Cash Flow and Tax Saving Strategies with STRs

The Alternative Investing Club Friday Speaker meeting for 8/18/2023.

Cale Delaney, who self-titles himself as the Accidental-Intentional Millionaire, is a Christian, Real Estate investor, entrepreneur, husband and father of 3. After graduating cum laude with an Engineering degree from Univ. of Miami, he began his real estate career in 2006 working as a Commercial Real Estate Investment Broker in Miami, FL where he was awarded the Pace Setter award his first year for the greatest number of listings and sold over $7M in multi-family and retail Real Estate.

However, with the crash of 2008 he left that business and put the Real Estate on hold until 2020 when he decided to go all in to start building generational wealth for his family. 

Since then, his investment portfolio went from $300k in January 2020 (a previous primary home turned LTR) to over $6M less than 2 year later. In those two years he acquired a total of 13 units including 5 LTRs and 8 STRs, 7 of which are luxury log cabins in the Smoky Mountains in TN.

Due to his rapid success, he’s been featured on several well-known podcasts, including Bigger.

Pockets Real Estate Rookie.
Cale self manages all his properties remotely and as of December 2022 left his W2 job to focus on his Real Estate ventures. In the first 18 months his business Mountain to Sea Cabins & Cottages generated over $1.2M in bookings and hosted over 3,400 guests (including over 100 pets!). He took his very first STR cabin from a projected revenue of $85k to an actual of $150k and converted a LTR generating $17k to a STR generating $70k.

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Cale’s focus now is on building his STR business with the intent to diversify into larger multifamily and/or self-storage for additional passive income streams. He also has several projects in the works including a non-profit, mastermind program, co-hosting, and podcast (The Fit Investor Podcast).