From a grocery counter in Utah to the founding of JetBlue, David Neeleman has built a career around the small indignities of travel. At Breeze, his fifth airline venture, he is still looking for the routes everyone else has left out.

Before she ran JetBlue, Joanna Geraghty learned its business through lawsuits, people and the departure gate. Now she is testing whether an airline can improve its finances while keeping its human touch.

From an early digital-advertising startup to two public-company debuts and Noom, Peter Scherr has built a career around one unfashionable marketing principle: the experience must work before the story can travel.