All Episodes
deepdive. — 86 episodes
Don't Wait Until the Last Minute: October 15 is the Extended Due Date for 2025 Individual Tax Returns
Life Insurance Tax Issues Every Taxpayer Should Know
States Using Taxpayer Dollars to Fund College Sports
Should You Give Your Kids Their Inheritance While You're Still Alive?
New Retirement Plan Rule for Long-Term Care Premiums
When You Become the Family CFO
Why Self-Employed Taxpayers Must Keep Better Records for Travel, Vehicle, and Other Business Expenses
Pay Off Debt or Invest? How Higher Interest Rates Change the Math
What Every Executor (Personal Representative) Should Know About Personal Liability For a Decedent’s Taxes
September 15 Is the Third Quarter Estimated Tax Deadline
The 10-Year Retirement Countdown: What to Do Differently at 50, 55, and 60
Donating Appreciated Stock Is One of the Most Tax‑Efficient Charitable Gifts
Inheriting an IRA: A Guide for Taxpayers
The Holiday Rush Starts Now: 7 Financial Moves Businesses Should Make Before Q4
Back-to-School for Your Business: A Mid-Year Financial Report Card
What Counts as Taxable Income? You Might Be Surprised.
The Tax Law Changed. The Real Story Is What Comes Next.
Interest Rates Aren’t Going Back to Zero: A Business Owner’s Guide to Smart Borrowing
What Caregivers Need to Know About Medicaid Waiver Payments
Cryptocurrency and Taxes: What Everyday Taxpayers Need to Know
Prediction Markets Are Becoming a Tax Issue - Here's Why That Matters
Treasury Signals Increased Scrutiny of Sophisticated Tax Investment Strategies: What High-Net-Worth Investors Should Know
Unlocking the HSA: A Rare Triple Tax Break for Medical and Retirement Planning
The IRS Is Updating Its Voluntary Disclosure Program for Cryptocurrency: What Crypto Investors Need to Know
Succession Planning for Business Owners; Protecting Your Company, Your Family and the Tax Outcome
Maximizing Educational Savings: A Comprehensive Guide to Section 529 Plans
Before You Buy the Equipment, Seek Advice
Important Change For Premium Tax Credit Repayments In 2026; What Taxpayers Need Know Now
Hiring, Layoffs, and Contractors: Payroll Tax Mistakes That Get Expensive Fast
Domicile: What It Means, Why It Matters, and How to Protect Your Tax Position
No Direct Deposit? Your IRS Refund Could Be Delayed for More Than Two Months
Free Retirement Money? Here’s How to Get It
Trump Accounts and Gift Tax Returns: How IRS Guidance Changed the Rules for Family Contributions
Reasonable Compensation Is Not a One-Time Decision
If You Owe the IRS Money, Here’s What You Should Know About the Statute of Limitations on Collection
Booming or Slowing Down? Why Your 2026 Tax Strategy May Need a Reset
Choosing Between an S Corporation and a C Corporation: It’s About More Than Tax Rates
IRS to Provide Automatic Penalty Relief to Normally Compliant Taxpayers
IRS Announces Mid-Year Optional Vehicle Mileage Rate Increase
Mid-Year Tax Planning Is Not a Luxury. It’s Where Real Planning Happens.
Maximize Pay, Minimize Taxes: A Guide to Fringe Benefits for Employers and Employees
The Hidden Homeownership Tax: Why Mortgage Shopping Can Be a Smart Financial Move
What Taxpayers Need to Know About Tokenized Securities and 2026 Tax Reporting
Understanding Social Security: Why Planning Matters More Than Ever
Trump Accounts and Scam Alerts - How to Protect Your Child's Savings
IRMAA: The Stealth Retirement Tax Many Affluent Retirees Miss
Weddings, Childcare, Children’s Summer Employment, and Travel: Navigating Summer’s Tax Minefield
You Got the Tax Deduction. But Do You Still Control the Money?
Could Your Dog Qualify for a Tax Break? A New Proposal Says ‘Yes!’
Florida Is Rethinking Property Taxes. Other States Are Watching Closely.
Why an IRS Online Account Matters — And How to Create One
The Businesses Winning Right Now Aren't Better Predictors. They're Better Planners.
Trump Accounts Go Live July 4. What to Do Now to Avoid Losing Out
The Lean Revolution: How AI Is Creating a New Class of Small Business Owners
Why Your P&L Is Lying to You (And What Your Cash Flow Is Trying to Tell You)
Converting a Rental into Your Home: What You Need to Know About Taxes
Game, Set, Tax: The Parent’s Playbook for Sports Expenses, Deductions, and NIL
Can the IRS See Your Venmo, PayPal, or Cash App Transactions?
The Side Hustle Tax Trap Hitting Gen Z
What Tip-Earning Taxpayers Need to Know under the Tips Deduction Final Regulations
The Emergency Savings Crisis Quietly Growing in America
Unlocking the Power of Crowdfunding: Navigating Tax Implications and Maximizing Fundraising Success
The Economy Feels Uncertain. Here’s What Smart Small Businesses Are Doing Anyway
Unlocking Healthcare Savings: How HSAs and HDHPs Can Combat Rising Insurance Costs
Just Starting a New Business? Don’t Overlook Start-Up and Organizational Costs Deductions
Sports Betting Isn’t Just Entertainment Anymore — It’s Tax Policy
Portland’s “Most Hated Tax” Might Be Changing. Here’s What That Actually Means
Did You Repay Money You Paid Taxes on in a Prior Year? There is a Solution to Provide Tax Relief.
Unlocking Tax Savings: Navigating the Complex World of Foreign Travel Deductions
Keeping It in the Family: Tax Risks and Benefits of Home Title Transfers
Foreign Earned Income Exclusion: Navigating the Opportunities
Why December 31,2026 is a Make-or-Break Date for Original QOF Investors
Tens of Millions Claimed New Tax Breaks — Did You Miss One?
Where Is My Refund? What To Do When Your Refund Is Way Overdue (And Why a New IRS Notice Might Be The Reason)
Struggling to Pay Your Taxes? Here Are Solutions and Guidance
The Real Cost of Hiring (It’s Not Just Salary Anymore)
Gen Z Is Earning Differently—And Most Are Getting Taxes Wrong
The IRS Is Winning Tax Cases—Why “Creative” Strategies Are Getting Shut Down
A Surprise Refund Opportunity? Millions of Taxpayers May Be Owed COVID-Era Penalty Refunds
The Penny Is Disappearing—Here’s What That Means for Your Pricing, Payments, and Profits
This NBA Insider Stole Millions — And It’s a Warning for Every Business
Clients Are Paying Slower—And It’s Not Just You
How Real Estate Professional Status Can Benefit Property Owners
The 3 Numbers Every Business Owner Should Check Monthly (But Usually Don’t)
White House Announces Drug Pricing Deal and Retirement Access Expansion
Top Year End Tax Strategies to Boost Your Business Bottom Line