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Tom Ossa

@tailspindrum

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Awesome night seeing The Diary of Jonathan Harker on Bannerman Island. Live outdoor theatre, boat ride, fall weather, snacks, and all the Dracula vibes. Welcome, spooky season. We've been waiting for you. 🧛🍂🎃🍎

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Random assortment upload: summer neighbors, Kobe dinners, Norcina drinks, breakfast of champions

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In this episode, we sit down with Rockland County businessman, entrepreneur, musician, and community advocate @tailspindrum Tom Ossa to discuss his journey and his perspective on the future of Rockland County.

Tom developed his business acumen growing up around his family’s bike shop. In 2007, he launched his first business, Rockland Web Design, and later purchased the domain name RocklandNews.com for $4,300, creating a platform focused on covering local stories without bias or personal opinion. Today, RocklandNews.com is adapting to the rapidly changing media landscape and exploring how artificial intelligence can shape the future of local news.

Tom’s life has also been shaped by personal tragedy. At age 12, he lost his father, who was killed by a drunk driver while changing a tire. As a shy child, Tom found an outlet in music, eventually becoming active in the local music scene and organizing events and festivals that raise money for local charities.

Deeply involved in Rockland County’s nonprofit and community organizations, Tom offers a unique perspective on the challenges facing the county.

We discuss Rockland County’s biggest issues, the future of local journalism, the role of nonprofits and businesses, artificial intelligence, and where Rockland County is headed in the years ahead.

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Keepin' it weird with Al.

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God Bless our Anthony Joseph on his First Communion Day ✝️ so proud of you ❤️
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#firstcommunion #ajm

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An abbreviated version of the Stony Point Seals event this year. River is too frozen and dangerously cold for anyone to plunge this year. 🥶 But funds were still raised for some very deserving kids, and that's what it's all about.

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Had a great time, despite the frozen toes, watching the Giants kick some Cowboy keister. Even though they had a crap season overall, this was a great game, and a great way to kick off 2026. Go, Blue! (Coincidentally, underneath that scarf, Tom was also blue.)

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Lovely Christmas decorations at Lyndhurst Mansion

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Fall vibes activated

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Had an amazing day on Sunday at LARC in the Park, raising funds for the Library Association of Rockland County. I got to be everyone's cheerleader as the LARC lark! Shout out to my amazing husband for his assistance as sound engineer, and congrats for running a stellar 5k, just because you can. #libraryassociationofrocklandcounty #larclibraries #librarylife #rocklandcountyny

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🎶 Rockland Music Fest 2025 was pure magic!

From the incredible music to the stellar face painting, fashions, dance moves and more—as well as Tom’s unforgettable lil’ leg kick move/photographic pose (😂)—this weekend was filled with joy, positive energy, and community spirit. Every artist, vendor, volunteer, sponsor, staff, food truck operator, open mic participant, and attendee brought something special to the day filled with music and great vibes. 🎸

We’re proud that funds raised will benefit Meals on Wheels Rockland, making the celebration even more meaningful. ❤️

There were so many amazing moments throughout the festival — and these photos are just from the earlier festivities of the day! They only capture a small snapshot of all the action, but we hope they give you a taste of the energy and love that filled the air. Stay tuned to see more, and to learn more about next year’s festivities—we can’t wait to do it again! 🎤🥁🎹👨‍🎤

#RocklandMusicFest #MealsOnWheelsRockland #FestivalHighlights #CommunityLove #LiveMusic #GoodVibes

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I get my flowers 💐💐💐🥕

This pass weekend #teamak40 reached another peak…we did the Clover stadium…

He performed and rock that stage like it was Wrestle Mania but this was the @rocklandmusicfest in his home…

After the performance we went back to our suite and he gave a toast to me…Big Vegg🥕

Surrounded by friends and family…

What he(Ak40Devin) is saying is true…definitely that day one guy…

You look up loyalty in the dictionary and Ull see a picture of me with a fedora and African medallions on…

Im more than his manager im his best friend & good friends look out for each other…

This is how you truly Pass the Torch🔥

Moment caught📲 for infinite replay by My turtleete🐢🎀🐢🥕 @jennrockofficial

It’s #teamak40

It’s #Teampassthetorch🔥

It’s #team845vians

& it’s definitely #sumthinnserious🔥🔥🔥🥕

#videography #photography #dopemoment #Gametime2025 #mytime #viral #success #radiostation #internetradio #media #connection #rocarazzi #verticalvideo #allthewayup #cantlose #legendinthemaking #movie

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