My autobiography, family history and timeline of life events


Paternal Family History

In the early 1900s, the recently unified Kingdom of Italy was a nation where Catholicism was not just the only religion, but the centre of culture, knowledge and power. It mandated that the Catholic Church (or State) control the religious experience, and outlawed hearing the scripture in any language but Latin - which the common people couldn't understand. So it caused quite an uproar when my great grandfather was the first in town to convert his family to Protestantism.

His daughter, Bruna, a poor farm girl, was engaged to marry my grandfather, Emmanuel, whose family owned the olive farm she worked on, but at age 19, he went to Germany to fight for the Axis as a sergeant in WWII. But while stationed near Stuttgart, his superiors back home decided to betray Germany and join the Allies, so Emmanuel was promptly arrested. Imprisoned by the people he had fought to defend, he endured years of slave labour, degradation and near starvation during his "prime eating years" on potato skins and thoughts of his fiancรฉ, who was still waiting for him back home. At the end of the war he was released and hurried back to marry Bruna and move with her to Canada where my father Jim was born in 1957.

Maternal Family History

My great grandmother, Pia Cudrig, then an unmarried Austro-Hungarian house servant, gave birth to my grandmother Marina in Rome in the year 1944. Having never known her father, Marina grew up poor working as an au pair in the UK, where she met her future husband, Al, a General Manager for British Airways. They wed and had their only child, Lara, in London in 1962. At age eight, she moved to Canada where she would go on to study Economics at York University before getting a job at Scotiabank, where she met another York graduate from its prestigious Schulich School of Business, my father Jim. They wed in May 1984, and started saving to buy a house in Maple, Ontario where I would be born five years later.

Family & Childhood

The Importance of Family

Coming from a good family is an extremely important part of life, maybe the most important. It is literally everything you started as, in a world that was already divvied up long ago. It is so important, that the elite have always ignored people from the wrong place, and they are usually right to do so, like we ignore animals. Maybe that's why it took so long for me to admit that coming from good stock just wasn't in the cards for me, and the limitations of that.

Some would protest my characterization. They'd say I am so lucky, that I should be grateful for all I have. They are wrong. They are only seeing me now, what I've recently become. They can't make an informed estimate of the odds I've overcome, nor would they ever voluntarily imagine what they've spent a lifetime trying to avoid. That's fine, I need no pity, but if the truth is to be understand about me, I must be honest about my past.


In the good old days, battles were fought over who would inherit Europe, and who would have to go start from scratch in America. In this way, America can be seen as the land of the rejects, though it's come a long way since then. Canada on the other hand, was the fallback country for immigrants that couldn't get into the States - the rejects of rejects - which is where I was born. So was my father, so this bottom-of-the-barrel culture had 32 years to ferment and fester in his mind until I was born a decade before 9/11, so my life would be spent solitarily rebelling against what no one else could see (and later wouldn't admit) was a collapsing society.

I remember when playing ice hockey, our coaches told us it didn't matter who won the game, as long as we had fun. I didn't like that. I wanted to win. What a horrible thing to tell children. But that's Canada.

My Parents

My father had a cushy property manager job for a multi-billionaire, politically-connected Italian family that owned commercial real estate all around Toronto (and where I worked a few summers as a teenager). My mother was an executive sales manager at IBM, a once innovative mega-corporation whose stock was falling into a long decline due to general stagnation and what seemed to be a corporate culture in which everyone climbed the ladder by collectively making sure that no one would be called out on their bullshit.

I would describe them as very boring, suburban people, confused how they ended up with such an opposite son. In fairness, I will admit they were responsible and occasionally helpful. Yet despite being millionaires, they expected praise for providing basic necessities, while pretending not to understand how they were draining me. How many thousands of hours did I spend trying to explain, when they never really cared? They never did much with their lives, so could impart only false wisdom. They didn't know the first thing about love. They talked like it should be some practical, efficient thing. And if I tried to share anything going on in my life, they would project the most pathetic motivations onto it. So they never knew me, only their imaginations.

jack vaughn young toddler


But most of those family conflicts occured in my teens and later years, so in childhood I was generally a happy and adventurous boy. I liked riding my bike through the forest and exploring unchartered terrain, books about dragons and acting out big, character-rich stories with my younger brother, Mark.

Unfortunately, few of my early friendships lasted more than a couple years because one of us would always move to a different school or class, and I suspect these repeated fractures contributed to my rolling stone personality. My brief friendship with Amy was perhaps one of the more interesting.


Amy was a cute little blond girl that lived in the big red house beside mine. We only knew each other when we were very young, maybe 4 or 5. We would do things like roll down a hill or build a "house" together (really just a wall) out of the leftover bricks from my parents' new patio. But one day her family moved away. It wasn't until 20 years later, when I was watching the opening sequence of my film, Cherries and Clover, about friends who are separated in childhood, that I was stunned to discover I had subconsciously written, filmed and edited this sequence without realizing that I was the little boy, Clover, waving goodbye to his first friend.

High School

Conflicts with Dogma in Catholic High School

I didn't like the unquestioning, puritanical culture

Creative Rebellion

Rebelled with some light truancy, making mildly controversial art, and by reading Ayn Rand or Socrates


My very cute first relationship. Reminds me of the Arcade Fire song Sprawl II (Mountains Beyond Mountains)

Writing Cherries and Clover

A coming-of-age romantic comedy I wrote in high school and later filmed. See Film


Residence Life

I loved living on campus at York University

Film School Rejection

Denied admission, despite my GPA in the 95th percentile, because there were already too many white boys in film

Shooting Cherries and Clover

Took advice from my boss Dave King and made my film anyways. See Film

Dropping Out

One of the best choices of my life


Moving to California

My initial idea of "escaping privilege" in Los Angeles ended up landing me beachside in Santa Monica, CA


Got into lots of fun trouble with this crazy Boston playboy. See Mushroom Trip II

Amazing Santa Monica Apartment

I put up a wall and sublet the spare bedroom of this subsidized apartment for more than the total rent, giving me free time to invest in business


Very sexy, fun-loving actress. Married her in Vegas when she turned 18 and had a difficult, but formative, hot-and-cold relationship


Dozens of amazing roommates from all over the world, like tech star Jonathan Perichon, many actresses/models, and even a Rothschild

Parking Spot Saver

Taught myself electrical engineering and programming to develop this device and company. See Technology

Software Engineering

I had jobs and opportunities with many startups and icons like Roger Ver and billionaire Matthew Mellon though I prefered my own projects

Enterprise Sound

A music platform I cofounded with roommate Lucas Gerbeaux


My ex cheated on me so I divorced her right before becoming a millionaire


See Bitcoin


Moved to Nashville for 3 months to escape California taxes and get a taste of the South



Six incredible months in Moscow and Saint Petersburg

Lithuania, the Netherlands

Fell for this Lithuanian girl and spent two years living in Utrecht & Kaunas


Moved to Stockholm