I think we have an ideology about talent that says that talent is a tangible, resilient, hardened, shiny thing. It will always rise to the top. To find and encourage talent, all you have to do as a society, is to make sure the right doors are open. Free campus visits, free tuition, letters to the kids with high scores… You raise your hand and say, “Over here!” And the talent will come running, but that’s not true… [i]t’s not resilient and shiny… [t]alent is really, really fragile.

– Malcolm Gladwell

TL;DR

Just as Carlos in Malcolm Gladwell’s podcast had Eric Eisner championing his cause, I was fortunate enough to have a fifth grade teacher who believed in me. She pushed open doors for me even after one was seemingly slammed shut when my parents and I failed to turn in a financial aid form on time. Not every promising, underprivileged kid is this lucky— we need to do a lot more than just offer them scholarships because they face innumerable and unexpected inequalities and obstacles, starting with the ones in their heads.

Carlos Doesn’t Remember

Last month, on my way to my friend’s new luxury apartment in San Francisco, I listened to an episode of Malcolm Gladwell’s Revisionist History podcast entitled “Carlos Doesn’t Remember”, recommended by my co-founder. Like him, I quickly found myself in tears — the protagonist’s story was Ricky’s story, it was my story, it was probably many of your stories. Carlos is a smart, hard-working high school sophomore from a bad part of LA. He was fortunate enough to meet Eric Eisner, a former entertainment lawyer who founded a program called YES to help kids like Carlos get a scholarship to an elite private school. It sounds like he’s got his ticket out, but it’s never that simple. You don’t just leave behind where you came from because you get a scholarship to a good school.



In the podcast, Gladwell revisits a moment in Carlos’ life when his private school teachers were concerned that he didn’t play with the other kids during recess. It wasn’t due to a lack of friends because he was usually very gregarious in the classroom. Nor was it due to him feeling self-conscious as the only Hispanic kid at the predominantly white school. Eric Eisner found out: he literally couldn’t play because his shoes were three sizes too big and he couldn’t afford another pair. Carlos had also been accepted to a prestigious boarding school, but didn’t enroll because he didn’t want to leave his sister alone in foster care. He doesn’t like to talk about these things— in fact, he claims he doesn’t remember any of these incidents.



Carlos’ story highlights a problem that I’ve experienced but was never able to articulate. While scholarships are supposed to be an equalizer — and we as a society should continue to make education more affordable and scholarships available — the real battle underprivileged kids face can be much more insidious and intangible. My co-founder Ricky touched on this battle in “Privilege and Inequality in Silicon Valley”:

Tangible inequalities — that which can be seen and measured, like money or access — get the majority of the attention, and deservedly so. But inequalities that live in your mind can keep the deck stacked against you long after you’ve made it out of the one-room apartment you shared with your dad. This is insidious, difficult-to-discuss, and takes a long essay to explain.

Ricky and I have had countless discussions on this topic, both before and after hundreds of people reached out to him, sharing their similar experiences. I’ve tried unsuccessfully to write about the subject multiple times. Carlos’ story reminded me of my own experience that I, too, have never felt comfortable talking about, and it also made me realize that we need to begin a public discourse on these unseen struggles. Someone has to start, so here goes.

Fifth grade and financial aid forms

I grew up in East Oakland as the youngest son of Teochew-Vietnamese immigrants. School was always easy for me—I never really felt challenged all throughout elementary school. Amidst the droves of teacher strikes and substitute teachers, the truly dedicated teachers of Oakland’s Maxwell Park Elementary School were few and far between. But in fifth grade, I was fortunate enough to be taught by Mrs. Harris, who changed the course of my life forever.

Right away, I knew that Mrs. Harris was special; she cared deeply about her students and went to great efforts for us. On weekends, she invited students to her house for lunch. Using her own money, she gave away trinkets to those who did well on assignments. And during one of the parent-teacher conferences, she did something unthinkable and so incredible that I didn’t fully comprehend its impact until years later. She begged my parents to have me apply to private middle schools to get me out of the failing Oakland public schools.

My parents, who don’t speak much English, did not understand what was happening. They didn’t know what a private school was, let alone why anyone would pay for school when there was free public education. Neither graduated from high school before fleeing from Vietnam to America with my eldest brother in tow. While they valued education for their children, they thought of education as uniform and binary — you either went to school or you didn’t. And as long as their kids went to school, that was good enough. If it had been up to my parents, nothing would have happened. But Mrs. Harris was hell-bent on making sure that I would have this opportunity for a better education, in spite of my parents’ lack of understanding. Everyday, she would ask me, “So have you started applying yet?” “Did your parents look into Head-Royce yet?” After weeks of hounding my parents and patiently extolling the importance of improving my education, Mrs. Harris, my brother, and most of my sixteen aunts and uncles managed to convince my parents to look into this private school idea.

Thanks to their efforts, I ended up applying to the prestigious Head-Royce School in Oakland, taking the admissions test, and getting accepted, but I didn’t attend. Instead, I ended up going to the local public middle school because my parents and I had failed to turn in the financial aid forms before the deadline. It took a village to push my parents to apply to Head-Royce, but there wasn’t anyone around to help us with something as mundane yet essential as filling out the financial aid forms on time. There probably were people who could have helped us, but my parents didn’t want to bother anyone by asking for help. That was their immigrant mindset: you shut up, work hard, and definitely don’t burden others.

I remember getting a voicemail from the head of admissions at Head-Royce, asking if I still wanted to enroll despite the lack of financial aid. Growing up, I never really thought that we were poor, or at least I didn’t understand what that meant. The words “federally-assisted lunch program” actually made me feel special since I got free lunches at school. But once I found out that the school’s tuition cost more than my parents made in a year, I suddenly realized that there was a world beyond what I had known. Before applying, I had no idea that Head-Royce or private schools even existed, but now that I had a window into that world, it felt like the window had been boarded over, shutting me out.

Here’s the crazy part — I internalized this whole process to mean that I wasn’t good enough for Head-Royce. I had taken a shot at the big leagues, trying to get into a better school, and I had been rejected. I wasn’t smart enough. I hadn’t worked hard enough. I wasn’t enough. At first, my parents complained about the unfair system. It felt like someone had opened up a door, then prompted slammed it shut, all because we had forgotten about some stupid fucking form. However, soon after, both my parents and I took the closed door to mean that I wasn’t good enough, that I hadn’t scored high enough on the tests, that Head-Royce didn’t want me after all. If I had and if they did, they would have given me a scholarship. I felt awful and ashamed. I didn’t tell Mrs. Harris what happened; she believed in me, and I let her down. I wasn’t good enough.

Second Chances

I might have given up on myself, but Mrs. Harris refused to give up on me. When she found out that I didn’t get into Head-Royce, she went to work on a back-up plan. Maybe she knew what really happened with the financial aid. Maybe she just believed in me that much. We tried to get into a better public middle school in the wealthy part of Oakland, but nothing came of our efforts. Undeterred, Mrs. Harris contacted and pushed to get me into the Heads Up summer program, which offered free classes at Head-Royce for underserved kids.

I remember sixth grade feeling like a lost year. I can’t remember any of the teachers’ names. I just have memories of the English teacher who the kids made cry and the substitute math teacher who yelled at me when I corrected him on how to do long division—never mind why a sixth grade classroom was being taught long division. But I had been given hope. During summer classes at Heads Up, I felt challenged academically for the first time ever and really started to love school. That newfound appreciation for education also rubbed off on my parents — they somehow saved up enough from their minimum wage jobs to pay for a math tutor whose house I went to twice a week that year. Mrs. Harris changed everything. I hope she’s reading this, since I don’t think I ever even said thank you. Thank you.

I applied again to Head-Royce, this time for seventh grade. We applied for financial aid as soon as it opened up and had several people check over the forms to make sure everything looked right. Thanks to the generosity of the Malone Family Foundation, I received a financial aid package that allowed me to attend Head-Royce. Head-Royce felt like paradise. Everyone there was smart and loved to learn. The coursework was actually challenging. I loved it. Even so, I never felt like I fit in. I never, ever told anyone about what had happened when I had previously applied to Head-Royce— it remained a huge, shameful, dirty secret. I don’t think I ever got over that feeling that I wasn’t good enough, though it certainly motivated to me to work my butt off. Years later at Stanford, where a large percentage of the student body receives some financial aid, I maintained that internalized feeling of not belonging in this world, of not being good enough. I never talked about it. Not at Head-Royce. Not at Stanford.

I never graduated from the Heads Up program. After enrolling at Head-Royce, I still spent my summers in Heads Up classes and attended the monthly meetings that continued through ninth grade, but I eventually stopped going. I remember Mr. McCoy and Mrs. Gee, who ran the program, being disappointed in me. As a high school freshman, I couldn’t quite explain to them why I dropped out of the program: I just didn’t want to be there anymore. Years later, I realized that it was because I was ashamed. Way back in fifth grade, Heads Up didn’t feel like an opportunity — it felt like a consolation prize for not actually getting to go to Head-Royce. I was very self-conscious going to Heads Up meetings after I enrolled at Head-Royce. I felt like an outsider when everyone talked about their schools, and I didn’t want to brag about how great actually going to Head-Royce was. I think part of me almost wanted to erase the fact that I was in Heads Up because I just wanted to fit in at Head-Royce. I remember making it a point to never mention to any of my classmates at Head-Royce that I was a “Heads Up kid” because I had once heard someone describe it as charity for poor public school kids.

Isn’t that crazy? Somehow, despite everything, I had been fortunate enough to be a part of the Heads Up program and then attend Head-Royce on a full scholarship from grades seven through twelve. But rather than talk about any of it, I tried to hide or forget everything— like Carlos, I tried my best to not remember any of these incidents. Out of shame, but also motivated by something else Gladwell points out: survival instinct. Once you see a way out, an opportunity for what he terms capitalization, the ability to reach our potential in a meritocratic society, you become laser-focused on that opportunity. It doesn’t matter whether it’s a scholastic or sports scholarship, or a less traditional path. Being poor, you cannot afford to fuck up the opportunity that comes along. You don’t take it for granted because you understand you’re playing by someone else’s rules. Even today, Ricky and I often feel like that. Given the long odds we beat to get here, sometimes in our heads, our world feels very fragile; at any moment, the clock could strike midnight. We’ve encouraged each other to talk more openly about these feelings, in an effort to strengthen and reinforce the reality of what we’ve built.

As Gladwell pointed out, capitalization is generally only possible when you have a champion who can not only show you the way, but help carry you there. Mrs. Harris was that hero for me. She wasn’t a big-shot lawyer in this case; she was just a teacher who believed in me. She made opportunities happen for me, and she persisted when things hit unexpected roadblocks. But not every kid is lucky enough to have a Mrs. Harris. Or an Eric Eisner. Remembering that and thinking about how many underprivileged kids must be experiencing this on a daily basis is why Carlos’ story brought me to tears.

We as a society need to do more to not only find these lost diamonds in the rough, but to dig them up, champion their cause, and push open doors for them, like Mrs. Harris did for me. We always need more Mrs. Harrises and Eric Eisners, but this isn’t just a call for champions. I believe that in order to level the playing field for underprivileged, minority or other disadvantaged groups, providing opportunities is not enough — we need to start talking openly about the differences in background, mindset, and opportunities that persist even after you attempt to level the field. When discussing diversity, people often bring up the idea of a pipeline, where the focus is on bringing in as many qualified, underrepresented or underprivileged candidates as possible. But perhaps we should start thinking about it as less of a pipeline and more of a leaky funnel.

The fact is, when you grow up poor or disadvantaged, there are innumerable places where you might drop off before you have a chance at capitalization, at a better life. As Gladwell points out, many of the brightest students in Carlos’ hometown end up gang-affiliated as early as the eighth grade, long before free SAT prep courses, scholarships, and admissions officers can open up doors for them. We have to do more to ensure that the underserved know what opportunities are available to them and help them through every step of realizing those opportunities.

In the face of adversity, you have far fewer chances, far less margin for error. I cannot speak on behalf of people of color or women in tech, but I would imagine they experience similar drop-offs in the funnel due to discrimination. The oversights and slights you internalize over the course of many, many years make the rare opportunities you find even rarer and leave you unable to capitalize on what’s left. If we want to start to spot and seal the cracks and leaks that leave people behind, we need to begin the dialogue on unseen inequalities and unexpected drop-offs.

To everyone who has experienced this— who has felt like they don’t belong or aren’t good enough— the world needs to hear your story. Only then, can it begin to give current and future underdogs a better chance at a better life. And just remember: you ARE good enough. You DO belong.

Thanks to Ricky Yean and Sarah Staatz for reading drafts of this.

Thanks to Mrs. Harris, Barbara Gee, Howard McCoy, Crystal Land, Peter Reinke, the Malone Family, my brother Peter, my parents, and countless other teachers and people who saw potential in me when I was too young to understand all that they were doing for me and without whom I wouldn’t be here today writing this post.

The Heads Up program that I was fortunate enough to be a part of has provided free challenging and enriching classes and programming to thousands of low-income middle school kids of color in Oakland since it was started in 1980. I will be making a contribution to the program— if you’d like to join me in doing so, please visit https://www.headroyce.org/page.cfm?p=1415. Thanks for reading!