How to Protect Your Agency from a Lawsuit or Hack (Before It’s Too Late) With Draye Redfern | Ep #846

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What would happen if one client lawsuit, one hacked account, or one missed renewal completely wiped out your agency? Have you ever stopped to think about how exposed your business really is even if you’re “doing everything right”?

Today's featured guest started his career working in the insurance industry and eventually found a love for marketing. He talks about the side of agency life most people ignore: protecting what you’ve built, and breaks down how to safeguard your business with the right insurance, why every agency should have cyber liability coverage, and how a “give first” mindset has helped him land major clients like Daymond John, Chris Voss, and Dr. Benjamin Hardy.

Draye Redfern is a serial entrepreneur and the founder of Redfern Media and FractionalCMO. Over the past decade, he’s built and sold multiple companies, including a $40M insurance agency acquired by one of Warren Buffett’s Berkshire Hathaway subsidiaries. With 15 years in risk management and a passion for modern marketing, Draye now helps businesses scale smarter while protecting their downside.

In this episode, we’ll discuss:

• How “Growth Blindness” Can Hurt Your Business.

• The Hidden Risk Most Agencies Ignore.

• Why You Probably Need a Cyber Liability Insurance.

• How to Get Big Clients by being in the Right Rooms.

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The Unlikely Path From Insurance to Marketing

Draye grew up in a household where entrepreneurship was a way of life. His dad owned a business, and by age 12, Draye was doing the grunt work: filing papers, scanning documents, and learning what it really meant to keep a company running. He had a front-row seat to the chaos and grit of small business.

Over time, Draye realized he had a knack for marketing. His early ideas sometimes outperformed everyone else’s, and by his early 20s, he was leading the marketing division of a $28 million firm. Under his direction, they scaled past $40 million in annual revenue. That success led to the company’s eventual sale to none other than one of the Berkshire Hathaway companies.

Stop Being Growth Blind and Start Protecting the Downside

While most marketers are obsessed with lead flow and growth, Draye brings a completely different mindset to the table: protect the downside first. After spending 15 years insurance and the risk management world, he learned that too many businesses are “growth blind.” They’re chasing top-line numbers while leaving themselves totally exposed if something goes wrong.

For his part, Draye thinks about how to mitigate downside risks first and then, once he has that locked down, then he starts thinking about growth. Admittedly, it’s backwards from how most people do it, but it’s what