The Reboot Podcast

Website: https://www.reboot.io/podcast/

Description: The Reboot Podcast showcases the heart and soul, the wins and losses, and the ups and downs of leadership.

Beyond spreadsheets and strategy lies the beating heart of leadership. The Reboot Podcast isn’t just about business; it’s about the soul of building something meaningful. Join Jerry Colonna and other members of Team Reboot as they go deep with entrepreneurs, CEOs, and leaders like you, exploring the emotional journeys we all face.

Forget the sanitized success stories. Here, we dive into the wins and losses, the triumphs and breakdowns, the moments where vulnerability and courage dance on the edge of the unknown.

Each episode is a raw conversation, a shared experience. From imposter syndrome to burnout, major transitions, anxiety, and even co-founder conflict, no challenge is off-limits. You’ll find laughter, tears, and moments of profound wisdom as you discover tools and strategies to navigate the emotional rollercoaster of being a leader to today’s complex world.

This isn’t just a podcast; it’s a community. Whether you’re seeking inspiration, practical tips, or simply a reminder that you’re not alone, we’re so glad you’re here.

Host: Jerry Colonna and other members of Team Reboot

Jerry Colonna is a trusted coach, consultant and confidant to some of the startup communities’ biggest names including Brad Feld, David Cohen, and Fred Wilson. Jerry’s work with CEOs teaches the art of authentic leadership: leadership that cultivates positive company culture; happier, healthier CEOs and strong, successful companies.

Format: Conversation with Guest

Medium: Audio

Show Contact: hello@reboot.io

Example Episode Detail

Reboot Podcast #172 - Finding Closure After Shutting Down the Business - with João Barros & Jerry Colonna

There’s more to leadership than building the next billion-dollar unicorn. Our guest, João Barros, has walked a fascinating path – from professor to CEO and back again. In this candid conversation with Jerry, João reflects on his entrepreneurial journey, making the gut-wrenching decision to close down his business, and how attending a Reboot Bootcamp empowered him during this difficult time.

Join us as we challenge conventional success paradigms, honor diverse paths to leadership, and highlight why João embodies the essence of a servant leader. Discover why embracing change and letting go can lead to the most profound lessons.

Memorable Quotes

“Everybody always says to me, well, what does it mean to do the work? It means leaning into the tough spot of, ‘Oh, shit. I don’t know what I’m doing.’ And all of the feelings that come from that.” – Jerry Colonna

“The Bootcamp was the moment where I finally gave myself permission to think what is the intersection between what the company needs, what you need, and what your family needs, and how do we get to that point.” – João Barros

“I just realized if my marriage and my family are okay, if we’re doing well, if we’re as close-knit as we usually are, then everything else is easier. Whereas, if that’s not working, then everything else, has no chance of succeeding.” – João Barros

“The truth is also that the CEO job was forcing me to do a lot of things that are actually not part of my nature. I didn’t I didn’t feel myself for a very long period of time.” – João Barros

“I am still trapped in that Silicon Valley storyline…you’re only successful if you create a unicorn and everybody celebrates the huge, massive valuation of your company. But I also tell myself that, in the end, I was honest with everyone that I dealt with, and I did the best I could. And that has to be enough.” – João Barros

“Before you start something, write down your definition of success before you actually embark. Lots and lots of people will tell you what success means, but if you have your own definition that you wrote down before everybody else tells you what success is, then at the end of the journey, you can go back to that and just say thank you for reminding me that that of the starting point and what we set out to do.” – João Barros

“Oftentimes, I will say that the hallmark of a good leader is the number of leaders that they help create. I’ll expand that right now. The hallmark of values-driven leadership is the DNA of those values continues to spread.” – Jerry Colonna

“Closure is a process. It’s not something that you flip a switch and then all of a sudden those feelings change. The process is about revisiting and remembering. Re-membering that which has been disconnected.” – Jerry Colonna