One of the elephants lurking in the living room is the matter how how large the potential market is. More people eat food than purchase plants. (Your D&D start-up looks pretty neat, though.)
Think like an investor. Imagine this startup got as huge as it possibly could get and gobbled up a few adjacent markets. Could you imagine it selling to Google (or someone else) for $1B? $500m? Has there ever been any M&A activity anywhere near this market of consequence?
No doubt that there is a business here, but I think most investors look for a larger TAM as well as a market that is getting ready to blow up (or starting to).
My startup is doing something similar: a web app targeted at table-top gaming. It's not ready yet, but it has a few things Obsidian lacks, and we're looking for more coders and/or designers; if anyone is interested, give me a shout at luke at ziggurati dot net.