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A CEO coach who's worked with Twilio and Etsy says that successful leadership begins with asking yourself fundamental questions a?? not mimicking Jeff Bezos

A CEO coach who's worked with Twilio and Etsy says that successful leadership begins with asking yourself fundamental questions a?? not mimicking Jeff Bezos
Hollis Johnson/Business Insider



Jerry Colonna is a former startup investor who has been a renowned CEO coach for the last 12 years.




Colonna said that all leaders must define leadership and success for themselves before they can discover what they are trying to accomplish and how best to do so.




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For the past 12 years, Jerry Colonna has been one of Silicon Valley's most renowned CEO coaches. He draws from his long career as an influential startup investor, but he's quick to point out that he's not a performance coach you bring in for implementing new workflows. He's the guy you bring in when a founder needs a full-blown life realignment if the business is going to have any chance of moving forward.
From 1996 to 2001, Colonna ran Flatiron Partners in New York, helping to establish a startup culture in the city that would survive the dot-com bubble. He then had a stint as an investor at JPMorgan's private equity branch before founding his coaching firm, Reboot, which is also the name of his new book.
Colonna has an emotional transparency that can at times be shocking — he has spoken at length about his own battle with depression and a period in the 2000s where he struggled with thoughts of suicide — and he takes his clients to personal places they may not have even discussed with loved ones. His coaching style is based on a mix of analytic psychology and Buddhist philosophy, coupled with years of experience in the relentless, and at times brutal world, of building million- and billion-dollar businesses.
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