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Wine Down with Kev is a weekly podcast hosted by Kevin Spann, the Insurance Guru. Tune in to hear exclusive interviews with community leaders, business owners, and more.
Wine Down with Kev is a weekly podcast hosted by Kevin Spann, the Insurance Guru. Tune in to hear exclusive interviews with community leaders, business owners, and more.
Episodes
Wednesday Dec 24, 2025
Wine Down With Kev: 50 Agents In 50 States Episode 47 Heidi Rowan
Wednesday Dec 24, 2025
Wednesday Dec 24, 2025
In this episode of Wine Down With Kev, Kevin travels to Happy Valley, Oregon, to sit down with Heidi Rowan, an Allstate agency owner who’s built her business on trust, education, and long-term relationships.
Heidi shares how serving a growing community like Happy Valley requires more than quoting policies — it requires understanding lifestyles, budgets, and life stages. From helping first-time homeowners to guiding families through evolving insurance needs, Heidi’s approach centers on clarity, confidence, and care.
Grab a glass and join us as we dive into this inspiring story of resilience, dedication, and success. Don’t miss this episode!
Wednesday Dec 24, 2025
Wine Down With Kev: 50 Agents In 50 States Episode 46 Carley Pickern
Wednesday Dec 24, 2025
Wednesday Dec 24, 2025
In this episode of Wine Down With Kev, Kevin heads to Grass Valley, California, to sit down with Carly Pickern, Allstate agency owner who’s built her business around education, trust, and genuine local connection.
Kevin and Carly talk about the importance of being present in your community, staying flexible as life changes, and why local agents still matter in a world full of 1-800 numbers and online quotes.
Grab a glass and join us as we dive into this inspiring story of resilience, dedication, and success. Don’t miss this episode!
Wednesday Dec 10, 2025
Wine Down With Kev: 50 Agents In 50 States Episode 45 Malia Rogers
Wednesday Dec 10, 2025
Wednesday Dec 10, 2025
In this episode of Wine Down With Kev, Kevin sits down with Malia Rogers — first-generation American, founder of MediGap Pros LLC, author, speaker, and master networker whose work is changing how independent agents build relationships and grow their business.
Malia’s story is a masterclass in turning identity, grit, and values into a business that doesn’t just survive — it thrives. Tune in to learn how connection, not just commission, can become your greatest asset.
Grab a glass and join us as we dive into this inspiring story of resilience, dedication, and success. Don’t miss this episode!
Wednesday Dec 03, 2025
Wine Down With Kev: 50 Agents In 50 States Episode 44 Zachary Vaswani
Wednesday Dec 03, 2025
Wednesday Dec 03, 2025
In this episode of Wine Down With Kev, Kevin sits down with Zachary Vaswani, agency owner at Allstate in Norwood, Massachusetts — a professional who’s built his business around relationships, responsiveness, and community trust.
Zach opens up about why “being local” still matters, how he treats customers like neighbors instead of policy numbers, and why good coverage starts with real conversations. He walks through how he helps residents get the right auto, home, life, or business protection — not as a sale, but as a service.
Grab a glass and join us as we dive into this inspiring story of resilience, dedication, and success. Don’t miss this episode!
Tuesday Nov 25, 2025
Wine Down With Kev: 50 Agents In 50 States Episode 43 Monica Titley
Tuesday Nov 25, 2025
Tuesday Nov 25, 2025
In this loud, loving, and straight-shooting episode of Wine Down With Kev, Kevin travels to Huron, Ohio, to sit down with Monica Titley — a powerhouse agency owner who built her business from the ground up with grit, humor, and heart.
Monica’s story is a masterclass in resilience and realness. From starting over at 30 with only fifty cents in her pocket to running multiple thriving offices across northeast Ohio, she’s proof that hustle and heart can coexist. Her team culture? Loud music, open honesty, and heels optional.
Grab a glass and join us as we dive into this inspiring story of resilience, dedication, and success. Don’t miss this episode!
Wednesday Nov 19, 2025
Wine Down With Kev: 50 Agents In 50 States Episode 42 Justin Harkelroad
Wednesday Nov 19, 2025
Wednesday Nov 19, 2025
In this powerful and faith-driven episode of Wine Down With Kev, Kevin heads to Gainesville, Georgia, to meet Justin Harkelroad — a fourth-generation insurance agency owner redefining what it means to build a business rooted in purpose.
Justin opens up about the values that shape his agency: faith, stewardship, and serving only those he’s called to protect. From a client’s devastating fire that tested everything to his team’s weekly staff devotions, he shares how faith and integrity remain the foundation of his success.
You’ll hear how Justin transitioned from cold calls to a thriving referral-based agency, how he leads with prayer and precision, and why sometimes the best business move is saying “no” when the fit isn’t right.
Grab a glass and join us as we dive into this inspiring story of resilience, dedication, and success. Don’t miss this episode!
Wednesday Nov 12, 2025
Wine Down With Kev: 50 Agents In 50 States Episode 41 Jalene Berger
Wednesday Nov 12, 2025
Wednesday Nov 12, 2025
In this week’s episode of Wine Down With Kev, Kevin travels to Kansas to meet Jalene Berger, agency owner and leader of The Berger Agency, a powerhouse team known for its customer-first service, community involvement, and commitment to doing insurance differently.
Jalene shares how she built her agency from the ground up — focusing on education, empowerment, and empathy. From helping Kansas families understand their coverage to mentoring her team to lead with confidence, Jalene proves that great leadership starts with genuine care.
Grab a glass and join us as we dive into this inspiring story of resilience, dedication, and success. Don’t miss this episode!
Wednesday Nov 05, 2025
Wine Down With Kev: 50 Agents In 50 States Episode 40 Shawn Reeves
Wednesday Nov 05, 2025
Wednesday Nov 05, 2025
In this insightful episode of Wine Down With Kev, Kevin sits down with Shawn Reeves, an Allstate agency owner from Oklahoma who’s built his business on two simple principles — work hard and care deeply.
Shawn shares his story of perseverance, community connection, and what it takes to grow a successful agency in today’s changing insurance landscape. From navigating Oklahoma’s unpredictable weather patterns to helping local families protect their homes, cars, and businesses, Shawn’s focus has always been on relationships over transactions.
Grab a glass and join us as we dive into this inspiring story of resilience, dedication, and success. Don’t miss this episode!
Wednesday Oct 29, 2025
Wine Down With Kev: 50 Agents In 50 States Episode 39 Andrea Early
Wednesday Oct 29, 2025
Wednesday Oct 29, 2025
In this uplifting episode of Wine Down With Kev, Kevin travels to O’Fallon, Missouri, to meet Andrea Early, agency owner of Early Edge Insurance and a proud Allstate partner known for her heart-centered approach to protection.
Andrea shares how she’s built her business around one guiding belief — people come first. From helping O’Fallon families find coverage that fits their lives and budgets, to reviewing policies as life changes, Andrea’s focus is on understanding each client’s goals and giving them the confidence to plan ahead.
Grab a glass and join us as we dive into this inspiring story of resilience, dedication, and success. Don’t miss this episode!
Wednesday Oct 22, 2025
Wine Down With Kev: 50 Agents In 50 States Episode 38 Jeremy Radabaugh
Wednesday Oct 22, 2025
Wednesday Oct 22, 2025
In this grounded and genuine episode of Wine Down With Kev, Kevin travels to Martinsburg, West Virginia, to sit down with Jeremy Radabaugh, a community-driven Allstate agency owner who believes real success comes from relationships — not just results.
Jeremy shares how being born and raised in West Virginia shaped his approach to business, service, and family. He’s built his agency around one mission: helping local families protect what matters most while preparing for what’s next.
Whether he’s reviewing policies for a longtime client or helping a first-time homeowner navigate coverage, Jeremy’s leadership style reflects the best of small-town values and big-picture vision.
Grab a glass and join us as we dive into this inspiring story of resilience, dedication, and success. Don’t miss this episode!
