DAICO and Iterative Investment

Sounds good. Small investments over time, e.g. with paychecks, are much more financially sound than a big one-off investment, and are less risky, and as you say the discount on investment or price of tokens can increase as the project moves forward, returns increase and risk reduces. I think the use of a governance protocol like Democracy Earth or Holographic Consensus would also help with iterative investment. The organization could set in its code a quorum for investors to vote on a budget, as well as other rules.

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