A Team Built on Experience and Results

Ryan Deasy started his real estate entrepreneur journey in 2012. He bought his first duplex then and has scaled up to over 60 units in 2026.

During the course of his investment career he began to get well acquainted with the loan process. In doing so, he started his own direct lending and loan brokering business called October Lending. October has scaled to doing everything from hard money loans to DSCR to ground up builds in the northeast as well as most areas of the country.

Ryan grew up in Colebrook, Connecticut. He graduated from Central Connecticut State University in 2009 with a Bachelor of Science degree in Finance. He then worked in banking, followed by a career in advisory services in the finance field. Ryan is happily married to his wife, Brenna, and live in northwest CT with their daughter and son.

Michaela joined the team as both a Loan Officer and Loan Processor, bringing hands-on experience and knowledge in real estate finance. Her journey began in 2024 when she successfully purchased and flipped her first multifamily property, sparking a passion for real estate investment.

She grew up in North Haven, Connecticut, and graduated from Central Connecticut State University in 2020 with a Bachelor of Science degree in Finance. Michaela now lives in Portland, CT, and loves spending her free time outdoors, hiking and traveling.

With a mix of real-world investing experience and a finance background, she’s here to help make the loan process smooth and stress-free.

Chris grew up in Waterbury, Connecticut, and graduated from Quinnipiac University in 2003 with a Bachelor of Science degree in Business Finance. He began his career in banking as an office manager and went on to serve as Director of Sales and Business Development in the medical field, where he honed his leadership and client relations skills.

With over six years of experience in private lending as a loan officer, Chris brings a strong financial background and a client-first mindset to the team. He is passionate about helping clients navigate the mortgage process with confidence and clarity, and he’s eager to put his expertise to work for you.

Chris currently resides in Meriden, Connecticut, with his fiancée Nazanin and their two dogs, Lucky and Diva. In his free time, he enjoys traveling, exercising, reading, and collecting comic books.

Caleb is a Loan Officer at Skytree Investments, working with real estate investors and operators to structure financing across bridge, DSCR, construction, and hybrid capital stacks. He focuses on helping sponsors navigate lender fit and execution challenges to bring transactions to a successful close.

Caleb grew up in Bloomfield, Connecticut and studied at Loomis Chaffee before attending the University of Connecticut, where he focused on accounting, finance, and real estate-related coursework. During his studies, he interned at RSM, gaining experience in accounting, tax, and advisory services.

Prior to entering private lending, Caleb was active in real estate wholesaling, sourcing off-market opportunities and working directly with investors on acquisitions. This experience gives him a practical, operator-level perspective on deal execution and capital structuring

In 2021, Judith joined the team as an executive assistant and has played an integral role in the facilitation of all outbound and inbound marketing efforts. In addition to orchestrating marketing campaigns, she handles many of the behind-the-scenes tasks that allow the business to perform efficiently and effectively.

Judith grew up in the Summer Capital of the Philippines. She graduated from the University of the Cordilleras in 2014 with a Bachelor of Arts degree in Communications. She started her career working as a customer service representative for a few well-known banking firms, followed by a career as a virtual assistant in the real estate industry. Judith is a single mom raising her 6-year-old son, Johann.