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)

Unlocking the HSA: A Rare Triple Tax Break for Medical and Retirement Planning

Unlocking the HSA: A Rare Triple Tax Break for Medical and Retirement Planning

A Health Savings Account, or HSA, is one of the most tax-efficient accounts in the Internal Revenue Code. Its basic purpose is simple: to help people with high-deductible health plans save for current...

7 Aug 5min

The IRS Is Updating Its Voluntary Disclosure Program for Cryptocurrency: What Crypto Investors Need to Know

The IRS Is Updating Its Voluntary Disclosure Program for Cryptocurrency: What Crypto Investors Need to Know

The IRS is updating its Voluntary Disclosure Program for cryptocurrency. Learn what it means if you have unreported crypto transactions.

6 Aug 4min

Succession Planning for Business Owners; Protecting Your Company, Your Family and the Tax Outcome

Succession Planning for Business Owners; Protecting Your Company, Your Family and the Tax Outcome

Business succession planning is the process of preparing for the future transfer of a business so that the company can continue operating smoothly while also meeting the owner’s personal, family, and ...

4 Aug 5min

Maximizing Educational Savings: A Comprehensive Guide to Section 529 Plans

Maximizing Educational Savings: A Comprehensive Guide to Section 529 Plans

Learn how 529 plans can help you save for education with tax advantages, flexible contribution options, and strategies for unused funds.

31 Jul 5min

Before You Buy the Equipment, Seek Advice

Before You Buy the Equipment, Seek Advice

Thinking about buying business equipment? Learn why tax planning before you purchase can improve cash flow, financing, and long-term results.

29 Jul 4min

Important Change For Premium Tax Credit Repayments In 2026; What Taxpayers Need Know Now

Important Change For Premium Tax Credit Repayments In 2026; What Taxpayers Need Know Now

Learn how the 2026 premium tax credit repayment changes could increase your tax bill and what steps you can take now to avoid surprises.

28 Jul 5min

Hiring, Layoffs, and Contractors: Payroll Tax Mistakes That Get Expensive Fast

Hiring, Layoffs, and Contractors: Payroll Tax Mistakes That Get Expensive Fast

Workforce changes can create payroll tax nexus, contractor, trust fund tax, reimbursement, and benefits issues. Learn what to review now.

25 Jul 5min

Domicile: What It Means, Why It Matters, and How to Protect Your Tax Position

Domicile: What It Means, Why It Matters, and How to Protect Your Tax Position

Moving or living in two states? Learn how domicile affects state taxes, residency, and audits, plus steps to protect your tax position.

23 Jul 4min

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