Are you an independent insurance agent or agency leader looking for a smarter way to grow your business, retain more profit, and better serve your clients? In this episode, host Brent Kelly sits down with Warren Cleveland, CEO of Captive Coalition, to uncover the untapped potential of captive insurance.

Warren shares his entrepreneurial journey from aviation to insurance innovation—and explains why captives are becoming essential tools for agents who want more control, transparency, and long-term client relationships. You'll learn how to overcome misconceptions, embrace failure as growth, and understand the real financial impact of captives on your agency’s future.

Highlights Include: 00:00 Introduction to Captives and Insurance Leadership04:12 Understanding Captives: What They Are and Why They Matter10:42 The Unique Approach of Captive Coalition19:39 Challenges and Misconceptions in the Captive Insurance Space25:02 Success Stories and Empowering Agents33:17 Advice for the Younger Self: Embracing Failure39:18 Final Thoughts and Resources for Agents

Whether you’ve never heard of captives or you’re ready to take the next step, this conversation will shift how you think about risk, revenue, and relevance in today’s insurance world.

To learn more about Warren Cleveland and Captive Coalition visit their site at https://www.captivecoalition.com/.

To learn more about our programs for growth-minded agencies visit www.sitkins.com.

Most insurance agency leaders focus on revenue, retention, and growth—but there’s one overlooked metric that could transform your agency’s future: Revenue Per Relationship.

In this episode, Brent Kelly breaks down why this powerful measurement matters more than ever and how it reveals the true value of your client connections. You’ll learn practical strategies to elevate client experiences, increase profitability, and create a culture of high performance and accountability.

If you're ready to break through growth plateaus, get more referrals, and lead your team with greater purpose and clarity, this episode is for you.

Discover:

• The #1 metric that drives long-term agency success

• How to deepen client relationships and grow without chasing more volume

• Why emotional intelligence is a business advantage

• How to shift from complacency to continuous improvement

Whether you’re an agency owner, sales leader, or producer, this episode will challenge the status quo—and equip you to grow smarter, not just bigger.

If you're ready to grow your agency, learn more about our programs at www.sitkins.com

Why not you? In this powerful solo episode, Brent Kelly challenges insurance agency leaders to confront the one thing holding them back: their mindset.

Drawing inspiration from the final chapter of Best Version Possible, Brent unpacks the core differences between good agencies and great ones. Discover the three areas where most agency leaders think too small—and how to break free from the self-limiting beliefs that keep your agency from growing.
02:00 – A Story from a Yacht and a Revelation
06:45 – Are You Thinking Too Small?
09:35 – Massive Action Beats Endless Planning
14:20 – Don’t Just Lead—Build Future Leaders

Whether you lead a small shop or a large, growing agency team, this is your reminder: You don’t need to be the smartest or most experienced—just bold enough to ask, “Why not me?”

If you're ready to stop playing small and start owning your potential, visit www.sitkins.com to learn about our programs, or order a copy of Best Version Possible.

What’s Holding Your Agency Back?

If you’re still managing people, profit, and performance the old way, you may be capping your agency’s potential without realizing it.

In the latest episode of The Agent Leader , Brent Kelly is joined by Roger Sitkins for an inspiring conversation about what it really takes to build a high-performance agency in today’s world.

🎧 Tune in to discover:

• The leadership mindset that drives organic growth

• How to gain freedom in your time, finances, and relationships

• What top-performing agencies do differently—and how to join them

• Real stories from the field that prove what’s possible with the right coaching and strategy

Whether you're a producer, agency leader, or aspiring rainmaker, this episode is packed with insights you can use right away.

To learn more about our programs and access free resources, visit www.sitkins.com/podcast

Renowned insurance technology expert Steve Anderson, co-founder of Catalyit and author of The Bezos Letters, joins us to explore how artificial intelligence is transforming the insurance industry. Drawing lessons from the internet boom of the late ’90s, Steve shares how today’s agencies can move from AI hype to real-world results.

You’ll discover how AI can boost efficiency, improve data quality, and free up your team to focus on high-value client relationships. We break down:

• How leading agencies are using AI to automate routine tasks
• Strategies to reallocate time toward nurturing top clients
• Why structured processes are the backbone of scalable growth
• Tips for managing change and closing skill gaps in your agency

If you want practical strategies to modernize your agency and leverage AI without losing the personal touch, this episode is for you.

To learn more about Steve Anderson and Calayit visit their site

To learn more about our programs for growth-minded leaders, visit www.sitkins.com

Is your agency stuck selling insurance as just another commodity? In this powerful episode, Brent Kelly reveals how to shift that perception through meaningful communication and client connection.

Learn how to differentiate your agency by going beyond the overused promises of "great service" and "experienced staff." We explore the "head, heart, and hands" framework with insights inspired by Kari Glennon—designed to help you connect with what your clients think, feel, and truly value.

Highlights include:

• (01:00) - Insurance Is Not a Commodity
• (09:58) - Building Connections Through Understanding Clients
• (14:40) - Mastering Communication Skills in Insurance
• (19:15) - Developing Critical Communication Skills
• (24:48) - Continuous Improvement in Insurance Communication
• (36:14) - Exclusive Partnership Opportunities in Insurance

You’ll discover how a consultative approach uncovers what really matters to business owners, turning conversations into conversions and transactions into trusted relationships.

We also share practical strategies for delivering compelling value statements, handling crucial conversations, and preparing through role-playing and low-risk practice—all rooted in Stephen Covey’s timeless principle: seek first to understand.

Whether you're a producer or agency leader, this episode will help elevate your communication, grow your impact, and unlock new levels of client loyalty.

To learn more about our programs for growth-minded insurance agencies, visit www.sitkins.com

Is your agency rowing in the same direction—or just spinning in circles?

In this episode, senior consultant Kari Glennon joins Brent Kelly to break down the real reasons insurance agencies struggle with internal misalignment—and what to do about it. From duplicated efforts to pricing uncertainty, Kari shares how a lack of formal communication and role clarity quietly erodes agency efficiency and culture.

Discover how to transform internal conflict into collaboration, align sales and service teams, and build a structure where every team member knows their role and impact. We explore practical tools like structured communication cadences, leadership-led retrospectives, and redefining how value is perceived across the agency—not just in production roles.

If you’re ready to stop the chaos and build an insurance agency that moves forward together with purpose, this episode is a must-listen.

🎧 What You’ll Learn:

• • (06:59) - The Power of Clear Alignment
  • (18:24) - Starting Point
  • (22:37) - Role Alignment in Agency Dynamics
  • (29:00) - Effective Strategies for Agency Alignment

  
  

  If you're ready for your agency to get aligned to achieve results, visit www.sitkins.com

Feeling pulled in every direction in your agency? In this episode, Brent Kelly shares how to flip daily distractions into your biggest productivity wins. Inspired by Cal Newport’s Deep Work and Darren Hardy’s Insane Productivity, Brent offers practical strategies for creating focus zones, setting boundaries, and aligning your work with what truly matters.

You’ll learn:

• How to identify and eliminate hidden productivity killers

• The power of “productive discomfort” and why growth isn’t always cozy

• How to use accountability and priorities to stay on track

Whether you lead an insurance agency or just want to do more meaningful work, this episode will help you reclaim your time and unlock your full potential.

Access tools to boost your agency's productivity now.