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It’s 1099 Time: Here’s Your Checklist for Stress-Free Filing
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In this episode of the Sunlight Tax Podcast, I break down everything self-employed business owners need to know about 1099s – what they are, why they matter, and what’s changed under current 1099 reporting rules. If you work with independent contractors, I walk you through a clear, step-by-step 1099 checklist to help you file correctly and on time. We cover why accurate bookkeeping is important, when and why to collect W-9 forms, and how to avoid common 1099 mistakes that can trigger IRS penalties.
I also explain the different types of 1099 forms (including which ones apply to freelancers and small businesses), what each form is used for, and the penalties for failing to file or filing incorrectly.
Listen and Subscribe Here
In this episode of the Sunlight Tax Podcast, I break down everything self-employed business owners need to know about 1099s – what they are, why they matter, and what’s changed under current 1099 reporting rules. If you work with independent contractors, I walk you through a clear, step-by-step 1099 checklist to help you file correctly and on time. We cover why accurate bookkeeping is important, when and why to collect W-9 forms, and how to avoid common 1099 mistakes that can trigger IRS penalties.
I also explain the different types of 1099 forms (including which ones apply to freelancers and small businesses), what each form is used for, and the penalties for failing to file or filing incorrectly.
Also mentioned in today’s episode:
01:00 Understanding 1099: The Basics
04:31 The Importance of 1099s
10:53 The kinds of 1099s you are going to be dealing with
18:20 Checklist for Issuing 1099s
25:45 Other Resources for filing 1099s
If you enjoyed this episode, please rate, review and share it!
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Links:
Get my 1-hour course: All About 1099s
Join my free class: Make Taxes Easier and Stash an Extra $152k in Your Savings
Check out my program, Money Bootcamp
Order my book, Taxes for Humans: Simplify Your Taxes and Change the World When You’re Self-Employed
Healthcare Changes From the OBBBA: Expert Dr. Matthew Fiedler Explains
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In this episode of the Sunlight Tax Podcast, I talk with Dr. Matthew Fiedler about the new One Big Beautiful Bill Act—and what it could mean for your healthcare and taxes.
We break down how the government shutdown affects healthcare access, why there are major Medicaid cuts, and what trade-offs come with the new tax cuts. The conversation highlights the challenges faced by low and moderate-income individuals in accessing healthcare, especially in light of new administrative requirements and potential loss of coverage.
We also talk about what this means if you’re self-employed or run a small business. With shifting healthcare policies and tax laws, good bookkeeping and clear financial records matter more than ever.
Dr. Fiedler emphasizes the need for a more rational approach to healthcare financing and the importance of bookkeeping for self-employed individuals.
Listen and Subscribe Here
In this episode of the Sunlight Tax Podcast, I talk with Dr. Matthew Fiedler about the new One Big Beautiful Bill Act, and what it could mean for your healthcare and taxes.
We break down how the government shutdown affects healthcare access, why there are major Medicaid cuts, and what trade-offs come with the new tax cuts. The conversation highlights the challenges faced by low and moderate-income individuals in accessing healthcare, especially in light of new administrative requirements and potential loss of coverage.
We also talk about what this means if you’re self-employed or run a small business. With shifting healthcare policies and tax laws, good bookkeeping and clear financial records matter more than ever.
Dr. Fiedler emphasizes the need for a more rational approach to healthcare financing and the importance of bookkeeping for self-employed individuals.
Also mentioned in this episode:
01:46 Understanding the One Big Beautiful Bill Act
03:07 Impact of Government Shutdown on Healthcare
08:05 Overview of Healthcare Provisions in the Bill
09:30 Trade-offs in Tax Cuts and Healthcare Funding
12:20 Medicaid Cuts and Work Requirements
16:00 Navigating Medicaid for the Recently Unemployed
20:16 Cost-Shifting from Federal to State Medicaid Programs
25:29 Consequences for Low and Moderate Income Individuals
28:18 Changes in Marketplace Coverage Requirements
30:38 Implications for Self-Employed Individuals
If you enjoyed this episode, please rate, review and share it!
Every review makes a difference by telling Apple or Spotify to show the Sunlight Tax podcast to new audiences.
Links:
Link to pre-order my book, Taxes for Humans: Simplify Your Taxes and Change the World When You’re Self-Employed.
Link to pre-order my workbook, Taxes for Humans: The Workbook
How OBBBA Changes Medicaid, Planned Parenthood, Health Subsidies and Access for Immigrants
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In this episode of The Sunlight Tax Podcast, I’m unpacking the One Big Beautiful Bill Act (OBBBA) and what its sweeping health care changes mean for real people and families. We’ll dig into how this new legislation affects Medicaid coverage, Planned Parenthood funding, and low-income immigrants, plus what’s changing for marketplace insurance subsidies and health savings accounts (HSAs).
I’ll also share key insights from an excellent healthinsurance.org article by Louise Norris, titled “One Big Beautiful Bill Act Brings Sweeping Changes to Health Coverage.” With her permission, I’ll be reading excerpts from that piece and you can find the full article linked in the show notes. It’s a must-read if you want a deeper understanding of how the One Big Beautiful Bill Act (OBBBA) could reshape American health care and insurance coverage in the years ahead.
Listen and Subscribe Here
In this episode of The Sunlight Tax Podcast, I’m unpacking the One Big Beautiful Bill Act (OBBBA) and what its sweeping health care changes mean for real people and families. We’ll dig into how this new legislation affects Medicaid coverage, Planned Parenthood funding, and low-income immigrants, plus what’s changing for marketplace insurance subsidies and health savings accounts (HSAs).
I’ll also share key insights from an excellent healthinsurance.org article by Louise Norris, titled “One Big Beautiful Bill Act Brings Sweeping Changes to Health Coverage.” With her permission, I’ll be reading excerpts from that piece and you can find the full article linked in the show notes. It’s a must-read if you want a deeper understanding of how the One Big Beautiful Bill Act (OBBBA) could reshape American health care and insurance coverage in the years ahead.
Also mentioned in this episode:
03:29 Health Care Provisions Overview
07:02 Medicaid Changes and Impacts
09:17 Planned Parenthood Funding
11:37 Subsidy Eligibility for Low-Income Immigrants
12:32 Impact of Subsidy Changes on Self-Employed
17:09 Health Savings Accounts and Marketplace Plans
If you enjoyed this episode, please rate, review and share it!
Every review makes a difference by telling Apple or Spotify to show the Sunlight Tax podcast to new audiences.
Credit:
Key insights in this episode come from an excellent article by Louise Norris for healthinsurance.org, titled “One Big Beautiful Bill Act Brings Sweeping Changes to Health Coverage.” Shared with permission.
Links:
Article by Louise Norris published in healthinsurance.org: One Big Beautiful Bill Act brings sweeping changes to health coverage by Louise Norris
Join my free class: Make Taxes Easier and Stash an Extra $152k in Your Savings
Check out my program, Money Bootcamp
Link to pre-order my book, Taxes for Humans: Simplify Your Taxes and Change the World When You’re Self-Employed.
Link to pre-order my workbook, Taxes for Humans: The Workbook
OBBBA Reveals Why Tax Laws for the 1% Happen, and A Solution
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In this episode of the Sunlight Tax Podcast, I’m diving into the One Big Beautiful Act, a major tax law that passed this summer. I found a great, nonpartisan article from the Tax Policy Center Urban Institute & Brookings Institution, and with the authors’ permission, I’m going to share it with you here. It’s called “When Tax Laws Defy Public Opinion: What OBBBA Reveals.”
The piece lays out the short-term wins of this law, but also the long-term effects on things like healthcare and our social safety net. What really struck me is the gap between what people want and what lawmakers actually do—and how much wealth drives those decisions.
For me, the big lesson is that we need to frame fiscal issues in ways that connect with the public, and ultimately, push for campaign finance reform to get legislation that reflects real public priorities.
Listen and Subscribe Here
In this episode of the Sunlight Tax Podcast, I’m diving into the One Big Beautiful Act, a major tax law that passed this summer. I found a great, nonpartisan article from the Tax Policy Center Urban Institute & Brookings Institution, and with the authors’ permission, I’m going to share it with you here. It’s called “When Tax Laws Defy Public Opinion: What OBBBA Reveals.”
The piece lays out the short-term wins of this law, but also the long-term effects on things like healthcare and our social safety net. What really struck me is the gap between what people want and what lawmakers actually do—and how much wealth drives those decisions.
For me, the big lesson is that we need to frame fiscal issues in ways that connect with the public, and ultimately, push for campaign finance reform to get legislation that reflects real public priorities.
Also mentioned in this episode:
01:05 Introduction to the One Big Beautiful Bill Act
02:34 The Societal Impact of the Tax Bill
04:44 Public Opinion vs. Legislative Action
07:29 Disparities in Wealth and Policy Preferences
10:31 The Importance of Campaign Finance Reform
If you enjoyed this episode, please rate, review and share it!
Every review makes a difference by telling Apple or Spotify to show the Sunlight Tax podcast to new audiences.
Links:
Tax Policy Center Urban Institute & Brookings Institution Article: When Tax Laws Defy Public Opinion: What OBBBA Reveals
Join my free class: Make Taxes Easier and Stash an Extra $152k in Your Savings
Check out my program, Money Bootcamp
Link to pre-order my book, Taxes for Humans: Simplify Your Taxes and Change the World When You’re Self-Employed.
Link to pre-order my workbook, Taxes for Humans: The Workbook
Student Loan Updates: Borrowing Limits and Repayment Plans Under the New Tax Bill
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I’m diving into the One Big Beautiful Bill Act and how it impacts student loan borrowers. This new legislation introduces changes to borrowing limits, updates to repayment plans, and raises important questions for legacy borrowers still managing older loans.
If you’ve been wondering how these updates affect your education financing or what steps you should take to prepare, you’re in the right place. My goal is to provide clear explanations and practical resources so you can confidently navigate the new student loan rules under this tax law.
Listen and Subscribe Here
I’m diving into the One Big Beautiful Bill Act and how it impacts student loan borrowers. This new legislation introduces changes to borrowing limits, updates to repayment plans, and raises important questions for legacy borrowers still managing older loans.
If you’ve been wondering how these updates affect your education financing or what steps you should take to prepare, you’re in the right place. My goal is to provide clear explanations and practical resources so you can confidently navigate the new student loan rules under this tax law.
Also mentioned in today’s episode:
01:00 Introduction to the One Big Beautiful Bill Act
06:42 New Borrowing Caps and Repayment Plans
13:31 Navigating Legacy Borrower Challenges
Takeaways
The One Big Beautiful Bill Act is significant legislation to focus on.
New student loan borrowers will have only two repayment options after July 2026.
The SAVE program is ending, impacting many borrowers.
New lifetime caps on borrowing for education will be implemented.
Half a million borrowers may see increased payments due to changes.
Low and middle-income students may struggle with graduate school costs.
The RAP plan offers more flexible repayment options for borrowers.
It's crucial to stay informed through reliable resources and articles.
Navigating student loans requires careful consideration and action.
If you enjoyed this episode, please rate, review and share it!
Every review makes a difference by telling Apple or Spotify to show the Sunlight Tax podcast to new audiences.
Other Sunlight Tax podcast episodes about OBBBA:
Unpacking Trump’s New Tax Law: What You Need to Know About the One Big Beautiful Bill Act
Breaking Down Trump’s New Tax Law: Cars, New Loan Interest Deduction, and Expiring Energy Credits
New Tax Bill: No Tax on Tips, No Tax on Overtime, and New Deduction for Seniors
Links:
Help article by Tara Siegel Bernard from the New York Times
This article on the NPR website, by Cory Turner
Link to pre-order my book, Taxes for Humans: Simplify Your Taxes and Change the World When You’re Self-Employed.
Link to pre-order my workbook, Taxes for Humans: The Workbook
Get your free visual guide to tax deductions
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