If you ask Everette Taylor how he became CEO of crowdfunding platform Kickstarter, he'll tell you: "I got lucky."
The 34-year-old spent a chunk of his teen and young adult years battling homelessness and hustling to make ends meet, he says. He dropped out of Virginia Tech and founded an event marketing startup. Then, he sold the company and landed a VP of marketing job at another startup.
Taylor parlayed those experiences into a career in serial entrepreneurship and marketing strategy, ultimately helping him land the top job at Kickstarter in September 2022. Two soft skills helped him navigate that journey, he says: empathy and risk taking.
"I'm driven by risk," he tells CNBC Make It. "And in terms of getting me to where I am now, empathy is key."
Here's why Taylor says risk-taking and empathy are so important, and how you can cultivate both skills.
'Every failure is a part of the puzzle'
As a child, Taylor was fearless — at least, that's what his mom tells him, he says.
As an adult, his approach to risk is more calculated. "I take a step back and say that if I take this path, or I take this [other] path, this is where my life is going to end up," Taylor says. "My appetite for risk is higher, because I know that the impact that I want to leave on the world and the people around me requires taking chances."
At Kickstarter, Taylor recently implemented a four-day workweek for his employees, a risk that comes with pros and cons. It can improve employee productivity and morale, according to businesses that have tried it. It can also hinder time management, pose scheduling challenges and cause burnout, Boston University organizational psychologist Constance Hadley told the school's website last year.
For now, it's paying off, Taylor told Time in June: "We've been just as productive or even more productive with a four-day workweek."
Other risks aren't worth taking, Taylor says. He regrets selling drugs as a teenager, a job that could have landed him in jail if his mother hadn't intervened and "really forced me to get a [real] job," he told LinkedIn's "The Path" newsletter in June.
That job was as a junior marketing assistant for bookstores and museums across Virginia, the first step in a marketing career that eventually led to Taylor's CEO position. His takeaway: Embracing your failures can make taking risks less scary.
"Every failure is part of the puzzle that leads you to the overall picture that is supposed to be your life," Taylor says now. "[I don't] focus on what could go wrong. I think more optimistically. There's always going to be another job, there's always going to be another opportunity out there. Why not go for it when you can?"
Empathy is an 'essential skill set'
Taylor uses his childhood as a reminder to approach all situations — personal and professional — with empathy, he says.
"The ability to put yourself in the shoes of your customers or your potential customers is literally the essential skill set that a marketer has to have," says Taylor. "And as a leader, your ability to be able to empathize with the people that work with you, and work for you, is [equally] essential."
As a boss, that means understanding that your employees and clients are "more than their work." If someone is dealing with a family emergency, the first thing Taylor wants them to know is that he cares, he says.
"The way that you communicate with people, the way that you show that you care, the way that you show that you want to help build people up and empower them, those all go a long way," he says, noting: "It helps you become a better leader ... and really helped me get to where I am today."
Developing empathy starts with genuine curiosity about another person, asking them questions, and really paying attention to their responses.
"Listen both for the words being said and the feeling behind them," psychologist Daniel Goleman told CNBC Make It in 2017. "Respond accordingly, with a sign that you understand, or offer a helpful comment."
"One conversation won't boost your empathy," Goleman added. "But over time, exercising your curiosity and listening closely to others will help you sense more accurately how others think and feel."
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