Written by Kayla Schmidt
Yorktown Heights resident Josephine D’Ippolito is the chief operating officer at Griffin Strategies, a financial investigations firm in White Plains. She is also a freelance writer for this very magazine, very active in our community and says she loves all things local.
Why did you want to be a judge?
I’ve been a northern Westchester resident all my life, and I’ve seen it evolve. I’ve seen so many small businesses come and go, so I saw this as a way to celebrate the wonderful businesses we have in northern Westchester.
What’s your professional background?
I’m a freelance writer and a COO for a financial investigations firm. My professional background is really in finance and operations, but because I’ve lived in this community my whole life, I’ve done a lot of community service, both when I was young and as an adult. I volunteered at the hospital and have had multiple jobs in the community. So I’d say I’ve worn many different hats when it comes to community service.
What perspective did you bring as a judge?
While my professional background is very finance-oriented, all of my interests are lifestyle-based. I love going out to dinner, cooking, designing and anything aesthetic. I brought a perspective as someone who was really excited about things that are really well done.
What did you expect as a judge?
I’m excited to see who the community chose as their favorites and to read everyone’s comments. I’m expecting some new places to visit, especially anything food-related, because I’m a huge foodie, and I have even contributed recipes to this magazine. Also, I’m excited to learn about anything artistic or any cultural attractions.
What kind of judge are you?
A fair one, just as all other judges should be.
Which famous judge best matches your personality?
I think Gwyneth Paltrow is a judge on a new reality show for small businesses, and I just think so highly of her aesthetic, so I’d choose her.
What was the biggest challenge as a judge?
I wanted everyone to win, so it was really hard for me to discern between a bunch of really good nominations.
Last question: Who would make a better judge, Leonardo DiCaprio or a dog?
A dog. Anyone over Leonardo DiCaprio.
This article was published in the January/February 2025 edition of Connect to Northern Westchester.
Kayla Schmidt
Kayla Schmidt is a freshman at Horace Greeley High School. She is part of the newspaper and the SADD club, and she is also the co-manager of the track team. In her free time, Kayla enjoys spending time with her friends, family, and dogs, along with reading (preferably on the beach).
