What happens when college athletes suddenly start earning six- and seven-figure NIL deals?

In this episode of Two Accountants Talking Sh*t, Mike and Gary break down the rapidly evolving world of Name, Image, and Likeness (NIL) agreements and the tax implications many student-athletes never see coming.

The conversation explores how NIL income can effectively turn college athletes into business owners overnight, often without proper tax planning, withholding, or financial education. Mike and Gary explain why NIL earnings are often subject to self-employment tax, how athletes may be able to deduct legitimate business expenses such as training, coaching, travel, and marketing, and why forming an LLC or other business entity may help support long-term financial goals.

They also discuss the growing complexity of multi-state taxation as athletes travel for appearances, endorsements, camps, and promotional events. Many athletes may owe taxes in multiple states, creating additional filing requirements and potential surprises at tax time.

Beyond taxes, the hosts examine the broader economics of college sports, including whether state income tax rates could influence recruiting decisions and how schools in no-income-tax states may gain a competitive advantage in the NIL era.

Topics covered include:

• NIL tax basics for college athletes
• Self-employment tax explained
• LLCs and business entities for athletes
• Tax deductions for NIL income
• Multi-state tax filing issues
• Royalty income vs. earned income
• NCAA and NIL financial planning
• How taxes could impact recruiting
• The future of NIL legislation and tax law

This episode is essential listening for student-athletes, parents, sports agents, college recruiters, coaches, and anyone trying to understand the business side of modern college athletics.

Whether you're a college athlete, parent, coach, creator, or entrepreneur, this episode explains the business side of NIL in plain English.

Because that NIL check might feel exciting... until tax season shows up.

In this episode of Two Accountants Talking Sh*t, Gary and Mike sit down with Grant Lang, a seasoned contractor and lifelong entrepreneur with more than 40 years of business experience.

From roofing and dumpster companies to restaurants and poker tournaments, Grant shares unfiltered stories about building businesses, learning hard lessons, and navigating costly tax mistakes along the way.

Together, they discuss what happens when business owners don't understand their tax obligations, why so many contractors get blindsided by the IRS, and how a little planning can save thousands of dollars.

WHAT YOU'LL LEARN

• Why many new business owners are shocked by their first tax bill

• The importance of setting aside money for taxes throughout the year

• Why quarterly estimated tax payments matter

• How poor tax planning turns into expensive tax problems

• Common tax mistakes contractors and self-employed professionals make

• When an LLC or S-Corp may help reduce taxes and protect assets

• Frequently missed business deductions and write-offs

• Common IRS audit red flags every entrepreneur should know

KEY MOMENTS

• Grant's surprise tax bill after a successful business year

• The $22,000 IRS bill caused by an unreported gambling win

• Building and franchising a valet business as a teenager

• Navigating the challenges of the dumpster industry

• Creating multiple successful businesses without ever having a traditional W-2 job

GUEST SPOTLIGHT: GRANT LANG

Grant Lang is a lifelong entrepreneur with more than four decades of experience in construction, roofing, waste management, hospitality, and business ownership.

His journey highlights the reality many entrepreneurs face: learning through experience, making mistakes, adapting quickly, and continuing to grow.

If you're a contractor, freelancer, or business owner:

• Treat yourself like a business

• Work with a proactive tax professional, not just a tax preparer

• Plan ahead instead of reacting at tax time

• Remember: the IRS always gets paid—make sure you're prepared

CONNECT & FOLLOW

Instagram:
https://www.instagram.com/twoaccountantspodcast

TikTok:
https://www.tiktok.com/@twoaccountantspodcast

YouTube:
https://www.youtube.com/@TwoAccountantsPodcast

Listen on Apple Podcasts, Spotify, Amazon Music, iHeartRadio, or wherever you get your podcasts.

DISCLAIMER

The information discussed in this podcast is provided for educational, informational, and entertainment purposes only and should not be considered tax, legal, accounting, or financial advice.

Every tax situation is unique. Before making any financial, tax, or business decisions, consult with a qualified tax professional, CPA, attorney, or financial advisor regarding your specific circumstances.

Views and opinions expressed by guests are their own and do not necessarily reflect those of the hosts, producers, or affiliated organizations.

For personalized tax guidance, contact 1-800Accountant or another qualified tax professional.

In this episode of Two Accountants Talking Sh*t, 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 $200 million in revenue, with media exposure valued at more than $1 billion, 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 $10,000 to $40,000, 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.

Like the podcast?

Share it with a friend and leave a positive review. It helps more people find the show.