Earmark Team

Faith, Fraud, and False Promises: The “Doc” Gallagher Story

Earmark Team · September 8, 2025 ·

“Why are you asking this? Gallagher’s a good man. Gallagher’s a man of God.”

Texas Department of Insurance investigator Steve Richardson had heard a lot in his career, but never this — victims defending the man who had stolen their life savings. Some even warned Gallagher he was under investigation.

These weren’t just clients. They were believers — in Christianity, yes, but also in the gospel of steady returns and risk-free investing. Gallagher preached with the conviction of a Sunday sermon and the polish of a seasoned salesman.

It worked. Over decades, this self-anointed “Money Doctor” convinced hundreds of Christian seniors to hand over more than $20 million. They weren’t chasing Bitcoin jackpots or penny-stock moonshots — just a steady 5–8% a year, “guaranteed,” wrapped in scripture and trust.

In this episode of the Oh My Fraud podcast, Caleb Newquist unpacks how Gallagher used faith, modest promises, and a carefully crafted persona to pull off one of the largest religious affinity frauds in recent memory.

Building the “Money Doctor” Persona

William Neil Gallagher’s life story read like a trust-building checklist. Born in 1941, he graduated from Rhode Island College, served in the Peace Corps, and taught English in Thailand. That’s where he found his faith — a conversion story he would retell endlessly to clients.

Back in the States, he studied to become a preacher, earned master’s degrees in religion and philosophy, and capped it off with a PhD in philosophy from Brown University. The title of his dissertation? The Concept of Blame. (Insert your own punchline here.)

After academia didn’t pan out, Gallagher pivoted to finance, working for Dean Witter Reynolds and A.G. Edwards before striking out on his own in 1993 with Gallagher Financial Group. He positioned himself as a reformed Wall Street insider now serving “regular people.”

His marketing machine ran on Christian radio. As “The Money Doctor,” Gallagher dispensed a mix of vanilla financial advice, market doom warnings, and heavy religious language. He wrote books like Jesus Christ, Money Master and posed for photos with Nolan Ryan, Joel Osteen, and former Texas Governor Rick Perry — props in his carefully curated image.

The Perfect Ponzi: Modest Promises, Maximum Trust

Gallagher’s pitch wasn’t flashy — and that was the genius. His Diversified Growth and Income Strategy Account promised 5–8% annual returns “without risk to principal.” Modest enough to sound realistic, safe enough to lull suspicion.

He told clients their money was in U.S. Treasuries, mutual funds, annuities, and other familiar investments. His sales copy reassured: “When the markets get smashed, our clients lost nothing.”

And he sold himself as more than a money manager — he was their captain. “It’s your ship, but don’t touch anything. My job is to get you safely through the storms.”

Gallagher made house calls, prayed with clients, and sent flowers or fruit baskets when they asked too many questions. One recalled him offering a trip to the Holy Land instead of an account statement.

🚩 Red Flags of Ponzi Schemes

Outdated or missing licenses
Regulatory reprimands on record
Overly personal behavior with clients
Messy office, messy finances
Self-appointed titles (“The Money Doctor”) – often used to create false authority when credentials are lacking

The Red Flags Nobody Wanted to See

Gallagher hadn’t been licensed as a broker since 2001 or as an investment advisor since 2009. Regulators had already reprimanded him in 1999 for falsifying records and misrepresenting his status.

Some clients noticed troubling behavior. One didn’t like how he touched her shoulders. Another saw his Cadillac crammed with loose papers and thought, “That’s not how someone should handle other people’s money.”

When investigators eventually walked into his office, they found unopened mail dating back a decade — and no accounting system.

The Slow-Motion Takedown

The first break came in 2015 when Allianz Life flagged suspicious withdrawals. Texas Department of Insurance investigator Steve Richardson followed the money and found the classic Ponzi pattern: new deposits funding old payouts.

But the case stalled. Victims defended Gallagher, sometimes even warning him about the investigation.

In 2018, James and Carol Herman grew suspicious after Gallagher balked at their $100,000 withdrawal request. Instead of cash, they got gifts — and a push to take out a reverse mortgage. That was the crack investigators needed.

📜 What is Religious Affinity Fraud?
A scam that exploits shared religious beliefs to build trust and credibility. Bernie Madoff used golf clubs; Gallagher used church pews. Fraudsters often pose as devout community members, using scripture, prayer, and church networks to recruit victims. The Gallagher case is one of the largest recent examples in the U.S.

The Affair, the Safe, and the Coins

As the investigation deepened, authorities uncovered Gallagher’s secret office and a 2,400-pound safe — empty except for a list of gold and silver items. They also uncovered a long-running affair between Gallagher and Debra Mae Carter.

Carter had received at least $1.5 million from Gallagher, laundered through her daughter’s accounts, and spent it on rural properties. When police arrested her, she led them to a stash of gold and silver worth $300,000 — including South African Krugerrands and “President Trump coins.”

Prison Sentences and Lingering Losses

In 2020, Gallagher pleaded guilty to securities fraud and money laundering, earning 25 years and $10.3 million in restitution. In 2021, he pleaded guilty to more charges and got three life sentences. Carter was convicted in 2024 and also got life.

Gallagher tried to rationalize his crimes, claiming he was “borrowing” for good causes or investing in miracle businesses. One of them, Hover Link, supposedly went from hovercrafts to cancer cures to body armor. In reality, it was another Carter-fronted shell.

Recovery has been slow. As of early 2025, victims have gotten back only 20% of what was stolen. And new scams target them still — fake FBI agents asking for bank details.

💡 Fraud Prevention Quick Check

Verify licenses on FINRA BrokerCheck and SEC IAPD.
Be wary of any “guaranteed” returns.
Don’t ignore small inconsistencies — they often hide big lies.

Timeline: The Rise and Fall of “Doc” Gallagher

Year	Event
1941	Born in New York City.
1960s	Peace Corps service in Thailand; religious conversion.
1993	Launches Gallagher Financial Group in Texas.
1999	Reprimanded by Texas regulators for fraudulent practices.
2001–2009	Drops all active broker/advisor registrations.
2015	Allianz Life flags suspicious withdrawals; investigation begins.
2018	James & Carol Herman push for $100k withdrawal; case gains momentum.
2020	Pleads guilty; sentenced to 25 years + $10.2018 James & Carol Herman push for $100k withdrawal; case gains momentum.
2021	Pleads guilty to more charges; gets three life sentences.
2024	Debra Mae Carter convicted, sentenced to life.
2025	Victims have recovered ~20% of stolen funds.

One Last Word

The Gallagher saga proves it: trust should be earned by verification, not granted by shared faith.

🎧 Listen to the full Oh My Fraud episode for every twist and absurd detail, told with the wit only Caleb can bring.

The Legal Default Every Tax Pro Gets Backwards About Married Filing Status

Earmark Team · September 8, 2025 ·

Your tax software automatically defaults to “Married Filing Jointly” the moment you indicate a client is married. Your training taught you that joint returns almost always produce better tax outcomes. Your clients assume that filing together is not just preferred, but somehow more “correct” than filing separately.

Here’s what most practitioners miss: the legal hierarchy works in reverse of what we assume.

This insight comes from Jeremy Wells on his Tax in Action: Practical Strategies for Tax Pros podcast, where he walks through one of the most misunderstood areas in tax practice. The reality? Filing separately isn’t the alternative—it’s the legal default under the tax code. Joint filing is an election under Code Section 6013 that requires both spouses’ explicit consent. If either spouse refuses, both must file separately, period.

While tax software defaults to married filing jointly and most practitioners assume it’s always the better choice, understanding the actual legal framework changes how you approach married clients—especially when non-tax factors create situations where paying more in taxes delivers better overall financial outcomes.

Understanding the Legal Framework Behind Filing Decisions

The foundation of smart filing decisions starts with grasping what the law actually says versus what practice assumes. Code Section 6013 doesn’t make joint filing automatic. It allows couples to “jointly elect” to file together if both spouses agree.

“Filing separately is actually the default,” Wells says. ”If it weren’t for code section 6013, we would have all married couples filing separate returns.” Without this specific code section creating the joint filing option, every married person in America would file individually.

Yet tax software creates false defaults that completely reverse this legal structure. The moment you indicate a client is married, the software assumes joint filing “to the point at which we have to backtrack whenever a situation comes up that might lead us to consider filing separate returns instead.”

This backward approach means we assume joint filing is normal and treat separate filing as the exception that needs justification. But legally, it works the other way around. Joint filing is the special election that both spouses must actively choose.

Wells explains, “The joint return, although it tends to produce the better result from a tax perspective, isn’t the default.” The better tax result doesn’t automatically make it the legal starting point.

Understanding this legal framework becomes crucial in situations involving financial disagreement, pending divorce, or simple disagreement between spouses. One spouse cannot force the other into a joint return, and that protection exists precisely because the law treats separate filing as the baseline position.

This legal reality also affects how you approach client conversations. Instead of asking “Why would you want to file separately?” you might ask “Do you both want to elect joint filing?” It’s a subtle shift that acknowledges the actual legal structure while opening space for clients to express concerns they might not otherwise voice.

The Tax Code’s Systematic Push Toward Joint Returns

Understanding why the tax code penalizes separate filers reveals both the logic behind joint filing’s popularity and the threshold where those penalties become acceptable costs for better overall outcomes.

The most immediate impact comes through tax rates and brackets. “Tax rates tend to be lower on a joint return,” Wells explains. Separate return brackets are higher but also smaller, meaning “more income being taxed at lower marginal rates” on joint returns, creating “a relatively lower effective rate across the returns.” For many couples, this difference alone can mean several thousand dollars in additional taxes when filing separately.

But the real penalties come from eliminating or restricting credits and deductions. The earned income credit, American Opportunity credit, and lifetime learning credit simply disappear for separate filers. Other credits have their income limitations cut in half. For example, the child tax credit and retirement savings contributions credit phase out at income levels that are 50% of joint return thresholds.

The Roth IRA contribution restriction is perhaps the most puzzling example. “Contributions to Roth IRAs are phased out for a modified AGI of just $10,000 for separate returns,” Wells notes. “This, honestly, is one of the provisions that really just confuses me… I’m not really sure what the justification for that is.” The practical effect? Most working couples filing separately simply cannot contribute to Roth IRAs at all.

Wells points out other significant restrictions. The state and local tax (SALT) cap drops from $10,000 for joint filers to just $5,000 for separate filers, even though single filers get the full $10,000 cap. The capital loss deduction gets cut in half from $3,000 to $1,500, and the student loan interest deduction disappears entirely for separate filers.

The “itemization trap” creates another layer of complexity. If one spouse itemizes deductions, the other spouse must also itemize—they cannot claim the standard deduction. This creates challenges when his firm prepares a return for one spouse but cannot get information about the other spouse’s filing decisions. “If we just don’t know, then we go with the approach that is most advantageous to the taxpayer we’re working with. But we issue a strong caveat.”

These disadvantages create what Wells calls a “preference” toward joint filing that has become so assumed that practitioners often don’t consider separate filing until specific problems arise. Yet understanding these penalties helps identify situations where accepting them delivers superior overall results.

When Separate Filing Makes Financial Sense

The mark of sophisticated tax practice isn’t finding the lowest tax liability; it’s delivering the best overall financial outcome for clients. Sometimes that means recommending the higher-tax option.

“Our job as tax professionals is not always to prepare the simplest, most tax-efficient return possible… Sometimes, our job is to advise the taxpayer on the options and tradeoffs and help them achieve the best overall result for their personal and financial needs.”

Student loan income-based repayment plans drive most separate filing decisions in modern practice. “Nine out of ten times when we file married filing separate returns in our firm, it’s because of student loan income-based repayment plans,” Wells says. These plans calculate monthly minimums based on the borrower’s tax return income. File jointly with a high-earning spouse, and those monthly payments can become unaffordable.

The financial impact often dwarfs any tax savings from joint filing. When one spouse owes substantial student loans while the other earns significant income, filing separately might increase taxes by $2,000 but reduce annual loan payments by $6,000, creating a net benefit of $4,000 for choosing the “higher tax” option.

Wells addresses practitioner hesitation about this strategy: using filing status as a tool to achieve a financial goal is completely legitimate. It absolutely is proper tax planning, he emphasizes. There’s no ethical concern, no audit risk, no regulatory problem. It’s smart financial planning that considers the complete picture.

Financial protection scenarios create another category where separate filing is advantageous. When couples face “disagreement, mistrust, or even financial abuse,” separate filing is about financial survival and legal protection.

Both spouses on a joint return become “jointly and severally liable for the tax liability,” meaning either spouse can be held responsible for 100% of any tax debt. This remains true even after divorce. IRS collection efforts don’t respect divorce decree assignments of tax liability because the IRS was never a party to that agreement.

Treasury offset protection is another practical application. When one spouse defaults on student loans, the federal government can garnish the entire joint refund to pay that debt. “Filing separately could protect that spouse’s refund… Getting some of that refund with a separate return could be a better result than having the entire refund garnished by the student loan lender,” Wells explains.

Separate filing may also unlock better results for AGI-limited deductions. The 7.5% AGI threshold for medical expenses is much more achievable when calculated against one spouse’s lower individual income rather than the couple’s combined AGI. Wells notes this same principle applies to casualty losses at 10% of AGI.

“Tax filing status is never a reflection of the couple’s marriage or relationship,” Wells explains, countering clients’ concerns that separate filing might signal relationship problems. “There’s nothing wrong about filing separate returns. Nobody looks at separate returns and thinks that’s an indication of something wrong with your marriage.”

Professional Implementation and Practice Management

The realities of implementing separate filing strategies reveal professional challenges beyond tax calculations. Wells shares insights from his firm’s experience that help practitioners navigate these complex decisions effectively.

One fundamental challenge involves timing and irrevocability. Wells explains the common saying, “A couple can make up, but they can’t break up.” Once you file jointly and pass the filing deadline, you generally cannot switch to separate returns. However, the reverse is possible. Separate filers can amend to joint returns within the statute of limitations.

There are limited exceptions to this rule. Couples can file a superseding return before the unextended due date to switch from joint to separate. They can also amend joint returns to separate if the marriage gets annulled, if one spouse can prove the joint return was signed under duress, or if both taxpayers didn’t properly sign the joint return. However, these exceptions require a substantial legal burden of proof.

Technology can streamline the analysis process, as professional tax software includes joint versus separate worksheets. These comparison tools show four columns: the joint return result, each spouse individually as if filing separately, and the combined result of two separate returns. “Usually it’s not an insignificant amount of money. A lot of times we see several thousand dollars” in savings from joint filing, Wells notes.

Wells uses these worksheets for quality control. “That comparison can actually help work through whether or not we’ve made an error.” For example, if all wages show under one spouse and none under the other, it might indicate misallocated W-2s that could incorrectly trigger Social Security overpayment calculations.

Wells describes a specific error his firm caught this way. “I have mislabeled those W-2s and that’s triggered a calculation of that excess Social Security tax paid.” Since Social Security overpayment calculations work on an individual basis, not a joint return basis, misallocating W-2s between spouses can create incorrect refund calculations that later generate IRS notices.

Conflict of interest considerations are crucial when working with couples contemplating separation or divorce. “Working with a married couple that is on the rocks might cause a conflict of interest, especially if the firm started working with one spouse before the couple got married,” Wells explains. Some firms require written waivers, while others simply refuse to work with both spouses during contentious situations.

Different firms handle separate filing preparation differently. Wells notes that some treat separate returns as completely independent engagements with separate fees for each spouse. Others charge for three returns when preparing both joint and separate scenarios. The key is establishing clear policies before these situations arise.

Transforming Client Relationships Through Strategic Tax Planning

The separate filing decision is sophisticated tax practice at its best, where technical knowledge meets strategic thinking to deliver advice that considers clients’ complete financial circumstances rather than just tax calculations.

Wells’ approach demonstrates how understanding these concepts transforms client relationships. Instead of simply optimizing tax calculations, you help clients navigate complex financial decisions that affect their long-term financial health. You become the advisor who understands that sometimes paying more in taxes is the smartest financial move.

Client education is crucial for successful implementation. Wells often encounters clients who resist separate filing because they believe it signals relationship problems or creates complications. Having clear, confident responses to these concerns, backed by a solid understanding of the legal framework, positions you as the expert who can cut through confusion.

“Our job as tax professionals is not always to prepare the simplest, most tax efficient return possible,” Wells says. “Sometimes, our job is to advise the taxpayer on the options and tradeoffs and help them achieve the best overall result for their personal and financial needs.”

This philosophy requires moving beyond traditional tax optimization to consider complete financial circumstances. When you can save a client thousands in student loan payments by recommending separate filing (even while paying extra taxes), you’ve delivered genuine strategic value that differentiates sophisticated tax professionals from basic return preparers.

The separate filing decision crystallizes everything that makes tax planning both challenging and valuable: technical complexity, client relationship management, strategic thinking, and the wisdom to optimize for outcomes rather than just tax calculations. It’s where true tax professionals prove their worth by delivering advice that transforms clients’ financial lives.

Ready to master these strategic filing decisions that could save your clients thousands while protecting them from significant financial risks? Listen to Jeremy Wells walk through the complete framework for navigating married filing status elections, including real-world examples and technical details that will change how you approach these decisions.

From Guilt to Grace: How Setting Boundaries Actually Improves Client Service

Earmark Team · September 5, 2025 ·

You decide to sleep in for once, rolling over in bed to ignore the world and give yourself a much-needed break. Then your phone buzzes with an email notification that makes your blood boil instantly: a one-star Google review from a client who’s furious that you won’t drop everything to take his phone calls.

This exact scenario happened to Nayo Carter-Gray, an Enrolled Agent (EA) who runs her own accounting firm, just a couple of weeks before she joined Nancy McClelland and Questian Telka for a live episode of She Counts recorded at the Scaling New Heights conference. The client in question was part of a client list acquisition, bypassed Carter-Gray’s communication policies from Day One, and demanded immediate callbacks despite her firm’s clear appointment-only structure.

Here’s the kicker: After Carter-Gray crafted a nearly 5,000-word response (thankfully never sent), the client discovered the real problem was a tech issue on his end that had been blocking emails for a week. “He took his review down because he discovered the thing that he was upset about was not even our fault. It was his,” Carter-Gray explains.

The client took down his nasty review, but the damage to the relationship was done. More importantly, Carter-Gray realized this was a blessing in disguise, a clear sign this client wasn’t a good fit for her practice.

This story perfectly captures the tension that accounting professionals face every day: the clash between setting professional boundaries and managing client expectations in a culture that demands instant gratification. During their conversation about boundaries, McClelland, Telka, and Carter-Gray tackled one of the most challenging aspects of running a sustainable practice: protecting your time and energy without sacrificing service quality or damaging client relationships.

Professional boundaries aren’t about saying ‘no’ to clients; they’re about saying ‘yes’ to better service.

From Barriers to Bridges: Reframing the Boundary Mindset

Transforming boundary-setting from a guilt-inducing struggle into a service enhancement tool starts with a simple reframe. As Carter-Gray puts it, “Boundaries aren’t barriers, but bridges to better client relationships.”

This philosophy runs counter to everything most accounting professionals have been conditioned to believe. We’ve been taught good service means being available whenever clients need us; saying ‘no’ makes us difficult; and professional success requires wearing every hat in our practice. But Carter-Gray’s experience tells a different story.

When she initially set up her firm, she was doing exactly what most of us do: trying to handle everything herself. “I was doing all the things, trying to set the appointments, trying to have all the client calls,” she recalls. “I realized I was spending so much time on things clients can do themselves, like schedule an appointment.”

The breakthrough came when she asked why clients had to talk to her to schedule a call with her. “When I call the doctor’s office, the doctor isn’t the one on the phone scheduling a call. It’s usually the front desk admin or a nurse practitioner or somebody lower on the rung,” she explains.

This realization led to restructuring how her firm operates. She implemented scheduling links, started using an answering service, and created clear communication protocols that actually freed her up to focus on the work that truly requires her expertise.

“When I’m talking to you, I wanna just be able to talk to you and not have any distraction,” Carter-Gray explains. This captures the essence of the boundary-as-bridge concept. By protecting her time and attention through clear systems, she creates space to be fully present with clients when they do connect. The boundaries enhance the service rather than diminishing it.

Building Systems That Support Your Boundaries

The magic of effective boundary-setting isn’t the boundaries themselves, but the systems that make those boundaries feel natural and professional rather than defensive or apologetic. Carter-Gray’s approach demonstrates how multiple touchpoints and clear processes can eliminate the need to justify your professional structure.

“I try to do a really good job of explaining it the first time,” Carter-Gray explains, outlining her multi-layered client education process. “In our potential client call, I’ll walk you through the process. It’s at the bottom of our follow-up email, and we reiterate it in our welcome guide.”

This welcome guide serves as a proactive boundary-setting tool. Rather than waiting for conflicts to arise and then having to explain policies defensively, the guide educates clients before issues develop. “It is in the engagement letter as well,” Carter-Gray adds, acknowledging that “people don’t read,” which is why repetition across multiple formats is essential.

Her automation strategies go beyond simple scheduling tools. “You fill out the potential client form. I get an email that tells me all about you, and then we accept it or decline it based on your responses,” she explains. Once accepted, automated emails go out immediately to capitalize on the client’s momentum while setting clear expectations about what comes next.

One practical example of systematic boundary-setting is her approach to business hours. “We’re virtual. That doesn’t mean we’re 24/7. We have business hours. We work Monday through Friday, 10:00 AM to 6:00 PM Eastern Standard Time,” she states firmly. But she goes a step further, scheduling emails to send during business hours even when she writes them on weekends.

“I stopped sending emails on weekends because sending an email on a Saturday at seven gives the impression that you’re working,” she explains. “So even though I might be working on Saturday, I schedule the email for Monday morning at 10:00 AM Eastern (or 10:05, so it won’t feel like I’ve scheduled the email).”

Her team structure reinforces these boundaries through shared systems rather than individual heroics. “We use a shared email inbox,” she explains, “so every meeting, every email is seen by the entire team that’s responsible. At any given point, if one of us is out, somebody else can jump in.”

This prevents the single-person bottleneck that destroys boundaries when clients believe only one person can help them.

Perhaps most importantly, Carter-Gray aligns her systems with her personal energy patterns. “Sales calls are on Monday because I am pumped up for the week,” she shares, demonstrating how boundaries can actually optimize performance when they’re designed around how you naturally work best.

Here’s her professional out-of-office template:

“Dear Client, from [start date] to [end date], I’ll be taking some much-needed time off. For urgent matters, please contact [colleagues]. I value our partnership and assure you that all tasks will be handled with the same dedication and efficiency.”

No lengthy explanations. No apologies. Just clear, professional communication about availability.

Overcoming Guilt and the People-Pleasing Trap

The most sophisticated boundary systems in the world will crumble without addressing the psychological patterns that make saying “no” feel impossible in the first place. For many accounting professionals, the real battle is with the internal voice that whispers… we’re being difficult, selfish, or unprofessional when we protect our time and energy.

“If you feel guilty about all of the things, then you will never feel good about all of the things,” Carter-Gray points out. This guilt cycle creates a destructive pattern where professionals overcommit to avoid disappointing others, then build resentment toward the very clients they’re trying to serve.

“Sometimes you have to take your guilt and say, ‘Why am I feeling guilty about this? Is it because I’m not able to do this? Or is it because I don’t want to do this?’” Carter-Gray challenges. “When you realize it’s something you don’t want to do, the answer’s no.”

The power of “no is a complete sentence” prevents the resentment that destroys service quality. “I don’t wanna resent you, I wanna be able to enjoy whatever relationship that we have,” Carter-Gray explains. “Every time I see you, I don’t wanna be like, oh, let me avoid this girl.”

The oxygen mask principle flight attendants teach is a perfect parallel for professional service: “You gotta take care of your mask first before you help others,” Carter-Gray reminds us. This isn’t selfishness; it’s sustainability.

Even the language patterns that reinforce guilt need conscious attention. Telka recognizes herself as an over-apologizer, a common pattern among women in professional settings. Carter-Gray offers a simple but powerful reframe: “Instead of being sorry for something, thank the other person for their patience. So instead of, ‘oh, I’m sorry I’m late,’ say ‘thank you for your patience. You waited for me.’ Really I should be saying… let’s honor, let’s celebrate that.”

The deeper principle at work here challenges the entire culture of instant availability that pervades professional services. “Don’t apologize for taking personal time. We are humans. We are not robots. We are not made to work 24/7,” Carter-Gray states firmly. “If you worked for someone else and your hours were nine to five and they asked you to come in at seven, you would be pissed. So you work for yourself, but you don’t set up these same rules for yourself?”

Carter-Gray’s favorite saying captures this mindset: “Not your monkey, not your circus.” In other words, you don’t have to jump into every chaotic situation just because you have the skills to help.

Small Steps to Start Today

For conflict-averse accounting professionals who want to start practicing boundary setting, Carter-Gray suggests beginning with low-stakes changes:

Email auto-responders. “You can set your emails now to have a responder that says ‘Thank you so much for your email. We will get back to you within 48 business hours.’ It takes a little pressure off of you to respond immediately.”
Virtual assistants or chatbots. These can help take over some of the communication functionality that currently pulls you away from client work.
Clear communication about availability. Be proactive about telling clients when you’ll be unavailable, giving them time to prepare mentally.
Provide alternatives. When you can’t help directly, offer other solutions. As McClelland points out, this might mean saying, “I’m not available to help with that. However, I have an amazing team that I’ve invested a lot of my time and energy into training. And they will take really great care of you.”

The key is being proactive rather than reactive.

Your Path to Sustainable Service Excellence

Professional boundaries aren’t about becoming the difficult accountant who never helps anyone; they’re about becoming the professional who helps the right clients exceptionally well. The most sustainable practitioners don’t say “yes” to everything. They create frameworks that protect their ability to serve authentically.

This approach offers a roadmap for any accounting professional ready to move beyond the exhausting cycle of over-commitment and resentment and gives them permission to prioritize sustainability without guilt.

Take the first step by choosing one small boundary to implement this week. Maybe it’s an email auto-responder that sets response time expectations. Perhaps it’s scheduling your weekend emails to send during business hours. Or it could be as simple as switching your language from “I’m sorry I’m late” to “Thank you for your patience.”

Listen to the full episode of the The Counts podcast featuring Nayo Carter–Gray for more advice on setting boundaries to become sustainable, focused, and authentically present.

You can follow Nayo Carter-Gray on social media @NayoCarterGray and learn more about her work at upcoming conferences, including Bridging the Gap, NAEA’s Tax Summit, and Intuit Connect. She also serves on the board of the Accounting Cornerstone Foundation, which provides scholarships for first-time conference attendees in the accounting profession.

Why S Corporation Elections Backfire More Often Than You Think

Earmark Team · September 5, 2025 ·

Early in his accounting career, Jeremy Wells, EA, CPA, landed what seemed like the perfect client: a newly independent contractor drowning in tax debt to both the IRS and his state agency. Within just a couple of years, Wells helped transform this financial disaster into a success story. Through strategic S corporation planning, proper bookkeeping, and careful tax planning, his client went from owing thousands to receiving small but satisfying annual refunds.

The S corporation election was absolutely the right move. But Wells emphasizes that this was the right client at the right time, with the right circumstances.

In a recent episode of Tax in Action, “S-Corporation Reality Check,” Wells examines the oversimplified advice flooding social media feeds and startup marketing campaigns. While countless online voices promise S corporation elections deliver automatic self-employment tax savings for any successful self-employed person, Wells sees this advice creating expensive problems for businesses that never should have made the election in the first place.

“There’s a cottage industry developing around this concept,” Wells explains. We’re in a perfect storm where remote work and the gig economy have created lots of successful self-employed people who need tax help, but there’s a shortage of qualified advisors who can provide proper guidance.

The reality is, while this cottage industry promises easy self-employment tax savings, the one-size-fits-all approach ignores critical deal-breakers that can transform a supposed tax benefit into a costly mistake.

Balance Sheet Red Flags That Kill S Elections

The cottage industry’s relentless focus on self-employment tax savings completely sidesteps fundamental balance sheet realities that can make S elections counterproductive or even trigger unexpected taxable events.

The most dangerous misconception involves debt basis. Unlike partnerships, where partners receive basis credit for their share of entity debt, S corporation shareholders get no such benefit unless they personally loan money to the corporation.

“I can go get a loan and intend to use the funds in my S corporation, but if I personally guarantee that debt, that is not me generating debt basis,” Wells explains. “I am not loaning money to my corporation.”

This distinction catches many business owners—and their advisors—completely off guard. The COVID-era Economic Injury Disaster Loans are a perfect example of this misunderstanding. Thousands of sole proprietorships took personally-guaranteed SBA loans and later elected S corporation status, only to discover that their EIDL debt provided zero debt basis benefit. When these businesses generated losses, shareholders couldn’t deduct them against other income because they lacked sufficient basis.

But there’s another trap buried in the S election process itself. When an LLC elects S corporation status, the tax code requires a two-step transaction that most people don’t understand. First, the LLC becomes an association taxed as a C corporation, then immediately elects S status. During that first step, a Section 351 exchange occurs where the entity’s assets and liabilities transfer to the new corporation in exchange for stock.

Here’s where it gets dangerous: if the business has liabilities exceeding assets—not uncommon for debt-heavy service businesses with minimal fixed assets—this exchange creates taxable gain. “We might be inadvertently generating a taxable event for that owner or those partners when they make that selection,” Wells warns.

The equity structure challenges run even deeper. S corporations demand a single class of stock, pro-rata allocations of everything, and pro-rata distributions with no exceptions. “All items of income, loss, deduction, gain and credits must be allocated to the shareholders pro rata based on their percentages of ownership in the corporation stock, and there are no exceptions to that,” Wells notes.

This inflexibility is particularly problematic for businesses planning future acquisitions. Many small businesses today are built with acquisition in mind—not just Silicon Valley startups, but local businesses designed to be attractive to buyers within three to ten years. S corporations complicate these plans because many acquisition entities aren’t qualified S corporation shareholders. Non-US entities, partnerships, and C corporations can’t own S corporation stock, forcing expensive workarounds.

This is why Wells always asks clients about their long-term goals: “We always have to plan with the end in mind, especially when it comes to equity.”

Operating Agreements: The Hidden S Election Killers

The S corporation promotion industry systematically ignores a fundamental reality: most operating agreements are legal landmines for S elections. Wells’ firm learned this lesson the hard way, which is why they now require operating agreements from all multi-member LLC clients before making any S election recommendations.

“We read through it and try to pick out these terms and concepts and potential red flags,” Wells explains. What they consistently find are documents written exclusively for partnership taxation under Subchapter K—documents that can directly contradict the rigid requirements of Subchapter S.

The most dangerous provisions involve substantial economic effect requirements under Section 704(b). Partnership operating agreements routinely include liquidation provisions requiring distributions based on positive capital accounts. This creates non-pro-rata distribution requirements that are perfectly normal for partnerships but absolutely prohibited for S corporations.

Wells has encountered operating agreements that explicitly prohibit S elections, containing language like “this LLC will always be a partnership for tax purposes” or “the business cannot do any sort of corporate election.” Even more commonly, he’s seen agreements with waterfall distribution clauses that prioritize some members over others—a structure that violates S corporation pro-rata distribution requirements and can trigger inadvertent election termination.

Perhaps most problematic, Wells notes: “I have never seen an operating agreement in an original draft that listed out what happens if an S election takes place.” Most templates simply don’t consider the possibility, leaving businesses with agreements that actively work against their tax election goals.

Even operating agreements that appear silent on these issues often default to state partnership laws that can require non-pro-rata distributions. “If we have an operating agreement that doesn’t really cover these topics, that’s when state law intervenes,” Wells explains.

The solution requires proactive legal work that the quick-and-easy S corporation services don’t provide. Businesses need either revised operating agreements that explicitly allow for S elections or entirely new agreements written with tax flexibility in mind. This legal work might cost a few thousand dollars upfront, but it’s far cheaper than dealing with an inadvertent election termination that requires a private letter ruling or Tax Court intervention.

The Math Doesn’t Add Up: Hidden Costs and Incomplete Calculations

The S corporation promotion machine focuses entirely on self-employment tax savings while conveniently ignoring every other aspect of a client’s tax situation. This creates problems where businesses make expensive elections based on wildly inaccurate financial projections.

The most glaring flaw involves reasonable compensation requirements. “A lot of the estimates of tax savings with an S election just estimate reasonable compensation way too low,” Wells observes. “Those tax savings are not the result of the S election. Those tax savings are unreasonably low salaries being paid through those S corporations.”

It’s a mathematical sleight of hand. Of course, any advisor can eliminate 100% of self-employment tax by simply not running payroll to active S corporation shareholders. But this isn’t tax planning; it’s setting clients up for IRS problems down the road.

The Section 199A qualified business income deduction creates another calculation error that the cottage industry ignores. Higher reasonable compensation reduces the pass-through income that forms the basis for this valuable 20% deduction. As Wells explains: “We save a little bit of self-employment tax at the expense of a pretty significant deduction for a lot of small business owners.”

For many successful small business owners, losing substantial QBI deductions easily outweighs any self-employment tax savings from an S election.

State and local taxes deliver the knockout punch to many S election projections. Tennessee imposes a 6.5% tax on S corporations. New York City hits S corporations with an 8.85% rate. California charges the greater of $800 or 1.5% of net income. As Wells puts it, “Those taxes can wipe out any projected tax savings from an S election.”

A business owner in Tennessee could save $3,000 in federal self-employment tax only to pay $5,000 in additional state tax. The cottage industry’s federal-only analysis turns a supposed tax benefit into a $2,000 annual penalty.

The complications extend to asset transactions. S corporations create taxable gain when distributing appreciated property to shareholders, which is a problem that partnerships avoid. For businesses holding real estate or other appreciating assets, this difference can cost tens of thousands in unexpected taxes. That’s why Wells generally recommends not holding real estate in an S corporation.

Similarly, S corporations lose access to Section 754 elections that allow partnerships to step up the inside basis of assets when ownership changes. This valuable planning tool helps partnerships minimize taxes when partners sell their interests or inherit them. S corporations simply don’t have this option.

The Professional Alternative to Checkbox Solutions

The problems with S corporation election advice reveal a broader issue: complex tax decisions are being oversimplified into marketing soundbites. While the cottage industry profits from reducing professional judgment to self-employment tax calculators, tax professionals face a choice between participating in this race to the bottom or demonstrating why expertise matters.

“We need to seriously look at what that entity election will mean for the business today, in the future, and for the shareholders or partners themselves,” Wells says. This level of analysis requires understanding balance sheet implications, legal document conflicts, comprehensive tax calculations, and long-term business planning—expertise that can’t be packaged into a simple online service.

When clients arrive demanding an S election because “everyone online says it saves taxes,” the professional response isn’t to immediately comply or dismiss the idea. Instead, walk them through the complete analysis: balance sheet structure, operating agreement provisions, reasonable compensation realities, QBI impacts, state tax consequences, and future business goals.

This educational approach protects clients from expensive mistakes while positioning you as genuinely knowledgeable rather than just another order-taker. It creates long-term relationships built on trust and demonstrated expertise.

While the cottage industry promises simplicity, its oversimplified approach consistently creates far more complexity down the road. Inadvertent election terminations, operating agreement conflicts, unexpected state taxes, and acquisition complications all require costly professional intervention to resolve.

For tax professionals willing to master this complexity, the S corporation election presents both a professional responsibility and a market opportunity. Clients need advisors who can navigate the factors that determine whether an S election truly benefits their specific situation.

Good tax advice requires understanding the complete client situation, not just plugging numbers into a self-employment tax calculator.

To hear Wells’ complete analysis and learn how to position yourself as the thoughtful alternative to the S corporation promotion industry, listen to the full Tax in Action podcast episode where he details the specific questions to ask and analyses to perform that separate professional advice from marketing-driven recommendations.

QuickBooks Online’s Latest AI Update Could Save You Hours of Detective Work

Earmark Team · September 1, 2025 ·

Picture this: You’re reviewing a client’s profit and loss statement when travel expenses catch your eye. They’ve jumped 624% from last month. Is this legitimate business growth, a categorization error, or duplicate entries? Traditionally, this would mean hours of detective work, drilling into transaction details and cross-referencing receipts.

But what if an AI agent had already investigated this anomaly, traced it back to two identical $10,834 hotel charges, and presented you with a detailed report, complete with visual charts and actionable recommendations?

This feature is rolling out to QuickBooks Online users this summer.

In this episode of The Unofficial QuickBooks Accountants Podcast, Jim Dzundza, Staff Product Manager for the QuickBooks Accounting Automation team, explains how AI-powered error detection agents are transforming accounting workflows. But this isn’t about robots replacing bookkeepers. It’s about intelligent collaboration where AI handles time-consuming pattern recognition while accountants focus on analysis and client relationships.

From Program Manager to Product Developer

Dzundza’s journey at Intuit offers unique insight into how accountant feedback shapes product development. He started on the business development team working on desktop product partnerships, then moved to manage the ProAdvisor program for several years.

“Accountants have had a special spot in my heart,” Dzundza explains. “They are the key to us developing amazing products and amazing functionality.” His transition from the front-facing ProAdvisor program to backend product development wasn’t accidental; it was driven by impact.

“I felt like I could make a bigger impact by bringing this accountant perspective and finding a team within Intuit that really thinks about how accountants use and love the product,” he says. “And then focusing on where a lot of the pain is, to be honest. How can we help accountants reduce the pain of the work that they have to do?”

This accountant-first approach shows in every feature Dzundza shared on the podcast.

The AI Agent Revolution Begins

QuickBooks Online’s new platform introduces six specialized AI agents, each designed for specific accounting functions. The accounting, payments, and finance agents are currently available. Project management is in beta, while payroll and customer agents are coming soon.

The rollout timeline is aggressive but manageable. All new files created now automatically use the new platform. Starting in July, existing users can opt into the new experience. By September, everyone will see it, with the ability to opt out until the transition becomes mandatory at the end of September.

“We are daily reviewing feedback that is streaming in around all of the new UI, the new agents, everything coming out,” Dzundza emphasizes. “We’re implementing fixes and changes based on user feedback.”

This feedback period allows accountants to shape these tools rather than simply accepting what’s provided.

Eliminating Data Entry Frustrations

The accounting agent tackles three major workflow areas: getting transactions into the books, categorizing them, and reconciling accounts. Each advancement addresses real pain points accountants face daily.

PDF Statement Upload

For years, working with small banks meant manually keying transactions or using third-party tools like MoneyThumb. The new PDF statement upload feature completely changes this.

“You have the PDF and you go in to add that statement or upload those transactions in the same way you would upload a CSV today,” Dzundza explains. “And now you’re able to upload a PDF.” The AI extracts transactions directly from bank statement PDFs, eliminating the need for external conversion tools.

Enhanced Collaboration

Perhaps more revolutionary is the new collaboration feature available on Essentials and above. When you encounter a transaction needing clarification, you can ask questions directly within the bank feed and send clients a magic link via email or text.

“They can go on their phone and answer the question,” Dzundza notes. “They can answer it from wherever without having to log into QuickBooks.” Once clients respond, the AI automatically updates its categorization recommendations based on that context, creating a feedback loop that improves accuracy for future similar transactions.

This addresses a major frustration: forcing business owners to log into QuickBooks just to answer simple questions about transactions. It also gives accountants control over their books while still gathering necessary context.

Reconciliation Gets Smarter

The reconciliation process receives similar AI enhancements, with tools launching in mid-July. Like bank feeds, reconciliation now supports PDF extraction with a crucial enhancement: when the AI can’t extract everything accurately, it flags questionable areas for human review.

“Our goal for this one is 100% accuracy,” Dzundza explains. This hybrid approach, combining AI speed with human verification, ensures accuracy while eliminating manual data entry.

The new reconciliation interface organizes information into logical sections: cleared transactions that matched one-to-one, flagged one-to-many matches requiring review, and AI recommendations for transactions that should potentially be excluded or unposted.

This addresses common reconciliation headaches like duplicate detection. As Dzundza discussed with host Alicia Katz Pollock, it’s easy to upload a receipt and then also accept the same transaction from the bank feed without noticing the duplication. The AI now surfaces these duplicates automatically, eliminating manual scanning for errors.

The Anomaly Detection Game-Changer

The most sophisticated feature is the accounting agent’s anomaly detection, which transforms financial statement review from manual line-by-line scanning to intelligent pattern analysis.

How It Works

The system analyzes 13 months of historical data, comparing the most recent complete month against established patterns to identify accounts that deviate significantly from normal behavior. But it’s smarter than simple variance detection. It considers each account’s historical volatility. Accounts with consistent monthly variation won’t trigger alerts for normal fluctuations, while stable accounts get flagged for even modest deviations.

“It looks over the past 13 months, and then it looks at the most recent complete month,” Dzundza explains. “And it will tell you if this month’s total seems off on either the balance sheet or P&L.”

Professional-Quality Investigation

When the system detects anomalies, the AI conducts detailed investigations using what Dzundza describes as “customized prompts we designed in partnership with accountants.” These prompts guide the AI to analyze transaction patterns, identify common characteristics, and surface potential root causes.

Travel expenses are a perfect example of this capability. When the AI flagged a 624% increase in travel expenses, it didn’t just note the variance; it traced the increase to two identical $10,834 hotel charges from the same vendor, immediately raising the question of whether these were duplicates or legitimate separate transactions.

Seamless Integration

The feature integrates directly into standard financial statements through subtle blue sparkles next to affected line items. Clicking a sparkle opens a detailed analysis directly in context, allowing investigation without leaving the familiar report format. The sparkles don’t print when you export reports, maintaining clean client deliverables while providing powerful review capabilities.

Actionable Reporting

The AI generates professional-quality PDF reports that serve as both investigation summaries and work papers. These reports include visual charts showing the anomaly, detailed root cause analysis, supporting data points with reference numbers for easy transaction lookup, and comprehensive narrative explanations of findings.

As Katz Pollock notes, “this is something I would be very happy to just send to my client.”

The Partnership Model That Works

These AI updates aren’t about replacing accountants, but about elevating their work.

“It’s not about replacing jobs or anything like that,” Dzundza emphasizes. “It’s really focused on creating tools that make people more efficient in getting their work done.”

As Katz Pollock summarizes, “this is in no way taking your job. All this is doing is calling your attention to things that it’s noticed in a way that you would not have access to just by looking.” The technology provides pattern recognition and initial investigation, but professional judgment about significance, cause, and appropriate action remains firmly in human hands.

Your Voice in the Development Process

Dzundza stresses that development teams are reviewing user feedback daily and implementing changes based on that input.

This gives accounting professionals a unique opportunity to actively shape these tools. The key is providing constructive, actionable feedback with specific details rather than general complaints.

The Future of Accounting Practice

Technical proficiency with AI tools is becoming as important as traditional accounting skills. Accountants who embrace this partnership will find themselves elevated from data processors to strategic advisors, spending less time hunting for errors and more time interpreting their significance for clients.

The collaboration model redefines what it means to be an accounting professional in an AI-enhanced world. The accountants who thrive will be those who view AI as a powerful research assistant rather than a threat, focusing their expertise on the strategic analysis and client relationships that technology cannot replace.

As these AI agents roll out over the coming months, you have the opportunity to be part of shaping the future of accounting practice. Listen to the full episode to hear Dzundza’s complete demonstration of these features, understand the implementation timeline, and learn how to provide constructive feedback that will help refine these tools for maximum benefit to accounting professionals.

The future of accounting is being written now. Make sure your voice is part of that conversation.

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!