Episode 48

Episode 48: Ben Glass

What's In This Episode?

In this episode of Harry Handles It, Harry sits down with Ben Glass, a disability attorney, legal marketing pioneer, and 40-year veteran of taking on insurance companies for injured and disabled clients. Ben shares how he built BenGlassLaw into a firm managing over $33 million in disability benefits for clients—while simultaneously founding Great Legal Marketing to help thousands of solo and small firm lawyers scale their practices. From securing a landmark $6 million recovery for a family’s tragedy to challenging the legal establishment’s conventional wisdom on lawyer wellness and firm culture, Ben breaks down the operational and marketing playbook that separates thriving practices from struggling ones. Learn how to build a disability law practice that actually fights for clients, create systems other lawyers can copy, and refuse to play by the profession’s outdated rules.

Episode Chapters

0:00 Introduction

1:15 42 Years in Legal Practice: The Evolution

3:30 Starting Ben Glass Law: From Trial Lawyer to Entrepreneur

5:45 Great Legal Marketing: Teaching the Business of Law

7:30 Defining Legal Marketing and Advertising

9:00 The Power of Relationships Over Ads

11:30 Direct Mail and Making Money in the Dark

13:15 Why You Can’t Rely on Algorithm Changes

15:00 Different Markets, Different Spending Levels

16:45 Fixing Your Funnel Before Buying More Ads

18:30 The Sales Team: Krista and Lead Conversion

20:15 The Lawyer Wellness Crisis

22:00 Design Your Life First, Then Your Firm

24:00 Understanding Profit and Cash Flow

25:30 Raising 9 Children While Running a Law Firm

27:15 Communication Skills and Family Lessons

29:00 Coaching, Mentors, and Mastermind Groups

31:30 Hiring and Retaining Great Teams

33:00 Why Bar Organizations Miss Entrepreneurial Lawyers

34:45 Resources for Law Firm Growth

35:30 How to Find Ben and Next Steps

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