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HOME TOUR: CALIFORNIA DREAMING

62 Entry Main

A design team transforms a Winnetka midcentury ranch house into a warm, contemporary retreat. Some homes always stay with you. For one former realtor, it was a 1957 ranch in Winnetka she had sold to her best friend’s parents 25 years ago. Returning to the house several years later to help her friend pack it

JUST LIKE US

81 Sydney Caine Wearing Cinq A Sept 2 Main

A new local player is bringing fresh energy to user-focused product design and development. Sydney Caine, a longtime North Shore resident, is charting her course with purpose and presence. A senior leader at Google working at the intersection of tech and healthcare, a mother of three boys, and a dedicated nonprofit board member, Caine fiercely

PROTECTING YOUR FUTURE

From high-net-worth wealth managers and finance executives to a fourth-generation leader of an insurance company that’s more than a century old, Sheridan Road’s annual North Shore Money issue is proud to showcase the professionals who help us all build and protect our investments. As you move through the stages of life, whether you’re just starting

STEVEN ESPOSITO: PRESIDENT & MANAGING DIRECTOR, YELLOWSTONE WEALTH MANAGEMENT

87 Steven Esposito

Steven Esposito is the President & Managing Partner at Yellowstone Wealth Management. Esposito first discovered his passion for finance in high school when a stock market class sparked his lifelong interest in investing. That early curiosity set him on a path that has become a distinguished career. In 1983 he began as a financial advisor

NATALIE STONE: PRESIDENT, HILL AND STONE INSURANCE AGENCY, INC.

88 Natalie Stone

As the fourth-generation owner of an insurance agency that’s more than a century old, Natalie Stone combines traditional values with innovative approaches to protect what matters most to her clients. “At Hill & Stone, we pride ourselves on prompt, professional service, holding ourselves accountable to be a reliable partner who prioritizes our clients’ needs and

JENN BARRY, CFA, CFP®: CHIEF ADMINISTRATIVE OFFICER, AARON WEALTH ADVISORS

89 Jenn Barry

As Chief Administrative Officer at Aaron Wealth Advisors, Jenn Barry works directly with the CEO and President to manage daily operations, inputs for strategic planning, and drive talent management and cultural initiatives. “At its core, my expertise lies in connection and collaboration. For 25 years, I served as a trusted resource to institutional money managers,

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