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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.
146 Episodes
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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.
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.
Learn the real difference between capital expenditures (CapEx) and operating expenses (OpEx)—and why it matters for your business’s cash flow, taxes, and strategy.
Behind on taxes or owe the IRS? Whether you’re an individual or a business owner, learn how to fix tax problems during the IRS furlough and before penalties pile up.
Inflation is steady but still squeezing margins. Learn how to use this moment to reprice smarter, strengthen cash flow, and make 2026 your margin expansion year.
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.
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 strategies now becomes imperative.
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.
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.
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.
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.
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.
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 purpose within the tax code, impacting how taxable income is calculated and influencing the overall tax liability of individuals.
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).
Receiving proceeds from a lawsuit settlement can significantly impact your financial situation, and understanding the tax implications is crucial for effective financial planning.
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 retirement funds.
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.
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.
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
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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