Brothers Brook

Brothers Brook, LLC is a private investment company established in 2010 and based in Stamford, Connecticut. The firm specializes in making value-add investments in the consumer internet and healthcare services sectors. Through its strategic approach, Brothers Brook seeks to identify and enhance the growth potential of companies within these industries.

Jeffery H. Boyd

Managing Director and Founder

3 past transactions

Truss

Series A in 2019
Truss Holdings, Inc. operates an online marketplace that simplifies the leasing process for small and medium-sized businesses seeking office, co-working, industrial, and retail spaces. Founded in 2016 and based in Deerfield, Illinois, its platform employs machine learning to match businesses with suitable properties, allowing users to virtually tour listings, compare prices, and manage lease documents seamlessly. The company offers dedicated brokers to support clients throughout the process, ensuring a smooth experience. Truss is noted for its commitment to price transparency, enabling business owners to compare costs of traditional office and co-working spaces effectively. Through its technology-driven approach, Truss provides a cost-effective solution for businesses looking to find the right space quickly and confidently.

HealthCare.com

Series A in 2015
HealthCare.com is an online health insurance company that offers a data-driven shopping platform to assist American consumers in enrolling in individual health insurance and Medicare plans. Founded in 2014 and headquartered in New York City, the company utilizes artificial intelligence and machine learning to enhance user experiences, enabling customers to find, compare, and purchase insurance products that best meet their needs. HealthCare.com also markets proprietary health insurance and supplemental insurance products under the name Pivot Health. Its services include a comparison platform that provides expert advice, data, and personalized recommendations, empowering users to make informed decisions regarding their healthcare coverage. The company has been recognized as one of America's fastest-growing businesses, earning a spot on the Inc. 5000 list multiple times.

Redfin

Series G in 2014
Redfin is a residential real estate brokerage that combines traditional real estate services with advanced technology to streamline the home buying and selling process. The company provides a search platform for users to find homes listed by brokers as well as for-sale-by-owner properties, utilizing MLS listing information and historical data presented on an interactive map. Redfin's agents collaborate with engineers to develop tools that simplify real estate transactions. Additionally, Redfin offers mortgage loans and title and settlement services through its website and mobile application, generating the majority of its revenue from real estate services.
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