In this episode of Bricks & Risk, Tim Garrity and Sean Mooney sit down with Greg Hogan, President of Carrabba Agency Insurance, to discuss his 38-year journey in the insurance industry and how he transformed a traditional local agency into a nationally recognized Best Practices Agency.
Greg shares how he purchased his first agency after reaching a ceiling in his previous career, and how that decision eventually led to the acquisition of two additional agencies. Rather than pursuing growth for growth’s sake, Greg explains why every acquisition was centered around long-term relationships, operational efficiency, and preserving the trust clients had built with their existing agency.
The conversation dives into the realities of buying insurance agencies, evaluating acquisition opportunities, retaining clients after ownership transitions, and identifying hidden opportunities within acquired books of business. Greg also reveals how one acquisition led to a valuable carrier appointment that continues to benefit the agency years later.
Beyond acquisitions, Greg discusses the importance of creating operational efficiencies through technology while maintaining an old-school commitment to service. From integrating texting into agency workflows to creating systems that improve communication and client responsiveness, he explains how small improvements can create significant long-term gains.
One of the most compelling parts of the discussion focuses on agency profitability. Greg shares how Carrabba Agency has achieved EBITDA numbers that significantly outperform industry averages while growing revenue and reducing staffing requirements through process improvements and smarter operations.
The conversation also explores the current state of personal lines insurance, including homeowners and auto insurance pricing, market corrections, carrier profitability, and why many consumers still underestimate the importance of proper coverage limits. Greg and Sean discuss real-world claims examples that highlight the value of umbrella policies, uninsured and underinsured motorist coverage, and why agencies should focus on education instead of simply selling policies.
Perhaps the biggest takeaway from the episode is Greg’s unwavering commitment to doing the right thing for clients. He explains why his agency often walks away from business when clients insist on inadequate coverage and why he refuses to compensate employees solely based on sales production. Instead, his team is rewarded for protecting clients properly and delivering exceptional service.
Whether you're an insurance agency owner, real estate investor, entrepreneur, business operator, or simply someone interested in building a business with strong fundamentals, this episode offers valuable lessons on leadership, acquisitions, client retention, operational excellence, and long-term growth.
Greg’s approach proves that sustainable success is built through trust, consistency, and a willingness to prioritize clients over short-term sales opportunities.
#InsuranceAgency #BusinessGrowth #Entrepreneurship #AgencyOwnership
⏱️ CHAPTERS
00:00 Introduction & Meet Greg Hogan
04:20 How Greg Accidentally Entered the Insurance Industry
08:10 Purchasing His First Insurance Agency
12:45 Scaling Through Agency Acquisitions
17:30 Finding Agency Acquisition Opportunities
21:15 Retaining Clients After an Acquisition
25:10 Hidden Value & "Diamonds in the Rough" in Agency Deals
29:00 Building Operational Efficiency Through Technology
33:20 Insurance Agency Profitability & EBITDA Explained
37:15 Why Personal Lines Insurance Has Driven Growth
41:20 Consultative Selling vs Transactional Selling
45:00 Always Do the Right Thing: Greg's Core Business Philosophy