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All Episodes

deepdive. — 59 episodes

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Title
1

Important Change For Premium Tax Credit Repayments In 2026; What Taxpayers Need Know Now

2

Hiring, Layoffs, and Contractors: Payroll Tax Mistakes That Get Expensive Fast

3

Domicile: What It Means, Why It Matters, and How to Protect Your Tax Position

4

No Direct Deposit? Your IRS Refund Could Be Delayed for More Than Two Months

5

Free Retirement Money? Here’s How to Get It

6

Trump Accounts and Gift Tax Returns: How IRS Guidance Changed the Rules for Family Contributions

7

Reasonable Compensation Is Not a One-Time Decision

8

If You Owe the IRS Money, Here’s What You Should Know About the Statute of Limitations on Collection

9

Booming or Slowing Down? Why Your 2026 Tax Strategy May Need a Reset

10

Choosing Between an S Corporation and a C Corporation: It’s About More Than Tax Rates

11

IRS to Provide Automatic Penalty Relief to Normally Compliant Taxpayers

12

IRS Announces Mid-Year Optional Vehicle Mileage Rate Increase

13

Mid-Year Tax Planning Is Not a Luxury. It’s Where Real Planning Happens.

14

Maximize Pay, Minimize Taxes: A Guide to Fringe Benefits for Employers and Employees

15

The Hidden Homeownership Tax: Why Mortgage Shopping Can Be a Smart Financial Move

16

What Taxpayers Need to Know About Tokenized Securities and 2026 Tax Reporting

17

Understanding Social Security: Why Planning Matters More Than Ever

18

Trump Accounts and Scam Alerts - How to Protect Your Child's Savings

19

IRMAA: The Stealth Retirement Tax Many Affluent Retirees Miss

20

Weddings, Childcare, Children’s Summer Employment, and Travel: Navigating Summer’s Tax Minefield

21

You Got the Tax Deduction. But Do You Still Control the Money?

22

Could Your Dog Qualify for a Tax Break? A New Proposal Says ‘Yes!’

23

Florida Is Rethinking Property Taxes. Other States Are Watching Closely.

24

Why an IRS Online Account Matters — And How to Create One

25

The Businesses Winning Right Now Aren't Better Predictors. They're Better Planners.

26

Trump Accounts Go Live July 4. What to Do Now to Avoid Losing Out

27

The Lean Revolution: How AI Is Creating a New Class of Small Business Owners

28

Why Your P&L Is Lying to You (And What Your Cash Flow Is Trying to Tell You)

29

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

30

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

31

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

32

The Side Hustle Tax Trap Hitting Gen Z

33

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

34

The Emergency Savings Crisis Quietly Growing in America

35

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

36

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

37

Unlocking Healthcare Savings: How HSAs and HDHPs Can Combat Rising Insurance Costs

38

Just Starting a New Business? Don’t Overlook Start-Up and Organizational Costs Deductions

39

Sports Betting Isn’t Just Entertainment Anymore — It’s Tax Policy

40

Portland’s “Most Hated Tax” Might Be Changing. Here’s What That Actually Means

41

Did You Repay Money You Paid Taxes on in a Prior Year? There is a Solution to Provide Tax Relief.

42

Unlocking Tax Savings: Navigating the Complex World of Foreign Travel Deductions

43

Keeping It in the Family: Tax Risks and Benefits of Home Title Transfers

44

Foreign Earned Income Exclusion: Navigating the Opportunities

45

Why December 31,2026 is a Make-or-Break Date for Original QOF Investors

46

Tens of Millions Claimed New Tax Breaks — Did You Miss One?

47

Where Is My Refund? What To Do When Your Refund Is Way Overdue (And Why a New IRS Notice Might Be The Reason)

48

Struggling to Pay Your Taxes? Here Are Solutions and Guidance

49

The Real Cost of Hiring (It’s Not Just Salary Anymore)

50

Gen Z Is Earning Differently—And Most Are Getting Taxes Wrong

51

The IRS Is Winning Tax Cases—Why “Creative” Strategies Are Getting Shut Down

52

A Surprise Refund Opportunity? Millions of Taxpayers May Be Owed COVID-Era Penalty Refunds

53

The Penny Is Disappearing—Here’s What That Means for Your Pricing, Payments, and Profits

54

This NBA Insider Stole Millions — And It’s a Warning for Every Business

55

Clients Are Paying Slower—And It’s Not Just You

56

How Real Estate Professional Status Can Benefit Property Owners

57

The 3 Numbers Every Business Owner Should Check Monthly (But Usually Don’t)

58

White House Announces Drug Pricing Deal and Retirement Access Expansion

59

Top Year End Tax Strategies to Boost Your Business Bottom Line