Advertise on podcast: J. Sterling Hughes Show

What does it take to grow a law firm through acquisitions instead of building everything from scratch? In this episode of The J. Sterling Hughes Show, Jeff sits down with Tom Shipley, co-founder of DealCon and the Advisory Board, to explore a practical approach to law firm mergers and acquisitions. Tom shares lessons from building acquisition platforms, including how to find motivated sellers, structure creative deals, and use acquisitions to increase business value. Jeff also discusses how Tom's guidance helped Sterling navigate its recent Florida acquisition, from negotiating terms to building trust with the sellers and resolving challenges before closing. They also explore the economics of multiple expansion, the importance of understanding a seller's motivations, and why relationships can make or break a transaction. A practical conversation for law firm owners considering acquisitions as their next stage of growth.

What does it look like when a non-lawyer entrepreneur partners with an attorney to build an MSO around an estate planning firm? In this episode, Jeff talks with Tim about how the structure works, why the business logic is so strong, and why he expects to see many more of these deals. Tim shares the story behind the deal, including the 12-plus months it took to paper, the moment it nearly fell apart over ownership percentages, and how he turned it around.  He also walks through the AI operating system he's building for estate planning and elder law firms, how he thinks about valuing small firms (roughly 2x normalized earnings, with recurring revenue getting better treatment), and his plan to expand by bringing in other firms.  He closes with a warning on AI compliance, including why business associate agreements (BAAs) matter for any tool handling client data. If you're curious about MSOs in consumer law, this is a great place to start.

How do you build a law firm from scratch and reach a $2.0 million run rate in just 18 months? On The J. Sterling Hughes Show, Jeff Hughes sits down with Anthony Cooper to unpack how Anthony and his wife, Charlean, approached rapid growth with clear roles, disciplined hiring, and a focus on scalable systems.  Anthony walks through their early client acquisition strategy, the decision to invest in marketing, refining intake to focus on qualified leads, and the challenges of adding attorneys quickly.  He also shares a costly lesson from taking his eye off marketing performance—and how the firm navigated attorney turnover without sacrificing client service. It’s a practical look at the decisions, growing pains, and systems behind scaling a young law firm.

What does a law firm acquisition look like from the buyer’s side? This week, Alex Peterson turns the tables and interviews Jeff Hughes about Sterling Lawyers’ acquisition of Family First Legal Group—from their first conversation through financing, closing, and the early stages of integration. Jeff explains what Sterling looks for in an acquisition, why culture and credibility can make or break a deal, and how a firm’s systems and independence from its founder affect value.  He walks through the six-month transaction, a late-stage banking scare that put the closing timeline at risk, Sterling’s “first do no harm” approach to integration, and what surprised him most along the way. For law firm owners considering a future sale, this episode offers a practical look at the buyer’s perspective—and why building a business that can operate without you matters.

What's it actually like to sell a $5.5 million family law firm? In this episode, Jeff Hughes sits down with Alex Peterson, who, alongside his wife Katie, built Family First Legal Group in Naples, Florida — and ultimately sold it to Sterling Lawyers.  Alex walks through the entire journey from the seller's side: an unexpected inbound listing, the first meeting that built trust, negotiating the letter of intent, choosing not to accept an earn-out, a grueling due diligence process, keeping the deal confidential from his team, and the tense final hours waiting on bank wire transfers before close.  He also opens up about the emotional moment of telling his team, what he'd do differently, and why building a company that could run without him made the entire sale possible.  A candid, detailed look at consumer law firm M&A from the seller's perspective.

Welcome to The J. Sterling Hughes Show, a podcast about People Law Firm M&A and big-picture strategy from an operator’s perspective. In this introductory episode, Jeff shares why he stepped away from the day-to-day CEO role at Sterling Lawyers to focus on M&A and long-term strategy, what he’s learning as consolidation begins to take shape across consumer law firms, and lessons from Sterling’s recent acquisition of Family First Legal Group. This show isn’t about theory. Jeff will share what he’s seeing, who he’s meeting, what’s working, what isn’t, and the lessons learned along the way—with the goal of helping law firm leaders make better-informed decisions as they grow and scale their firms.