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In today's episode, we'll be tackling a crucial topic for those of you who have transitioned from being employees to becoming self-employed or small business owners—deducting self-employed health insurance premiums. Navigating the intricacies of health insurance as an entrepreneur can be daunting, especially when it comes to tax deductions. We'll break down everything you need to know, whether you're a sole proprietor, single-member LLC, or operate under an S corporation or C corporation. From understanding where to report your premiums on your tax return to making sure you get the maximum deduction, this episode is packed with actionable insights.
What you'll hear in this episode:
04:45 Use an accountable plan for business reimbursements.
07:46 Filing through corporation saves on taxes.
If you like this episode, check out:
Should I Hire a Tax Strategist?
How to Read Your Tax Return
S Corp Salary Explained Like a 3rd Grader
Want to learn more so you can earn more?
Join Gusto today and get a $100 Visa Gift Card
Visit keepwhatyouearn.com to dive deeper on our episodes
Visit keepwhatyouearncfo.com to work with Shannon and her team
Watch this episode and more here: https://www.youtube.com/channel/UCMlIuZsrllp1Uc_MlhriLvQ
Connect with Shannon on IG: https://www.instagram.com/shannonkweinstein/
The information contained in this podcast is intended for educational purposes only and is not individual tax advice. Please consult a qualified professional before implementing anything you learn.
By Shannon Weinstein5
194194 ratings
In today's episode, we'll be tackling a crucial topic for those of you who have transitioned from being employees to becoming self-employed or small business owners—deducting self-employed health insurance premiums. Navigating the intricacies of health insurance as an entrepreneur can be daunting, especially when it comes to tax deductions. We'll break down everything you need to know, whether you're a sole proprietor, single-member LLC, or operate under an S corporation or C corporation. From understanding where to report your premiums on your tax return to making sure you get the maximum deduction, this episode is packed with actionable insights.
What you'll hear in this episode:
04:45 Use an accountable plan for business reimbursements.
07:46 Filing through corporation saves on taxes.
If you like this episode, check out:
Should I Hire a Tax Strategist?
How to Read Your Tax Return
S Corp Salary Explained Like a 3rd Grader
Want to learn more so you can earn more?
Join Gusto today and get a $100 Visa Gift Card
Visit keepwhatyouearn.com to dive deeper on our episodes
Visit keepwhatyouearncfo.com to work with Shannon and her team
Watch this episode and more here: https://www.youtube.com/channel/UCMlIuZsrllp1Uc_MlhriLvQ
Connect with Shannon on IG: https://www.instagram.com/shannonkweinstein/
The information contained in this podcast is intended for educational purposes only and is not individual tax advice. Please consult a qualified professional before implementing anything you learn.

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