#767: Jerry Colonna — Tim and Uncle Jerry Tackle Life, Big Questions, Business, Parenting, and Disco Duck
The Tim Ferriss Show
Tim Ferriss: Bestselling Author, Human Guinea Pig
4.6 • 17.7K Ratings
🗓️ 11 September 2024
⏱️ 103 minutes
🧾️ Download transcript
Summary
Here is my brand-new conversation with Jerry Colonna, CEO and co-founder of Reboot.io, an executive coaching and leadership development firm dedicated to the notion that better humans make better leaders. He is the author of Reboot: Leadership and the Art of Growing Up and Reunion: Leadership and the Longing to Belong. Enjoy!
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[00:00] Start
[08:40] “How have I been complicit in creating the conditions I say I don’t want?” and its misinterpretations.
[21:55] Recharging off the grid on sabbatical.
[24:41] Is a tired dog a happy dog?
[29:21] What are you hearing that’s not being said?
[33:14] Closing transgenerational, transpersonal, and intergenerational wounds.
[44:05] Focusing on the future when the past keeps pulling us back.
[52:18] Changes in challenges Reboot’s clients have faced over the past decade.
[55:34] Guilt vs. remorse and how to move from one to the other.
[1:01:40] Interpretations of legacy.
[1:13:17] Jerry’s parenting experience and advice.
[1:19:02] My thoughts on having children and grandchildren.
[1:24:54] “This Be the Verse” by Philip Larkin.
[1:26:08] Book recommendations and their impact on Jerry and his children.
[1:28:46] Novel truths.
[1:32:40] The importance of laughter and human connection in difficult times.
[1:35:45] Parting thoughts.
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Transcript
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| 0:00.0 | Hello, boys and girls, ladies and germs. This is Tim Ferriss. Welcome to another episode of the Tim Ferriss |
| 0:04.6 | show, where it is my job to deconstruct world-class performers to interview them and tease out |
| 0:09.5 | the habits for teens, favorite books, and so on, that you can apply to your own lives. Sometimes I get, |
| 0:15.5 | not just a two-for-one, but a hundred for one, when I interview someone who also helps world-class performers in addition to being |
| 0:22.7 | such themselves to get past sticking points, to redefine themselves, to reinvent themselves, |
| 0:28.7 | to chart new paths forward. And my guest today, Jerry Colonna, is such a person. He is the CEO |
| 0:34.6 | and co-founder of reboot.io, an executive coaching and leadership development firm, |
| 0:38.7 | dedicated to the notion that better humans make better leaders. But prior to that, he was an |
| 0:44.0 | operator in many different ways. Prior to being a coach, he was a partner with J.P. Morgan |
| 0:48.4 | Partners, the private equity arm of J.P. Morgan Chase. He also led New York City-based Flatiron |
| 0:53.9 | Partners, which he founded in 1996 |
| 0:55.8 | with partner Fred Wilson. Flatiron went on to become one of the nation's most successful |
| 1:01.0 | early-stage investment programs. At age 25, he was editor-in-chief of Information Week magazine. |
| 1:06.1 | He's written a bunch of books. We'll mention them at the end of the conversation, but one is |
| 1:09.9 | reboot. The other is |
| 1:10.9 | reunion, both highly recommended. You can find his company reboot at reboot.io. And Jerry on |
| 1:17.6 | Twitter and Instagram at Jerry Colona, C-O-L-O-N-A. And he has been on the podcast twice before. |
| 1:25.6 | He is a fan favorite. People always take a ton away from our conversations, |
| 1:29.7 | and I recap some of my favorite aspects of those in this episode. And we cover a lot of ground. |
| 1:36.2 | There are a lot of stories I've never heard. We have a lot of laughs, almost a few cries on my side. |
| 1:43.6 | We dig into his toolkit. The questions that he uses with himself |
| 1:47.9 | and with clients that I have adopted is some of my favorites. There is a lot to learn, and it was a hell |
... |
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