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The Digital Insurance Agent

The Digital Insurance Agent is a podcast that explores the latest trends, tools, and strategies for transforming your insurance agency in the digital age.

Join host Carl Willis, a seasoned financial services digital marketing consultant, as he interviews industry experts, shares success stories, and provides actionable tips to help you stay ahead of the curve and build a successful and sustainable insurance agency in today's ever-evolving market.

Whether you're a seasoned pro or just starting out, this show is the ultimate guide to help you modernize your insurance agency and thrive in the digital world.

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The Digital Insurance Agent

From Law School to 7-Figure Entrepreneur: Bart Henderson on Freedom, Systems & Scalable Businesses

August 15, 2025 • Carl Willis - Agent Branding & Marketing

In this episode of the Digital Insurance Agent Podcast, host Carl Willis interviews Barton Henderson, Esq.—a licensed attorney turned serial entrepreneur. Discover how Bart went from law school side hustles to building a 7-figure business that landed on the Inc. 5000 list.

You'll learn how Bart leveraged systems, minimized overhead, and avoided “headache businesses” by embracing automation, partnerships, and culture-driven leadership. He also shares insights on:

Avoiding burnout with mindset shifts
Building systems without losing momentum
When to delegate (even if you're the best at it)
Creating a culture of honesty, accountability & trust
Scaling with freedom in mind
Legal & operational risk management for entrepreneurs

Whether you're an insurance agent, agency owner, or service-based entrepreneur, this episode is packed with practical strategies to help you grow a business that doesn't own you.

📌 Connect with Bart:
👉 Instagram: @barthendersonesq
👉 Website: www.barthenderson.com
👉 Agora Guild (30-Day Free Trial): www.agoraguild.com

🎧 Subscribe for more real-world insights from digital-first entrepreneurs.
#Entrepreneurship #BartHenderson #InsuranceAgents #BusinessGrowth #DigitalMarketing #SmallBusinessTips #AgoraGuild #FreedomBusiness

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