Lebenthal has a history of bucking trends, or creating new ones.

The company was founded in 1925 by my grandparents, who decided to start this odd-lot firm focusing on individual investors. At the time, the municipal bond market wasn’t very substantive. It was mostly really highnet-worth investors and institutions. So there would be little pieces left over when an estate was settled or a bank was selling something, and nobody wanted the pieces. They saw an opportunity to take those pieces and sell them to individual investors.

My grandmother went to Syracuse Law School and graduated in 1920, which was unusual for women at the time. So she was my grandfather’s full partner in the business when they opened it. My grandfather died in the 1950s, and she just kept running the business until she was 93. So even though they started it together, she really was the matriarch of the family.

At what point did they know the company was hitting its stride?

In the 1970s, when my dad came in and created the advertising. My aunt had been working there from the early 1960s, as had her husband. Actually, she really wanted the business. But my grandmother wanted my dad to have the business, which is interesting given what a powerful woman she was. My dad, Jim, has always been a very endearing person, and he’s dynamic. So she let him go through his time in Hollywood.

His time in Hollywood?

After he graduated from Princeton, he was Life magazine’s Hollywood correspondent, which he still says was the most fun job he ever had. It was the heyday of Frank Sinatra and Tony Curtis and Grace Kelly. Then he became a filmmaker and even made a short-subject film that was nominated for an Academy Award in 1956 or ’57. In the late ’60s, he came to the family firm. That’s when he starting creating the memorable ads–kind of [Roy] Lichtenstein cartoons, with the guys saying, "Hmm, 4 percent tax free. Why, that’s worth 8 percent in the bank!"

But it wasn’t until the [New York] city crisis in the ’70s that we really became a force. My dad was very, very vocal about the need for New York to pay its debt, and that the bonds were still safe even though the city was on the verge of bankruptcy. The fact that things worked out for the city made us more and more known. The advertising during those times, especially on the radio, is really key to peoples’ memories of us. My dad has a really memorable voice, which Forbes referred to as "gratingly adenoidal." We imitated him growing up.

But because we were always so much smaller than people realized, I never really felt we were where we should have been, and I always had as my goal to build the business. My grandparents gave birth to it.