Reboot Podcast Episode #156 – Safety and Trust: The Crux of Adult Relationships – with Brad Feld & David Jilk

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.


Brad Feld

Brad Feld

Author, Co-founder of Foundry Group & Techstars

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David Jilk

David Jilk

Author & Startup Advisor

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Episode Description

At Reboot, we firmly believe that the act of leadership affords everyone the opportunity to grow into their most adult selves. Inquiring radically into our own psychologies and facing up to the truths behind our behavior allows us to lead and relate to others from a more informed place.

In this podcast, Jerry sits down with Brad Feld and David Jilk, co-authors of Entrepreneur’s Weekly Nietzsche: A Book for Disruptors. The duo, who’ve shared a personal and professional relationship for nearly forty years, share why collaborating effectively requires honesty, respect, and the ability to lean into healthy conflict when it arises. Jerry, Dave, and Brad emphasize the importance of setting, communicating, and honoring boundaries, and highlight why safety and trust are at the crux of all healthy, adult relationships.

Show Highlights

Top Quotes:

“I probably had more interest in the working relationship and the opportunity to try to create something from nothing from an idea than I did about the specific outcome and characteristics of what was going on.” – Brad Feld

“I’m a big fan of people looking at their own psychology and looking at their own experience and facing up to some dark truths about your own behavior.” – Jerry Colonna

“One of the theories that I work with all the time is that the experience of being a leader actually gives us an opportunity to really look at ourselves honestly, to say to yourself, “Who am I supposed to be?”- Jerry Colonna

“Allowing the other person to get to a conclusion on their own was something that I need to create space for.” – Brad Feld

“Part of our friendship is that we knew that when we were working together professionally that we trusted each other not to just do stuff because we’re friends.” – Dave Jilk

“You trust each other enough to profoundly disagree if you need to. You trust each other enough to know in advance the best way to navigate this relatively complex relationship.” – Jerry Colonna

“When I’m mentoring or advising companies, it’s not so much just that they’re in it for themselves only, but rather that they don’t even seem to be capable of thinking about the relationship as an aspect of it.” – Dave Jilk

“ When there is something that Dave does that is bothersome to me, he doesn’t have to wonder whether he’s crossed a boundary or not. He trusts that if he has, I will make a comment about it.” – Brad Feld

“Being a leader is an opportunity to grow the hell up. It’s the opportunity to look at the monsters that you speak to, that Nietzsche speaks to, to look at the parts of ourselves that we really don’t wanna look at.” – Jerry Colonna