Featured Guest
Episode Notes & Transcript
What does it take to run an estate planning firm for over 30 years while staying as authentic to yourself as can be? This episode features Andrew Rosenberg, an Estate Planning Attorney from South Florida. We explore the process of writing his book “If You Don’t Plan, You’re Stupid,” culture and relationships within Rosenberg Law, as well as maintaining boundaries in a professional setting. Andrew shares with us his unique way of employing humour and transparency within his interactions, and maintaining strong, authentic relationships with clients. There are also two very charming dogs here.
Timestamps
- 00:01:08 - Intro
- 00:02:18 - Writing “If You Don’t Plan, You’re Stupid”
- 00:07:28 - Finding a Readership
- 00:08:56 - More of Writing “If You Don’t Plan, You’re Stupid”
- 00:13:20 - Reading Level and Legalese
- 00:18:07 - Humour with Clients
- 00:25:30 - Boundary with Clients and Staff
- 00:28:29 - Chasing After Clients
- 00:33:42 - Dealing With Pricing Objections
- 00:38:04 - Relationship With a Clients’ Family
- 00:42:06 - Qualification and Disqualification Criteria
Resources & Downloads
📥 Growth Playbooks:
https://tinyurl.com/y8uk44fr
📊 Book a Strategic Law Firm Growth Audit:
https://tinyurl.com/3k7dzhca
Meet the Guest
Andrew Rosenberg is an estate planning, elder law, and probate located in Coral Springs, Florida with over 30 years of legal experience. Known for his approachable, humorous style and blunt trademark "If You Don't Plan, You're Stupid," Andrew runs an innovative legal practice focused on strong client relationships, practical marketing, and accessible legal education.
About the Host

Awais Haq
Legal Tech Consultant & The Lawyer Podcast Host
From civil engineering to revolutionizing legal tech, I’m a problem-solver driven by impact. Disillusioned by industry malpractice, I pivoted to build tech solutions that matter - first scaling an online tutoring marketplace to $800K ARR, then founding Time Technologies LLC in Nov 2024. With 19+ projects across edtech, government security, and AI, I now focus on empowering small to mid-sized law firms by slashing admin burdens.
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