S2 Episode11 - New York New York
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From Brooklyn roots and early heartbreak to the pinnacle of military command and a second act under the spotlight, retired Marine Colonel Frank Cubillo’s life is anything but ordinary.
In this episode, Frank joins us to reflect on his remarkable 37-year journey from an enlisted Signals Operator—toting a powder-blue Samsonite suitcase aboard the USS Spruance—to rising through the ranks as a Warrant Officer, LDO, and eventually Colonel commanding the 3rd Intel Squadron in Okinawa. Alongside his Cold War reconnaissance missions and deckplate leadership lessons, Frank opens up about the personal milestones that shaped him: a four-year pen-pal courtship with his wife Cindy that led to a 50-year marriage, the perseverance required to build their family, and navigating the unexpected moments of parenthood with unconditional love.
Finally, Frank takes us inside his thrilling post-military reinvention. Tracing his path from civil service karaoke nights to center stage as a professional Frank Sinatra tribute artist, he shares what it’s like to swap the uniform for a tuxedo, perform alongside full symphony orchestras, and truly do it "His Way."
www.franksingsfrank.com
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