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(247)

Converting a Rental into Your Home: What You Need to Know About Taxes

Converting a Rental into Your Home: What You Need to Know About Taxes

Converting a rental into your primary home can be a smart move — both for your living situation and for taxes — but it’s not as simple as move in, sell, and keep the profit.

16 Jun 5min

Game, Set, Tax: The Parent’s Playbook for Sports Expenses, Deductions, and NIL

Game, Set, Tax: The Parent’s Playbook for Sports Expenses, Deductions, and NIL

A child’s and their parent’s sports expenses, from registration fees and travel to equipment and volunteer time, sit at the intersection of personal, medical, charitable and business tax rules. For ta...

11 Jun 5min

Can the IRS See Your Venmo, PayPal, or Cash App Transactions?

Can the IRS See Your Venmo, PayPal, or Cash App Transactions?

Venmo, PayPal, Cash App, Stripe, and other payment apps can create tax reporting obligations for freelancers and small business owners. Learn how Form 1099-K works, what income must be reported, and h...

11 Jun 4min

The Side Hustle Tax Trap Hitting Gen Z

The Side Hustle Tax Trap Hitting Gen Z

From Venmo income to freelance gigs and creator revenue, many Gen Z workers are facing unexpected tax bills. Learn how side hustle taxes work and how to avoid common mistakes.

10 Jun 5min

What Tip-Earning Taxpayers Need to Know under the Tips Deduction Final Regulations

What Tip-Earning Taxpayers Need to Know under the Tips Deduction Final Regulations

A new, temporary federal tax break for tip earners went into law for tax years beginning in 2025 and runs through 2028. The change creates a below-the-line deduction for “qualified tips,” but it comes...

9 Jun 4min

The Emergency Savings Crisis Quietly Growing in America

The Emergency Savings Crisis Quietly Growing in America

More Americans are relying on credit cards instead of emergency savings. Learn why financial stress is rising and how small planning habits can improve financial stability.

6 Jun 5min

Unlocking the Power of Crowdfunding: Navigating Tax Implications and Maximizing Fundraising Success

Unlocking the Power of Crowdfunding: Navigating Tax Implications and Maximizing Fundraising Success

Crowdfunding has emerged as a popular method to raise funds for various personal, charitable, and business endeavors. However, with this comes a myriad of tax implications that organizers and contribu...

4 Jun 5min

The Economy Feels Uncertain. Here’s What Smart Small Businesses Are Doing Anyway

The Economy Feels Uncertain. Here’s What Smart Small Businesses Are Doing Anyway

Inflation, high interest rates, cautious consumers, and economic uncertainty are putting pressure on small businesses. Learn how smart business owners are adapting, protecting cash flow, and staying r...

3 Jun 4min

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