One modification to the current methods I've thought of is a lottery system. This method would have people purchase a ticket (likely a code) for the opportunity to win a cap. This enables the maker to have a lot more control and input on the market value for their work, and be compensated in kind. In particular, I thought of 4 ways:
1) the maker can set the price of tickets, creating an appropriate barrier to entry. At present, there is no clear deterrent for folks with a pure financial incentive to enter. Entering raffles is a free way to make a buck, because the only barrier to entry (purchasing the cap) is incurred when someone with such intentions is already assured a return on their investment. This also affords them the means to account for the maker's perceived value of an item.
2) the maker can also run promotions/giveaways for entries, meaning they can spread the love without just giving 1 individual with absolute means to pursue a financial incentive.
3) the maker can set the number of tickets available and or timeframe in which they are available, which would provide the sense of urgency and emotional investment that raffles currently enjoy. It's also complementary to setting the price. Alternatively, they can leave it open to the convenience of all, and receive additional compensation for doing so.
4) the maker can use a ticket system as a means to interact with the gray market and preserve the value of their caps. Makers could offer a "buy-back" option to individuals who no longer see a need for their cap, exchanging it for giveaway codes. Then such caps can either re-enter the market or be distributed at the maker's whim, grab bags, etc.
5)bonus reason::: the maker receives compensation roughly equal to market demand at point of sale. People truly get to vote with their wallets. If it's released that it's $1/entry with a max of 200 entries for a cap, and only 30 are sold, then the market has spoken. However, if all are purchased and people clamor for more, the maker made as much as they'd hoped, and frankly more than the average.
Even $50-60/cap is too steep for many, but $1-5 is a fairly easy pill to swallow, even if it ends up being $50-60 over time before one ends up winning.
Instead of putting the financial burden in the hands of 2 two people (the 1 person who buys it at "retail" when winning a raffle and the person who buys it at "market value"), the keycap maker could spread that cost across the entire playing field.
Some risks:
Administratively, it would be a lot of work. Not insurmountable, particularly with online POS platforms.
Dishonesty: obviously, the maker can just charge many people money only to fix the outcome, but there's already that risk in traditional raffles. Honor system and stuff.
The gray market can still intervene in two places: people can buy and sell codes for profit or trade, and the caps can still have a higher market value than sold. To the former point, I think people's sense of risk tolerance will be big factor, because buying an entry at 2x, 5x, 10x face "value" is much less appealing when it's not a sure thing. To the latter, that's admittedly out of the maker's hands at that point. However, by that time they should have received adequate compensation for their efforts. Also, if someone tries to corner the market by purchasing many/all tickets, the buyer and maker might as well have done an eBay auction.
Where this model succeeds in my mind is in very limited batch runs (1-5 caps), not "wide releases" (10+). Mostly, because the marketplace isn't scaled to the point where it can bear the cost of having 10+ caps sold at an assumed retail of $50-60 (meaning 500-600 people would have to be willing to enter at $1).
Sorry for the very fragmented thoughts, I'm typing this on mobile during my 5 hour layover in Phoenix. This very well could be helpful to no one, I don't care. I just want sleep.
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