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.

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Episoder(296)

AI + Accounting Software: What Happens When You Get Advice Based on Bad Books?

AI + Accounting Software: What Happens When You Get Advice Based on Bad Books?

AI is transforming accounting software like QuickBooks. But messy or incomplete books can lead to misleading automated insights. Learn why clean financial data matters first.

2 Apr 14min

Phishing & AI-Powered Email Scams: How to Protect Yourself and Your Business

Phishing & AI-Powered Email Scams: How to Protect Yourself and Your Business

Phishing scams surge during tax season. Learn how AI-powered emails, IRS impersonation, and payroll fraud work—and the practical steps you can take to protect your business.

2 Apr 15min

Behind on Payroll Taxes? This Is the Most Dangerous Tax Debt Your Business Can Have

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.

24 Mar 17min

Your Q1 Financial Checkup: 5 Numbers Every Business Owner Should Review Before April

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.

24 Mar 16min

Estimated Tax Payments Are Not Just for the Self-Employed

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 ...

20 Mar 16min

Unlocking the Tax Maze: What Every Immigrant Needs to Know About Tax Filing in the U.S.

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 res...

19 Mar 21min

How to Protect Your Business From Employee Bookkeeping Fraud

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.

17 Mar 18min

Trump Accounts 2026: A Powerful Financial Head Start for Your Child

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.

17 Mar 6min

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