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Paul – FS Concierge
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I am not sure that you are asking the right questions or that the assumptions behind them are correct.

It is notoriously hard to get traction in two way marketplaces because you have to win the trust and have front and back ends that suit both sides.

If I were to do it, I would choose a niche based on a real problem I know many have or by finding a significant efficiency not easily (or at all) in the existing marketplace.