For many insurance agency owners, the goal is growth more clients, more staff, more markets. But for others, success looks different. For one Barrington, Illinois–based agency owner, the ultimate goal wasn’t scale, it was sustainability. And after building and selling tens of thousands of policies, surviving industry volatility, and weathering broken partnerships, he found that a lean, controlled model offered something rare in the insurance business: peace of mind.
This is the story of how one veteran insurance professional turned a once-sizable operation into a streamlined annuity and why, despite Equity Expansion’s best offerings, he chose to remain independent.
From High-Fashion Footwear to Health Insurance
Before launching his insurance career, the agency owner spent 15 years managing major accounts in the U.S. footwear industry. He worked with top designers and large retailers like Target and Walmart. But when his health began to suffer and commissions were slashed during internal company shakeups, he walked away from the industry without a job lined up.
“I resigned without a plan. It was all stress-related,” he shared. “I just knew I couldn’t keep going like that.”
After months of job searching and fielding offers that didn’t feel right, he entered the insurance industry in partnership with a growing health agency. It was a slow start with no commissions for the first six months but by the end of year one, he became a partner and began building a downline of agents.
Scaling Fast and Then Starting Over
His first solo agency did well, but everything changed when he partnered with a large brokerage to build out a call center. At its peak, the call center had 12 agents and sold over 16,500 health insurance applications, resulting in more than 13,500 active clients. The commissions were strong, and business was booming.
But when the brokerage’s key partner (Cigna) pulled in-house and started withholding payments, everything came crashing down.
“They weren’t paying the brokerage, which meant I couldn’t pay my agents. I had to get creative to keep them working and making money.”
He formed separate LLCs to get licensed under new carriers, circumventing the stalled payments. The workaround helped temporarily. But when the brokerage found out, they cut ties entirely and threatened legal action.
A high-profile attorney helped him settle the matter, and the non-compete officially ended in March of this year. But the experience left a lasting mark.
Operating Lean, Living Free
Today, the agency is a tight run operation with the owner and a few 1099 agents. Annual commission revenue ranges from $125K to $150K, derived from a mix of:
- Private individual plans paying $110–$150 per member per month
- Medicare (~100 clients)
- Dental and ancillary products
- Select group health clients (including one small group paying $600/month in residuals)
With licenses in 28–31 states, he’s able to write nationwide. He generates inbound business via a locally ranked website and leverages a 15,000+ person database from previous sales. Most importantly, he only works three days a week.
“I tell people I’m retired, just not in the traditional sense. I work a few days, keep my clients happy, and the revenue comes in like an annuity.”
Why He Considered Equity Expansion and Why He Walked Away
Equity Expansion initially reached out as part of a targeted search for insurance agency owners in the Midwest with books in the $100K–$300K range. With a strong back-office infrastructure and partner agencies nearby, Equity Expansion saw a potential fit for a tuck-in partnership.
The offer would have included:
- 2x multiple on commission revenue
- Equity rollover into a larger firm
- Back-office support (HR, payroll, accounting, service, marketing)
- Access to stronger carrier contracts and growth capital
But the owner was clear: he wasn’t looking to grow exponentially or sell out. His goals were lifestyle-driven.
“Why would I give up control just to make a little more? I’m comfortable. I don’t need to scale. I want to enjoy life.”
Having lived through a failed partnership that nearly upended his agency, he valued autonomy more than upside. The Equity Expansion team respected that choice.
“This is a monumental decision,” said the Equity Expansion VP. “And you’ve already made it, you're running your business your way. That deserves respect.”
The Power of Saying No
Not every agency owner is looking for an exit. For some, like this Illinois-based leader, the agency is an engine of freedom a vehicle for financial stability, flexibility, and fulfillment.
His story is a reminder that partnership isn’t about pressure. It’s about options. And when those options align with your goals whether that’s scaling to $2M+ in revenue or preserving your independence Equity Expansion can help you evaluate your best path forward.
Is a Strategic Partnership Right for You?
Whether you’re building toward retirement, looking to offload operational responsibilities, or seeking equity-backed growth, Equity Expansion helps insurance agency owners like you chart the next chapter on your terms.
✅Confidential conversations
✅ Personalized deal structures
✅ Equity rollover + upfront cash options
✅ Operational support to reduce your workload
Schedule a confidential consultation to explore your options, pressure, no obligation.
