Free Weekly Live Training

Fridays at 11:00 AM ET — Live with Michael DiChiaro

Bring your tax questions. Each week we walk through real strategies high earners use to legally cut their tax bill — Real Estate Professional Status (REPS), Short-Term Rental (STR) strategy, and more.

What to Expect Each Week

Free. Beginner-friendly. Hosted live by Michael DiChiaro.

Live Q&A — bring your real tax questions
Beginner-friendly walk-throughs of REPS and STR strategy
How high earners legally reduce their tax bill
Audit-protection basics and why time tracking matters
How to think about depreciation, cost segregation, and entity structure
Connect with other high-earning professionals on the same path

Get a Friday Reminder

Drop your email and we'll add you to the WealthStrategy email list. We send reminders to the list before upcoming Friday trainings. Free, unsubscribe anytime.

Want a head start before the call?

Run your free Tax Checkup first. You'll see your number in 90 seconds and can come to Friday with specific questions.