Case Studies in Advanced Retirement Planning (Strategies That Go Beyond the 401(k))

Small Business Tax Savings Podcast

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What if everything you thought you knew about retirement planning was just scratching the surface? In this episode, Mike sits down with retirement expert Matt Ruttenberg to break down advanced retirement strategies that go way beyond the traditional 401(k).

Chapters:

(01:22) Understanding the Retirement Plan Stack
How business owners can layer a safe harbor 401(k), profit sharing, and cash balance plan to maximize tax savings while customizing benefits for themselves vs. employees.

(04:55) High-Income Dentist Case Study ($750K Income)
How a 50-year-old dentist can contribute over $200K pre-tax annually, avoid costly employee contributions, and potentially boost deductions by another 35% using life insurance inside a cash balance plan.

(11:36) The Qualified Swap Strategy
Using IRS Code §7702 to mimic a Roth account by funding a life insurance policy inside a qualified plan, then legally moving it out tax-free after five years.

(15:20) Online Consultant Case Study (Retire by Age 50)
How a 42-year-old solo S-Corp owner can combine a self-directed solo 401(k), mega backdoor Roth, and future Roth conversions to retire early while minimizing taxes on withdrawals.

(21:40) Real Estate Investing Inside a 401(k)
How self-directed plans can allow for non-traditional investments like crypto or property.

(26:44) Real Scenario #3: Seasonal Landscaping Business

How solo 401(k)s can be used even with employees (if structured right)

(34:12) When to Use Non-Qualified Retirement Plans
Non-qualified plans can help business owners bypass traditional testing requirements and reward only specific employees, without triggering mandatory contributions across the board.

(39:01) How to Properly Design a Life Insurance Plan
Why poor design ruins tax benefits and how to build a policy that acts like a Roth

(45:30) Common Misunderstandings Around 401(k) Plans
Why many business owners avoid retirement plans due to misconceptions about complexity or cost.

(48:16) Matching the Right Plan to the Right Goal
How to choose between a traditional 401(k), profit sharing, cash balance, or non-qualified plan depending on your goal.

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Podcast Host: Mike Jesowshek, CPA - Founder and Host of Small Business Tax Savings Podcast

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🎙 ABOUT THE PODCAST

The Small Business Tax Savings Podcast is your go-to resource for cutting-edge tax strategies designed to help entrepreneurs and small business owners legally slash their tax bills. Hosted by Mike Jesowshek, CPA, this podcast breaks down complex tax topics into clear, actionable, no fluff insights, so you can maximize your savings and keep more of your hard-earned money.