A donation facilitation system that can allow a donor, such as a customer, to challenge another entity, such as a provider, to make a provider contribution to a portfolio of charities set up by the donor upon, for example, the purchase of a good or service from the provider. The provided portfolio donation facilitation system can allow the other entity such as a provider to create its own provider portfolio of charities and make a provider contribution to a customer's portfolio of charities when at least one component of the provider's portfolio of charities matches at least one component of the customer's portfolio of charities.