Reboot Podcast Episode #145 – Facing the Monster (in Your Head) – with Suneel Gupta

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.


Suneel Gupta

Suneel Gupta

Author, Professor, and Co-founder and CEO of RISE

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Episode Description

Suneel Gupta is an entrepreneur, Harvard professor, and author of “Backable: The Surprising Truth Behind What Makes People Take a Chance on You.” In this episode, Suneel chats with Jerry about his personal struggles with fundraising and how it led him to attend a Reboot Bootcamp. They host a larger conversation around identity, the way our fears keep us small and safe, and why living and leading from our fullest selves requires confronting the monster in our head.

Backable: The Surprising Truth Behind What Makes People Take a Chance on You | CEO Jerry Colonna | Code Conference 2019 | Milarepa – Eat Me If You Wish

Show Highlights

Top Quotes:

“I think one of the things that I took from Bootcamp that has always stuck with me is that you are not your startup.” – Suneel Gupta

“Do you want to be a second rate version of somebody else or do you wanna be a first-rate version of you?” – Suneel Gupta

“I think so much of our twenties are defined by this push me, pull you kind of relationship with our family of origin in which we are trying to either define ourselves in accordance with or in opposition to.” – Jerry Colonna

“You wanna know the most backable quality? It’s presence. It’s like living from your solar plexus and being fucking real.” – Jerry Colonna

“You can try to tuck fear away, put it in a room and lock it away but the banging is just going to get louder and louder and louder. At some point in time, you’ve got to open that door and you’ve got to look at it and you’ve got to inspect it closely enough to realize that a lot of what it’s telling you probably doesn’t have a lot of basis.” – Suneel Gupta

“When you endeavor to answer those big questions, what you’re really doing is turning around and facing the demon that’s chasing you.” – Jerry Colonna

“Of all the qualities that one would say is backable, it’s being yourself.” – Jerry Colonna

“We all get tripped up by trying to define ourselves in opposition to, or in accordance with who we see as entrepreneurs or who we see as successful leaders or who we think we’re supposed to be as adult.” – Jerry Colonna