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I’m a software engineer and entrepreneur focused on modern web technologies and AI.

Here's an ongoing autobiography, which also shares the story of my by-the-bootstraps "unschooling" education: now the subject of a chapter on grit and resilience in the bestselling book Mindshift by Barbara Oakley.

An angel investor once described my core soft skill in the role of founder or early team member as: "The ability to perceive exactly what needs to be done. And then to do it."

My experience working in difficult environments around the world means that I can be trusted to get things done, even when things go wrong.

In the past, I coined the term "Startup Cities" as co-founder of StartupCities.org and a startup spinoff, both of which focused on why startups should build cities. I now write about Startup Cities at StartupCities.com

I've won several awards for economic research and have been published or interviewed in Virgin Entrepreneur, a16z's Future.com, The Atlantic's CityLab, Foreign Policy, and in academic volumes by Routledge and Palgrave MacMillan.

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Eulogy for an Engineer

My father, Sheridan Caceres, died on November 1st, 2021 of health problems accelerated by COVID. His life reads like a history of the 20th century's most pivotal events. From Pearl Harbor on Hawaii to the Cuban Missile Crisis, to the Apollo 11 mission, to the early days of Silicon Valley, this is his story, as best as I can recall it.

Sheridan was born in Hilo, Hawaii in 1938. The United States still languished in the doldrums of the Great Depression. It's hard to understate Hawaii's remoteness in this era. It was still a territory, an exotic remnant of 19th century American expansionism.

Television, with only one grainy channel, would not arrive for another 15 years. Children often wore no shoes. Some of our Native Hawaiian relatives alive in those days grew up in thatched huts. One or two generations before, the branches of our family tree disappear into question marks and indigenous names, often without any legal surname.

I know little of his parents. The only stories I've heard were of neglect and drunken abuse. Perhaps this is why I never once saw my father drunk. As a young man, he was skinny and quiet. He grew a love for short-wave radio — a window to the outside world. As a teenager, he DJ'd the hits of Elvis. His love of radio lasted a lifetime.

My father operating an early recording rig in high school

My father operating an early recording rig in high school

Pearl Harbor broke the islands' idyll. Upon hearing news of the attacks, furious locals grabbed hunting rifles and sailed off in fishing boats, hoping (somehow) to hunt down Japanese ships and submarines. For weeks funeral dirges rung through brass instruments as processions for dead sailors marched by his house each day.

My father poses with the first car he ever bought, circa late 1950's.

My father poses with the first car he ever bought, circa late 1950's.

Hawaii's role as a forward base in WWII forever changed the island. At only 13 years old, my father's first experience driving occurred behind the wheel of a WWII-era Navy Weapons Carrier truck. At 18, he enlisted in the Army. Hawaii has long melded cultures and ethnicities: Filipinos, Chinese, Japanese, Americans, and Native Hawaiians and other Polynesians. My father's own bloodline (and my own) includes Chinese, Portuguese, Hawaiian, Spanish (home of the city "Caceres"), Chilean, and other ancestors. Hawaii's melting pot is on full display in his Army unit, sourced from Hawaii's Big Island:

My father (second from left in back row) shipping off with his U.S. Army unit, all from Hawaii.

My father (second from left in back row) shipping off with his U.S. Army unit, all from Hawaii.

By his early adulthood, the Cold War was in full bloom. We joked for years that my father worked for the CIA. His stories were legendary. The rumors only grew after we requested his military records and received an apologetic letter from the Army: "Sorry, his records were lost in a fire." One of his uncles flew for the infamous Flying Tigers, American mercenary pilots that supported Chinese general Chiang Kai-Shek during World War II. This uncle, who almost certainly was with the CIA, later died when his plane crashed in a "crop dusting" accident in Central America.

Age 18, freshly enlisted

Age 18, freshly enlisted

Age 18, freshly enlisted

My father trained in the Texas desert. He showed early potential as a leader, reaching the rank of Captain in his early 20's. The Army wisely noticed that he had more value as a brain than a grunt. They trained him in radar and he helped build some of the earliest post-WWII radar systems. He later worked on missiles.

Posing with a radar installation.

Posing with a radar installation.

In the late 50's, his team submerged a nuclear warhead near the Elephant Butte dam in New Mexico. They trained Scuba-diving physicists to study the warhead's underwater decay. Later, he worked on a controversial attempt to detonate a warhead above the Gulf of Mexico to study its atmospheric effects. The project was scrapped after public outcry.

In 1962, the USSR and the U.S. faced off in the Cuban Missile Crisis, likely the closest we've ever come to nuclear war. My father's knowledge of missiles made him an asset. Like a scene straight from a movie, two G-men showed up at his house:

"Mr. Caceres, you must come with us."

"How long will I be gone?"

"We can't tell you that."

"Where am I going?"

"That's classified."

He bid goodbye to his family, rode to the airport, then climbed up the cargo ramp of a transport plane. He joined others who knew about nuclear systems at an "undisclosed location" while the crisis unfolded.

My father demos testing equipment for some high-ranking Army officials.

My father demos testing equipment for some high-ranking Army officials

My father demos testing equipment for some high-ranking Army officials.

Like so many engineers of his era, my father rose to Kennedy's challenge and went to work for the Apollo missions in the 1960's. His work focused on the Ignition Sequencer, a system that ran pre-launch system checks. In the famous countdown video, you can hear the announcer call "Ignition Sequence start". I envy that he lived during a time of such technological optimism in America.

As the Cold War matured, the U.S. government sought any edge over the Soviets. Nothing was off limits. My father became a test subject for Stanford Research Institute (SRI), where they pursued the wild and the weird. SRI and their partners in the CIA tried to train soldiers like my father in psychic powers (yes, really).

These gun-toting psychics would then peer beyond the Iron Curtain, to find useful intelligence like the location of nuclear sites. My father's recollections of these experiments were bizarre. He would receive a sheet of paper with a single name and location. He'd sit in silence and enter a meditative remote viewing "room". He'd then converse about the subject with his unconscious guide (which took the form of his daughter). There were a few strange coincidences. But nothing to suggest that Remote Viewing worked.

He joined Hewlett Packard in the early 70's. These were the days when Silicon Valley still focused on silicon. He prized the time he spent with "Bill and Dave", HP's eponymous founders. He was also proud of meeting programming legend Grace Hopper. He gave her an award from HP — an early computer chip encased in glass. Many decades later he lamented selling his 1970's HP stock far too soon.

My father then ventured to Washington D.C. and joined what we'd today call the Military Industrial Complex, where he worked through the 80's. He grew a reputation as a fearless executive. He was always willing to say uncomfortable truths. As the 90's arrived, I entered his world.

The truth is that I knew little of the man I've described above. By the time I showed up, he was nearly 51 years old. When I was born he went through a difficult time — too complicated to recount here — where he lost everything he'd built through no fault of his own. He became deeply depressed. I believe he never recovered from this difficult period. His shifting moods and occasional outburst of anger colored my childhood.

He was a hard man to know. He hated being the center of attention and rarely spoke of himself. My earliest memories of him are as the caretaker of a small trailer park in rural Maryland. It was not a luxurious life, but he was home. As with many little boys, he was my earliest hero: larger than life, the keeper of reality's secrets, and, yes, a little bit frightening.

As an adolescent, our relationship frayed. He had a temper. And so did I. We both seemed to have boundless energy to argue. I bristled at his old-fashioned ways. He bristled at the naïveté of youth. He was wholly practical, the sort of man that keeps a flashlight with extra batteries on his nightstand. And I, like so many 90's kids, focused on the budding world of the internet.

With some age, I came to realize that these arguments weren't about our differences. Our problem was that we were too similar. What else is more irritating than to see your own flaws mirrored in someone you love? In later life, my father mellowed and became a beloved member of the local community, respected equally for his kindness as for his reputation as a bullshit-seeking missile.

His greatest gift was introducing me to the world of men. However much we may wish it to change, the world of men remains cruel, competitive, and often dangerous. As I left home and came across the many challenges of the world of men, I appreciated him more. He told me what I needed to hear, not what I wanted. He was a difficult man. But he was always in my corner.

When he died, my mother and I held his hands. I had imagined the moment so many times before: what it would be like, all the profound thoughts I'd have when it finally came. But it wasn't like that at all. All I wanted was more time. And all I could think of, feeling his hands slowly grow colder, was the gratitude to have had any time with this wonderful, difficult, old engineer. I'll miss you, Dad.

Nov 01 2021
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