“True leadership isn’t about doing it all yourself. It’s about helping others rise to the occasion.”

In this episode, Craig P. Anderson talks to Brian Wheeler, the President and Chief Visionary Officer of The Vertical Life, for an insightful conversation about leadership. Brian shares his leadership journey, from high school entrepreneurship to leading a faith-based nonprofit organization focused on developing young leaders. Brian’s story is a testament to the power of vision, humility, and influence in leadership. Brian reflects on key moments of his leadership evolution, including the lessons he learned as a teenager running a pressure washing business, and the ongoing work of leading with purpose in a mission-driven organization. He emphasizes the importance of self-discovery for young leaders and how developing a mindset of service, rather than self-centered ambition, has been crucial to his leadership style.

After You Listen:

• Connect with Brian Wheeler on LinkedIn

• Check out The Vertical Life

• Connect with Craig on LinkedIn

• Subscribe to Craig’s "The Evolving Leader" newsletter

Key Takeaways:

• Leadership is about influence, not age, authority, or title

• Humility as a leader leads to better collaboration and growth

• Faith in your mission fuels motivation and commitment in your team

Things to listen for:

(00:00) Intro

(00:30) The importance of vision in leadership

(01:33) Brian’s leadership insights

(07:12) Brian’s early leadership journey

(11:24) Leadership in faith-based organizations

(16:36) The role of humility in leadership

“Leadership starts with clarity—and the courage to act on it.”

In this episode, Craig Anderson takes the mic solo to share the three leadership mistakes he sees time and again: outsourcing your vision, waiting for certainty, and over-indexing on empathy. Drawing from decades of experience and recent coaching conversations, Craig reflects on why leaders must stop looking for consensus and start setting direction. He opens up about times he made the wrong call, how he course-corrected, and why taking imperfect action is better than standing still. Craig also unpacks how empathy without accountability can stall a team—and what it really looks like to lead with both compassion and conviction.

Whether you're navigating your first strategic plan or struggling to have hard conversations, Craig’s insights will help you evolve with confidence and purpose.

After You Listen:

• Connect with Craig on LinkedIn
• Subscribe to Craig’s "The Evolving Leader" newsletter
• Download Craig’s “10 Tips to Level Up Your Leadership” guide

Key Takeaways:

• Vision starts at the top—not in a group vote
• Leaders grow by acting, adjusting, and learning
• Empathy means being honest, not avoiding discomfort

Things to listen for:
(00:00) Intro
(01:18) Stop crowdsourcing your vision
(02:38) The cost of indecision
(05:44) A real story about making the wrong call
(08:52) When empathy becomes avoidance
(11:31) Building empathy into your leadership style
(12:41) How to hold high standards with kindness
(13:41) The most empathetic thing might be a hard truth
(14:38) A call to action for evolving leaders

“Leadership is about building others up while getting out of their way.”

In this episode, Craig Anderson talks with Peter Dunn, founder and CEO of Your Money Line, about what it really takes to grow into a leadership role. Pete shares candid reflections on how he went from a self-focused leader to someone committed to empowering others through trust, transparency, and support. He opens up about past missteps, the guilt he carries over early leadership choices, and the ongoing work of becoming someone worth following. Pete also explores why feedback is an act of care, how empathy and performance go hand in hand, and why the mission behind Your Money Line is so deeply personal. Whether you’re a new leader or a seasoned executive, Pete’s story is a reminder that leadership is less about having the answers—and more about asking the right questions.

After You Listen:

• Connect with Peter Dunn on LinkedIn

• Check out Your Money Line

• Connect with Craig on LinkedIn

• Subscribe to Craig’s "The Evolving Leader" newsletter

Key Takeaways:

• Feedback is an investment in someone’s growth

• Empathy makes hard conversations more effective

• Leadership is about helping others shine, not just hitting goals

Things to listen for:
(00:00) Intro
(01:11) Seeing leadership potential in others
(02:15) Pete’s book for HR leaders
(03:00) The difference between givers and takers in leadership
(04:06) What it means to truly empower your team
(05:39) Creating a coaching tree inside your business
(07:00) Pete’s leadership role model
(08:11) Learning from a strong executive team
(09:56) Valuing teammates’ career journeys
(11:22) Pete’s first leadership experiences
(13:25) Recognizing privilege and using it for good
(15:10) Identifying and developing high-potential team members
(17:11) Leadership lessons from unexpected places
(18:34) Telling the truth with empathy
(20:07) Leading with curiosity and compassion
(21:17) The impact of mission-driven leadership
(26:11) How culture reinforces the mission
(27:18) The advice Pete would give his younger self
(28:53) The role of self-awareness in leadership growth