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Escape From New York: How A Tech CEO Found Freedom in Florida

Spencer Kupferman, CEO of cybersecurity company PKWARE, couldn’t stand to see how New York’s draconian COVID measures were hurting his children. He took his family and left for Florida, never looking back.

MIAMI BEACH, FLORIDA — Spencer Kupferman is more than happy to be in Florida. He was born in Raleigh, North Carolina where he went to high school, and when his career took off, he moved to New York City. He’s been in the software industry for almost three decades and is currently running cybersecurity data protection company PKWARE, which is based in Milwaukee, Wisconsin. PKWARE’s products are used by many of the world’s largest banks and financial service institutions to protect sensitive data.

When COVID started, the Kupfermans were living in Westchester, New York. Spencer Kupferman saw his young children in front of computer screens for hours upon hours and started worrying about their mental health. The family had a place in Bal Harbour, Florida, so they escaped down South at the very beginning of the pandemic to get away from the draconian measures that were enacted by (now former) Governor Andrew Cuomo in New York.


“We stayed in Florida for months in 2020, then we went back to Westchester so that the children could get back to school. But it was really, really bad… I felt helpless seeing my children in this impossible situation. My concern wasn’t so much the present, but how this would damage them in the future. Looking at them suffering, wanting to learn, craving human interaction… as human beings, we must have human interaction. So, the fact that all these things trumped the human element for those in charge… the future of humanity is always the next generation. It was an extremely disturbing time for me and my wife, and many others that I know. Seeing my son walking around with a mask inside of our house, having been told to do this in school. It was infuriating and debilitating. It was completely Orwellian,” he says.

In August of 2021, the Kupfermans had had enough. They sold their house in Westchester and headed for Florida. Since then, they’ve liquidated all the New York real estate that they had accumulated over the years – including a Manhattan apartment. The only thing left is their house in Southampton, NY, which is being placed on the market.

“In New York, even today, they keep trying to come up with different kinds of unconstitutional laws, including a federal judge who had to bar the state of New York, at least for now, from enforcing the part of a closely watched gun law that bans legally owned and licensed firearms from churches, synagogues or other places of worship. They’re obsessed with controlling the population, motivated by an agenda that requires the government to impose their will over every aspect of your life. When DeBlasio became mayor, we were living on the Upper East Side. The city quickly started crumbling with crime and homelessness. New York was going to hell in a handbasket. The new bail law was neutering judges’ ability to enforce the law and keep violent criminals off the streets.  DeBlasio was trying to stymie every chance at prosperity and brought measures that were obviously designed to hurt businesses and job creators,” Kupferman explains.

“The best thing that’s happened in New York since I left for Florida is the Giants and the Jets both having winning records at the same time,” he jokes. “There are multiple reasons why New York has the highest population loss of any state in the country – it’s a very sad situation for what was once one of the greatest places to live in America.”

During COVID, Spencer Kupferman regularly commuted between New York and PKWARE’s headquarters in Milwaukee.

“There was something I experienced during that time that shook me to my core. Andrew Cuomo, who was governor at the time, had placed Department of Health officers and National Guardsmen in uniform at the airports. When we landed at LGA or JFK, DOH Officers would hand out forms to fill out where you would be staying, all your personal information… and on the back of the form was a statement that if you provided false information or if you didn’t comply you would face stiff penalties and possible arrest,” Kupferman says, and continues:

“So when we landed, the Department of Health people had their badges out, pulling people out of the line and barking at them. To be in New York, the most progressive and liberal place on Earth, only to be met with soldiers in uniform… wanting to know where you lived… wanting your phone number and intimidating the passengers? Many times, I would just keep on walking. But a few times they got me. It was a scary and humiliating experience and totally unnecessary.  It represented the worst of government overreach and abuse of these institutions. Using valuable taxpayer resources to harass, harangue and intimidate innocent people. But the scariest part was how many people just complied. They were like sheep. Many legal scholars to this day argue that this approach was totally unconstitutional. Then I realized that it was this type of mentality that was a slippery slope for the government and could lead to other dangerous outcomes… When you start the process of dehumanization of an entire group of people, this happened in a big way during the height of the pandemic. Throughout history we’ve seen what happens when groups of people are singled out and discriminated against for race, religion, sex and so on. It’s never a good ending for society if this happens. World War II gives modern history it’s most potent example.  That experience in those airports was the darkest moment I ever had as an American,” Spencer Kupferman tells The Florida Standard.


Spencer Kupferman is one of few tech CEOs who’s decided to be outspoken about COVID measures, the current state of America and the Western world, as well as the psychological warfare that leaders have unleashed against their own populations.

“It’s a great brainwashing machine that’s going on in this nation and the entire West. Some countries in Europe are farther gone than we are when it comes to losing their freedoms and all the things that we hold dear. I’m very scared that we’re going backwards in history. We have to stop the Left’s divide and conquer agenda. They pit rich against poor, black against white, vaccinated against unvaccinated, and so on… it’s the type of stuff that they did in the Soviet Union. The Left thrives on chaos because it makes people take their eye off the ball and become distracted. They’re trying to import this agenda to America, and we have to stop it. We have to stand up and call it out,” Kupferman says.

“Regarding COVID, sure – it is a real virus, but the measures taken were completely off the charts. Shutting down the country obviously hurt more than it helped. With these measures, they’ve potentially ruined an entire generation. Look at the alcoholism and drug abuse, the mental health issues, domestic violence and suicides caused by these lockdowns. If the people in charge were true humanitarians – like they claim to be – they would’ve had compassion for people. Instead, they instituted these authoritarian, draconian policies that destroyed individuals, families, communities and businesses.”


Spencer Kupferman is also critical of where education is heading in America – including the emergence of Critical Race Theory.

“It’s outrageous to make children somehow guilty for the color of their skin. To scapegoat a six-year-old child and make them the villain  for historical events they obviously had no part in whatsoever…  This is not the America that I grew up in. It’s not the America that my father served as a U.S. Marine together with every minority under the sun. This is not what our country is about. Yes, we need to teach accurate civics and history to our next generations, slavery, Holocaust education the Civil Rights movement, but to spin America as a racist ill-conceived entity is flat wrong and total distortion of truth. We are the most generous nation in the entire world, it’s not even close. That’s exactly why minorities from around the world are in line trying to enter this country. To experience the same American Dream my family lived when my grandfather came to this land as an Austrian, Jewish immigrant. Unfortunately, with policies like CRT, I fear this American Dream we speak of and chase will turn into the American Nightmare for the next generation. We have to get back to opportunity and meritocracy, to treat every human being with equal respect and dignity,” he says.

Spencer Kupferman says that what we really have to do is to hold our politicians and other leaders responsible for their actions – something that’s completely missing today.

“We must have accountability. For example, in New York, Andrew Cuomo sent people to their deaths in these nursing homes. Then he had to resign because of sexual harassment accusations. Where’s the accountability for the nursing home scandal, for the families of those affected by his incompetence – where’s their justice?” Kupferman wonders.


Spencer Kupferman says that Florida Governor Ron DeSantis is a big reason why he moved to Florida.

“I actually think that DeSantis represents something that goes way beyond party politics. He’s an outright fighter for freedom, meritocracy and fairness. He’s proven himself through all of this… how he’s been standing up against the media, against a vicious cabal that’s been trying to take him down… for what? Because he kept Florida free and open during COVID? Because he’s created the largest budget surplus in Florida’s history? His policies have helped the regular Floridian when other politicians have taken people’s liberties away and made them live off of government handouts. I think Ron DeSantis is the future of the conservative movement. There are many who call themselves conservatives or Republicans, but many of them are frauds. DeSantis represents a new type of American realism, and now he’s made Florida the paradise of this nation. He’s lifted thousands of people up, and I don’t think the ceiling for him is the governorship of Florida,” Spencer Kupferman says.