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Philip Gladstone: A lifelong penchant for learning

Philip Gladstone sees a problem and wants to solve it. When he needed a way to let his chickens out of their coop while the family went on vacation, he designed an automated system to regulate the pen door. When he was curious about what his goldfish were doing in the pond, he installed a camera and recorded video to the Web, before putting video on the Web was commonplace. When he read a story in the press about investigative reporting, he designed a camera that would allow photographers to take photos then get the data out of the country without authorities knowing what the images were. He built a website to track amateur radio signals, and a weather station on his roof and communications network to track weather patterns—and these projects were just for fun. Philip has 30 patents to his credit, many of which are in the field of network security, and “about a half dozen of those are off-the-wall things” to solve a problem that he believed needed solving. It is his intellectual curiosity and penchant for data that has propelled Philip to a successful career while being a truly resourceful man to have around the house.

A history of inventors, and a famous ancestor

Both sides of Philip’s family, the Gladstones and the Goodharts, boasted creative thinkers and inventors, including his father and grandfather who created anti-aircraft gun simulators for training during World War II. “The simulator involved a complicated system of mirrors and projectors that would project the position of a plane onto the ceiling, then the trainee gunner would have to figure out how far ahead of the plane to aim in order to hit it.”

The war provided a different challenge for Philip’s uncle, Nicholas. Nicholas was an engineer who served on a ship stationed in the Mediterranean. According to Philip, the captain had a unique way of dealing with German dive bombers. The captain would ask the lookout man to report the position of the dive bombers, when they began to line up and when they began to dive. When the last bomber began his dive, the captain would suddenly turn the ship and open up anti-aircraft fire. “If you are diving in one direction and the ship starts to move, it is a very difficult maneuver to try to get lined up again. You are also getting shot at, and you only have one torpedo slung underneath your aircraft. The pilot in front has a decision: does he want to go do this all over, or does he want to go home for tea? At that point, he would release his bomb which would fall behind the ship and then fly off. The second pilot would see him and think, ‘this is a good idea,’ so he did the same thing, as would the third pilot. So the ship survives. It was a great tactical maneuver.”

Uncle Nicholas also invented a mirror landing system for aircraft carrier landing to help pilots land safely. Philip said the U.S. adopted the technology almost immediately and the U.S awarded him the Legion of Merit for his system, quite unusual for a British inventor.

Even Philip’s mother worked for the war effort as a member of the Women’s Timber Corps. Due to a shortage in labor and increased demand for timber, women were recruited to locate and mark trees for felling. It was on one of these treks that she found a baby owl that she raised as a pet, and she would often travel with the owl on her shoulder, a sight quite unusual in the 1940s.

Looking back a bit deeper into Philip’s family tree, there is a bit of Parliamentarian history to be discovered. William Ewart Gladstone, Philip’s “three-great” uncle, was a four-time prime minister during Queen Victoria’s era between 1868 and 1894. According to, the elder Gladstone was a Liberal-Conservative who had a talent for oratory, speaking out against electoral reforms and attempting to rescue and rehabilitate London’s prostitutes. Philip did clarify, “At one point, two Gladstone first cousins got married, so I wouldn’t have been as closely related if it hadn’t been for that.”

Boarding schools and unexpected turns

Philip was born in London in the late 1950s, and lived in Campden Hill Square, a steep tree-lined street on the fringes of Kensington and Holland Parks. Philip said “there were a few other kids who lived in the area”, and recalled that “the next door neighbor owned orange groves in Israel and would bring back oranges, which was always very exciting because we didn’t get much citrus in the UK in the early 60s.” Sir Roger Hollis lived on the other side of the square, who Philip said always seemed like some sort of “mysterious civil servant” to him. Years later he discovered that was somewhat true—Hollis served as the head of MI5, the UK domestic counter-intelligence and security agency.

Philip said he was enrolled in boarding school on the south coast of England when he was seven. He explained that the school had a “curious grading system where math was graded in one bucket and everything else was graded in another bucket, and they had about equal weight.” Philip excelled at math and came in regularly at the top of his class. Everyone in the school knew it because the headmaster would announce the rankings every few weeks over the loudspeaker, “And first, Gladstone.”

Philip explained that his father was a heavy smoker, and passed away from leukemia when he was just 11. Since he was away at school, Philip learned about his father’s death from the headmaster and did not attend the funeral. Soon after, his family moved from London to a small village in the English countryside where his father had grown up. His parents had chosen the house together, and his mother went ahead with the move despite his passing. She remained in the home until she passed in 2020.

Philip attended Eton College, a prestigious UK boarding school for boys ages 13-18. “My father went to Eton so it was expected that I would go, and my name was probably put on the list at birth,” Philip quipped. Students at Eton wear traditional uniforms with wool waist coats and stiff collars. “When you became a prefect, you graduated to a bow tie, and other students would come up and try to untie your bow. You had to learn to tie a knot away from the mirror VERY quickly,” he recalled.

While at Eton, Philip discovered the school had a computer, one he describes as “maybe six feet long by four feet high by three feet deep, with a ten-character per second printer.” One of Philip’s first projects on the computer was what would now be called a graphing calculator. “You could type expressions and plot them rather crudely on a teletype printer in roughly the right place,” he said. “In the mid-1970s, a student could only buy a kit to assemble a Sinclair pocket sized calculator. It was a remarkable piece of technology and only cost £50.”

After Eton, Philip went on scholarship to Trinity College, Cambridge, as his father had before him. While at Trinity, Philip admitted to spending too much time on the computer and not enough on math, but graduated in the requisite three years. During summer vacations, Philip worked at Rutherford Appleton Laboratory which had won a government contract to provide interactive computing to universities. “Up to that point I had only really done batch programming—I fed cards into a card reader, waited for the printout, discovered a typing error then had to go back to the beginning.”

“We had to build a network to connect systems since there was no Internet yet,” Philip explained. “For a young guy it was a real blast. I met interesting people and traveled to obscure universities to install systems. I remember one university where the machine room was below the chemistry lab and we had to put a corrugated plastic roof over the computer because occasionally the chemistry lab would overflow and noxious chemicals would drip through the ceiling.”

Navigating a career through start-up companies

After graduation, Philip joined a start-up company that tracked data on pollution requirements. “There were all sorts of government requirements on polluters like mines and chemical factories, and many companies initially said yes to us developing a system to monitor that data. We soon discovered, however, that no one really wanted to buy it. What we realized was that the current manual process of charting wind direction, wind speed and pollutants was tremendously difficult for inspectors to decipher. With our system, inspectors could type in queries to understand precisely the maximum amount of pollutant for the wind direction, which was precisely the information the company did not want to know. The only people we sold the system to was York Cathedral who used it in reverse—to prove that a particular polluter was the reason all of their stone was falling out.”

Philip’s next venture was to set up a new development lab for Data General in Europe. He grew the lab to nearly 50 people, but was eventually laid off during an economic downturn in the early 1990s. “Because I was an architect there, I had spent a lot of time in the Westborough offices, so I knew all of the people in the Communications Systems Group. A small group of them had gone off on their own to create a new start-up and asked if I wanted to join them. I really didn’t want to look for a new job in the UK, so I agreed to come to the U.S. for 18 months.

Philip came to the U.S. on an H1B visa to work as a consultant with the intent “to build up a war chest of cash, then reinvest in ourselves so we could build a new product and make ourselves fabulously wealthy.” He admits it was a great plan, but it never transpired, and eventually they all left the company. The position did require him to commute frequently to New York City.

“All of the flight attendants were regulars so I got to know them,” Philip recalled. “They’d point out things like, ‘oh, you do know that you haven’t taken the laundry tag off the back of your suit!’”

Another kind of start-up

When he went home to England for Christmas in 1991, Philip recalled there was a big snowstorm. “I was sitting next to a woman at the airport and we got to talking while she was waiting for her flight. We exchanged phone numbers. When I got back in January I called her, and she asked if I could find a date for her friend so we could all double date.” Philip brought along a friend, and the four of them went to see Shirley Valentine. They all got to be close friends, and when the woman eventually dumped Philip a few months later, he turned his attention to her friend, Peg. “About a year after I started dating Peg, she finally realized I was interested in her and we started dating properly,” Philip laughed. The actual courtship was brief and the couple married in 1996. Daughter Catherine arrived in 1997 and Jennifer followed in 2000.

Philip started work at Raptor Systems in 1995. After Raptor went public, it was bought by another company, around the same time that Philip discovered that the CEO of Raptor was doing another startup, so he jumped on board. While at Okena, Philip worked on developing intrusion prevention software, and architected, designed and implemented the Okena StormWatch product. Cisco Systems bought Okena in 2003, and Philip moved to Cisco to continue to manage the Cisco Security Agent (the old Okena StormWatch product).

Another move and a new home

While the couple had purchased their first home in Framingham a few years prior, they began a year-long search to find a new home for their growing family. Carlisle was not on the original list, mostly because they were looking for a home closer to the Cisco campus in Boxborough. When they couldn’t find the perfect fit, they expanded their search and eventually purchased their home on Curve Street.

Philip worked at Cisco for nine years as what is known as a “distinguished engineer” in the technical ranks. During this time he did quite a bit of patent work, nearly all of it pertaining to computer security. By coincidence, Philip ran into the CEO who had started both Raptor and Okena while having dinner in Sudbury. When he mentioned opening a new start-up, Philip agreed to join him once again. “While I understand that past success doesn’t necessarily lead to future success,” Philip explained, “in practice, past failure does lead to future failure.”

The CEO started BitSight, a cybersecurity ratings company that analyzes companies, government agencies, and educational institutions by looking at their security practices. When he arrived at BitSight, “we had 400 square feet of incubator space at One Kendall Square and there were maybe five employees. Now we are close to 500 people and have offices at the Prudential Center.” Recently BitSight received a $250M investment from Moody’s and acquired VisibleRisk as part of what the BitSight website describes as “a landmark partnership that will transform the way that the global marketplace measures and manages cyber risk.”

Philip is excited and optimistic for the future of BitSight. “We are still getting the word out, and the company is still primarily U.S. based,” Philip explained. “Because we are creating a market, it’s difficult to know the value of the market. Once everyone believes they need our service, the company will become valuable.”

Problem solving doesn’t stop at the office

So what does a Chief Architect do with his free time? Philip has a few diversions, including weather reporting, ham radios, model trains, cactus gardening and antique clocks.

On the weather: Philip explained that his maternal grandfather had a keen interest in weather, and manually collected and recorded rainfall measurements for nearly 50 years. Philip has the weather gene himself, and has made it possible for weather observers from across the country to automatically and accurately report data from their personal weather stations to NOAA via the Citizen Weather Observer Program. “It became clear that when I looked at the data files that much of it had been transcribed from handwritten cards and the data was not always accurate.” The data collected is used by federal and local agencies, colleges, universities and research firms to improve warnings for hurricanes, storms and floods. In 2008 Philip was honored as a National Oceanic and Atmospheric Administration Environmental Hero for his efforts and still maintains the weather station perched on the roof of his house.

On the airwaves

“When I got interested in amateur radio, I thought it would be nice to know how far your signal gets,” Philip explained. “If you send a message and no one gets back to you, you don’t really know who received the message. Is that because they don’t like you, or because your antenna is broken, or the signal only got to end of your property? I thought it would be cool if people running decoders for digital signals would actually report that they did hear you even if they weren’t that interested in responding.” Philip built a website for people to enter their data that became popular and now gets about 500 reports/second ( “People on YouTube even make videos about how to work it,” he said. “It’s all very cool but the site always goes down when I am on vacation!”

On the tracks

Years ago Philip discovered a locomotive called the Gladstone, a steam engine from the end of the Victorian period. According to Philip, William Stroudley designed it for the London, Brighton and South Coast Railway and always named engines for people who were prominent in the day. “I think he truly understood the value of marketing and how to get funding!” In 1959 the Gladstone was given to the British Transport Commission, repainted in its original coloring and is on display in the National Railway Museum in York, England.

Philip bought a private collection of trains, track and controllers from a seller in Billerica that reignited his passion for model trains. He managed to build a train table in the basement a few years ago, but admits that it will take some time to clear off the treasures that have accumulated there before he can set any trains out on the table.

On the clock

Philip said both his father and a cousin built pendulum clocks designed to be very accurate. “My father built clocks to be accurate within 1/10 second per day which is very good,” he reported. Several years ago, Philip and Peg purchased three inexpensive antique English clocks from Skinners Auction House dating back to the 1790s, one of which he has had time to refurbish and get running successfully. ”For a time I was monitoring every tick to see how much time the clock was gaining or losing, the effect of temperature, and the effect of the position of hands. The clock runs slower when it is trying to lift up the minute hand since gravity plays a subtle effect.” He bought a Station Master clock powered by electricity for comparison, which he said has similar inconsistencies in relation to the position of its hands. “I suspect the people who built these clocks didn’t actually know this stuff because you need fairly accurate modern equipment to see the differences in a micro-second or two on each swing.”

Planning the next adventure

While Philip is hesitant to discuss what the future will bring, he does look forward to the day when he and Peg can resume their travels and spend more time pursuing some of his favorite hobbies. This summer they drove cross country to deliver a car to Jennifer, who is a senior at the University of California in Santa Barbara. He enjoyed the freedom to travel free of a strict schedule and “the unexpected things you find along the way when you are not in a huge hurry. For instance, discovering that some bikers we met in Sturgis, South Dakota, when they are not being bikers—they are software engineers.” The couple would also like to visit New Zealand and Australia, perhaps India and Argentina, and the Antarctic.

Philip is not entirely sure how his life would have been different had he chosen to remain in the UK, but surmises that he likely would have taken a much more traditional work path. “The climate for start-ups in the UK was poor when I was younger, but it has improved,” he said. “It’s mostly about attitudes. Attitudes are improving but it’s still not the same. In the U.S., if you talk to a truck driver, they want to own their own trucking company. In the UK, they are happy being truck drivers.” Philip is certainly the master of his own truck, and his adventures continue to be written.

Published October 13, 2021 in the Carlisle Mosquito.

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