Craig McWilliams

Craig McWilliams brings more than three decades of experience spanning business leadership, financial strategy, and investment management to FourStar Wealth Advisors. As a former CEO who founded and scaled a supply-chain quality assurance company serving over 400 customers across 30 locations, he understands the unique challenges and opportunities facing business owners— particularly founders approaching a liquidity event or exit.

Craig works closely with company founders and entrepreneurs to structure institutional-quality partnerships and implement endowment-style investment approaches that emphasize capital preservation, long-term growth, and sophisticated risk management. His focus includes relative-strength methodologies, alternative investments, and carefully constructed portfolios designed to support the transition from private company ownership to diversified, institutional-caliber wealth.

He also applies these same principles to any investor seeking thoughtful retirement planning. Craig specializes in helping clients design reliable income strategies by offering annuities and permanent life insurance solutions from multiple carriers, allowing him to match products carefully to each client’s goals, risk tolerance, and tax situation. His work often integrates these strategies when appropriate, while coordinating with FourStar specialists on Delaware Statutory Trusts, Opportunity Zone funds, and other tax-advantaged structures for capital gains deferral— including 1031 exchanges and venture exits.

Licensed in life and health insurance, Craig assists both individuals and companies in developing permanent insurance strategies that support estate planning, wealth transfer, and talent retention objectives.

Craig is known for listening carefully and educating clients so they can make informed decisions with confidence. He lives in Chicago with his wife Cindy and enjoys jazz, college football as well as weight-lifting, cycling, and swimming along Lake Michigan.