Reboot Podcast Episode #78 – When Did You Start to Listen to Your Heart – with Brad Feld & Jerry Colonna

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.

Episode 78 // February 22, 2018


Brad Feld

Brad Feld


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Episode Description

If you’re an avid listener of the Reboot Podcast then you are well acquainted with podcast host and Reboot CEO, Jerry Colonna. You might know that he has the particular gift of making founders cry and that he possesses the ability to drive authentic conversations with tenderness and compassion. But what makes Jerry such a great coach, leader and friend?

For this episode of the podcast, we’re flipping the script on our host, bringing in longtime friend and colleague Brad Feld to anchor a conversation in which Jerry recounts the pieces of his past that have shaped his life and led him to where he is today. Together they discuss a multitude of topics, including the power of journaling, the importance of quietness and listening, and how Jerry’s insatiable curiosity drove his career path from journalist, to venture capitalist and now to author and coach.

Brad Feld on Twitter | Jerry Colonna on Twitter 

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Show Highlights

Top Quotes:

“What I’m trying to do right now is pull myself into the present and be really real.” – Jerry Colonna

“I listen deeply to people. I hear their hearts.” – Jerry Colonna

“I would often journal in the subway. That’s when I began really being quiet and listening to everything and paying attention to things, in a really deep and profound way. “ – Jerry Colonna

“If we want to think about another attribute of my personality that really defines me and has been formative is my insatiable curiosity.” – Jerry Colonna

“I have always given a shit about people.” – Jerry Colonna

“Things are fucked up all the time like every day, continually. You can either just react to it, or you can deal with it.” – Brad Feld

“What I know to be true is that we are highly emotional and feeling sentient beings … And I also know to be true that we are socialized to pretend we’re not.” – Jerry Colonna

“I think that there are two things that I would get excited about as an investor. People and product.” – Jerry Colonna

“The answer is not actually in the spreadsheet. The answer is in the human bodies that are sitting around a particular table. Let’s make sure that those human bodies can be as present and as capable as they can be so that they can solve the ongoing ever, never-ending problems of running a damn business.” – Jerry Colonna

“I fundamentally believe going back to the people’s side of this equation that human beings who show up as leaders, fully and authentically themselves are more trusting and more trustworthy and, in the end, make better CEOs.” – Jerry Colonna

“Better humans make better leaders.” – Jerry Colonna

“I don’t want to spend minutes with people who I don’t feel are good humans.” – Brad Feld

“Good people do shitty things all the time.” – Jerry Colonna

“If you’ve got that inquiry process and you remain curious about human beings, you can, with compassion, understand and therefore protect yourself from the bad things that even good people do.” – Jerry Colonna

“You are sitting and you are gonna deal with the stuff that you have denied in your own life and you’re going to sit still until you figured it out.” – Jerry Colonna

“Every day I try to make somebody else’s life a little easier.” – Jerry Colonna

“Men at 40 learn to close softly doors to rooms they will not be going back to.” – Jerry Colonna

“This idea that people are fundamentally willing to work on themselves and that they’re there for each other especially when there’s a struggle.” – Brad Feld

“I have been helped by so many wise people in my life and if I can just pay them back by helping somebody else.” – Jerry Colonna

“When I’m dust and dried up, and I’m dead and whatever, please just keep paying it forward.” – Jerry Colonna