Crop insurance programs are frequently neither available nor applicable to small, diversified producers, particularly to those who are socially disadvantaged. Similarly, few farm service providers have expertise in the risks faced by these producers. To address this gap, we heeded farmers’ requests for both group and one-on-one support and built an expert network of Chesapeake farmers. Expert farmer mentors connected with 68 farmers in the Chesapeake region for individualized and group support to help farmers manage risks inherent in their sector. Farmers found 1) group support via peer-to-peer learning through facilitated “study circles”; and 2) individual support via a mentor-farmer matchmaking program for one-on-one, deep-dive assistance. Producers with similar business types and goals gathered in groups for monthly meetings, facilitated by experienced farming experts. Topics included include financial benchmarking, marketing, and crop production. Thirty producers were also connected with risk management experts, and were awarded up to $1000 per farm for one-on-one advice for their businesses.