Ask for the Keys
Lawson likes to tell a story about his grandfather, who worked in a factory and needed to earn more money.
"He went to the owner and he said, 'I need to make more money, how do I do that,'" Lawson said. "The guy said 'I don't have any other jobs. The only job I have is driving the truck. Do you know how to drive the truck?' My grandfather's answer was, 'Give me the keys.'"
What his grandfather didn't mention was that he'd never driven a truck before in his life. But he got the job, figured it out, made more money.
Chalk it up to genetics or coincidence, but in middle school Lawson started a company shooting video footage of weddings. Then, he used the proceeds to buy more sophisticated equipment.
"The best way to learn something new," he said, "is to commit yourself to doing it."
You've Got to Love It
There were some false starts. In college during the dotcom boom, Lawson learned software development and started a company that sold for millions of dollars … in stock. He thought he'd made it big, but when the bubble popped, his windfall vanished.
Later, he got the opportunity to be founding chief technology officer of StubHub, a ticket sales company that would later sell to eBay for $310 million. But Lawson didn't stick around for the payoff.
"It was a fine business, but I wasn't the customer and I didn't feel passionately that the world needed the product we were building." He wasn't a concert goer, so he didn't feel inspired to keep working on it. "As an entrepreneur, I think you need that."
Hindsight being what it is, it's easy to fault Lawson for missing his share of a nine-figure payday. But remember, he's got a share of a 10-figure payday in Twilio.
Knowledge and Reputation
So how did Lawson do it? How did he rebound from a missed nine-figure payday cleanly enough to do himself one better? First he made another valuable mistake or two, which you'll learn about listening to this Fortt Knox episode.
More important though, he was able to focus on the two most important assets he was building in each of these experiences.
"The best thing that we have as we go through our careers is our knowledge and our word – our reputation," Lawson says. "If you're constantly building those two things, I think generally speaking, good things end up happening to people."
Fortt Knox is a weekly podcast from CNBC anchor Jon Fortt. Previous episodes of the program can be found here.