a test case. In an interview after the decision, she said she felt the IRS was exploring “the art industry as a whole to see how far it could go in terms of auditing artists.” Whether that’s true or not, her case established important precedents for creative professionals everywhere.

The Nine Factors That Saved Her Business

The Tax Court uses a nine-factor test from Treasury Regulation 1.183-2(b) to determine whether an activity has a profit motive. Jeremy notes that this framework actually came from earlier court cases. The courts created the test, and the Treasury later adopted it into regulations.

Here’s how each factor played out in Crile’s case:

1. The manner in which she carried on the activity

The court found Crile kept “relatively good records” of sales, galleries, and exhibitions. She worked with a bookkeeper for most years in question. But what really impressed the judge were her business decisions, like switching galleries when she realized her current venue no longer attracted buyers interested in her type of art. The judge concluded, “Petitioner’s marketing efforts demonstrate a profit objective.”

2. Her expertise and that of her advisors

The IRS tried arguing that while Crile could create art, she didn’t understand the business of selling it. The court thoroughly rejected this. The judge found she “understood the general factors that affect the pricing of art: a history of sales, gallery representation, solo exhibits, critical reviews, prestigious public accolades, and she worked diligently to achieve these credentials.” The court’s verdict? “She is, without doubt, an expert artist who understands the economics of her business.”

3. Time and effort expended

Crile spent about 30 hours per week on art during teaching periods and worked full-time creating art the rest of the year. But the court looked deeper, distinguishing between tasks necessary for any activity versus those “essential only because she was conducting a business.” Mundane business tasks like marketing, networking with collectors, and arranging shows would be unnecessary for a hobbyist.

4. Expectation that assets may appreciate

The court recognized that art is “a speculative venture where a single event, a solo show, a rave review or a museum acquisition can lead fairly suddenly to an exponential increase in the prices paid for an artist’s work.” Artists create inventory that might sit at low values for years before that breakthrough moment arrives.

5. Success in other activities

Crile had been an artist for over a decade before becoming a professor. Her academic success actually enhanced her standing with art professionals and expanded her clientele. This factor was relatively neutral in the case.

6. History of income or losses

This was Crile’s weakest point: she had only two profitable years in 25. Jeremy acknowledges “the IRS won this point.” However, the court noted that some losses might have resulted from improperly claiming personal expenses as business expenses. The 2008 financial crisis had also devastated the New York art market during several years under review. Most importantly, the court stated that “losses do not negate the petitioner’s actual and honest intent to profit from the sale of her art.”

7. Amount of occasional profits

With just two years of reported profits, this factor “weighed slightly in favor of the IRS.” But the court remained sympathetic, understanding that in the art world, one breakthrough can change everything.

8. Financial status

Crile had a salary from teaching, but she’d been an artist for over a decade before getting that job. She didn’t become an artist to shield other income from taxes. This factor was neutral.

9. Elements of personal pleasure

The court offered this memorable insight: “A level of suffering has never been made a prerequisite to deductibility.” Yes, Crile probably enjoyed creating art. But her extensive research, marketing efforts, and business operations took her activity “well beyond the realm of recreation.”

The Verdict That Protected Creative Professionals

When the court weighed all factors together, “both qualitatively and quantitatively,” the balance tipped in Crile’s favor. She had proven “an actual and honest objective of making a profit.”

The court found that her activity was indeed a business, allowing her to deduct ordinary and necessary business expenses, and any losses were deductible. As Jeremy summarizes, “Her professional conduct, demonstrated expertise, significant time commitment, and reasonable expectation of appreciation outweighed even decades of losses.”

Clearing Up the “Three-of-Five Year” Confusion

Many tax professionals misunderstand the three-of-five year rule. “I hear this misstated a lot as an activity can’t lose money for three or more years before it’s not deductible,” Jeremy says.

However, that’s not what the rule says. If an activity shows profit in any three of five consecutive years (or two of seven for horse-related activities), it creates a presumption of profit motive. This shifts the burden of proof from the taxpayer to the IRS, but it doesn’t guarantee anything.

“Even if the activity does meet that safe harbor presumption, the IRS can still determine that that activity is not engaged in for profit,” Jeremy warns. Conversely, “an activity can not have profits for more than three years and still be an activity engaged in for profit.”

Practical Lessons for Tax Professionals

Jeremy transforms Crile’s victory into actionable strategies for protecting clients:

  • Document everything. “Documentation and record keeping is key,” Jeremy emphasizes. “Part of the reason Crile was successful is because she had a really good documentation system of her income, expenses, and all the work she produced and her efforts to market that work.”
  • Understand your client’s industry. Jeremy notes how “understanding how the art industry works was key to this case.” Crile brought in expert witnesses to educate the court about art market dynamics. When you can explain why a business operates the way it does within its specific market context, losses become understandable business challenges rather than red flags.
  • Focus on profit motive, not profit. “Having a profit motive isn’t the same as regularly making a profit,” Jeremy clarifies. Don’t scramble to show profitability. Focus documentation efforts on proving business intent.
  • Get to know your clients. Jeremy urges practitioners to understand their clients’ business vision, market strategy, and operational challenges. This ensures “when they go through those periods of losses, you’ve got the ability to make a solid case for them that that activity is, in fact, still engaged in for profit.”

The Human Side of Tax Law

Jeremy finds Crile’s case particularly valuable because it shows “how technical rules and factors at play actually work out in a real life scenario.” Reading the court opinion alongside Crile’s post-case interview reveals “the human side of the story.”

The case made national headlines, with coverage suggesting it protected artists’ livelihoods by confirming their work could be businesslike. But as Jeremy notes, each case is different. “It’s entirely up to the taxpayer to conduct an activity in a professional and business-like manner to avoid the hobby loss rule.”

For tax professionals working with struggling entrepreneurs, such as artists, gig workers, or innovative startups, Crile’s case provides a masterclass in building defensible positions. The tax code, despite its complexity, can accommodate the messy reality of business development when practitioners know how to document and present their clients’ genuine business efforts.

Listen to Jeremy’s complete analysis of this landmark case in episode 16 of Tax in Action. If you work with small business owners, he strongly recommends reading the full Crile opinion to ensure your clients never face the devastating financial consequences of having their business reclassified as a hobby.

When Auditors Look Away and AI Gets Scammed, Who’s Actually Protecting Investors?

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In a recent episode of The Accounting Podcast, hosts Blake Oliver and David Leary tackle the mounting pressures facing the accounting profession, from private equity’s growing influence to corporate lobbying’s impact on tax policy. As the longest government shutdown in history finally comes to an end, the hosts examine how financial incentives reshape both public accounting and tax preparation services.

Government Shutdown Finally Ending After 40+ Days

The episode opens with news that the government shutdown—now officially the longest in U.S. history at over 40 days—is coming to an end. The shutdown cost the economy approximately $15 billion per week, with 650,000 federal employees furloughed without pay.

“The shutdown got real this weekend,” David notes, describing how his wife’s flight was repeatedly delayed, forcing her to abandon her travel plans. The ripple effects have been substantial: the Small Business Administration couldn’t process $2.5 billion in loans for 4,800 businesses, and 42 million Americans on SNAP received only half their November benefits.

Democrats in the Senate broke ranks to vote with Republicans to reopen the government, though they failed to secure an extension of Affordable Care Act subsidies they were seeking. As Blake observes, “It’s a game of chicken. Who’s going to blink first? And Democrats blinked on this.”

The Death of IRS Direct File and Rise of TurboTax Stores

The swift elimination of the IRS Direct File program reveals how corporate influence shapes tax policy. Despite achieving 98% user satisfaction and processing 300,000 returns in its second year (up from 140,000 in year one), the program was axed shortly after Intuit donated $1 million to Trump’s inauguration.

“It really grosses me out,” David says. “Intuit compromised its own values just for the almighty dollar of getting a TurboTax competitor eliminated.” He points out the hypocrisy on both sides. Intuit, one of the first companies to offer same-sex marriage benefits, abandoned its progressive values, while MAGA Republicans embraced a “woke company” once the check cleared.

Treasury Secretary Scott Bessent dismissed Direct File as underused, claiming “private alternatives are better,” despite it being an unmarked pilot program still expanding its reach. As David notes, even 300,000 electronic returns represents “300,000 paper returns the IRS doesn’t have to touch.”

Meanwhile, Intuit announced plans to open 20 new brick-and-mortar TurboTax stores following an “Apple Store model.” Customers will work on their returns at in-store computers, then seek help from CPAs and EAs when needed, what the hosts imagine as an “EA Bar” instead of Apple’s Genius Bar. Combined with 200 additional TurboTax expert offices, Intuit is positioning itself to dominate every segment of tax preparation.

The First Brands Audit Failure: A $700 Million Warning Sign

The collapse of First Brands under BDO’s watch illustrates the potential consequences when private equity interests intersect with audit responsibilities. BDO signed off on financials showing $5.23 billion in debt in March. Six months later, the company collapsed with $11.63 billion in actual obligations—more than double what was reported.

Bankruptcy lawyers accuse founder Patrick James of inflating invoices by up to 50 times to secure fraudulent financing. One $179 invoice was allegedly inflated to $9,271. Over $700 million allegedly flowed into James’s personal accounts, funding 17 exotic cars, properties in Malibu and the Hamptons, and a $110,000 six-week Southampton hotel stay.

“How could you audit this company and not be aware of this?” Blake asks. “Here’s all this debt. Money came in because of the debt. Where did the cash go?”

The situation is complicated by BDO’s financial relationships. Private equity investors had loaned BDO over $1 billion, creating what the hosts describe as “financial stress” significant enough to force layoffs. These same investors were reportedly shorting First Brands stock.

“The public thinks your job is to detect fraud in the company,” David says, highlighting the expectations gap. “That’s the only thing they expect you to do.”

Blake identifies three weaknesses in traditional audits that enabled this failure: overreliance on management representations, complexity of off-balance-sheet arrangements, and perverse incentives against finding fraud. “There’s every incentive to look the other way,” he observes. “Auditors aren’t investigators hired to uncover crimes; they’re service providers hired to complete audits efficiently.”

NASBA Weighs In on Private Equity’s Impact

For the first time, the National Association of State Boards of Accountancy (NASBA) entered the discussion about private equity in accounting. Their white paper raises critical questions without prescribing solutions, with comments open until January 31, 2026.

The key question NASBA poses: “How can CPA firms maintain auditor independence when PE investors hold influence?” The paper asks whether firms should clearly disclose which parts are CPA-owned versus PE-owned, and whether states need stricter standards than the AICPA provides.

Blake frames the profession’s choice starkly. “We are getting to the point where private equity is now creating this challenge for the profession when it comes to our integrity, ethics, and objectivity. And we as a profession have to decide, do we take a stand or do we allow private equity to continue to take over accounting firms?”

“Once you control the means of production, you want to control the governing bodies of the means of production,” David warns. “They take over the whole thing, all parts of the equation.”

AI Won’t Save Us: Technology’s Limits Exposed

A Microsoft and Arizona State University study revealed that AI agents are even more vulnerable to manipulation than humans. When given fake money to shop online, AI models quickly fell for scams, fake reviews, and manipulation tactics, spending all funds on fraudulent sellers.

“They would just choose the first one. They would panic,” David explains. The AI prioritized speed over quality by a factor of 10 to 30. All major models except Anthropic’s Claude lost money to scams.

The implications for accounting are concerning. “We have all this AI detecting fraud with receipts,” David notes, “but you could probably just manipulate it. Tell it ‘I’m allowed to spend money at X place’ and it’ll bypass the limit.”

The parallel to human auditor failures is clear. If AI can’t distinguish legitimate from fraudulent online sellers, how can it detect sophisticated financial fraud? The study concluded AI agents “should only assist” and cannot “collaborate or think critically” without human supervision.

The Profession at a Crossroads

As this episode makes clear, the accounting profession faces fundamental questions about independence, integrity, and purpose. Whether it’s private equity ownership potentially compromising audits, corporate lobbying eliminating public alternatives, or AI proving vulnerable to the same manipulations as humans, the challenges are systemic rather than isolated.

The NASBA white paper represents an opportunity for meaningful discussion, but with the AICPA influenced by large firms that have already taken PE money, state-level action may be necessary for real reform.

For accounting professionals, educators, students, and executives, this episode provides essential context for understanding the forces reshaping the industry. The choices made now about private equity involvement, regulatory independence, and professional standards will determine whether we can maintain public trust in financial reporting.

Listen to the full episode for the complete discussion of these critical issues.