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PODCAST · business

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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  1. 238

    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.

  2. 237

    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.

  3. 236

    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.

  4. 235

    No Direct Deposit? Your IRS Refund Could Be Delayed for More Than Two Months

    Received an IRS CP53E notice? Learn why taxpayers who choose paper refund checks may wait more than two months and what you can do to avoid delays.

  5. 234

    Free Retirement Money? Here’s How to Get It

    If you’re saving for retirement and have a modest income, the Saver’s Credit in 2026 or the Saver Match can help you fund your retirement plan.

  6. 233

    Trump Accounts and Gift Tax Returns: How IRS Guidance Changed the Rules for Family Contributions

    IRS Revenue Procedure 2026-25 clarifies when family contributions to Trump accounts qualify for the annual gift tax exclusion and when a gift tax return may still be required. Learn what parents and grandparents need to know.

  7. 232

    Reasonable Compensation Is Not a One-Time Decision

    Reasonable compensation should evolve as your business grows. Learn why S corporation owners should review salary, distributions, and tax planning regularly.

  8. 231

    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 debts. Understanding when this clock starts, potential extensions, and precautionary measures can empower taxpayers to navigate their financial obligations more effectively.

  9. 230

    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.

  10. 229

    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.

  11. 228

    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.

  12. 227

    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 the optional mileage rate for business-use vehicles and a 3 cent increase for medical and moving expenses, effective for the last half of 2026.  

  13. 226

    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.

  14. 225

    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.

  15. 224

    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.

  16. 223

    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.

  17. 222

    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.

  18. 221

    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.

  19. 220

    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

  20. 219

    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, and what income must be reported for the entire year.

  21. 218

    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.

  22. 217

    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.

  23. 216

    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.

  24. 215

    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.

  25. 214

    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.

  26. 213

    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 questions.

  27. 212

    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.

  28. 211

    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.

  29. 210

    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.

  30. 209

    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 cost into the correct box.

  31. 208

    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.

  32. 207

    The Side Hustle Tax Trap Hitting Gen Z

    From Venmo income to freelance gigs and creator revenue, many Gen Z workers are facing unexpected tax bills. Learn how side hustle taxes work and how to avoid common mistakes.

  33. 206

    What Tip-Earning Taxpayers Need to Know under the Tips Deduction Final Regulations

    A new, temporary federal tax break for tip earners went into law for tax years beginning in 2025 and runs through 2028. The change creates a below-the-line deduction for “qualified tips,” but it comes with a number of eligibility rules, reporting requirements, and limits taxpayers need to know.

  34. 205

    The Emergency Savings Crisis Quietly Growing in America

    More Americans are relying on credit cards instead of emergency savings. Learn why financial stress is rising and how small planning habits can improve financial stability.

  35. 204

    Unlocking the Power of Crowdfunding: Navigating Tax Implications and Maximizing Fundraising Success

    Crowdfunding has emerged as a popular method to raise funds for various personal, charitable, and business endeavors. However, with this comes a myriad of tax implications that organizers and contributors must navigate to ensure compliance and minimize liabilities.

  36. 203

    The Economy Feels Uncertain. Here’s What Smart Small Businesses Are Doing Anyway

    Inflation, high interest rates, cautious consumers, and economic uncertainty are putting pressure on small businesses. Learn how smart business owners are adapting, protecting cash flow, and staying resilient.

  37. 202

    Unlocking Healthcare Savings: How HSAs and HDHPs Can Combat Rising Insurance Costs

    In the face of escalating healthcare costs, many individuals and families are seeking innovative strategies to manage expenses effectively. One emerging alternative gaining traction is the combination of Health Savings Accounts (HSAs) and High-Deductible Health Plans (HDHPs).

  38. 201

    Just Starting a New Business? Don’t Overlook Start-Up and Organizational Costs Deductions

    Starting a new business can be expensive, but the tax rules offer relief: certain start‑up and organizational expenses like market research, advertising, training, professional fees and filing costs to form a company may be deductible.

  39. 200

    Sports Betting Isn’t Just Entertainment Anymore — It’s Tax Policy

    States are using sports betting to generate revenue and offset taxes. Here’s how the strategy is growing nationwide.

  40. 199

    Portland’s “Most Hated Tax” Might Be Changing. Here’s What That Actually Means

    Portland plans to raise its arts tax while exempting thousands. Here’s what the proposal means for taxpayers.

  41. 198

    Did You Repay Money You Paid Taxes on in a Prior Year? There is a Solution to Provide Tax Relief.

    If you've found yourself in a situation where you've repaid income that you initially reported as taxable in a prior year, you might be eligible for tax relief through the Claim of Right doctrine.

  42. 197

    Unlocking Tax Savings: Navigating the Complex World of Foreign Travel Deductions

    When engaging in business overseas, it's crucial to understand how travel expenses are treated under U.S. tax law. Unlike domestic travel, where transportation costs are often fully deductible if the trip is "primarily" for business, foreign travel requires a more granular day-by-day calculation to account for personal time. 

  43. 196

    Keeping It in the Family: Tax Risks and Benefits of Home Title Transfers

    A frequently encountered issue is when an elderly parent turns the title of his or her home over to a child or other beneficiary and continues to reside in the home, thinking that it is the correct thing to do, but without considering the tax repercussions.

  44. 195

    Foreign Earned Income Exclusion: Navigating the Opportunities

    The Foreign Earned Income Exclusion (FEIE) is a valuable tax provision for U.S. citizens and resident aliens living and working abroad. It allows eligible taxpayers to exclude a certain amount of foreign earned income and housing costs from U.S. taxation.

  45. 194

    Why December 31,2026 is a Make-or-Break Date for Original QOF Investors

    If you invested in a Qualified Opportunity Fund (QOF) using deferred capital gains, pay attention: the law requires that deferred gains be included in income no later than December 31, 2026. That deadline is real, unavoidable unless Congress or the IRS provides relief, and it can mean a large, unexpected tax bill even if your fund hasn’t paid you a dime.

  46. 193

    Tens of Millions Claimed New Tax Breaks — Did You Miss One?

    Early 2025 tax returns filing data indicates substantial use of the new tax law’s signature middle‑class tax changes, and the average refund rose compared with last year. However, polling suggests room remains to improve taxpayer awareness and not all eligible people, especially those with tip and overtime pay, took full advantage of the new law.

  47. 192

    Where Is My Refund? What To Do When Your Refund Is Way Overdue (And Why a New IRS Notice Might Be The Reason)

    If your federal tax refund is seriously overdue, it’s normal to feel worried — especially if you were counting on that money for bills or other expenses. Before panic sets in, here’s a clear, practical guide explaining what may be happening, why a new IRS administrative change could be the culprit, and exactly what steps you should take now.

  48. 191

    Struggling to Pay Your Taxes? Here Are Solutions and Guidance

    Individuals have many options when they cannot pay their tax liability, including setting up an IRS payment plan, tapping a retirement plan, acquiring a home equity loan and borrowing money from a friend or relative. Each option has negative implications, and some have substantial fees, penalties and/or interest.

  49. 190

    The Real Cost of Hiring (It’s Not Just Salary Anymore)

    Think you can afford a new hire? The true cost goes far beyond salary. Learn how to evaluate hiring decisions and avoid costly mistakes for your business.

  50. 189

    Gen Z Is Earning Differently—And Most Are Getting Taxes Wrong

    From side hustles to creator income, Gen Z is earning in new ways—but missing key tax rules. Learn the most common mistakes and how to avoid them early.

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ABOUT THIS SHOW

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.

HOSTED BY

CountingWorks PRO Marketing Team

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Frequently Asked Questions

How many episodes does deepdive. have?

deepdive. currently has 50 episodes available on PodParley. New episodes are automatically indexed when they're published to the podcast feed.

What is deepdive. about?

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,...

How often does deepdive. release new episodes?

deepdive. has 50 episodes. Check the episode list to see recent publication dates and frequency.

Where can I listen to deepdive.?

You can listen to deepdive. on PodParley by clicking any episode. We provide an embedded audio player for direct listening, and you can also subscribe via your preferred podcast app using the RSS feed.

Who hosts deepdive.?

deepdive. is created and hosted by CountingWorks PRO Marketing Team.
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