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

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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.