Founded in 2005, Dan started Winslow Financial equipped with extensive investment expertise as Vice President and Actuary at Trust-mark Insurance Company. His unique trifecta of Certified Public Accountant (CPA), licensed Investment Adviser Representative (IAR), and previous Fellow of the Society of Actuaries (FSA), makes him uniquely qualified to serve as a trusted adviser for business owners and individuals. Rafi joined Dan in 2008 after completing the Series 65 requirements to become an IAR. He brings a rich Actuarial acumen from over 20 years as a health care actuary involved with pricing, reserving, predictive modelling and data mining.

Our founding philosophy with its guiding principles remains extremely relevant in today’s ever challenging environment: First and foremost, we excel at listening and understanding our client’s needs. Then, once underlying issues are crystal clear, we work together on solutions. Our strictly fee-based compensation ensures we only have our client’s best interest in mind. No commissions; No biases. We excel at foreseeing, avoiding, and protecting clients from problems before they arise. Our extensive Actuarial training and expertise is all about risk – avoid, reduce, and/or get paid accordingly. While the ‘science’ behind financial planning involves selecting higher performing, better value investments, the ‘art’ behind financial planning aligns those solid investments with clients’ risk tolerance. The ‘best’ investments are useless if they are not an appropriate fit. And we outperform our competitors by minimizing expenses. Our fees and investment selection are designed to avoid necessary drag on our client’s returns. Our 99% client retention rate validates our success.

Rafi Herzfeld, FSA, IAR

Fellow of the Society of Actuaries
Investment Advisor Representative

(773) 909-4870

  • Fellow of the Society of Actuaries since 2006
  • Series 65
  • Georgia State University, MAS, Actuarial Science, 1994
  • Vanderbilt University, BA, Mathematics and English, 1990
  • Continuing Education (Actuarial)
  • Seminars, Network of experts
  • Continuous research in health insurance, predictive modelling, and data modelling and analysis.

Daniel E. Winslow, IAR, CPA

previous Fellow of the Society of Actuaries
Investment Advisor Representative
Certified Public Accountant

(847) 217-0366

  • Founder Winslow Financial LLC
  • Fellow of the Society of Actuaries 1989 – 2022
  • Vice President and Actuary, Trustmark Insurance Company, 1992 to 2005
  • Certified Public Accountant since 2007
  • Northwestern University Kellogg Executive Development Program
  • Northwestern University, B. A., Economics 1984
  • Series 65
  • Continuing Education (Actuarial and Illinois Ins Agent)
  • 401(k) and Chicago Actuarial Association Seminars, Network of experts
  • Continuous research in world events, investments and tax law