I’m Chad Shillingford, an ex-banker, now family office chief and sailor.

I’ve had the privilege of watching Boston’s skyline change over the years and now enjoy the simpler rhythms of Nantucket Island.

My days in investment banking might be behind me, but the thrill of the game remains.

Together with my brother, I helm our family office — I manage the investments, and he, with his estate planning prowess, keeps us future-focused.

When I’m not knee-deep in financial strategies, you’ll likely find me out at sea, savoring the pure joy of sailing.

On land, it’s tennis that keeps me on my toes.

And yes, like any true Bostonian, I’ve spent countless hours rooting for the Red Sox and have a soft spot for the Hyannis Harbor Hawks.

My kids, all grown up, have gifted me perspectives I never knew I needed.

Harvard and Phillips Academy laid my academic foundation, but it’s life’s experiences that truly shaped me.

I started this blog to share seasoned insights, new discoveries, and to record answers I give to the many questions my kids and friends have about investing.