Twenty years ago, Olin Eargle arrived in the city to work with Oprah Winfrey’s production network. After he left the corporate media landscape, his sharp pivot into residential brokerage required building an independent client base from scratch. Sixteen years later, he has achieved a top-producing career as the leader of The OSC Team at @properties Christie’s International Real Estate.
Arriving in the city as an outsider, Olin worked to master its structural grid. The North Side, Northwest Side, North Shore and downtown neighborhoods he represents are sectors he actively studied. This geographical familiarity runs so deep that he could be dropped anywhere in the city and find his bearings within seconds.
Olin’s approach to working with clients is easy to summarize: upfront structure and an enjoyable process. From the beginning, his clients receive a thorough buyer or seller meeting, then experience a lot of education and laughs between that point and closing. His clients rely on his candor, as he always gives them an honest read on their situation.
Holding the Accredited Buyer’s Representative, Certified Negotiation Expert, Real Estate Negotiation Expert, and Graduate, Realtor Institute designations, Olin works with first-time buyers, the LGBTQ+ community, investors and luxury clients across condominiums, single-family homes and multifamily properties. About 90% of his new business comes from referrals or repeat clients. He currently serves as vice president of the Referral Exchange chapter of BNI Chicago, one of the city’s leading professional referral networks.
Outside of real estate, Olin is a board member of The Orange Tent Project, which delivers meals and insulated shelters to Chicago’s unhoused residents. In addition, he is a professional singer with The Beaus, a men’s vocal group. He has sung at Carnegie Hall and will perform at the Barbican in London this summer.
