Episode 2: Chris Cheung | Subverting the System



"I think because of my great grandfather having made a fortune but losing it in the casino and making bad investments, my grandfather and father were of the opinion that you should find something stable, take care of your family...don’t rock the boat, so to speak"

- Chris Cheung, Co-founder of Boxed.com


Below is the audio transcript for Episode 2, lightly edited for clarity:


I. Are you willing to break the rules?



Hey there, it’s Lucia. Welcome to Episode 2 of Rock The Boat. This week, we talk to Chris Cheung, the cofounder of Boxed.com. If you haven’t heard of Boxed.com. they’re an online and mobile wholesale retailer that offers direct delivery of bulk-sized packages. They recently raised $111M in venture funding in their Series D round.


I wanted to chat with Chris because I was curious about what being at the helm of a successful startup would be like and how he got there.


We were connected through a friend of a friend which is how I got to hear Chris’ life story and wow, it’s a heck of a story.



Fun Fact: Chris was also named one of the most dateable men in New York City, according to the dating app Lulu. Photo Credit: NY Post


We speak with Chris about:


• Breaking rules, lots of them, and how they actually led him to a path of entrepreneurship


• Subverting the system and why it helped him succeed


• His desire to build something from nothing with his own two hands


• And his hopes for the future



If you’re someone who’s interested in starting something on your own or aren’t afraid to take the unconventional route, Chris’ story will certainly inspire you. 



Word of warning, there’s some strong language in this episode.


II. Chris’ Origin Story 



Lucia: I met Chris in a conference room at Boxed HQ in Soho NYC.


Chris: I’m Chris, I’m a co-founder here at Boxed Wholesale


Lucia: By most accounts, Chris was a pretty typical Asian American guy. He was born in New York City, grew up in Jersey, and attended an ultra competitive high school called JP Stevens. You can even say he was raised by stereotypical Asian parents.


Chris: My parents took care of all of our needs, not necessarily all of our wants, but our needs, just so my brother and I could focus on studying. Given their path in life, they knew that education was the best path ahead and would take care of anything getting in the way of that


Lucia: Since education was his parent’s top priority, they made sure to assign Chris with plenty of math problems. To them, it was all about rigor, discipline, getting those reps in. They believed the reps would get Chris better grades, which would increase his chances of attending a name brand university, which would then lead him down the path to becoming a doctor or lawyer.


Chris: It would be math class, algebra or something like that. The teacher would assign all the even problems of a particular chapter. My dad would make me do all the odd ones AND the even ones, and it got to the point where he would write more problems for me. On top of that, I think a lot of family friends were taking the Kumon classes outside of school.


Lucia: For those of you who don’t know what Kumon is, you’re really lucky. It’s a very popular tutoring center that originated from Japan. Asian parents would send their elementary or middle school children to either the math or reading class, where they did extra problem sets on top of their normal school work. Parents thought the extra work would help their kids  practice for exams.


Chris: Instead of actually paying for me to go to Kumon, he would just photocopy all their textbooks and make me do the questions. It was probably just like what they experienced in the Asian education system where it's was a lot of rote practice, just like a lot of afterschool activities, going through the same types of problems, just drilling it in. I never had time to hang out with friends, I was always just like doing homework whether from school or from my parents. There was no way in hell I was not going to be either like a doctor lawyer or have some kind of three letters after my name.


Lucia: Sitting across the room from Chris, I could tell that he was a very intelligent person. But Chris wasn’t interested in academics. In high school, he saw through the dysfunctional systems and started to try his hand at negotiating his way out of work. This was the first time he showed that he wasn’t interested in playing by the rules.


Chris: I think one time I asked my Dad, "Hey if you just help me do half of the math problems, then I can get the A. Looking at it backwards, if the main goal is to get an A, why don’t we make it a family effort?

Ultimately, he said no, you’re doing all the work. I guess what he was trying to teach me were the principles, the hard work, integrity - whereas the school system growing up Central Jersey probably just valued, What did you get at the end of the year? It didn't really value whether you intrinsically know the information or whether you retain it at all .


III.   Not Playing By The Rules: Cheating at Hopkins, Defrauding Facebook, Auctioning Used Clothes of Korean Pop Stars, Selling Twilight Tshirts


Lucia: Chris ended up attending college at Johns Hopkins. But without the oversight of his parents, he rebelled against the education system. In computer science class, for instance, he copied someone else’s code. One time the school’s algorithm picked it up and he got caught.


Chris: I got a degree in economics but the four years spent there I pretty much got a degree in cheating, lying, stealing, bullshitting.


Lucia: What?! Please elaborate.


Chris: Everything kind of laddered up into you know, whatever we needed to do to to just get in get out, get ahead.


The theme there was me learning to subvert the system. I didn’t want to play by the rules. In the middle of my sophomore/junior year, I studied computer science. It felt akin to studying Spanish in school. You’re just not going to beat the kids who grew up with it...I wasn’t going to be able to compete. If I put in 1000% effort, then yes maybe. But I had other things to do.


Lucia: At what point, were you just like fuck the system?


Chris: Around that time. If the deliverable was a file with letters that represent code, I could probably just get that from somebody else.


Lucia: In his college days, Chris was lazy. He found ways to cheat the system so he could focus more on hanging out with friends. Perhaps that framework of thinking, of finding the cheat code, comes from Chris’ love for video games and his disenchantment with the modern education system. I can see how Chris’ ability to spot opportunities attributed to his current success. However, it also got him into plenty of trouble.  Despite Chris’ effort to subvert the system, he barely graduated from Johns Hopkins.


Chris: Me cheating lying, stealing, bullshitting, didn’t necessarily amount to a 4.0 at all. I think it was a vestige of me being lazy as a kid, or having other interests outside of academia. I wanted to play video games, or read comic books. Anything that was able to increase my available time there and shirk away from my responsibilities having to do homework or study for exam


I didn’t know what to study. I think I went poli sci, IR, and something else. My dream was like, OK I’ll become a lawyer... I quickly found out that Hopkins seems a place where maybe you didn’t get into an Ivy but you’ll work your ass off and prove yourself. I think everyone there had a chip on their shoulder.


I ended up with an economics degree but barely graduated. I think I had a 2.09 GPA.


Lucia: Oh my gosh!


Once Chris graduated, he moved back to New Jersey to work for his old employer at a document research company. Just a regular job, nothing particularly entrepreneurial. But while Chris was there, his boss whose background was in film became interested in starting an online ecommerce site and asked Chris for his help.


Chris: That was my first foray into entrepreneurship. What does it take to set up a website, inventory, marketing...I never thanked him for this but that was the first real instance of, with just an idea and the right amount of interest in it, then you can do anything...That was the first time I realized, you don’t need to know everything. Coming from something without knowing everything, you can come at it with fresh eyes.


Lucia: This was one of the turning points in Chris’ life where he realized he could use his ability to spot opportunities for business. But once again, his parents didn’t approve.


Chris: Shortly after that I had a sit down with my Dad and he was like, there’s no way I paid X amount of dollars for your education and you’re getting paid $10 an hour. You have to get a real job. I resisted but eventually he came back and said, Take this job, he works for MTA. And so I worked for MTA for a while not doing much quite honestly..I literally just sat there and read books, and listened to radio...I just sat there and collected a paycheck, so that was kind of rough.


Lucia: After a year of working at the MTA and feeling bored out of his mind...Chris had to get out. He was thirsting for something more.


But due to the pressure he felt from his parents he didn’t start his own venture. Instead, he sought out jobs at various Fortune 500 companies; first as a sourcing analyst at Revlon and then a consultant at Goldman Sachs. He wasn’t a huge fan of the corporate cultures there. They valued materialism and titles, while Chris valued something else


I valued what  I could do with my two hands. I wanted to do something. I wanted to see what was possible.

Actually during that time, I started a few side businesses..I was passionate about doing something outside of work that could bring in some passive income….I went to see Twilight with my ex-girlfriend at the time *


Lucia: Sitting amongst a sea of giggling women and their mothers, Chris developed an idea for his first side project. He spent months working nights and weekends from 7pm - 2-3am in the morning designing Twilight T-Shirts.


I can tell that Chris’ mild and calm demeanor belies his incredible drive. He started taking the lessons he learned from college and applied them to business.


In 2009, Citi created a product called virtual credit which generated credit card numbers that expired after 24 hours. Online shopping was still at its infancy and people didn’t trust websites with their credit card numbers. The idea Chris had was to use these fast expiring credit cards to pay for FB ads.


Chris: When I realized that CitiCard had this system by which the CC#s would expire, I thought - what if I just pump credits through the card into my FB advertising? If the CC expires, they couldn’t charge it. So I was pumping thousands of dollars to FB new advertising system and i was sending people to my site and they would eventually purchase.


Lucia: Did it work out?


Chris: It worked for a little bit. Eventually FB caught on. They sent me a letter and told me how much money I owed. I wanted to fight it, and it was kind of ironic - I got sent a Credit Fraud Analyst position at FB from a friend, not knowing I was doing all this on the side. I thought it was hilarious. I had made more than enough to cover the fine.


Lucia: Talk about rocking the boat!


Chris: The only thing I asked for was that I wanted my Facebook account.  They ended up deactivating my account but I signed up with another email address. It was fine.



Chris speaking at the Rock the Boat launch event on January 15, 2019

Lucia: One thing I admire about Chris from his story is his tenacity and his unwillingness to back down from challenges -- even if what he was doing was questionable. Traditionally, as Asian Americans, we’re often taught to put our heads down and work hard. We’re not taught to play the game, to figure out the rules of the system and find the cheat code if you will. But Chris did and he played the game well.


Chris: I had another small business. You know I think spent $500 on a bunch of blazers the first month, sold it for $1000, took the money to buy $1000 worth of blazers. Eventually it caught up with my day job so I had to bring on a partner...we were expanding into other things because we found the right keywords and the right marketing.


My dream of building all these small businesses was kind of coalescing into this idea where I could actually give up my day job.


IV.     Itching to Create


Lucia: It was around this time that two major events changed history. One, the iPhone was released. And two, games like Farmville and Cafeland on Facebook were starting to take off. Chris and his grade school friends, Chieh Huang and Will Fong saw an opportunity. Mobile social gaming.


Chris: Any kind of startup you need a hustler, hipster, and a hacker. I ended up being the hipster, Will is the hacker (programming since he’s been 11 years old), and Chieh’s the hustler.


I’ve known Chieh since we were in middle school. He was always the funny, outgoing one who ran for student government...I remember one time in middle school, he made me laugh so hard I got detention


Lucia: With their respective skills and the opportunity at hand, they took on the world of mobile gaming.


Chris: With the new iPhone and the advent of smartphones, everything was going to take off. I quit my job, Will quit his job...we started an office in Will’s basement. We bought some basic tables. Let’s create a game. We spent about 9 months in the basement to create our first game. It was a parody of Office Life and was called Office Heroes…


It rose to the top. We were contacted by Apple, they loved it, and we were actually contacted by Zynga very early on. They were trying to build a mobile team. They saw mobile as being the future. And at that point we had brought on a couple of friends, we saw the writing on the wall. If they’re willing to acquire us when we have just 3 people, maybe we have something here. Eventually we took some money from a Japanese company. and grew the company to about 21 people, released 2-3 games in the meantime, and a year later Zynga came knocking again. We saw a great opportunity to take care of everybody. We didn’t necessarily want to keep doing games forever….


Lucia: Chris and his friends quickly found they didn’t jive with the culture at Zynga. They knew they had to move, but they weren’t sure what they wanted to do next.


Chris: It was kind of sad...but we were still pretty young. There was no reason why we couldn't make lightning strike again.



V. The Story of Boxed


Chris: In the end we eventually settled on a real problem, something we experienced : 2 people having to go all the way to 116th street to buy stuff from Costco and then bring it back. How come someone doesn’t just deliver this stuff? We quickly found ourselves in Chieh’s garage, fulfilling orders…


There were some days where there were no orders and then there were some days where there was a lot. Ten orders seemed like a lot. This in addition to building out an app.


Lucia: And that’s how Boxed came about.


Chris: That’s how Boxed came about.




The day we got our very first order, we had launched our app. The fact that somebody out there downloaded the app, trusted us enough to place an order, to put their credit card faith in us. That was a watershed moment...


If we can get one, we can get a million. We just have to convince everybody.


Lucia: Chris attributes much of Boxed.com’s success to the close relationship of the three founders. They’ve all known each other since they were kids growing up in Central Jersey.


Chris: One of the unique lucky things we have about Boxed is that we have a long relationship with each other. There’s all these horror stories about one founder betraying the other founder...I’m lucky that I can go to sleep at night and I don’t have to worry about that. I can walk to Chieh’s house.


Lucia: Chris and Boxed.com don’t show any signs of slowing down. Boxed recently raised their $111M Series D and rejected a $400M offer from a national grocery chain called Kroger. I asked Chris what he thought would be next for Boxed.com.


Chris: In the beginning you’re running so fast. You don’t have time to step back and reflect on whatever is going on. Our last company was only at max 20-21 people, so any increment past that it’s always a surprise…


We’re still on this roller coaster, you don’t really know where the highs and lows are


I’m happy to the extent that Boxed is now big enough that it doesn’t belong to any one person, let alone the co-founders. We have it up and running. We let it free in the world where people can experience it as a brand.


V.     What’s Next


Lucia: It’s been one helluva ride for Chris. From the days of defrauding Facebook to now being at the helm of a half a billion dollar startup. So naturally, I wanted to know what was next for him?


What drives him to keep pushing? Is it that chip on his shoulder from his college days? Or something deeper? So I asked and his answer surprised me.


Chris: There were two instances that drove that kind of mentality. The first was after I left school my girlfriend was cheating on me at the time...I remember very vividly sitting with my friend in the parking lot. And he gives me this one piece of advice that I’ll never forget, “Success is the best revenge.”


The second was… I found myself sitting inside an MRI machine. I thought I had developed carpal tunnel syndrome, having been at a desk job for a bit and then…


They thought maybe it could’ve been brain cancer, it might’ve been tumors


Lucia: Chris never followed up with his doctor and fortunately feels fine now. But that realization that life is fleeting, it stuck with him.

Chris: Life is quite short, life is very short and you just die...I wasn’t like that before. I think I was more lazy, if anything more carefree, just wanted to hang out with friends. But this was like a one two punch. But now it’s like hey,


If we’re gonna have success, if we’re gonna make it, let’s get there yesterday.


Lucia: Let’s get there yesterday. I can sense his impatience as he said those words. I couldn’t help asking that question of myself. What if the same thing happened to me and I had a time limit to my existence? What would I do? What would you do?


What Chris wants to achieve extends far beyond just himself and his family. He wants to create something great for generations to come. Most of all, he wants to be remembered.


Chris: I looked at where my parents came from. Obviously with them focusing on education, they wanted a stable existence for their children. But there was a part of me that thought, they sacrificed all this in a country where English wasn’t their first language, they had to go through all these struggles...


I wanted to take that gift and blow something out of it. I think my great grandfather having made a fortune but losing it in the casino or making bad investments led to my grandfather and father being of the opinion that if you find something steady/stable, just take care of your family, don’t rock the boat so to speak - you’ll be ok. I just couldn’t go the same path.


There was something in me where I thought about what I wanted to do with my life. I didn’t want to do this just for my family or my children.


I wanted to be that most honored ancestor, someone who could take care of a whole generation after generation of offspring, a dynasty almost. Why not aim for that?



Lucia: As Asian Americans, we’re often told to follow orders, put our heads down, and work hard.


We’re told there are no shortcuts, we have to struggle to be successful and put ourselves in positions of discomfort. However, when we put our heads down and only focus on what’s in front of us, we miss the bigger picture. We miss alternative paths, we miss opportunities, and we sell ourselves short.


My key takeaway after speaking with Chris is that we don’t have to believe what everyone tells us is the right path. We have the ability to create our own paths, make bold moves, hack the game of life, and come out swinging.


Rock The Boat is a podcast elevating the stories of Asian leaders, founders, and pioneers in their fields. Through candid and thoughtful conversation, the host Lucia Liu uncover stories of their upbringing, Asian identity, and the movements they've built. 

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