Rich sits down with Elliott Caldwell - Entrepreneur, Real Estate Investor, CEO, and Co-Founder of Home Team Vacation Rentals.  On April 1st, 2022 Elliott sold his previous business.  After a 2-3 month hiatus Elliott started a management company (Home Team) with Michael Elefante. In 16 months Home Team has become one of the fastest growing property management companies in the country with over 320 properties under management.  Home Team has also launched Home Team Design and is soon launching their first fund through Home Team Capital to invest in luxury Airbnbs.

Rich and Elliott start off by discussing what Elliott does in the short term rental space, Elliott’s first company - a high school fundraising business, managing 300+ properties, providing value for Investors, Michael Elefante, the biggest challenge that Elliott’s company has faced, the challenges of accounting in-house, automated services and their benefits, the rundown of how Elliott’s company operates, and working with turnkey clients.

They then reflect on the over-saturation of Airbnb, performing in over-saturated markets, Rich’s luxury Airbnb in Scottsdale, the opportunity to buy rentals in San Diego, how markets will vary, when and why consumers will stay in short-term rentals versus hotels, the boutique hotel model, where Elliott sees his company heading in the next few months, starting real estate funds, and when to effectively utilize debt.

Lastly, Rich and Elliott talk about a new deal that Michael has in the works, the 20% rule, buying property management companies and what that looks like, the importance of the relationship between buyers and sellers, the retention rate of Elliot’s clients when they merged companies, what Elliot’s operations team looks like, dynamic pricing, scaling up companies, working with Somerled Designs, the current market trajectory, and the turnkey model.
 
Connect with Elliott on Instagram: @elliottcaldwell

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