boots on the ground
Building wealth as a first-gen kid in America's money-making tech machine.
Author’s Note: Jimmy’s a firecracker. The first thing he said to me when we began this interview was “Don’t hold back. Ask me anything you want.” And he was serious. In exploring his story, I was fascinated by the never-ending hamster wheel of operating in the money-making machine (being in corporate in America). The stakes of the grind culture seem to intensify for those who are the first to reach higher income levels in their family. Jimmy is the child of immigrant parents, which comes with its own set of pressures. Boots on the Ground is the “dark comedy” version of this experience that so many in the tech world know too well, based on what most of us take for granted.
[Names changed for privacy]
Jimmy decided in third grade that he would architect his life decisions around ensuring the well-being of his parents.
In the eighties, his parents immigrated to California, a few years before he was born. They had some family in the area, though he shares that what primarily pushed them to pivot their lives was a sentiment similar to many people in the world at the time: “To my parents, America was this big shiny place that was going to be exponentially better than where they were.”
“And they weren’t wrong,” Jimmy tells me. He’s on the other side of a Zoom call in a muscle T-shirt, drinking some protein shake. He just finished a contractor shift in residential home services, one of the jobs he’s picked up since taking a temporary break from corporate.
Jimmy has a tough exterior, and he is to the point with his words. He tends to speak in matter-of-fact tones. He’s the kind of person that if you go to him and tell him about something difficult in your life that’s been going on, he’ll immediately reframe it. If you tell him you got an amazing job offer just to have it rescinded at the final hour, he won’t say, “I’m sorry, that must be really hard,” or open a door for hypotheticals like “What do you think happened?” He’ll say, “Congratulations. Now you don’t have to work for that company.”
He’s loyal as hell, more than most, and the only times he doesn’t pick up a phone call or respond to a text from a friend is if he’s on a plane or sleeping. Those who know Jimmy know that he is really a big teddy bear, despite the unassuming evidence of his forced outward toughness. It’s all quite simple: He loves his friends, family, and country music. And as far as millennials go, he doesn’t try to overcomplicate whatever is happening in life that could otherwise be overcomplicated.
“Growing up in Korea is tough,” Jimmy says, in the same factual tone. Coming to America wasn’t a guarantee of striking gold, but it was worth the shot, and Jimmy’s parents didn’t have much to lose.
Jimmy describes the difficulty of making it in the corporate world in Korea, where your success is first determined when you turn six. “If you’re not performing in elementary school, you aren’t getting into a top high school. If you don’t get into a top high school, you’re definitely not getting into a top university, and without that degree from a target school, you’re cooked. You’re not making it in corporate. And there aren’t that many corporate jobs compared to the total population. Then, you’re just with the majority of the population, somehow making it work,” he says. There aren’t as many side doors, second chances, or meritocratic or quasi-meritocratic opportunities that are emblematic of the American dream.
In the United States, his dad didn’t speak English well, so he picked up odd jobs that usually involved manual labor. His mother went to school for a few years and flip-flopped between service jobs, including waitressing. During the dot-com boom and bust period, his mother identified an intriguing opportunity. Startups were popping up as quickly as they were shutting down. When a company shut down, there was a commonality: loads of hardware assets. She’d find the companies that were shutting their doors, buy up their hardware at a discount, then resell it to companies that were still in business.
His parents continued to flip-flop between different jobs and different rentals before saving enough money to purchase a house a couple of years after the financial crisis. Jimmy describes the community they lived in as lower middle-class by California standards, though his family tended to live a different lifestyle than those around him.
“I started to think we were dirt-poor. We just never spent money like everyone else. It was one pair of shoes. Nothing more than the necessities. No vacations, except maybe a local camping trip once a year,” Jimmy says.
He tells me he never understood the concept of cruises (what they were and why people went on them). “God, that sounds spoiled. I don’t think we were actually poor. I think my parents just stockpiled money. Then, I tried to do the same thing.”
Without much of anything, one learns to look for money in unconventional ways.
Jimmy began university and majored in kinesiology before switching to finance by the end of his first year. He didn’t want to pay for more years of schooling (becoming a physical therapist at the time required an additional two years), and finance seemed to have more upside. While Jimmy received grants and scholarships his freshman year, beginning his sophomore year, the money would no longer be guaranteed.
Continuing to live with the mentality that his parents would be taken care of and that he would not be a financial burden, Jimmy sought out ways to put some cash in his pockets to help pay tuition.
“There were these guys walking around campus with flyers for some door-to-door gig. I hopped on that,” Jimmy said. I ask him if it was a multi-level marketing scheme. He says it depends on who you ask. Regardless, the company wasn’t as well known at the time, and he saw an opportunity to try and make some cash selling a service he felt he understood from watching his father perform similar blue-collar work growing up.
“Maybe they were targeting poor students who needed money. But I was a poor student who needed money,” he says. “I ended up doing well because I understood the problem, I believed in it, and I could interact well with the people who opened the door because I learned the industry through my dad. But I ended up doing really well because I understood that time was the input in my control. I was a motor that never broke.”
Ironically, even though Jimmy switched his major because he didn’t want to be in school for six years, he was in school for six years. During his junior year, his GPA tanked, and he got kicked out. He left school, then went to community college before transferring back in.
“I didn’t want to read The Odyssey. I wanted to make money,” he says. He describes the feeling of seeing real money for the first time, at least for his age, and how his mind revolved around it, latching onto it as a survival mechanism. Then, in his pursuit, he started to devalue education as nothing more than a box he grudgingly had to check off instead of a skill set he needed to fill his pockets. “If I’m being honest, though, I wasn’t really good at school. It didn’t come easily to me in college like it did before. I think I failed financial accounting.”
Jimmy navigated the rest of college, trying to make sense of where his place would be. “At one point, I told my parents I wanted to join the Army, and they told me I was stupid to want to enlist if it wasn’t even required in America.” (Every South Korean male is required to complete military service when they turn eighteen years old.)
I ask if he would change anything about college, which is a stupid question, though one that still leads to intriguing answers.
“I have no regrets. You just can’t when you learned as much as I did,” he says, reflecting on his rocky path through school. Bartending, one of his many side gigs, was a lesson in “dealing with the masses.” It was a test of learning that one cannot control the inevitable—drunk people rioting, bar fights, working through fatigue at one in the morning, general human idiocy. Door-to-door sales was a lesson in being an “absolute savage,” but also in understanding the grind of a sales role. That in a well-performing sales machine, one can boil down the money they can make through predictable inputs, the most predictable being time.
“So, at the end, I really got two degrees. I got a useless one in finance that no one wanted to hire me for because my grades were shit, and I got a degree in Hustler’s Academy.”
The early sales team at the startup was a bit of a mixed bag. Or, one could say it was a pile of misfits. The hiring process had no structure, and Jimmy tried not to question how he was invited to the table. It was mostly young people, fresh out of college, who didn’t seem to have anywhere else to go but definitely had something to prove. And the company was doing well, with real repeatable revenue and dedicated customers. Somehow, it all just worked.
“We were just a group of people, sitting around a table, who were hungry and motivated and believed in what we were doing. There definitely wasn’t a motor issue. We were all there to grind and make money,” Jimmy says.
Jimmy wanted to be better than everyone else, for personal reasons first, followed by a touch of ego. He tells me he doesn’t really know why anyone wouldn’t want to be the best. Then he throws out a couple of sports analogies that I don’t fully understand, because I never watch sports except for gymnastics in the Olympics and the occasional Wimbledon match.
“So, were you the best?” I ask, even though I already know he was.
“It took me about three months to get it,” he says, then pauses. Or maybe he is only pretending to pause. “But after that, for sure, I was better than everyone else.” He chuckles.
Part of what makes Jimmy the best is he knows the outcomes and he knows how to keep his head down. He doesn’t stop to question the mathematical equation he’s already concocted in his head. He trusts that it works and avoids the existential mental rabbit holes that other sales reps frequently fall victim to. It’s an emotionless state of mind.
“Maybe it’s tough sometimes, but whatever. I have people [my parents] to support. I have a vision. I have a dream. I’m going to do anything to fulfill that dream,” he says. “You can give me a shovel and tell me to go dig in a pile of shit, but if you pay me well, I’m going to be the best shit digger in the whole universe.”
The tables turn for people who prove themselves tirelessly, sometimes in more ways than one.
The thing about sales is that it’s like a video game. You can always keep playing. You can turn your controllers as hard and as often as you’d like, staring at the screen, and forget the universe outside of you exists. Sometimes it’s tempting to press pause. But in real life, it’s expensive to take breaks.
Jimmy knows that if he sends 100 emails, 40 percent of the recipients will open the email, and 20 percent of them will respond, and another 20 percent will close. He knows the amount of time it takes to send emails in hours and he knows how his efforts convert and he knows the exact dollar value of this conversion. “So yeah, I never took vacation. The opportunity cost was too high. Why would I spend two [thousand] when I can make another ten [thousand]?” he says.
As the team grew and more reps and sales leaders were hired, plucked in a cookie-cutter fashion from other technology companies, the management team ran out of titles for the rep who didn’t want to train other people all day. Jimmy preferred to keep his head down and to close deals—to be a doer, not a teller. To be in charge of his money, with uncapped commission. He had a war chest to build.
“Give me a gun, point me in the right direction, and I’ll handle it,” Jimmy says. “The easiest way for me to feel fulfilled at work is being able to focus on my goals and being given the freedom to meet them.” He lambasts the internal tool fatigue (particular the vendors that promised cleaner CRM data to no avail), the post-fundraise motivation lethargy, the furthering from the original sales pen draft team.
If he were being honest, Jimmy also loathed being surrounded by people who didn’t understand the value of a dollar. He was a country boy, with immigrant parents, who made his first bucks upselling cookies from a Korean market in Los Angeles on the playground. I’m from the other side of the river, and you just don’t get it.
“This is the big leagues. This is the MLB. If I’m not here, I’m back at the bars at home, sloshing beers around. This is my one shot to make a name for myself,” Jimmy says. “I need to set my family up for success, and the only things in my control are working hard and making as much money as possible. [In reference to the others]: I don’t relate to the way you see the world. I don’t relate to the way you operate. You’re from Los Gatos. I don’t even know where that is.”
San Francisco was a miniature gold rush for Jimmy, and he felt a great sense of urgency to capture as much of the pie as he could. It was simply a path to a better life, but not a lifestyle. He tells me his friends back home are plumbers and electricians and firefighters and cops. Solid jobs, albeit with little upside.
“My friends made fun of me for working in tech. They said, ‘What are you doing, dude? You have boots back home and now you’re wearing loafers.’”
Two events took place that led to Jimmy’s first consideration of a real break.
First, his dad had a heart attack. It was an event that Jimmy struggled to digest in a comprehensive way. Then, a week later, Jimmy had a heart issue of his own and drove to the hospital.
“I was sitting there under the lights, at the ER, and I was thinking, ‘How am I supposed to tell my parents? Everything I’ve worked for is gone in the blink of an eye. It was for nothing,’” he says.
Jimmy was living back at home at the time after the company went remote during Covid. “I just told them I was going to play basketball with friends,” he says, with so much normality that I find myself at a loss for words. This was a Sunday—he was back at work that Tuesday.
The healthcare bill (after insurance) was around forty thousand dollars. He called the insurance company, asking for confirmation. Then he followed up with them a few days later, and the bill didn’t exist anymore. “I kept calling, and they said it wasn’t there anymore, and I asked why, and they said, ‘Don’t ask,’” Jimmy says. “What the hell is our healthcare system?”
He tells me when he got blood work done, his doctor told him his brain doesn’t produce serotonin or dopamine or “whatever it’s called.” He speaks as if he is trying to remember the name of a side dish he ordered at a restaurant the night before.
“I’d never had mental health issues before, and I wasn’t ready to deal with them,” Jimmy says. He seems irritated by the inconvenience of it all, as if describing an impossible mosquito he is trying to swat away. I nod and wait for him to speak, then he seems to look past my head and at the piano behind me.
“It’s collecting dust. I only play it twice a year,” I say. I look back at the keys and then at the music desk, where a canvas of a minimalist cactus I painted is now blocking scattered pages of music notes I once scribbled from YouTube videos on a rainy Saturday.
“Twice a year is better than none a year,” he says.
It’s in this moment that I realize Jimmy and I can never seem to replicate in ourselves the positivity we see in others.
“Why did you decide to take a break?” I ask. It’s been about a year since Jimmy left the startup. He’s been spending more time back home with his parents and his childhood friends.
“I physically could not do it anymore. I was going to hurt someone,” Jimmy says.
“You were going to punch a twenty-two-year-old sales rep? Really, Jimmy?” I say.
“No, I wasn’t going to punch an SDR—I was going to break their skull,” Jimmy says.
I can’t tell if he’s serious.
Jimmy and I scurry up and down the streets to Nob Hill in my car. We’re on our way back from dinner at some Mexican restaurant in Potrero Hill. He continues to be a person I call randomly, out of the blue, and he always picks up. I hand him my phone for music and then wrap my fingers around the wheel. I probably should know who Zach Bryan is by now, but I don’t, and Jimmy queues some of his favorite songs from the singer’s early days.
The sound of an acoustic guitar sifts through the car speakers, and Jimmy says, “My boys and I will listen to this album driving through the country roads back home, balling our eyes out. You can’t trade moments like that.”
In the words of Zach:
It’s the gettin’ by that’ll get us all down
So if you need me
Know that I’m bleeding
Somewhere alone in some coastal town
There’s no reason Jimmy and I should be friends. We run in different social circles and spend our time in different ways. I rarely go out, and he finds himself in bars on Friday nights. I move my body outside and he moves his at the gym. We both work hard, but in different ways. We reach similar conclusions on society—that it is riddled with perplexities and absurdities—but with different inputs of explanation. He tells me he might vote for Trump. I tell him the reasons that established reproductive rights are important for both men and women. We go back and forth, and he listens respectfully, validating yet unchanging. We understand nothing about each other, but maybe we understand everything.
Perhaps the only thing we have in common is that when we look down the slope of a ninety-degree hill, with the Bay Bridge shining in between cityscapes, we know deep down that we probably don’t belong here. We belong in some place where no one can find us. Some field with tall grass that whispers in the wind, where sunsets are fiery balls, blinding red; where dust picks up on a road; where our boots stomp on the ground.
We fear the same—that we might lose it all—and we don’t know when such a feeling might pass, if it ever does. We know this voice of fear keeps us in check, that maybe if the fear simply lives within us, forever, we can take a moment to breathe and enjoy the ride.