deepdive.

Welcome to DeepDive, the podcast where artificial intelligence and industry-leading expertise come together to take you deep into strategies for success in the tax and accounting industry. Each episode dives into important issues and trends, sharing insights about real tax and accounting pros, along with the latest from our CountingWorks Pro blog—all powered by AI for a listening experience you have to hear to believe.

Whether you’re looking to stay on top of industry news or just want to make sense of complex topics, DeepDive is here to keep you on the cutting edge.

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Multiple Side Hustles, One Big Tax Headache

Multiple Side Hustles, One Big Tax Headache

Earning income from TikTok, Shopify, Venmo sales, or freelance gigs? Learn why multiple income streams can complicate your taxes—and how to stay compliant while maximizing deductions.

29 Loka 20259min

Cash Flow vs. Profit: The Hidden Reason Healthy Businesses Struggle

Cash Flow vs. Profit: The Hidden Reason Healthy Businesses Struggle

Even profitable businesses can run short on cash. Learn why cash flow and profit aren’t the same—and how smart planning helps you stay financially strong year-round.

29 Loka 20254min

When Your S-Corp Investment Tanks: Can You Write It Off — and When?

When Your S-Corp Investment Tanks: Can You Write It Off — and When?

Thinking of writing off your S-corp investment? Learn when it’s actually allowed, how to document worthlessness, and what happens if your business rebounds. Plan your next move with expert guidance.

27 Loka 202512min

Beyond the Basics: Unlocking Tax Savings with Deductions Beyond Itemizing

Beyond the Basics: Unlocking Tax Savings with Deductions Beyond Itemizing

In the complex world of tax deductions, understanding the distinctions between above-the-line deductions, below-the-line deductions, and standard and itemized deductions is crucial for effective tax p...

24 Loka 20258min

Tax Advantages of Qualified Charitable Distributions (QCDs)

Tax Advantages of Qualified Charitable Distributions (QCDs)

Qualified Charitable Distributions (QCDs) are a highly effective tool in the tax planning toolkit, particularly for retirees who are required to take Required Minimum Distributions (RMDs) from their I...

24 Loka 20259min

Understanding the Taxation of Lawsuit Settlements: What Taxpayers Need to Know

Understanding the Taxation of Lawsuit Settlements: What Taxpayers Need to Know

Receiving proceeds from a lawsuit settlement can significantly impact your financial situation, and understanding the tax implications is crucial for effective financial planning.

24 Loka 202511min

Maximize Retirement Savings: Don’t Overlook Catch-Up Contributions for Taxpayers Aged 50 and Over.

Maximize Retirement Savings: Don’t Overlook Catch-Up Contributions for Taxpayers Aged 50 and Over.

As retirement approaches, many older Americans seek strategies to maximize their savings and ensure financial stability. Retirement plans often provide "catch-up" contributions, a frequently overlooke...

23 Loka 20259min

Plan Now For the 2027 Revival of Opportunity Zone Investment Tax Breaks

Plan Now For the 2027 Revival of Opportunity Zone Investment Tax Breaks

Considering the forthcoming revival of Opportunity Zone investment tax breaks, taxpayers poised to realize significant capital gains have a unique opportunity to enhance their financial strategies whi...

7 Loka 20254min

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