The 1099 Rules Every Small Business Owner Needs to Know Before January 31
Small Business Tax Savings Podcast
Biggest 1099 Mistakes to Avoid
Mike highlights missing W-9s and messy bookkeeping as primary causes of late filings and penalties.
Are you still guessing when it comes to 1099s? Most business owners are. And every January, that confusion turns into stress, penalties, and last-minute cleanup that could have been avoided.
In this episode, Mike Jesowshek breaks down everything small business owners need to know about 1099-NEC and 1099-MISC forms, who needs one, who doesn't, the deadlines and the penalties that add up fast.
If you want January to feel calm instead of chaotic, this episode gives you the clear rules and simple process to get compliant without overthinking it.
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Chapters
(01:00) What is a 1099?
Mike explains how 1099s work, why the IRS requires them, and how they are used to match income across businesses and contractors.
(02:12) 1099-NEC vs 1099-MISC
Which form applies to contractors, which applies to rent, and why mixing them up creates problems.
(03:30) The Real 1099 Deadlines
Why January 31 matters, how weekends affect filing dates, and what business owners must send and file by the deadline.
(04:55) IRS Penalties That Add Up Fast
Late filing penalties, intentional disregard penalties, and how missing multiple forms can quickly turn into thousands of dollars owed.
(06:40) Who Actually Needs a 1099
The $600 cumulative rule, common misunderstandings, and why splitting payments does not avoid filing requirements.
(08:20) Common Exceptions Most Owners Miss
When corporations, payment processors, foreign contractors, employees, and personal payments do not require a 1099.
(10:15) Why Credit Card Payments Change Everything
How payment processors issue 1099-Ks and why that removes your filing obligation.
(11:30) The 4-Step Process to File 1099s Correctly
Collect W-9s, prepare the forms, send copies to recipients, and file with the IRS the right way.
(13:05) The Biggest 1099 Mistakes
Why missing W-9s and messy bookkeeping cause late filings and penalties every year.
(14:45) How Software Simplifies the Entire Process
Why e-filing tools save time, reduce errors, and make year-over-year filing easier.
(15:40) The 2026 Rule Change Every Business Owner Should Know
The new $2,000 filing threshold, inflation adjustments, and how this change affects future planning.
Podcast Host:
Mike Jesowshek, CPA โ Founder and Host of Small Business Tax Savings Podcast
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๐ ABOUT THE PODCAST
The Small Business Tax Savings Podcast is your go-to resource for cutting-edge tax strategies to help entrepreneurs legally slash their tax bills. Hosted by Mike Jesowshek, CPA, this show breaks down complex tax topics into clear, no-fluff insights so you can keep more of your hard-earned money.
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