Is It Time to Grow Through Acquisition or Partner for Scale? One Chicago Agency Owner's Decision Point

In a market flooded with insurance M&A activity, agency owners are increasingly faced with a pivotal decision: grow alone, acquire others, or partner for scale. A recent conversation between Equity Expansion and a Chicago-based insurance agency owner sheds light on what drives that decision and what makes some owners say "not yet."

A Chicago Agency with Solid Foundations

The agency, founded in 2013 by an experienced insurance professional, currently writes approximately $6 million in direct written premium. With just four employees (including the owner), the agency remains intentionally lean, prioritizing work-life balance over aggressive expansion.

"I have four young kids, ages four to twelve," the owner shared. "Right now, I want to be home for dinner every night. I’m not trying to chase multi-state clients or build a national empire yet."

Instead, he’s focused on perfecting operations: building solid systems, refining internal processes, and positioning the agency for strategic growth ten years down the road.

Exploring Options but Not Ready to Sell

Despite receiving eight or nine calls from buyers in the past year, the owner wasn’t actively seeking a sale. But a persistent outreach from Equity Expansion convinced him to at least explore what partnership could offer.

What followed was a transparent, no-pressure discovery conversation. Equity Expansion outlined why so many agency partnerships are happening now especially among firms in the $700K–$1M revenue range:

• Operational strain increases with growth
• Owners wear too many hats HR, IT, finance, compliance
• Infrastructure demands (hiring, benefits, back office) become overwhelming

How a Strategic Partner Could Help

Equity Expansion explained how a partnership might look for a firm of this size:

• Back-office relief: Full HR and accounting departments take over hiring, payroll, PTO management, and compliance
• IT and licensing support: No more buying new equipment or navigating multi-state carrier appointments alone
• Financial structuring: In a hypothetical $2 million valuation, the owner could receive:
  • $1.6 million in upfront cash (for 80% equity)
  • $400,000 retained in equity with 4–5x potential growth
  • Additional earnouts and comp structure for future upside

But Equity Expansion made it clear: “This isn’t about convincing you to sell. It’s about exploring options. You’ve earned the right to make this decision.”

Respecting the Owner's Vision

While the numbers made sense, the owner’s heart was set elsewhere: he wanted to buy, not sell.

"I want to be the guy building a team, not exiting. One day, I want to call you and say, ‘Help me find agencies to acquire.’"

Equity Expansion responded with encouragement and practical advice:

To become a serious buyer in today’s competitive M&A market, owners need:

• A well-built back-office infrastructure to absorb acquisitions
• A compelling equity offering for potential sellers
• Financial packages that include upfront cash, earnouts, and long-term wealth opportunities

Building Toward a Future Partnership

Though not ready for partnership today, the call built a foundation for potential future collaboration.

"If you have questions as you grow, call me," Equity Expansion offered. "We know the players, the market, and the math. When you're ready, we’ll help you build something big."

Takeaway: There’s More Than One Way to Win

This agency owner is on a thoughtful, long-term path focusing on family today while preparing to scale tomorrow. Equity Expansion respects that vision and stands ready to support it.

Whether you’re ready to take chips off the table, delegate back-office burdens, or build your acquisition platform, Equity Expansion offers strategic support tailored to your journey.

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