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By Weintraub's own account, he phoned Colonel Tom Parker almost daily for about a year asking to take Elvis Presley on tour, and was refused every time. Parker finally named terms meant to end the conversation: a cashier's check for one million dollars, delivered in Las Vegas on a tight deadline. Weintraub raised the money in time, got the tour, and built his career on it, though his telling is a showman's version polished over many retellings.
A gatekeeper's repeated no often means you have not yet shown enough commitment or met a price nobody has named, rather than a permanent verdict. Staying in contact keeps you as the default candidate when the gatekeeper's circumstances change. Deliberately extreme conditions are often a filter, and meeting them turns a brush-off into a binding promise.
Weintraub treated a performer's tour as one centrally run national product rather than a string of local bookings. One operation handled routing, arenas, advertising and ticketing across the country, which captured the margins local promoters used to take and gave the artist a consistent show. The value lay less in owning the talent than in controlling the logistics between the talent and the audience.
Weintraub presents his deals as running on personal loyalty, favors and phone access more than on legal terms. On this view, the dealmaker's real asset is a network of people who will take his call and remember what he did for them, and that is what turns one success into the next.