Craig Kallian

Craig Kallian brings a strong operational and investment-focused background to his role at Olive Real Estate Group. Originally from Wisconsin, he earned his Bachelor’s degree in Business from the University of Wisconsin–Stout and began his career in apartment asset management, where he developed a foundation in financial analysis, property performance, and value optimization.

Craig has spent the past several years working extensively in the short-term rental and hospitality investment space, partnering with investors to launch, scale, and stabilize income-producing assets. He has worked closely with clients on acquisition strategy, operational setup, and revenue optimization, leveraging his  real estate license and knowledge to help investors source and secure high-performing properties.

In addition to brokerage, Craig has been involved in the formation of three businesses and played a key role in the growth and scaling of a short-term rental property management company. His experience building systems, managing operations, and advising investors provides him with a practical, execution-driven perspective that translates directly into client value.

At Olive, Craig focuses on helping investors and property owners make informed, data-driven decisions by combining market insight with real-world operational experience.