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
141 episodes
Year-End Individual Tax Planning Opportunities
Year-end is rapidly approaching, as are the holidays. So, before you become distracted with the seasonal celebrations, it may be in your best interest to consider year-end tax moves that can benefit your 2025 tax filing.
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Season 1
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Episode 141
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4:32
Last-Minute Year-End Tax Tactics: Maximize Your Business Savings Now!
As the year draws to a close, small business owners find themselves in a crucial period for financial organization and tax strategy optimization. With the potential to significantly reduce your 2025 tax bill, implementing effective tax strategi...
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Season 1
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Episode 140
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4:22
Business Life Events That Can Affect Your Tax Strategy
Major life and business events—partnership changes, disputes, marriage, or retirement—can reshape your tax picture. Learn what to plan for before it costs you.
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Season 1
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Episode 139
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9:24
Cash Flow vs. Profit: The Hidden Reason Healthy Businesses Struggle
Even profitable businesses can run short on cash. Learn why cash flow and profit aren’t the same—and how smart planning helps you stay financially strong year-round.
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Season 1
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Episode 138
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4:57
Penalties That Can Wreck Your Finances
Late filings, underpayments, and payroll mistakes can trigger costly IRS and state penalties. Learn which ones to watch for and how to prevent them before they spiral.
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Season 1
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Episode 137
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4:33
Multiple Side Hustles, One Big Tax Headache
Earning income from TikTok, Shopify, Venmo sales, or freelance gigs? Learn why multiple income streams can complicate your taxes—and how to stay compliant while maximizing deductions.
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Season 1
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Episode 136
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9:25
When Your S-Corp Investment Tanks: Can You Write It Off — and When?
Thinking of writing off your S-corp investment? Learn when it’s actually allowed, how to document worthlessness, and what happens if your business rebounds. Plan your next move with expert guidance.
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Season 1
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Episode 135
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12:44
Beyond the Basics: Unlocking Tax Savings with Deductions Beyond Itemizing
In the complex world of tax deductions, understanding the distinctions between above-the-line deductions, below-the-line deductions, and standard and itemized deductions is crucial for effective tax planning. Each category serves a distinct pur...
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Season 1
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Episode 134
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8:09
Tax Advantages of Qualified Charitable Distributions (QCDs)
Qualified Charitable Distributions (QCDs) are a highly effective tool in the tax planning toolkit, particularly for retirees who are required to take Required Minimum Distributions (RMDs) from their Individual Retirement Accounts (IRAs).
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Season 1
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Episode 133
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9:07
Understanding the Taxation of Lawsuit Settlements: What Taxpayers Need to Know
Receiving proceeds from a lawsuit settlement can significantly impact your financial situation, and understanding the tax implications is crucial for effective financial planning.
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Season 1
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Episode 132
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11:00
Maximize Retirement Savings: Don’t Overlook Catch-Up Contributions for Taxpayers Aged 50 and Over.
As retirement approaches, many older Americans seek strategies to maximize their savings and ensure financial stability. Retirement plans often provide "catch-up" contributions, a frequently overlooked opportunity to significantly boost retirem...
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Season 1
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Episode 131
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9:49
Plan Now For the 2027 Revival of Opportunity Zone Investment Tax Breaks
Considering the forthcoming revival of Opportunity Zone investment tax breaks, taxpayers poised to realize significant capital gains have a unique opportunity to enhance their financial strategies while contributing to community revitalization....
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Season 1
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Episode 129
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4:41
Remote Employees, Reimbursements & Taxes: The Two Paths You Can Take
Remote teams = extra costs. Internet, phone, office gear. Two reimbursement paths: taxable stipends or tax-free accountable plans. Which saves you more? Find out now.
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Season 1
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Episode 128
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8:40
Uncertainty Is the New Normal: How Small Businesses Can Stay Steady
Economic uncertainty is the top concern for small business owners in 2025. Learn how to manage cash flow, plan for inflation and tariffs, and build resilience with smart financial controls
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Season 1
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Episode 127
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13:26
Tariffs Just Handed You Growth. Now Comes the Hard Part.
Tariffs are fueling rapid growth for U.S. manufacturers. Here’s how to manage the risks—policy swings, hiring gaps, supply chain chaos—before growth spins out of control.
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Season 1
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Episode 126
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8:57
College Planning Doesn’t Have to Be Overwhelming
From 529 plans to FAFSA and Pell Grants, most families don’t know all the ways to fund college. Here’s how proactive planning makes paying for school less overwhelming.
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Season 1
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Episode 125
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12:26
Understanding the Estate and Gift Tax Changes Under the One Big Beautiful Bill Act
The One Big Beautiful Bill Act (OBBBA) recently introduced substantial changes in the realm of estate and gift tax planning. These changes present new opportunities for taxpayers. The legislation modifies critical aspects of the estate tax excl...
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Season 1
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Episode 124
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7:10
How the Adoption Credit Can Ease Your Path to Parenthood
Are you in the process of or thinking about adopting? The tax code includes an adoption credit which is a significant benefit available to taxpayers who adopt a child, providing financial relief for eligible expenses.
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Season 1
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Episode 123
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4:16
Vehicle Loan Interest Deduction A Restrained Tax Benefit
In the swirling complexities of tax legislation, even well-intentioned provisions can seem like offers of relief that arrive weighed down with restrictions. The OBBBA provision, which allows taxpayers to deduct up to $10,000 of interest paid on...
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Season 1
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Episode 122
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11:22
The 2025 Guide to Small Business Tax Deductions You Can’t Afford to Miss
Missing key deductions could cost your business thousands in 2025. Learn the tax breaks that protect your cash flow — and how to plan ahead for 2025.
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Season 1
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Episode 121
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10:22
From Side Hustle to Six Figures: Turning Your Small Business Into a Scalable Firm
Ready to grow your side hustle into a full-time, six-figure business? Learn the smart steps to scale and set your business up for lasting success in 2025.
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Season 1
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Episode 120
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7:12
Launching a Bright Financial Future: Tax Benefits for Your Children
There are government and tax benefits that give your children financial benefits for their future. Some from the time they are born. Don’t miss out; the earlier you start the bigger their head start financially.
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Season 1
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Episode 119
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13:47
How to Keep Your Business in the Family—Tax Traps and Solutions
Thinking of passing your business to your kids or grandkids? Learn how to avoid the biggest tax traps—like capital gains, gifting mistakes, and S-corp nightmares—and how to keep your family business thriving for generations.
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Season 1
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Episode 118
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16:00
Tax Break for Businesses: 100% Bonus Depreciation is Back Plus New Expensing of Qualified Production Property.
The reinstatement of 100% bonus depreciation is a critical component of recent U.S. tax legislation aimed at fostering economic growth. The 2017 Tax Cuts and Jobs Act (TCJA) had already put significant emphasis on bonus depreciation, but its re...
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Season 1
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Episode 117
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12:41
Understanding the New Deduction for Overtime Under the OBBBA: A Comprehensive Guide
The One Big Beautiful Bill Act (OBBBA) marks a significant shift in the tax landscape, bringing with it a range of changes aimed at easing the financial burden on American workers. Among these changes, the introduction of a new deduction for ov...
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Season 1
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Episode 116
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6:44