Generally it means you have an entrepreneurial track record, but it could also mean you have amazing investor connections, an executive track record of tremendo

Generally it means you have an entrepreneurial track record, but it could also mean you have amazing investor connections, an executive track record of tremendous success in a relevant business, an EIR arrangement where the VC wants to fund you, etc. Going from nonfundable to fundable or from a premoney valuation of x to 2x (which is what someone should do to merit this sort of disproportional value) gets rewarded by a corresponding increase in ownership.