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
190 episodes
Behind on Payroll Taxes? This Is the Most Dangerous Tax Debt Your Business Can Have
Behind on payroll taxes? Learn how trust fund taxes work, what triggers the IRS Trust Fund Recovery Penalty, who can be held personally liable, and why acting early protects your business.
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Season 2
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Episode 43
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17:18
Your Q1 Financial Checkup: 5 Numbers Every Business Owner Should Review Before April
Before April 15, review these five critical Q1 financial numbers. From profit margins to cash runway and estimated taxes, proactive planning now can shape the rest of your year.
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Season 2
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Episode 42
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16:20
Estimated Tax Payments Are Not Just for the Self-Employed
Unlike employees, who have taxes withheld from their wages, self-employed individuals must prepay their taxes by making periodic estimated tax payments. However, self-employed people are not the only ones who are subject to the estimated tax re...
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Season 2
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Episode 41
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16:05
Unlocking the Tax Maze: What Every Immigrant Needs to Know About Tax Filing in the U.S.
Understanding the tax obligations and potential benefits applicable to immigrants in the United States, both legal and undocumented, is complex. Their tax status hinges on specific factors such as residency status, time spent in the U.S., work ...
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Season 2
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Episode 40
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21:15
How to Protect Your Business From Employee Bookkeeping Fraud
Employee bookkeeping fraud can devastate a small business. Learn common fraud schemes, warning signs, and practical internal controls to protect your company.
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Season 2
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Episode 39
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18:32
Trump Accounts 2026: A Powerful Financial Head Start for Your Child
Trump Accounts in 2026 offer up to $5,000 annual contributions plus a $1,000 government seed for eligible children. Learn how they work, tax rules, projections, and how they compare to 529 plans.
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Season 2
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Episode 38
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6:54
Charitable Giving in 2026: Navigating New Tax Laws and Maximizing Your Gift’s Impact
As the landscape of charitable giving continues to evolve, 2026 ushers in significant changes in the tax treatment of donations. For both itemizers and non-itemizers, understanding the new rules is crucial to maximizing the benefits of charitab...
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Season 2
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Episode 37
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12:36
Things You Need to Know About Reverse Mortgages
A reverse mortgage is a financial product that allows homeowners, typically aged 62 or older, to convert part of their home equity into cash. Unlike a traditional mortgage, where the homeowner makes payments to a lender, in a reverse mortgage, ...
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Season 2
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Episode 36
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16:03
What Is Advisory — And Is It Right for You?
Advisory services go beyond historical tax and bookkeeping work to help you plan ahead, make smarter decisions, and reach long-term financial goals. Learn what advisory is and whether it’s right for you.
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Season 2
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Episode 35
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10:29
How the One Big Beautiful Bill Act Transforms R&E Tax Strategies for Businesses
The One Big Beautiful Bill Act (OBBBA), signed into law on July 4, 2025, has permanently reinstated the ability for businesses to immediately deduct domestic Research and Experimental (R&E) expenditures, reversing a controversial change mad...
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Season 2
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Episode 34
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12:51
When One Client Fuels 15%+ of Your Revenue, Buyers See Risk — Not Success
If one client generates over 15% of your revenue, buyers see risk. Learn how client concentration affects valuation, due diligence, and what to do before you sell.
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Season 2
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Episode 33
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15:45
Unlock Tax Savings with the New Auto Loan Interest Deduction
The IRS has introduced proposed regulations that outline the eligibility criteria for deductions on interest paid on loans for qualified passenger vehicles intended for personal use.
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Season 2
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Episode 32
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10:49
Tax Alert: Prepare for the New 1099-DA Crypto Reporting
The reporting requirements for Form 1099-DA officially take effect for the 2025 tax year, with brokers sending the forms to taxpayers and the IRS in early 2026. Before this change, reporting digital asset transactions was largely dependent on s...
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Season 2
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Episode 31
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15:32
Navigating Wash Sale Woes: Common Pitfalls, Tax Implications, and Strategic Avoidance
To prevent taxpayers from selling a security to claim a loss and then immediately repurchasing the same or a “substantially identical” security, the tax code has a “wash sale” rule: the loss is disallowed if the repurchase occurs within 30 days...
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Season 2
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Episode 30
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13:30
When “No Big Deal” Turns Into a Big Deal: Lessons From the IRS’s Top 10 Cases of 2025
The IRS just released its Top 10 Tax Crime Cases of 2025. These real cases show how small tax issues can quietly grow into serious problems, and what taxpayers can do to avoid them.
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Season 2
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Episode 29
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13:55
Pricing Isn’t About What You Charge — It’s About What Your Business Can Sustain
If margins are thin and cash flow feels unpredictable, pricing is often the real issue. Here’s why pricing is a CFO advisory conversation — not a guess — and how it shapes long-term stability.
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Season 2
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Episode 28
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8:58
It’s Tax Time - Beware of Scams
As the tax season gets underway, scammers are plotting to take advantage of your fear of the IRS to steal your identity, your tax refund, or even to dupe you into sending them money to pay for made-up tax liabilities. Don’t be a victim of these...
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Season 2
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Episode 27
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13:14
Understanding Designated Roth Accounts: Benefits, Contributions, Distributions, and Tax Implications
Designated Roth accounts provide a compelling retirement saving strategy for those seeking tax-free income in their golden years. With no income restrictions with respect to making contributions to this type of account and the flexibility to ma...
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Season 2
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Episode 26
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10:27
Beware of Social Media Tax Advice: The Risks and Consequences
Social media serves as a hub of information on almost every topic imaginable, from cooking recipes to financial advice, including taxes. However, as accessible as these platforms are, they pose a significant risk when used as a source for tax a...
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Season 2
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Episode 25
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8:45
How to Conduct a Profitability Check (Before Growth Kicks Back In)
A simple profitability check can reveal hidden risks and opportunities in your business. Learn how to review KPIs, prioritize problem areas, and identify top revenue generators to build a stronger, more profitable 2026.
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Season 2
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Episode 24
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13:11
Tax Ramifications for Scam Victims
Navigating the tax implications of scams and theft losses can be complex, especially considering legislative changes that generally limit casualty and theft losses to those associated with a disaster. However, if you've fallen victim to a...
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Season 2
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Episode 23
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12:01
Thinking About Moving for Taxes? This Is a Conversation You Need to Have First
With so many people talking about moving for tax reasons, it’s easy to miss the full picture. Before you pack up, here’s the tax conversation every family should have — and why it’s one you shouldn’t have alone.
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Season 2
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Episode 22
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12:01
The New Year Money Reset: 7 Simple Decisions That Make 2026 Easier
Start 2026 with clarity and confidence. Learn seven simple, tax-smart financial habits anyone can adopt to make the year easier — no investment advice required.
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Season 2
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Episode 21
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14:57
Why Profitable Businesses Still Run Out of Cash (And What CFOs Watch Instead)
Many small and mid-sized businesses are profitable on paper but still feel cash-strained. Here’s why cash flow behaves differently from profit, and why it’s a CFO advisory conversation worth having.
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Season 2
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Episode 20
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9:20
Big Changes for Pension Catch-up Contributions
2025 brought significant changes to pension contributions by introducing an additional catch-up amount for taxpayers aged 60 through 63, followed in 2026 with a requirement that catch-up contributions for higher income taxpayers mandatorily be ...
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Season 2
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Episode 19
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10:15