Mom of the Week – Cindy Milazzo, Gallery Owner & Entrepreneur

Mom of the Week – Cindy Milazzo, Gallery Owner & Entrepreneur


What do you love to do with your children? How old are they? And what is your greatest wish for them?

I have 2 sweet boys. Sam is 14 and Owen is 10. We are an active family in the winter and summer time. The winter sport of choice is hockey. I enjoy watching them practice and play. Sam introduced us to this sport, as neither of us even watched hockey growing up and now watching them and professional teams play is one of our favorite things to do as a family. Snowboarding is another wonderful sport I enjoy with the boys. Both boys started boarding at 5 and now beat me to the bottom handily. Summertime is my favorite however. Sam has taken up surfing and it’s quite nice to sit on the beach and watch him catch waves with his Dad. Owen is starting to surf too, so this summer will really be fun!

I love watching Owen draw and paint. I can see the wheels turning as he masters a piece… It’s been wonderful seeing his affection for art grow.

My greatest wish for Sam and Owen is that they grow up to be kind, honest, loving, hardworking and passionate young men. My hope is that they focus on who they want to be and less on what they want to be, as that will follow with genuine effort.  A sense of humor is also key! 

Who has had the biggest influence upon you?  

My mom had the biggest influence on my life. She had me when she was 18 years old and found herself a single mom in Oklahoma City a few years later without any support from my father. Being a divorcee was already quite a hurdle at that time. Raising a child alone on a single woman’s salary in the early 70’s was not easy but she never gave up and always tried to be there for me. The quality I admire most is her yearning to always become a better person. She’s forever trying to improve on herself emotionally and spiritually. Her work ethic is incredible as well and I wish to pass on all of these fine qualities to my children.

What quality do you most admire in a mother?

Mothers who manage to keep their calm under extremely uncomfortable situations! I can remember Sam throwing himself on the ground in a full on tantrum at the A&P and thinking, what the heck do I do now? I was furious, embarrassed and was holding on by a thread. I was on the verge of making a complete spectacle of myself until this kind mom came up to me and said, “Hey, we’ve all been there, my child did that last week.” That mom has no idea how much that helped me calm down. At that very moment, I was able to gain composure and remove my screaming entitled little monster child from the store.

Besides motherhood, what other careers/opportunities have you enjoyed? And what are your strongest qualities? 

Boy, I’ve had a lot of different jobs and opportunities since I moved to New York City, then Hoboken, NJ and finally Greenwich, CT. My first job was at an advertising agency, Ketchum, which I grew out of fairly quickly. My plan was to go back to school eventually; however, I could barely afford to live in the city much less pay for school, so I took an entry level job at the American Stock Exchange in Marketing where they offered business courses. Though I enjoyed learning about the stock market and business in general, I was missing a creative outlet. While living in Hoboken, NJ I realized there was a huge need for a retail store for young, hip, artistic professionals. Growing up without a lot of money, I frequently visited antique and thrift stores for clothing and furnishings and decided to dovetail this love of history, design, and fashion into a business of my own. In 1990 a friend and I pooled all our resources and opened a business together selling mid-century furniture, vintage clothing and jewelry. While I loved this business, it was not very lucrative so I took a job with an auction house in conjunction with my business. I ran auctions for 12 years while keeping my small business running most of that time. It was a lot of work, but both industries complimented each other. In 1997, I met my husband, Lee, who was also an entrepreneur. He founded Poster Conservation in 1993, which restores roughly 150 vintage posters weekly. After we had our first son, Sam, I started working for our family business and found the flexibility to work and be a mom worked well (most of the time). We have grown our restoration company and introduced Samuel Owen Gallery after Owen was born in 2006. We now run a Gallery in Greenwich, CT and in Nantucket, MA. 

Were you happiest in elementary, middle high school or college? Please explain why. 

The last year of college was my happiest. Oklahoma was a rather conservative place to grow up and I finally stopped worrying so much about what others thought about me. It was liberating. 

What do you like to do for fun and what is your idea of a perfect day?

A perfect day for me is on Nantucket. Coffee at the Handlebar Café, a trail jog or yoga class is mandatory. Perhaps hitting a good thrift store or estate sale, and then watching Sam, Owen and Lee surf or Owen paint. Nautilus or CRU for a delicious dinner is a nice way to end the day.

What is one of your favorite books? Movies?

Sadly I haven’t had any time to read or watch movies lately. I’ve always been fond of non-fiction books. I enjoyed Eleanor Roosevelt by Blanche Wiesen Cook. I’ve been wanting to re-read Huckleberry Finn and Tom Sawyer by Mark Twain with the boys. I love his sense of humor. Now keeping in mind that I haven’t seen any movies lately – The Big Lebowski, and The Godfather series are a few favorites. I can watch It’s a Wonderful Life, Christmas Story and Elf every single year. 

What is your favorite type of food and what do you love to cook?

I love to cook Mexican food! 

If you could go anywhere in the world, where would you go? 

I’m dying to go to Italy!

Where is your favorite place to Party with Moms and what’s your drink of choice?

L’Escale or Bar Taco on a sunny day is a good spot for a Mom’s night out. My favorite drink is a dirty vodka martini or a margarita! In fact, I wish I was remotely holding either one right now.  



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