The STR Tax Advantage Conference

[Andrew Rodriguez]

Tired of losing income to taxes? Learn how high earners use short-term rentals to build wealth and keep more of what they make.

What's This Event?

Most high-income professionals overpay on taxes every single year — not because they're doing anything wrong, but because they haven't discovered the strategy that changes everything.

Host Like A Pro, NYC's premier real estate education group, presents The STR Tax Advantage Conference: a one-day intensive for high-income professionals who want to use short-term rental investing to save tens of thousands of dollars in taxes and build real, lasting wealth.

This is not a beginner Airbnb class. This is a strategic financial workshop built for people who are serious about putting their income to work smarter — led by some of the most recognized names in the short-term rental industry.

What You'll Walk Away With

✔ A clear understanding of the STR tax strategy and whether you qualify to offset your W-2 or business income

✔ Real case studies with real numbers — how high-income investors use bonus depreciation and cost segregation to generate up to $100K+ in tax savings in a single year

✔ A market and deal framework for evaluating properties, running the numbers, and financing your first STR

✔ A post-close roadmap: from getting listed to managing your property to scaling beyond property #1

✔ A room full of the right people — investors, operators, agents, and tax pros navigating the exact same decisions you are

Who Should Attend

→ High-income professionals looking to legally reduce their tax bill without cutting their income

→ Anyone curious about STR investing but unsure where to start or whether it's right for them

→ People who've heard about short-term rental tax strategies and want to understand them with real numbers, not hype

→ Anyone ready to take their first (or next) step toward a short-term rental acquisition

Confirmed Speakers

We've assembled a powerhouse lineup of nationally recognized STR investors, tax strategists, and educators who have collectively helped thousands of investors build wealth through short-term rentals.

🎤 Mike Sjogren — Founder, STR Secrets | Boutique Hotel & Short-Term Rental Expert 🎤 Jeremy Werden — Founder, BNBCalc | Short-Term Rental Investor | Host of STR Pros Podcast 🎤 Nick Aiola — Founder & CEO, Aiola CPA | Real Estate Tax Strategist 🎤 Mark Shay — President, Pocono Association of Vacation Rental Owners | Licensed Realtor 🎤 Jarrett Chouinard — Founder & CEO, Stella Retreats 🎤 Andrew Rodriguez — Founder & CEO, Stay-Booked | Short-Term Rental Investor

Additional speakers to be announced

REGISTER HERE: https://www.eventbrite.com/e/host-like-a-pro-str-tax-advanta...
Event Details

• Date: Saturday, June 20, 2026
• Location: Midtown Manhattan(venue TBA)
• Format: One-day conference with expert presentations, live case studies and networking
• Capacity: Limited to 85 attendees
• Food & Beverage: Pastries, coffee and lunch will be provided