Being a captive insurance agent is not easy. Some
After a decade in the captive world, I reached my breaking point. I'd weathered three major rate cycles, dealt with abrupt commission changes, and watched as my carrier exited lines of business that made up a large chunk of my revenue. The company's evolving strategy no longer aligned with my goals and I realized I had capped out. If I wanted to build something bigger, I had to make a change.
Here are five questions for agents considering this transition.
Why are you leaving? (and are you ready)
Before making the jump, agents need to be brutally honest with themselves: Is this about dissatisfaction, or do you have a real entrepreneurial drive? Independent agents don't just sell policies; they run businesses. That means managing operations, prospecting, marketing, and compliance, often solo at first. If you're not ready to take full ownership, it may not be the right move.
When I was at this inflection point, I could've stayed put, restructured again to fit someone else's playbook, and maybe grown a bit. But I knew I'd lose the team that helped me build what I had and, worse, I'd lose my passion. Instead, I chose to start fresh, keep my team, secure funding, and take a calculated risk with the potential for a 10x upside. For me, it ended up being the best decision I ever made. But to assess if it's the right decision for you, ask yourself:
- How will I finance my new agency? Will I use proceeds from a sale, a business loan, or both?
- Who owns my current marketing system — me or the carrier?
- What's my current quote volume, close rate, and retention ratio? What would those numbers look like with broader market access?
- What tech tools will I need to handle quoting, payments, CRM, and compliance?
- When do I expect to break even and how will I bridge that gap?
What infrastructure will I need?
Captive agents often underestimate the backend support they lose when they leave their agency. CRM systems, quoting tools, policy management software, phone operating systems, lead generation platforms - they all become your responsibility when going independent. Investing in the right infrastructure early can make or break your success.
My advice is to start small. Resist the urge to chase shiny tools or overbuild, and instead focus on what drives revenue and scale as your business demands it. Your early time and money should go toward sales and marketing, not tech bells and whistles.
To operate at a minimum, you'll need an agency management system, phone system, accounting/payment software, Microsoft 365 bundle, website, and social media presence. From there, evolve your tech stack as your business grows and requires it.
What's the right carrier mix?
One of the biggest advantages of independence is access to multiple carriers. But more isn't always better. Agents should seek a balanced portfolio that allows them to be competitive without becoming overwhelmed.
My recommendation for new agents: secure at least three legacy carriers for credibility, a regional carrier for pricing flexibility, a few specialty carriers for outliers, and one excess/surplus lines carrier to handle tough risks. Each has premium requirements, so use a brokerage partner like Darkhorse to take the contractual burden off your plate and accelerate your ramp-up.
What's your personal brand?
In the captive world, the brand does the heavy lifting. In the independent world, you are the brand. That means building visibility, trust, and credibility in your community and online. Whether it's hosting seminars, developing a referral network, or showing up consistently on social media, agents need to establish authority beyond just selling policies.
Additionally, it's imperative to avoid some common pitfalls – things like inconsistency, generic messaging, over-automation with no human touch, and failing to put in the relationship-building. You don't need a massive budget to build your brand, but you do need to show up every day.
What's the right support system?
It's going to take some time to find the magic mix of tools and platforms that best fit your new business. Give yourself some grace. In my early days, I cycled through four management systems, three phone providers, two accounting firms, and countless recruiters. Trial and error was my only option.
Join a local networking group like Business Network International (BNI), find an agency management system that fits your budget and workflow, and partner with a brokerage that shares your values and understands your goals.
