Leadership Unlocked: The Operating System Every Executive Leader Needs to Delegate Effectively & Foster Accountability So You Can Stop Managing Alone and Start Leading a Team Again 8-Figure CFO on Why Chasing Perfection Leads to Failure | Jon Blair - E17
Dusty is joined by Jon Blair—heavy metal guitarist turned purpose-driven entrepreneur and founding executive at Guardian Bikes—for a conversation on how clarity beats chaos in both business and life. Jon shares his unconventional journey from touring musician to scaling a startup from zero to eight figures, raising $15 million, and ultimately launching Free to Grow CFO to help D2C brands build smart, scalable finance operations. They unpack the lessons of navigating multiple “startups” at once—including business, family, and personal growth—while embracing imperfection, focusing on the few things that truly move the needle, and leading with intentionality. Jon reflects on the influence of faith, the discipline of planning, and the power of defining your role so you can operate in your unique strengths. Along the way, he offers practical wisdom on seasons of life, parenting with purpose, and finding joy in the journey rather than the end goal. This episode is a masterclass in balancing ambition with presence, and in building something meaningful without losing sight of what matters most.
Key Timestamps:
(00:00) - Meet Jon Blair: From Heavy Metal to CFO
(05:44) - Balancing Music and Business
(08:46) - Navigating Leadership and Family Life
(17:49) - Advice for Aspiring Entrepreneurs
(23:57) - Implementing Weekly and Quarterly Planning
(25:28) - Embracing Imperfection in Leadership
(32:17) - Teaching Principles to Children
(39:23) - Rapid Fire Leadership Insights
Key Topics Discussed:
Leadership Unlocked, Leadership Insights, Dusty Holcomb, Servant Leadership Principles, Self-Leadership Strategies, Growth Mindset in Leadership, Integrity and Leadership, Leadership Development Resources, Effective Leadership Habits, Empowering Leadership Techniques, Senior Executive Insights, Leadership Quotes and Reflections, Leadership Podcast, Executive Coaching, CEO Podcast, Business Leadership, Leadership Growth, Leadership Journey, Stories From Leaders, Leadership Tools, High-Performing Teams, Leadership Mindset, Decision Making, Personal Growth, Leadership Coaching, Organizational Leadership
Mentions:
Website: https://freetogrowcfo.com/
LinkedIn:
Mentions:
The War of Art: Break Through the Blocks and Win Your Inner Creative Battles by Steven Pressfield
Traction: Get a Grip on Your Business by Gino Wickman
The 7 Habits of Highly Effective People by Stephen Covey
More of Leadership Unlocked:
Check out our leadership development resources at https://arcqusgroup.com/
Contact me at dusty@arcqusgroup.com