Jerry Colonna — The Coach with the Spider Tattoo (#373)

“You are not alone. And just because you feel like shit, doesn’t mean you are shit.” Jerry Colonna

Jerry Colonna (@jerrycolonna) is the CEO and cofounder of, an executive coaching and leadership development firm dedicated to the notion that better humans make better leaders.

Prior to his career as a coach, he was a partner with J.P. Morgan Partners (JPMP), the private equity arm of J.P. Morgan Chase. Prior to that, he cofounded New York City-based Flatiron Partners with Fred Wilson, which became one of the nation’s most successful early-stage investment programs. His first leadership position, at age 25, was Editor-In-Chief of InformationWeek magazine, and now he has returned to the written word with his first book, Reboot: Leadership and the Art of Growing Up.

Listen to the episode on Apple Podcasts, Spotify, Stitcher, Overcast, Castbox, or on your favorite podcast platform. You can find the transcript of this episode here. Transcripts of all episodes can be found here.

#373: Jerry Colonna — The Coach With the Spider Tattoo

Want to hear an episode with someone else who understands the value of coaching? Listen to my conversation with Eric Schmidt, in which we discuss the immeasurable impact late coach Bill Campbell had on Silicon Valley’s rise as a veritable modern superpower. (Stream below or right-click here to download.)

#367: Eric Schmidt — Lessons from a Trillion-Dollar Coach

QUESTION(S) OF THE DAY: What was your favorite quote or lesson from this episode? Please let me know in the comments.

Scroll below for links and show notes…


  • Connect with Jerry Colonna: | Twitter


  • What’s the story behind Jerry’s spider tattoo? [05:10]
  • What happened at an Olympic bid meeting in 2002 that would change Jerry’s life? [11:39]
  • Jerry talks candidly about a suicide attempt at age 18 and spending three months in a psychiatric hospital. [18:17]
  • What’s the difference between responsible and complicit and, in 2002, how was Jerry complicit in creating the conditions in his life that he would have said he didn’t want? [19:30]
  • Three important questions Jerry’s therapist taught him. [23:02]
  • An example of something Jerry needed to say during this period of time that he didn’t say or that wasn’t heard. [24:24]
  • What did Jerry do to overcome the nagging self-doubt and unanswerable questions that were crushing him at this point? [26:12]
  • How did Jerry find his way to coaching, and what three books guided him in that direction? [28:42]
  • If he were to hazard a guess, how much of Jerry’s call to coaching was finding relief in taking the focus outside of himself and, in a way, healing his younger self? [35:12]
  • How does Jerry get through to fellow high-achievers who don’t think they have the time, patience, or need for self-discovery? [38:30]
  • The first question Jerry asks: “How are you really feeling?” [39:41]
  • How does Jerry work with the chronically busy? [43:11]
  • Jerry takes a look at how I’ve historically dealt with busyness and breaks it down — along with saying “No” and when (and why) this is most difficult for me. [45:54]
  • There are three basic risks that we’re all trying to manage all the time: love, safety, and belonging. [59:35]
  • Tools, books, and approaches Jerry has found helpful for people who have difficulty saying “No” or establishing boundaries. [01:01:43]
  • “All beings own their own karma. Their happiness or unhappiness depend upon their actions, not my wishes for them.” [01:03:50]
  • A boundary tool that acknowledges compassion — but from a distance. [01:05:21]
  • To Jerry, the challenge isn’t in not having a tool for maximizing the efficiency with which we overcome our struggles. The challenge is in the meaning that gets put into a situation before a tool can even be applied. [01:06:35]
  • Like the Jerry of Seinfeld fame, we all have a Newman (or several) vexing our lives in some way. How might we humanely confront, converse with, or even sever ties with these unhealthy relationships? [01:07:21]
  • How does Jerry get someone from the point of intellectually agreeing with what he’s saying to actually putting it into practice and changing their behavior? [01:12:38]
  • As a 55-year-old who’s been journaling daily since he was 13, how does Jerry prescribe the practice as a way to drive personal results? [01:15:16]
  • Guilt vs. remorse. [01:17:30]
  • Marie Ponsot, the crow, and the importance of letting the crow speak in the journal. [01:18:14]
  • Jerry describes his typical bedtimes and mornings, when he fits in time for journaling, and what his journaling prompts and processes look like. [01:22:31]
  • How journaling can help us accept the totality of what’s going on in our lives by allowing our different voices to speak — the “multitudes” we contain per Walt Whitman’s Song of Myself. [01:26:13]
  • On Radical Acceptance by Tara Brach [01:28:19]
  • How Jerry has used Marvel’s Hulk and Thor to reconcile the different parts of himself and understand that they each serve a purpose — recalling Carl Jung’s notion of The Shadow. [01:29:20]
  • Jerry walks us through the time he made a difficult decision to say “No” — and focused on something narrowly — that ended up being life-changing in retrospect. [01:34:29]
  • Jerry’s advice to anyone who finds themselves in a similar position — or his younger self at this junction. [01:41:58]
  • How journaling, meditating, and answering certain questions has helped Jerry cope with rage-fueled anxiety and tame his inner Hulk. [01:44:01]
  • Where an aspiring beginner can learn more about loving kindness, aka metta meditation, and what it’s helped me discover about myself. [01:47:48]
  • What new behavior or belief has greatly improved Jerry’s quality of life? [01:50:16]
  • What would Jerry’s billboard say? [01:52:19]
  • Closing thoughts. [01:55:02]


The Tim Ferriss Show is one of the most popular podcasts in the world with more than 900 million downloads. It has been selected for "Best of Apple Podcasts" three times, it is often the #1 interview podcast across all of Apple Podcasts, and it's been ranked #1 out of 400,000+ podcasts on many occasions. To listen to any of the past episodes for free, check out this page.

Leave a Reply

Comment Rules: Remember what Fonzie was like? Cool. That’s how we’re gonna be — cool. Critical is fine, but if you’re rude, we’ll delete your stuff. Please do not put your URL in the comment text and please use your PERSONAL name or initials and not your business name, as the latter comes off like spam. Have fun and thanks for adding to the conversation! (Thanks to Brian Oberkirch for the inspiration.)

21 Replies to “Jerry Colonna — The Coach with the Spider Tattoo (#373)”

  1. Another timely episode, thank you both. Thanks Tim for your vulnerability and willingness to explore your personal challenges on the podcast. The examples really help me understand how to actually apply these ideas, not to mention understand them in the first place. I relate to that sense of overwhelm and struggling to say no to a quite few Newman’s 😅

    Curious to learn more about mythological origins of Iktomi, the trickster spider Tim mentioned – particularly its trickster aspect.

  2. I went to junior high in Brooklyn with Jerry (St Simon & Jude), he was a smart kid. Not surprised to see him successful here….

  3. Thanks jmes for this insightful reply, it helped me in letting me know what to expect in the podcast. As a result, I’m definitely going to listen to it.

  4. Tim, wow about having an option for 5$ per month blog support too? I’m already supporting with 10$ (though to be honest the value I get from your podcasts is definitely higher), but I know many people in my country (Poland), who are big fans, but don’t earn more than 500 USD per month, so 5$ would still be in the books, while 10$ would already exceed their financial possibilities.

  5. Dang, this is soooooooo valuable. Thank you Jerry Colonna for your gifts “shared.” Thank you Tim Ferriss for continuing to knock me out with the most incredible people who, through their experience, stimulates the “good stuff” around me and in me.

  6. I really like the quote “And just because you feel like shit doesn’t mean you are shit.” It’s a good reminder during those down times we all experience.

  7. Hey Tim, thanks for sharing another beautiful interview (I just discovered “you”.. – spent a night deeply moved by your interview with amanda palmer latterly)

    – one the points that stuck to my mind here was how jerry said, that many people (especially the sucessful) feel to be a fraud – and are frightened “to get caught”. for me that feels like an explanation for so much in the business world – and fascinatingly opens up my heart..

  8. “The biggest war you ever go through is right between your own ears”, says former Navy Seal and elite athlete David Goggins.

    Tim, thank you for sharing some of your battles, here and previously. On that note, I particularly enjoyed the huge level of mutual respect towards the end of the interview and specifically Mr Collona praising you and thanking you for your willingness to reveal your own struggles.

    You are not alone, would be one of Mr Collona’s billboard messages. Great choice and one which I think ties in very well with many of the ideas discussed in the conversation. I recently participated in an endurance event and one of the participants was wearing a shirt with a similar message on the back (You will never run alone). It was certainly uplifting to see that message and remember it during the race when the going got tough, that is, it reinforced the idea that, although I was in pain, most everyone else probably was too.

    Best wishes.

  9. Another superb deep dive into Tim through the lens of his guest. I have finally acted on getting Radical Acceptance only to find two versions. Tim, is it the Buddha version or healing shame that helped you through your challenge? I’m sure both are winners but I would like to begin with the one you found helpful. Thanks.

  10. Favorite quote that resonated with me: How have I been complicit in creating the conditions I say I don’t want?

  11. Hi Tim! Off topic but I cannot seem to find an answer. I just recently bought The 4-Hour Work Week book.

    There are multiple resources mentioned in the book that point to website, such as “Sample e-mail responses for fulfillment purposes” or “Sample GTC and order forms”. The website apparently does not exist anymore. Also The PX Method sales template website is no longer active. I would like to kindly ask other readers if there is a way to find all of these resources somewhere. Thanks a lot.

    1. Hi. Some information is no longer online, but some of what you’re looking for may be found in the 4-Hour Work Week Tools post: There may be a few broken links that we’re not able to repair at this time. You can also enter search terms into the search field at the top, right of the blog, such as “autoresponders.”


  12. “The Book Of Awakening by Mark Nepo has been a wonderful companion to my daily practice of waking up to myself. Great as a quick journal promotor too!

    Thanks for your wisdom Jerry. As a professional coach in my early years I found it very valuable.

    1. The Book of Awakening by Mark Nepo was and continues to be a moving piece and entrance into the “real” for me. Thank you for acknowledging this book. And Jerry you rock.

  13. Dear Tim: I am new to your content, but am so very impressed with your interview style and guest quality. I feel I have found hope and vision from you and your clients for my business and my 55 employees. I will make a few adjustments to a tight budget… but I will be a monthly patron/sponsor to help support and reimburse for this amazing show. Thank you Sir.

  14. Hi, Tim. My name is Isadora and I was reading your book in Brazil. Thanks for the valuable lessons. I have just decided not to finish it because I think I captured the essence and decided to do something different now.

    Somehow I think this is exactly what you would do.

    So, here is a question I would like to ask. If you could talk to anyone in this planet, who would you contact and why?

    I’m sorry if there is any grammar mistake, my English is a little rusty. Maybe I should start talking to some American people to improve my vocabulary and grammar.

  15. just wow, I’m only half way through and I’ve already ordered the 3 books recommended. Fascinating story! so open and vulnerable

  16. Meaty questions here-in. Being complicit to the aspects of our lives around which we will most complain is a mighty right hook of “own it”. Per Jerry’s phrasing, “How have i been complicit in creating the conditions I say I don’t want?”

    The episode pairs nicely with listening recently to Sam Harris interview with Jocko Willink: the arch-guru of owning it.

    I loved too the three powerful questions that followed, which any morning journaler will appreciate: “What am I not saying that needs to be said? What am I saying that’s not being heard? What’s being said that I’m not hearing?”.

    Jerry’s insightful moment to walk out on finance, recognizing it was his past but not his future, was beautifully shared.

    1. Oh…I meant to add the quote of the episode…Jerry saying “My soul said, listen motherfucker, you better sit down and pay attention to your life, because the stakes are too high…”, to which replied, “I think I read that in the Bhagavad Gita, Brooklyn edition?”.

  17. Hi Tim! Could you please paraphrase this question for me “How am I complicit in creating the conditions I say I don’t want?” I am not a native English speaker and would like to understand exactly what it means to apply in my life. Thank you!