Toby Hedges on Building a Powerhouse Insurance Agency in Any Market — Growth Strategies (Part 1)

By Craig Pretzinger & Jason Feltman5 min read

Hosts of The Insurance Dudes Podcast — 1,000+ episodes helping insurance agents build elite agencies

Toby Hedges on Building a Powerhouse Insurance Agency in Any Market — Growth Strategies (Part 1)

Geographic determinism is the belief (often unconscious) that where you are limits what you can build. Agents in smaller markets tell themselves the leads are worse, the competition is different, and the ceiling is lower. Then someone like Toby Hedges comes along and makes that story very hard to sustain.

Toby built something worth talking about in Mississippi. Not in spite of his market, but through a mastery of the fundamentals that work everywhere: mindset, systems, team development, and a relentless focus on the client experience. This is Part 1 of his story. Continue to Part 2 for the tactical breakdown.

Toby's Origin Story in Insurance

Toby didn't come into insurance with a silver spoon or a built-in book of business. He came in the way most agents do: with some hustle, a lot of uncertainty, and a commission structure that meant every week was a new test of his ability to produce. The early years were a tutorial in what doesn't work: chasing every lead source, trying to be all things to all prospects, and measuring success by activity rather than outcomes.

The inflection point for Toby came when he stopped treating his agency like a sales job and started treating it like a business. That transition requires a level of self-honesty that a lot of agents never get to: the recognition that working hard is not the same as working on the right things. Toby got there, and it changed everything.

What he built from that point was an operation with genuine structure: defined roles, tracked metrics, a team that knew exactly what was expected of them and had the tools to deliver it. In a market where the conventional wisdom was that you couldn't build something sophisticated, Toby quietly built something sophisticated.

His consistency is what stands out most when you hear him describe his operation. Not the flashiest lead source, not the most sophisticated tech stack, not the most innovative marketing approach. Rather, it's a relentless, almost boring consistency in the fundamentals that most agents abandon when they get comfortable or when things get hard.

The Beliefs That Built Toby's Agency

Market excuses are productivity killers. Toby's position on this is unambiguous: if you're blaming your market for your results, you've given up control of your own business. Every market has potential clients who need insurance. Every market has prospects who are underinsured. Every market has clients who will switch to an agent who genuinely serves them better. The market isn't the variable. The agency is.

Culture is something you build deliberately, not something that just happens. Toby talks about the intentional work he's done to create a team environment where people stay, grow, and perform at a high level. This isn't about perks or office aesthetics. It's about whether people feel valued, trained, and connected to a mission bigger than making quota. Agencies with strong cultures spend less on recruiting because their people don't leave. That's a direct economic benefit, not just a feel-good outcome.

The client experience is a growth strategy. In smaller markets, word of mouth is disproportionately powerful. Toby understood this early and built his client experience around generating the kind of referrals and reviews that create organic growth. Every interaction is a chance to create an advocate or a detractor. He designed his processes to consistently produce advocates.

Patience with people is an investment, not a virtue. Developing an agent takes time. Toby's approach to agent development is more invested and more patient than most agency owners are comfortable with because he's done the math on what it costs to churn through people versus developing them. The latter is almost always cheaper and almost always produces better outcomes.

What This Means for Your Agency

Before you move to Part 2, take stock of your own market mindset. Are you competing fully in your market, or are you operating with a quiet ceiling based on geography, demographics, or competitive conditions that you've accepted as immovable? Write down three things you've told yourself aren't possible in your market and challenge each one with a specific counterexample.

Then look at your client experience from the outside. If you were a client, would you refer your agency to a friend? Not because the agent was nice, but because the experience (from first contact through renewal) was genuinely better than what they'd get elsewhere? If the honest answer is "probably not," you have a design project, not a sales problem.

The Bottom Line

Toby Hedges is proof that the ceiling most agents see isn't imposed by their market. It's imposed by their assumptions. The fundamentals of great agency building work in Mississippi the same way they work in Manhattan. Pick them up, apply them consistently, and watch what happens. Continue to Part 2 for the specific tactics.


Catch the full conversation:

Level up your agency:

Listen to The Insurance Dudes Podcast

Get more strategies like this on our podcast. Available on all platforms.

Related Episodes