This chapter presents a dialogue between Japhet Makongo, a community development worker based in Tanzania, and Lin Bender, CEO of the philanthropic organisation, the Helen Macpherson Smith Trust in Victoria, Australia. Lin and Japhet have each worked on both ‘sides’ of the funding relationship and through their discussion they offer insights into the day-to-day realities of managing funding relationships. They analyse the risks and challenges involved, but also the possibilities for effective funding for community empowerment. Their discussion of funding speaks to perennially important themes within community development such as power, agency, community ownership, process versus outcome, and the meaning of ‘success’.