.jpg)
This story was featured in The Must Read, a newsletter in which our editors recommend one can’t-miss story every weekday. Sign up here to get it in your inbox.
It’s a Saturday in a well-appointed room in a luxury hotel in a major American city and a man named Richard Overum has just escorted me from the lobby to brief me on my new identity. My directive: Embody a high roller. A man capable of signing a check for millions of dollars at a moment’s notice. And, most important, a man looking to make an investment. I need to look perfect, Overum explains. Because tonight, I’ll be shadowing him on a sting.
Richard Overum is not a member of law enforcement or a government official. He’s something else: a rarefied practitioner in a line of work he’s all but created for himself. He hunts businesspeople he suspects are breaking the law—a job that by virtue of oft-overlooked sections of federal law can end up paying remarkably well. Tucked into the Dodd-Frank Act, which Congress passed in the wake of the Bernie Madoff scandal and the economic calamity of the late aughts, are provisions meant to encourage people who spot signs of potential financial wrongdoing to come to the government with information. The incentive? If the agencies take enforcement action based on a tip resulting in sanctions in excess of $1 million, the law says, one or more whistleblowers can earn an award equal to 10 to 30 percent of what’s collected.
Whistleblower programs were established at the Securities and Exchange Commission (SEC) and the Commodity Futures Trading Commission (CFTC) to manage and investigate tips, and the calculus for awards depends on multiple factors, including the value of the information in making the case. But the payouts can be enormous. Recent cases have rewarded SEC whistleblowers with $29 million, $38 million, and $104 million. Last year, the SEC cut its biggest check yet, issuing a payout of $279 million to one tipster who reportedly aided in a bribery case involving the Swedish telecom Ericsson that resulted in a more-than-billion-dollar settlement.
Between the start of the program in 2011 and the end of fiscal year 2023, the SEC has levied more than $6 billion in sanctions, and paid out close to $2 billion to whistleblowers. Overum’s share? Tens of millions, he says, between funds collected and those still pending.
The evidence he passes to whistleblower programs he gathers primarily by going undercover—persuading a would-be fraudster to reveal signs of a scheme by posing as a potential investor interested in getting in on the action. That’s why Overum and I have met in this hotel tonight: so I can join him for a meeting with someone he’s investigating.
For some time now, Overum has been compiling intel on Mike King, a real estate developer whose seemingly ostentatious lifestyle and possibly deceptive business practices have raised Overum’s suspicions. And so, under an assumed name, Overum has approached King about making an investment with him—a covert attempt at soliciting more information about his assets, and maybe uncovering signs of a potential fraud. They’ve been texting and chatting about the possibility of getting into business together, and tonight have decided to continue discussions in person. Overum has permitted me to watch him work, but there’s a catch: In order to not blow his cover, I’ll need to be undercover too. I have to play one of his business partners—another potential investor.
Of course, knowing my part isn’t enough. I have to look it: For Overum, sartorial embellishment is another part of the tradecraft. In the days prior, I’d cobbled together my nicest pair of jeans, a tailored button--down shirt that was gifted to me 10 years ago, and I’d even gotten my shoes shined at the airport on the way in. But I needed something more.
“Have a seat,” Overum tells me as he unzips a black backpack and produces two high-end watches. “This is an Omega Speedmaster Dark Side of the Moon, and this one is a Zenith Defy Classic,” he says. “See which one fits.”
I slip one on. “It looks great,” Overum says. “You’ll do great.”
“Are you nervous?” he asks.
“Yes,” I admit.
But as I look at Overum, he seems self--possessed—poised, almost. It’s as if all this—meeting King under a fake identity, preparing to expound at-length upon a business opportunity he has no real intention in investing in—is just another day at the office. And that’s probably because it is.
“Okay,” he says as we prepare to leave the hotel room. “Time to go to work.”
I haven’t told you what Overum looks like. Or where he lives. I’m not going to tell you what kind of car he drives or what teams he roots for. That’s because I’ve agreed to withhold key identifying details. “I want to keep doing this for as long as I can, so it’s very important that certain things about me remain a secret,” he tells me. “If you try looking me up on the internet right now, you won’t find a thing.”
What I can tell you about Richard Overum is that his name is not Richard Overum—that’s the kind of alias he might use in the field. “Richard Overum is a play on ‘dick over them,’ ” he tells me. While we were together, Overum used another alias, a moniker that I can’t reveal because he’s currently using it in yet another case. But I can tell you that it’s also phallic.
“So are your aliases all dick jokes?” I ask him.
He chuckles. “That’s right.” (Though not a dick joke, “Mike King” is also a pseudonym.)
Overum’s sense of humor—often childish—helps him add levity to his day-to-day, which is otherwise earnest and sometimes dangerous. He’s been working as a professional whistleblower for over a decade now, zigzagging the country to cozy up to suspects that he charms and cajoles with cunning, lies, and manipulation in order to coax from them the blueprints for any number of white--collar scams, from Ponzi schemes to prime bank frauds. As a motivator, the cash that he might collect is never far from Overum’s mind.
Back when it was instituted, in the post-Madoff era, the whistleblower programs were meant to bolster enforcement at underresourced government agencies. Authorities at the SEC and CFTC would now have help in the form of newly incentivized citizens. And in the most general sense, the program has worked as intended: In fiscal year 2023, the SEC received over 18,000 tips, and awarded nearly $600 million to 68 individual whistleblowers.
The vast majority of people providing tips to whistleblower programs do so only once in their life. They are not—as Overum is—repeat customers. Over the course of his career, Overum says that his tips, which can include hundreds of pages of evidence, have led to various regulatory agencies, including the SEC, taking action approximately 90 times. (An SEC spokesperson declined to comment on Overum’s claim, citing agency policy to not remark on “the existence or nonexistence of a possible whistleblower submission.”)
You may be wondering why someone who has such a great thing going would risk blowing it all up to talk to a journalist for a magazine story. That is, why go to such lengths—with the aliases and fancy clothes and watches, the anonymity, all the efforts to obscure his identity in my reporting—only to talk so openly about his process? Well, Overum says, he suspects his identity could be exposed one day, and it might only be a matter of time. There might only be so many whistles to blow before Richard Overum could be forced into the light. Giving up on this line of work is a nonstarter, so he’s got other plans in that event—training up a whole new corps of whistleblowers to follow in his footsteps, to start. So talking to me is a call to arms. Everyone, he says, should know about this program. And everyone should know where to find him.
At this point, leads reach Overum in a variety of ways. He has worked with a number of lawyers who specialize in representing whistle-blowers and who often point Overum in the direction of a potential target. “Sometimes it’s employees of companies who see a problem but aren’t comfortable being a whistleblower,” he says. “Sometimes it’s from somebody who just has a bad feeling about somebody and what they’re doing.”
Overum has also created an email tip line that he operates ([email protected]), spreading it through his network of lawyers and confidants. Lately, he’s been looking for potential targets on social media. If he sees people posing on Instagram with yachts, say, or cars that cost hundreds of thousands of dollars, while also trying to raise money, he says, bells immediately go off. “They just seem too good to be true,” says Overum. He notes that he peruses so many accounts focused on ostentatious living that his algorithm is now flooded with images of absolutely over-the-top lifestyles—themselves worthy of further investigation. “I’ve found so many leads this way.”
Lawmakers might have been hoping to incentivize employees who stumble across signs of fraud to speak up, but they’ve also birthed a burgeoning cottage industry—professionals whose careers are built around whistleblower payouts. Supporting tipsters like Overum are private attorneys who specialize in presenting whistleblower evidence to the agencies, and making the case that they should investigate. In some instances, there are even firms who finance whistleblowers, taking a portion of awards when they’re earned. And so the nascent industrialization of whistleblowing has begun to draw criticism from some observers who wonder whether the system’s intentions have been warped—if funds originally meant to support an army of citizen whistleblowers are increasingly funneling into the pockets of a small cadre of experts.
But as long as he’s able, Overum will keep blowing the whistle, sometimes pursuing as many as a dozen cases at once. By this point, he’s got a process: Overum pores over financial and legal information; he hunts for aliases and bankruptcies and business setbacks. When investigations advance to a stage where he needs to interact with a target, Overum will often pose as a would-be investor. Selecting the right assumed identity for any given subject also takes work. Overum spends hours analyzing the subject, trawling through their social media or listening to any podcasts they might have done. “I need to build a psychological profile,” he says. “I need to find out what’s going to motivate them.”
Regardless of the choice, the character needs to feel lived-in, and Overum has to be prepared to speak with a high degree of expertise in any number of fields. “A lot of what I do is Method acting,” says Overum. “I have to understand what my profession is in order to be able to go 20 minutes deep on whatever it is I say I’m doing. And I need to study that role so that I can play that character.”
Outreach typically begins with a call: Overum is trying to pull information that might be incriminating and also build rapport. Flattery and empathy take you far, Overum notes. And one big thing he’s learned over the years is to act somewhat naive. “Not being able to understand what they’re saying has allowed me to rephrase questions over and over until I get the answer from them that I’m looking for,” he says. “The incriminating answer.”
In between calls, there are always text messages. It’s rare, Overum says, that you’ll go long without hearing from a target that turns out to be running a scam. “They always need money,” he says. “They’re always running short on cash.”
Damning information, Overum says, is surprisingly easy to tease out of a conversation. Nobody expects to meet with a would-be whistleblower. “Their guard is down because they think I’m an investor. I’m like an undercover cop in a world where undercover cops don’t exist.”
Over the years, he’s honed a very particular skill set that has brought him into the confidences of a litany of potential lawbreakers—brazen businesspeople who often think, at first, that they are getting one over on Richard Overum.
Generally, it’s the other way around. But slipups do happen. And even one misstep can threaten a case. A few years back, while driving his car, Overum was on the phone speaking with a subject. The man asked who had referred Overum to him; Overum dropped a name. The man on the phone responded: “That’s funny. I just hired that person. He’s never heard of you before.” Overum finished up the call and pulled over to the side of the road. He was so angry at himself that he got out of the car and smashed the burner phone he’d been using to pieces with his foot. He learned from that experience: Don’t ever say something to a possible scammer unless you’re absolutely sure that it won’t come back to bite you.
The job takes on a whole different level of danger during in-person meetings, Overum says, which are nonetheless necessary in order to “further put people at ease” and coax the most damning information out of them. In these cases, he needs to look the part, so his closet is full of custom-made suits and designer shoes. His own natural interest in watches comes in handy on a job.
So too does a certain amount of courage. Several times, Overum says, he has met with targets who were armed. Once he headed down South to meet with somebody he suspected of running a scam. The man was ex-military and arrived at their meeting at a restaurant with a pistol holstered on his waist. While they ate and spoke about an investment opportunity, the man sprinkled anecdotes of wartime exploits into the conversation in a way that unnerved Overum. He found the experience unsettling, but, over the years, he’s learned to maintain his composure. “When I was first going undercover, I would get back to my car and throw up.” These days, he relaxes by listening to metal bands (Tool and Nine Inch Nails are favorites) and playing video games like The Last of Us.
“And before I’m about to meet with a potential scammer, I’ll meditate for 30 minutes or I’ll jump on Zoom with my therapist,” he tells me. “After that, I’m in kill mode.”
Overum had first been tipped off on King, the real estate developer, by one of his attorneys. And because his initial research showed signs of lavish living, like opulent houses and high-end cars—perhaps a red flag, but nothing illegal—he would have to get closer.
Overum decided to approach King as a potential investor, posing as a well-heeled businessman looking to park some money. He called King to introduce his character and let him know he was interested in meeting. Not long after that, Overum visited King’s office, noticing more than one luxury automobile on the premises.
In that first meeting, King would regale Overum with stories of his experience as a developer and describe a number of different investment opportunities that, Overum thought, seemed too good to be true. Time and time again, he seemed to be telling Overum that, if these projects went as planned, he could expect a handsome return on his investment, all with apparently little associated risk.
One opportunity stuck out to Overum: land that King was preparing to develop. For the project, he had told Overum, he would need to raise millions of dollars in just a short period of time. The amount of money and the urgency of the timeline seemed odd to Overum. “Somebody with that much experience, somebody who has done all the things he’s claimed to do, shouldn’t need an investor to ensure a project goes off,” Overum told me. Something strange was going on here, Overum was pretty sure.
It would be important for Overum to continue growing the relationship, determining what additional information he could draw out by posing as a potential investor. King proposed they meet again, this time at a luxury hotel, for some fun followed by business.
When Overum agreed to let me shadow him that night, I watched him deftly channel his character, staying vigilant for all manner of speed bumps that might have spoiled the plot. The emergence of high-definition cameras on cell phones, for instance, is a major peril to undercover work. I took note of Overum ducking away at several points to avoid winding up in the background of someone’s photo.
To do this work well requires internalizing this paranoid hypervigilance, while still exhibiting a graceful self-confidence. Managing these contradictions, I quickly learned, isn’t easy. When, that night at the hotel, someone asked how Overum and I knew each other—a question I’d even been preparing to answer—I froze. Was I going to blow Overum’s cover on a simple introduction? Expertly and casually, Overum jumped in and described us as old friends, pivoting the conversation to safe territory.
Watching Overum in the white--marble-floored hotel foyer was to see someone uncommonly poised, and clearly in his element. Over the background din, I heard him speak about his supposed line of business with a level of expertise normally reserved for real industry veterans. At once, he was fully in character—but also, seemingly, fully himself.
Later that night, after leaving King behind, I asked Overum if anything King had told him might be incriminating. Overum told me that his claims will prove interesting only after he keeps digging and determines whether they’re real or not. “If he was lying to us about anything, then yes,” said Overum. “You can’t misrepresent your wealth or assets to potential investors. That’s fraud.”
It was more than just that financially tantalizing quirk of the federal whistleblower law that drew Overum toward this line of work. His own family had been rocked by fraud, he says. While Overum was still quite young, he explains, his father made a devastating investment. The details were always fuzzy, but the event cast a long and profound shadow. “It was a scam,” Overum says, succinctly. “My father lost everything.” He suffered too: His family moved around a lot in the wake of the incident, and Overum says he turned to alcohol and drugs as a teenager.
In his 20s, Overum began working in sales. “I learned how to read and react to people’s body language,” he says. “I learned people’s tells and how to capitalize on them.”
During this time, Overum would obsess over the impression he could make on people, even practicing his smile in front of a mirror. Like an athlete, he studied filmed interactions of himself making sales pitches, and hunted for ways to improve his performance. In some ways he never really left sales. “I’m selling this fictionalized version of myself,” he says of his work now, “and it all hinges on the story.”
Overum’s journey to becoming a professional whistleblower began in 2011, when someone he was close to told him about a problem at work. He had been hired as a contract worker but felt that he was required to perform tasks reserved for full-time employees. This offended Overum’s sense of right and wrong, and he began to strategize how he might lodge a complaint with a regulatory agency.
He says he presented a state agency with a plan to investigate: He’d pose as a job applicant. If he was offered a part-time gig with full-time requirements, he figured he’d have the evidence to support his associate’s claim. Sure enough, says Overum, the ruse led to an offer of contract work—one that he says contained stipulations around work hours, wardrobe, and travel that could legally be required only of full-time employees.
Overum says the staff at the agency told him they were impressed with his work. So much so that one employee made an interesting suggestion: Why not file his complaint with the federal government? “Do you know about this new whistleblower program?” he says that they asked. “You could make some money off this.”
He wasn’t aware of the program, but he was intrigued. He filed the case, he says, with the IRS, which also maintains its own whistleblower program. It occurred to him that “whistle-blower” didn’t have to be a one-off role—that it could be something more like a job. A calling, even. “I thought, What if I quit my job and just start filing reports on these companies?” he says. The numbers seemed to make almost too much sense. “In one of these cases, I figured the government could haul $80 million,” he says. “That means I could make more than $10 million on the reward. When I realized I could do this for a living—that I could go after the same kind of crooks that fucked up my childhood—and get paid for it? How could I say no to that?”
Overum says he used the same tactics he’d first employed—posing as somebody looking for a job—to secure evidence against about 30 more companies. But he started to recognize some of the inherent challenges in this covert line of work. First of all, he was constantly busy, often researching case law. “I’m not a lawyer, but I was spending months building out cases to support these tips,” he says. “That wore on me.” Plus, there was a cash flow problem. After around three years, his cases were still inching through the regulatory agencies. By that point, he says, he’d been paid only one award. “It could take seven to 10 years, in some cases, to get a payout,” he says. “That wasn’t sustainable.”
He stepped away, finding a job in finance—but he always found himself analyzing deals he was working on for potential fraud. “I was missing the thrill of the chase,” Overum says. “I really realized that I was an investigator at heart.” A few years passed, and one day Overum says he got a call from Washington, DC. An employee at the Federal Trade Commission, he says, wanted to discuss the ins and outs of a particular fraud scheme that Overum knew well. The conversation reignited his interest in hunting these cases. But to make it work, Overum would need to rely on a different system—and some partners.
Overum discovered the lawyer Mark Pugsley, an expert in securities law who had recently represented a whistleblower who would help to unravel a $500 million–plus tax-credit-fraud scheme. Pugsley had worked with dozens of whistleblowers, in the process becoming a magnet for leads on prospective cases. He was instantly impressed with Overum, he told me. “He has a very strong sense of what’s right and what’s wrong,” says Pugsley. “But I also saw that he’s a guy who has big balls. Somebody who could go into situations that could be potentially difficult and, because he’s a good talker, he can talk people into giving him information. He also worked in finance, so he sort of knew the language of investing.”
Since Overum connected with Pugsley, the lawyer’s firm has fed him dozens of tips and helped him with various operations, including with his part in one particularly cinematic investigation. Overum enticed marketers of what the government has alleged was a nearly $500 million Ponzi scheme to board a rented private jet loaded with surveillance equipment so that he could record their conversation and later submit it to authorities—a case that eventually made headlines when FBI agents fired shots during a raid two years ago.
To address some of his other concerns, Overum enlisted the help of a New York–based firm that specializes in financing litigation. The company could provide Overum with money up front, and, when Overum won a whistleblower award, he’d pay them back a negotiated fee. This would allow Overum to cover surveillance equipment, burner phones, and other expenses, and, most important, not have to worry about when money was coming in.
One of the firm’s managing directors told me that his organization was thrilled by the chance to get into business with Overum. “Because he had a track record of success with these cases, we believed in him and saw him as a good investment,” he says. “I was happy to give him as much money as he needed, because we’re confident we’ll see a healthy return.”
In the year since I’d met Overum, in April 2023, his work, he tells me, had resulted in various raids, arrests, asset freezes, temporary restraining orders, receiverships, and whistle-blower awards. “It goes without saying that I’ve been busy,” Overum says.
By June of this year, he felt his report on Mike King was ready to be filed. Of course, he hadn’t made any investment with the developer—Overum had been stringing him along with a variety of delay tactics. Each time the rubber met the road to cough up some cash, Overum had a new ready-made excuse as to why that wasn’t the right time for him to jump in.
All the while, Overum was doing whatever he could to extract information. Overum says that King sent him documents that Overum believes, based on his own research, misrepresented the value of King’s assets. Overum—playing the part of a prospective investor—says that King was painting for him a deceptive financial picture of his business, as well as his track record and certifications. As their conversations had worn on, King proposed various investment opportunities to Overum—each with provisions that Overum found head-scratching.
“The numbers he was throwing out made no sense,” says Overum. “This follows [his] pattern of making grand promises that seem to fall apart once documents are provided.” Overum was convinced that he and Pugsley could make a case to the government that the developer was operating outside of the law. As of this summer, they were strategizing about the most advantageous way to file the report and how to most effectively present the evidence Overum had gathered—that is, trying to figure out how to get their hoped-for reward (to say nothing of justice) as quickly as possible.
His work on this case might not necessarily satisfy critics who worry about an industry developing around whistleblower payouts. But Overum remains focused on the bottom line. “The simple fact is that whistleblower programs work,” he says. “If whistleblowers are financially motivated, they’re going to do a better job making sure their information is correct so that they can win an award one day.”
Overum figures he’ll eventually stop receiving government payouts—but not because the government will eliminate whistleblower programs. It’s because he suspects that his identity might eventually be revealed. It’s an outcome he dreads. But he’s already developing a contingency plan that won’t require him to work in quite the same way. Instead of taking on the cases all by himself, he’s imagining a sort of school to further expand the number of trained whistle-blowers, a venture that will also require more lawyers expert in securities law. “I want to teach an army of people how to do this and send them off on stings,” he says.
But Overum is also operating with another sort of ticking clock in mind: The sooner he can find and expose a fraud, he can prevent more and more people from being preyed upon. And those who’ve already fallen victim can get an earlier start on the road to being made whole.
“In every single fraud we’ve exposed, the victims would never have seen a dime back if not for our efforts,” Overum points out. Altruism, in this world, doesn’t always come for free. “Obviously,” he says, “none of us would be in this if there wasn’t a financial incentive.”
Gordy Megroz is a journalist based in Colorado.
A version of this story originally appeared in the September 2024 issue of GQ with the title “How to Make a Fortune as a Professional Whistleblower”
