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James (Jim) Winokur


Jim Winokur, a distinguished professional in the realm of retirement planning and wealth management, stands as the epitome of dedication and empathy in the financial services industry. With a robust background spanning over two decades and multiple sectors of the financial industry, Jim has traversed the landscape of both large national insurance firms and intimate boutique companies. It was during this rich experience that he honed his craft and developed a profound understanding of the intricate needs of individuals and small business owners.

Jim’s expertise lies in retirement planning, wealth management, long-term care, and Medicare. His qualifications speak volumes, an RFC holding multiple securities designations, as well as being long-term care certified and possessing a Master of Affairs degree in international development. His accolades don't end there; he has been featured on Yahoo Finance, Bloomberg, MarketWatch, and Fox.

In 2016, Jim founded Win Retirement Solutions with a focus on serving high-net-worth individuals. However, he recognized the pressing need for assistance among Main Street Americans. This realization prompted the creation of Retire with Jim in 2021, dedicated to empowering those who have diligently prepared for retirement but find themselves underserved in the financial landscape.

Both Win Retirement Solutions and Retire with Jim offer the innovative POM process (Peace of Mind), a four-step approach designed to transition clients from uncertainty to confidence in their retirement prospects. Jim takes pride in being able to offer this peace of mind, ensuring that his clients can enjoy their retirement years without the fear of outliving their savings.


James Winokur

Founder and Owner: Win Retirement Solutions | Retire with Jim

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