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The IRS Now Knows Who’s Trading Crypto But Can’t Tell What Anyone Owes

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The IRS now knows who’s trading crypto, but it still can’t tell if anyone owes tax. That’s the reality of the new 1099-DA reporting system that just went live, and it’s about to affect every tax professional with crypto clients.

On a recent episode of the Earmark Podcast, host Blake Oliver sat down with Lawrence Zlatkin, Vice President of Tax at Coinbase, to explain what the new 1099-DA form reports, where the gaps are, and what changes Coinbase is pushing for in Washington. With a front-row seat to crypto taxation’s biggest challenges, Lawrence offered insight on where the system works (and where it doesn’t).

The problem is that the IRS’s new reporting brings crypto tax enforcement into the mainstream, but the underlying framework creates massive overreporting with little tax benefit. Treating stablecoins as property and requiring reports on tiny gas fees generates millions of forms that tell the government almost nothing about actual tax liability. Tax professionals must bridge the gap between what the IRS receives and what matters for computing taxes.

The 1099-DA: What’s There and What’s Missing

Think of the 1099-DA as crypto’s version of the 1099-B that brokers send for stock trades. The basic concept is familiar: the form goes to your client and the IRS, and the government matches what taxpayers report against what exchanges report. Tax pros have worked with this system for decades.

But this first-year version is bare-bones. As Lawrence explained, “We are implementing the system barely 18 months after Congress issued the regulations. The 1099-B system was developed over a period of five years, and even longer for gross proceeds.”

The result is a “skeletal version” that reports just two things: who the customer is and their gross proceeds from transactions. The critical missing piece is cost basis.

“We’re including basis for our customers for informational purposes, but that information is not actually going to the government,” Lawrence said. Next year, exchanges will start reporting basis, but only when they have it.

Blake walked through a simple example. Say your client sells Bitcoin for $100. The IRS gets a 1099-DA showing $100 in gross proceeds. But if your client bought that Bitcoin for $90, the actual taxable gain is just $10. That $10 is the only number that matters for taxes, but it’s invisible to the government this year.

The problem worsens with transfers between wallets and exchanges. When crypto leaves Coinbase for a self-custody wallet or another exchange, the basis tracking breaks. “The only person who knows what’s in a non-custodial wallet is you because you’re the owner,” Lawrence explained. When that crypto returns to an exchange, there’s no way to reconstruct what happened in between.

So what’s the point of all this reporting? Lawrence was candid. “The government’s concern has been that there’s been underreporting and noncompliance in the ecosystem generally. So what this achieves from their standpoint is they find out who’s really participating.”

Until now, the IRS’s only crypto signal was that checkbox on the 1040, which Lawrence diplomatically called “gobbledygook.” It asks about digital asset transactions. Now the IRS will see actual dollar amounts attached to names. They’ll spot whales with millions in proceeds. They’ll identify non-filers.

“There’s nothing nefarious or awful or evil about that,” Lawrence said. “It’s just that they will have that information they didn’t otherwise have before.”

The practical takeaway is, “you are in control of your tax data,” Lawrence emphasized. Clients who consolidate their activity on a single exchange will have better records. Coinbase provides transaction history and gain/loss data through its “position service.” But clients bouncing between exchanges and wallets need to maintain their own records. Nobody else can do it for them.

The Stablecoin Problem: When Property Isn’t Property

Missing basis data would be manageable if the tax framework made sense. It doesn’t, especially for stablecoins.

Since 2014, the IRS has classified all crypto as property rather than currency or cash equivalents. This includes stablecoins like USDC, which are designed to trade at exactly $1. Every time your client uses USDC, that’s a reportable disposition of property.

“Stablecoins are designed to be stable and consistent and traded at par with the US dollar,” Lawrence said. “99.9% of the time, it’s intended to trade within a fraction of a decimal of the US dollar. So in essence, we’re not reporting a gain or loss. So it’s over-reporting of data. There’s no fundamental purpose for that. I would argue that the only reason for that is surveillance.”

The scale is significant. Coinbase must report stablecoin transactions exceeding $10,000 to the government. Hundreds of thousands of customers received 1099s this year that include these transactions. And taxpayers must report even smaller amounts. Coinbase just won’t tell the IRS about those.

Blake offered his own example. Earmark uses USDC to pay vendors for international transactions where stablecoins are faster than traditional banking. Under current rules, every payment is a reportable property disposition. “It’s as if the IRS got every bank transaction,” Blake said. “Americans would never stand for that. We’d call that surveillance and overreach.”

Lawrence revealed this isn’t hypothetical. Five years ago, the Treasury Department proposed requiring banks to report credit card transactions over $10,000 in aggregate. “That was quashed for the reasons you just described,” he said. Yet here we are with stablecoins.

There’s a small silver lining. “The tax system is based on income. If there’s no gain or loss, there’s no taxable income, and there’s no penalty,” Lawrence explained. You can’t underpay taxes on zero gain. But the reporting requirement still exists.

De Minimis Madness: When Pennies Become Paperwork

Beyond stablecoins, tiny transactions that generate enormous paperwork are another reporting nightmare.

Gas fees, which are the network costs for blockchain transactions, often involve disposing of pennies or fractions of dollars worth of Ethereum. Each one is technically a property disposition that must be tracked and reported. Each might have actual (if microscopic) gain or loss.

The volume is staggering. Coinbase files millions of 1099-DAs containing hundreds of millions of underlying transactions that feed into Form 8949. Lawrence estimates that about half qualify as de minimis, meaning they’re essentially meaningless for tax purposes.

“We’re not going to pave roads and solve the deficit on the backs of de minimis reporting for crypto,” Lawrence argued. He’s pushing for a threshold below which transactions become exempt from reporting or taxation. Should it be $5? $50? $200? Should it be income-based or transaction-based?

“At what point do we stop requiring reporting for transactions?” Lawrence asked. “If the IRS gets bombarded with billions of transactions that are tiny in nature because people are required to report them, the system itself breaks.”

These billions of transactions are being reported today, and the IRS’s ancient computer systems must somehow process them all.

The Washington Agenda: Common Sense Reforms in Political Gridlock

Lawrence came with a clear policy agenda that included ten priorities, although the conversation covered highlighted six in detail.

Beyond stablecoins and de minimis thresholds, Coinbase is pushing for the following reforms:

  • Crypto lending should work like securities lending. “You’re not disposing of crypto because you’re going to get the same amount back,” Lawrence explained. Under current securities rules, that’s not taxable. Crypto should be the same.
  • Staking rewards timing. The IRS says rewards are taxable when received. Others argue they shouldn’t be taxed until sold. “That’s a source of friction and debate,” Lawrence noted.
  • Charitable deductions are perhaps the clearest absurdity. Donate over $5,000 in Bitcoin, and you need a formal appraisal. “You can type it in Google and get a Bitcoin price, just like you get the price of any stock or security,” Lawrence said. Bitcoin has “readily ascertainable fair market value.” The appraisal requirement is “ridiculous.”
  • Foreign investment rules. The US has safe harbors that allow non-US persons to trade securities through US brokers without triggering US tax. No equivalent exists for crypto. “We’re the best and safest market in the world,” Lawrence said. “We’d like to preserve that for crypto, not just for regular old investment assets.”

So why hasn’t anything passed?

“I’m cautiously optimistic,” Lawrence said. President Trump has been supportive. He met with Coinbase CEO Brian Armstrong last week. The White House issued a report on digital assets, including tax provisions. Treasury has been “by and large very supportive.”

But Congress is the bottleneck. The House is narrowly Republican-controlled, and crypto has become more partisan than it should be. “This should not be a partisan debate,” Lawrence insisted. “This ecosystem benefits Democrats and Republicans.”

The Clarity Act for crypto regulation is under discussion. So is broader tax reform. But as Lawrence diplomatically put it, “Things don’t move as quickly as we might like in Washington.”

What This Means for Tax Professionals

The picture Lawrence painted is clear, even if the rules aren’t. The 1099-DA tells the IRS who’s trading and how much, but it lacks the cost basis needed to determine actual tax liability. Tax professionals must fill that gap by reconciling gross proceeds against basis records scattered across exchanges, wallets, and spreadsheets.

Meanwhile, classifying stablecoins as property without de minimis rules creates millions of reportable transactions with zero tax consequences. It’s all noise, no signal.

The reforms Coinbase wants make sense. But with narrow Congressional majorities and partisan friction, don’t expect relief before next filing season.

The message for practitioners is crypto is no longer niche. With millions of 1099-DAs arriving and IRS matching letters sure to follow, you need to understand what these forms show, how to help clients track basis, and where the traps are. Firms that build this expertise now will serve a growing client base. Those who don’t risk being blindsided along with their clients.

“Everyone wants to talk about tax,” Lawrence joked at the start. By the end, it’s clear why. The intersection of crypto and tax is where innovation meets regulation, and right now, regulation is playing catch-up.

Listen to the complete episode of the Earmark Podcast for Lawrence’s full breakdown of Coinbase’s policy priorities and practical advice on basis tracking. You can earn free NASBA-approved CPE credit by listening and taking a short quiz at earmarkcpe.com.

Fake Auditor Conclusions, Fabricated Board Minutes, and the Growing Cracks in Accounting’s Trust Infrastructure

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A compliance startup allegedly sold hundreds of companies fake SOC 2 reports complete with made-up auditor conclusions and board meeting notes that never happened. In Florida, legislators nearly abolished the state’s Board of Accountancy entirely. And AI companies now run ads that sound exactly like QuickBooks marketing copy.

These are just some of the topics Blake Oliver and David Leary tackled in their latest episode of The Accounting Podcast. The hosts dug into stories that show the systems meant to ensure trust in accounting face threats from multiple angles.

The (Alleged) SOC 2 Scandal

“This is wild,” Blake said, thanking a listener for sending him a detailed investigation about Delve, a VC-backed compliance startup. The company allegedly created fake SOC 2 reports at scale, using what the hosts described as a disturbing playbook.

According to a Substack series Blake reviewed, Delve’s platform pre-populated everything from policies to evidence and even independent auditor conclusions. The company then allegedly routed these pre-written reports through audit firms that simply rubber-stamped them.

“These are allegations. I have not independently verified any of this,” Blake was careful to note. “This is a very in-depth Substack report by an anonymous poster. So we should take this with a grain of salt.”

But the details were alarming. The investigation claimed to find board meetings that never happened, security simulations that were never performed, and trust pages showing controls as “implemented” before any actual work was done. Companies had written policies claiming they had mobile device management, VPNs, and intrusion detection systems, even though they had none of these.

The author analyzed 322 public Delve trust pages and found that 321 showed the exact same SOC 2 control set, which seems odd for supposedly customized compliance programs.

“The logo you get is an AICPA logo, right? You’re getting a stamp of approval from the AICPA,” David said, cutting to the heart of the problem. “Is the AICPA checking on all these badges that are on company websites?”

Blake explained how easy it would be to game the system. “All you have to do is find a firm willing to sign off without actually doing the work,” he said, comparing it to the BF Borgers case in Colorado, where a CPA firm was caught signing off on audits it never performed.

“This is the problem with assurance,” Blake continued. “If you have a few bad actors willing to just sign off, sign off, sign off, they can make a lot of money. And how do they get caught? And if they get caught, what happens?”

Florida Almost Killed Its Board of Accountancy

While fake compliance reports threaten the profession from within, Florida’s legislature almost destroyed a key piece of regulatory infrastructure from the outside.

House Bill 607 would have eliminated the Florida Board of Accountancy along with other professional licensing boards as part of a sweeping deregulation push. The Florida Institute of CPAs called it “the most serious threat to the profession in decades.”

“How do you regulate the CPA in Florida?” Blake asked, explaining the stakes. Without a Board of Accountancy, there’s no enforcement mechanism, no oversight, and no one to investigate bad actors.

The bill moved quickly through two committees before being stopped. But victory came at a cost. To focus on defeating the bill, FICPA had to table its own effort to create alternative pathways to CPA licensure that would have allowed candidates to qualify with 120 credit hours instead of 150.

The irony wasn’t lost on the hosts. Florida was the first state to implement the 150-hour rule. Now, while about 30 states have approved alternative pathways, efforts to defend against total deregulation have sidelined reforms.

“We want to streamline licensure, but we don’t want it to go away,” Blake said. “We’ve got folks who want too much regulation, and then we’ve got folks who want no regulation. There’s got to be a middle ground here.”

David predicted this won’t be the last such attempt. “I imagine we’re probably going to see more pushes for this because people are going to want the big, huge AI companies to have their AI do CPA work without a license in the way.”

When AI Ads Look Like QuickBooks Ads

Speaking of AI companies, David discovered something unsettling through a targeted LinkedIn ad. Anthropic is marketing “Claude for Finance” using language that sounds exactly like traditional accounting software.

The ad promised to handle recurring financial workflows, organize receipts into clean spreadsheets, build quarterly revenue models, and cross-reference documents for month-end close.

“Third-party app developers and accountants and CPAs that use Claude essentially trained the model so they could just take everybody out of the middle,” David explained. He compared it to how the iPhone camera evolved. At first, you needed third-party apps for filters and editing. Now it’s all built in.

The hosts also discussed a Wall Street Journal article about how regular people are already using AI for tax work. Examples ranged from using Copilot to model Roth conversions to having AI explain confusing IRS notices. One person used Gemini to value charitable donations for their tax return.

“The takeaway is they’re avoiding getting an accountant or a tax professional,” David said bluntly.

But the technology isn’t perfect. One user found that Grok gave wrong answers about capital gains tax until he rephrased his question. A retired tax preparer tested ChatGPT on an IRS volunteer certification exam, and ChatGPT failed.

This leads to what David called the “fact check tax,” a term from Anthropic’s own survey. “An assistant that sounds sure but is often wrong forces you to treat everything as suspect. Instead of freeing attention, AI creates a permanent fact-check tax.”

The Bigger Picture

These stories paint a picture of a profession under pressure from multiple directions. Fake compliance reports undermine the attestation model. Deregulation efforts threaten the licensing framework. AI platforms are positioning themselves as replacements rather than tools.

As Blake noted about AI, “It’s going to be really hard for Intuit and Xero to keep up unless they’re just plugging into ChatGPT or into Claude. How can their own AI chatbots keep up with what these companies are doing, and how fast they’re developing?”

For accounting professionals, these are challenges that require attention and action. Listen to the full episode of The Accounting Podcast to hear Blake and David discuss these stories and more. 

Hidden Screens, Tax-Season Tequila Deliveries, And Other Things Only Women In Accounting Would Believe

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At 37, Questian Telka sat across from a male colleague who asked her something she’ll never forget: “How does it feel to be a woman and be past your prime?”

She looked him dead in the eye. “Past my prime? I haven’t even gotten close to hitting my prime yet.”

Seven years later, on her 44th birthday, the day this episode of She Counts aired, Questian’s confidence proved prophetic. Her experience, revenue, and boundaries are thriving like never before. As she puts it with perfect accounting humor, “I know in accounting, assets depreciate with age, but I prefer to think of myself as an asset whose value compounds over time.”

Welcome to a special birthday episode of She Counts, the real-talk podcast where hosts Nancy McClelland, CPA, and Questian Telka, EA, tackle heavy topics like imposter syndrome, glass ceilings, sexual harassment, burnout, and pricing disparities. But they also know their community needs something lighter. Tax season is brutal, politics are exhausting, and everyone is tired.

So they crowdsourced stories from women across the profession with one simple prompt: “You know you’re a woman in accounting when…”

The responses poured in, and they range from hilarious to infuriating. But they’re all relatable. These are funny stories to share over drinks, but also proof that the absurd experiences uniting women in this profession aren’t anomalies. They’re the norm. And when we finally start talking about them, we realize we’re not alone. In fact, we never were, and laughter might just be our best survival tool.

Conference Survival: A Full-Contact Sport

If you want to understand what it’s really like being a woman in accounting, skip the spreadsheets. Watch us pack for a conference.

Questian calls herself a “minimalist,” which made Nancy burst out laughing. “I love that you think of yourself as a minimalist,” Nancy said, remembering the first time she visited Questian’s hotel room at their very first conference together, the Bookkeeping Buds retreat. “There was stuff everywhere. There’s literally no physical space in this room that does not have something of yours on it.”

Questian’s conference arsenal includes a clothing steamer and multiple shoe options (conference shoes, dinner shoes, and, especially in Las Vegas, dancing shoes). She has a full makeup setup and safety pins. “Inevitably, somebody at the conference is like, ‘I need X, Y, Z.’ And I’m like, ‘I have it. What do you need?'” she explains. “I have safety pins. I come prepared.”

Nancy operates differently. Severe back issues mean she refuses to carry more than a carry-on. Her solution is a handwritten chart mapping every conference day, every event, every outfit, and every pair of shoes, all strategically planned for maximum reuse. “I am obsessed with having absolutely everything I need and not one thing more,” she says.

Except costumes. Nancy always packs costumes.

She has a piñata costume, which she wore in a photo with Leslie Odom Jr., who “did not say a word about it. He just smiled.” She also has a watermelon costume and an aerobics costume for leading conference rooms through “She Works Hard for the Money.” As she puts it, “Costumes are the one exception.”

The shoe situation deserves its own category. Lynda Artesani brings an entire extra suitcase filled with just shoes. Her conference bestie Matthew Fulton carries it for her. “Yep, that’s me. That’s my job. That’s why they call me the conference husband,” Matthew jokes.

Then there’s the survival kit problem. Conference rooms are either arctic or tropical, with no middle ground. Nancy brings handmade ponchos from her best friend, a fiber artist. Questian brings pashminas. In fact, it’s a good idea to have both a pashmina scarf AND a battery-operated fan in your conference bag. Because venue temperature control is, as the hosts put it, “unhinged.”

Despite the need for survival gear, conferences are where magic happens in the most unexpected places. Questian met her romantic partner in the Starbucks line at an accounting conference. Nancy met Misty Megia, founder of Theatre of Public Speaking, when Doug Sleeter literally dragged her down a hallway to join a secret flash mob that would “interrupt” the opening keynote, which Misty actually choreographed herself.

Ellen Oliver nailed what matters most when she said, “You know you’re a woman in accounting when you finally get to meet your internet friends in real life.”

These conference moments create the connective tissue of a community that might only see each other a few times a year. But the real gymnastics happen when you try to schedule your actual life around the profession’s demands.

When the Universe Ignores Your Busy Season Calendar

Questian’s first son was due on Christmas Day. Perfect timing, she thought, not for the holiday, but for the tax benefit. “Who wouldn’t?” she laughs. Plus, as an EA who doesn’t do taxes, her busiest month is January with 1099s, year-end closes, and grant reporting. A December baby would’ve been ideal.

The baby had other plans. He arrived two weeks late, smack in the middle of January chaos. “I was really annoyed,” Questian admits. Fortunately, January’s birthstone is garnet, which is her favorite. She had a ring made to commemorate it.

Not everyone gets thwarted by nature. Dr. Jackie Meyer, CPA, planned both her children’s births before busy season, and it worked. When people asked if she was timing it for the tax deduction, she said no. She was timing it so she could be in the office during tax season. Robina Bennion pulled off the same feat. When her grandmother warned, “You can’t plan your whole life,” Robina shot back, “Oh yeah, grandma, watch me.”

Then there’s Jean Zick, who walked to work nine months pregnant in a late-90s blizzard because wires had to be faxed. A client needed something, so she went. Nancy’s response captures what we’re all thinking: “Thank goodness for today’s remote workforce.”

The emotional toll runs deeper than logistics. Every January, Questian says, “I want to quit accounting.” She’s joking, but she’s also not. “I eventually get over it, but every year I’m like, I need to change careers.”

Nancy shared a meme that rewrites the old rhyme about days in months. “30 days hath September, April, June, and November. All the rest have 31, except for January, which has 426,913.” If you’ve lived through January in accounting, you know that number might be low.

The hosts voiced something every woman in the profession has felt when they said, “You’ve cried over something that had nothing to do with accounting. But it was definitely about accounting.” That breakdown over a spilled coffee during 1099 season? Yeah, that wasn’t about the coffee.

Some stories make you laugh until you realize they shouldn’t be funny at all.

The Absurd, The Infuriating, and The Too Real

Gail Perry, editor-in-chief of CPA Practice Advisor, shared a story that starts unbelievably and gets worse. She was her firm’s multi-state tax expert. A client came in with multi-state issues. She was the obvious choice for the meeting. Except the client insisted on working with a man.

The firm’s solution was to set up a physical screen in the conference room. Gail sat behind it, hidden, listening and taking notes while feeding information to a male colleague who pretended to have her expertise. They joked she was the Wizard of Oz behind the curtain. “At the time, we just thought he was a jerk,” Gail said. Nancy and Questian insist they “would have said no.”

The wardrobe calculations alone could fill a spreadsheet. One listener pointed out the mental drain of deciding what to wear. Is this too tight? Too casual? Will this invite the wrong attention? Questian added that a male colleague recently observed how much time women spend getting “presentation ready.” That’s time men use to actually advance their careers. “This was a man saying this to me,” she noted.

Another listener treats clothing as armor and calls her quarter-zip her protection for meetings with clients who try to look at her chest. She even has a custom field in her CRM to tag problem clients, like men who’ve leered or made passes. “You cannot make this stuff up,” Nancy said.

Another submission was blunt: “You know you’re a woman in accounting when your client texts you late at night trying to sleep with you.”

Not every story stings. Dawn Slokan was at her daughter’s dance competition, convinced she kept seeing ads for Avalara, the tax software. Why would a tax company sponsor a dance event? Turns out it was a skincare brand. Her brain just couldn’t leave work at work.

The takeout metrics tell their own story. Terr Saracino’s local restaurants know it’s tax season by the volume of orders alone. Nancy’s favorite pizza place once taped two plastic containers to her delivery box. Inside each was a shot of tequila. “They knew it was us and they knew it was tax season.”

The conversation shifted when they addressed their most-requested topic: menopause and perimenopause. Nancy went through early menopause around 40. Her doctor dismissed it, saying, “You’re too young” and put her on birth control instead. 

Questian shared that most doctors receive about one month of (optional) menopause training. For something affecting over half the population!

Building Community Through Shared Experience

The hosts introduced Shawn Simmons, Nancy’s best friend since college and a professor of communication design at Milwaukee Institute of Art and Design. At 54, after eight years navigating her own health journey with limited support, Shawn is using her sabbatical to research how design and fiber arts can help women find community around menopause.

“I had trouble finding people to talk to about it,” Shawn explained. “I didn’t have a lot of resources. So I decided to use graphic design and art to help people like me find a community and be able to talk about their experiences.”

She created a survey asking women 16 and older where they currently find support and where they wish they could. Shawn’s research revealed the awareness gap. When she called about hormone replacement therapy options, the women at both her insurance and pharmaceutical companies didn’t know what HRT was.

These Stories Aren’t Bugs. They’re Features

The episode makes crystal clear these are shared experiences. The woman next to you at the conference, behind the screen feeding answers, in the Starbucks line, or whose pizza place knows her tequila preference has her own version of your story.

When we speak these stories out loud, they transform from private frustrations into collective evidence that this profession still has work to do. But more importantly, they prove women in accounting have been doing that work all along with humor, creativity, and an impressive collection of conference survival gear.

The hosts ended with a quote from Betty White that captures the spirit perfectly. “It’s your outlook on life that counts. If you take yourself lightly and don’t take yourself too seriously, pretty soon you can find the humor in our everyday lives. And sometimes it can be a lifesaver.”

In accounting, humor is standard equipment. Right there with the pashmina and the battery-powered fan.

Listen to the full episode of She Counts, then head to the She Counts LinkedIn page to share your own “You know you’re a woman in accounting when…” moment. You’re not the only one. You never were. And now we have the stories to prove it.

How Tim Duncan and Stan Lee Lost $50 Million to People They Trusted Most

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By 2017, Marvel movies were dominating the box office. Multiple films in the global top ten, billions in revenue, a cinematic universe shaping pop culture like we’d never seen before. At the center of it all, at least symbolically, was Stan Lee. But that same year, his wife Joan passed away after nearly 70 years together, and suddenly decisions they’d been navigating as a team were landing entirely on him.

That same year, NBA legend Tim Duncan discovered his financial advisor of 20 years had been stealing from him for the last decade. Between these two cases, the damage exceeded $50 million, and not a single dollar was stolen by a stranger.

In the latest episode of Oh My Fraud, host Caleb Newquist revives the podcast’s popular “Defrauded Famous” series to examine how trusted insiders extracted tens of millions from two of America’s most recognizable figures. As Caleb puts it, these cautionary tales are reminders that “fraud usually comes from the inside.”

The Big Fundamental’s Big Loss

Tim Duncan wasn’t your typical NBA superstar. Five-time champion, two-time MVP, 15-time All-Star, and nicknamed “The Big Fundamental” for his unglamorous but devastatingly effective style. As Shaquille O’Neal wrote in his autobiography, “I could talk trash to Patrick Ewing. Get in David Robinson’s face. Get a rise out of Alonzo Mourning. But when I went at Tim, he’d look at me like he was bored.”

This wasn’t a guy with a garage full of Ferraris and a Bengal tiger in the backyard. Tim grew up in the U.S. Virgin Islands and planned to be a competitive swimmer until Hurricane Hugo destroyed his training pool. Basketball came later, but success came fast. He was the number one pick in the 1997 draft and won his first championship in his second season.

By the time he retired, Tim had earned well over $200 million in NBA contracts alone. And from day one, he’d been working with financial advisor Charles Banks IV.

Charles came from money. His father was president of Ferguson Enterprises, a major plumbing and HVAC distributor. Charles became president of CSI Capital Management, managing around $400 million for about 150 professional athletes. He was tall, bookish, a wine enthusiast who even co-owned Screaming Eagle Winery with billionaire Stan Kroenke. He positioned himself as someone who could connect clients with sophisticated opportunities beyond basic retirement planning.

For a pro athlete, that kind of help matters. As Caleb explains, NBA players face the “jock tax,” meaning they owe state income taxes in every state they play. A game in California? Taxed there. New York road trip? Taxed there too. With 80-plus games a season, sitting down to personally vet investment deals isn’t exactly practical.

The Trust That Turned Toxic

The turning point came in 2007 when Charles left CSI Capital Management. He never told Tim. Their formal advisory relationship had ended, but Charles kept approaching Tim with investments. And after 2007, Charles had an undisclosed ownership interest in each of them.

Take Le Metier de Beaute, a cosmetics company. Charles pitched it as profitable with $8 million in sales, claiming Kevin Garnett would also invest. Tim put in $1.1 million. In January 2013, an audit uncovered “accounting irregularities and possible fraud.” But Charles texted Tim a month later, “Need to update on a deal. All good news.” The company went bankrupt that September. Tim’s money was gone.

The biggest fraud involved Gameday Entertainment, a struggling sports merchandising company where Charles was chairman and held a controlling interest (facts he never disclosed to Tim). Charles convinced Tim to take out a $10 million line of credit, then loan $7.5 million to Gameday at 12% annual interest. He claimed another investor was putting in the same amount. That investor didn’t exist. Charles pocketed $225,000 in fees and skimmed $15,000 from each monthly payment for two years.

The most brazen move came during the 2013 NBA Finals. While Tim was playing Miami, Charles faxed him signature pages (not the full agreement) for what he described as an amendment that would “remove $1.5 million of risk for you.” He texted: “All great news. No downside.” In reality, Tim had just taken on $6 million in new liability while giving up his priority position as a creditor. Charles paid himself over $1.5 million from the proceeds.

Gameday’s own controller later testified it felt like Charles was using the company as “his personal piggy bank.”

Justice, Sort Of

Tim’s 2013 divorce led to the discovery. A new financial consultant found discrepancies everywhere, including unclear loans, missing documentation and undisclosed conflicts. The final tally showed Tim had invested $24.1 million with Charles and gotten back about $7 million, all from interest payments, not actual returns.

In September 2016, a federal grand jury indicted Charles on four counts of wire fraud. He pleaded guilty to one count and was sentenced to four years in federal prison plus $7.5 million in restitution. Federal investigators calculated Tim’s actual loss at $13.5 million. Tim himself estimated it closer to $25 million.

At sentencing, Tim told Charles directly, “I just wanted you to own up, pay up, and we’d move on. You wouldn’t. So now we’re here.” He also wrote to the judge, “You may not understand how difficult it is for me to be in the public light in this horrible way, as the poster child for a dumb athlete whose financial advisor took his money.”

Judge Fred Berry wasn’t sympathetic to Charles, comparing him to a drug dealer he’d sentenced earlier that day. “People like you ought to be held to a higher standard because you know better,” he said.

Making matters worse, Kevin Garnett was sitting in that courtroom during Charles’s sentencing, across from Tim, with Charles’s family. At the time, Kevin didn’t think he was a victim. Tim’s attorney later said, “We tried to save Kevin. We tried to tell him.” By 2018, Kevin had filed his own lawsuit alleging Charles stole $77 million through a partnership called Hammer Holdings LLC. Combined, Charles allegedly extracted roughly $100 million from these two NBA stars.

When the Gatekeeper Dies

Stan Lee’s story is different but equally troubling. Despite being the face of characters worth billions, including Spider-Man, X-Men, Iron Man, and The Hulk, he didn’t own them. Early comic deals weren’t creator-friendly. But convention appearances, licensing deals, and media projects still generated significant income, and Stan needed help managing it.

For decades, that manager was his wife, Joan. She handled schedules, controlled access, and served as the gatekeeper. When she died in 2017 after nearly 70 years of marriage, that protective layer vanished overnight. What followed was three overlapping fraud cases totaling over $26 million in alleged losses.

Gerardo “Jerry” Olivares, a former florist turned publicist, had worked his way into Stan’s life starting in 2010. After Joan’s death, he allegedly moved fast, convincing the grieving Stan to sign over power of attorney within days, then firing Stan’s banker of 26 years and his longtime attorneys. A lawsuit alleged Jerry transferred $4.6 million from Stan’s account without authorization, including $1.4 million traced directly to Jerry and $850,000 for a West Hollywood condo.

Then there’s the detail that sounds like something out of a horror movie. Jerry allegedly had a nurse extract vials of Stan Lee’s blood to stamp on Black Panther comics that sold for up to $500 each. Stan never authorized it. The lawsuit called it a “diabolical and ghoulish scheme.”

Max Anderson, Stan’s road manager since 2006, allegedly stole over $21 million, including $11 million in autograph revenue and $10 million in appearance fees. At one 2017 New York Comic Con, Max allegedly collected over $800,000, paid himself $700,000 as a “management fee,” and gave Stan just $50,000. He also allegedly got Stan, whose vision had deteriorated so badly he couldn’t read what he was signing, to grant him a worldwide license to Stan’s name and likeness in perpetuity for one dollar.

Keya Morgan, a memorabilia dealer who took control of Stan’s business affairs in early 2018, faced criminal charges, including false imprisonment of an elder and elder abuse. He allegedly moved the 95-year-old Stan from his home late at night and called 911 on social workers who came for welfare checks, trying to convince Stan he was in danger.

Limited Justice for Stan

The outcomes were frustratingly incomplete. Jerry Olivares settled for an undisclosed amount without admitting wrongdoing. Background checks later revealed he had 45 tax liens and 15 court judgments, none of which Stan had verified before handing over his finances.

Max Anderson’s civil case settled a week before trial. He pled guilty to federal tax charges for not reporting $1.25 million in income and got 12 months and a day in federal prison.

Keya Morgan’s criminal trial ended in a mistrial with the jury deadlocked 11 to 1 in favor of acquittal. The judge dismissed all remaining charges “in the interests of justice.”

The total alleged harm was over $26 million. But total proven misconduct was just Anderson’s $1.25 million in unreported income. That’s it.

Stan Lee died in 2018 before most of these disputes were resolved.

What We Can Learn

As Caleb frames it, “Nobody manages this level of complexity completely alone.” Tim wasn’t reckless. Stan wasn’t naive. They worked with people they had good reasons to trust. “That is normal. But trust without oversight is basically the equivalent of keeping your fingers crossed.”

The lessons for accounting professionals are:

  • Trust needs verification. Independent review and periodic check-ins aren’t signs of distrust. They’re good governance. Charles operated unchecked for 20 years. That’s a single point of failure.
  • Scale changes everything. Once you reach a certain income level, you’re basically a small business. Multiple revenue streams, complex taxes, and licensing deals demand real internal controls and separation of duties.
  • Fraud comes from inside. It’s not hackers or strangers. It’s people who know “where the documentation is thin or non-existent, where no one’s double checking anything.”
  • Life transitions create vulnerability. Joan Lee’s death removed Stan’s only real oversight. Tim’s fraud was discovered during his divorce. Powers of attorney and defined processes are easier to establish in advance than during a crisis.
  • Documentation matters. Charles faxed Tim the signature pages during the NBA Finals rather than the full agreement. Insist on complete documentation every time.

As Tim said after everything came to light, “I was coached early on in my career about preparing for something like this. I thought I was prepared the right way. I thought I did the right things and it still happened. So obviously it can happen to anyone.”

The full Oh My Fraud episode digs deeper into both cases, including more courtroom details and that wild story about Stan Lee’s blood. These stories are reminders that the principles of internal controls exist for exactly these situations. Every client who says “I trust my advisor completely” might be describing a perfectly healthy relationship. Or they might be involved in exactly the kind of setup that enabled Charles Banks IV to steal for two decades without detection.

Tax Season Is the Best Time to Build Your Referral Pipeline

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Rachel Dillon’s January looked nothing like it used to. On the latest episode of Who’s Really the Boss?, recorded at the start of February, she and her husband, Marcus, reflected on surviving the chaos of 1099 season, year-end financials, and the opening weeks of tax prep. But for Rachel, this January brought something different. Her calendar was booked solid with prospect meetings from the moment the holidays ended through the last day of the month.

“This year was a little bit different,” Rachel shares. “My calendar from as soon as we came back from the holidays all the way through the last day of January was booked pretty solid with meetings with prospective clients.”

This wasn’t always the case. In fact, just a few years ago, the Dillons learned a painful lesson about relying too heavily on digital marketing when a website rebrand wiped out their entire online presence overnight.

When a Rebrand Breaks Everything

Back in August 2022, Marcus and Rachel made what seemed like a smart strategic move. They renamed their firm from Dillon CPAs to Dillon Business Advisors. The old name was attracting the wrong leads, mostly people looking for quick tax returns with no interest in advisory services.

“We got a lot of leads and phone calls, but they were all tax-related,” Marcus explains. “We just would filter through those, try to upsell people into CAS services when at all possible. But it was just a lot of no.”

Along with the new name came a new logo and a brand-new website at dillonadvisors.com. There was just one problem. Nobody properly redirected the old domain to the new one. Overnight, every bit of search engine authority they’d built since 2011 vanished.

“We went from three to four online form fills and probably four to five or phone calls per week with new prospects reaching out about services to zero, none,” Rachel recalls. “No phone calls, and no form fills.”

The silence was so complete that they weren’t even getting spam. If your contact form isn’t attracting junk submissions, Rachel notes, “that’s 100% sure, you know your website is not working.”

They waited three months before questioning it, trusting their consulting team’s assurance that new sites take time to gain traction. When they finally investigated, they audited the site with three or four different vendors. The one that ultimately helped them rebuild provided data no one else had surfaced.

The experience taught them valuable lessons. Always redirect your old domain—it’s non-negotiable. Get multiple website audits, and don’t accept vague promises about improvements. And if your leads drop to zero overnight, don’t wait to investigate.

Where Quality Referrals Really Come From

That website disaster forced Marcus and Rachel to rebuild their lead generation around something more reliable than search rankings: human relationships. And it worked. Those January meetings didn’t materialize out of nowhere. They were the result of relationships nurtured throughout the previous year, especially in Q3 and Q4.

When Rachel analyzes where their best leads come from, the same sources keep appearing: current clients who love their team. Professional referral partners like financial advisors, attorneys, and bankers. Personal network connections from church, the neighborhood, and mastermind groups.

“Most likely to sign and quickest to sign are people referred by others who know us,” Rachel says. Whether it’s a long-term client, a team member, or a financial advisor who shares mutual clients with DBA, trust transfers through that existing relationship.

Marcus developed a specific approach to cultivating these relationships. He tells referral partners exactly what capacity the firm has available. “I’ve got room for one more CFO-level client” or “I’m building the roster for this team member you may have met.”

“Having those conversations with people, whether it’s through email or just one on one over the phone or at lunch or coffee, that’s always very helpful because then they have a connection and want to help you,” Marcus explains.

He also ends every coffee or lunch meeting with the same question: “Is there anybody that you think I should meet?”

The Secret to More Referrals: Total Transparency

Rachel discovered that telling referral partners exactly what will happen when they send someone your way makes the biggest difference in referral quality and volume.

“Referral partners want to know exactly what’s going to happen when they refer the person to your firm.  Who are they going to talk to? What timeline should I expect?” Rachel explains.

DBA has answered these questions so thoroughly that they created videos on their website walking through the process. Rachel can articulate the specific workflow. After an introduction, the prospect books a meeting with her through an automated calendar link. From that meeting, DBA requests access to QuickBooks Online and prior-year tax returns. Within five business days, the prospect receives pricing and recommendations.

Knowing their contact will have meaningful answers within one to two weeks makes referral partners far more confident about making introductions.

The firm also nurtures prospects between initial contact and the first meeting. Their website runs on HubSpot, which tracks what pages prospects visit and for how long. If there’s more than a week before the scheduled call, Rachel sends strategic content. That might be a blog article, the pricing page, or an explanation of their “Team of Three” service model.

“If they ask for payroll only, I want them to see those plans and pricing ahead of our conversation,” Rachel says. “Maybe they cancel because they don’t want all of that, or that pricing doesn’t align with what they think. That’s okay. That just means we haven’t wasted anyone’s time.”

How to Start Building Your Pipeline During Tax Season

Tax season might seem like the worst time to focus on business development. Marcus and Rachel disagree. They’ve identified several high-impact, low-effort strategies you can implement right now.

First, capture testimonials when gratitude is fresh. As returns go out and clients express appreciation, reply immediately. Either direct them to leave a Google review or ask permission to use their words as a testimonial. Marcus suggests creating a saved email signature with a direct link to your Google review page (the one that immediately pops up the rating box).

Second, document client wins before they disappear. Rachel recommends keeping a running list of specific outcomes, such as tax savings amounts, successful refinances, or time saved. “We forget those so quickly and easily, especially with the volume of work going in and out,” she notes. Set a goal for eight documented examples during the season.

Third, show up in person. Rachel recently spoke with three marketing professionals outside DBA, all of whom confirmed that in-person events outperform digital outreach for lead generation.

“Even though it feels like you should be doing something online that can cast out to hundreds or thousands of people, that doesn’t give the return that in-person events do,” Rachel explains.

The options go beyond formal networking events. Try study groups, chamber meetings, hobby gatherings, and church groups. Basically, anywhere your ideal clients naturally spend time. Marcus takes it further by inviting clients to events hosted by referral partners. The client gets continuing education credit, and Marcus stands in a room full of other ideal prospects.

If you think you don’t have time for this, Marcus has a pointed question. “Do you even have the capacity to serve new clients well?”

Start Where You Are

Building a referral pipeline doesn’t require a complete overhaul of your practice. It starts with small, deliberate actions that compound over time.

Rachel’s challenge is simple but powerful. “Start thinking about where your ideal clients hang out and how to get in those places. And if it’s not somewhere you necessarily want to be, then maybe reconsider your ideal client.”

Thriving firms don’t wait for leads to find them through Google searches or hope for referrals to materialize. They build relationships, educate partners, nurture prospects, and show up where their ideal clients already gather, even during the busiest seasons.

For Marcus and Rachel, that website disaster turned out to be a hidden blessing. It forced them to build something no algorithm change can destroy: a referral system built on trust, transparency, and genuine human connection.

Ready to hear the full conversation, including Marcus’s exact language for asking for introductions and Rachel’s specific HubSpot automations? Listen to the complete episode of Who’s Really the Boss?.

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.