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Archives for April 2025

The Implementation Gap: Why Even Legitimate Tax Strategies Fail During Audits

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What’s the biggest mistake tax professionals make? Great ideas that never get implemented. That’s according to Jasmine DiLucci, a tax attorney, CPA, and enrolled agent who has built an impressive following of nearly 500,000 YouTube subscribers by debunking viral tax myths on social media.

I sat down with Jasmine for a conversation on the Earmark Podcast. We kicked things off by discussing the issue of false information about taxes that spreads on social media. Jasmine also highlighted an even deeper concern: even legitimate tax strategies can face serious issues if implemented incorrectly.

Why Social Media Fuels Tax Misinformation

Jasmine says one reason so many “loopholes” and sketchy strategies go viral is that true tax expertise rarely gets posted online. Skilled professionals are busy running firms, while less experienced creators spread half-truths. This leads to flawed tips on topics like clothing deductions or marking up the inside of a shirt with a tiny business logo, all to claim a tax write-off.

The clothing deduction test is a great example. The test has existed for decades, complete with court rulings stating clothes are only deductible if they’re unsuitable for personal wear. But many influencers ignore this, telling people to slap a hidden logo on their regular clothes. As Jasmine points out, these strategies often fail in an audit. Taxpayers who rely on them risk penalties and extra scrutiny.

Implementation Over Theory: The Real Reason Plans Fail

For Jasmine, the greatest pitfall is the implementation gap—the space between hearing a tax idea, reporting it correctly on a return and documenting what was done. 

She highlights the short-term rental loophole as a perfect example. While the idea is legal, most filers never produce the logs, election statements, or rental agreements proving they qualify.

“If it’s not on the return that way,” Jasmine says, “then what did we just do? Nothing.”

Clients often pay thousands for big-picture “plans” but fail to handle bookkeeping or gather the right records. By the time they’re under audit, there’s no backup for the deduction. Those clients face costly disputes with the IRS, sometimes losing deductions they could have secured with basic documentation.

The Shift in Responsibility: Why Clients End Up Holding the Bag

Misinformation creates tension between clients and professionals. Many taxpayers see social media videos telling them they can write off anything. Then, when their tax expert says “no,” it causes conflict. Some preparers cave and let questionable deductions slide. Others keep warning clients but never clearly explain the “why.”

During an IRS audit, that defense of “my tax preparer said I could” means little. The IRS holds taxpayers responsible for their returns. Jasmine notes that low-level auditors sometimes miss legal details, so a wrong deduction might slip by. But if a client’s case goes to appeals or tax court, illusions fall apart without real support.

Bridging the Gap with an Integrated Service Model

Jasmine’s firm avoids the implementation gap by offering an integrated approach: tax planning, accounting, and preparation, all under one roof. She insists on year-round contact, keeping detailed records, and ensuring clients follow the steps for valid deductions. Her team also handles IRS resolutions, so she knows firsthand where taxpayers slip up.

Working with a single provider can prevent the “blame game.” Instead of paying one person for theory, another for the return, and a third for bookkeeping, Jasmine’s clients get everything in one place. This structure helps them stay organized, meet documentation rules, and rely on correct returns from the start.

Scaling Through Delegation and the Right Tools

While her integrated model works, Jasmine admits it wasn’t easy to build. She did almost everything herself early on—sales calls, tax returns, and marketing. Eventually, she found experts who could handle each function at a high level.

She also credits technology for streamlining processes:

  • Canopy for practice management
  • CCH for tax software
  • Calendly for scheduling
  • Slack for team communication
  • Superhuman for email management

For tax research, she recommends the Bradford Tax Institute because it clearly cites legal authority. She warns that AI chatbots sometimes invent court cases, so relying on them can be risky.

Join Jasmine’s Free Community

Jasmine welcomes taxpayers and fellow professionals to her free tax community at actualtaxlaw.com. There, she shares detailed answers about IRS notices, audits, and new tax updates. Users can post questions or upload documents for possible video reviews.

Earn Free CPE for Listening to the Episode

Tax ideas don’t save you money if you don’t implement them correctly. Closing the gap between theory and execution can shield taxpayers from costly audits and give professionals a clear advantage. Whether logging short-term rental days or documenting a true business expense, proper follow-through matters more than any buzzworthy trick.

If you’d like to hear the full interview and gain more insights on best practices, listen to the full episode of the Earmark Podcast. You can also earn free NASBA-approved CPE by registering for the course on the Earmark app and taking a quick quiz to verify your learning.

How Trump’s Pick to Run Medicare Paid No Medicare Taxes in 2023

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Dr. Mehmet Oz—President Trump’s nominee to lead the Centers for Medicare and Medicaid Services (CMS)—paid no Medicare taxes in 2023 and only negligible amounts in 2022, according to recent reports. 

This revelation from a recent episode of The Accounting Podcast spotlights tax strategies used by wealthy individuals and raises questions about who funds our social programs.

The Limited Partner Exemption: Dr. Oz’s Tax Strategy

At the center of this controversy is a tax strategy known as the “limited partner exemption” to self-employment taxes. Here’s how it works:

Self-employed individuals typically must pay 15.3% in self-employment taxes, which includes 12.4% for Social Security (applied only to the first $168,600 of income in 2024) and 2.9-3.8% for Medicare. Unlike Social Security taxes, Medicare taxes have no income cap, making them a significant consideration for high-income earners like Dr. Oz, whose net worth is estimated between $100 and 300 million.

The limited partner exemption, found in Internal Revenue Code section 1402(a)(13), allows certain individuals to avoid these taxes. As Blake explained, “The provision excludes the distributive share of any item of income or loss of a limited partner as such, other than guaranteed payments from net earnings from self-employment.”

Dr. Oz employed this strategy through his limited liability company, Oz Property Holdings LLC. By classifying himself as a limited partner, he reportedly avoided approximately $440,000 in Social Security and Medicare taxes over the examined period.

“What is a limited partner? It’s ambiguous because the IRS and the Treasury regulations do not provide a clear definition of what a limited partner is,” noted Oliver. This ambiguity creates a significant gray area that can be exploited, especially since these rules were created before LLCs became common in the 1990s.

Democratic staff on the Senate Finance Committee have questioned Dr. Oz’s classification, arguing he couldn’t truly be a limited partner because he was actively involved in his business operations. A recent Tax Court case (Soroban Capital Partners L.P. v. Commissioner, November 2023) rejected the argument that limited partners can never be subject to self-employment tax, instead calling for a “functional analysis” of involvement. However, the court didn’t establish specific criteria for making this determination.

“The court didn’t make this easy and they didn’t establish any test on what a limited partner is, whether you’re actively involved in the business,” Blake observed. “So there you have that gray area that you can exploit like Dr. Oz, to not pay Medicare taxes.”

IRS Enforcement Challenges Amid Workforce Reductions

The Dr. Oz tax strategy story emerges as the IRS faces significant challenges. The Department of Government Efficiency (DOGE), led by Elon Musk, has proposed cutting the IRS workforce by 20% by May 15th—a reduction from earlier rumors of 50% cuts among the agency’s 90,000 employees.

These cuts would eliminate nearly 6,800 additional employees, in addition to the 6,700 probationary employees already let go and 4,700 employees who took voluntary buyouts under the “fork in the road” program.

“We know from years of covering this that every dollar you put into the IRS gets you back $12 in taxes that are going uncollected right now,” explained Blake. “And the tax gap is in the hundreds of billions of dollars a year. So if we actually want to solve the budget crisis, if we want to solve the debt problem in this country, we need to collect revenue.”

Without sufficient revenue agents to pursue complex cases involving high-income taxpayers, questionable tax strategies may continue unchecked. The legal battle over these cuts has already begun, with a federal judge ordering six federal agencies, including the Treasury Department, to rehire probationary employees who were fired last month.

The IRS also faces significant technological challenges. Jeff Johnson, a former IRS employee interviewed by Blake, described an antiquated system in which employees must use green-screen interfaces to access tax information—a tedious process that limits efficiency.

“IRS systems are extremely antiquated,” Oliver explained. “Jeff described having to log into a green screen system where you pull tax information, and it’s extremely tedious. You can print to PDF. That’s about all you can do.”

Blake argued that the solution isn’t simply more personnel: “This is a problem that actually can’t be solved with more people. It can only be solved with modern technology.” More efficient technology could potentially allow fewer agents to conduct more audits effectively.

In another sign of internal conflict, William Paul, the IRS acting chief counsel, was demoted after reportedly clashing with DOGE over sharing tax information with multiple agencies.

Implications for Tax Professionals and Policy

Dr. Oz’s tax strategy raises important questions for accounting professionals and tax policy. The case illustrates how ambiguity in tax law creates opportunities for sophisticated planning that often benefits wealthy individuals.

“Just think about this,” Blake remarked. “How many people are doing this, classifying themselves as limited partners when they’re actually actively involved in the business? Probably lots, because it seems like it’s a fairly easy thing to do because of the gray area involved.”

This ambiguity persists despite the IRS proposing regulations in 1997 that would have formalized the definition of a “limited partner.” These rules were never finalized, leaving a persistent gray area.

The strategy bears similarities to S Corporation compensation planning, where owners must determine a “reasonable salary” to pay themselves, with the remainder potentially exempt from self-employment taxes. Both areas involve significant professional judgment.

Proper documentation is crucial for accounting professionals when employing such strategies. Blake recalled an interview with Jasmine DiLucci in which she pointed out that it doesn’t matter how clever your tax strategy is if you don’t execute it properly. This means having documentation to back up your tax position in case of an audit.

However, the likelihood of IRS challenges to such strategies is directly tied to enforcement capacity. “If you are helping really high net worth individuals avoid taxes, it’s actually great if you have all this ambiguity, and it’s great if you don’t have a lot of revenue agents going after you,” Blake noted.

Perhaps most significantly, Dr. Oz’s case only came to light because of his political nomination. As Blake observed, “I bet you this would never have come to light, and Dr. Oz would never have been audited and asked to pay this Medicare tax, Social Security tax, unless he had become political.”

Unfortunately, scrutiny of tax strategies often depends more on public visibility than systematic enforcement. For every high-profile case that receives attention, countless others likely remain unexposed.

The Tax Strategy Paradox

The irony is striking—someone who avoided Medicare taxes is now nominated to lead the Medicare system. While the strategy appears legal under current tax law, it raises questions about fairness in our tax system.

“I mean, we should be doing this, David. Nobody’s ever going to audit us,” Blake remarked half-jokingly—highlighting how enforcement gaps create opportunities for aggressive tax planning.

For accounting professionals, Dr. Oz’s case offers important lessons about documentation, enforcement realities, and ethical considerations when advising clients on tax strategies. As enforcement resources diminish, professional judgment and ethics become increasingly important safeguards for tax system integrity.

To hear the complete analysis of Dr. Oz’s tax strategy and its implications, listen to the full episode of The Accounting Podcast using the player above or listen here.

PCAOB Board Member Reveals Why 46% Audit Deficiency Rate Is Misleading

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When Senator Elizabeth Warren publicly accused PCAOB Board Member Christina Ho of “downplaying atrocious findings” about audit quality, it got me thinking: Do these alarming statistics about audit deficiencies really tell the full story?

The numbers definitely grab attention: Audit deficiency rates rose from 29% in 2020 to 46% in 2023. These figures from the Public Company Accounting Oversight Board (PCAOB) suggest that nearly half of all audits reviewed contained deficiencies so severe that “the audit firm had not obtained sufficient appropriate audit evidence to support its opinion.” At face value, these statistics paint a troubling picture of the accounting profession.

In a conversation on the Earmark Podcast, I asked Christina to help me understand these numbers. Christina explained the gap between headline statistics and meaningful measures of audit quality.

Understanding the PCAOB’s Role

Before getting into deficiency rates, it’s essential to understand what the PCAOB does. Christina explains, “The PCAOB is responsible for making sure auditors who check the publicly traded companies’ financial disclosures are doing their job well.”

The PCAOB fulfills this mission by registering audit firms, inspecting their work, and enforcing standards through sanctions when necessary. The inspection program represents the largest part of the PCAOB’s operations, with different firms facing different inspection frequencies:

  • The “Global Network Firms” (Big Four plus Grant Thornton and BDO) are inspected annually, with about 50 audits reviewed for each of the largest firms.
  • Firms with more than 100 public company clients are inspected annually, with about 10% of their audits reviewed.
  • Firms with fewer than 100 public company clients are inspected every three years.

The Misleading Mathematics of Deficiency Rates

When the PCAOB announced that 46% of audits reviewed in 2023 contained significant deficiencies, it received considerable attention. In our discussion, Christina pointed out several critical issues with how these numbers are presented and interpreted.

First, these audits aren’t randomly selected. The PCAOB uses a “risk-based approach” that deliberately targets audits they believe are likely to have problems. 

This selection bias fundamentally changes how the statistics should be interpreted. Christina pointed out, “We really can’t extrapolate the deficiency rate to the entire population of all audits because we did not take a statistical sample.”

Even more revealing is what these deficiencies actually mean. Despite the alarming definition, the PCAOB’s own reports include a critical disclaimer that Christina highlighted: “It does not necessarily mean that the issuer’s financial statements are materially misstated.”

In fact, less than 5% of these so-called deficient audits resulted in incorrect audit opinions—the outcome that would truly matter to investors. This stark contrast between the headline figure (46%) and the rate of consequential errors (under 5%) reveals how statistics without proper context can give the wrong impression.

Another significant issue is the PCAOB’s failure to differentiate between levels of deficiency severity. “Our deficiencies… we put everything in the same bucket,” Ho explained. “And in reality, not everything is the same in terms of impact and materiality.”

Unlike internal control evaluations, which distinguish between material weaknesses, significant deficiencies, and minor deficiencies, the PCAOB’s inspection reports do not make such distinctions. This makes it nearly impossible for investors to understand which deficiencies truly matter.

The Disproportionate Burden on Smaller Firms

Christina argued that the current inspection approach unfairly burdens mid-sized audit firms. While the largest firms have a smaller percentage of their audits inspected, firms just above the 100-client threshold face much more scrutiny.

“I personally think that our inspection program is disproportionately burdensome on these firms,” Christina said. This burden is so significant that some firms are intentionally reducing their client base: “They are trying to get rid of their audit clients to get under 100” to qualify for inspections every three years instead of annually.

This creates a troubling situation where firms avoid growth to escape regulatory burden. “I just don’t think it’s good for a very important part of an ecosystem to try to not grow,” Christina said. “We need to make sure we have resilience in the audit marketplace.”

The impact extends beyond individual firms to affect market competition and, ultimately, the capital markets themselves. When mid-sized firms deliberately avoid growth, it concentrates the market among the largest firms—limiting options, especially for smaller public companies.

The Political Fallout

Christina experienced firsthand how deficiency statistics can become political weapons when Senators Elizabeth Warren and Sheldon Whitehouse publicly accused her of “downplaying atrocious findings” after she questioned these metrics in a speech.

“I was very upset about being accused of lying,” Christina told me. “I thought it was very hypocritical of the senators, especially Senator Warren, to essentially bully me because I had a different view from her.”

Rather than reaching out for discussion, the senators sent a letter to the PCAOB Chair, which Christina said left her without “a proper avenue to respond.” This prompted Christina to respond via LinkedIn, where she received significant support from accounting professionals.

This incident highlights how statistics without context can be weaponized in ways far beyond academic disagreements about methodology.

The Search for Better Measures of Audit Quality

Given the problems with the PCAOB’s deficiency rate figures, how should audit quality be measured? Christina suggested several approaches that might be more meaningful:

  1. Look at trends rather than isolated annual statistics. Christina said, “The best way to look at the deficiency rate is not by each year. The best way to look at that data is to be looking at a trend.”
  2. Focus on restatements. Christina said, “Restatements is a much better metric…because that really measures the true impact to investors.” Restatement rates have declined over the past decade, suggesting improvement rather than deterioration in audit quality.
  3. Consider greater transparency. When asked if revealing the names of companies whose audits contained deficiencies would be beneficial, Christina was open to the idea, though she acknowledged the need for broader stakeholder input.
  4. Develop severity ratings. Creating a framework distinguishing between technical violations and substantive errors would provide context for interpreting deficiency findings.

Christina noted that measuring audit quality has been challenging because “audit quality is not quantitatively easily measurable.” And yet, the PCAOB’s approach to deficiencies is to treat all issues identically—regardless of severity or impact.

The PCAOB has been exploring “audit quality indicators” for approximately 15 years but has yet to develop more meaningful metrics. This lack of meaningful data makes it difficult to evaluate the effectiveness of the PCAOB’s oversight or the true state of audit quality.

Has Audit Quality Improved?

Christina believes the PCAOB has helped improve audit quality over the past two decades despite the challenges in measurement. When asked about evidence for improvement, she pointed to declining restatement rates and feedback from audit committee chairs and controllers who report improvements in audit and financial reporting quality.

“If you look at the data on the number of restatements and you look at the last ten, twenty years… restatement has been on the decline,” Christina said. “If you look at the AICPA/CAQ study that they released last year… if you talk to [audit committees], they feel that the audit quality has been improving.”

This more nuanced perspective indicates that, despite the worrying headlines about deficiency rates, the overall reliability of financial reporting might be improving.

Looking Ahead: The Future of Audit Oversight

As artificial intelligence and other technologies transform audits, Christina argues for “a more agile approach” to quality measurement—one that can adapt to technological change and focus on outcomes rather than inputs.

After talking with Christina, it’s clear to me that to move forward, we need to find a balance between regulatory oversight, an understanding of how audits work, and what affects the reliability of financial statements. If we don’t, the profession will get bogged down by misleading metrics that only check compliance boxes rather than enhancing what counts: protecting investors through trustworthy financial reporting.

Want to hear the entire conversation with Christina Ho about PCAOB deficiency rates, audit quality measurements, and her experience with political criticism? Listen to the complete episode of the Earmark Podcast.