Wine Down with Kev

In this episode of Wine Down With Kev, Kevin sits down with Kristin Kasel and Jeremy Olson, the duo behind Insurance Role Play, a training platform built to sharpen sales skills, boost confidence, and help agents win real conversations — not just memorize scripts.

Kristin and Jeremy share why role play is still one of the most underused (and misunderstood) tools in insurance sales. They break down how consistent practice builds con...

In this episode of Wine Down With Kev, Kevin sits down with Cole Caughern, an insurance professional and leader known for his thoughtful approach to growth, leadership, and long-term thinking in the industry.

Kevin and Cole talk about mindset, personal growth, and why success in insurance (and business) comes down to consistency, integrity, and surrounding yourself with the right people.

Grab a glass and join us as we dive into thi...

For the milestone Episode 50 of Wine Down With Kev, Kevin heads to Livonia, Michigan, to sit down with Cheryl Bowker, an Allstate agency owner whose career has been defined by experience, education, and genuine care for the people she serves.

Cheryl shares how building a successful agency starts with listening. From helping Michigan families protect their homes and vehicles to guiding them through long-term life changes, her approa...

In this episode of Wine Down With Kev, Kevin heads to Bangor, Maine, to sit down with Steve and Janet Wilde, a husband-and-wife duo who have built a trusted Allstate agency rooted in partnership, consistency, and community care.

Steve and Janet share what it’s like to run a business together while serving generations of Maine families. From helping clients navigate home, auto, and life protection to guiding them through changing se...

In this episode of Wine Down With Kev, Kevin heads to Stamford, Connecticut, to sit down with Daniela Mercado, an Allstate agency owner who’s built her business on education, accessibility, and strong community relationships.

Daniela shares how serving a diverse, fast-moving area like Stamford requires more than quoting policies — it requires listening, clarity, and the ability to meet people where they are. From helping families p...

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...

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 u...

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 ...

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 res...

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 hu...

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 weekl...

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 men...

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...

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,...

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...

In this powerhouse episode, Kevin heads to Nevada to meet Melissa Hudson, an Allstate agency owner whose career is defined by excellence, education, and impact.

With two master’s degrees, a wall full of Allstate’s top awards, and a heart for community service, Melissa has mastered what it means to lead with both intelligence and compassion. She’s built a high-performing agency that thrives on customer relationships, mentorship, and...

In this inspiring episode of Wine Down With Kev, we travel to Parker, Colorado, to meet Jennifer Mathews — Allstate agency owner and community leader.

Jennifer’s story starts with a friendly bet that changed everything. What began as a dare to try insurance turned into her life’s calling — and over the next decade, she built an $18 million agency from the ground up.

Grab a glass and join us as we dive into this inspiring story of r...

In this empowering episode, Kevin heads to Greenville, North Carolina, to meet Kelly Spicer, Allstate agency owner and founder of Spicer Financial Group. Kelly has built her agency on one belief: insurance is personal.

From protecting families with life, home, and retirement planning to guiding clients through income protection and legacy building, Kelly’s approach is grounded in relationships and thoughtful guidance.

Grab a glass ...

In this deeply inspiring conversation, Kevin heads to Great Falls, Montana, to meet Tammy Quintrell Stubbs — an Allstate agency owner who went from being a 21-year-old single mom with no experience to a 25-year veteran with two thriving offices, a powerful team, and a heart rooted in service.

Tammy opens up about her unlikely start in insurance, the grit it took to build her business, and why local leade...