Key Takeaways
- The world's best investors are obsessed with not losing money and looking for asymmetrical risk/reward opportunities where they can risk a little for potentially huge upside. They also know they will be wrong sometimes, so they set up systems to still succeed even when wrong.
- Difficult but important decisions like leaving a successful career path often take years to finally act on, with a combination of relief and terror felt when taking the leap into the unknown. Having support from mentors, teachers and ancestors who have made similar journeys can provide reassurance.
- Journaling is a powerful tool for processing feelings, recognizing patterns, and giving voice to different parts of yourself without judgment. A simple prompt like "Right now I'm feeling..." can unlock important insights.
- Radically accepting all parts of yourself, even the ones you've disowned or that seem unacceptable, is an important step in healing and growth. Those parts often developed to protect you or help you survive.
- A transformative belief is accepting that you are fundamentally good and doing the best you can, even when you fail or make mistakes. Extending this compassion and forgiveness to yourself can ripple out to how you treat others.
Introduction
In this special episode, Tim Ferriss shares segments from two of his favorite interviews over the past decade of his podcast. Featured are entrepreneur and life strategist Tony Robbins ("Tony Robbins on Morning Routines, Peak Performance, and Mastering Money") and executive coach Jerry Colonna ("Jerry Colonna — The Coach with the Spider Tattoo").
Topics Discussed
Tony Robbins on Investing & Peak Performance (6:03)
- Tony's daily routines to strengthen his nervous system, including cryotherapy and priming (an alternative to traditional meditation)
- What the world's best investors have in common:
- Obsession with not losing money
- Focus on asymmetrical risk/reward (risking little for potentially huge upside)
- Knowing they'll be wrong and setting up systems to still succeed
- Lifelong learning and passion for giving back
Jerry Colonna & The Spider Tattoo (24:21)
- Jerry shares the story behind the spider tattoo on his chest, which originated from a powerful vision quest experience and dream
- The spider's message was to worry less and trust that his children would be ok - a message Jerry returns to when he forgets
Hitting Rock Bottom & Therapy (30:03)
- Jerry recounts a pivotal moment in February 2002 after an Olympic bid meeting near ground zero, where he almost jumped in front of a subway but called his therapist instead
- He discusses a suicide attempt at age 18 that led to 3 months in a psychiatric hospital (35:47)
- Jerry's therapist asked him 3 key questions that helped him rebuild his life:
- 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?
How Jerry Found His Way to Coaching (44:55)
- While sharing office space with his former business partners, a young lawyer came to Jerry for networking advice
- When asked why he became a lawyer, the man started crying, sharing he did it to please his father despite being miserable
- Jerry gave him the book "Let Your Life Speak" by Parker Palmer, and in that moment realized he needed to become a coach to relieve others' suffering in a similar way the book helped him
Working with High Achievers Who Feel Overwhelmed (51:15)
- High achievers are often driven by a sense of "not enough" and use busyness to distract from inner pain or emptiness
- Jerry asks them "How is being busy serving you?" to unpack the underlying needs driving overwork and burnout
- He also has them consider what they want for their own children - if something different than their current experience, it's a sign to re-evaluate
Tim & Jerry Discuss Boundaries and Saying No (1:04:13)
- Tim opens up about his challenge in saying no, with over 600,000 unanswered emails, many from people wanting favors
- His fear is disappointing people who have supported him, with some evidence of vindictive reactions to being ignored
- Jerry reflects this is a common fear of losing belonging and advises seeing the request behind the request - the person's pain
- He shares tools like "I wish I could but I can't", remembering you're not responsible for others' feelings, and loving detractors from afar
Reconciling Different Parts of Yourself (1:15:14)
- Jerry discusses his own anger and rage issues growing up, which he transformed from unhealthy Hulk to helpful Thor
- Accepting disowned parts of yourself, positive and negative, is critical to healing - those parts are often trying to protect you
- Journaling is a powerful way to give voice to different inner parts and lessen their power when not repressed
Making Difficult Decisions & Leaving Venture Capital (1:37:00)
- Jerry's most consequential decision was leaving a successful venture capital career, which took years of pain to finally act on
- He felt a combination of relief and terror after quitting, a common experience of the "midlife crisis" many face around age 40
- Reading "Let Your Life Speak", going on retreats, and support from mentors helped give him courage to leap into the unknown
Working with Anxiety & Worry (2:18:25)
- For Jerry, speaking his truth, in safe relationships and in journaling, has been key to transforming rage and anxiety
- He asks his anxiety questions - "What's the threat? What am I afraid of? Have I heard this before?" - to engage the rational brain
- Loving-kindness (metta) meditation, for oneself and others, is also a powerful way to work with difficult emotions
Believing "I Am Enough" & Messages for the World (2:26:40)
- The most transformative belief for Jerry has been accepting he is fundamentally good, even when he fails - a daily practice
- If he could put a message on a billboard, it would be: "You're not alone. And just because you feel like s**t doesn't mean you are s**t."
- We all struggle and feel broken sometimes, but countless traditions teach our inherent okayness - it's part of the human journey
Conclusion
In this wide-ranging conversation between Tim Ferriss and Jerry Colonna, they explore topics like the patterns of successful investors, hitting rock bottom, therapy, difficult career transitions, taming anxiety, and learning radical self-acceptance. Jerry's journey from suicidal teenager to burned out venture capitalist to wise executive coach holds insights for anyone on the path of inner growth and outer success. His tools of therapeutic questioning, journaling, meditation, and compassion provide a blueprint for navigating life's ups and downs with more ease and less self-judgment. Ultimately, his message is one of hope - that we are never alone in our struggles, and that with support and practice, we can come home to the truth of our inherent goodness.