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Dive deep into your challenges: Leadership author

Chelsea Lombardo
Production Assistant

What does it take to become a successful CEO? Venture capitalist–turned executive coach, Jerry Colonna, believes he has the answer.

Colonna, the CEO and co-founder of Reboot.io, joined Yahoo Finance’s The Final Round to discuss his latest book, “Reboot: Leadership and the Art of Growing Up.”

“Leadership is super hard,” says Colonna. “It challenges us in ways that people just don’t expect. Rather than giving up on that, my advice often is to dive deep on that. Because within those challenges is an opportunity to complete a process of actually becoming an adult and growing up.”

Colonna has held top roles in the business world for over half of his life: At 25, he was InformationWeek’s editor-in-chief; at 40, he was a partner at JPMorgan; and in addition to his current role at Reboot.io, he’s the co-founder of VC firm Flatiron Partners.

Portrait of male CEO in big corner office, looking out of window, at sunset

“Whether it’s a first-time CEO in their early twenties trying to figure things out or whether its somebody who’s in their mid-forties and this is their second or third time ... it’s hard for everybody. The opportunities to grow are the same for every single person."

Colonna is known for his “Reboot Bootcamps,” which have earned him the nickname “The CEO Whisperer” from Gimlet Media. His methods demand that participants confront their psychological baggage which, according to Colonna, stunts many executives’ ability to run their companies effectively, and accomplish their overall goals.

“When we’re five years old or ten years old, we lay certain beliefs systems about the world,” he explained. “Well guess what the culture at our culture is going to be at the company? It’s going to reflect that.”

And the one lesson readers should take away from Colonna’s book? “You can do this, and you can grow.”

Chelsea Lombardo is a Production Assistant for Yahoo Finance. You can find more of her work here. Olivia Balsamo is a Producer and Writer for Yahoo Finance. You can find more of her work here.

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