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Earmark Team

QuickBooks Online Tags Retiring May 15: How to Migrate Your Data Now

Earmark Team · April 24, 2025 ·

QuickBooks Online users who rely on the Tags feature are facing a critical deadline. After May 15th, 2025, you’ll no longer be able to add new tags to transactions. This underused but flexible feature is being replaced by a modified Custom Fields alternative that comes with both benefits and limitations.

In a recent episode of The Unofficial QuickBooks Accountants Podcast,  hosts Alicia Katz Pollock and Dan DeLong discussed this major transition and explained what you need to know and do before the deadline.

Why Tags Are Going Away (And Why Some Users Will Miss Them)

According to Alicia and Dan, about three-quarters of QuickBooks users never used Tags at all. As Dan explains, “When they roll out a new feature, if it doesn’t get used, it could stand to be discontinued. When I worked there, typically we wouldn’t find out who used it until we stopped it… and then people would call in droves, like, ‘What are you doing? I was using that!’

But for those who discovered Tags’ flexibility, this retirement is a significant loss. Alicia shares several creative ways professionals used Tags:

  • Marking transactions that needed review: “I would use a tag that said ‘for review.’ And then I could pull up all the transactions that needed review, and boom, they were all right there.”
  • Weather tracking at a gas station: “They used tags to say what the weather was… Is it sunny? Is it raining? Because their business is lower on rainy days, and that helped them filter out weather anomalies.”
  • Animal categorization at a veterinary practice: “They would tag transactions with cats, dogs, birds, rodents and reptiles and then they could see who they were providing their services for.”

Tags were particularly valuable for users on lower-tier QuickBooks plans who didn’t have access to Classes or Locations features. “If you didn’t need any of the other features in Plus,” Alicia explains, “Tags allowed you to get flexible about it.”

The Migration Timeline: Act Now

The retirement process follows this timeline:

  • March 17, 2025: Custom Fields was expanded across all QuickBooks Online subscription levels
  • May 15, 2025: CRITICAL DEADLINE – After this date, Tags become read-only
  • May 16, 2025 – May 14, 2028: During this period, you can view historical Tags and run reports but can’t add new tags
  • May 15, 2028: Complete removal of Tags functionality and all historical data

How to Migrate Your Tags to Custom Fields

If you’re using Tags, here’s what you need to do before May 15th:

Step 1: Make sure all your transactions are properly tagged. Go to the gear icon, select Tags, and click “see all untagged transactions” to catch any missed items.

Step 2: Click the “migrate tags to custom fields” button in the Tags section.

Step 3: During migration, you’ll need to:

  • Choose which tags to include (uncheck any you don’t want to migrate)
  • Name your new Custom Field (it defaults to “Tags”)
  • Specify that the field applies to transactions (recommended)
  • Select which transaction types should display the field
  • Decide whether the field should print on customer-facing forms

Step 4: Complete the migration. Your Tags will convert to a dropdown Custom Field with up to 100 options. If you have grouped tags, they’ll appear as “Group Name: Tag Name” in the dropdown list.

Dan notes an important distinction: “The historical transactions still have the tags on them. The new transactions won’t have the tag field – they will have the custom field available to choose.”

Critical Step: Preserve Your Historical Data

This migration doesn’t transfer your historical tag data to the new Custom Field – it only creates the structure for future transactions. Your 2025 reports will be split between the two systems.

“Run your reports on all of your tags so that you have that history permanently,” Alicia emphasizes. “When you’re looking at the Tags list, every single tag group or ungroup tag has a ‘run report’ link to the right of it.”

Save these reports as PDFs with multiple date ranges. “This is the very last time you are ever going to see a P&L related to this data,” Alicia warns.

What’s Better and What’s Worse in the New System

Improvements:

  • Universal Availability: Custom Fields are now available across all subscription tiers.
  • Increased Fields: Simple Start and Essentials now have one custom field, Plus gets four, and Advanced continues with twelve.
  • Dropdown Functionality: The new custom field is a dropdown, which “helps eliminate data entry errors,” as Dan points out.
  • Form Flexibility: Unlike standard custom fields, this new one works on both sales forms AND expense forms.
  • Printing Options: You can choose whether to display the field on customer-facing documents.

Limitations:

  • No P&L Reporting: “The big heartache is that you cannot do a profit and loss report by custom field,” Alicia explains. This is a major functional loss for many users.
  • Banking Feed Limitations: “You cannot apply this new custom field from the banking feed,” notes Alicia. You’ll need to edit transactions after they’re created.
  • No Multiple Values: Unlike Tags, you can only select one value per Custom Field on a transaction.
  • No Bulk Assignment: Currently, there’s no way to apply Custom Fields to multiple transactions at once, though Intuit has said this feature is coming.

Recommendations for Moving Forward

If the Custom Fields approach doesn’t meet your needs, consider these options:

Consider Upgrading: “If you’re angry because your tags are gone, you probably need to be using the right tool for the job anyway,” suggests Alicia. “Classes are way more reportable… It might be worth upgrading to Plus.”

Use Multiple Custom Fields: If you’re on Plus or Advanced, you have access to more custom fields and can create separate fields for different tracking needs.

Spreadsheet Sync: Advanced users can leverage Spreadsheet Sync to manage custom field data, including retroactively applying values to past transactions.

Stay Alert for Improvements: Intuit has already announced that bulk assignment and adding Custom Fields to deposits are on their roadmap.

The Reality Check

As Dan puts it, “If you don’t use something, it is in jeopardy of going away,” bringing new meaning to “use it or lose it” in the software world.

For many users, Tags weren’t even on their radar. But for those who built creative workflows around them, this transition requires immediate action to preserve historical data and adapt to the new system.

If you need help with the migration process or want to discuss this change, you can reach out to Alicia and Dan at unofficialquickbookspodcast@gmail.com.

Listen to the full episode for more details and insights about this important transition in QuickBooks Online.


Alicia Katz Pollock’s Royalwise OWLS (On-Demand Web-based Learning Solutions) is the industry’s premier portal for top-notch QuickBooks Online training with CPE for accounting firms, bookkeepers, and small business owners. Visit Royalwise OWLS, where learning QBO is a HOOT!

QuickBooks Updates: Tap to Pay, Third-Party Integrations, and Training Opportunities for Accounting Pros

Earmark Team · April 23, 2025 ·

In the latest episode of The Unofficial QuickBooks Accountants Podcast, hosts Alicia Katz Pollock and Matthew “Spot” Fulton break down the most important QuickBooks announcements from Intuit’s March “In the Know” webinar. 

Here’s what’s new, from streamlined payment processing to expanded integrations and professional development opportunities.

Upcoming Training Opportunities for ProAdvisors

Here are several important training opportunities that ProAdvisors should mark on their calendars:

Level Two Certification Virtual Conference (March 25-27) – This training offers 9.5 CPE credits and prepares you for the advanced certification that many firms now require. Alicia emphasized, “Level one is like what buttons do you push… Level two is really leveraging the resources, some of the more advanced features, being able to think creatively about how to use the features to solve problems.”

MailChimp Training – Two new trainings are available in the ProAdvisor certification portal: “Getting Started with MailChimp” and a “MailChimp Product Guide” for client conversations. These trainings help ProAdvisors understand how MailChimp (now owned by Intuit) can be used for targeted client communications.

Recertification Window (April 28 – June 30) – The hosts emphasized the importance of recertifying early. “If you certify much earlier, your chances are probably better than later to get that prize,” mentioned Matthew, referring to the weekly $250 gift card drawings for those who pass the test. Remember that ProAdvisor certification tests are open-book!

Construction Industry Training (May 8) – For those interested in the construction niche, Intuit is offering specialized training covering “the modern construction landscape, mapping the construction workflow, connecting field and office, and key technology solutions.”

Tap to Pay on iPhone Eliminates Hardware Requirements

One of the most exciting announcements is the new Tap to Pay feature for iPhone, available in both the QuickBooks Mobile and Go Payment apps. This eliminates the need for the $50-100 Bluetooth card readers that many users didn’t even know existed.

“This is huge,” Alicia explained. “Now all you have to do is pull up the GoPayment, pull up the sale, and all the person has to do is either tap their phone to your iPhone or tap their credit card to your iPhone, and it automatically pays.”

The financial benefits extend beyond hardware savings. Transactions processed through Tap to Pay cost just 2.5% compared to 3.4% for manually keyed entries. ProAdvisors can secure even lower rates for their clients through preferred pricing.

However, both hosts emphasized that the real value isn’t in the processing rates but in the automated reconciliation. “If your focus is on the rates versus the efficiency, then you’re actually paying attention to the wrong thing,” Alicia noted. “QuickBooks Payments has huge ROI because when you run the payment through it, it recognizes it, it pays the invoice, it puts it in undeposited funds, it batches the payments and it matches to your bank feed.”

This feature is currently available in the US, with Canada expected to follow later.

Third-Party Payment Integrations Expand

QuickBooks Payments is significantly expanding its third-party integrations, allowing more applications to use it as a payment processor. The growing list includes PandaDoc, ChargeOver, Notify, ServiceM8, Buildertrend, Lightspeed, Salesforce, BigCommerce, and many others.

“Basically, what happens is you go into the settings on these apps for the payment processor, and it’s going to now give you a choice,” Alicia explained. “So instead of just going to Stripe, you will now actually have choices… and QuickBooks will be on the list.”

A major advantage for bookkeepers is how QuickBooks Payments handles processing fees. Unlike other processors that deduct fees from each transaction, QuickBooks extracts fees as separate transactions. “When you see the money in the bank, you’re seeing the full payment on your invoices and they’re all batched at their totals, which makes it much easier for you to batch and reconcile,” Alicia noted.

Intuit is also exploring options to allow merchants to pass processing fees to customers—a feature many professionals have requested.

ProConnect Tax Planning Tools Enhanced

For accounting professionals who handle taxes, ProConnect Tax now offers enhanced integration with QuickBooks. The system allows you to toggle different tax strategies on and off to see how they affect clients’ estimated taxes and tax projections.

“They’re trying to create an environment where it’s more intertwined and you can start to be planning for quarterly estimate payments, better projections, that type of stuff,” Matthew explained.

Users can create multiple “what if” accounts to compare different tax scenarios, view federal and state tax implications, and even print estimated tax payment vouchers. The integration also incorporates Intuit Assist’s AI-powered insights to identify opportunities you might otherwise miss.

QuickBooks Live Expert Service Evolving

QuickBooks Live, Intuit’s $50 support service that allows clients to get simple questions answered, is being refined based on customer feedback. Initially seen as potential competition, many ProAdvisors now view it as a valuable addition to their service offerings.

“I actually now see it as a huge value-added service,” Alicia shared. “I have some of my high maintenance clients calling into it instead [of me].”

The service has important limitations that protect the ProAdvisor relationship: “They’re only answering the question that’s asked. They can’t contribute more information… they can only answer what has been requested of them.”

Intuit is now testing enhancements, including priority queue access and weekend support hours, which could prove valuable during crunch times.

Making the Most of These Updates in Your Practice

These March updates reflect Intuit’s commitment to creating tools that help accounting professionals deliver more value with less effort. For those looking to leverage these innovations effectively:

  1. Focus on efficiency over processing rates when evaluating payment solutions
  2. Consider introducing clients to QuickBooks Live for basic support questions
  3. Pursue Level Two certification to enhance your problem-solving capabilities
  4. Explore specialized training in high-demand niches like construction
  5. Complete recertification early to maximize learning and incentive opportunities

The real value accounting professionals provide goes far beyond basic bookkeeping. These QuickBooks enhancements free up time to focus on the advisory work that truly transforms client businesses.

For more detailed insights on these updates and implementation strategies for your practice, listen to the full episode of The Unofficial QuickBooks Accountants Podcast.


Alicia Katz Pollock’s Royalwise OWLS (On-Demand Web-based Learning Solutions) is the industry’s premier portal for top-notch QuickBooks Online training with CPE for accounting firms, bookkeepers, and small business owners. Visit Royalwise OWLS, where learning QBO is a HOOT!

Selling Your Accounting Firm: Misconceptions, Valuations, and Market Realities

Earmark Team · April 15, 2025 ·

The accounting profession is experiencing a wave of mergers and acquisitions right now, which is forcing firm owners to make tough decisions about their futures. 

In the latest episode of the “Who’s Really the BOSS” podcast, Doug Lewis, the Managing Director at Visionary Group, offered insider insights into accounting firm transactions, drawing from his extensive experience in the field.

Record-Breaking M&A Activity

In 2024, accounting firm transactions set new records, and it looks like 2025 might double those numbers. As Lewis explained:

“2024 was industry-wide across the accounting profession absolutely wild. The pure number volume of transactions that were happening…a lot of people don’t realize how many half-million to $5 million transactions take place almost weekly at this point.”

While big acquisitions by major firms and private equity groups grab headlines, most transactions involve smaller practices that often go unnoticed. This surge in activity is driven by two key factors:

  1. Demographic Reality: The average baby boomer is now in their late 60s, and this generation still owns most accounting practices. Many are discovering that their internal succession plans have either failed or didn’t exist in the first place.
  1. Growth Strategy Shift: Larger accounting firms have increasingly turned to acquisitions as their primary growth strategy. Once firms reach certain revenue levels, relying purely on organic growth simply isn’t enough.

“Once a firm reaches a certain revenue size, it’s extremely difficult to move the growth needle if you’re just focusing on organic growth,” Lewis noted. “The numbers can get staggering on how much new business you have to bring in.”

This creates what Lewis calls a “perfect storm” in the marketplace: Aging owners needing exit strategies are facing off against growth-hungry acquirers who see mergers and acquisitions as their best route to expansion.

Who’s Buying Accounting Firms?

The landscape of potential buyers for accounting firms has changed a lot in recent years. Lewis pointed out three main types of buyers:

  1. Independent Accounting Firms: These firms continue to acquire practices, often opting for equity swaps rather than cash transactions. In many cases, these deals are structured as “mergers,” where the selling partner rolls into the compensation program of the acquiring firm.
  1. Outside Investors: This group includes private equity firms, outsourcing companies, technology firms, and wealth managers who are increasingly getting involved in the accounting space.
  1. Hybrid Firms: These are firms that have already taken on partial or majority private equity investment and are becoming more active in making acquisitions, typically using different transaction structures.

Despite these categories, Lewis emphasizes, “I’ve been a part of hundreds of these things over the years, and I have yet to see two transactions that were ever structured in the exact same format.”

How Firm Valuations Are Changing

It seems like the marketplace is really shifting from revenue-based valuations to EBITDA-based approaches, which align more closely with how other industries operate.

“The overwhelming majority of acquirers are shifting from the multiple of gross revenue down to the multiple of EBITDA, which makes sense because that’s how the majority of other businesses trade,” Lewis explained.

Even with this change, gross revenue multiples still serve as a useful reference point. Lewis noted, “Usually the multiple of gross revenue is always going to hover around that one time mark. Some are significantly higher if it’s a niche profitable practice and some are significantly lower.”

A key consideration in this process is how EBITDA is calculated—especially when it comes to owner compensation. Lewis states, “When we look at EBITDA, the true profitability on a firm, we look at it before any single owner in that company takes home a dime. That’s the starting point.”

This can often lead to tension during negotiations since sellers typically view their compensation as separate from the firm’s profitability, whereas buyers see owner compensation as a cost that needs to be factored in.

Another concept that Lewis brings up is what he calls the “scrape”—essentially the return on investment that buyers require. As Marcus puts it: “If the scrape on a transaction’s 10%, 20%, you have to evaluate this business purchase up against anything else in the market, including just going and sitting that cash in an interest-bearing account.”

Building Value in Your Accounting Firm

If you’re looking to sell your firm or transition ownership, there are some proven strategies that can really boost its value. Lewis identified four key areas to focus on:

1. Develop Your Talent

One of the biggest draws for potential buyers is the talent within your firm. While having younger partners can be a real advantage, Lewis stressed that having strong management at all levels is crucial:

“Young partnership talent is phenomenal to have. But if you have strong managers, that next level director manager level people inside your firm, that’s going to significantly help valuation.”

2. Optimize Your Client Portfolio

Many accounting firms struggle with revenue concentration that goes beyond the classic 80/20 rule:

“It’s not uncommon for us to see more of like a 90/10, 95/5 rule inside accounting firms,” Lewis pointed out.

This means that only a handful of client relationships are driving most of the firm’s value. Lewis shared an eye-opening example: when he asked a seller about their top ten clients, they could only name about five or six and realized they didn’t really know what those clients were trying to accomplish.

Rachel highlighted her own experience: “We were spending a lot of time with very low revenue clients, like multiple touch points on these that spent the least amount with our firm. And it didn’t make any sense.”

3. Review Fee Structures

One of the most effective strategies for increasing your firm’s value is to conduct thorough pricing reviews:

“I’ve yet to really see a firm that has priced themselves out of any market, which is shocking,” Lewis noted.

Despite this insight, many firms hold on to outdated pricing structures that undervalue their services. Lewis recommends that firms “aggressively review your fee structures” and set minimum fee thresholds to get rid of unprofitable client relationships.

4. Highlight Advisory Opportunities

While it may not be realistic for everyone to build strong advisory practices—especially those nearing a transition—Lewis suggests a different route:

“If a firm is a little late in the game to really jump start an advisory department, what they should do is be able to clearly state and identify the advisory revenue opportunities that exist inside their base to a potential buyer.”

Clearly communicating these untapped potential opportunities to potential buyers can significantly boost your firm’s perceived value.

Common Misconceptions When Selling

For firms working on a sale or merger, Lewis says there are two big misconceptions that tend to derail transitions:

  1. Unrealistic valuation expectations often stem from anecdotal information about what other firms received. “When you hear, ‘oh, this firm got a multiple of this’ or ‘private equity wants this in a firm’—yeah, they do, but they want one in a firm that’s 20 times your size,” Lewis explained.
  1. Underestimating transition timelines is another common pitfall. “There are a lot of aging owners out there right now who think that when I’m ready to hang it up, I can just list the thing, sell it, and walk away,” Lewis noted. “Those types of transactions where there is not a relatively extended transition period post-deal—those are becoming less and less commonplace in the market.”

Every Firm Will Face Transition

Lewis’s view is simple: transition is inevitable for every accounting practice.

“Every single firm transacts now. There’s really only three transactions out there. Number one is you’re going to either sell or merge the thing. Number two is you’re going to pull off the internal succession. And number three is you’re going to close your doors.”

This reality completely changes how we should think about firm value. Building value isn’t just something you do when you’re getting ready to sell – these core business principles improve outcomes no matter which path you take.

As Rachel put it: “We need to be doing these things as well if we’re hoping one day that one of our current team members or a future team member is going to want to buy or continue the legacy of our current firms. We need to make them attractive to the people who are working in them as well.”

In today’s red-hot market for accounting firm deals, the winners will be those firms that consistently build value through disciplined business practices instead of waiting until they’re about to transition.

Want to hear more from Doug Lewis? Listen to the episode, and don’t forget to subscribe to “Who’s Really the BOSS” for more insights on building a valuable accounting firm.


Rachel and Marcus Dillon, CPA, own a Texas-based, remote client accounting and advisory services firm, Dillon Business Advisors, with a team of 15 professionals. Their latest organization, Collective by DBA, supports and guides accounting firm owners and leaders with firm resources, education, and operational strategy through community, groups, and one-on-one advisory.

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

Earmark Team · April 10, 2025 ·

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

Earmark Team · April 10, 2025 ·

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.

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