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

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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