In this Winning Through Culture episode, Rebekah Miller sits down with co-host Tim Flanagan for another “Ask Me Anything.” From childhood dreams of being a cowboy to leading The Pelora Group as a third-generation financial services veteran, Tim shares stories of hard work, self-awareness, and cultural impact. He opens up about the books, mentors, and philosophies that shaped him, offering young leaders practical wisdom for navigating today’s challenges with intention and grit.

This episode is a blend of nostalgia, humor, and actionable insights, revealing how Tim’s Colorado roots and family legacy fuel his drive to build thriving, people-first cultures. Whether you’re an aspiring leader or a seasoned pro, Tim’s journey underscores the power of showing up and inspiring others.

Key Takeaways:

• Childhood aspirations: From cowboy dreams to racing cars and beyond


• Early jobs and lessons in hard work, showing up, and relating to people


• Influential books like Managing Oneself and their impact on self-aware leadership


• The role of faith, family, and mentors in shaping a legacy-driven career


• Debunking the myth that leadership is easy—especially in today’s complex world

Related episodes to “Behind the Mic: Leadership Lessons and Life with Tim Flanagan”:  Behind the Mic: Amanda Kramer’s Journey, Values, and the Power of Vulnerability  |  Coaching Tomorrow’s Leaders: Confidence, Growth, and the Power of Mentorship

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Tune into Winning Through Culture on your preferred Podcast platform

About Winning Through Culture

In today’s ever-changing world, it is more important than ever for an entrepreneur to stay impactful and relevant.

That’s where Winning Through Culture comes in! This podcast will let you inside the dynamic minds of Tim Flanagan and Amanda Kramer to give you expertise, insight, and tips so that you can remain impactful and relevant.

With Tim and Amanda’s experience and desire to plant knowledge in the business leaders around them, we hope you will take this podcast into your everyday life as an upcoming entrepreneur.

This genuine content will provide opportunities, relationships, and a community to expand your personal and professional growth.

Let’s create a winning culture together!

Connect with Us

• Tim Flanagan: LinkedIn | Instagram


• Amanda Kramer: LinkedIn


• Rebekah Miller: LinkedIn

Important Links

• The Pelora Group

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