Lesson #4: Learning by Doing is the Better Way

“[I] learned it by doing it,” says Kelleher, “and I was scared to death.”

When Kelleher first stepped up to run the company on a permanent basis, not everybody was thrilled with the idea. How was a lawyer with no business background going to run a national company, they wondered. “I stayed up all night familiarizing myself with its problems,” he said. “PATCO (the air-traffic controllers’ union) had just pulled 13,000 controllers out of the towers. We had six new airplanes coming. One of the analysts with Oppenheimer downgraded the stock when I moved in because he said I was a lawyer – and lawyers couldn’t run anything.”

Lawyers could not run anything? Kelleher begged to differ. “I told him: [A top executive] from U.S. Airways is going to be peeved with you,” recalls Kelleher. “And he said: How come? I said: He’s a lawyer. He said: I never knew that. So we chatted for a spell, and then he wrote another piece and said he thought Southwest was going to be ok – despite the fact that it was headed by a lawyer.”

Kelleher never let his lack of experience get in the way of his ambitions. If somebody said he could not do it then that was only more reason to prove that he could. “I was always motivated,” he says. “Even the things I wasn’t supposed to do, I undertook with great energy, dedication, and perseverance.”

One of those things that Kelleher was not supposed to do was start an airline company. He was a lawyer from New Jersey with no business background. What gave him the right to think he had what it would take to run an airline in Texas?

“Everybody in Texas would tell me that they thought I was nuts trying to start Southwest Airlines,” he recalls. “There probably weren't 10 people in the state who would have given a plug nickel for our chances of making a dollar. So sometimes, you need a little courage, too, just to buck popular opinion.”

Courage and ambition made up for whatever shortcomings Kelleher had in the business world. But what about in today’s business world? Is that really all one needs to start up a successful company?

“I think it was easier to be an entrepreneur in the '30s than it was in the '60s and '70s, and I think it was easier in the 1890s than it was in the '30s. As society becomes more regulated, it becomes more difficult to launch entrepreneurial ventures,” he says. “It’s harder today – but not impossible.”

What are the secret ingredients? “You must be very patient, very persistent,” says Kelleher. “The world isn't going to shower gold coins on you just because you have a good idea. You're going to have to work like crazy to bring that idea to the attention of people. They're not going to buy it unless they know about it.”

And, above all else, make sure you have a plan in place to get your dreams off the ground. “You're going to have to have probably five times as much capital as you thought you would,” says Kelleher. “Because if you're an entrepreneur, you're optimistic by nature. So you think, in six months, we're going to be sailing. But that optimism causes you to raise a lot less capital than you need in most cases, and it's very lonely.”

Lesson #4: Learning by Doing is the Better Way

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