Reboot Podcast Episode #140 – From Heartbreak, Through Resilience, To Equanimity – with Chad Dickerson

The Reboot podcast showcases the heart and soul, the wins and losses, the ups and downs of startup leadership. On the show, Entrepreneurs, CEO’s, and Startup Leaders discuss with Jerry Colonna the emotional and psychological challenges they face daily as leaders.

Guests

Chad Dickerson

Chad Dickerson

Executive coach, and former CEO of Etsy

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Episode Description

In this fresh release, Jerry sits down with past client, former CEO of Etsy, and fellow executive coach, Chad Dickerson. In this episode, Chad describes the shift from CTO to CEO and the anxiety he experienced in the months after his transition. He gives insight into some of the unique challenges he faced in his six years as CEO of Etsy and opens up about his painful departure from the company. Jerry and Chad contemplate what it means to lead with compassion, humanity, and integrity and consider how moments of heartbreak delivers greater resiliency and cultivates equanimity.

B-Corp

 


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Show Highlights

Top Quotes:

“You’re one of those rare characters who changes the job more than allows the job to change you.” – Jerry Colonna

“Sometimes being a leader, you have to go in and fix things in a way that maybe doesn’t make people happy.” – Chad Dickerson

“What Etsy seemed to have was skilled engineering talent, but what I saw you doing, and then ultimately doing for the rest of the organization, was focusing on culture.” – Jerry Colonna

“When I came in, it didn’t really feel like the engineering team was connected to the larger mission and culture of the company, which is all about making and craft.” – Chad Dickerson

“The challenge of that team in the early years and the years I was there was always about taking this relatively chaotic kind of disparate place and trying to unify it into one coherent unit.” – Chad Dickerson

“My first day as CEO it was as if the clock set to zero, all the work I’d done in engineering was still important, but it wasn’t the thing that mattered anymore.” – Chad Dickerson

“When you step into the top job, it’s not one notch up the ladder. It’s like six.” – Chad Dickerson

“I think when you’re a CEO, there’s just no time to waste. There’s a lot of work to be done and you have to immediately start prioritizing around team and initiatives and it’s very challenging.” – Chad Dickerson

“I’m still really happy about this. I didn’t  sacrifice the kind of core principles of honesty and being straightforward that I wanted in the company, especially at a moment when we were becoming a B Corp.” – Chad Dickerson

“Resilience is almost like lifting weights. The more weight you lift, the stronger you get.” – Chad Dickerson

“I was very honest and insisted that publicly we say that I was fired, but it was more like an excommunication.” – Chad Dickerson

“As I was leaving, I wasn’t thinking about the hotshot CEO lifestyle,  I was thinking about the people inside the company.” – Chad Dickerson

“At every moment I was trying to act with integrity and there were moments where I made conscious decisions that were less beneficial to me because I thought they were the right thing.” – Chad Dickerson

“Pausing and not trying to get back into the “game”, made me think about what the game is that I wanna play.” – Chad Dickerson

“I think it’s tragic, especially as you get into the second half of your life to ignore those fundamental impulses of what you really want to do and what you really wanna be out of deference to somebody else’s idea of what you should be.” – Chad Dickerson

“Your job is part of a mosaic of who you are. You have to make sure that it doesn’t consume your entire self because other things that are more important can get sacrificed. – Chad Dickerson

 


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