That’s the question an insurance agency owner in Milwaukee, Wisconsin, has been asking himself.
With over a decade of experience in insurance and a previous career in internal audit and finance the solo operator has built a lean, profitable business. His agency generates an estimated $250,000 in revenue, with an EBITDA margin over 60%, thanks to low overhead and zero full-time employees. He writes 90% personal lines and 10% commercial, keeping a tight carrier list and managing everything manually through Excel.
But he’s not just thinking about today he’s planning 5, 10, even 20 years ahead.
This owner knows he’s not quite ready to sell. He’s still operating from home after downsizing during the pandemic. He doesn’t have an AMS system or staff. And yet, he’s already building his roadmap for long-term growth: opening a brick-and-mortar office in the next 1–3 years, hiring producers, and expanding across Wisconsin and into neighboring states like Illinois and Minnesota.
His vision is not just about organic growth. It includes acquisitions too. By identifying smaller, retiring agencies in his region, he’s aiming to scale his footprint while staying nimble.
But here’s the kicker he’s also thinking ahead to a perpetuation plan.
If he were to leave unexpectedly, he wants his family to know what to do, who to contact, and what the agency is worth. His ideal scenario? Pre-negotiated valuation formulas tied to his agency’s EBITDA, ensuring continuity and value for his loved ones.
The conversation also revealed that while his agency might be too small for a partnership today, he’s not far off.
Partnership models typically begin at $500K in revenue and scale to multi-million-dollar deals. At that stage, agency owners can receive 80% of the purchase price as upfront cash and roll forward 20% as equity. That equity often appreciates 3–5x in as little as three to five years turning a $400,000 roll into $1.6M or more.
For sellers who stay on and continue producing, the benefits stack up:
The Milwaukee owner may not be ready to sell today but his mindset puts him ahead of many. By staying connected with experienced M&A advisors, benchmarking what makes a business attractive to buyers, and growing smartly, he’s positioning himself for a profitable and low-risk transition.
Whether you’re five years away or twenty, the time to think about your future is now.