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Is it better to raise all the money we need for the initial period, plus a 'cushion', or to ask for enough to get started initially and then come back when we have six or 12 months' trading experience?

Raise all the money you need, plus a cushion - depending on what sort of business it is, 10-25 per cent of the total. If you attempt to come back to your bank (or to investors) too soon, they are likely to assume that you have run through the original funding more rapidly than was projected, and have not begun to generate income to sustain the business. None of this is going to encourage them to make more cash available.