This is a post about growing up.
My parents are an old school latin couple: My mom (b. 1938) grew up in a small town in Argentina. My dad (b. 1929) grew up bouncing from village to village in the deserts of southern New Mexico. They met at UCLA in the late 1950s and got married in 1963.
Yes, I am 29; and yes, I was a total accident. (I think that they thought the machinery had stopped working by 1980.)
Anywho, my parents are Catholic––my mom more so than my father––and like my 3 elder siblings, I spent my childhood and adolescence getting a Catholic education, first at St. Bruno’s Elementary School in Whittier, CA; then at Servite High School in Anaheim, CA. It should not surprise you that I was a major pain my teachers’ collective in the asses: I chafed at the concept of authority qua authority and constantly harassed my elders, unafraid to give them shit.
Obviously, little has changed.
Yet despite my protestations at the time and the fact that I had renounced my Catholicism in 7th grade, some of these lessons stuck. One in line in particular, the specifics of which are hazy to me, got burned into my brain: something about how a man’s character can be culled from how he treats “the least among us.”
The general principle here is that if you want to see who a man really is, give him power. Watch how he treats the people beneath him, the people with less power, less status: Does he treat them with respect? Does he act solely on the basis of self-interest, or is there a deeper magnanimity at play in his behavior?
As an entrepreneur, I think of this often.
Personally, on this matrix, I have failed often. But my heart is in the right place.
The thing is, I have a little chip on my shoulder.
My family always had more brains than money. My father was a community college professor who had clawed his way from a childhood of poverty into college, then grad school, then the American middle class. My mother, a kind and nurturing women who suffers from crippling emotional problems, spent her life as an artist, churchgoer and housewife.
In high school, we were in the bottom tier of income earners. It wasn’t that we were poor, it was that everyone else was rich, at least by comparison. For some perspective, Servite is a prep school in Orange County, California––Orange County as in “the OC.” But I was one of the guys, and although no, I didn’t have my own car and yes, I mowed my own lawn, I never felt different. Like the rest of my friends, I was a know-it-all honors student and a little punk.
After high school, I went to a popular destination for punk ass know-it-all honors students: UC Berkeley. Still a punk, I quickly grew unsatisfied and began to lust after real adventure. After a single semester, I dropped out and got a job working as an EMT on an ambulance in Southeast Los Angeles (Lynwood, Compton, Southgate, and Watts, if you want to be specific). There, I found adventure. And got my bell rung.
As it turns out, no one on the ambulance gave a shit that I had gone to Berkeley or had been a honors student. I was just a punk, a clueless punk. After 6 months, I got fired for disagreeing with my boss over how to treat a severely injured child. He wanted what was good for the company, I wanted what was good for the kid.
That next fall, I returned to Berkeley.
Fast forward two years and I had dropped out again, this time to fight forest fires in Montana and, later, the Sierra Nevadas. When the snow started to fall and the fire season ended, I found myself back on the ambulance in LA. The boss who had fired me was gone, terminated for embezzlement.
Not liking being low man on the totem pole––Paramedics run the show at the scene of emergencies, and EMTs are subordinate to them––I enrolled in a Paramedic training program. Still a know-it-all punk, I blew off the “required” preparatory studies and, along with 80% of my classmates, failed out of the program. And so I enrolled again, this time graduating at the top of the class.
The thing about being a Paramedic is that it really makes you grow up. When a baby stops breathing, when a car flips over on the freeway, when an asthmatic is on the verge of death, there is no one else to call. You are the cavalry. The EMTs, the fire fighters, the mother whose son just took two bullets in the chest and one in the eye: they all look to you for reassurance, for calm, for direction. Your shit must be together at all times. Or you must fake it.
To be honest, I loved the pressure. I loved being the guy with the cool head amidst a world of swirling chaos. Having been tasked as a child with taking care of my mother in her many panicked, distraught moments, it felt natural. I was born for this shit.
But I wasn’t born to follow rules. And that was the downside of being a paramedic: MDs created the rules––the protocols––and our job was simply to figure out which algorithm to use and apply it. I realized this fact in early 2004, about 2/3 of the way through my paramedic training. At that moment, I decided to go back to college.
UC Berkeley, I concluded, was not for me.
New York City seemed appealing, and through the grapevine I heard about a program at Columbia University for “non-traditional” undergrads who had skipped or dropped out of the traditional college path in favor of a life more interesting. That summer, while fighting forest fires for one last season, I applied and was accepted.
My dad, a frugal man if there ever was one, called it a dumb idea. “Son,” he said, “Look, I know you love the bright lights and pretty girls, but New York is the most expensive city in the world, and well…Son, let’s face it: Columbia is a rich kids school. You are not a rich kid.”
And with that, he rescinded my parents’ promise of modest but meaningful financial support. Columbia was an education I’d have to pay for myself. My dad figured it would only take a couple semesters for me to throw in the towel, get my head on straight, and head back to Berkeley.
He was almost right.
If it’s not clear already, I was always something of a cocky kid. Never in my life had I felt poor or “less than” anyone. I feared no one. All were my equal, and I believed that there was nothing I could not earn through merit and hustle. That is, until I arrived at Columbia.
The sneaky thing about this “non traditional” undergraduate program at Columbia is that––at least compared to the “traditional” college where scholarships abound––they fuck you on financial aid. The mean debt load of my graduating peers (the ones who needed financial aid, not the millionaire-in-my-twenties ex-hedge funders) was $80-100k…for a fucking undergraduate degree!!!!
Misguided academic administrators and financial aid officers did their best to obscure the numbers and peddle the debt as a worthy investment.
I saw through the bullshit and promised to graduate with no more than $35k in student loans. Skip, the financial aid officer, chuckled when I announced this in our first meeting. “Let’s be realistic,” he said.
Well, as it turns out, Skip, I graduated with only $25k in student loans, no thanks to you.
My first Paramedic job in New York paid $23/hour and offered one crucial perk: all-you-can-eat overtime. It was on an ambulance in the South Bronx. Once I had some experience, I got a second job on an ambulance in Washington Weights that paid $25/hour. I made my own schedule and regularly pulled 16 hour days. If needs be, I could clock 48 hours of work in 3 days. During one Spring Break, I clocked over 100 hours.
Even though the pay was great and the flexibility was ideal, I still struggled. Tuition was $1,100 per credit. Plus, living in Manhattan, as my father had predicted, was not cheap.
In July 2005, I hurt my ankle off the job and made the mistake of telling my employer. This put me out of work for 6 months. With nothing else to do, I took summer classes, which were more expensive than normal as Columbia––whose financial aide was meager to begin with––budgeted nothing for the summer session. I used an American Express Card to pay for tuition. The bill was $10,000.
During that time, I also began to pursue a longtime interest of mine: journalism. Covering the visit of foreign dignitary for the school paper, I met an injured Iraq Vet named Garth Stewart. He had gotten his leg blown off as an infantryman during the war and, having been medically retired by the Army, had enrolled in Columbia’s “non traditional” undergraduate program. I wrote a story about him.
It took me 6 months to pay off that $10k AMEX bill. I worked 50-70 hour weeks even as I was in school. At the end of the semester, I was exhausted. My grades were good, but my financial aide situation and unwillingness to take on massive debt meant that I could only take a handful of credits each semester. College 2.0 was progressing at a snail’s pace.
Frustratingly, this created a chicken and egg problem when it came to scholarships. The National Association of Hispanic Journalists (of which I was a member and later got a scholarship from), for example, reserved all their scholarship money for full-time students. I tried pleading with them (and others): “I can’t afford to go full-time unless I get a scholarship!” Their response was polite yet indifferent.
I had never before felt bounded by social class, by economics, by mother fucking money.
I remember when it hit home: I was taking a graduate seminar on Afghan Politics. After class one day, I struck up conversation with a girl sitting next to me. She asked about my background. “I used to fight forest fires,” I explained, thinking I was so cool.
Her forehead crinkled. She stopped for a second, then responded: “Oh. I didn’t know they let people like that, you know, in here.”
Crash and burn.
There were other things too. On Fridays, I would typically work late and hit the Columbia gym before heading back to my apartment. As I headed home, the college girls would be heading out. Sometimes I’d see a woman I knew from campus and try to strike up a conversation or make eye contact. But the blue paramedic uniform was a signifier of the wrong type. It labeled me: “working class.” And Ivy League girls didn’t go for working class guys.
For the first time in my life, I felt shame. I remember trying to approach an attractive and otherwise cheerful brunette that I knew from an American History class. She gave me a once over, then eyeballed her friends in disgust: “OMG, what is this creepy guy in the uniform doing.”
Maybe I should’ve just brushed it off, but I’m a proud man. It hurt.
Also, there was that whole East Coast Ivy League thing. See, that was never me.
By May 2006, I was on the verge of quitting. Without a scholarship, Columbia seemed like a hopeless slog. It was either leverage myself to the hilt, or graduate in seven years. Fuck that, I said.
My voice cracking, I called my dad to discuss accepting defeat. The financial barrier seemed too high. I couldn’t find the hack.
Two days later, I got a phone call: News Corp had seen my little article on Garth the war hero and liked it. And by “liked it,” I mean they decided to cut me a $10k check and give me a fancy award. After the ceremony, which featured me sharing a stage with Rupert Murdoch and Mayor Bloomberg, my dad changed his mind about this whole “Columbia is stupid” thing and decided to start kicking in some cash for tuition.
Suddenly, I was back in business.
The extra cash allowed me to attend school full-time and scale back my time on the ambulance. Instead of 50-70 hours a week, I was putting in 24-40. Still a lot, but manageable.
Life started to revolve around school, with work on the ambulance a secondary concern. I started to feel a sense of belonging at Columbia, and with it that sense of the-world-is-my-oyster entitlement that so infects the Ivy League.
In 2007, I fell in love with a girl. Her name was Isabelle. The daughter of a real estate magnate, she had been born and bred in Manhattan’s ritzy Upper East Side. Although her parents had money and lots of it, Isabelle was down to earth, diligent and uninterested in extravagance or luxury.
While I spent every free moment either studying or working on the ambulance, Isabelle spent her spare time interning for politicians and magazines and political research groups––which is to say, polishing her resume. Occasionally, I would do project work freelancing for Newsweek and then later the NY Times, but that was rare.
It wasn’t fair of me, but I became jealous of Isabelle. Being a paramedic, which had been fun and exciting at first, devolved into a mercenary task that I did for money.
Every day on the ambulance was another day of me not polishing my resume, of me not moving up in the world. It was a constant reminder, a symbol of how no matter what I did, the deck was always going to be stacked against me. The truth is that I wanted what Isabelle had: Freedom. Freedom to try different jobs, to check things out, to explore, to travel.
Over Christmas break one year, Isabelle flew to China––a country I had studied in class and desperately wanted to visit––as I, once again, worked 90 hours a week on the ambulance. Checking Facebook during those times were downright depressing. Everyone seemed to be posting pictures of their visits to Ireland or Istanbul or Tehran. Meanwhile I was on the bus with the idiot no one else wanted to work with, picking up drunks on the corner and covering for my partner’s incompetence.
By the time I graduated from Columbia in the spring of 2008, it was clear that the mainstream media as we had known it was doomed. Journalism was the one job I had trained for, and now, gutted by the internet, it served only a door into the abyss.
It’s hilarious to consider now, but during that period I actually wanted to be an investment banker. Not that I really understood what the job entailed (or that I even do now) but there was one thing I did understand: Being a banker, at least in New York in the summer of 2008––before the Lehman meltdown, before the AIG debacle, before the apocalypse––being a banker meant that you were someone who had money and who the pretty Manhattan girls would talk to on the train. All the smart Columbia kids were doing it, after all, including the women.
And so I asked about interviewing at Goldman. My lack of resume polish was, predictably, an obstacle.
That summer, I attended a 5 week business-for-idiots program at the Stanford Graduate School of Business. It was there that I discovered the world of startups. Visiting entrepreneurs lectured us, spinning tales of adventure, chaos, glory and, yes, riches. In this mythic world, normals and rule followers were torn to shreds. Success, they explained, required being a street-savvy swashbuckler who broke all rules.
I think they were trying to scare us off.
But for me, it was a hallelujah moment. Fuck banking. Fuck journalism. Fuck everything else. This is what I was born for, I thought.
For the first time in my professional life, someone described for me a job that didn’t require me to fake or hide or suppress who I was. It felt awesome.
In October 2008, during the chaos of the financial apocalypse, I decided to start the company that would become SpeakerText. “Starting” was a declarative act, but so began the long journey.
It is ongoing.
