“A knowledge of cheating methods and the ability to detect them is your only protection against dishonest players in private games. It is for this reason that the most ethical, fastidiously honest card games are those in which the players are top notch gamblers, gambling operators, gambling-house employees and card sharpers. When they play together the game is nearly always honest. It has to be, because they play in an atmosphere of icy distrust, and their extensive knowledge of the methods of cheating makes using their knowledge much too dangerous. They do not cheat because they dare not.
In a money card game patronized by men and women who know little or nothing about cheating techniques, the odds are 2 to 1 that a card cheater is at work.”
John Scarne, Scarne’s New Complete Guide to Gambling (1986)
I came down with some horrible, vaguely flu-like illness recently. Happily, this at least coincided with the arrival of a print copy of Scarne’s New Complete Guide to Gambling. It’s more of a reference text than something you’d read cover to cover. What impressed me most as I leafed through its 800-plus pages was Scarne’s obsession with cheating. In addition to a full sub-section on methods for cheating at card games, nearly every discussion of a game includes a section on common methods for cheating. Rigged games, it seems, are the default state of the universe.
Scarne’s dismissal of carnival wheels is typical of both his logic and wit:
If you want to play carnival wheels for fun, you would be smart to consider that 25% to 50% of the money you wager on each spin is a donation; when you reach the total amount you wish to donate—quit playing.
As you’d expect, in addition to cheating, Scarne was fairly obsessed with edge. Of poker strategy, he writes:
There is one big secret, a Poker policy which, if put to use, will not only make you a winner at your next session but at most of them. It’s a policy that is practiced religiously by the country’s best poker hustlers. It is the only surefire rule that wins the money. It’s a simple rule: Don’t sit in a Poker game with superior players.
There are plenty of ways to apply this rule to investing. It’s well-worn ground in the context of the active/passive debate. I’ve got little to add there. So let’s talk about another application. Let’s talk about deals. Specifically, let’s talk about the “democratization” of deals—how increasingly, private equity and credit strategies are being pitched to wealthy individuals and their financial advisors as important, if not essential, additions to portfolios.
I’m hardly a low complexity, liquid asset teetotaler when it comes to portfolio construction. I happen to believe private market deals offer a rich opportunity set for value-added portfolio management by skilled professionals.
Why? Because we’re talking about a relatively inefficient, illiquid market where the participants are allowed to act on inside information. A real poker game. A wild west poker game, even. I suspect John Scarne would feel right at home at the helm of a PE or VC shop.
And wouldn’t you know it, the dispersion of returns for non-core real estate, private equity and venture capital managers is immense.

What is the single most important thing that separates a top quartile manager from a bottom quartile manager?
Deal flow.
To continue with our poker game analogy, in the larger cap areas of public markets you can be reasonably certain the cards have been dealt fairly. Deal flow isn’t an issue there. In private markets, it’s just the opposite. Private markets are about card sharping. Pickup stacking. Riffle stacking. False shuffling. Nullifying the cut. Bottom dealing. There’s a reason certain big firms’ shticks are recruiting a vast army of consultants and partners, many of whom who operate at the nexus of government and business. There’s far too much money at stake here to leave these things to chance.
I have a friend who did a tour as a White House Fellow. Believe me when I tell you the deck is stacked. The big PE shops and consultancies are masters of the riffle stack.
So where does that leave us?
We can either learn to see the angles, or we can decline to play. When it comes to deals, there are plenty of hands not worth playing.
To take a simple example, let’s think about interval funds. These are private equity and credit deals packaged in a mutual fund-like wrapper that can more easily be sold to mass affluent clientele. The pitch is that you, or your financial advisor, can access the private equity “asset class” with more favorable liquidity terms, 1099 tax reporting, and so on. “Private markets for the rest of us,” so to speak.
What’s not to like?
I’ve had the opportunity to discuss these with a couple investment banker types. I always ask the same question: “How can we know the sponsors aren’t just dumping all their worst deals into these retail vehicles as an excuse to charge fees on the assets?”
The answer always comes back: “You can’t.”
And as anyone who’s ever invested in anything even remotely illiquid well knows, favorable liquidity terms are just, like, someone’s opinion. Read the docs! If stuff ever hits the fan, you’ll be gated and locked up like everyone else. No one cares about liquidity when times are good. Everyone wants liquidity when times are bad. The more desperately you want out, the more likely you are to find yourself trapped. This is a timeless axiom of risk management.
Oh, and there’s always the matter of performance evaluation. Deals are sold on the basis of IRR, but “you can’t eat IRR” (it doesn’t measure cash-on-cash returns). So remember to compare IRR to MOIC, and on top of that to look at everything in the context of your original capital commitment, ’cause there’s an opportunity cost to committed capital. You can go on and on with this stuff. We haven’t even gotten to trends for deal multiples, or the dispersion of those multiples across across market segments, or the leverage and coverage levels for those deals, or what any of that might mean for prospective returns…
…so, yeah, there are lots of angles in private markets.
How do you learn to spot them?
The same way you learn to gamble. By playing. By getting fleeced. By losing money. Scarne again:
After twelve hours of gambling, Fat the Butch found himself a $49,000 loser, and he quit because he finally realized something must be wrong with his logic. He was, later, part owner of the Casino de Capri in Havana, and when I told him it would need 24.6 rolls to make the double-six bet an even-up proposition, and that he had taken 20.45% the worst of it on every one of those bets, he shrugged his massive shoulders and said, “Scarne, in gambling you got to pay to learn, but $49,000 was a lot of dough to pay just to learn that.”
I’m not saying you shouldn’t play this game.
I’m saying if you choose to play, you better play to win, and you better be ready to take some hard knocks along the way. DO NOT DABBLE NAIVELY. Because the folks pitching you deals, and their competitors, are definitely playing to win. Winning is their business. I’m not talking narrowly about generating attractive net returns for investors. I’m talking about fee revenue and carried interest. Fee revenue and carried interest are the metagame here. And there’s far too much money at stake to leave that outcome to chance. Regardless of your net returns as an investor.
Since this is a Scarne-inspired note, I’ll give him the last word:
When you play cards, give the game all you’ve got, or get out; not only is that the one way on earth to win at cards, it’s the only way you and the rest of the players can get any fun out of what ought to be fun. You can’t play a good hand well if your mind’s on that redhead down the street or the horses or your boss’s ulcers or your wife’s operation. When you don’t remember the last upcard your opponent picked and you throw him the like-ranked card which gives him Gin, it’s time to push back your chair and say, “Boys, I think I have another engagement.”