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Caleb Newquist

Three Fraud Schemes, Two Decades, and a Quarter-Billion Dollars in Stolen Money

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On January 20, 2021, the last day of Donald Trump’s first presidential term, Eliyahu “Eli” Weinstein got a phone call that would rank among the best days of anyone’s life. The President of the United States had commuted his sentence, freeing him after eight years of a 24-year prison term for running a $200 million Ponzi scheme.

Six months later, he was already planning his next fraud.

In this episode of Oh My Fraud, host Caleb Newquist traces the jaw-dropping story of a fraudster who got a presidential second chance and immediately used it to steal another $44 million. It’s a tale that spans two decades, three separate fraud schemes, and over a quarter-billion dollars in losses.

The Community Leader Who Betrayed Everyone’s Trust

Eli wasn’t some shadowy figure operating from the margins. He was a pillar of the Orthodox Jewish community in Lakewood Township, New Jersey—home to Beth Medrash Govoha, the largest yeshiva outside of Israel. The son of a Jewish community leader and school principal from Brooklyn, Eli was known for his devout faith and generous donations to religious organizations. He spent millions on Judaica, Jewish devotional artwork and artifacts.

Starting around 2004, Eli began raising money for real estate deals. His pitch was simple: he had access to below-market properties, could flip them quickly to developers he had lined up, and everyone would make guaranteed returns with little risk. In the tight-knit Orthodox community, where deals often happen on handshakes with minimal paperwork, a respected leader’s word was his bond.

According to the 2011 federal indictment, just three investors—two in the UK and one in Bronxville, New York—put in over $136 million. The total losses exceeded $200 million.

The details in the indictment would be darkly funny if real people hadn’t lost everything. Eli raised $5.4 million for a project involving a national supermarket chain in Trotwood, Georgia. The only problems were there is no Trotwood, Georgia, and the supermarket chain had never heard of him.

Then there was the widow in Los Angeles who worked to help orphaned and poor children in Israel. Her dream was to open a music school for these kids. Eli convinced her to give him $1.2 million, promising to repay it in three weeks with interest. When she emailed asking him to “stop screwing around” and return her money, Eli’s response was two words: “f— you.”

He told a widow who helps orphans to go *$#%! herself.

But wait, it gets worse. When meeting with one victim’s representative, Eli asked what the representative’s wife and Eli had in common. When the man said he didn’t know, Eli replied, “We both f***ed you.”

The Judge Saw Right Through Him

At sentencing in February 2014, Judge Joel Pisano didn’t mince words. “You are a cheat. You lied and your deception is relentless. You’re consumed by deception.” He sentenced Eli to 22 years in prison, plus $250 million in restitution and $215 million in forfeiture.

But Eli couldn’t stop, even while awaiting trial. In February 2012, already under indictment, he started pitching investors on pre-IPO Facebook shares and Florida real estate he didn’t have. He used the money he raised to pay his lawyers for the fraud case.

That earned him an additional 24 months, bringing his total sentence to over 24 years. By white collar crime standards, it was harsh. But Eli had something most convicted fraudsters don’t: connections to people who could get his case in front of the President.

A Second Chance Immediately Squandered

The campaign for Eli’s clemency was well-organized. Criminal justice reform advocates argued his sentence was excessive. The White House statement noted that “numerous victims had written in support” and emphasized his seven children and loving marriage.

On Trump’s last day in office, he granted clemency to more than a dozen people facing fraud charges, which was a dramatic break from historical norms. As Caleb notes in the episode, white collar criminals were “very infrequently chosen for clemency” before Trump.

By July 2021, just six months after his release, Eli was building his next scheme. But his name and face had been everywhere. So he became “Mike Konig.”

The vehicle was Optimus Investments, Inc., supposedly dedicated to brokering deals on personal protective equipment (PPE) like masks, gloves, and hand sanitizer. This was mid-2021, when COVID supplies were still the hottest commodity on earth. “Mike Konig” claimed to have networks of government agencies, Turkish factory owners, and Israeli lawyers. He was always cagey about details. If everyone knew his contacts, he said, they could “reverse engineer him out of business.”

Richard Curry and Christopher Anderson started Tryon Management Group to raise money for these deals, eventually bringing in tens of millions. Investors received regular updates with videos of factories producing masks. “This is something that potentially has major legs,” Curry wrote enthusiastically.

Except almost none of it was real.

The Elaborate COVID Con Unravels

The deception was breathtaking. They hired temporary staff to pretend to be factory workers for videos. Someone in Vietnam procured just enough medical gear to fill a few kits for show. They purchased 5,000 empty boxes, wrapped them, and put them on pallets to represent orders.

The red flags were everywhere. A spreadsheet of Optimus’s expenses included a line reading “mystery expenses” next to $41,028,233.05. As Caleb observes, “A company dealing in medical supplies should not have mystery expenses. The only type of business that should have mystery expenses is whatever Scooby-Doo and the gang are always up to.”

Everything unraveled when Alaa Hattab, an Optimus associate, accidentally revealed the truth to Curry and Anderson. The baby formula deal was fake. The biggest mask deals were fake. The first aid kit deal was also fake.

Then came the bombshell: Mike Konig was actually Eli.

Curry and Anderson confronted him with hidden recording devices. On tape, Eli admitted, “I finagled and lied to people to cover us.” Then he asked them to keep his secret and help him continue. Incredibly, they agreed—at least temporarily.

By November 2022, with inflation surging and investors demanding their money, Tryon halted redemptions. When investors compared notes and found inconsistencies, one filed an SEC whistleblower report. The FBI arrested Eli at his home on July 18, 2023.

The Lessons for Accounting Professionals

After a seven-week trial, Eli was convicted in 2025 of securities fraud, wire fraud, money laundering, and conspiracy. In November 2025, he received a 37-year sentence. Over two decades, he had stolen more than a quarter-billion dollars.

Yitz Grossman, who had championed Eli’s clemency, told Bloomberg, “I still feel sick and embarrassed to speak with some of these people who gave me a letter to help out this family. My conclusion is he’s sick and he can’t control himself. He’s a deal junkie. He thinks he’s smarter than everybody else.”

This case is a reminder to accounting professionals and fraud examiners to look out for red flags appear over and over again, like:

  • Guaranteed returns with little risk
  • Short turnarounds that seem too good to be true
  • Minimal documentation or transparency
  • “Mystery expenses” in the tens of millions
  • Deals involving places that don’t exist

It also highlights how affinity fraud remains devastatingly effective because it weaponizes the trust that holds communities together. Eli’s victims trusted someone who demonstrated a commitment to their shared values.

On the political front, Obama’s administration created the Financial Fraud Enforcement Task Force in 2009 to prosecute financial crimes. Trump terminated it and replaced it with his own version. As Caleb observes with characteristic bluntness, Trump is “mercurial, petty, vindictive” and wouldn’t be above granting clemency to people Obama prosecuted simply because Obama prosecuted them.

The broader lesson is that when we reserve mercy for the wealthy and connected while ordinary offenders remain incarcerated, that’s not mercy at all. “That’s callous. That’s malevolent. And now maybe it’s American,” Caleb says. 
Eli’s lawyer maintains his innocence and will appeal.

Listen to the full episode of Oh My Fraud to hear all the jaw-dropping details, damning quotes from court documents, and Caleb’s sharp commentary on what this case reveals about fraud, mercy, and American justice. Because when someone uses a presidential pardon to immediately start stealing again, we all need to pay attention.

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

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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.

When 37,000 Japanese Investors Discovered Their Dividends Were Now “Divine”

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Picture opening your quarterly dividend envelope in February 2007, expecting yen, one of the world’s most stable currencies, but instead finding paper vouchers denominated in “Enten,” which literally means “divine money” in Japanese. These heavenly tokens were only good in one man’s bizarre marketplace where you could buy bedding, socks, and produce, but definitely couldn’t pay your rent.

This actually happened to 37,000 Japanese investors who discovered their life savings had been converted into monopoly money.

In the latest Oh My Fraud episode, “Divine Yen, Devilish Fraud,” host Caleb Newquist unpacks one of Japan’s most absurd financial frauds. The story of Kazutsugi Nami and his Ladies & Gentleman company—yes, that was the actual name—offers critical lessons for accounting professionals in a time of growing cryptocurrency schemes.

A Career Built on Fraud

You might think a fraud conviction would end someone’s career in finance. Kazutsugi proved otherwise, repeatedly.

His criminal timeline reads like a fraudster’s greatest hits. In the 1970s, as vice president of APO Japan, he helped market fake exhaust gas removers through a pyramid scheme. The devices didn’t work, but 250,000 people bought in before the company went bankrupt and authorities came knocking.

Most people would have learned their lesson. Not Kazutsugi.

By 1973, he’d already founded Nozakku Co., selling “magic stones” that supposedly purified tap water. The timing was perfect, as Japan faced severe water contamination from rapid industrialization, and desperate people wanted solutions. At its peak, Nozakku pulled in roughly ¥2 billion annually (about $6-8 million in late 1970s dollars). The stones weren’t magic. They didn’t purify anything. By 1978, Kazutsugi was in prison for fraud.

In a move that should make every accounting professional pause, in 1987, while his fraud record was still fresh, Kazutsugi founded Ladies & Gentleman (L&G). Eventually, 37,000 investors would hand over billions of yen to a convicted fraudster. One victim later justified their investment because L&G had been “in business for a long time.”

The bizarre culmination came on February 4, 2009, when police arrived to arrest him. Instead of hiding, Kazutsugi held court at a restaurant, charging reporters ¥10,000 each to attend his breakfast press conference while he sipped beer at 5:30 AM. He’d even packed spare underwear, expecting the arrest.

When asked about defrauding investors, his response was pure theater. “Do you think I could behave openly like this if there had been a fraud?” Later, he added, “Time will tell if I’m a con man or a swindler.”

The Divine Currency Revolution That Wasn’t

Kazutsugi didn’t just promise returns; he promised revolution. He called Enten the future of money, a currency that would break free from Japan’s economic system. He claimed governments would eventually adopt it and that he had a divine decree to eliminate poverty worldwide.

At investor events that resembled religious revivals, Kazutsugi styled himself as a modern-day Oda Nobunaga, one of Japan’s great historical figures, who unified Japan through military conquest in the 16th century.

The 36% annual returns Kazutsugi promised should have been an immediate red flag. In 2007, when Japanese government bonds yielded around 1.5%, 36% guaranteed returns defied financial gravity. Yet thousands of investors, many elderly and seeking retirement security, handed over their savings.

The scheme’s genius was its gradual escalation. Initially, L&G paid dividends in real yen, establishing trust. Then in early 2007, dividends became partially Enten. Finally, they were paid entirely in this imaginary currency that could only be spent in L&G’s internal marketplace, essentially a curated flea market offering comforters, vitamins, and produce.

As Caleb observes in the episode, these are exactly the products “multi-level marketing companies love because you can just claim it’s enhanced by whatever mystical bullshit you are selling that year.”

When Vision Meets Delusion

During the episode, Caleb and producer Zach Frank explore fascinating parallels between cult leaders and modern tech CEOs. Both sell transcendent visions that attract devoted followers.

“They see themselves as right. They’re cocky, they know the way, and they’re the only ones who know the way,” Zach observes.

This absolute certainty becomes magnetic. Caleb notes how Elon Musk, before his political involvement exposed his character. “He had this vision for the world. We’re going to Mars and we’re going to save the world. And people are like, yeah, I’ll follow you anywhere.”

Zach offers crucial insight about why these figures gain traction. “We’re in a time where gurus are becoming more popular than ever. It has to do with the lack of trust in institutions and science in general. People want to find someone to give them the answers to everything.”

When traditional systems seem to be failing, like during the 2007-2008 financial crisis when L&G was collapsing, the person who claims to have all the answers becomes irresistibly attractive.

The Spectacular Collapse

When L&G announced dividends would only be paid in Enten—no more real yen—investors understandably panicked. Some wanted to know whether they could exchange Enten for things like rent and food. They could not.

Like a classic bank run, investors crowded outside L&G locations demanding money and answers. The Japanese press pounced on the story. In November 2007, L&G filed for bankruptcy with estimated losses between ¥126 billion to ¥226 billion (roughly $1-2 billion USD). It was rumored to be Japan’s largest consumer investment fraud ever.

Even as police led him away, Kazutsugi insisted, “I am the poorest victim. Nobody lost more than I did.”

In March 2010, Kazutsugi was sentenced to 18 years in prison, a harsh sentence by Japanese standards. Even then, he insisted Enten was the future.

Lessons for the Profession

For accounting professionals, these patterns translate into specific warning signs:

  • Gradual shifts in payment methods that move from standard to non-standard practices
  • Closed ecosystems where value can only be realized within the company’s control
  • Recruitment-based growth models dressed up as community building
  • Attacks on regulators rather than substantive responses to concerns
  • Appeals to revolution that discourage traditional due diligence
  • Impossible guaranteed returns justified by proprietary methods

Distinguishing between legitimate innovation and sophisticated fraud requires more than technical knowledge; it requires understanding the psychology of persuasion.

Real innovations might disrupt industries, but they don’t violate mathematical laws. A 36% guaranteed return isn’t innovation; it’s impossibility. A currency that only works in one company’s marketplace is company scrip, a practice outlawed in most developed nations for good reason.

As Caleb warns, “If someone promises you a 36% annual return, but that return comes back to you in tokens that are only good for bedsheets, fruits, and the occasional pressure cooker, you are not diversifying your portfolio. You are subsidizing a cult with slightly better stationery.”

Listen to the full Oh My Fraud episode to hear the complete breakdown of this bizarre case, including more details about the victims and the reasons smart people fall for obvious frauds. The episode offers insights that connect historical frauds to modern schemes and the psychological vulnerabilities that transcend cultures and currencies.

Whether it’s cryptocurrency, NFTs, or the next financial revolution, the pattern persists: charismatic leaders promising transformation, impossible returns dressed as innovation, and schemes that create confusion where clarity is desperately needed. Our role as accounting professionals is to ensure that when someone claims to be building the future, they’re working with real materials, not divine intervention.

Ancient Fraudsters Wrote the Playbook Modern White-Collar Criminals Still Follow

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Picture a man frantically sawing through the bottom of his own ship in the middle of the Mediterranean Sea. Passengers rush below deck to find him red-handed, hole half-cut, wood shavings floating in the rising water. A chase ensues. The would-be fraudster, cornered and desperate, hurls himself into the ocean rather than face justice.

This isn’t a Netflix true crime series; it’s a 2,300-year-old insurance fraud that went spectacularly wrong.

In the latest episode of Oh My Fraud, host Caleb Newquist takes listeners on a journey through time to explore some of history’s earliest recorded financial frauds. Fresh from his European travels (with a particular fondness for Budapest’s goulash and Vienna’s coffeehouse culture), Caleb digs into ancient schemes that prove creative accounting isn’t a modern invention.

When Rome Literally Auctioned Off the Throne

The Year of Five Emperors in 193 reads like a corporate governance nightmare. It started with Emperor Commodus getting assassinated on New Year’s Eve 192 and creating what Caleb calls “quite an exciting start to the year 193.”

His successor, Pertinax, took the throne with big plans to reform Rome’s finances, which Commodus had left in ruins. Think of him as the turnaround CEO brought in after a spending spree. His first move was cutting the donativum, the cash gifts emperors traditionally paid to the Praetorian Guard when taking power.

Bad idea. The Praetorian Guard, Rome’s elite military unit responsible for protecting the emperor, didn’t appreciate their bonus getting slashed. When Pertinax’s follow-up offers still fell short, around 300 guards stormed the palace. After what Caleb imagines as “a very brief conversation,” they assassinated him. His entire reign: 87 days.

What happened next defies belief. The Praetorian Guard auctioned off the throne to the highest bidder. Marcus Didius Julianus won and became emperor, essentially purchasing the Roman Empire like buying a company at auction. But word quickly spread about how he got the throne. Three influential generals rebelled and claimed it for themselves. Within 66 days, Julianus was assassinated, ending one of the shortest reigns in Roman history.

The parallels to modern corporate fraud are hard to miss. We’ve seen executives obtain positions through financial manipulation and insider dealing. The donativum system itself mirrors modern bonus structures that create dangerous dependencies. When those bonuses get cut, whether in ancient Rome or on Wall Street, the backlash can destroy companies and careers.

The World’s First Insurance Fraud Goes Sideways

If the Roman story shows political corruption at its worst, ancient Greece produced the world’s first recorded insurance scam in 360 BCE. Meet Hegestratos, a sea merchant with a plan that was elegant in its simplicity and spectacular in its failure.

To understand the scheme, you need to understand bottomry loans. Back then, sea travel was genuinely terrifying. Ships sank all the time. Bottomry allowed merchants to borrow money using their ship and cargo as collateral. If the vessel reached its destination, the merchant sold the cargo, repaid the loan with interest, and kept the profit. If the ship sank, the lender ate the loss. It was proto-insurance built on trust that merchants wouldn’t deliberately sink their own vessels.

Hegestratos saw opportunity where others saw protection. He and his coconspirator Zenothemis took out a bottomry loan for a grain shipment from Syracuse to Athens. But instead of using the money properly, they immediately sent it to Massalia (modern-day Marseille). They planned to sail for a few days, scuttle the ship, claim tragic loss at sea, and keep both the loan money and the grain.

Two or three days into the voyage, Hegestratos decided it was showtime. He snuck below deck and began cutting a hole in the ship’s hull. Meanwhile, Zenothemis stayed topside, supposedly creating a diversion.

But as Caleb hilariously reimagines it, Zenothemis was terrible at his job. Picture him “fake coughing every time there’s a loud noise from down below” while other passengers, who already didn’t like him, grew suspicious. The cutting was loud. The diversion was pathetic. Soon, passengers rushed below to find Hegestratos literally caught red-handed.

What followed was pure slapstick. Caleb envisions it as “one of those Keystone Cops chase scenes with Yakety Sax playing behind it.” Hegestratos flees through the ship, passengers in hot pursuit, ending with the fraudster hurling himself into the Mediterranean. As the ancient orator Demosthenes recorded, “Thus miserable as he was, he met a miserable end as he deserved, suffering the fate which he proposed to bring about for others.”

You’d think watching your partner drown would inspire some soul-searching. Not Zenothemis. With remarkable audacity, he tried to continue the fraud. He actually asked the crew to sink the ship anyway, arguing that “all hope was lost.”

When that failed and they limped to shore at Cephallenia, there was a dispute. Protus, the “supercargo” responsible for the grain reaching Athens, wanted to continue there. Zenothemis insisted they go to Massalia, claiming connections to the deceased fraudster and the original lenders. The local magistrates sided with Protus. They ordered the ship to Athens, where Zenothemis filed lawsuits claiming ownership of the grain.

The Mystery Ending That Still Bugs Historians

The frustrating part of this story is we don’t know how it ended. The original documents were “mutilated,” leaving only 32 paragraphs that “yielded no satisfactory sense” about the final verdict.

This uncertainty has sparked debate for centuries. John M. Zane’s 1925 Michigan Law Review analysis offers a twist: maybe Zenothemis wasn’t a coconspirator but another victim. Zane points out that Zenothemis had no access to the redirected money, no legitimate claim to sell the cargo, and nothing to gain from the ship sinking. Maybe he desired to return to Massalia because he genuinely wanted to collect insurance to repay his lender friends.

Zane even suggests that if it went to trial, the rich lenders probably lost because Athenian juries were populist and unsympathetic to wealthy plaintiffs, a dynamic that sounds familiar to anyone following modern white-collar crime prosecutions.

Whether Zenothemis was a fraudster or a fool, the case establishes a principle fundamental to financial law: fraudulent contracts are void. This ancient precedent echoes through centuries of case law and continues protecting victims today.

Ancient Schemes, Modern Lessons

As Caleb notes, there are no new frauds, just new fraudsters. The schemes evolved from bottomry loans to blockchain, from cutting holes in ships to cutting corners in compliance, but the patterns remain:

  • Exploiting trust. Bottomry loans worked because people trusted merchants wouldn’t sink their own ships, just as modern systems assume executives won’t tank their own companies
  • The coconspirator problem. Hegestratos learned fatally that complex fraud needs help, yet every additional conspirator multiplies detection risk
  • Documentation dilemmas. Even in 360 BCE, fraudsters needed false paperwork and had to manage competing claims
  • Greed override. Both cases show how easy money overrides rational risk assessment

Caleb’s observation about creating diversions particularly resonates: “You cannot have any weak links in your conspiracy. Don’t think you can just let some hack create a half-assed diversion for you.” His reimagining of Zenothemis’s pathetic distraction attempts—fake coughing to cover ship-cutting sounds—reminds us that fraud often fails not in conception but in execution.

For CPAs and fraud examiners, these aren’t just historical curiosities; they’re training exercises in pattern recognition. The executive inflating revenues for bonuses follows Julianus’s playbook. The insurance fraudster staging accidents mirrors Hegestratos’s scheme. Understanding these patterns helps professionals spot red flags before they become scandals.

The Timeless Blueprint of Financial Deception

From emperors buying their positions to merchants attempting insurance fraud, these ancient cases reveal that financial deception is as old as commerce itself. The schemes involved ships instead of spreadsheets, cargo instead of cryptocurrency, but the underlying patterns of exploiting trust, creating false documentation, and letting greed override judgment haven’t changed.

For today’s accounting professionals, these historical frauds serve as cautionary tales and educational tools. That executive oddly eager to bypass controls? They’re following Julianus’s playbook. That unusual insurance claim with convenient timing? It echoes Hegestratos’s bottomry loan scheme. The vendor insisting on redirecting payments? They’re pulling a move as old as Massalia.

What makes these ancient frauds valuable is their stripped-down simplicity. Without modern financial instruments and digital smokescreens, we see the raw mechanics of deception. The Praetorian Guard’s throne auction isn’t fundamentally different from a board being bought off; it’s just more honest about the transaction.

Listen to the full episode of Oh My Fraud to hear Caleb bring these ancient frauds to life with his signature blend of historical detail and irreverent humor. Because sometimes the best way to understand today’s financial crimes is to study the fraudsters who wrote the original playbook over two millennia ago.

When Bots Listen to Robots and Real Money Disappears

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Picture this: a computer on stage playing songs to an audience of computers. No humans involved, just machines performing for machines in an endless digital loop. Yet somehow, millions of dollars change hands.

This isn’t science fiction. It’s happening right now on streaming platforms, and it’s just one of the mind-bending fraud schemes explored in this episode of Oh My Fraud. Host Caleb Newquist opens with a relatively new conspiracy theory called the Dead Internet, which suggests that most online activity, including posts, likes, followers, and streams, isn’t human anymore. It’s “bots talking to bots, talking to bots,” creating an information superhighway filled with self-driving cars that have destinations but no passengers.

But what happens when someone exploits this artificial ecosystem for real money? That’s exactly what we’re about to find out.

The $121 Million Email That Fooled Silicon Valley

Between 2013 and 2015, a Lithuanian man named Evaldas Rimašauskas pulled off something that shouldn’t have been possible. He convinced two of the world’s smartest companies, Google and Facebook, to wire him $121 million. His method wasn’t sophisticated hacking or complex algorithms. He simply pretended to be someone else.

Rimašauskas impersonated Quanta Computer, a real Taiwan-based hardware manufacturer that actually did business with both tech giants. He set up a company in Latvia under Quanta’s name and opened bank accounts in Latvia and Cyprus. Then his team got to work, calling Google and Facebook customer service lines to gather intelligence, including names of key employees, contact information, and other details that would make their lie believable.

Through phishing emails and what Caleb describes as “a maze of phony invoices, contracts, letters, and corporate stamps,” Rimašauskas created enough confusion to convince someone at Google to update the bank account they had on file for Quanta Computer. In 2013, Google sent $23 million to his account. Two years later, using the same playbook, Facebook wired him $98 million.

The money flowed through accounts across Latvia, Cyprus, Slovakia, Lithuania, Hungary, and Hong Kong. And here’s the kicker: these amounts were so insignificant to Google and Facebook that they “went virtually unnoticed.” As Caleb puts it, “$23 million and $98 million aren’t even rounding errors on the amount of revenue for Google and Facebook. It’s less than pocket change.”

Eventually, someone at Google caught on. Rimašauskas was arrested in March 2017, extradited to the U.S. that August, and pleaded guilty to wire fraud in March 2019. He got five years in prison, and both companies got their money back.

From IT Mogul to Music “Producer” to Alleged Fraudster

Our second story shifts from simple impersonation to something far stranger. Meet Michael Smith, a 52-year-old with a resume that reads like three different people’s lives smashed together.

According to the research, Smith made his first fortune in the 1990s with an IT business where he allegedly wrote “one of the main fixes for the Y2K millennium software bug.” He then ran chains of medical clinics, which landed him in trouble in 2020 when he and two associates paid $900,000 to settle Medicare and Medicaid fraud allegations.

But here’s where it gets weird. At age 39, Smith decided to become a music industry player. Despite having no apparent musical background, he somehow ended up judging a BET hip-hop competition called “One Shot” alongside DJ Khaled, T.I., and Twista. As Wired magazine described it, he was “a relatively unknown record producer with a checkbook” among actual stars.

When Caleb asked producer Zach Frank if he’d ever heard of anyone building a successful music career starting in middle age, Zach’s response was telling: “It’s extremely, extremely rare. Not without money, at least.”

The Streaming Revolution and Its Discontents

To understand Smith’s alleged fraud, you need to understand how dramatically the music industry has changed. Zach, who comes from a family of professional musicians, explained how streaming completely upended the business model.

In the old days, people bought physical albums for $12-15 at stores like Tower Records. Artists made real money from album sales. Then came Napster and peer-to-peer sharing, which Caleb admits using extensively in college. “People were listening to all this music completely in its entirety for free,” he recalls.

Today’s streaming platforms like Spotify and Apple Music operate on a subscription model. Users pay monthly fees for unlimited access, and artists get fractions of pennies per stream. Spotify made $17 billion in 2024 and claims 70% goes to the music industry, but individual artists see almost nothing.

The numbers are staggering. According to Spotify’s former chief economist, more music is released every single day in 2025 than in the entire year of 1989. And here’s what makes it worse: bigger artists negotiate better deals, while smaller artists, as Zach puts it, “get screwed.”

Building an Army of Fake Listeners

This is the landscape Smith allegedly decided to exploit. Starting in 2017, he orchestrated what the Department of Justice calls a scheme to steal millions in royalties by fraudulently inflating music streams.

The mechanics were brilliant in their simplicity. First, Smith created thousands of bot accounts using fake email addresses and names. He even told a coconspirator to “make up names and addresses” but to “make sure everyone is over 18.” He paid $1.3 million in subscription fees because, as Zach explains, paid subscribers generate higher royalty rates than free users.

By October 2017, Smith had 1,040 bot accounts spread across 52 cloud service accounts. Each bot could stream about 636 songs per day, generating approximately 661,440 total daily streams. At half a cent per stream, that meant $3,307 daily, $99,000 monthly, or $1.2 million annually.

But Smith had a problem: he needed content. Lots of it.

When AI Makes Music for Bots to Hear

Initially, Smith used music catalogs from coconspirators and even tried selling his streaming service to other musicians desperate for plays. But as he wrote in May 2019, “I can’t run the bots without content and I need enough content so I don’t overrun each song. If we get too many streams on one song, it comes down.”

His solution? Artificial intelligence. Smith partnered with Alex Mitchell, CEO of an AI music company called Boomy, who began providing thousands of AI-generated songs each week.

The song and artist names were gloriously terrible. Song titles included “Zygotic Washstands,” “Zygoptera,” and “Calvinistic Dust.” Band names ranged from “Calm Knuckles” to “Camel Edible.” As Caleb jokes, “I don’t know what camel edibles are. Perhaps they are THC gummies for camels.”

To demonstrate just how far AI music has come, Zach used Udio.com during the podcast to generate two complete songs about Oh My Fraud in just 10-15 seconds. The results were unnervingly good, professional-sounding tracks that could easily pass for human-created music. “There’s a lot of AI music on Spotify at the moment without people knowing it’s AI,” Zach notes.

Smith used VPNs to hide that all streams came from one location and spread activity across thousands of songs to avoid detection. When flagged for “streaming abuse” in 2018, he protested: “We have no intentions of committing streaming fraud.”

By February 2024, Smith’s scheme had generated 4 billion streams and $12 million in royalties.

Folk Hero or Fraudster?

The reaction to Smith’s indictment has been surprisingly divided. Some see him as a criminal who stole from real artists through the “stream share” system, where royalties are distributed based on each rightsholder’s proportion of total streams. Others view him as a folk hero exposing an exploitative system.

The case raises uncomfortable questions. When the band Vulfpeck released an album of complete silence and asked fans to stream it while sleeping—earning $20,000 before Spotify banned them—was that fraud or performance art? As Zach asks, “If someone’s playing blank music, who are they to say that’s not real?”

Smith has hired the prestigious law firm that defended Diddy and plans to fight the charges vigorously. This will be the first major streaming fraud case fully litigated, potentially setting precedents for how we define fraud in digital spaces.

What We Learned

As Caleb reflects at the episode’s end, these cases reveal something profound about our digital economy. Google and Facebook, companies worth trillions with founders worth hundreds of billions, got tricked by simple schemes. A middle-aged entrepreneur with a checkbook created a phantom musical empire that earned millions.

For accounting professionals, these are warnings about the future of fraud detection. When documentation can be perfectly faked, when bots are indistinguishable from humans, when AI creates content that only machines consume, traditional audit procedures become obsolete.

These cases force us to confront questions about power, technology, and authenticity in the digital age. When companies make billions while creators earn pennies, algorithms determine value instead of human appreciation, and the line between real and artificial completely disappears, that’s when people start rooting for the fraudsters. Not because they’re right, but because the system itself feels so wrong.

Listen to the full episode to hear Caleb and Zach grapple with these questions, including those AI-generated songs that sound disturbingly human. Because in an age where machines create for machines while extracting real value from real people, understanding these frauds helps preserve what makes us human in an increasingly artificial world.