Richard Casolari

When I was a kid, a bus driver left me standing in a snowstorm because I was one penny short of the fare. Ten below zero. Two miles home on foot. I made myself a promise that day that I have spent the last fifty-four years keeping.

I answered a blind ad out of college. Management trainee, it said. It turned out to be life insurance. I had no idea I would still be doing this half a century later, but the work kept presenting new problems, and I kept finding them worth solving.

At Advanced Financial Concepts, I serve as President and Investment Advisor Representative. Portfolio design, income analysis, and retirement income planning are the core of what I do. Most people understand the accumulation side of finance well enough. What they have not wrestled with is what happens when the paychecks stop and the portfolio has to take over. That transition is where the stakes are highest and where my work is most consequential.

Every client meeting starts the same way for me. I walk in ready to listen more than I talk. Every person sitting across from me has a story I have not heard yet, and that story shapes everything. Debt, spending patterns, blind spots about money, these surface quickly when you ask the right questions and stay quiet long enough to hear the answers.

I hold the CFP, ChFC, CLU, CASL, and RHU designations, built across decades of study that kept pace with a field that does not stand still. I studied at Chicago State University and spent years with MetLife before building Advanced Financial Concepts into what it is today.

Stephanie and I live in River North, where the city offers something worth watching on every corner. Our daughters Christina, Cara, and Catherine keep life from ever getting predictable, and our five grandchildren, Tommy, Connor, Bree, Luke, and Nolan, are the best reminder I have of why the work matters. They think this job looks easy. I have decided to let them keep thinking that.

The drums have been part of my life as long as finance has. I train seven days a week, weights and cardio both, and the Beatles remain the standard against which everything else gets measured. I catch great drummers live whenever I can.

The people on my team at Advanced Financial Concepts are the reason this practice runs the way it does. They are the backbone of this practice. Good people are harder to find than good investments. I got lucky on both counts.