Angela Massaro-Fain

Born and raised in New Jersey, I grew up in an Italian household. Life was fun, loud, full of food and love. I was a tomboy, however, my Mom thought dance lessons would give me grace. She made sure I had an incredible education and a great work ethic. She was the single most influential person in my life.

After I graduated college and worked for a half a dozen years in my field, I moved to Montreal, Quebec Canada at 24. I speak two languages fluently and one – I knkow the basics, order off a menu, order a good bottle of wine, ask directions, and swear!

I started my first business, Grapevine Communications, in 1988. I successfully sold the business to a publicly-traded company, after a decade in 1998, and relocated to Lakewood Ranch with my daughter.
In 2000, I restarted the business with my husband, John and we grew it to be the largest and most award-winning full-service Advertising, Marketing & PR firm in the region. In 2017 we sold Grapevine Communications to one of the most widely respected businesswomen in the area – Allison Imre Perkowski. She is an honest, loyal friend, smart and business savvy – and I am always so in awe of this powerhouse of a woman.

Throughout my business caree,  I was heavily involved in leadership positions in the non-profit arena.
In 2011, I founded Sisterhood For Good (SFG), a women’s giving circle, with nine other original members. SFG grew our all-female membership and held fundraisers with the sole Mission of assisting our community through an Annual Grants Program. In 2018 SFG became a 501(c)(3) public charity because of the dedication of our membership – which is currently 152 members. I have stepped down as the volunteer Board Chair after 9 years, yet still remain as the volunteer Company President and sit on the Advisory Board. I don’t ever plan to leave.

Anyone who knows me, knows I’m a DOER – I just can’t sit still.
I have a few hobbies: travel, collecting art, and cooking.
The former is on-hold due to international travel restrictions brought on by the recent healthcare concerns.
The latter has resulted in me writing a cookbook “Bacio di Cucina”. It means “Kiss From The Kitchen”.
I am currently teaching cooking classes for free at my home and finishing up the cookbook.
Once that is printed, I’ll be selling it with a portion of the proceeds going to Sisterhood For Good.

I am married to the love of my life, John Fain. He is my sounding board, my biggest cheerleader, and calls me out to keep me grounded and real. He taught me how to trust, and I love him more than I could have ever imagined. We will celebrate 20 years married in September. Most people know I call him the #HandsomeOne – because he is!
I’m also the very proud Mom to Maria-Francesca. She is a college grad and returned home after college to work in her field as a graphic designer in the Corporate Communications Dept. at FCCI. She is very talented and is the joy of my life.
I have four of the BEST Grandchildren EVER!

Q: Please tell us a little bit about your family.
I’m from an Italian family where life was fun, full of food and love. I never had any privacy.

Q: Please tell us about your current, past, or future career. What do you love most about what you do?
I have transitioned from a serial entrepreneur having founded and sold two businesses, to a hopefully successful author with my upcoming series of cookbooks (3 are in the works!)

Q: What are a couple of your favorite restaurants in our community?
Michael’s On East – #1 for sure. Yummy House, and I like a good Taco every once in awhile – so we go to Poblano’s. We run the gamut.

Q: How long have you lived or worked in our community?
I moved here in October 1998. You could not get me out of here with a bomb – or a hurricane!

Q: Who is the most interesting person you’ve met here in our community?
Terri Stern – she is one of my closest confidants and partners in crime. She is wickedly smart, full of empathy and a survivor in many ways. I respect and love her so much. She has made a big impact on my life.

Q: If you could travel anywhere in the world right now, where would it be and why?
We had to cancel our trips to Scotland and Ireland due to the international healthcare concerns, so I would like to get there in the next year. My next “bucket list” location is Australia & New Zealand.

Q: What is one of your favorite movies? TV shows?
I’m a sucker for a good RomCom – so my favorite here is Notting Hill. I’m still an action-junkie – so any Jason Bourne, Mission Impossible or John Wick series is perfect for me.

Q: What advice would you give to people?
Start saving young, buy what you can afford and still ENJOY LIFE. Travel. Rely on your own strength and stand on your own; you never know what life will throw at you. Be strong and remember that you CAN DO IT. Get up if you fall down, have your cry and then dust yourself off and be a winner!

Q: What is something on your bucket list?
Live on the water – but my husband John says it’s too much upkeep.

Q: What is your go to band when you cant decide what to listen to?
I have SO MANY – music has been a BIG part of my life since I was a kid. My absolute FAVORITE, don’t laugh is Tom Jones. What’s New Pussycat!

Q: What current or former local business makes you the most nostalgic about our community?
The Players Centre of Performing Arts. They just celebrated 90 years here giving back, entertaining and making a difference in our community.

Q: If you could choose anyone that is alive today and not a relative; with whom would you love to have lunch? Why? And where locally would y’all meet for this lunch?
President Donald J. Trump. Why – because while he may not always be eloquent when speaking, he is a fighter, a smart business man and has endured so much in the past few years. I love a survivor.

Q: What is your favorite thing or something unique about our community?
Everything is here: sun, sand, the arts, so much to do; I have never seen a community as generous and sincere as Lakewood Ranch.

Q: Where do you see yourself in 5 to 10 years?
Still traveling, while holding my hubby’s hand and laughing.

Q: (Even for friends or family), what is something interesting that most people don’t know about you?
I won a few beauty pageants back in the day. One of my favorite awards was for “Poise & Appearance”. Now I fall down in heals higher than 2 inches. My husband laughs at me all the time. GROUNDED – literally!

Q: What is the most beautiful place you have ever been?
South Africa on Safari

Q: Favorite month? favorite holiday? and best single day on the calendar?
Favorite Month: December. Thanksgiving is my favorite holiday becuase we get so many friends and family who come together to share love and laughter. Best day, hands down is January 20th which is when my daughter was born.

Q: What would you rate a 10 out of 10?
A great meal with friends, good conversation and wine!

Q: Who inspires you to be better?
My mother. Even though she is watching me from above, she has always been my barometer. I try every day to make her proud.

Q: What is one or two of your favorite smells?
1) Fresh cut grass. 2) The aroma wafting through the house of freshly cooking Italian Sunday “Gravy” (aka spaghetti sauce).

Q: Finally, what 3 words or phrases come to mind when you think of the word HOME?
Love. Safe. Laughter.