The Wright Brothers
Before beginning their career in the business of flight, the Wright Brothers, with no high school diplomas and no college education, started the “Evening Item,” a daily new paper that flopped quickly. Next came a dive into the business of making and selling bikes. While nominally successful, the Wright Brothers had still not found their passion and closed this company as well.
When they finally started attempting to develop the first manned flying machine, they went through dozens of designs before landing on one that they would even try to put a man in. And when they did, many crashed and one leaving Orville severely injured and a passenger dead.