How Reboot Founder Jerry Colonna Coached CEOs of Companies Such As Soundcloud and Etsy To Help Them Reach Their Full Potential


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By Eric Siu. Discovered by Player FM and our community — copyright is owned by the publisher, not Player FM, and audio is streamed directly from their servers. Hit the Subscribe button to track updates in Player FM, or paste the feed URL into other podcast apps.

From the outset, the business world looks like it’s filled with brilliant people who can turn anything into a success. This can be disheartening but Jerry Colonna, Executive Coach and CEO whisperer, has a secret to tell you — most people are faking it. Today we speak with Jerry about how you can become a better leader on your terms, without needing to compare yourself to others. We open our conversation with a discussion on why many founders and marketers need support, often from coaches, before Jerry provides some insights into why you should look for an effective coach, not necessarily a coach with accolades. A key theme of this episode, Jerry highlights that a coach’s job isn’t to give you all the answers. Rather, they should help you discover your own solutions by asking the right questions. We then dive into how Jerry has coached host Eric Siu, with Jerry sharing details about his coaching philosophy. From there, we explore the business model for Jerry’s company, Reboot, the services they offer, and how they offer an entry-point for any user, regardless of their means. Reflecting on his life as a venture capitalist, Jerry talks about the benefits of living a slower life, why “Comparison is the thief of joy,” and what quality is common among successful leaders. Near the end of the episode, he shares how he maintains his mental and physical wellbeing, along with the top books that have altered the course of his life. Tune in to hear more of Jerry’s expert advice on how you can become a better leader.


  • [00:00] Before we jump into today’s interview, please rate, review, and subscribe to the Leveling Up Podcast!
  • [00:18] Introducing Executive Coach and CEO whisperer, Jerry Colonna.
  • [02:02] Why all founders and marketers need support; “Nobody is crushing it.”
  • [04:36] Fixing versus coaching and why effective coaches aren’t always the most acclaimed.
  • [06:41] The idea of gestalt and asking good questions instead of giving advice.
  • [07:45] Insights into how Jerry runs his coaching sessions and how he sees his role as a coach.
  • [09:45] How Jerry has helped host Eric Siu to slow down and lead with more wisdom.
  • [11:51] Overcoming your sub-routines to improve your operating system.
  • [13:52] Unpacking lessons from the gaming world and why they don’t apply to other contexts.
  • [16:10] Hear how Jerry’s business works and the services that he offers.
  • [18:15] From free resources to reading his book, Jerry shares the best ways for listeners to start with Reboot.
  • [19:42] Jerry compares his life as a coach to his life as a venture capitalist.
  • [22:22] In praise of the ‘infinite game’ and trying to be kind every day.
  • [24:16] The benefit of living your life without comparing yourself to others.
  • [25:57] Learning how to ask better questions, a skill that makes you a better leader.
  • [28:29] Why you shouldn’t ask a question with judgment or expectation.
  • [29:49] The common attribute that Jerry sees in his best students.
  • [30:51] What Jerry does to maintain his mental wellbeing and keep his skills sharp.
  • [32:51] Jerry shares the top books that altered the course of his life.
  • [34:21] How to find Jerry online.

Resources From The Interview:

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