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Avery invites Julie Gates, a seasoned short-term rental property manager, to discuss the state of the short-term rental market, insights from a recent property management convention, and advice for self-managers looking to improve their property management skills.

Steve Rosenberg shares his journey from being an airline pilot to a real estate investor after the 9/11 events that dramatically changed his life. He emphasizes how he had to start from scratch, learning real estate through books and personal trial and error, and how he developed strong negotiation and communication skills that helped him succeed.

Brian Davila, a successful real estate investor and Chief Growth Officer at Future Flipper, shares his incredible journey from overcoming addiction and dropping out of high school to achieving over 300 real estate transactions. He credits his turnaround to hard work, a chance conversation with a real estate client, and a motivational push from his teacher.

In this episode of the Short Term Show, host Avery sits down with tax expert Ryan Bakke to discuss how real estate investors can benefit from tax advantages, including real estate professional status (REPS) and material participation. Ryan shares his story of how understanding real estate tax strategies changed his career and life.

Optimize Your Taxes Like a CPA with Ryan Bakke

Avery welcomes franchise consultant Kim Daly to the Short Term Show to explore the world of franchise investments. Kim explains the value of franchising, her role as a matchmaker for potential franchise owners, and how she helps people select the right franchise based on their goals, skills, and finances. The conversation provides insight for anyone interested in diversifying into franchising but unsure where to start.

Avery welcomes Pat Hiban to the Short Term Show, discussing his books, GoBundance mastermind, and sharing a hilarious anecdote about an interview with Tracy from Million Dollar Listing, where Tracy hung up mid-interview after a misunderstanding about being recorded.

Yoseph West, co-founder and CEO of Relay Bank, shares insights on how Relay helps small business and real estate owners manage their finances more effectively, tackling the challenge of running businesses based on bank balances and the need for real-time financial insights.

Kyle Stanley discusses his journey into short-term rentals, starting with his realization that he didn’t want to work forever. After trying different ventures like multi-level marketing and sales, he turned to real estate and Airbnb, building a successful business with 65+ units in Fresno, Phoenix, and Scottsdale in just three years. He also runs a podcast, The Fearless Investor, where he shares insights about real estate investing.

In this interview, Avery, the host, speaks with Diya, a former litigation attorney turned real estate investor, about her journey into real estate investing, focusing on boutique hotels and short-term rentals. Diya shares her background, her transition from law to investing, and insights into running a successful short-term rental business, including setting up her parents’ home for STR purposes.

Avery hosts real estate tax experts Amanda Han and Matt McFarland, who discuss tax advantages for short-term rental investors, demystifying key deductions and tax-saving strategies.