Winston Financial Group is a family-run financial services firm based in Madison, Wisconsin, offering personalized guidance for people planning and living in retirement. The firm aims to combine sophisticated wealth management strategies with a welcoming, approachable experience built on trust, transparency, and lasting relationships.

Its Companion Process guides clients through three steps: discovering their goals and reviewing their current financial picture, evaluating resources and potential gaps, and developing a custom strategy for their retirement objectives. The initial conversation is described as friendly and no-pressure, and the firm’s OnTrack Retirement Review helps clarify a client’s starting point and vision.

Winston Financial also helps clients understand Medicare options, coverage, and costs, including Medicare Supplement insurance and Medicare Advantage plans. Its website offers an informational guide to common Medicare questions. The firm provides retirement strategies using insurance products; advisory services are offered through Lasting Mark Retirement Group, while insurance products are offered through affiliated entities.