Why I Became an Entrepreneur (the Long Story)

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.

34 Replies to “Why I Became an Entrepreneur (the Long Story)”

  1. Matt,
    I stumbled across this as I prepare for classes to start this semester. The knowledge you shared with me while I was doing my rotations at Mt. Sinai has stayed with me since. More than the “tricks of the trade” of being a paramedic, but your drive to succeed with Speakertext. Within a month and a half of completing paramedic school I was back in school working on finishing up my degree. I have three semesters left, and will be spending the summer studying and traveling abroad. While I do work as a paramedic upstate occasionally, school has become my focus because without it, I won’t be able to get where I plan! Grad school and beyond to the “real world”.
    Thank you for all your wisdom and best of luck with Speakertext!

    -Chris McKenna

  2. Great post. We have a few things in common:

    1. I’m middle class — not wealthy — with immigrant parents
    2. I constantly challenged authority and was bounced from catholic school in grade seven
    3. I went to Columbia, was class-conscious for the first time in my life when there, and ran out of money, then left.

    I was @ Columbia in the early ’80’s and started out as an English/Journalism major. While I was working weekend jobs, my classmates were going to Fassbinder film festivals and the like.

    Once I realized there were no jobs (my journalism prof, Louis Uchitelle, made sure we knew that) I dumped out of Columbia (which I could not afford anyway), switched to a “hard major” (one with jobs as well difficult to get A’s) Math/Computer Science, transferred to the University of Minnesota and graduated there. That eventually led to a successful startup, then a career at Microsoft (10+ years) and now entrepreneurship (again :)). I don’t regret any of it, and I wish you luck with SpeakerText as you strike out!

  3. I really admire your badass-ness, especially since I’ve spent far too much time with bankers. My story starts in mainland China and involves chicken-keeping before chickens were hip. I don’t quite understand, though…why were you paying so much to go to Columbia? That was enough cash to be your Series AA. My brother and I got crazy financial aid even though my family was hardly poor by the time we were college-age (my dad was also a college prof). Every year, I paid 8K plus 2K in loans to go to Rice, and my brother paid even less to go to Caltech. Then I went to law school for free. I landed my freebie through a merit scholarship, but several of my friends got freebies by being graduate assistants. In return for grading freshman papers, they got free tuition and free health care, and their living stipend was bigger then mine. Graduating debt-free is really fun.

    Fyi, it’s also possible to go to business school for free.

  4. Hey Matt,

    From one 29-year old scrappy founder to another, nicely done, dude. Great story all around, equal parts entertaining and insightful.

    One thing that has really been on my mind lately – and your story certainly echoes this – is the societal/cultural acceptance of what it means to pursue a startup. I come from a town of 80k working-class folk in Canada where there is literally ZERO notion of what startups are, let alone a culture that nurtures and fosters startups.

    For people like you and I that came from places outside North America’s major tech hubs, choosing to go down a path that few around you understand or relate to can be a very, very isolating experience. When literally nobody in your life truly “gets” why you’re doing a startup when you could be doing noble things like fighting forest fires or saving babies, it creates a major disconnect, one that I suspect results in the lion’s share of aspiring would-be entrepreneurs abandoning their plans for world domination.

    There was actually a good PG vid recently < http://bit.ly/cq1LaD – skip to 1:40 for relevant part> where he alludes to a demographic shift making it more socially acceptable to start a startup in locales where it hasn’t historically been the case. It’s nice to see it trending that way, but there’s a long way to go towards full acceptance.

    Environmental barriers to starting up seems to get overlooked, but maybe I’m the outlier and that’s why it doesn’t get talked about – who knows. In any case, I can relate to parts of your story very closely, so thanks for sharing – getting to the early stage where we are is half the battle in itself 😉

    Keep fighting the good fight, man.


  5. I believe most of us entrepreneurs can relate in some fashion.

    ANYONE – If you haven’t read ‘Outliers’ by Malcolm Gladwell, it will shed some scientific light on why certain people succeed and what is common across their backgrounds. It’s a great read!

  6. That is an awesome story. Reminds me of my co-founder, actually, who wanted to go to Stanford undergrad for CS but couldn’t cuz ‘o money and ended up at Iowa State.

    Where you based?

  7. Oh totally! Although on occasion this whole chip-on-my-shoulder is a mixed blessing and I end up shooting myself in the foot. But c’est la vie, i guess. Part of growing up is trying to amplify the angel and quell the demon in us all.

  8. Well, I already had the idea of building SpeakerText, but at the time I was trying––naively––to get a large media company to hire me to build it in house. It had never occurred to me to try and start a company around the idea until I did that gig at Stanford.

  9. I read your background before Matt, and although I’ve never fought fires or had a child go lifeless in my hands, I too came across startups at a later age then most.

    It is the chaos, and rule of raw nature that drew me to this path. Learning how to hack my way into a prototype was rough until I met my cofounder. Now I can dream stuff up and cobble it together in a couple of weeks of effort.

    After I read your tips for founders post I reacted by mentioning I would tatoo those hard earned lessons, generously shared, on the inside of my eye lids. Keep up the good fight with Speaker Evolution. Each startup isn’t just a product factory, it’s a legend in the making.

  10. Awesome story, Matt. You are a truly talented writer. And not bad as an entrepreneur. So when am I going to be able to stop by the SpeakerPad and see you guys?

  11. My background is very similar and very different. My parents were very young, rather than old. However, our family started out life poor and slowly worked its way up to middle class. As a kid, I not only mowed my own lawn, but those around me. I had a lot of typical kid jobs now done by adults: yard work, paper boy, shoveling snow, etc.

    We were poor enough that there was no money (other than what I could earn) for university tuition, yet by then, we weren’t poor enough to qualify for full financial aid. This meant I was restricted to State university, where a small academic scholarship, plus whatever I could earn during the summer and winter breaks, fell within reason. I worked as a janitor, cleaning railroad cars, stacking 100-pound sacks of flour on pallets, and as a laboratory technician; earning my way through college. When you are stooped down in a tunnel 4 feet high, shoveling wheat that spilled 2 months ago and has been rotting ever since, you really understand the importance in getting a degree.

    I too, worked 5 years on an ambulance. However, it was the university rig; all volunteer. People often wondered why, as a math major, I worked for University Health Services. I responded, “Because its not-math”. In reality, I had started out pre-med, but ended up a math major. I very much enjoyed being an EMT and Cardiac Tech. It was periods of boredom, interspersed with intense episodes of excitement. And I really liked helping people.

    While in university, I was surrounded by other kids there on their parent’s dime. I was honestly surprised at how little they cared that their folks were paying $10k – $20k so they could get drunk 4 days a week and bring 50 pounds of laundry home every month.

    One of my strategies for paying tuition was to join R.O.T.C. At that time, I still had visions of going to Med school. My disrespect for authority didn’t go over so well with the U.S. Army, so I abandoned that path before having to sign a commission. (But not after having spent too much time on my back saying “I’m a dying cockroach, Drill Sergeant!”

    After university, I worked 5 years in corporate software development before I was offered the opportunity to contract with a former co-worker. I have been a self-employed entrepreneur on-and-off ever since. Mostly on, although I’ll take a gig W-2 if the client really wants it and they understand I may be moonlighting on another project.

    I love working for myself. I can usually choose my assignments and my level of commitment. [Not always the case. In my line of work 2002-2003 was dead, and the last 2.5 years have been tough.] My office above my garage is great, with a wonderful view of the mountain and surrounding valleys.

  12. I loved reading your story. I actually grew up about 15 miles from you in Diamond Bar, CA (just up the 57 freeway from Whittier!). I also spent time working at a start-up based on the Harvard campus, and had the same sort of experience being an “Ivy League Outsider”. Thanks for your story, and best of luck with SpeakerText!

  13. Totally loved this. I get a feeling of what you mean with your experience as a middle-class kid, because you get to see the privileged lifestyle and your friends are all from it, but you can’t really afford it yourself unless you work hard for it.

    But hey, all your experiences has come in handy. Not many people starting their own business have the advantage of years of experience making life-and-death decisions under a lot of pressure, being linked to friends whose families are potential angel investors/customers and having an intimate understanding of how the media works as a business.

    All the best for your journey! This was an awesome way to start my day =)

  14. Matt, thanks for sharing your story. One question: were you first committed to the idea of becoming an entrepreneur, or to building Speakertext? It seems to me like it was the former, and Speakertext became the means to your becoming an entrepreneur.

    I was wondering what your thoughts were on the dynamics of these two paths (an individual committed to being an entrepreneur finding a problem to solve/issue to address, versus an individual committed to solving a particular problem becoming an entrepreneur). Do you think that people on one side of this divide do better than the other? Does one path offer easier/more difficult hills to climb?

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