deepdive.
by CountingWorks PRO Marketing Team
Latest episode
New 2026 Tax Benefits for Teachers & Educators: Expanded Deductions…
New 2026 Tax Benefits for Teachers & Educators: Expanded Deductions…
About this podcast
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
The newest 50 of 330 episodes
- New 2026 Tax Benefits for Teachers & Educators: Expanded Deductions for Classroom and Athletic Expenses · 5 minDiscover new 2026 tax deductions for teachers, coaches, and early childhood educators, including the $350 educator deduction and expanded itemized deductions.
- How Far in Advance Should You Prepare a Business for Sale? · 5 minPlanning to sell your business? Learn why preparation should start 3–5 years ahead, including QSBS tax benefits, financial cleanup, and exit planning.
- Is Your Business Really Profitable? 5 Numbers Every Owner Should Know · 5 minRevenue is growing, but are you making money? Discover 5 financial numbers every small-business owner should track to improve profit and cash flow.
- Paying Taxes by Credit Card? New IRS Rules and Costs Explained · 5 minNew IRS regulations expand the framework for direct credit and debit card tax payments. Learn how processing fees, interest, rewards, and payment timing could affect your decision.
- Year-End Stock Portfolio Planning: Steps to Consider Before December 31 · 5 minReview year-end stock portfolio tax strategies, including capital gains, tax-loss harvesting, wash-sale rules, charitable giving, and estimated taxes.
- What Is a Quality of Earnings (QoE) Report, and Do You Need One? · 4 minBuying or selling a business? Learn what a QoE report reveals, how it affects business value, and when new SBA rules require one.
- Have an Adoption Credit Carryover? You May Be Due a 2025 Refund · 4 minThe IRS is issuing refunds to eligible taxpayers with adoption credit carryovers from 2020–2024. Learn who may qualify and whether action is needed.
- Charitable Giving Strategies: Turning Generosity Into Effective Tax Planning · 5 minCharitable giving can do more than support causes you care about. Strategies involving appreciated stock, QCDs, bunching and donor-advised funds may also provide valuable tax…
- Employee Stock Options: When to Exercise, Sell, or Hold to Minimize Taxes · 5 minEmployee stock options can build wealth, but exercising them can also trigger taxes and investment risk. Learn how NSOs and ISOs differ and what to consider before you exercise…
- Congress May Not Be Done With Taxes Yet: What to Watch in the Lame-Duck Session · 5 minCongress could consider targeted tax changes during the 2026 lame-duck session. See what taxpayers and businesses should watch for before year-end.
- The IRS Has a New Mobile App: What Taxpayers Should Know · 6 minThe IRS has replaced IRS2Go with a new mobile app. Learn how to check refunds, view notices, access tax records, make payments, and avoid scams.
- IRS Warns Taxpayers About Fake Tax Credit Promotions · 4 minThe IRS is warning taxpayers about fake tax credits sold through convincing promotions. Learn the warning signs and why independent verification matters before you invest or file.
- EBITDA Isn't the Whole Story: What Buyers and Lenders Really Want to Understand · 5 minEBITDA is only part of the picture. Learn how cash flow, customer concentration, owner dependence, and financial records influence buyers and lenders.
- The Paid Family and Medical Leave Credit: A Valuable Tax Break for Employers · 5 minOffering paid family and medical leave may come with a federal tax benefit. Learn how the now-permanent credit works, which employees qualify, and what employers need to claim it.
- Is Your Loan Interest Tax Deductible? Here's What You Should Know · 5 minIs the interest on your loan tax-deductible? The answer often depends on how you use the borrowed money, not just the type of loan. Learn how these rules affect the deductibility…
- New Car Loan Interest Deduction: What Vehicle Buyers Need to Know · 5 minFinanced a new vehicle? You may qualify for a federal deduction of up to $10,000 in loan interest. Learn which vehicles qualify, income limits, and what records to keep.
- Buying a Business? What the Numbers Should Tell You Before You Make an Offer · 4 minBuying an established business can give you a head start, but you are also buying its financial history. Know what the numbers reveal about earnings, cash flow, customers, debt…
- Accountable Plans: The Tax-Smart Way to Reimburse Employees · 6 minLearn how accountable plans allow businesses to reimburse employee expenses without creating taxable wages and the IRS requirements that must be followed.
- Why Clean Financial Statements Matter When Selling a Business · 5 minClean financial statements can build buyer confidence, support due diligence, and help prevent financial surprises when selling your business.
- Crowdfunding and Taxes: What Organizers and Contributors Need to Know · 5 minCrowdfunding can have unexpected tax consequences. Learn how personal donations, rewards, investments, Form 1099-K, and gift tax rules may apply.
- Thinking About Selling Your Business? Start Preparing Your Financials Now · 5 minPlanning to sell your business? Clean financial records can build buyer confidence, support financing, and help you prepare for due diligence.
- A New Way to Support K–12 Education and Get a Tax Break · 6 minA new federal tax credit begins in 2027 for qualifying K-12 scholarship donations. Learn how the $1,700 credit works, why state participation matters, and what donors should know…
- What Happens If the IRS Says It Never Received Your Tax Return? · 5 minLearn what to do if the IRS says your tax return was never received, including how to verify filing, respond to notices, and protect a refund.
- Supreme Court Decision Means IRS May Pursue Tax Cases ‘Forever’ in Some Fraud Cases · 5 minA Supreme Court decision left in place a ruling allowing the IRS to assess tax indefinitely when return fraud is committed by a tax preparer.
- Why Cash Payments Over $10,000 Can Create Tax Trouble for Business Owners · 5 minDoes your business accept large cash payments? Receiving more than $10,000 can trigger Form 8300 reporting requirements. Learn what counts as cash, key deadlines, and why…
- Five Retirement Tax Moves to Review Before December 31 · 5 minRoth conversions, RMDs, and the senior deduction can affect your 2026 taxes. Review five retirement tax moves to consider before December 31.
- Elder Fraud: How Scammers Target Older Adults and How to Stay Safe · 6 minLearn how scammers target older adults through fraud schemes and discover warning signs, prevention tips, and steps to protect finances.
- Can Your Limited Partner Status Really Shield You from SE Tax? · 4 minRecent court rulings have complicated self-employment tax rules for limited partners. Learn why a partner's role, authority, and structure matter.
- Crypto Investors: That “IRS Digital Asset Compliance Portal” Letter May Be a Scam · 5 minCrypto investors are being targeted with official-looking IRS letters directing them to a fake digital asset portal. Learn the warning signs before sharing wallet or tax…
- BOI Reporting Is Over for U.S. Companies — But Don't Delete Every Compliance Checklist Yet · 6 minFinCEN has permanently ended federal BOI reporting for U.S. companies. Learn what changed, what records to keep, and which entities may still have obligations.
- Why Roth Conversions Can Be a Taxpayer's Secret Weapon · 4 minLearn how Roth conversions work, when they may offer tax advantages, and how tax brackets, RMDs, IRA basis, and other factors can affect the decision.
- Should You Use a PLESA Account If Your Employer Offers One? · 4 minLearn how PLESA accounts work, who may benefit, contribution limits, and why this SECURE 2.0 emergency savings option may help workers.
- PayPal, Venmo and Other Payment Platforms: What the Final Backup-Withholding Rules Mean for Businesses · 5 minTreasury and the IRS finalized backup-withholding rules for third-party payment networks. Learn what the $20,000 and 200-transaction thresholds do—and don't—mean.
- Financial Flexing: When Looking Rich Keeps You From Getting Rich · 4 minFinancial flexing can make expensive spending feel normal. Learn how social media, lifestyle pressure, and easy credit can quietly interfere with long-term financial goals.
- Disaster Tax Relief Just Changed: What Every Taxpayer Must Know · 6 minNew federal disaster tax rules may affect casualty losses and wildfire relief payments. Learn what changed and who may qualify.
- Cash Is Back at the Top of the CFO Agenda — Five Numbers Business Owners Should Be Watching · 5 minA 2026 CFO survey shows cash management is a top finance priority. Here are five cash-flow metrics business owners should monitor before problems appear.
- Don't Wait Until the Last Minute: October 15 is the Extended Due Date for 2025 Individual Tax Returns · 5 minThe October 15, 2026 deadline is approaching for extended 2025 tax returns. Learn why early filing and complete documents matter.
- Life Insurance Tax Issues Every Taxpayer Should Know · 5 minLearn how life insurance can affect taxes, including cash value growth, MEC rules, policy loans, life settlements, and accelerated death benefits.
- States Using Taxpayer Dollars to Fund College Sports · 5 minAs college athletic departments face rising costs and multimillion-dollar athlete payments, some states are using tax revenue and public funds to help schools compete. Here's…
- Should You Give Your Kids Their Inheritance While You're Still Alive? · 5 minA living inheritance can help children when they need it most, but large gifts can create tax and estate-planning consequences. Here’s what to consider before transferring wealth.
- New Retirement Plan Rule for Long-Term Care Premiums · 4 minA 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 · 5 minSupporting 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 · 4 minBusiness 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 · 6 minShould 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…
- What Every Executor (Personal Representative) Should Know About Personal Liability For a Decedent’s Taxes · 6 minAn 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…
- September 15 Is the Third Quarter Estimated Tax Deadline · 5 minIf 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…
- The 10-Year Retirement Countdown: What to Do Differently at 50, 55, and 60 · 5 minYour 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…
- Donating Appreciated Stock Is One of the Most Tax‑Efficient Charitable Gifts · 6 minDonating 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…
- Inheriting an IRA: A Guide for Taxpayers · 6 minIf 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…
- The Holiday Rush Starts Now: 7 Financial Moves Businesses Should Make Before Q4 · 5 minThe holiday season starts earlier than many business owners realize. Discover seven proactive financial moves to strengthen cash flow, manage inventory, and optimize taxes before…
