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
113 episodes
Estate Planning Is No Longer Optional—Even If You're Not a Millionaire
Estate planning isn’t just for the ultra-rich. Learn why Gen Xers and Boomers should act now—especially with new tax laws, digital assets, and AI fraud risks reshaping the future of legacy planning.
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Season 1
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Episode 112
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9:06
Mid-Year Inventory Assessment: Don’t Let Dead Stock Eat Your Margins
Before slow-moving inventory turns into a warehouse graveyard, take a mid-year look at what’s working—and what’s not. Learn how to spot dead stock early, plan promos, and protect your bottom line in 2025.
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Season 1
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Episode 111
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5:09
Navigating SALT Deduction Changes and Passthrough Entity Strategies for Maximum Benefit
The OBBBA has sought to provide some relief from the TCJA's stringent $10,000 cap on SALT deductions, albeit temporarily and with limitations for higher-income taxpayers.
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Season 1
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Episode 110
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3:38
Understanding the Implications of a Job Loss: Tax Considerations and Financial Strategies
A job loss is a challenging event that can have significant financial and tax implications. As individuals navigate the transition, understanding these implications and the resources available can mitigate some of the stress that accompanies su...
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Season 1
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Episode 109
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10:13
A Comprehensive Guide for Itemized Medical Deductions
The Internal Revenue Service (IRS) permits taxpayers to deduct certain unreimbursed medical and dental expenses as itemized deductions on Schedule A of Form 1040. To qualify, these expenses must exceed 7.5% of your adjusted gross income (AGI).
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Season 1
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Episode 108
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6:22
Could Your Business Run Without You? What to Do Now in Case Life Happens Later
Health issues, family emergencies, and burnout can strike at any time. Learn how small business owners can protect cash flow and keep operations running—even if they have to step away.
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Season 1
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Episode 108
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9:58
Master Your Retirement: Essential Strategies for a Secure Future
Planning for retirement is an essential journey to ensure financial stability during your golden years. Consider downsizing your living arrangements, optimizing tax deductions, and managing income from various sources (some for the first time)....
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Season 1
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Episode 107
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8:34
Retired, Relaxed… and Overpaying Taxes? Here's How to Keep More of Your Money
Retirement doesn’t mean you stop paying taxes. Learn how to avoid RMD penalties, reduce Medicare surcharges, and plan smarter withdrawals to keep more of what you’ve saved.
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Season 1
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Episode 106
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4:24
Married, Successful, and Overpaying? Tax Planning Strategies for High-Income Dual-Income Households
If you and your spouse both earn high incomes, you may be paying more tax than you should. Learn how dual-income couples can reduce tax liability with smart, proactive strategies.
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Season 1
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Episode 105
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12:51
Think the IRS Is Slowing Down? Why That Might Actually Increase Your Audit Risk
IRS audits are getting smarter, not softer. Learn how the IRS uses AI, DIF scoring, and third-party data matching to flag returns—and how to protect yourself.
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Season 1
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Episode 104
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4:39
Is Your Business Overpaying Taxes? 3 Mid-Year Moves That Could Save You in 2025
Don't wait until December. These three mid-year tax planning strategies can help business owners reduce their 2025 tax liability and boost cash flow.
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Season 1
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Episode 103
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4:37
Discover Lifelong Benefits: How the Adoption Tax Credit Can Change Your Family's Story
Adopting a child can be a challenging process, both emotionally and financially. To ease the financial burden, the U.S. federal government offers an adoption tax credit, providing substantial relief for adoptive families.
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Season 1
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Episode 102
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5:22
Unlocking Business Tax Credits: A Comprehensive Guide
Tax credits offer businesses significant opportunities to reduce their tax liabilities while simultaneously incentivizing certain beneficial activities. By understanding and utilizing these credits, businesses can not only save money but also c...
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Season 1
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Episode 101
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16:53
W-2 by Day, Wedding Photographer by Weekend? Don’t Let Your Side Hustle Become a Tax Nightmare
If you’re earning extra income on the side—whether it’s photography, design, or hosting on Airbnb—learn how to avoid tax surprises and take advantage of legit planning strategies.
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Season 1
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Episode 100
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8:01
Who Claims the Kids When Parents Divorce?
Divorce or separation doesn't just lead to emotional and familial upheaval; it also introduces complexities in financial matters, particularly when children are involved.
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Season 1
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Episode 99
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5:26
Navigating IRS Penalty Abatement
For taxpayers facing IRS penalties, understanding the pathways to request penalty abatement can provide relief both financially and emotionally.
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Season 1
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Episode 98
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11:21
Domestic Abuse Survivors: A Path to Financial Recovery
Survivors of domestic abuse, while navigating their recovery, may face many financial challenges, including tax-related issues. It's essential for survivors to understand their rights and available relief options to safeguard their economic fut...
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Season 1
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Episode 97
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5:29
Maximize Your Tax Savings: The Importance of Keeping Home Improvement Records Before Selling Your Home
Many taxpayers don’t feel the need to keep home improvement records, thinking the potential gain will never exceed the amount of the exclusion for home gains ($250,000 or $500,000 if both filer and spouse qualify) if they meet the 2-out-of-5-ye...
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Season 1
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Episode 96
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9:22
Tips Every Self-Employed Individual Should Know About Self-employment Tax
Understanding self-employment tax is essential for anyone who makes their living other than as an employee.
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Season 1
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Episode 95
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8:30
Summer Employment for Your Child
Summer is almost here, and your children may be looking for a summer job. The standard deduction for single individuals increased from $14,600 in 2024 to $15,000 in 2025, meaning your child can now make up to $15,000 from working without paying...
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Season 1
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Episode 94
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5:41
Getting Married Soon? Tax Considerations for Newlyweds
You think planning a wedding ceremony is complicated? Wait till you see the possible tax issues involved. If you are getting married this year, there is a long list of things you need to be aware of and plan for before tying the knot that can h...
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Season 1
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Episode 93
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9:16
Market Jitters? Smart Tax Moves Boomers Should Be Thinking About Now
Near retirement? Learn how Boomers can use tax-loss harvesting, bunching deductions, and smart planning to stay resilient through market uncertainty without investment advice.
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Season 1
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Episode 92
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8:04
When Consumers Pull Back: What Small Businesses Need to Know Right Now
Consumers are delaying purchases, travel, and dining due to economic uncertainty. Learn how small businesses can adapt their planning and stay resilient through tariff-related shifts.
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Season 1
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Episode 91
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6:11