Million Dollar Coach: How To Be A Great Leader | 110

36 snips

Jan 8, 2026

In this engaging discussion, Dan Putt, co-founder of Reboot and leadership coach, delves into transformative leadership strategies. He introduces the inside-out coaching philosophy, emphasizing the importance of self-awareness and reframing challenges like imposter syndrome into privileges. Dan offers practical journaling tips for self-discovery and shares insights on managing conflict as a sign of care. Together with Nathan, they explore how curiosity can transform fear into effective leadership and the importance of aligning personal goals with leadership identity.

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INSIGHT

Coaching Is A Spectrum

Coaching sits on a spectrum from directive advice to therapy-like exploration of identity and mental models.
Dan Putt emphasizes understanding who a leader is before prescribing frameworks to drive owned outcomes.

INSIGHT

Problems Don’t Prove You’re Broken

Founders often hesitate to claim authority because they fear upsetting people or being wrong.
Dan says tying self-worth to problems reduces problem-solving capacity and treats problems as proof of failure.

ADVICE

Reframe Have-To Into Get-To

Reframe "have to" tasks as "get to" privileges to reduce resentment and increase perspective.
Use the reframing to remember many problems are signs of success and opportunity.

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Steering a company from nascent idea to multi-million dollar revenue is rarely a smooth ride. Often, it's a journey fraught with uncertainty, tough decisions, and the internal battles no one sees. For Nathan, the guiding hand through much of this journey has been his coach, Dan Putt. As a co-founder of Reboot, Dan has spent years working with leaders and executives, helping them navigate growth without losing themselves in the process. In this episode, Dan shares not only his unique coaching philosophy - which emphasizes a deep, inside-out understanding of oneself, but also practical tools and frameworks that address common founder sticking points like imposter syndrome, the fear of conflict, and the allure of the "magic bullet" solution. Get ready to rethink your approach to leadership and personal development.

Timestamps:
00:00 Introduction
02:23 Dan's coaching philosophy
04:36 The Greek God CEO and imposter syndrome
07:11 The "have to" versus "get to" reframe
10:00 What problems say about identity
12:56 Listening to understand: Beyond the words
15:46 Inside-out leadership development
18:31 The challenge of competitive responses
21:52 Journaling for self-discovery
25:21 Practical tips for consistent journaling
28:11 Getting clear on what you truly want
30:26 The "loyal soldier" concept
33:53 How personal traits drive ambition
38:39 The shift from "need" to "want"
41:43 Conflict as progress and care
45:34 Tools for navigating conflict
50:47 The "net" framework for communication
52:23 Avoiding problems vs. facing them
55:29 The temptation of the "magic bullet"
59:08 Feeling the fear without dwelling
1:01:21 The tantruming toddler metaphor for anxiety
1:03:00 Leading with curiosity, not fear

If you enjoyed this episode, please like and subscribe, share it with your friends, and leave a review. I read every single one.

Learn more about the podcast: https://nathanbarry.com/show

Follow Nathan:
Instagram: https://www.instagram.com/nathanbarry
LinkedIn: https://www.linkedin.com/in/nathanbarry
X: https://twitter.com/nathanbarry
YouTube: https://www.youtube.com/@thenathanbarryshow
Website: https://nathanbarry.com
Kit: https://kit.com

Follow Dan:
Website: https://danputt.com
LinkedIn: https://www.linkedin.com/in/danputt
X: https://twitter.com/danputt
Company Website: https://reboot.io

Featured in this episode:
Kit: https://www.kit.com
Reboot.io: https://reboot.io
The Artist's Way by Julia Cameron: https://juliacameronlive.com/books/the-artists-way
750words.com: https://750words.com
The Obstacle Is the Way by Ryan Holiday: https://ryanholiday.com/books/the-obstacle-is-the-way
Extreme Ownership by Jocko Willink: https://echelonfront.com/Extreme-Ownership

Highlights:
02:47 Understanding the spectrum of coaching approaches
08:24 The danger of linking self-worth to problems
13:44 The wisdom found at the emotional level
23:25 The clarifying power of daily journaling
34:05 How the "loyal soldier" shapes our drives
45:51 Why true care often requires conflict
53:49 Facing uncomfortable feelings builds resilience
1:01:05 Approaching anxiety like a tantruming child
1:03:54 Shifting from fear to wonder for better leadership