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May 10, 2025 · Wealth, Money & Real Estate · Quality 7/10

He fell in love with our Hamakua Hotel project and infused just shy of a million in new capital to consolidate all the short-term debt we occrued during our year of construction.

For those of you interested in my real estate dealings, both of my Hawaii property syndications achieved huge wins over the past few months. Here’s the meat:

The first occurred in February. After two solid months of unsuccessful outreach, a buddy introduced me to another entrepreneur, who like me, had a couple of recent exits and was now investing full time.

We found that we had similar philosophies and spoke the same language about real estate. I showed him both my projects. He decided that he wanted to vacation at one and invest in the other. I liked his style!

He fell in love with our Hamakua Hotel project and infused just shy of a million in new capital to consolidate all the short-term debt we occrued during our year of construction. This enabled us to pay off 100% of our short-term debt with a favorable long term loan, similar to a mortgage. I enjoyed writing big R.O.I. checks to all our early supporters!

The second closed this week. After two years of aggressive restoration work in between short-term renters, we listed our Waterfalling Estate property for sale in two ways. We offered it in entirety for $10.5 mm (we paid $5.75 mm just two years ago) and fractionally for $3.5 mm for 1/3rd ownership.

Unlike the two months of unsuccessful outreach to identify the above investor for our hotel, my very first phone call led to a new investor - a husband & wife team. They chose to join our existing investment group rather than make a full or fractional acquisition in Waterfalling Estate. This was a tremendous vote of confidence for our team that owns and operates that property.

The investment was so significant, that our ownership group has decided to hold the property longer term. We believe that it will be worth north of $15 million some day, and are prepared to take more time to find out.

With my two biggest 2025 objectives met, I was able to move back to Miami five months earlier than expected. 😎 Time to add some new goals for the rest of this year! Let’s see what I can dream up!

Key lesson: He fell in love with our Hamakua Hotel project and infused just shy of a million in new capital to consolidate all the short-term debt we occrued during our year of construction.

Summary: Both Hawaii property syndications scored huge wins; new capital consolidated debt.