Growing an Estate Planning Law Firm

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 humor 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

Full Transcript:

Awais (00:01) For thirty years, my next guest has built his law firm on one blunt idea: "If you don't plan, you're stupid". He even trademarked it. Andrew Rosenberg runs an estate planning, elder law, and personal injury practice in Coral Springs. He has built a real marketing engine around it. Let's get into what's actually worked. Thank you for coming in today, Andrew.

Andrew Rosenberg (00:30) Thank you for having me. It's a pleasure.

Awais (00:33) So Andrew, I have met a lot of lawyers, but I rarely find people working on so many things. I learned from your YouTube that you have written a book, which is also called If You Don't Plan, You're Stupid. You also run a regular podcast, produce YouTube content, host free workshops, and run a Kajabi VIP portal. I want to learn about everything you're doing today and how these initiatives brought you to where you are. Let's start with the book. How was the experience writing it?

Andrew Rosenberg (01:16) I'll tell your audience right off the bat: I hate writing. I am not a writer. It is not something I like to do, and my attention span is about three minutes. So for me to write a book was a huge undertaking.

The book came about in an interesting way. First, let me tell you how the title came about. Again, the book is called If You Don't Plan, You're Stupid, and it's available on Amazon. I was part of a weekly networking group called BNI (Business Networking International). Every member is exclusive to their area of expertise, so I was the estate planning attorney.

During meetings, everyone had to do a 30-second elevator speech about what they do and end with a tagline. When my turn came, I stood up, quickly explained what I did, and then tried to think of a tagline. I pointed at everyone and said, "And remember, if you don't plan, you're stupid". Everyone looked at me like I was crazy. But then the next person got up and said, "Remember what Andy said, if you don't plan, you're stupid". Seven people repeated it that day. I realized I hit a nerve.

A couple of years later, I hired a business coach. I firmly believe attorneys should have a business coach. Even Tiger Woods, the best golfer in the world, uses a coach to keep getting better. My coach agreed I should write a book, and when I told her my tagline, she laughed and said to use it.

It took me about six to eight months to write. As an attorney writing a book, you're not trying to create a bestseller—nobody wants to read a boring legal book for fun. You write it to establish authority. It elevates you to an expert level in the eyes of the general public.

Awais (06:02) When you were writing the book, how did you know who would want to buy and read it, and ultimately become clients?

Andrew Rosenberg (06:34) I never went into it thinking it would be a mass-market bestseller. The audience for the book was the exact target market I advertise to for my firm: mom-and-pop families, couples with young children, or older parents whose kids have left the nest and need to get organized.

I already knew what topics to cover because I host so many workshops. To write it, I broke it down step-by-step: first topics, then chapter order, then section content. I used an AI writing assistant to outline chapters, but AI tends to run in circles and repeat itself, so I had to whittle 20 pages down to 5 and add my own personal voice, stories, and practical examples. Now when people read it, they tell me it sounds just like me talking.

Awais (11:24) Many attorneys struggle with marketing because they try to sound overly complex or authoritative. Do you think using a 6th-to-7th-grade reading level is better for sensitive legal topics like probate and trusts, or should attorneys sound more academically formal?

Andrew Rosenberg (12:50) In my 30-plus years of practice, I've found that talking down-to-earth so clients actually understand you—and stripping out the legalese—is far more effective. Don't talk like a lawyer; talk like a normal person.

If you talk over their heads with legal jargon, clients get lost. I'm a Midwestern guy from Indiana, happy-go-lucky, and just trying to help people. Clients don't want legal jargon; they want to know how to solve their problem so they can sleep at night.

When I write newsletters or articles, I run my text through the Hemingway Editor app. It consistently scores my writing at a sixth-grade reading level. Unless you are dealing exclusively with high-net-worth clients who specifically demand formal legal terminology, everyday people want plain English.

Awais (16:10) Many attorneys feel they must remain strictly serious in front of clients. In your podcast, you use humor, make jokes, and talk about your family. Does being humorous and relatable help build a law practice more than being strictly formal?

Andrew Rosenberg (17:28) Both matter, but having fun is fundamental to who I am. I joke all day with my staff and my clients.

Estate planning deals with death and disability—it's a very serious topic. Bringing humor into the meeting breaks the ice and helps people feel comfortable. The first 10 or 15 minutes of my client meetings are often just spent getting to know them and having a good laugh. In my workshops, the very first bullet point on my agenda is "We're going to have fun".

Attorneys unfortunately have a bad reputation, so showing that you are a normal human being with a family, dogs, and everyday issues makes clients feel safe. You still have to balance it with deep professional empathy during painful situations, but creating a relaxed environment works wonders. Recently, I interviewed a new associate who sat in on a client meeting. Afterward, he said he had never seen a legal meeting where people laughed so much, and he asked to be hired on the spot. Be authentic to your own personality, but if you have a humor-driven personality, embrace it.

Awais (24:10) When you're friendly and humorous, how do you prevent clients or staff from crossing boundaries or losing respect for your professional role?

Andrew Rosenberg (24:46) Clients know I'm a professional because during the meeting, we thoroughly address the serious details of their estate plan, documents, and family protection. I've never had a client cross that line.

With staff, it can happen occasionally. We have flexible hours, but recently there was a day when no support staff were in the office because everyone was working remotely. I called a meeting, put my foot down as a business owner, and told them we must have coverage in the office from 9 to 5 every day. I gave them 20 minutes to figure out the schedule among themselves, and they handled it immediately. You can be relaxed, but when boundaries are tested, you have to be firm.

Awais (27:04) New attorneys often struggle with lead generation and clients ghosting them after initial meetings. How do you handle client ghosting, and how do you protect your time?

Andrew Rosenberg (28:22) Years ago, I used to do all the work, do the signing meeting, and only collect payment at the very end. Then one day, a client vanished after I completed his entire estate plan. After that, I changed my policy permanently: clients must pay a 50% deposit upfront before any work starts. They must have skin in the game.

For consultations, I offer an initial free consultation. If a prospective client fails to show up without a valid reason, they lose the right to a free consult. To reschedule, we collect their credit card details and charge a $500–$600 fee for the time slot. Respecting your own time gives clients a reason to respect it too.

Awais (32:04) How do you handle price objections when prospective clients compare your rates to cheaper competitors?

Andrew Rosenberg (32:53) Pricing is always an issue, but you have to believe in your own value. When clients tell me someone else is cheaper, I say, "Good! You'll always find someone cheaper, and you'll always find someone more expensive. I am fairly priced for 30-plus years of experience and over 600 five-star Google reviews".

I remind them that estate planning is dynamic, not a one-and-done transaction. They are paying for an ongoing relationship and continuous communication. Recently, a family wanted to skip essential estate planning documents to save money and only do a basic deed. I told them directly that doing so was inadequate and that I wouldn't take the case unless we did it right. Once I explained the value, they signed up for the full plan. If you have confidence in your work, clients will respect your price.

Awais (36:52) In estate planning, firm owners often struggle to maintain relationships with the next generation after the original client passes away. How do you build multi-generational relationships?

Andrew Rosenberg (37:30) First, unlike many firms, I do not hold original wills in my vault to force families back to my office. I give clients their original documents.

To build long-term relationships, I launched a private client program called the "Estate in One Place Private Client Group" for $695 a year. Members get monthly Zoom office hours where they can bring family members to ask legal questions. We also host fun annual events—for example, we recently rented out a pickleball facility with professional coaches, round-robin tournaments, massage therapists, and catered food, inviting clients to bring their children and friends. We also publish monthly newsletters. Staying continuously engaged keeps us connected across generations.

Awais (40:41) When evaluating prospective clients, is it more important to focus on closing the sale or seeking the truth through strict qualification and disqualification criteria?

Andrew Rosenberg (41:42) Always seek the truth over the sale. I love sales, but after 30 years in practice, I know that sometimes the best cases are the ones you say "no" to.

Problem clients will drain your time, energy, and peace of mind. It is completely okay to turn down a client, refer them elsewhere, or even fire a client if it's not a good fit. Additionally, in estate planning, if a client wants to disinherit a family member, we carefully document and videotape the session with their consent so there is clear evidence if beneficiaries attempt to contest the estate later. Always go with your gut, stick to the truth, and don't take on bad-fit clients.

Awais (45:05) Thank you so much for joining us today, Andrew. How can listeners get in touch with you or learn more?

Andrew Rosenberg (45:53) Thank you for having me. Listeners can reach me by email at Andrew@RosenbergLawFirm.net (mention you heard me on Awais's podcast), call our office at (954) 755-7803, or visit our website at RosenbergLawFirm.net.

Awais (47:04) Andrew is a natural communicator and salesperson because he knows how to qualify, respect his time, and share relatable stories. Thank you to everyone for tuning in—don't forget to share and subscribe!

Resources & Downloads

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📊 Book a Strategic Law Firm Growth Audit

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.