IRS Cracking Down on Self-Employment Income (Avoid These Mistakes!) episode artwork

EPISODE · Mar 20, 2026 · 7 MIN

IRS Cracking Down on Self-Employment Income (Avoid These Mistakes!)

from Stephen Lee, CPA, CPWA® · host Stephen Lee, CPA, CPWA®

Side Hustle Taxes: 5 Mistakes That Trigger IRS Notices (and How to Avoid Them)CPA Stephen Lee explains why the IRS is paying closer attention to side hustle (self employment) and gig income as platforms and clients send 1099 forms that are automatically matched to tax returns, with mismatches triggering notices like CP2000. He defines side hustle income as any earnings outside a W-2 job (including gig apps, online marketplaces, freelancing, content and affiliate income, and payments via apps) and notes that under IRC Section 61 all such income is taxable, including hobby income. He covers five common mistakes: assuming small amounts don’t matter, waiting for a 1099 before reporting, thinking cash/payment apps are invisible, mixing personal and business finances, and guessing expenses without documentation. He recommends tracking income and expenses, separating accounts, keeping receipts and mileage logs, setting aside tax money, and remembering self-employment tax may apply if net income exceeds $400.00:00 IRS Side Hustle Crackdown00:55 What Counts as Income02:00 Why IRS Notices Happen02:55 Mistake 1 Too Small03:24 Mistake 2 No 109904:04 Mistake 3 App Payments04:36 Mistake 4 Mixed Money05:12 Mistake 5 Guessing Deductions05:38 Real Tax Example06:17 Common Tax Myths06:51 Simple Tracking System07:23 Wrap Up and SubscribeSubscribe for more tips and strategies tailored for business owners and high earning professionals.On this channel, Stephen Lee shares proven strategies to help high earners, business owners, and professionals keep more of what they make, minimize taxes, and build lasting wealth.Whether you’re optimizing your S-Corp, investing smarter, or managing 1099 income, this channel gives you the tools to make confident money moves — backed by real client experience.Subscribe for smart, actionable advice — and take control of your financial future.The information provided on this channel is for general information and entertainment purposes only. It is not intended to serve as legal, financial, or tax advice. You should not act or refrain from acting on the basis of any content included on this channel without seeking appropriate legal, tax, or other professional advice specific to your individual circumstances. The use or reliance on any information contained on this channel is solely at your own risk.

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IRS Cracking Down on Self-Employment Income (Avoid These Mistakes!)

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This episode was published on March 20, 2026.

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Side Hustle Taxes: 5 Mistakes That Trigger IRS Notices (and How to Avoid Them)CPA Stephen Lee explains why the IRS is paying closer attention to side hustle (self employment) and gig income as platforms and clients send 1099 forms that are...

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