Chip Mahan travels with an entourage. The 62-year-old community banker is leading them now—five men, all of them cheery, but exhausted—in a single-file procession across the tarmac and up the airstairs. It's midafternoon on a typical work day for these atypical small-business lenders, who are returning to Wilmington, N.C., after an overnight visit to Boston. They met the day before with Fidelity to talk about the idea of a partnership that could give their $337 million-asset Live Oak Bancshares access to thousands of new borrowers, if a deal is struck.

Mahan plays steward as they board the Gulfstream G200, handing waters to everybody before sinking into one of the white leather seats himself. The plane is in use almost daily. On a recent three-day trip, this crew followed Mahan, Live Oak's chairman and CEO, to Minneapolis, Portland, San Francisco, San Diego, and finally to Las Vegas, before heading home.

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