Talking business with Josh Henderson
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Talking business with Josh Henderson

Businessman Josh Henderson talks about moving to Florence, integrating through chess and his involvement in the Consulate’s Connect US scheme.

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Wed 12 Oct 2022 2:37 PM

Josh Henderson is a US businessman who recently moved to Florence with his family. Alongside his business Dippin’ Rings and his job in finance, he also acts as a mentor for Connect US, a scheme connecting experienced business professionals with Florentine start-ups.

Josh Henderson
Josh Henderson at The Stellar Florence

Tell me about how you came to Florence.

I met my wife in New York. She went to law school there and I worked at a chess shop right near NYU. We met through chess and when we were in New York, often people would ask her about her accent and where she was from. She’d always say Florence, but she’s actually from a town called La Romola, which is a bit further south. She attended the University of Florence and her father taught maths there before he retired a few years ago. About three years back, we decided to move to Florence to support my wife’s parents, who are in their eighties. I have my own business and my wife is an attorney, so we thought if there’s ever an opportunity for us to move, it’s now. We started planning in 2019 and, of course, we had no idea about what was coming. When the pandemic flared up here in Italy, we thought we were never going to be able to do it. But just as the date was approaching and we had everything packed and the house on the market, Covid was really raging in the US, while Italy was easing up. We were concerned because I’m not an Italian citizen and Italy was saying they were going to close the doors to Americans. But we just got in. I think the cut-off date was July 1 and that’s exactly when we landed.

How is your family finding life in Florence?

We have three children: our oldest son is 12, our middle son is 9 and our daughter will be 6 soon. They’re settled, but it was a bit harder for the oldest. Their mother has been speaking to them in Italian since they were in the womb, so the transition for them was from only hearing one Italian voice to suddenly every voice being in Italian. We didn’t put them into private schools, so they were thrown in at the deep end.

How are you finding integration? Are you integrating more with Italians or the international community?

I’m a chess player. I’ve played chess since I was yea high and there’s an instant community everywhere I go in the world. Here 75% of those people are Italian speakers and they’re great. They’re the core of my crew.

Josh Henderson
Josh Henderson being interviewed by The Florentine‘s Helen Farrell at The Stellar Florence

Is there a chess club here in Florence then?

There are a few chess clubs. The one I belong to is ASD Cenacolo Laskeriano. It’s run by a master and he gives lessons. It’s done at the CPA, the communist stronghold. I had no idea what it was the first time I went there and there were hammers and sickles painted all over the place. But they couldn’t have been more welcoming. We also have Monday play nights at a restaurant in Sant’Ambrogio. We’ve welcomed exchange students and it’s a really good mix of people. Some just rotate in and out. For example, we just had a couple of NYU students who discovered us late in their time here. They just left, but they mentioned to their administrators that any students who play chess should join. Then there are also the core regulars, who are mostly locals.

Tell us about your cookie company Dippin’ Rings.

I previously worked in business at Bloomberg, but I grew tired of the corporate road. I was thinking that I’d like to do something different. My wife’s mother would visit us now and then in New York and she’d make these cookies: ciambelle al vino. They were really good and had a simple ingredient list, but I could never find them anywhere in the States. That set me on this path to figure out if a business would be doable, which resulted in Dippin’ Rings. I was very fortunate that my wife backed me the whole way and I have an incredible business partner, John Kesl, and he’s done all of the magic in the kitchen. He understands all the equipment, which was incredibly complicated. He’s worked with chefs, but he’s actually a trained photographer. Also, the Instagram is done by someone locally. When I moved here, we shifted production and now we ship back to the States. We are looking into expanding into Europe.

That’s one of your jobs. Tell me about your other work.

I still do some consulting in the world of structured finance. It’s a less glorious job, but it pays the mortgage! What is interesting about being in Italy right now is one particular niche in structured finance that I focus on: the packaging of cash flows from solar or renewable energy projects. Italy is certainly a leader in Europe in that area. The financial markets are in turmoil or entering a period of what will likely be severe turmoil, so we’ll see how it shapes out, but I think in two or three years’ time there will be an opportunity for Italy and Europe.

Josh Henderson
Josh Henderson being interviewed by The Florentine’s Helen Farrell at The Stellar Florence

What’s your involvement in the Connect US scheme launched by the US Consulate in Florence.

I already work with some businesses locally, so I wanted to see if I could help. I didn’t necessarily need a formal part in it, but I reached out when I saw the article in The Florentine. I’ve built a network that could be useful for some of the start-ups. What Consul Gupta has done is set up the proper framework. We don’t have to build anything; it’s already there. There’s a very strong expat community here in general: Brits, Americans, many people who have a wealth of business experience. The fact that they’re willing to share that experience with local entrepreneurs is incredibly valuable. It can take many forms: perhaps suggesting what one should pursue, what ideas need to be rethought or recommending how the idea should be presented to an American market, for example. The execution and keeping the energy going will be the most important part.

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