Insurance Leadership Podcast

What if the key to financial freedom isn’t just about earning more—but preparing for the moment you won’t love your job anymore?

In this episode, host Casey Combest sits down with Sam Dogen, better known as the Financial Samurai, to talk about his new book Millionaire Milestones: Simple Steps to Seven Figures. Sam shares practical strategies on forecasting your misery, managing inconsistent income, celebrating wins without losing focus, and investing with perspective in uncertain markets.

Whether you’re a sales professional juggling commission, a leader steering a team through change, or someone planning for long-term independence, this conversation is packed with lessons to help you build wealth and lead with confidence.

In this episode, Ben Markland sits down with Terry Ward, Senior VP of Sales at United Vision Plan, live from the ICMG Conference in Tampa, Florida. With over 40 years of experience in the vision benefits industry, Terry shares his journey and how technology, consumer expectations, and transparency are reshaping the way benefits are delivered. From the evolution of vision care to the rise of digital platforms, Terry offers a fresh perspective on leadership, adaptability, and meeting today’s industry challenges head-on.

In this episode, Ben Markland talks with Dustin Moseley, Head of Distribution & Partnerships at Guardian Life, about his journey from entrepreneurship to the insurance industry. Dustin shares insights on building strategic partnerships, trends in the gig economy, and opportunities in the retiree market. He also discusses the importance of perseverance, staying informed, and how to navigate today’s evolving insurance landscape. Tune in for valuable advice and industry insights.

What happens when someone with firsthand experience in both clinical chaos and corporate healthcare decides to challenge the status quo? In this episode of the Insurance Leadership Podcast, host Ryan Eaton sits down with Tiffany Rider—health policy expert, NFL cheerleader alum, ER clinician, and founder of 20+ ventures—to explore her unconventional journey from rural Louisiana to national healthcare reform advocate. Tiffany opens up about the defining moments that shaped her mission to empower patients, expose inefficiencies in the system, and bring transparency to the broker-employer relationship. From misaligned incentives to the promise of direct primary care, this conversation is a must-listen for brokers, business leaders, and anyone seeking practical ways to drive real change in healthcare.

Welcome back to the Insurance Leadership Podcast!

Chris Ellis, CEO and Founder of Thatch, joins co-host Ben Markland for a powerful conversation recorded live at the ICMI Conference in Tampa. From his early days in cancer research at MIT to launching a company built to empower brokers, Chris shares how a deep understanding of healthcare and a passion for solving real problems led him to create one of the most promising platforms in the benefits space.

Welcome back to the Insurance Leadership Podcast!

Alisha Pequeno, Head of Distribution and Broker Partnerships at Zurich North America, joins co-host Ben Markland to share leadership lessons from the carrier side. She discusses building strong partnerships, leading with authenticity, and creating a culture that drives growth. Tune in for practical insights to help you lead, adapt, and build lasting success.

Welcome back to the Insurance Leadership Podcast!

What happens when the uniform comes off—but the mission isn’t over?

Army veteran and entrepreneur Adam Peters joins co-host Casey Combest to talk life after service, rebuilding identity, and leading with authenticity. From combat zones to boardrooms, Adam shares how discipline, vulnerability, and purpose helped him launch Stronghold—a thriving community supporting veterans in transition.

This episode is packed with leadership insights for anyone navigating change, redefining success, or learning to lead from who they truly are.

Welcome back to the Insurance Leadership Podcast! In this engaging episode of the Insurance Leadership Podcast, co-host Ben Markland welcomes Warren Laird, a seasoned leader in the insurance and vision care industry. With nearly three decades at VSP Vision Care, Warren shares invaluable insights on leadership, company loyalty, and fostering a workplace culture that stands the test of time. We explore the key lessons he’s learned throughout his career and how they apply to today’s ever-evolving business landscape.

Welcome back to the Insurance Leadership Podcast! In this episode, Co-host Casey Combest opens today’s episode with Luke Aslesen, Founder of INFRMD, a leader in revolutionizing how employees engage with their benefits. Luke shares his fresh approach to simplifying complex insurance concepts and discusses innovative programs like Benefits Boot Camp, designed to transform employee education in the industry.