ChatGPT now comes up in most of the extended conversations I have with lawyers about how things are going. Many rave about how easy it is to have this robot whip up a simple motion or even, in one example, “a short speech about NATO defense capabilities.”

While it may be true that ChatGPT can do what an executive assistant or an inexperienced associate might be able to come up with, even its biggest proponents agree that you can’t just take what it gives you and put that out there as your product.

But what about for an investigator? Is ChatGPT helpful?

I wrote about this last month on our other blog, The Divorce Asset Hunter. In that article, Would an Artificial Intelligence Asset Search Help? I argued that ChatGPT’s own disclaimers made me skeptical about its usefulness, since it depends on lots of data and has what its creators call a “limited understanding” of the world. It’s all there at

Leaving aside that computers don’t “understand” anything, but rather imitate prior examples of understanding, I think the bigger problem is the first one. You can get a pretty good short speech on NATO out of it because there are thousands of such speeches floating around on the internet.

After I wrote that blog last month, I eventually tried ChatGPT to see for myself how restrictive those potential limitations might be. My answer is, pretty darned restrictive.

A client asked this week to find out why an associate could have been visited by the FBI at his home, or whether perhaps these were process servers pretending to be FBI, since they had not been too keen to show ID up close as the Bureau requires.

I asked the chat bot, “Why would law enforcement be looking for Albert R. Jackson?” (not his real name).

ChatGPT’s answer was that it doesn’t deal with specific people or situations. That was the same answer I got when I asked whether nepotism was a problem at a particular public company (where people on chat boards had been complaining about just such an issue).

It’s not that ChatGPT gave me boilerplate on these two question. It gave me nothing.

Do not mistake this for a blanket dismissal of the power and potential of artificial intelligence. As I wrote last month,

The more I have looked at artificial intelligence, the more bullish I have been about the rosy future for investigation. AI and greater computing power will generate volumes of data we can only dream about right now. Automatic transcripts of every YouTube video, for example, would mark an explosive change in the amount of material you would have to work with in researching someone. So would the ability to do media searches in every language, not just the small number offered by LexisNexis. I wrote about this in a law review article a few years ago, Legal Jobs in the Age of Artificial Intelligence.

The future is bright for investigators using AI. More data will mean more things to research and interpret. But who will do the research and interpretation? Smart people will, as they do today.

In a financial investigation it’s easy to get buried under all the words and numbers and to forget about emotions – those of your client, the person you’re investigating, and your own.

It’s understandable but something to guard against.
  1. If your client is particularly stressed on the day of your meeting, not thinking straight, or stubbornly sticking to a theory you can’t substantiate, have a bit of understanding. This can happen more in family law cases than anywhere else, but corporate struggles can get emotional too. Try to stand in your client’s shoes: it may make it easier to get your message across. And people generally prefer to deal with those they think understanding them.
  2. Good investigators sometimes have to weigh different possible theories regarding their subjects. In deciding where to start in filling in missing links in a chain of facts, it can help to try to guess what your subject might have been thinking. Was he motivated by greed? Revenge (stemming from disdain or hatred)? Guilt? Did he have an incentive to lie? What else was happening in his life that would have subjected him to stress?
  3. Our own emotions play a part. Do I have an instantaneous liking or disliking for the subject? Is that well grounded or the subject of prejudice (maybe an association with someone similar?) Too much affection for a theory can lead to ignoring competing theories that might be correct.

The Power of Dance

One reason I love to watch dance is that it provides a huge contrast to my everyday life that is filled with words and numbers. Not only am I reading, I am writing about what I’ve found, attempting to blend the words and numbers I have assembled into a coherent story about a person and that person’s business (and/or personal) activities.

Dance is wordless and numberless. There is music, of course, and that is based on rhythms that can be reduced to numbers, but the numbers are below the surface of the experience. Other than the title of the work, there are rarely any words at all (certainly at the New York City Ballet, which we have attended for years — see photo above).

Watching and listening during dance is a great reminder that emotions need not be affirmed by the written word to be real. But they are still there for us to recognize as we do our work.

Is it in poor taste to argue against leaning too hard on credentials when you post something on LinkedIn, a platform where people showcase their credentials for all to see? I don’t think so.

If you want a lawyer who will do a good job drafting a will, handling your divorce or making sure you’re signing a good employment contract, how important is it that she went to a top-five law school?

You want someone who, on recommendation from someone you trust, will get the job done and won’t be a jerk to deal with. A law school transcript from 25 years ago won’t tell you how that lawyer deals with clients, keeps up with recent changes in the law, reads a family law judge or the opposing lawyer to know how far to push things in a negotiation. Those, and hundreds more qualities, are acquired through experience building on good intuition.

I’m convinced that it’s nearly impossible to teach intuitive thinking. You’ve got it or you haven’t. It’s necessary for a lot of jobs, including being an investigator, but not sufficient. Good investigators know things, so that they can say to themselves, “That doesn’t seem right to me.”

Bernard Madoff with a tiny audit firm in a suburban shopping mall? Doesn’t seem right.

A guy telling his girlfriend about his high-end investment bank that has no website and only a LinkedIn page with a typo on the first line? Smells bad. True story: It was.

A law school professor of mine used to remark that there’s a reason there are no child-prodigy lawyers, and the same would go for top-notch investigators who are still in middle school. The number of permutations on a piano keyboard or a chessboard is miniscule compared to the number of permutations there are in life.

Analyzing those permutations takes practice but also a knowledge base we’re not born with.

Look at the wonderful surreal painting above by Morris Hirschfield (1872-1946). He was until 65 years old a tailor and then a designer of shoes. On retirement he began painting compelling figures like this one (it’s called “Girl in a Mirror,” but this can’t be a mirror).

Hirschfield was ridiculed by many in his day as an untrained bumpkin, but his lifelong experience of dealing with the human figure, his sense of color and balance plus his imagination produced marvelous works now owned by some of the world’s richest museums.

So by all means, look at where someone went to school if you want to. It’s a good conversation starter and you may know people in common. But schooling is a terrible way to decide whether or not they’re any good at what they do.

I’m asked all the time when I meet other professionals, “Who’s a good referral for you?”

I usually answer, “Litigators are good – if you want to see if it’s worth suing, or you want to look into the people on the other side, and we do trademark and copyright work too.

And anyone thinking of making even a modest investment ought to know who it is will be taking their money.”

All the work we do with cases studies is also on our website.

But recently, someone asked me, “Who’s a referral that people would think would be good for you, but really isn’t good?”

My answer was: “People who want me to break the law.” By far the most common request is to get information on how much money someone has in the bank, and where that bank is.

A few years ago, we helped the Atlanta Journal Constitution do a great piece on the illegal trade in bank accounts. The story they wrote is here.

I also wrote about the issue in 2020 in the American Journal of Family Law.

If I Can Check on Your Opponent, I can Check on You Too

Think about it: If you call me and ask me to find out how much money your enemy has in the bank and you think that’s OK, is it OK if I look into your bank account to find out how rich you are? What about finding out how much you paid a competing investigator last year?

Of course, you don’t want me snooping into your private affairs, and that’s why I won’t snoop into your enemy’s either.

What do we mean by private? We mean things that are off-limits by law. The system in the U.S. is designed to make it hard to drill into someone’s bank account without the supervision of a court. That’s a good thing. Just like not being able to bug their home, wiretap their calls, and now, in many states, put a tracker on their car without their knowledge.

Just because the law is breakable doesn’t mean you should break it.

I can look at your enemy’s deeds, mortgages, his divorce settlement (depending on the state), professional licenses, SEC trading disclosures, old news releases still hanging around the internet that he wishes were scrubbed. If he’s Norwegian, I can look at his tax return. If he’s American and has a non-profit, I can look at the non-profit’s tax return.

The list goes on. Privacy means different things in different countries. In this one, it’s amazing what you can find out about people without invading their privacy as defined by the law.


Want to know more about how we work? Our website has a wide range of publications and videos. You can also read my book, The Art of Fact Investigation which is available at bookstores online and for order from independent book sellers. And check out our other blog, The Divorce Asset Hunter.

Investors in Madoff Securities and FTX were both warned, but by different sets of people.

If it turns out to be true that without customer knowledge FTX took billions of dollars of customer account money to invest in a risky company owned by FTX’s CEO, this will truly compare to the Madoff scheme for audacious fraud (though smaller in dollar size).

The major difference is that with Madoff, whistleblowers were trying to alert regulators that his stated returns didn’t make sense, not to mention his use of a tiny accounting firm and having no independent custodian for his funds.

Regulators on Madoff just missed it.

With FTX, regulators were the ones shrieking that this was a dangerous proposition, but many people didn’t listen.

In September, the UK’s financial market regulator warned consumers that FTX was operating without their approval, and that investors “may not be able to get their money back if things go wrong.” This followed previous warnings about other crypto platforms.

Before that, in March of this year, three European Union regulators for securities, banking, and insurance issued a joint statement warning consumers that they faced the very real possibility of losing all their invested money if they buy these assets. Consumers in crypto had no recourse to compensation under existing EU Financial Services law, the statement said.

The same month, Securities and Exchange Commission Chairman Gary Gensler, in a tussle with the U.S. commodities regulator and members of Congress over who gets to regulate crypto, stated: “If the platform goes down, guess what? You just have a counter-party relationship with the platform … Get in line at bankruptcy court.”[1]

Our modest contribution to pointing out the early days of Crypto regulation came in April, with When Too Few Regulatory Problems Add to Risk.


Who Gets Most of Our Sympathy?

Being in the due diligence business, I can be surly when people worth millions of dollars decide to forego a few thousand in due diligence and then complain they made an investment that was riskier than they thought it was. Many of the Madoff victims fell into this category.

The same goes with the richest people investing with FTX, as well as the insiders who willingly took FTX play money (FTT) instead of dollars, and then banked it all at FTX instead of in a “wallet” separated from the company.

I have a lot more sympathy for the small investor our investment laws are meant to protect – the “unaccredited” investor not worth that much money who perhaps can’t afford expensive due diligence and who depends on the government to watch over those taking in investments to make sure the money is properly segregated and invested appropriately based on the stated risk profile.

In this case, though, even the government was pretty clear that this was the Wild West: Crypto was a law unto itself and you risked fighting to get your money back in bankruptcy court.

Nobody can say they were not warned.

[1] A former Harvard Law School Professor co-wrote in yesterday’s Wall Street Journal that Gensler’s agency may be partly responsible for some of the FTX customer losses, because in March it discouraged banks and brokerages from keeping crypto assets in their custodial businesses without adding them to the bank’s balance sheets. That is not the requirement when keeping stocks and bonds in custody.

You want to invest $3 million into a real estate project. Time is tight because it’s closing in 12 days. The developer (51 years old) seems to have a decent track record and takes credit for billions of dollars of projects, but this project doesn’t yet have zoning approval and the previous owner dumped the property because his plans to develop it got tied up in court by angry neighbors.

  • Scenario one: You find the developer has no criminal record and no bad press. Your lawyer looks over the contract and you send the developer your $3 million because the return looks attractive. Four years go by and the project is mired in delays, cost overruns, and your guy gets the project into expensive litigation with another partner (something it turns out has happened in a prior project of his). In the end, as he considers selling the land, you are happy to have him buy you out at a loss.

Cost: $1.25 million. But you saved $3,500 by not paying for good due diligence.

  • Scenario two: You find the developer has a history of litigation against close associates, plus got into a loopy lawsuit over a $5,000 dispute that he says knocked down his credit rating. He has billions in past projects but he’s taking time to litigate over $5K. You see that the project doesn’t have approval and that he’s been unable to refinance his large mortgage even though rates have fallen. Maybe he’s too highly leveraged in his other projects. Maybe he hasn’t done those billions he claims he has. You pass on the project.

Cost: $3,500. And you have $3 million in dry powder to invest somewhere else.

$3,500 buys back your $1.25 million mistake, not to mention any excess returns a different project could earn.

 0.28 percent seems like a fair price to have paid.

Think of due diligence the way you think about car insurance above the minimum amount your state requires. In New York, you could get insured for just $50,000 in case the other person in an accident should die. But what happens if they die and you get sued for $2 million? Inadequate insurance could result in a lien on your house.

You will try your best to drive defensively, but if  you make a mistake you’ve prepurchased the cost of the mistake with a higher premium.

There is no state law anywhere in this country that says you have to spend a minimum amount of money in due diligence on a proposed business transaction. You are fee to lose millions on a bad deal.

But if you are insured for more than the minimum coverage allowed for a car accident, why are you risking big money with your investment by foregoing good due diligence?


Want to know more about how we work? Our website has a wide range of publications and videos. You can also read my book, The Art of Fact Investigation which is available at bookstores online and for order from independent book sellers. And check out our other blog, The Divorce Asset Hunter.

One indispensable part of due diligence is to check for regulatory sanctions. Was a company found by the SEC or FINRA to have misappropriated investor money? Put them in unsuitable investments? Lied on a filing to induce people to invest money under false pretenses?

While we never pronounce “Invest” or “Don’t Invest,” “Hire” or “Don’t Hire,” regulatory sanctions are something our clients can put into their personal mix that determines risk tolerance.

But what about when you don’t find any regulatory problems? That too can flag a problem. And the bigger the prospective deal, the more the complete absence of regulatory problems becomes. Two issues in the news today come to mind on this front: Cryptocurrency and ESG investing.

As we saw with the Bernard Madoff scam (and countless others), it’s what is not in evidence that should cause the greatest concern. In Madoff’s case these can’t-be-founds included an independent custodian, a Big Four auditor, reasonable variability in returns for equities, and in the last couple of years before he was caught, evidence of billions of dollars of equity holdings in his 13F SEC filings.

Bad, cheap, check-the-box due diligence, could and did robotically report to you that “No sanctions were found” for Madoff’s operation. Plenty of people refused to invest with him because of what they expected to see but did not. Still, a lot of the due diligence failed them. Even the SEC was unable to nail Madoff after repeated approaches by a whistleblower.

Unlike with Madoff, I am not suggesting any evidence of criminality with the examples below. It is just that there is a lack of what I would want to see in an investment that was not high risk: That they are governed by rules and that they follow those rules.

  1. Environmental, social and governmental (ESG) investing. What’s remarkable about the categorization for investors of ESG investing is that there is no accepted definition of what ESG is. While regulators can come down hard on companies for violating accounting standards, there are no ESG standards to violate. This was explained beautifully in a Bloomberg article, The ESG Mirage, last year.

If someone is selling you a bond fund, you would expect it to be full of bonds. A gold miner’s ETF should be about investing in gold miners. But investing in companies with good ESG scores is a matter of sorting through more than 160 different, competing standards for what makes a high ESG score – what Bloomberg calls “a foundational yet unregulated piece” of a multi-trillion dollar business.

If you have a business worth tens of trillions of dollars, you would expect some wrongdoing to pop up here and there, but it’s down to Bloomberg and other journalists to tell you that ESG can mean nearly anything Kick out Tesla, upgrade Exxon Mobil. How is an investor to tell the quality of the ESG product he’s considering?

  1. We are now seeing the early stages of litigation meant to determine what kind of regulatory regime will govern cryptocurrency in the U.S. The industry says it’s a commodity and should be governed by the Commodity and Futures Trading Commission (CFTC). But the Securities and Exchange Commission (SEC) is having none of that. Even though Congress hasn’t spoken specifically about which agency ought to regulate crypto, the SEC is proceeding as if there is a clear answer to what cryptocurrency is.

It’s not an absence of regulatory activity, as with ESG, just the very early days of it.

When the rules are unclear, risk goes up. At around $1 trillion, the crypto market (including cryptocurrencies and non-fungible tokens), presents a huge amount of regulatory risk.

None of this means you shouldn’t pay attention to ESG ratings or crypto. But the idea that these are well-settled concepts with anything like low risk is an idea a serious investor should dismiss.


When not at work, I like to do many things, and one of my favorites is to watch New York Mets baseball. Since moving to New York I’ve grown to love the team and I make common cause with the many Mets fans I run into (even in my Bronx neighborhood just a few stops from Yankee Stadium).[1]

Keith Hernandez, 1986: Barry Colla Photography, Public domain, via Wikimedia Commons

One benefit of watching the Mets is that our team has what many consider to be the finest broadcasters calling their games. The radio team led by Howie Rose is unmatched for its knowledge of the game and willingness to criticize the home team if that’s merited. Most of my intake is via the TV broadcasters, often rated the best in the game. Included in most of these games is Mets alumnus Keith Hernandez, who provides an education on hitting each and every time he sits down in the booth. [2]

Some of what I’ve learned watching Mets baseball turns out to be applicable to my work life.

  1. Not everything is under your control. If your umpire that day is a “pitcher’s umpire” (one who calls a generously-large strike zone), then some close pitches are, in the words of Hernandez, “too close to take.” You had better try to hit them or foul them off. Passivity can send you back to the dugout. Hernandez doesn’t criticize umpires for large or small strike zones, and goes out of his way to praise the umpires who keep their zones consistent. If an umpire is calling inside strikes all day long, shame on you for watching as a close one goes by you for strike three.

Our “umpires’ are the circumstances in which we find ourselves. If we are investigating on a tight deadline and need to get records in a county that does not permit on-site searching in the courthouse, we prefer to over-order any record that could be relevant so we can sort them out later. If someone is going to rule out a document as being irrelevant, we want control of that process. If we get too many documents and need to discard some as being of no use, that’s like a two-strike foul. Better that than to fail to order the document that could turn out to be the one we need. That would be looking at strike-three.

On the other hand, if we’re in a county that has a nice full set of records online, we can be much more selective up front because we can read the dockets ourselves and sometimes figure out whether the case relates to “our” John Smith or someone else with the same name.

Overseas, some countries have nice public record systems that permit searching and unambiguous reporting. Other nations have no concept of a public record. All the information you get in these places is unofficial, even if highly informative. It’s no good cursing your bad luck that the investigation takes you to a difficult location. You’re at bat and you make the best of it.

  1. You may need to change your approach a few pitches in. Hernandez talks all the time about “good two-strike hitting,” which means that you may need to change the way you want to swing when there is a much greater price to pay for being unsuccessful on the next pitch. Instead of trying to hit the ball in the most powerful way (“pulling” toward the right for left-handed hitters and vice-versa), many good hitters just “slap” or “poke” the ball through an opening the other way for a single.

In other words, if you’re not going to hit a home run, better to hit a single than to strike out.

We love investigations that turn out to be “home runs” right away. The million-dollar fraud we discovered being perpetrated by our client’s litigation opponents that forced them to drop their suit; the $60 million in traceable assets we found in even less time during a divorce asset search.

But what if you don’t find that kind of thing that quickly? Two strikes for us can mean we are running out of time (before a court-imposed deadline), running out of budget (you can’t afford to look everywhere); or both. We try to concentrate on the jurisdictions most likely to yield records about our person, rather than all thirty counties he may have lived or worked in over the past 20 years. This is what’s called Bayesian analysis – refining search terms based on what you learn as you go along to increase your odds of success.[3]

If we’re trying to impeach the credibility of a witness, we may find no prior conviction for fraud (a home run), but the omission of a job on his resume eight years ago could turn out to be valuable if it leads to evidence that he was fired for incompetence there (long single or double).

  1. Analytics are helpful, but you also have to trust your eye and what the pitcher is doing today. The data may tell you that with two strikes a pitcher is x% likely to throw a breaking ball, but what if the third time through the batting order you notice he has started “tipping” his pitches (involuntarily signaling what he will throw next)? That won’t be in the data, but it will be obvious if you’re watching.

We too have access to lots of data. Databases give us nice head starts on where people have lived, what companies they’ve associated with, some criminal convictions, and names of relatives. But we still subject all of that data to verification by checking it ourselves. It’s often right, but it’s wrong often enough that you can’t just trust it blindly.

One database thinks I still live in the home we sold 12 years ago, based on a grocery store discount card I obtained while living in the old house and which I continue to use today. The grocery store continues to sell my data to aggregators, who continue to report that I live where I don’t. Anyone checking the county record at the old place can see it was sold, but if they don’t check they’ll get it wrong.

Along with his equally brilliant commentators Ron Darling and Gary Cohen, Hernandez is also brimming with tips about fielding, especially regarding the placement of infielders given the situation (the hitter at bat, the score, the count). These tips also pertain to investigation. That article will be appearing before the Mets next win the World Series.[4]

[1] There are many Yankee fans around too, and I also count them among my friends. There is even, for some reason, a lifelong Bronx resident who roots for the Phillies. It only took him two years to admit it.

[2] Hernandez will have his number retired by the Mets on July 9. He has not been elected to the Baseball Hall of Fame, though his career on-base percentage of .384  is close to that of Detroit’s Miguel Cabrera, often referred to as a shoo-in for Cooperstown. His WAR (wins above replacement) of 60.3 is better than those of Yogi Berra, Willie Stargell or Vladimir Guerrero, and just 0.1 below Harmon Killebrew’s. He was also famous for revolutionizing play at first base, where he won eleven consecutive Gold Gloves.

[3] I discuss this further in Legal Jobs and the Age of Artificial Intelligence, Savannah Law Review Vol. 5, No. 1 (2018).

[4] Date to be determined.

Many of us love optical illusions. It’s a safe thrill to know we’re being tricked, and yet are still unable to tell our brains to “get real” and stop the illusion.

Bridget Riley, section of Blaze 4 (1964)

When you’re doing an investigation, the same kind of thing can take over your brain: You want to look at facts in one way, but your brain won’t let you. That can lead you to the wrong conclusions. There’s a great explanation for the evolutionary reasons optical illusions work on us, at the American Museum of Natural History site.

I wrote about illusions in my book, The Art of Fact Investigation, and was recently reminded again of their power when viewing a wonderful retrospective of the paintings of Bridget Riley, at the Yale Center for British Art.

Sometimes in Riley’s work, what you know to be a static picture looks as if it’s moving (scroll quickly as you look at the section of the work above). As the AMNH site explains, we evolved to focus attention on movement because it can be a sign of danger.

“Even when you stare at a still object, your eyes dart around. Normally, your brain can tell the difference between your eyes moving and an object moving. But because of the strong contrasts and shapes in the illusion, your brain gets confused. Your motion sensors switch on, and the image seems to turn.”

Or take a look at the picture to the left. It’s the famous “Duck-Rabbit” with a duck looking left and a rabbit to the right.

Even after we know that we are looking at something unusual, this image is fascinating. While the information on the page never changes, we can see only a duck or a rabbit, but not both at the same time. It’s very hard to take in simultaneously two facts that we know to be mutually exclusive.

Investigation can feel like that too. In forming theories as we investigate, we gather evidence that may end up supporting what appear to be incompatible or contradictory conclusions. Our instinct is to favor the evidence that supports the conclusion we think is more likely, but we must resist that tendency. We will not find a man who is/is not bankrupt at the same time in the same jurisdiction (impossible), but we may find someone who was extremely wealthy in January and is broke in March.

Looking at the duck-rabbit takes more energy than looking at a conventional picture of a duck or a rabbit, because it clashes with our understanding of what kinds of animals exist on earth. A man who goes from riches to rags in six weeks will, similarly, be harder to investigate because we will have to overcome our own skepticism before we can consider the entire picture of events.

The tendency to find evidence to confirm the case we are trying to win is called confirmation bias, and lawyers are bursting with it. Lawyers are competitive by nature. Evidence they need is something they will naturally want to believe they have uncovered.

Consider the scope of the investigation. Since we “know” Robert Jones is strictly a “New York guy,” we will not even look outside New York to see what else he may have done or acquired outside the state. That’s a mistake.

In screening witnesses, we see that an expert witness has testified dozens of times, so we “know” he has no embarrassing personal history that could affect his credibility since “someone” is bound to have found it by now. Wrong again. At least, wrong not to check.

Optical Illusions in Finance

As for a static picture that appears to be moving, think about Bernie Madoff’s scam. Talk about bold colors and contrasts: He was a leading light in finance, apparently very wealthy, and highly exclusive about who would be allowed to invest in his apparently successful funds.

Master Illusionist

The movement in the Madoff picture was something now known as FOMO (fear of missing out). So much was apparently going on in his universe that you were a fool to pass up a chance to give him money.

In the end, it was an illusion. An accountant in a shopping mall, no independent custodian, and SEC filings that showed just a few million (not billions) under management.

Bridget Riley’s illusions are enjoyable, thought provoking and sometimes disturbing, but the fact that they are illusions is not a secret.

They are worth keeping in mind the next time your investigator comes back with a “sure thing.”