In this episode of Two Accountants Talking Sht*, Gary and Mike break down complex tax topics in a way that’s clear, practical, and entertaining. From Coachella’s billion-dollar economic impact to hidden tax risks for influencers, athletes, entrepreneurs, and high earners, this conversation changes the way business owners and creators should think about money and taxes.
The biggest takeaway?
If you’re making money outside of a traditional paycheck — whether as a freelancer, creator, contractor, side hustler, or entrepreneur — the IRS considers you a business, and you need to operate like one.
What You’ll Learn
Why “Everyone Is a Business”
If you earn income outside of a W-2 job, the IRS treats that income like business income — and your tax strategy should reflect it.
The Real Economics of Coachella
Coachella generates an estimated $200M in revenue, with media exposure valued at more than $1B, creating huge financial opportunities — and major tax implications.
How Taxes Impact High Earners
A massive payday can shrink quickly once federal and state taxes are applied, especially in high-tax states like California.
What Is the “Jock Tax”?
Athletes, entertainers, and performers can owe taxes in every state where they work — not just where they live.
Influencer Tax Risks
Many creators don’t realize they may need to file taxes in multiple states depending on where income is earned.
Maximizing Deductions
Tracking legitimate business expenses is one of the most important ways to reduce taxable income.
SALT Deduction Changes
The State and Local Tax (SALT) deduction cap increased from $10K to $40K, potentially changing tax planning strategies for many earners.
Why Estimated Taxes Matter
Quarterly tax payments are required for many self-employed earners, and missing them can trigger penalties and interest.
Extensions Don’t Delay Payment
Filing an extension gives you more time to file your return — not more time to pay taxes owed.
Key Takeaway
Whether you’re an artist, entrepreneur, influencer, freelancer, contractor, or side hustler, understanding how taxes work — and treating your income like a real business — can help you avoid expensive mistakes.
Who This Episode Is For
Small business owners
Entrepreneurs
Freelancers
Influencers and creators
Gig workers
Side hustlers
Independent contractors
Anyone earning income outside a traditional 9-to-5 job
About the Hosts
Gary Milkwick
Gary Milkwick is the Chief Financial Officer at 1-800Accountant and a CPA specializing in tax strategy and small business operations. He previously worked at PwC and holds an MBA from UCLA Anderson School of Management and a Master of Accountancy from Brigham Young University.
Mike Savage
Mike Savage is the Founder and CEO of 1-800Accountant, a tech-enabled accounting firm helping small businesses simplify bookkeeping, taxes, and financial management through virtual services and flat-rate pricing. He began his career at PwC and was recognized as a Glassdoor Top CEO in 2018.
Disclaimer
This podcast is for informational and entertainment purposes only and does not constitute tax, legal, or financial advice. For advice specific to your situation, consult a qualified tax professional or contact 1-800Accountant.
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