Stephen’s Approach
Stephen D. Cummings
ChFC®
Lead Advisor / Financial Advisor / Member Owner
Overview
Stephen “Steve” Cummings is a lead advisor and financial advisor based in our Chicago Loop office, where he works closely with clients to help them navigate complex financial decisions with clarity and confidence. He holds the Chartered Financial Consultant® (ChFC®) designation, reflecting his commitment to advanced financial planning and lifelong learning.
Steve has more than 35 years of experience in the financial services industry. He launched his investment career at Continental American Trading Company in London before returning to Chicago, where he spent 15 years as a member and market maker on the floor of the Chicago Board of Trade, specializing in bond trading. In 2007, he joined Orion Capital Management and continued serving clients when it joined Savant in 2015.
Steve stays actively involved in his community. He is a member of the Evanston Chamber of Commerce, serves on the nominating committee at the Wausaukee Club, and belongs to the American Platform Tennis Association.
Away from client work, Steve enjoys staying active and being social. He spends summers on the golf course and winters playing platform tennis. He also likes attending concerts, sporting events, and neighborhood gatherings with his family. Steve and his wife, Kara, have two sons, Ben and Charlie.
Areas of Focus
Comprehensive Wealth Management
Integrated guidance for your full financial life, bringing together investment, tax, estate, and retirement planning to support your goals.
Financial Planning
Our planning process helps you evaluate key areas of your financial life, uncover opportunities, and make decisions aligned with your goals.
Investment Management
Evidence-based investing designed to help you stay focused on long-term goals while navigating changing market conditions.
Estate Planning & Wealth Transfer
Thoughtful estate planning guidance to help organize your affairs, support your wishes, and prepare for future generations.
Trust Services
Comprehensive trust administration supported by integrated investment, tax, estate, charitable, and business succession planning services.
Equity Compensation
Guidance for navigating equity compensation, including stock options, restricted stock, and other awards, as part of your broader financial and tax planning strategy.
Family Office Services
Designed for high-net-worth and ultra-high-net-worth families, our Family Office services coordinate investment, tax, estate, and accounting guidance in one place.
Tax Advisory & Preparation
Working year-round to help you stay ahead of changing laws, find strategies to help lower your tax burden, and find new opportunities.
High-Net-Worth Divorce
Navigate the financial complexities of divorce with coordinated guidance across investments, tax planning, estate considerations, and wealth management.
Technology Professionals
Guidance for tech professionals navigating stock options, RSUs, equity compensation, and related tax considerations as part of a broader financial plan.
Affiliations
- Evanston Chamber of Commerce – member
- Wausaukee Club – nominating committee member
- American Platform Tennis Association – member
Professional Designations
- Chartered Financial Consultant®
Insights & Perspectives
Thought leadership on wealth management, tax strategy, and financial planning.
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