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.
Episodes
290 episodes
New Retirement Plan Rule for Long-Term Care Premiums
A new rule may let eligible taxpayers use retirement funds to pay qualified long-term care insurance premiums without the 10% early-withdrawal penalty.
When You Become the Family CFO
Supporting children, helping aging parents, and protecting your own retirement can turn you into the family CFO. Here’s how to manage the financial overlap.
Why Self-Employed Taxpayers Must Keep Better Records for Travel, Vehicle, and Other Business Expenses
Business expenses can reduce taxable income, but many learn too late that a deduction is only as good as the records behind it.
Pay Off Debt or Invest? How Higher Interest Rates Change the Math
Should you pay off debt or invest? Higher interest rates have shifted the balance. Learn how to evaluate high-interest debt, emergency savings, retirement planning, and taxes when making important financial decisions.
What Every Executor (Personal Representative) Should Know About Personal Liability For a Decedent’s Taxes
An executor of a decedent’s estate must administer the estate and distribute assets in the statutory order of priority; failure to follow those legal requirements can expose the executor to personal liability.
September 15 Is the Third Quarter Estimated Tax Deadline
If you make or receive income that is not fully covered by withholding, September 15, 2026, is an important date on the tax calendar. It is the due date for the third installment of 2026 federal estimated tax payments for individuals who are no...
The 10-Year Retirement Countdown: What to Do Differently at 50, 55, and 60
Your final decade before retirement can have the biggest impact on your financial future. Learn the key planning opportunities at ages 50, 55, and 60—and why proactive tax planning matters.
Donating Appreciated Stock Is One of the Most Tax‑Efficient Charitable Gifts
Donating long‑term appreciated stock (publicly traded shares held for more than one year) to a qualified charity is a high‑impact way for donors to support causes while obtaining favorable tax treatment.
Inheriting an IRA: A Guide for Taxpayers
If you inherited a Traditional IRA after 2019, the rules are not always what people expect. The SECURE Act changed the way many inherited retirement accounts must be paid out, and now who inherited the account and whether the original owner had...
The Holiday Rush Starts Now: 7 Financial Moves Businesses Should Make Before Q4
The holiday season starts earlier than many business owners realize. Discover seven proactive financial moves to strengthen cash flow, manage inventory, and optimize taxes before Q4.
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.
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 got something of value and the tax law does...
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.
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 capital.
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 compensation for providing daily care; they can also...
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 you “for free.” And if you do not keep good r...
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.
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.
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 and future medical costs with favorable tax...
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 whatit means if you have unreported crypto transactions.
Succession Planning for Business Owners; Protecting Your Company, Your Family and the Tax Outcome
Business succession planning is the process of preparing for the futuretransfer of a business so that the company can continue operating smoothly whilealso meeting the owner’s personal, family, and financial goals.
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.
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.