Jumping Into the River

Matthew Mochary, Class 2

I like succeeding as much as the next person, and I define “success” as being one of the top performers in a given field. A long time ago I realized that there are two ways to be a top performer: play in a game where many people play and work better and longer than everyone else; or play in a game where few people play because it is so intense or unusual, and then simply survive.

For each choice, I have an image. With the first option, I see myself swimming in a lake. To get to the other side, I will have to stroke thousands of times, earning each bit of forward progress with significant effort. For the second option, I see myself jumping into a raging river. Forward motion starts instantly, but now I am not swimming—I am simply trying to keep my head above water while the raging current does the rest of the work. As each second passes, I find myself being swept along downstream. My task becomes simple: All I have to do is survive!

With these visuals, the choice for me becomes clear. Between performing really, really well, or simply surviving, it seems to me that surviving is much easier. Necessity is a very good motivator for me, so throughout my life I have looked for particularly intense experiences where few others tread. Then, by merely surviving, I am carried swiftly down the raging river of achievement. Robert Frost gave the strategy a romantic title, but I prefer to think of his “road less traveled by” more pragmatically as “the lazy man’s path to success.”

Identifying a Philosophy of Life

I have enjoyed some success in several drastically different arenas from my starting point as a member of the second class of Kauffman Fellows, working at Spectrum Equity Investors under Brion Applegate in 1996. In the 15 years since then, my career has veered dramatically. I founded a tech company (Totality) that was eventually sold to Verizon. I made a documentary film about Brazil (Favela Rising), which ended up winning the Tribeca Film Festival and getting short-listed for an Academy Award. I have worked with ex-convicts, teaching them how to get and keep a legitimate job (Mochary Foundation). And now I’ve jumped back into the for-profit world, starting a data center development business (DCMA).

The Society of Kauffman Fellows asked me to explain what philosophy of life led me down these vastly different paths. Well, I could make up a good story and say there was a philosophy, but the truth is that I stumbled my way through my career choices from one wacky idea to the next. I’m impulsive. If there is a philosophy at all, it’s that I allow myself to follow those impulses—I’m not afraid to jump into a river and see where it takes me. To my surprise, as one river led to the next, I found my passion and life’s work in the most unexpected and rewarding place.

Dancing to a Different Beat

Coming out of business school, I had no idea what I wanted to do. Luckily, everyone else seemed to know: They all wanted to get into venture capital. But entry was elusive, as the industry seemed to hire almost no one from the business school ranks. Perfect for me! I threw my hat in the ring with abandon, and simply barreled my way into the Kauffman Fellowship. (Back in those early classes, one could get away with that strategy; nowadays the applicant pool is so well-qualified that one actually has to have proven technological and investment ability.)

Once at Spectrum, I worked under Brion Applegate in Menlo Park. The firm has two offices, one on each coast. Another associate advised me that to advance I would have to get to know the partners in the East Coast office as well, so that they would approve of my eventual promotion. It all seemed too complicated to me—my goal was to merely survive. So, instead of working on projects with partners on the other side of the country, I simply showed up at Brion’s office each morning and asked what task I could do for him that day. It was an excuse to spend time near him, and watch what he did. The tasks started small—yes, literally getting him a cup of coffee—but each day allowed him to gain more comfort with me, and the tasks grew and grew until I was eventually his go-to guy. Two years later when Brion assessed his team, even though I had come in as the least experienced associate, I was one of the few elevated to partner.

By 1999, the internet bubble was soaring. It was clear that I was witnessing a unique moment in history that would not likely be repeated in my lifetime. My investments were making fistfuls of profit for my senior partners, but very little for myself (the promotion to partner was primarily in name, not economics). If I wanted to financially benefit from this moment, I’d have to get direct economics. The entrepreneurs I was backing often were not the most polished people, but rather those who simply had little else to lose by starting a company. If they were getting funded and hitting the ball over the fence, I imagined I might be able to as well. So, I headed for the raging river once again—I saw a hole in the startup landscape, and I knew it was where I needed to jump.

Starting Up

Systems integration shops like Scient and Viant were building e-commerce applications and the computers these applications ran on sat at hosting providers like Exodus, but no one was maintaining those applications once they were deployed. In-house IT teams were struggling to do it themselves, and often failing with disastrous economic consequences. I looked around for the executive who could build an entity to fill that gap, and found him in Michael Carrier, the CTO of Fort Point, one of the more-respected systems integrators. He agreed to start the company and accept my investment, but on one condition: I had to quit Spectrum and join him full-time. He reasoned that if it was my only lifeline, I’d be much more likely to insure that all the money needed to fund the venture would be raised. The raging river called, I jumped, and the bet paid off for Michael and me. I raised over $125 million for him, and he built a company that was later sold to Verizon and now forms the core of Verizon Business.

Taking a Break

Now, I had time and some financial flexibility. The pressure to perform was off. For the next few years, the wild waters were not figurative—they were literal. I surfed, for about two years straight, on every imaginable wave around the world. Not competing, just fumbling my way through. I might well have continued to do it forever, as every day was a pleasure, but I found that I was losing common ground with my best friends. They were still engaged in careers that involved daily challenges, while mine did not. We had less and less to talk about. I needed a challenge, and I started to look for the river once again.

Following the Hollywood Dream

I had no idea what I wanted to do, but again, the dreams of others provided me with an idea. It seemed that many people fantasize about making movies. I had never had that dream, but making a movie did indeed seem hard and I was looking for a challenge. So, I enrolled in a 5-week crash filmmaking course, and to my great surprise discovered that I really enjoyed it.

The next step was to actually make a movie, and since I didn’t want to waste time fundraising, I decided to make it with my own money. Documentaries are cheaper to make than narrative films, since no actors need be hired, so that’s what I chose. But on what subject? Well, I was curious about Brazil, since I’d never been there. I reasoned that if I was curious about it, others might be as well. So I went, camera in hand.

When I arrived in Rio, the opportunity appeared before me. The poorest and most violent slums sit on the hillsides in plain view of the wealthiest beachfront residential areas. I would show the inner world of the slum to the outside world that could see it but had never been inside. Of course, five weeks of training was not enough to make the kind of quality film this subject deserved, so I called up the best filmmaker I knew, Jeff Zimbalist, my teacher at the film school. After I described the story and offered to pay for his plane ticket as well as give him room and board in my apartment, he quit his job and came down to Brazil.

Together, Jeff and I jumped into the river. Two years later, the film was accepted into the Tribeca Film Festival, and—to our shock—it won. It later won Best Film of the Year from the International Documentary Association, was shortlisted for an Oscar, won 33 other film festivals, and was picked up for distribution by HBO and theatrical distributor ThinkFilm.

But the most important award from that journey was that while in Brazil, I met my wife Tatiana. Together we worked on the film and discovered that filmmaking can indeed be a lot of fun. We were able to live in a world that we would never have been allowed to enter otherwise. We crafted a story from raw footage. And when the film was being shown in theaters, we spoke to large audiences who hung on our every word. The whole process was intoxicating, so we came back to the United States and made a second film. This one was on the best heavyweight amateur boxers in the world, the majority of whom happen to live in one of the worst slums in New York—the South Bronx.

Making Connections

The film, called The Gloves, didn’t do as well critically as Favela Rising, but the experience for me was even more impactful. When we had lived in the slums in Rio, we realized that there were no schools, so the slum kids learned no skills with which to get jobs. They still needed food to eat, so they joined the only group that paid—the drug gang. The irony was that the drug gang didn’t pay well at all; since most of the slum kids wanted to join the gang, the pay didn’t need to be high to attract more than enough participants.

At the time, I thanked God that I came from a country where there is universal public education. In the United States, if a slum kid joined the gang, it was because he was too lazy to work at McDonald’s. He was making a choice—or so I thought.

When we made the boxing film, we found ourselves in New York’s worst slum and we suddenly realized that while our slums* do have schools, they are so bad that they might as well not even exist. The dynamic was the same as in Brazil—these slum kids couldn’t get a job at McDonald’s, or anywhere else for that matter. They dressed like thugs,* they talked like thugs,* they acted like thugs*—it was the only thing they’d ever seen.

(*I know these words read as inflammatory in politically correct society. But having spent so much time in the Brazilian and U.S. ghetto, and then interacted with mainstream middle-class hiring managers, I have learned that these are the words used in the ghetto and this is the perspective hiring managers have.)

Young people growing up under those circumstances weren’t hirable, but they still had to eat. Welfare only goes to mothers with children. For slum girls, the path is clear: have babies. For slum boys, the path is also clear: join the only group that pays, the drug gang. And, as in Brazil, it doesn’t pay very well.

Jumping Off the Deep End

Chilling questions occurred to me: Is it possible that the most hardened criminals in our country do what they do out of necessity, not choice? Is it possible that if they knew how to get and keep a legitimate job, they would, rather than resort to violent crime? It seemed like it would be a very unpleasant task to find out the answer. Whoever did would have to work side-by-side with known killers. Should that person be me? I didn’t relish the idea. By this time, my wife and I were married and beginning to have children—it was one thing to put myself in harm’s way when I was single, but now I had a family that I was responsible for.

And yet, if I didn’t find the answer to this question, then who would? Before I was 38, I had never spent time in a U.S. slum and I didn’t know anyone from my professional circles who had. I was in a unique situation. I had time and resources, but most importantly, I had witnessed the situation firsthand.

It was as if I had come across a burning car on a remote road. Would I reach out to the victims trapped inside, putting myself at risk, or would I simply move on? This time I hadn’t sought out the river—it had simply appeared before me. With much trepidation and anxiety, I jumped in.

My plan was to find the “worst of the worst” and see if I could “rehabilitate” him. I was told by staff at the Friends of Island Academy (the counseling center for youth released from Riker’s Island Jail) that convicts who are jailed during childhood are least likely to reform and have an extraordinarily high recidivism rate; they are often from the inner city, black or Hispanic, and members of a gang. Most of society views such convicts as unable to be rehabilitated—and when I met Kendrick, so did I.

Kendrick is 6’4″, black, a gang member since he was 13, in jail since he was 14, and a known killer. He looked like a thug, talked like a thug, and acted like a thug—he typified every stereotype I had of the inner city black man, and to my eyes at the time, he exuded violence.

I first met him when I went to Riker’s Island, the primary jail in New York, seeking a convict who was about to be released and who fit my “hard-core” profile. When Kendrick was released from prison, he moved into a homeless shelter. He had no cell phone, no money, and no food, and I had no good way of communicating with him. I realized that if I were to meet him at Riker’s, I would not only have to commute, but if he were late I would also never know if he would arrive in five minutes, five hours, or never. I hate wasting time—the only way this would work is if he came to my office. That way if he were late or didn’t show up, I could still be working. The catch was that my office was right next door to my home, with my wife and family in it, but there seemed little other choice. I was scared. Would he steal from me? Would he harm my family? My upbringing told me an urban black criminal was dangerous and I should stay away, but this was a river that I knew I had to jump into. If I didn’t, who would?

I invited him to come to my office, and by the end of the first day, all my fear had passed. There was much valuable equipment in the office, and yet at the end of the day not a pen had gone missing. It suddenly dawned on me that Kendrick could steal from anybody. Why would he do so from someone who had reached out to help him in such a personal, committed way?

Bridging the Gap

In order to help Kendrick, I had to ask myself why I wouldn’t hire him. The answers were clear: He dressed like a thug, he talked like a thug, he acted like a thug, and he didn’t show up on time. So, I set about correcting those traits. If I could transform him into a kid who seemed as if he grew up in the suburbs and had gone to a good college, then I hoped that Kendrick would be able to get a job. Knowing what stereotypes he evoked in myself and why, I hoped that with these changes he would be seen as trustworthy and hirable by other white, middle-class business owners or managers.

I set about working on that transformation. First, he needed to dress the part. We went to the Goodwill store, and for about $20, I bought him shoes, black socks, khaki pants, a belt, and several polo shirts. The change was impactful.

Then, he needed to talk the part. This would be hard, I thought—how could I ask him to change how he spoke? With no good way, I simply asked if he wanted to learn to talk like I did. Without hesitation, he said yes, and we set off on the task. To my great surprise, it wasn’t hard at all. I had noticed about six or seven common phrases that are grammatically nonstandard and constitute “street” talk. Things like:

  • Can I aks you a question?
  • I be doing this.
  • I done did that.

Each time Kendrick said one of these phrases, I simply wrote it down, then wrote down how I would say it, and Kendrick practiced the new way. Within three days, he was indeed talking like I do. The effect on me was bone-chilling—suddenly, he seemed like a suburban kid who had gone to a top college. The stereotype of the “dangerous black man” was no longer triggered, and that change had been effected with an ease that violated everything I had ever been told about “hardened criminals.”

I asked him why he was willing to do everything I suggested, and he answered: “It worked for you. Maybe it’ll work for me.” It was then that I realized his goal was the same as mine—he just wanted to succeed in life. But unlike me, he never had an in-person example of success to learn from. I was his first, and he wasn’t going to squander the opportunity. The example that Brion Applegate at Spectrum had given to me, I had finally been able to pass on to another.

Empowered, I decided to take his education to the next level and teach him how to behave politely, as I had been taught from childhood: To say “excuse me,” “please,” and “thank you” whenever he made a request or asked a question; to hold doors for people; to move out of people’s way on the sidewalk. We went to the local deli so that he could practice his new techniques while asking for a sandwich. He said to the worker behind the counter, “Excuse me, sir, can you please make a roast beef sandwich?” The worker smiled at him, and said “Sure.” As soon as we got our sandwiches, Kendrick told me that it was the first time anyone in Manhattan had ever smiled at him.

Kendrick loved the new techniques. He could see how powerful they were. Like anyone, he wanted people to like him, and now he had tools to make that happen in expanded social settings. Doors were opening for him, not just financially but also in terms of making connections with others.

But I suddenly felt fear—had I created an Uncle Tom who would be physically attacked, even killed, back in his own neighborhood? Was I putting a man’s life at risk just to give myself a “feel good” project? I asked Kendrick how people in his community reacted to his new way of dressing, talking, and acting. Was he in danger?

He laughed and told me that things had never been so good for him. When he walked through the neighborhood, guys came up to him and asked him how they could get a job too—they assumed by the way he looked that he had a paying job. And the women, well, they all wanted to be with him; they simply saw success written on him.

I breathed a sigh of relief, but also of sadness. Not only did Kendrick want to succeed, but clearly others in his neighborhood did as well. I was the example for him, and he had become the example for them, but how could I reach them all? I didn’t dwell on this daunting question then, though, as I was pulled back to the task at hand.

Next, Kendrick and I worked on showing up on time, and it was really quite easy. He had been trying to remember each appointment in his head—I simply bought him a $2 calendar that fit in his back pocket and asked him to carry it with him everywhere, write down every appointment he made, and always show up half-an-hour early. He did exactly that, and never showed up late again.

After two weeks, I realized that Kendrick was transformed and I would indeed be willing to hire him. So, I told him that it was time for him to try to get a job. (This was still back when the economy was robust.) He answered several want ads, got an interview, and was hired immediately. He became the overnight stock person at a big retail store. On that day, Kendrick said to me: “Thank you for believing in me, Matt. No one else ever did. Not even me.”

Finding My Dream Job

That was three years ago. Today, Kendrick is married with two children. He lives in an apartment in Brooklyn, just a few blocks from the grocery store where he works, and has been employed ever since our time together. Kendrick recently reflected, “When I first heard that I was hired [at my first job], I felt accomplished and motivated. I knew from that day on I would be able to get any job that I put my mind to get.”1

After Kendrick started working, I saw him less and less. We continued to talk on the phone, but I soon missed him. So I took on another ex-convict, Joshua. After a week, he too got a job and has been employed ever since. Then I started working with Dennis—after three days, he was ready.

Since then I have worked with dozens of guys, and the solution is always the same. The results have been consistently good—not one of my guys has gone back to prison. The current economy has been brutal for them, and most have had a hard time advancing from minimum wage jobs. But they are all employed. They are all making it. I continue to stay in close contact with the original three: Kendrick, Joshua, and Dennis.

Dennis recently told me,

You do realize, Matt, that I don’t know anyone else out there like you. 99% of the rest of the population wouldn’t even give me a chance, but you reached out to me. You’re like an angel from Heaven.2

Joshua shared with me how important our continued contact is:

Matt, you know that my life is hard. But when I get frustrated with my job, or my mom, or my girlfriend, I just call you. And you listen to me. You help me figure out the right answer. That makes me feel like I’m not alone. I usually already knew what the right thing to do was, but after talking to you I actually have the willpower to do it.3

Working with these ex-convicts has been the easiest, most high impact, and most fun thing I have ever done. I have never had better students in my life. They absorb my every word, and follow each suggestion without hesitation. Each of them is now like a son to me. They each view me as their savior, and have treated me and my entire family with nothing but the greatest respect. Joshua came to live with us for a time, and held my first-born child in his arms. We never felt unsafe; on the contrary, we felt as though he were a bodyguard.

I started out looking for career choices where few other people played, and ended up finding one where no one else plays. Having little competition is good, but having no competition is better—it is, in fact, the laziest man’s path to success!

Stepping Up to the Next Level

My wife and I continue to grow our family. We now have two boys, Luc (2 years old) and Zac (newborn), with hopefully many more children to follow in the years ahead. We have just moved back to northern California.

From a career perspective, the next step in my work with ex-convicts was to create large numbers of skilled labor jobs for them to work in. The current economic slowdown has virtually eliminated new construction in this country, which was the traditional skilled labor route available to felons. In order to create jobs for them, I had two choices: I could create a large-scale construction project using outside capital (wholesale data centers seem to be the only sector where new construction continues), or I could use my own capital to buy or start a small service business and grow it. I chose the former. An old colleague of mine, John Sheputis, is a successful data center developer who was open to the idea of directing future data center construction jobs toward felons; we have partnered, and our first project will be in Oregon, set to break ground in 2Q11. Our plan is to bring in as many felons onto each project as possible.

I wonder where we would be as a nation in 10 to 20 years, if each of us who knows how to get a job mentored one or two people who don’t? By putting our “underclass” back in the workforce, we would reduce the need for government spending on social services, reduce crime, and increase the size of the productive labor force. This is what we all hope for when we cast our votes at the ballot box—it turns out there is a way to effect that change ourselves.

I don’t know where this river will take us, exactly, but I do know that there is only one way to find out.

Matthew MocharyMatthew Mochary

Matt runs the Mochary Foundation, which teaches hard-core, convicted criminals the basic skills needed to get and keep a legitimate job. Matt has also produced and directed several feature-length films, including Favela Rising, winner of 36 international film festival awards. He continues to invest actively through his family office, the Mochary Group. Prior to these efforts, Matt was a founder and Chairman of Totality, an outsourced provider of internet application maintenance services. Totality was sold to MCI/Verizon and is now known as Verizon Business. Matt was a Partner at Spectrum Equity Investors and has been a director at OnSite Access, InternetConnect, Apex Site Management, and Nassau Broadcast Holdings. Earlier, he worked as a consultant with Bain & Co. He holds a BA from Yale and an MBA from Northwestern Kellogg.


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1 Personal communication, 30 May 2011.

2 Personal communication, 24 May 2011.

3 Personal communication, 24 May 2011.

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KFR Volume 2 Cover