After bartending around Vail for four years, Ryan started the Westside Cafe (2002) which he still owns and is one of the highest volume restaurants in Vail. Since then, he continues to have his hands in many different projects including a small mobile home park, an RV storage facility, and the remodeling and rebranding of a 62-room motel.

He has also built, run, and sold several businesses included a financial service business and two quick serve restaurants.

In 2012, Ryan decided to start a distillery in his hometown of Vail, CO. After much due diligence, attending Moonshine University, and sampling of product, he succeeded. 10th Mountain Whiskey and Spirits officially opened its doors in 2014 and has been growing ever since. They are the first distillery to offer an affiliate program and are able to ship direct to consumer in 26 states. The brand has seen rapid growth and their story has been featured in numerous media and documentaries.

Ryan is also the founder of a 501(c)(3) non-profit called War Angel Concerts that provides a controlled venue for military vets with PTSD to see their favorite bands.