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Social Security Deep Dive | Denis Shapiro | Ep 474

In this episode: social security, disability, calculating social security, claiming social security, and due diligence.

This week, we are joined by listener and owner of Financial Security Advocates Dennis Shapiro to talk through some of the insights and misconceptions surrounding Social Security Benefits and what factors and resources you should consider while approaching retirement. The beauty of FI is that it opens up opportunities for you to retire early, but oftentimes, we don’t consider how retiring early or even starting your own small business can impact your Social Security. While there is no true way of mastering the system to get the most benefit, there are many ways to prepare and plan in order to get the most out of your social security benefits! Remember, these benefits are not just safety nets when it comes to retirement but can be an additional tool for investment that keeps you comfortable in your FI. 

Denis Shapiro:


  • 1:16 – Introduction
  • 5:10 – What Pays for Social Security?
  • 11:13 – Social Security and FI/Disability Insurance
  • 17:30 – What Earnings Go Towards Social Security?
  • 23:19 – Disability, Work Subsidies, and Income Related Work Expenses
  • 29:03 – How Social Security Benefits Are Calculated
  • 37:05 – Claiming Social Security
  • 39:59 – Social Security and Medicare
  • 44:28 – Social Security and Due Diligence
  • 56:27 – Working and Disability Benefits
  • 59:59 – Conclusion

Resources Mentioned In Today’s Episode:

Choose FI has partnered with CardRatings for our coverage of credit card products. Choose FI and CardRatings may receive a commission from card issuers. Opinions, reviews, analyses & recommendations are the author’s alone, and have not been reviewed, endorsed or approved by any of these entities. American Express is a ChooseFI advertiser. Disclosures.
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