Dec. 10, 2025

EP 136: The Retirement Strategy Hiding in Plain Sight with Thomas Drapala

Show Notes

Owners fixate on the purchase price of their exit, but the bigger loss to long-term income can come from how Social Security is handled. Get it wrong, and you can quietly lose six figures.

Thomas Drapala, Director of Strategic Partnerships at Registered Social Security Analysts (RSSA), explains why 96% of Americans leave money on the table when they treat Social Security as an afterthought. Drawing from his client work, he discusses how self-employment tax, entity structure, and “reasonable compensation” influence Social Security benefits. Thomas also walks through how RSSA’s analysis helps owners save thousands of dollars a year in taxes, protect future benefits, and make Social Security a strategic part of their exit plan so it isn’t ignored.

In this episode, you will:

Understand why every owner should check their SSA earnings record and run an independent analysis before selling
Learn what younger owners should do now to avoid losing benefits later
See how RSSA analysis ties Social Security into your full exit and retirement plan

Highlights:

(00:00) Meet Thomas Drapala

(01:42) The shocking statistics on Social Security optimization

(03:32) Understanding Social Security rules and benefits

(05:49) Strategies for business owners to maximize Social Security

(13:37) Case study: The bagel store owner's Social Security optimization

(16:52) When it makes sense to bring in a Social Security expert

(24:12) How a full Social Security review is done

Follow Thomas:

Connect on LinkedIn: https://www.linkedin.com/in/thomas-drapala-rssa%C2%AE-878611207/

Email: thomas.drapala@rssa.com

Learn more about Registered Social Security Analysts: https://rssa.com/