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
167 episodes
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
Using a Ghost Preparer? Who Are You Going to Call When the IRS Comes Knocking?
As people begin to have their 2025 tax returns prepared, this is a reminder to avoid unethical ghost tax return preparers whose sloppy, uneducated or fraudulently prepared returns could cause you to miss out on the many new tax deductions and l...
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Season 2
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Episode 18
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10:01
The Most Dangerous Number in Your Financials (And It’s Not What You Think)
Most business owners track revenue closely — but overlook the number that actually determines sustainability. Here’s why gross margin matters more than you think, and why it’s a CFO advisory conversation worth having.
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Season 2
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Episode 17
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8:18
Received a 1099-K? What You Should Be Concerned About.
In recent years, the financial landscape has seen tremendous shifts, with rising participation in the gig economy and increased online sales activities. Accompanying these changes is the heightened need for transparent income reporting. One too...
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Season 2
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Episode 16
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13:59
Why Profitable Businesses Still Feel Broke
Your business is profitable, but cash feels tight. Discover how tax timing, debt, owner compensation, and entity structure can quietly drain cash flow.
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Season 2
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Episode 15
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8:52
Exploring College Athletes' Evolving Income Streams: NIL Earnings and Revenue Sharing from Athletic Events
Scholarships and grants are essential for many student-athletes, providing financial support for tuition, fees, and other educational expenses, plus student-athletes, thanks to some recent court cases, can now receive both NIL income and direct...
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Season 2
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Episode 14
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11:20
The One Big Beautiful Bill’s Hidden Truths
Beneath the surface of the One Big Beautiful Bill Act’s touted benefits lies a complex web of provisions that may not deliver on all political promises, especially no tax on Social Security, tips and overtime.
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Season 2
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Episode 13
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10:36
The Silent Cash Flow Killers Hitting Small Businesses Right Now
Inflation hangover, payroll creep, tariffs, subscriptions, and tax surprises are draining SMB cash flow. Learn what to watch and how to respond.
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Season 2
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Episode 12
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9:38
Dodge the Tax Torpedoes: Navigate Your Income with Strategic Planning
Modified Adjusted Gross Income (MAGI) often emerges as a silent yet powerful factor that can dramatically influence a taxpayer’s tax outcomes. This amount, which determines eligibility for key tax benefits, can stealthily transform anticipated ...
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Season 2
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Episode 11
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13:57
Drug & Alcohol Addiction: Navigating the Tax and Financial Aspects
Navigating the complexities of drug and alcohol addiction poses not only profound personal and health challenges but also significant financial and tax-related hurdles. As individuals strive towards recovery, understanding the intricate web of ...
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Season 2
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Episode 10
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10:30
Why File a Tax Return When Not Required?
Generally, individuals are required to file a tax return for a year if their income exceeds the standard deduction for their filing status for that year. But even if they are not required to file, it may be beneficial to do so. They could be mi...
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Season 2
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Episode 9
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10:03
Unraveling the 2025 Tax Overhaul: How New Laws Could Impact You
The year 2025 marks a pivotal moment for taxpayers across the nation as sweeping changes take effect, ushered in by the One Big Beautiful Bill Act (OBBBA) and the delayed implementation of other significant legislative provisions.
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Season 2
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Episode 8
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12:53
Student Loan Collections Are Back. What Borrowers With Heavy Student Debt Need to Know Now.
Student loan enforcement is restarting. Should bankruptcy be considered? Learn the pros, cons, credit impact, and tax implications before deciding.
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Season 2
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Episode 7
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10:30
Understanding Income Tax: A Guide to Partnering Effectively with Your Tax Professional
A clear guide to income tax basics, including brackets, AGI, MAGI, deductions, credits, taxable income, and how to collaborate effectively with your tax professional.
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Season 2
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Episode 6
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13:40
Trump Accounts – Don’t Miss Out on This Opportunity for Your Children.
With the introduction of Trump Accounts under President Trump's Working Families Tax Cuts Act, also known as the One Big Beautiful Bill Act (or OBBBA), a new opportunity has been created for American families to set up tax-advantaged savings ac...
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Season 2
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Episode 6
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10:31
Received an IRS Letter? Here’s What Not to Do
An IRS or state tax notice is stressful—but panic makes it worse. Learn what not to do if you receive a tax notice and how to respond calmly.
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Season 2
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Episode 5
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10:46
Why Your Tax Refund Isn’t a Win (And What to Do Instead)
A big tax refund feels good—but it often signals missed planning. Learn how withholding reviews, estimates, and life changes affect your taxes.
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Season 2
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Episode 4
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10:39
Gen X Is Stuck in the Middle—and the Tax System Knows It
Kids, aging parents, peak income, and no time. Why Gen X feels squeezed—and why tax planning matters more than ever
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Season 2
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Episode 3
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11:53
Tax Season Is Coming, Here’s What to Know
It’s tax time, and if you are like most taxpayers, you are probably facing the ominous chore of compiling records in preparation for your tax return. The task is never easy, but the effort usually pays off in the extra taxes you save! When you ...
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Season 2
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Episode 2
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11:39
Navigating 2025's Game-Changing Tax Reforms for Individuals and Businesses
With tax season upon us, taxpayers across the nation are trying to grasp the many tax changes for 2025. Central to these transformations is the One Big Beautiful Bill Act (OBBBA), a comprehensive tax reform.
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Season 2
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Episode 1
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13:54
What To Do When You Get an IRS Notice (And Why You Don’t Need to Panic)
IRS notices can be confusing, but they don’t have to be scary. Learn what common notices mean, what to do next, and when to contact your financial professional for help.
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Season 1
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Episode 150
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10:25
Smart Year-End Money Moves for Every Generation: From Gen Z to Boomers
From retirement contributions to emergency funds, here are the smartest year-end financial moves for every generation—so you can finish the year stronger and start 2026 on solid ground.
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Season 1
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Episode 149
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10:50