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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Episoder(296)

Back-to-School for Your Business: A Mid-Year Financial Report Card

Back-to-School for Your Business: A Mid-Year Financial Report Card

As kids head back to school, give your business a mid-year report card. Discover seven key areas every small business owner should review before year-end.

19 Aug 6min

What Counts as Taxable Income? You Might Be Surprised.

What Counts as Taxable Income? You Might Be Surprised.

Under the Internal Revenue Code Section 61, gross income generally means all income from whatever source derived, and unless a specific rule says it is excluded, it is taxable. In simple terms: if you...

19 Aug 6min

The Tax Law Changed. The Real Story Is What Comes Next.

The Tax Law Changed. The Real Story Is What Comes Next.

Explore Treasury’s 2026 Priority Guidance Plan, OBBBA implementation, regulatory changes, and what evolving IRS guidance could mean for tax planning.

18 Aug 4min

Interest Rates Aren’t Going Back to Zero: A Business Owner’s Guide to Smart Borrowing

Interest Rates Aren’t Going Back to Zero: A Business Owner’s Guide to Smart Borrowing

Interest rates remain elevated, making every borrowing decision more important. Learn when to refinance, finance equipment, lease, or pay down debt—and how tax planning can lower your true cost of cap...

17 Aug 4min

What Caregivers Need to Know About Medicaid Waiver Payments

What Caregivers Need to Know About Medicaid Waiver Payments

Medicaid waiver payments can create unusual tax issues because they sit at the intersection of health care, social services, and the tax code. For many caregivers, these payments are not just compensa...

14 Aug 4min

Cryptocurrency and Taxes: What Everyday Taxpayers Need to Know

Cryptocurrency and Taxes: What Everyday Taxpayers Need to Know

For many taxpayers, cryptocurrency creates more tax issues than expected. You can owe tax even if you never convert your crypto into dollars. You can also have income even if the crypto was given to y...

12 Aug 4min

Prediction Markets Are Becoming a Tax Issue - Here's Why That Matters

Prediction Markets Are Becoming a Tax Issue - Here's Why That Matters

Prediction market taxation is evolving. Learn how new state laws, federal oversight, and changing tax rules could affect investors and future reporting.

12 Aug 4min

Treasury Signals Increased Scrutiny of Sophisticated Tax Investment Strategies: What High-Net-Worth Investors Should Know

Treasury Signals Increased Scrutiny of Sophisticated Tax Investment Strategies: What High-Net-Worth Investors Should Know

Treasury is reviewing sophisticated tax-aware investment strategies. Learn what high-net-worth investors should know before implementing complex tax planning.

7 Aug 4min

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