Summary: Each round represents a year, and each die in a player's dice pool represents some some software capability that either generates annual recurring revenue, or a support burden.
Setup:
Gather a big pool of D&D dice, ranging from d4 to d20, or use the Google dice roller.
Get a piece of paper to keep score. Write each player's name across the top, and the rounds (1-10) along the left side
Pick a random player to start
Game Play:
The current player decides between one of two actions:
Add a new d4 to their "revenue" dice pool.
Upgrade an existing die to the next level (d4 to d6, d6 to d8, etc....).
Players take turns making this decision, passing to the left, until all players have chosen an action.
Once all players have chosen, they roll all the dice in their revenue dice pool
For each die that is not a one, the player scores a point. This represents annual revenue. Add this to a running total for the player.
Each die that is a one moves into a separate "legacy" pool. A player with dice in their legacy pool cannot add new dice, or upgrade dice in their revenue pool on their turn. Instead they can only move one die from their legacy pool into their revenue pool.
If _all_ the dice in a player's revenue pool roll a one, this represents a catastrophic failure. The player's score total is reset to zero.
The starting player position shifts one to the left.
IF ROUNDS < 10 GOTO #1
After finishing the 10th round, add up the scores for all the players
I've play-tested this exactly three times, using three different strategies: