Betting money is a useful way to
- ensure you have some skin in the game when making assertions;
- get a painful reminder of when you're wrong, so that you'll update;
- make money off of people, if you're right.
However, I recently made a bet with both a monetary component and the stipulation that the loser write at least 500 words to a group chat about why they were wrong. I like this idea because:
- It enforces that some cognitive labor be devoted to the update, rather than relying on the pain of lost cash. Even if you do think it through privately, the work of writing it up will help you remember the mistake next time. (If you don't want to spend that amount of time thinking about why you were wrong, then perhaps you aren't very interested in really updating on this bet.)
- People usually make small-cash bets anyway, so there's not that much skin in the game. Being forced to write publically, or to a select group of peers such as a slack/discord server, makes it feel real for me in a way that losing a small sum of money doesn't.
- Where normal bets may benefit the participants, these kinds of public bets have more benefit for the whole audience. Observers get a lot more information about the structure of the disagreement, and the update which the loser takes from it.
- Often, by the time a bet is decided, a lot of other relevant information has come in as well. A public post-mortem gives the loser a chance to convey this information.
- This kind of bet will often be positive-sum in reputational terms: the winner gets a public endorsement from the loser, but the loser may gain respect from the audience for their gracious defeat and judicious update.
Furthermore, if the loser's write-up is anything short of honest praise for the winner's views, the write-up may provide hints at a continuing disagreement between the loser and winner which can lead to another bet.
This idea feels similar to Ben's Share Models, Not Beliefs. Bets focus only on disagreement with probabilities, not the underlying reasons for those disagreements. Declaring a winner/loser conveys binary information about who was more correct, but this is very little information. Post-mortems give a place for the models to be brought to light.
A group of people who engaged in betting-with-post-mortems together would generally be getting a lot more feedback on practical reasoning and where it can go wrong.