Podcasts

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

Earmark Team · January 28, 2026 ·

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

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

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

When Your Business Becomes the IRS’s Target

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

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

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

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

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

Who’s at Risk (And Who’s Not)

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

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

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

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

Susan Crile’s David vs. Goliath Battle

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

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

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

The Nine Factors That Saved Her Business

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

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

1. The manner in which she carried on the activity

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

2. Her expertise and that of her advisors

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

3. Time and effort expended

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

4. Expectation that assets may appreciate

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

5. Success in other activities

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

6. History of income or losses

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

7. Amount of occasional profits

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

8. Financial status

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

9. Elements of personal pleasure

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

The Verdict That Protected Creative Professionals

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

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

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

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

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

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

Practical Lessons for Tax Professionals

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

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

The Human Side of Tax Law

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

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

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

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

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

Earmark Team · January 28, 2026 ·

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

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

A Healthcare Empire Built on Shaky Financial Foundations

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

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

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

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

When Manual Processes Strangle Growth

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

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

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

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

The Complexity of Healthcare Finance

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

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

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

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

A Rapid Transformation

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

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

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

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

Life-Changing Automation

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

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

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

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

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

Building an Integrated Tech Stack

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

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

The Real Cost of Standing Still

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

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

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

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

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

Lessons for Healthcare Finance Leaders

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

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

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

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

Planning a Firm Retreat That Keeps Your Team Aligned All Year

Earmark Team · January 28, 2026 ·

Team retreats can easily become forgettable obligations. People spend a few hours in a conference room, have some general discussion about “next year,” and everyone returns to their desks unchanged. But Marcus and Rachel Dillon have spent nearly a decade figuring out how to make their twice-yearly retreats count for something more.

In this episode of Who’s Really the Boss?, recorded just after a successful year-end team retreat, the Dillons share exactly how they plan and execute gatherings that keep their remote team aligned all year long. This retreat was particularly significant, as it was the first time their entire team came together after two acquisitions that grew their firm from $3 million to $6.5 million in revenue.

Starting with Leadership Alignment

The work that made this retreat effective started in late September. Their leadership team, including Marcus, Rachel, Director of Operations Amy McCarthy, and Director of Accounting and Advisory Lezlie Reeves, met in Saint Louis, Missouri.

They were already there for a meet-and-greet related to their recent acquisition, so they carved out a full day specifically for 2026 planning. The change of location helped them focus beyond daily operations.

“We were out of our normal element, which was great because it changed the pace and place and allowed us to focus better,” Marcus explains.

The team uses a framework originally developed by C12, an organization of Christian business owners, which they’ve adapted for their accounting firm. The framework breaks planning into five key areas:

Revenue Generation. Setting targets and monitoring progress, with flexibility to adjust client onboarding based on team capacity
Operations Management. The steady force that keeps the firm grounded when new opportunities arise
Organizational Development. Team structure, hiring, roles, and succession planning three to five years out
Financial Management. KPIs and reporting—the self-accountability accountants sometimes neglect for their own firms
Ministry. How the firm gives back and serves as good stewards

What emerges is a one-page document with a matrix showing each goal area, the strategic objective, success metrics, who’s responsible (including first and second chair assignments), and deadlines.

“If there’s no timeline, you just keep kicking the can down the road,” Marcus notes. “And those goals never get touched again.”

The leadership conversations extend beyond immediate goals. They discuss where each person sees themselves in three to five years, and what they want to see happen. These discussions require openness from everyone involved.

“As a leader, you have to be prepared for whatever your fellow leaders’ answers may be,” Marcus says. “You have to be open to hearing that.”

Finding the Right Time

The Dillons learned through trial and error that when you hold a retreat matters as much as what you cover. Their timing has evolved over the years.

Initially, they held retreats in January, capturing the new year, fresh goals energy. But that created immediate conflicts. “Taking a day and a half or two days right when you come back from the holidays is tough,” Rachel explains, especially with year-end financials due by the 15th and 1099 work piling up.

They tried pushing it to after January 20th, but that still felt rushed with the January 31st deadline approaching. Moving it any later meant they were already more than a month into the year before rolling out goals.

Their current approach places the retreat in mid-November, the week before Thanksgiving. This timing works because teams have just finished the November 15th deadline for month-end financials. Leadership has ten and a half months of data to review, enough to project year-end performance and celebrate achievements without waiting for perfect December numbers.

“If people are busy and have deadlines and clients waiting and asking for things, they cannot be fully focused and engaged in the retreat,” Rachel emphasizes.

For a remote firm where more than half the team flies in, the schedule runs Sunday arrival, full day Monday, half day Tuesday, with people heading home Tuesday afternoon. This prevents taking up too much of people’s weekend and avoids the stress of same-day travel.

The Logistics That Matter

Every detail either helps team members focus or creates distraction. The Dillons have learned which investments pay off.

They provide hotel rooms for everyone who needs one, including local team members. “Some people took us up on that because they didn’t want to wake up super early, commute, and get ready. That’s just not their normal routine,” Marcus explains.

Food is available throughout both days. Hotel catering costs more than bringing things in, but it simplifies coordination dramatically. The team eats lunch off-site both days, providing mental breaks from the meeting room.

When everyone’s together, they maximize the opportunity. A photographer comes in for professional headshots, and team members cycle through during sessions without disrupting the flow. Only Monday requires professional dress; Tuesday is comfortable.

The Monday evening Christmas party happens at a nearby Brazilian steakhouse, with spouses invited. But first, the team went to Great Big Game Show, a venue where groups compete in TV-style game show formats.

“It was less than $40 per person. It was an hour and a half event,” Rachel notes. “So it was fairly cost effective but very memorable for the team.”

“It doesn’t have to be expensive to be memorable,” Marcus says.

Building Trust Through Transparency

What happens in the room determines whether the retreat creates lasting change or fades by the following week. The Dillons’ approach centers on transparency about the firm’s actual performance.

They share real revenue data, including year-to-date numbers, projections, where the firm stands against goals. Many firm owners hesitate at this level of openness, but the Dillons have only seen positive results.

“There has never been an instance where someone has come to us and said that we are unfair based on a revenue number,” Rachel says. “The only things that have come from us sharing more has been positive response and feedback.”

This transparency extends to the firm’s direction. In 2021, during their pivot to remote work, they created “Future Direction” statements, which are clear commitments:

Monitor, monetize, or refer annual tax clients outside core services
Operate within a fully connected tech stack
Share industry best practices with peers
Be the model firm in small business accounting
Attract highly qualified, highly motivated team members
Implement travel retreats
Create initiatives to give back locally and abroad

Four years later, they still reference these statements at every retreat. “We can go through and put a check mark next to every single one and point back directly to exactly how we achieved those things,” Rachel explains.

The continuity matters when firms undergo major changes. “When they look back at this, they see it’s not any different than what we said we were going to do,” she notes. “Maybe how we get there or what we use to do it changes, but the overall direction definitely aligns.”

Celebrating Before Charging Forward

The Dillons organize both achievements and initiatives into four categories: Growth (clients and team), Process (procedures and technology), Team Development, and Collective by DBA (their peer network offering). This structure ensures nothing gets forgotten between retreats.

For 2025, there was plenty to celebrate:

Securing 12 out of 15 targeted new organic clients
Two successful firm acquisitions
Multiple director-level additions including Operations, Accounting and Advisory, Technology, and Tax and Financial Planning
Implementing of Double for improved client reporting
Launching monthly role-specific training programs
Growing the team from 15 to 25 people

“I don’t do a great job of stopping to celebrate,” Marcus admits. “So I made sure that it was built in.”

Each year gets a theme. For 2025, it was “Growth, not comfort.” For 2026, they’ve chosen “Lead change, create impact,” reflecting their shift from a growth phase to refinement as they integrate everything they built.

The firm also shares specific quarterly goals and hiring plans. “When we started opening up more transparently with the financials and the overall plan of the business, we could actually invite people who are smarter and better than us in given areas,” Marcus explains.

Even the closing gifts reflect practical thinking. The Dillons receive quite a bit of vendor swag throughout the year, including high-end items from Canopy, Intuit, QuickBooks, ADP, and Double. Rather than letting these accumulate, they share them with the team.

“If you don’t have stuff like that laying around, I’m sure you can reach out to your partners, your technology partners, and they’ll send you some stuff to share with your team,” Marcus suggests.

Making It Work for Your Firm

The difference between retreats that drain resources and those that create momentum is intentional planning that starts months ahead, timing that respects your team’s reality, logistics that remove friction rather than create it, and transparency that turns information sharing into trust building.

Listen to the full episode of Who’s Really the Boss? for more advice for running a successful team retreat. Plus, Rachel offers to share DBA’s actual retreat agendas and planning templates with any firm owner or team member who reaches out. “Don’t feel like you have to reinvent the wheel,” she says. Email her at rachel@collective.com or use the contact form on their website.

As the Dillons have learned through nearly a decade of refinement, when you invest in getting retreats right, a two-day gathering can align and energize your team for the entire year ahead.

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.

Your Voice Assistant Works Today Thanks to Fraudsters Who Destroyed a $10 Billion Company

Earmark Team · January 28, 2026 ·

February 1998. Bill Gates, the richest man in the world, walks up the steps of a Brussels government building. He turns to wave at someone behind him, smiling as he faces forward again. Then it happens: a cream pie hits him square in the face. Then another. And another.

Just days earlier, Microsoft had invested $45 million in Belgian speech recognition company Lernout & Hauspie. The pie-throwing activist who orchestrated this pastry protest later described his feelings as “the exhilaration of victory, exquisite pleasure.” But the real mess Microsoft had just stepped into would prove far stickier than whipped cream.

In this episode of Oh My Fraud, host Caleb Newquist unravels one of tech history’s most fascinating fraud cases. It’s a story where revolutionary innovation and elaborate deception became so intertwined that even today, the technology you speak to through Siri carries the DNA of a spectacular Belgian scandal.

Two Guys, One Vision: Kill the Keyboard

In late 1987, two West Flanders natives started what seemed like an impossible mission: eliminating the computer keyboard. Jo Lernout, the visionary salesman, was a former teacher turned MBA who’d worked his way through sales positions at Merck and Wang Laboratories. Paul Hauspie was the detail-oriented worker type who’d inherited his father’s accounting firm but spent his spare time developing software.

Together, they founded Lernout & Hauspie Speech Products (L&H) in Ypres. While we take voice assistants for granted today, in the late 1980s, the idea that computers could be operated by voice alone was revolutionary.

The technology was groundbreaking. By 1997, their products could recognize more words than a standard collegiate dictionary. The system could even handle tricky sentences like “Please write a letter right now to Mrs. Wright. Tell her that two is too many to buy.” For the late 1990s, this was nothing short of miraculous.

But like many startups, the early years were brutal. Lernout and Hauspie proved resourceful in securing financing to keep the lights on, including from local residents and the Flanders government. But year after year, they plowed money into research and development while making virtually no revenue.

When Your Hometown Believes in You (Maybe Too Much)

The company’s roots ran deep into West Flanders soil. One account described it as “a company set up by West Flanders natives with West Flanders capital and a West Flanders mentality: work hard and smart, take well-calculated risks.”

Lernout and Hauspie genuinely wanted their success to benefit their home region. They helped create the Flanders Language Valley, convincing the government to make Ypres a tax haven for tech companies. Research grants flooded the area, spawning new businesses.

In 1994, when L&H needed more funding, they tapped into the locals with something called automatic convertible bonds. These were essentially IOUs that would turn into stock if the company ever went public. Through sheer personal will and persuasion, Lernout and Hauspie raised money from 600 small Flemish investors, each contributing an average of $33,000. These weren’t venture capitalists; they were farmers, grocers, and small traders betting their savings on their hometown heroes.

The duo even approached a local pig farmer for investment. After hearing their pitch, he produced a half-eaten bank savings certificate worth about $60,000 that he’d salvaged after it was accidentally fed to his pigs. The farmer said if the bank would accept the damaged certificate, he’d let them invest the funds. After much convincing, the bank took it.

The technology started attracting serious attention. AT&T invested $10 million in 1993. Intel put in $30 million. Then came Microsoft with $45 million in early 1998, with their chief technology officer declaring they were “taking a big leap forward in transforming that vision into a reality.”

The company went public on the Nasdaq in November 1995 at $12.50 per share, despite skepticism from analysts who worried the technology was still too primitive. But beneath this genuine innovation and community support, troubling signs were already emerging.

The Art of Moving Money in Circles

As L&H struggled to generate revenue, it constructed an increasingly complex web of related-party transactions to maintain the illusion of explosive growth.

The centerpiece was the Flanders Language Valley Fund (FLV), co-founded and advised by L&H’s founders. This venture fund took a 49% stake in the Belgian unit of Quarterdeck Corporation, which just happened to be L&H’s largest customer, accounting for 30% of its revenue.

The new CEO of Quarterdeck was Gaston Bastien, a Belgian executive infamous for rushing Apple’s Newton operating system to market to avoid losing a wine cellar bet. The result was faulty handwriting recognition that disappointed consumers. Now he was running L&H’s biggest customer, which was partially owned by a fund controlled by L&H’s founders.

L&H also created something called Dictation Consortium to keep expensive R&D costs off its books while somehow claiming $26.6 million in revenue from this entity in 1996 and 1997. Who owned 61% of Dictation Consortium? The FLV fund. The other investors, according to Lernout, were “five or six people who were anonymous because they were rolled up into companies that were organized in Luxembourg and the British Virgin Islands.”

Even Microsoft threw $3 million into the FLV fund alongside their $45 million L&H investment, apparently missing these red flags entirely.

The Asian Revenue Miracle That Wasn’t

The real magic happened in Asia. In 1999, Bastien (now L&H’s CEO) claimed Asian sales had exploded to more than $150 million versus just $10 million the year before. Korean revenue jumped from $97,000 to $58.9 million in a single quarter—a mind-boggling 60,000% increase. Singapore contributed $80.3 million in 1999 after generating less than $300,000 the previous year.

But here’s where it gets weird. Singapore sales then mysteriously plummeted to $501,000 in the first quarter of 2000. Bastien had perfectly reasonable explanations for everything, of course. The company had sold licenses in Singapore that couldn’t be sold again. Korea had opened up thanks to an acquisition. Everything was great.

When Wall Street Journal reporters investigated these miraculous Asian numbers in August 2000, they uncovered a house of cards. Some companies that L&H identified as Korean customers said they did no business with the company at all. Others said their purchases were much smaller than L&H claimed. Only one customer would go on record confirming the numbers were accurate.

One major customer, Hung-chang Lin, supposedly doing between $5 million and $10 million in business with L&H, had a CEO who didn’t even know about the joint venture that was allegedly purchasing the products. When confronted about the discrepancies, L&H’s contact at Hung-chang admitted they had lied about everything.

The scheme involved creating sales agreements that let “customers” defer paying licensing fees until they made money from L&H’s products. The company booked these as sales anyway, then made deals with banks where the banks would take over the receivables in exchange for cash. L&H claimed these were sales of receivables, but they were essentially disguised loans.

The $100 Million That Vanished

The drama reached its peak in November 2000 when new CEO John Duerden flew to Korea to retrieve $100 million the company desperately needed to avoid bankruptcy. After waiting an hour, Duerden was grilling the Korean unit head about the missing money when three men kicked open the door, shouting and gesticulating before dragging the unit head out of the room.

Duerden fled the country, later telling the Journal, “The only thing I know for certain is that the money is not in the bank accounts.”

The end came officially on November 9, 2000, when L&H announced it would restate its financial filings due to “errors and irregularities.” The company admitted its third-quarter revenue would be about $40 million less than reported. Lernout and Hauspie resigned as executive co-chairmen, though they kept 30% of the voting rights. Weeks later, the company filed for bankruptcy. The stock that had soared to $72.50 in March 2000 (a 2,500% increase from its IPO price) was worthless. Ten billion dollars in market value had evaporated.

Justice came slowly. In September 2010, a full decade after the collapse, Lernout, Hauspie, and Bastien were found guilty in Belgium. Lernout and Hauspie each received five-year sentences with two years suspended. In December 2021, a Belgian court awarded 4,000 shareholders €655 million—but as one news source noted, “the compensation ruling is largely symbolic as the six former board members don’t have the financial means with which to pay it.”

The Technology Lives On (Under New Management)

Lernout maintains to this day, “The technology was real and great.” And he’s not wrong.

After ScanSoft acquired L&H’s assets from bankruptcy in 2001, the speech recognition technology began a remarkable journey. ScanSoft merged with Nuance Communications in 2005. By 2013, Nuance’s natural language processing algorithms, which were built on L&H’s foundation, powered Apple’s Siri. In spring 2021, Microsoft acquired Nuance for $19.7 billion.

The same technology that L&H claimed would revolutionize computing actually did—just not under their ownership. The speech recognition in your phone and the voice assistant in your home all carry the DNA of a company that destroyed itself through fraud despite having a product that actually worked.

Lessons for the Number Crunchers

For accounting professionals, the L&H case offers a masterclass in red flags:

Circular related-party transactions: When a company’s venture fund invests in its own customers, the revenue isn’t real
Explosive geographic revenue shifts: A 60,000% increase should trigger every skeptical bone in an auditor’s body
Anonymous investors in tax havens: Luxembourg and the British Virgin Islands aren’t known for transparency
Revenue recognition without cash: Booking sales to customers who don’t have to pay isn’t revenue; it’s fiction

As Newquist emphasizes, “It isn’t enough just to have a great product or just great tech. If you cook the books, it doesn’t matter how good your product is. Bad numbers are bad numbers, and people get real upset about bad numbers.”

The L&H story proves that no amount of revolutionary technology can overcome the fundamental truth of financial reporting: when you cook the books, everyone gets burned except, ironically, the technology itself, which lives on in every voice command you give your phone today.

Listen to the full Oh My Fraud episode to hear Newquist’s complete investigation into this cautionary tale. CPAs can earn free NASBA-approved CPE credits through the Earmark app while learning these crucial fraud detection lessons. And remember, if you win a wine cellar on a bet, make that idiot pay up.

Two Stories That Expose How Accounting Credentials Get Weaponized for Fraud

Earmark Team · January 28, 2026 ·

What happens when professionals look the other way? In this episode of The Accounting Podcast, Blake Oliver and David Leary dive into two jaw-dropping cases that show what happens when accounting credentials get tangled up with crime and fraud.

First, they discuss a Wall Street Journal investigation into Jeffrey Epstein’s inner circle that somehow flew under the radar until recently. Then there’s the startup founder who allegedly blew through $2.2 million in investor money on her wedding while pretending to be a CPA. Both stories raise serious questions about trust and accountability.

Epstein’s Financial Fixers

“Epstein wasn’t a one man operation,” Blake reads from the Wall Street Journal investigation. The convicted sex offender had help from his CPA, Richard Kahn, and lawyer, Darren Indyke, who kept his financial machine running for years.

The story starts with a letter Kahn wrote in 2016. He described a “very healthy marriage” between two women, saying he’d personally witnessed their passion for each other during meetings. He even had it notarized. But the marriage was fake. Epstein had pressured an American woman he’d abused into marrying an Eastern European woman to help with immigration papers. Kahn’s letter gave the scheme legitimacy.

David was baffled. “Has any other CPA on the planet been asked to write letters like this before for an immigration proceeding?”

Good question. This wasn’t normal accounting work.

Kahn became Epstein’s in-house accountant in 2005 after Epstein tried out three candidates from a recruiting firm. By 2008, Kahn and another accountant had set up HBR Associates, a firm with only one client: Jeffrey Epstein. Their office was a one-bedroom apartment in Epstein’s building, right across the hall from lawyer Indyke’s office.

Both men provided way more than typical professional services. They managed payments to women in Epstein’s orbit, covering doctor’s visits and rent. When banks cut Epstein off, they found new places to open accounts. They withdrew cash in amounts under $10,000 to avoid reporting requirements.

The money tells its own story. Between 2011 and 2019, Epstein paid Indyke over $16 million and Kahn more than $10 million.

“That’s a lot of money,” Blake notes. “That’s more money than you would expect to receive for those kinds of services.”

Both men claim they didn’t know about Epstein’s crimes. They say they never witnessed abuse and no one reported it to them. But neither was questioned by federal authorities during the Epstein-Maxwell investigation.

“That is insane to me,” David says. “How do you not question the CPA and the lawyer? That’s the inner circle.”

“This is the sort of thing that makes me think the conspiracy theorists are right,” Blake responds. “It just doesn’t compute.”

Now, Kahn and Indyke control Epstein’s estate as co-executors, managing assets worth over $100 million. They’re also beneficiaries of a trust that will collect whatever’s left after all claims are settled—potentially tens of millions each.

The Fake CPA’s $13 Million Con

The second story hits closer to home for the accounting profession. Shiloh Luckey founded a startup called ComplYant App, Inc. in 2019, positioning it as a tax compliance app for small businesses. She raised $13 million from venture capitalists, including a firm co-founded by David Sacks, cohost of the All-In podcast.

Luckey told investors the company was earning $250,000 in monthly recurring revenue. The actual number was $250. Not thousands. Just $250. The company averaged fewer than four new subscribers per month despite having about 50 employees.

Luckey allegedly represented herself as a CPA even though she wasn’t one. And according to the FBI and SEC, she spent $2.2 million of investor money on personal stuff, including a Caribbean wedding, a house, Super Bowl tickets, and luxury trips to Aspen, Miami Beach, Turks and Caicos, and Lisbon.

When ComplYant shut down in 2023, those 50 employees lost their jobs. They waited seven weeks for final paychecks and discovered their 401(k) contributions were missing.

The kicker? Luckey is currently on TikTok giving financial advice to nearly 24,000 followers. She’s even launched a new startup called HabitLoop, described as a digital financial assistant.

Other News From the Episode

The hosts also covered several other developments in accounting and finance, including:

Cannabis businesses can finally deduct regular business expenses now that marijuana is being reclassified as a Schedule 3 drug. Previously, they faced effective tax rates of 60-80% because they couldn’t deduct basic costs like rent and payroll.
Trump announced a new Tech Force that will hire 1,000 people to build AI infrastructure for the federal government, working with companies like Microsoft and Amazon.
Intuit partnered with Circle to integrate stablecoin payments into QuickBooks, potentially cutting out traditional banking rails for payments.
The IRS Criminal Investigations unit identified over $10 billion in financial crimes this year, including $4.5 billion in tax fraud.
A lawyer is suing the IRS to recognize her golden retriever as a tax dependent, arguing the dog meets every requirement except being human.

The Bigger Picture

What’s striking about both main stories is how they expose vulnerabilities in the accounting profession’s trust-based system. In one case, a real CPA operated at the center of a criminal enterprise while claiming ignorance. In the other, someone falsely claimed CPA credentials to defraud investors.

As Blake pointed out about the Epstein investigation: “It just doesn’t compute.”

These stories are reminders that the accounting profession’s credibility can be weaponized, either by those who hold credentials and choose to look the other way, or by those who fake credentials to exploit the trust that comes with them.

Listen to the complete episode of The Accounting Podcast for more, including details about AI-powered invoice fraud and why white-collar workers are getting nervous about their job prospects.