Podcast Summary: The Law Entrepreneur – Episode 462

“Stop Tipping Uncle Sam: Tax Strategies Every Attorney Must Know”

Host: Bridget Norris (with intro by Sam Mollaei)
Guest: Frank Rekas, CPFA (“The Tax Whisperer”)
Release Date: September 26, 2025

Episode Overview

In this value-packed episode, host Bridget Norris welcomes Frank Rekas—the “Tax Whisperer” and personal CFO for attorneys. The conversation delves into practical tax strategies for law firm owners, with a focus on minimizing unnecessary tax payments (“tipping Uncle Sam”), optimizing entity structure, leveraging retirement plans, and building generational wealth. Frank shares actionable insights, relatable stories, and clears up misconceptions about financial planning—creating an approachable and motivating guide for attorneys at any stage of practice.

Key Discussion Points & Insights

Frank’s Niche: From Hockey Rinks to Helping Law Firms

• Origin of "Tax Whisperer"

  • Frank earned the moniker in a mastermind group, where peers recognized his knack for guiding attorneys through tax strategies many advisors ignore.
  • “If that's your quote, unquote, foot in the door, then you should lead with that. So I kind of toyed around with some sort of title, and that's what I came up with.” (Frank, 01:57)

• Focusing on Law Firm Owners

  • Frank’s specialization began organically—one referral led to another until he realized over 60% of his clients were attorneys.
  • “It was as easy and simple, as organic as that.” (Frank, 04:05)

Frank’s Approach to Financial Planning

• What Frank Actually Does

  • Collaborates with attorneys and their CPAs to maximize tax efficiency (not a tax preparer; focuses on strategy).
  • Comprehensive planning: tax reduction, risk management (insurance), wealth management (retirement planning, defined benefit plans).
  • “I'm not a CPA... but we're going to collaborate with my client's CPA to make sure that we're looking at all the different things that they could be doing either from entity structure… or deductions.” (Frank, 04:24)

• Dispelling Financial Planning Stereotypes

  • Many attorneys assume financial advisors just try to sell products. Frank’s client-centric approach is rooted in problem-solving, not sales.
  • “When I'm on an airplane... someone will say to me, so what do you do? I sell life insurance and conversation is over... I don't introduce myself as a financial planner either.” (Frank, 07:04)

Common Financial Mistakes Attorneys Make

• Top Mistakes (07:45–09:39)
  1. Not Knowing Your Numbers
     • Law firm owners often fail to dedicate time to understand cash flow, savings, and expenses.
     • “You have to dedicate some time. Now, having said that, if I talk to 10 law firm owners, five of them at least are going to say, Frank, do you know a CPA that's more proactive than mine?” (Frank, 07:45)
  2. Reactive vs. Proactive Tax Planning
     • Many CPAs are backward-looking (just filing returns) rather than proactive with tax strategy.
  3. Under-utilizing Retirement Plan Structures
     • A basic 401(k) isn’t sufficient for high earners; cash balance or defined benefit plans offer major tax advantages.

Concrete Tax-Saving Strategies

• Where Attorneys "Tip" Uncle Sam Most (10:00–11:17)

  • Inefficient entity structure: Sole proprietors earning $300-350k+ should consider S-corp status.
  • Underfunded retirement: Example of $200,000+ contribution leading to $70,000 in tax savings.
  • “The money is better in your pocket than it is in Uncle Sam's.” (Frank, 09:39)

• Proactive Tax Steps for Q4 & Year-End (13:19–15:40)

  • Set up "tax slush fund" accounts to ensure funds for quarterly/annual taxes.
  • Ensure all deductions & expenditures (equipment, memberships, software) are recorded and (if possible) accelerated into the current year.
  • Take advantage of new tax credits, e.g., $10,000 benefit for car purchases (check eligibility).

Barriers and Mindset Shifts

• Financial Avoidance & Mindset (18:30–20:00)

  • Attorneys excel at detailed legal work but often avoid their own financial planning—“If I don’t see it, it doesn’t exist.”
  • “Not making a decision is making a decision.” (Bridget, 20:00)

• Playing Catch-Up

  • Many attorneys wait years to pay themselves; the longer the delay, the steeper the climb to get on track.

Building and Passing on Wealth

• The Rockefeller Method Explained (22:03–24:44)

  • Leveraging cash value life insurance to create and pass down generational wealth—used by the Rockefellers and even Walt Disney.
  • “It's insurance first, it's not an investment... But there is an investment component... the death benefit is the piece that helps you pass along the generational wealth.” (Frank, 23:18)

• Education & Misinformation

  • Beware of financial “advice” from social media; prioritize trusted sources and context-appropriate strategies.

Implementation, Planning, and Relationship Building

• Starting the Process & Seeing Results (27:53–29:52)

  • Discovery process begins with a deep dive: gather info, analyze, propose top two strategies first.
  • First edition of the financial plan typically delivered within 90 days; progress seen within 30–60 days if information is provided promptly.
  • Emphasis on regular (quarterly/annual) check-ins to keep goals on track and maintain a personal relationship.

• Lifelong Planning—Not Just for ‘The Wealthy’

  • "It’s never too late; the heaviest lift is at the start—after that, it’s pretty smooth sailing." (Frank, 16:48–18:05)

• Succession Planning (32:46–34:03)

  • Importance of buy-sell agreements (for partnerships) and single-employer operating agreements (for solos) funded with insurance.
  • Planning now prevents bitter litigation and family hardship later:
    “You definitely need to have them in place before something happens, because when it happens, it’s too late.” (Frank, 33:11)

• Trends in Financial Planning

  • Independence in financial advisory is a growing trend—enabling more objective and client-centered guidance (34:25–36:34).
  • “We can be totally objective. Not that we weren’t before... but now it’s completely objective and I think that’s something you should look for.” (Frank, 34:33)

Notable Quotes & Memorable Moments

• On Proactivity vs. Reactivity

  • “Every decision has a consequence. Even not doing something is a decision. And that's a consequence.” (Frank, 19:15)
  • “Not making a decision is making a decision. You're just deciding to… sit there and not move forward, which is, like, the worst thing possible.” (Bridget, 20:00)

• On Generational Wealth

  • “Imagine if everybody who is a parent left their children something after they passed away to help them get started in their life… it kind of creates a snowball effect.” (Frank, 22:22)
  • “Walt Disney started Disney by borrowing money from his life insurance policy.” (Frank, 24:44)

• On Client Skepticism & Transparency

  • “In two years, what would have to happen for you to feel like we've had a good working relationship?” (Frank, 31:11)

• On Objectivity and Independence

  • “Make sure... what is being offered to you really is the right thing. That's probably the best way I can answer that because you want honest recommendations that are for you, not the advisor's pocket.” (Frank, 35:01)

• Final Takeaway

  • “The money is better in your pocket than it is in Uncle Sam's.” (Frank, throughout episode)

Timestamps for Key Segments

• 01:57 — Origin of “Tax Whisperer”
• 04:10 — Why focus on law firm owners?
• 07:45 — Top financial mistakes attorneys make
• 09:39 — Real-life tax savings example ($70,000 saved)
• 13:19 — Proactive steps for year-end tax planning
• 18:30 — Overcoming avoidance & mindset barriers
• 22:03 — Rockefeller Method (using life insurance for legacy)
• 27:53 — How quickly attorneys see results with Frank’s system
• 32:46 — Succession planning must-dos
• 34:25 — Trends: The rise of independent, objective advice
• 37:41 — One actionable takeaway for attorneys

One Action Attorneys Should Take

“Besides putting on your calendar to meet with a financial advisor for 30 minutes, discuss with someone whether that's the financial advisor and/or your CPA to make sure that you're taking advantage of all the tax advantages that are available to you. And if something's missing... you need to act on that because the money is better in your pocket than it is in Uncle Sam's.”
— Frank Rekas (37:41)

Find Frank Rekas on LinkedIn and the episode show notes for more resources.