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
260 episodes
If You Owe the IRS Money, Here’s What You Should Know About the Statute of Limitations on Collection
The IRS has a maximum of ten years from the date of assessment to collect tax debts from taxpayers. This period is a crucial timeframe for anyone dealing with tax liabilities, as it essentially defines the duration the IRS can actively pursue d...
Booming or Slowing Down? Why Your 2026 Tax Strategy May Need a Reset
The economy is uneven, and your 2026 tax strategy should reflect your reality. Learn how growing and slowing businesses can adjust tax planning, cash flow, and expenses.
Choosing Between an S Corporation and a C Corporation: It’s About More Than Tax Rates
Choosing between an S corporation and C corporation involves more than tax rates. Learn the key factors that can impact growth and profits.
IRS to Provide Automatic Penalty Relief to Normally Compliant Taxpayers
The IRS has announced that it will begin automatically forgiving certain penalties for taxpayers who have not had a similar penalty in the past three years, rather than requiring them or their tax preparer to request relief for them.
IRS Announces Mid-Year Optional Vehicle Mileage Rate Increase
With gas prices soaring it has been expected the IRS would increase the mileage rate that business owners can deduct for vehicle use instead of keeping a record of actual expenses. Sure enough, the IRS recently announced a 3.5-cent increase in ...
Mid-Year Tax Planning Is Not a Luxury. It’s Where Real Planning Happens.
A mid-year tax review helps business owners improve cash flow, reduce surprises, and make smarter decisions before year-end.
Maximize Pay, Minimize Taxes: A Guide to Fringe Benefits for Employers and Employees
Employers of all sizes can assemble a portfolio of fringe benefits that materially increase employees’ total compensation while delivering tax advantages to both the business and employees.
The Hidden Homeownership Tax: Why Mortgage Shopping Can Be a Smart Financial Move
Many homeowners overpay by not shopping for mortgages. Learn how rates, refinancing, taxes, and cash flow can affect your finances.
What Taxpayers Need to Know About Tokenized Securities and 2026 Tax Reporting
A new Form 1099-DA is being initiated in 2026 for tokenized‑security dispositions. Be ready to supply records if the broker’s basis or other data are missing.
Understanding Social Security: Why Planning Matters More Than Ever
Social Security is about more than choosing when to claim benefits. Learn how taxes, Medicare, spousal benefits, and retirement income planning work together to shape your retirement.
Trump Accounts and Scam Alerts - How to Protect Your Child's Savings
Learn how to identify Trump Account scams, spot warning signs, verify communications, and protect your child's savings from fraudsters.
IRMAA: The Stealth Retirement Tax Many Affluent Retirees Miss
IRMAA can raise Medicare costs for higher-income retirees. Discover planning strategies for Roth conversions, RMDs, and Social Security
Weddings, Childcare, Children’s Summer Employment, and Travel: Navigating Summer’s Tax Minefield
Your tax outcome often depends on facts and dates. A life change that happens in June — marriage, separation, a child taking a summer job, or renting your house during a conference — can determine your filing status, eligibility for credits, an...
You Got the Tax Deduction. But Do You Still Control the Money?
A lawsuit involving a $21 million donor-advised fund is raising new questions about donor rights, charitable giving, and tax planning.
Could Your Dog Qualify for a Tax Break? A New Proposal Says ‘Yes!’
New Jersey's proposed $900 pet tax credit is reigniting debate over whether pet owners should receive tax relief for everyday expenses.
Florida Is Rethinking Property Taxes. Other States Are Watching Closely.
Florida lawmakers are pursuing major property tax changes. Here's why homeowners across the country are paying attention.
Why an IRS Online Account Matters — And How to Create One
An IRS online account offers a faster, more convenient way to manage many tax tasks from your computer or phone — from checking your refund to viewing tax transcripts to setting up payments — without a trip to a post office or an IRS office.
The Businesses Winning Right Now Aren't Better Predictors. They're Better Planners.
CEO confidence just experienced one of its sharpest declines on record. Here's why smart business owners focus less on predicting the economy and more on planning for what comes next.
Trump Accounts Go Live July 4. What to Do Now to Avoid Losing Out
With the federal launch of Trump Accounts scheduled for July 4, 2026, parents and family members who want to jump-start a child’s retirement savings face a rapidly approaching deadline to get accounts activated. But there are still unanswered q...
The Lean Revolution: How AI Is Creating a New Class of Small Business Owners
AI tools are helping entrepreneurs launch and grow businesses faster with lower costs and fewer employees. Learn how small business owners are using AI to stay lean, competitive, and profitable.
Why Your P&L Is Lying to You (And What Your Cash Flow Is Trying to Tell You)
Revenue is up—but cash is tight? Discover why your P&L can mislead you and how expense ratios reveal where your money is really going.
Converting a Rental into Your Home: What You Need to Know About Taxes
Converting a rental into your primary home can be a smart move — both for your living situation and for taxes — but it’s not as simple as move in, sell, and keep the profit.
Game, Set, Tax: The Parent’s Playbook for Sports Expenses, Deductions, and NIL
A child’s and their parent’s sports expenses, from registration fees and travel to equipment and volunteer time, sit at the intersection of personal, medical, charitable and business tax rules. For tax‑minded parents, the key is sorting each co...
Can the IRS See Your Venmo, PayPal, or Cash App Transactions?
Venmo, PayPal, Cash App, Stripe, and other payment apps can create tax reporting obligations for freelancers and small business owners. Learn how Form 1099-K works, what income must be reported, and how to avoid bookkeeping headaches.