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 152 // November 4, 2021
After a decade of working in non-profits, Philip Deng has decided to build something of his own. In this conversation, Philip sits down with Jerry to chat about his company Grantable, which helps individuals and organizations make grant writing more efficient. Philip, who identifies as Asian American, opens up about the loneliness he’s faced as a leader and CEO. He reflects on how the events of his childhood, specifically his parent’s divorce, left him with complicated feelings about his self-worth and ability to belong. Jerry supports Philip in coming to understand the ways in which he unconsciously gets in his own way and explains how the subroutines he developed during childhood (the ghosts in his machine), can simultaneously hold him back and be his greatest superpower.
Top Quotes:
“As you’re on this startup journey, you’re gonna end up in unexpected places.” – Jerry Colonna
“Was I just not trusting? Was I not being flexible enough? And is that what has made it so hard for me to find a collaborator?” – Philip Deng
“When we have an over-the-top reaction, when we have reactions that are filled with energy, emotional energy, they can be really useful inquiry points.” – Jerry Colonna
“Young boys struggle when they don’t have a male figure to identify with.” – Jerry Colonna
“I tend to avoid conflict or confrontation.” – Philip Deng
“We had enough support in a way to always kind of keep us just barely getting by, but never had enough to actually plan and hire and, and execute on what we were trying to do. So I felt like we were always treading water and buying time.” – Philip Deng
“When the struggle was painful, I felt like I deserved that pain. Which kept me from asking for what I needed.” – Philip Deng
“One of the consequences of a white supremacist society can be a deep struggle to feel worthy and deserving of any success.” – Jerry Colonna
“The part of you that was wounded led to a part of you that sought to heal that wound through external affirmation.” – Jerry Colonna
“Because of your complicated relationship with whether or not you personally have the resources, it stands to reason that the teams that you lead may also suffer from a lack of resources.” – Jerry Colonna
