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401(k), Mega Backdoor Roth and the Premium Tax Credit | Sean Mullaney | Ep 409

In this episode: w2 employment to self-employment, s-coporations vs self-employment, avoiding penalties, megas backdoor roths, retirement planning, and health insurance.

Most of us are familiar with a W2 job, and there is a certain level of convenience that comes with working a W2 job as it relates to retirement planning and taxes. So much so that it can be daunting to want to embark out on your own journey and have to figure it all out on your own. This week we are re-joined by our “in-house tax expert” Sean Mullaney to discuss the tax and retirement sphere as it relates to being self-employed. While we are not offering advice, this week’s episode is meant to act as a resource to listeners curious about the steps and unknowns that come with the self-employment territory. With the same excitement and motivations gained from getting to run your own business, those same motivations and excitements can still be applied to navigating your retirement and taxes once you remember that it is now within YOUR control!  The fear of the unfamiliar may not be as daunting and complicated as you may think, and figuring out these factors requires you to take the same initiative and action that is required throughout your entire FI journey! 

The discussion is intended to be for general educational purposes and is not tax, legal, or investment advice for any individual.

Sean Mullaney:


  • 1:42 – Introduction
  • 2:38 – W2 Employment to Self-Employment
  • 11:34 – S-Corporations vs Self-Employment
  • 14:03 – Avoiding Penalties When Making Estimated Payments
  • 19:29 – Saving For Retirement As An Entrepreneur
  • 24:00 – Employee vs Employer 401k Limits and Mega Backdoor Roth
  • 33:54 – Is The Mega Backdoor Plausible For The Self-Employed?
  • 41:03 – Roth IRA Conversions
  • 43:15 – Addressing The Uncertainty Around The Employer Maximum
  • 53:40 – ACA Plans and Navigating Health Insurance As A Solopreneur
  • 63:34 – What Counts As Income?
  • 68:41 – 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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