PODCAST · business
deepdive.
by CountingWorks PRO Marketing Team
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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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.
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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.
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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.
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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.
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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.
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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.
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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.
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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.
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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.
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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.
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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.
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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.
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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.
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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.
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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.
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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.
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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.
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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.
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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
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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.
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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.
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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.
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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.
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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.
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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.
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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.
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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.
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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.
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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.
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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.
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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.
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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.
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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.
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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.
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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.
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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.
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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).
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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.
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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.
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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.
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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.
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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.
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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.
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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.
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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.
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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.
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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.
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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.
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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.
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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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