Diligence Through Community Participation

Diving deeper into

Q&A with Raihan Anwar and Colby Holliday from Friends with Benefits

Interview
these people demonstrated what they knew about us rather than us pitching to them.
Analyzed 2 sources

This round shows that FWB was being financed like a living network, not a cold start startup. The investors had already spent time inside the Discord, bought tokens like everyone else, attended events, and formed a view on the product from direct use. That matters because FWB was selling access to a community, media layer, and token gated tools, so the best diligence was to participate and see whether the culture actually produced products, demand, and durable member behavior.

  • FWB had already built concrete proof points before the round. It ran token gated parties, shipped custom Discord tooling, operated membership, editorial, treasury, and product teams, and grew to nearly 2,000 members. Investors could inspect the system in action instead of relying on a deck.
  • The investor set was intentionally shaped to avoid pure token speculation. FWB says investors were long time members who bought their way in, took lockups, and in some cases delegated voting power so a large holder could not simply use wallet size to steer the community.
  • This looked more like backing an ecosystem from the inside than buying a position from the outside. a16z framed FWB as a bridge between internet community and real world experiences, which matched what members were already doing through events, newsletters, and creator collaboration.

Going forward, the winning investors around tokenized communities will look less like buyers of exposure and more like power users who can help the network grow without breaking its social fabric. That model points toward community financings where diligence is participation, and where governance structure matters as much as price.