5 Years of Real Estate Investing Lessons in 37 Minutes

Episode #729 Many rookies _think_ things become easy once you’ve *built a large real estate portfolio,* but that’s far from true. Even with *26 short-term rentals, a 13-unit hotel, and a few house flips* under his belt, Tony deals with many of the typical rookie challenges. In today’s episode, he’s *sharing the lessons he’s learned and the rental pivots he’s making so YOU can grow and scale like him!* Welcome back to the _Real Estate Rookie_ podcast! Last time we checked in with Tony about his real estate business, he was in the process of *stabilizing his new hotel.* Now, with an entire calendar year in the books, we’ll *revisit the property and how it’s performing today.* We’ll also hear about Tony’s _next_ hotel investment and how he’s approaching it differently now that he has proof of concept. Tony also outlines the best course of action for new investors who want to *break into the short-term rental space* in 2026. Finally, what does a *day in the life of a full-time real estate investor* look like? Tony gives you an inside look at the flexibility he enjoys by owning rental properties that you _don’t_ get with a nine-to-five job! Episode Show Notes: https://lnk.to/realestaterookieYT Join BiggerPockets for FREE 👇 https://www.biggerpockets.com/signup?utm_source=owned_media 🎉Join us at the BiggerPockets Conference October 2-4 in Orlando. Buy tickets: https://biggerpockets.com/bpcon2026 Grab the Book, _Smarter Short-Term Rentals_ : https://store.biggerpockets.com/products/smarter-short-term-rentals?utm_source=youtube&utm_medium=description&utm_campaign=none Sign Up for the Investor Brief Newsletter: https://www.biggerpockets.com/email-subscribe?utm_source=youtube&utm_medium=description&utm_campaign=none Find an Investor-Friendly Agent in Your Area: http://biggerpockets.com/agentmatch _Real Estate Rookie_ 349 – How to Use Public Data to Find Real Estate Deals That 99% of Investors Miss w/ Ariel Herrera: https://www.biggerpockets.com/blog/rookie-349?utm_source=youtube&utm_medium=description&utm_campaign=none Connect with Ashley and Tony: Ashley: https://www.biggerpockets.com/users/ashkehr?utm_source=youtube&utm_medium=description&utm_campaign=none Tony: https://www.biggerpockets.com/users/tonyr75?utm_source=youtube&utm_medium=description&utm_campaign=none 00:00 Intro 00:35 Tony’s Current Portfolio 01:09 Update on the 13-Room Hotel 04:28 Tony’s NEXT Acquisition 14:53 Short-Term Rentals in 2026 18:03 The Data-Driven Buy Box 23:04 Tony’s Average Workweek 26:28 Investing with Your Spouse 31:36 Best Beginner Content 35:17 First Steps for Rookies!