Have you ever wondered what it takes to build a company from your garage to a public entity?
In this episode, Chieh Huang shares the raw, unfiltered story of building Boxed from a garage into a national e-commerce brand serving tens of millions of customers, and the emotional toll, unlikely breakthroughs, and market forces that shaped every chapter of the journey. He reflects on the lonely months of almost no orders, the overnight surge that changed everything, the pressure of becoming a public company CEO, and the reality that even the strongest operators can’t outrun macro cycles.
Chieh also opens up about what happens after the final chapter closes, the exhaustion, the identity shift, and the unexpected necessity of real recovery. His honesty about the highs, lows, and lessons he’s taking into his next company makes this a powerful episode for founders navigating their own versions of the broken-glass analogy.
Takeaways:
From Humble Beginnings to a Notable Success: Chieh Huang started Boxed in 2013 right from his garage, with only dreams and a strong will to succeed. Within a few years, Boxed scaled to become a renowned online wholesale retailer, serving millions.
The Challenge of Maintaining Purpose: Chieh emphasizes the importance of cultivating an intrinsic purpose within a company. At Boxed, the sense of purpose wasn’t predefined but evolved over time as the team grew, particularly among the fulfillment center workers.
The Rollercoaster Ride of Fundraising: Chieh’s journey wasn’t without financial hurdles. While initial investments were relatively easier owing to his prior success in the gaming industry, subsequent rounds posed challenges, reflecting the inconsistent nature of venture funding.
Consumer Business Dynamics: Chieh discusses the unpredictability of consumer businesses, highlighting how a single viral moment or endorsement can drastically influence a company’s success, unlike enterprise businesses that grow through steady acquisition of clients.
Public Company Experience: Huang’s experience in taking Boxed public via a SPAC (Special Purpose Acquisition Company) taught him that public market dynamics significantly differ from private ventures
Handling Burnout: Chieh and David discuss the inevitability of burnout in an entrepreneur’s journey and the importance of managing it proactively through short breaks, personal downtime, and stepping away when necessary to recharge.
Quote of the Show:
“Being a CEO is like trying to be the greatest of all time in a broken glass eating competition.” - Chieng Huang
Links:
LinkedIn: https://www.linkedin.com/in/chiehhuang/
Website: https://boxed.com/
Ways to Tune In:
Substack:
Spotify:
Apple Podcasts:
Transistor: https://podcast.notanotherceo.com/
#NotAnotherCEO #BusinessSuccess #Boxed
Chapters:
00:00 Intro
00:46 The Journey of Boxed
02:42 The Purpose Behind Boxed
07:14 Starting in the Garage
09:23 The Big Break and Rapid Growth
20:36 Fundraising Challenges and Successes
26:02 Navigating Market Ups and Downs
32:09 Reflecting on Past Experiences
33:59 Journey to Going Public
36:26 Challenges of Being a Public Company CEO
39:22 Navigating Investor Relationships
44:17 Balancing Work and Avoiding Burnout
50:03 The End of Boxed and New Beginnings
55:03 Early Entrepreneurial Spirit
57:54 Role Models and Mentors
01:01:25 Core Motivations and Advice
01:05:51 Outro
Transcript:
Chieh: [00:00:00] So you’re trying to be the greatest of all time, but most folks don’t realize the sport in which that they’re trying to be the GOAT of is a broken glass eating competition.
David: Today’s guest is Chieh Huang, one of the most authentic founders I’ve ever met.
He’s the co-founder and former CEO of Boxed. Boxed was an online wholesale retailer that Chieh started in his garage and ultimately scaled to serve millions of customers across the country. He started Boxed in 2013, took it public in 2021, and ultimately had to shut down the company in 2023. Che is a serial entrepreneur before Boxed.
He was part of the founding team at Astro Ape, a mobile gaming company that [00:01:00] Zynga acquired in 2012. He’s also a board member at Six Flags and Advisory Board member at McLaren Racing. He dedicates a lot of his time to sharing his stories of resilience, leadership, and building businesses with the next generation of founders.
I heard him speak at a founders’ event a couple months ago and immediately reached out to see if he would join me on the show. Please welcome Chieh.
Chieh: Thanks for having me, Dave.
David: Excited to do this. Excited to do this in person. Thank you
Chieh: this. I, I was, uh, sorry to start off, I, I know you were gonna ask questions, but I actually had a question about the show, Yeah. so, Is it, uh, is it, oh, not another CEO or is it like, I
David: of it? I, I thought of it because I, no one’s ever asked me that question. I thought of it because I I, to a lot of podcasts. Yep. A lot about business and everything else, and I found that I, the podcasts were getting increasingly fluffy.
Oh, okay. Yeah. And I started feeling like there was all these conversations that I was listening to. I’m like, I know that company, or I know that person, and that’s not actually what happened. And so then when I was telling people, I’m gonna start a podcast, they said, someone said to me [00:02:00] another CEO
podcast and said, no, it’s not another.
And they said,
that’s
actually a good idea. So it was basically this whole, trying to come up with a name was really, really difficult. And then when someone said that, I was like, actually, that’s exactly how. Describe it,
Chieh: dude. I, I, uh, because, you know, I, just, different ways of reading it. I thought I was actually really excited feeling like, oh gosh, not another CEO and like, you know, uh, but, uh, but it seems like most of the episodes are people are very authentic.
and they’re not Very authentic. Like, I think you’ve done a good job of, uh, cutting the fluff out of it. thank you. So I’ll try to carry on
David: that
tradition. Thank you. Oh, I know you will. That’s why I’m excited to have you. Uh, so first question, what is the one thing, big or small that you did at Boxed that had the biggest impact, and you do, again, if you’re CEO, of another company in the future?
Chieh: so that one thing, um, I I, it’s hard to take credit for in terms of like on day zero, this is the one thing that we did well, and we planned it from day zero. Um, it was actually through time that we instilled a sense of purpose in the company. Um, and I think we often [00:03:00] conflate like ro the royal we like in general, like we, we conflate, um, uh, mission goals, uh, and purpose.
Um, or actually goals, mission and purpose. So goals, especially when we’re public goals, are to make or meet or beat, uh, quarterly earnings kind of expectations. Uh, your mission, uh, is perhaps something that you want to do for the customer, but the purpose oftentimes is actually what’s not written on the wall.
It’s how everyone behaves when just it’s you and one other person in a room making a big decision, and there’s no guide on how to make it. What is that underlying purpose that ties everyone together? Um, and for, for us, that wasn’t on day zero. We said, okay, this is the purpose of the company. But through the many years, uh, you know, especially as we began to hire more and more frontline, uh, team members in our fulfillment centers, that that underlying purpose became the purpose of the company.
Um, I know a lot of founders, uh, on other shows potentially, they come on and say, this was the purpose of the company on day zero. I can’t take credit for that. That [00:04:00] was through a very
hard
road of discovery that we found purpose in ourselves,
David: in our company. And
when you found it. Did you somehow take that and amplify that?
You know what I mean? Or was that just so organic? It just permeated the company?
Chieh: in, in some ways. Um, it, at first it was organic and it began to permeate the company. Uh, meaning we started to do well by our team members, especially again, the fulfillment center teams, uh, because simply we thought it was one the right thing to do, and two, it was also good for business.
It’s like these are the folks that are actually packing the Boxes, unloading the trucks, getting, de uh, determining how someone was gonna get their order. Was it gonna be packed in a haphazard way or is it gonna be very neat writing a handwritten note, they could write whatever they wanted to. So what were they writing on the cards?
And so all these different things. I think again, not only the right thing to do, but also write for the company. Um, over time though, I think we got more and more publicity as being that. And so as folks were actually joining the company, they knew the type of company they were [00:05:00] joining. Um, uh, and then also once they joined, they also realized that, oh, it’s not just a glossy brochure, this is actually how.
David: The company
So when they would join, they had read about or heard about, but you told them when
they
joined?
Chieh: we still, we actually really didn’t talk about the purpose of the company. We, Yeah. But once you came to the company, it was pretty, uh, uh, apparent from day one.
Wow. So I always like to say that we never, it wasn’t in our core values to treat, um, our team members well or Right, uh, uh, or to make sure that we’re treating those folks, um, uh, the same as if they’re making the most at the company, even if they’re making the least. Um, but if you walked into a room, um, and, and someone said, Hey, you know, we can save a lot of money by cutting all the benefits at the fulfillment centers, um, you would get laughed outta the room even though it’s never written anywhere.
as as a,
as a cardinal rule.
Wow. Uh,
nor was
David: ever posted on a wall. Wow. I, I, I do think people have talked about values and mission. No one has actually said it in that [00:06:00] way. And that feels like to. Drive people when you have like a real purpose and it’s that organic.
I don’t know how to explain. Like, I feel like that probably gives the company 10%, 15% more throughput or Oh yeah.
Drive. Or it just, it’s like that extra boost every day.
Chieh: feels like. exactly. Because at the end of the day, we all have different choices, uh, in life. You wake up every day, you could, you quit your job today, you quit your job tomorrow. Um, and so why are you not only kind of going to that job, but why are you excited about it?
You know, that doesn’t, of course, money can be an issue, uh, it can be one of those things, but that starts to wear off over time because there’s all probably a bunch of other companies willing to pay you the same if not more. So why are you sticking here? And also why are you continuing to come and be excited?
Yeah. Um, and then also I think,
I don’t know if you can force that level of, of purpose or authenticity. It is just, it just naturally happens. Um, and everyone will have their own journey. Um, it doesn’t matter how [00:07:00] rudderless a company.
is, they will have a purpose. It might not be a purpose they like. Yeah. Um, but I guarantee you there’ll be some through line amongst the whole company again, no matter how, uh, I guess haphazard, uh, in a way
that
David: culture was said at that company. Yeah. One of the things, so when I read about, Boxed and I have heard the story and listened to a bunch of stuff, there’s always this thing about
like, starting in your garage. and, you got pretty big pretty fast. Did it actually start in the garage?
Chieh: It
actually started in the garage yeah yeah.
Actually,
David: it’s not like a thing,
Chieh: No not
a thing.
what was
I
I at the time
you know, I don’t know if it’s an embarrassing thing, but at the time I was already, like, when we started Boxed I was already 30. So, you know, you’re sitting there and you’re like a 30-year-old sitting in a garage and you’re like, you know, and like, when the kids, you could just tell the kids would cross the street before crossing in front of your garage.
Because like their parents were probably like, don’t go in front of that weird dude, like, you know, selling toilet paper out of his garage. So it wasn’t a very proud thing [00:08:00] at the time, but I look back and man, was it like, it was a really awesome experience.
David: How far did you actually get in the garage?
Chieh: oh, we got, like, we got to the point where there were people I didn’t know who joined the company
in my house.
Yeah. And so, we also had to start, yeah, there were trucks coming down our driveway. We had to like, undrill the garage door and make
it a screen, like a screen mesh instead. it was a whole
thing. How
many years like About we were there for a good year and a half. Because remember like when
you start in a garage, there’s this like, I guess romanticized version of it.
It’s like, we’re starting today, guys and gals. Tomorrow the orders are gonna come. And then by week four you’re like, oh my gosh, this is going so well, dude, we were there for months. Sitting in our garage, in my garage with like nothing to do. And it was like days where no one ordered a single thing. And I remember one
of the, our first team members who quit [00:09:00] his kind of decently high paying job to sit in the garage with me.
He was like, dude, he’s like, there’s 300 million Americans and we sell things that every one of them actually uses.
And not a single person ordered from us. Is this gonna be a thing? And you’re sitting there, it’s like,
I don’t know. And so you start to, there’s a lot of self-doubt that creeps in when again, when you’re sitting in a quiet garage just staring out into the ether.
but luckily I think we, had our big break.
David: And what was that? I mean that, to go from there how big was it like at the peak, peak, peak, how many
people were using millions, right? I mean,
Chieh: oh yeah. Like at our peak, I think, by the end of Boxed, I think tens of millions of Americans had used the service.
So, and to this day, I still, you know, if I meet someone, they’re like, oh. You founded Boxed, You hear like, oh, you were my lifeline during, you know, COVID
or I used
you
all the time at my office. And
David: but it was before cOVID That it took off
Chieh: for sure. So we started in 2013.
and so, um, uh, [00:10:00] someone like a influencer who is regularly on the Today Show, started using our service, And she loved it, and she and the Today Show wrote to us and said, and this is again, when we were maybe getting three orders a day, five orders a day, like, and she was wanting three orders.
Yeah. And so she said, do you mind if I talk about you and plug you on the show,
tomorrow or,
the day after? And, you know, we were like, this is clearly spam. We’re like, is this real? Has anyone said, is this an IQ test? Has anyone said no? and so she said If, the answer is yes, then bring kind of what you want me to bring onto the show by 5:00 PM at, the studio.
And so we rushed over there, dropped it off, and they talked about us. It was like Hoda, Kathie Lee and this influencer. and I remember we’re sitting on the couch watching the show live. We’re like, this might be good.
And then within that hour, then it became that quintessential moment where all [00:11:00] these orders started to flow in and then we’re like scrambling in the house.
And then by the end of that week, we were calling people we knew, being like, Hey, come on. If you have some hours, just come work nights at this
guy’s
house.
And so that’s when it really took off.
David: Wow.
Yeah.
It’s amazing how I’ve never built a consumer company. I have very little exposure to consumer companies.
It is amazing how something like that can actually, it might be good or bad things. Yeah. Yeah. I don’t, know. I don’t know.
Chieh: Be a good thing,
David: But it’s amazing how that can like actually instantaneously change it. You can’t And, and I don’t know any enterprise business that could get changed like that. Yes. But consumer businesses, I’ve heard story like a Shark Tank type story or this story
and one. Time on the air or something, or one
influencer,
and
that’s it
Chieh: totally
So yes, that’s what makes consumer businesses so, f. so potentially attractive, especially to first time founders. It’s like, I have a problem. I personally have a problem. I know all my neighbors have the same problem. Can I solve that? Um, and [00:12:00] so, and once you solve it, what makes it so, uh, I guess, unique and almost so addicting in some, by some uh, standards.
It’s like the first time you see someone in the wild using your product,
It’s a really, cool experience, man, it really is. And for me, especially when I, I still remember not my direct neighbor, um, but someone, um, uh, kind of in an adjacent neighborhood used our service. I was driving home and I saw one of our Boxed Boxes outside of a house.
Like I remember slamming on the brakes and being like, oh my gosh. Yeah. Like, we made it. And, and yeah,
it just. it, it, I mean there’s something alluring about that..
That’s
David: I mean, when your friends or family or kids’, friends, I, I, my friends who do have consumer type businesses, you feel that, where they’re like, oh yeah, someone’s using my, someone who like doesn’t know shit about technology or like, they’re using my product and that I can understand that that’s a different,
honestly, it has to be a different sense of pride.
Chieh: Totally. Um, it also can, um, there’s interesting dynamics that come out [00:13:00] of that as well because, um, you become customer service for millions of Americans uh, that are using your service. So, uh, somehow, inevitably like your information, someone’s like, this is the, his email address, and so you’re getting customer service emails, but I, I enjoyed it.
Or if you’re seeing friends, they’re like, oh, my last order.
You’re like, ah, you’re, we’re here watching the game where I’m like, I don’t want to hear about your last order, man. Uh, but you know, it’s, um, uh, it, there, there’s certain aspects of it.
The, the most interesting part was that. Uh, To engage kind of our designers.
Uh, we made it so that we had these limited edition Boxes, um, uh, that we would have this other plate so you can print the outside flap, the top of the Box. Yeah. Um, and so each artist got to kind of make their own plate. And so, you know, they had a different take on what they wanted to build and, and what they wanted to kind of design.
Um, one of my co-founders, who’s the head designer as a giant
f to me, uh, just, just made this weird caricature uh, kind of [00:14:00] version of me. Of you. Yeah. And it got voted and I was like, we, we can’t do that, dude.
We’re not doing that.
And they’re like, okay, fine. It was just a joke. I’m sorry. We, we won’t do it.
Uh, they did it anyway. Uh, and so it ended up being the only
plate that we, we started printing.
David: So your your face was on everything?
Chieh: Yeah. Uh,
so the largest size of Boxed, which was our most popular Boxed, um, my face was printed on the top. And I remember, you know, just on New York, at at our peak, you’d see Boxed Boxes, like. Quite, yeah. Quite prolifically on, on the street. Um, and so I would just see my face on all these Boxes and every time
I’d be like, oh my gosh. oh my gosh.
Um, yeah. ‘cause they weren’t in great shape and Yeah.
David: and you, and you, you had a gaming company. You, you were part of founding team of a gaming company before.
So you’ve been in consumer, I mean, you’ve been in consumer, and is, is that what
Chieh: draws
David: it is that why you were drawn to that?
Chieh: initially yes. It was what I knew. So we made games when the iPhone first came out, we were one of the first social mo [00:15:00] mobile social game studios for the iPhone and for for Android when it first came out.
Um, and so we knew B2C, we knew how the consumer interacted on devices and we basically said, okay, games was kind of the first wave. Um, we actually think these people will transact their daily lives on these
devices,
which sounds completely innocuous today. But rewinding back to 20 12, 20 13, some of our first customer service emails were people saying, wait, you, you don’t have a website?
You want me to put my credit card into my mobile phone capital? Ha ha. Good luck. You know, um, that was just the state of the world less than 15 years ago. Um, but, uh, that thesis borne itself to be true
and we rode the wave. Uh, in ensuing 10 years.
David: What do you think is the next wave for consumer?
Chieh: I, I think, um, we, you know, at Boxed we always talked about it and we actually built this, it actually worked really [00:16:00] well for businesses.
Um, We started based upon the data we had on how you ordered and what you ordered. We just thought, well, why do you still need that, that step of going into
the app and clicking what you want? Why shouldn’t it? Like now, back then it was machine learning rather than just true ai. Why couldn’t we begin to predict what you were gonna order?
Now, for a consumer that’s a dangerous proposition because the moment you get shaving cream when you didn’t need it, and you got it charged a credit card and showed up, you’re like, I didn’t need it
or I didn’t want it. That becomes an issue, right? But for most businesses like that are just stocking the pantry, right?
Yeah. They’re gonna consume it anyway. So it actually worked really well for, for businesses. But, um, to answer the que, the reason why I brought that up is that
we never had, I, I thought the technology to make that really, really amazing. Um, but now I think you can actually make it pretty amazing and that I think the next wave over the next 10 years,
I, I think the automation of your life for the more mundane tasks.
Will probably be a big thing in [00:17:00] consumer. So, you know, there’s no reason why with five years of data on how often I order shave cream, why AI can’t
predict when I need it. And yeah, I don’t need to go and click
David: button anymore.
Chieh: Why couldn’t it just, uh, be sent to my house?
David: so automation the mundane.
Chieh: The mundane. Exactly.
David: which by the way, I think is the same for businesses. I think when you look at, when people say, oh, it’s gonna take everyone’s job, I, at least in my opinion, from what I’m seeing, I don’t know if it’s gonna take their jobs,
but all the mundane things that they’re just doing over and over and over that should all get taken care of.
Chieh: I, think, and
also the AI is more in the mainstream these days, or not more in the mainstream.
It’s firmly in the mainstream where even seven, eight years ago, if you were like, Hey, we’re using a mix of machine learning and your habits to predict, folks were like, what? I don’t, what is this? Like, why, you know, but now. If you say that to someone on the street an office manager, they’re probably like, okay, great.
great. Like, I [00:18:00] hear it about it all the time now AI’s making my life easier. Like, great, why wouldn’t I do it? Um, so yeah, for any entrepreneur out there that that’s, if
David: you
Chieh: haven’t, if that service does not exist, go for it. Um,
David: I think that that idea for you, that you say that I want to, something interesting from my experience, like my career has been in SaaS and
from the days that it wasn’t called saaS or cloud,
Chieh: those days, what was it called back then?
David: It was called, uh, the, well, the first company I was at was a Cloud PBX business, but at that time it was called iP centric or something like that, or,
um, hosted pBX. was the word instead of cloud. It was, it was hosted in some other person’s cloud. And so we just said hosted pBX, that was actually the first term that was used, and there was a lot of that being talked about, hosted exchange hosted, and so some, somewhere.
Was hosting that for you. Yeah. Yeah. Um, but when you think about that people, it was the same as people saying, I’m gonna put my credit card in. Back then
it was people saying, i’m gonna put my [00:19:00] data in your cloud. Like in, not in my server, in my office. Yeah. It was The exact same I could only imagine
And like, where is it?
Like
who’s,
who
can
have
access to it. Exactly. Who can
have physical
access to it. Exactly. but
it’s exactly the same thing. And then at some point it, it turned over where they’re like, why would I leave it on a server in my office? Yeah. That can get hacked easily. Yeah. That can get, you know, some disaster happens and I have no access to it. And so, but I think in ai, my observation recently is like that we went from not being comfortable to comfortable in a matter of
months. Yeah. Yeah. Versus a matter of five, seven years.
Chieh: Yeah. Like a
whole generation
of
products.
Yes.
In
the enterprise space needed to educate the market in order for folks to be more comfortable.
with that. I totally agree. And, but going back to what I originally said, it’s like that, I think that’s what makes consumers so alluring. is That any day you wake up, it could be your day. As a consumer founder. It could be that, I don’t know, the hottest star today wakes up, goes on, uh, TikTok and [00:20:00] says, has anyone used this cream?
This thing is amazing. Like, I woke up refreshed. I looked better. Like, and that could be your day.
And I think part, which is why I of of consumer, yeah,
David: it’s crazy. I mean, it’s scary to me because there’s no real, it’s hard to know what is, like the, what am I doing to really, like what did I just get lucky? Yeah. Yeah.
did I orchestrate that? Yep. You know?
Chieh: yeah, i, i, I, um, i’d like, I love it.
Um, and I love the founders in consumer. I don’t know if it’d be consumer
would be my, my next company. So yeah, I, i’ve done enough.
I’ve done it for 15 years, so i’ve seen enough. Um,
David: so you raised, you raised a lot of money for Boxed. I think if I looked it was 250. Some, some,
yeah. Yeah. 200 million,
250 million a lot.
Chieh: Which, which is. Surprising. If you think about it in today’s lens,
where two 50 is like for a late stage company that’s like, probably not that much. Right? Which at the time i, when we were, you know, I remember our series a was like 7 million [00:21:00] and folks were thinking, wow, sure. You wanna go that big on a series A, you know, um, where now, you know, seed rounds like pre-seed
or 20 million, you know, um, so yeah, the world has changed so much.
David: And, and so when you went through the fundraising, was it easy day one,
like that 7 million that you raised? Was that, um, or the prese,
you know, when you first raised, you were in the garage, I assume.
Chieh: Yeah. I, I’m, I, was awfully blessed that, uh, our original gaming company was quite a big success. And so it was, you know, folks who had invested, they’d all made money. And so
I think having that initial win under your belt, um, buys you the credibility for folks to say, i’m betting on you next time, so whatever you do, just sign me up.
Like, If you wanna tell me the idea, great. If you don’t, great. Um, but here’s my a hundred thousand dollars check, or here’s my $50,000 check, or here’s my half
a million dollar check. I don’t think, maybe not half a million, but a few hundred grand. Uh, folks
were, uh, happy to
write up,
I
guess
David: a
blind
check. Yeah.
To
Chieh: whatever you
were doing next. Okay. So
David: So that’s how you kind of got
Chieh: that’s how you kind of got off
That’s how we got off the [00:22:00] ground But then rubber hits the road and Series
A. It’s, it’s, it’s Series A. I often say it’s like the hardest round to raise. I, I thought because there’s just enough data, right? There’s just, just enough data to make anyone who loves your idea or who is critiquing it be right.
Mm-hmm.
So you can cut the data and say, this thing’s a disaster, or this thing is the
next rocket ship. Um, because the cohorts aren’t firmed up yet. You know,
David: it,
Chieh: it just, you know, it it was a really hard round to raise. everybody Okay
David: so that was har. So compared to that where you could get in the first round of, what was that pre-seed or angel round? Yeah. You were able to get from anyone who had
backed
your last company, and i’m sure once that started it kept going and then the a was hard.
Chieh: Yeah. Well, what I found and, and this is probably different for many other entrepreneurs, I found early stages, especially seed or pre-seed, they’re betting on you. And then like a mild part, they’re thinking about the idea, but for the most
part they’re betting on you that you’ll figure it out.
Um, [00:23:00] then as you get to a and b, they’re betting on the idea and the promise of the idea and the execution of it. And then I think once you get to like b plus c and like
betting on you, maybe, maybe not bet on idea, well, we know if it’s a good
idea or not. It’s just a spreadsheet, uh, analysis, right. Once you get to the later
stages. Um, and so that was a,
a real evolution of how I, I had to think as we were pitching those
investors.
David: How long did it take to raise the a
Chieh: took a
few months.
Um, this,
is a while ago now. Um, how about the B?
Um. The B went very quickly.
‘cause the A we did every, and this was great in the sense
that we kept our series A deck and we said, this is what we said at seed. Um, and a, and this is what we accomplished with it. And it actually, we were kind of outpacing what we thought we were originally gonna do. And so that was a lot of validation.
So I remember we had a few meetings, um, we didn’t even like kind of, we certainly didn’t boil the ocean within a few meetings. Our first term sheet [00:24:00] was there.
And uh, it was great valuation when someone we really liked and they said, well, we can close within 30 days. And so
as a founder you’re just like, I wanna get back to it.
Right? And so that’s what we did.
David: That’s
a
really
good idea
to,
to show the deck. Yeah. That’s a
smart
Yeah.
Chieh: I never thought about that.
David: Yeah. To show that. People have told me what did you, when they
finish their did show Yes. No, that’s a really.
The one, the one friend I have right now at a company, and they’re raising like every six months and they’re growing like crazy and everything.
He actually said it’s exactly because of that, where the deck was out there and people saw the deck, then heard the new numbers and said, wait, the deck
Chieh: that was
pitched was lower
David: than what you’re actually doing.
And then they preempted. Is that a bad thing?
Yeah. And then they preempted and then the next deck, you know, and, but
Chieh: that’s
David: a really interesting idea. Yeah. You would actually share that with the series, like you the series A and,
Chieh: Yes. So we shared kind of our original projections And this is
David: how we’re,
Chieh: we’re, kind of [00:25:00] projecting out. series
C, how was that? Uh, was it a So C was betting on us. So because we had the, the Zinga win, that was good.
A was difficult, B was easier. And I, this is all curved, right? So when I say easier, it’s still not easy, but you know, easier. Uh, C was difficult.
Um, d was, I think around COVID actually. Uh, and so d was quite difficult. Um, and then e was your pre IPO round. Um, and then as I learned it, no one likes a series f. Uh, and
so, um, uh, so yeah, that’s I guess the ups and
downs of our fundraising journey.
David: So at the last, so it wasn’t always up into the right
and
Chieh: No,
No, no, I think any entrepreneur that has been an entrepreneur for 10 years on the same journey, it would shock me if they had just easy rounds the whole time. doesn’t matter the what company it
is, there are, there will be a time when it goes sideways.
Um, and so those are the, you just have to time it so you’re not raising money when it’s going sideways. And unfortunately,
if it is going sideways while you’re raising,
David: [00:26:00] those are extraordinarily hard in people rounds.
And not just, let’s be honest, it’s not also just the company, it’s also the market.
Chieh: And
David: market could
go sideways. Your, your company could be doing fine and the market goes sideways oh, all of a sudden everything changes.
Chieh: Thank you for that clarification, because that’s exactly what I meant. So it’s not just what you did, it could be the market. Um, and so yeah, there’s, you know, during the time of Boxed, we had, like. I would say for venture, we had at least
not, at least, we had three bare markets during that 10 year stretch where like consumer and e-commerce was not in then it was in, then it was hot, then
it
David: not
Chieh: hot, then it was hot again. So, you know, yeah. only so much you can control.
David: Yeah. I think the one thing is having been through the same journey and
those ups and downs and having to raise like literally at the peak of like february of 2020, march of 2020, which was terrible having to do that in, in 2008, 20, i’ve been through that same cycle and when the money is there, oh yeah, you [00:27:00] take the money.
Chieh: Oh yeah. It, and it’s also a nice edge, right? Because january to april the world has frozen. Yes. But then if you wait six months after, so later in 20, exactly And early
21, then suddenly it’s like we can’t find enough good things to invest in. Like, come on, bring the idea and it, so, you know, and there was no way. Any human
being could have controlled that. Um, but you just had to ride the wave, uh, as an entrepreneur.
David: yeah. I think when the, when the windows are, I mean, we’re in that window right now. Yeah. We are in one of those windows right now for sure. That could end tomorrow
for sure. Or could go on for six. You know, you have no idea.
Chieh: think as I’ve done more and more companies, I think the one thing that has permeated my psyche more and more is that I’ve become way more paranoid because, you know, i, I, I hate to sound like the older guy, but sometimes you’re just like, listen, I’ve lived through tough times and the market changed like that in oh eight. Market changed like that in 2020, but
David: that’s the reality of it, man. Like,
[00:28:00] overnight. Overnight, overnight,
Chieh: September 15th, 2008 is when I started my professional career.
Um, September 14th was when Lehman collapsed on a Sunday night at 11:00 PM
or something like that. Next day i’m at work and we, my office was across the street from Lehman’s and you just saw thousands of people stream outta that building with banker’s Boxes. And That happened No. There were signs like Bear Stearns had collapsed kind of the summer prior, but September 15th, 2008, that if you go back and look at CNBC
vintage footage of that day yeah. People were pretty, pretty surprised. And think the bottom had fallen.
David: Exactly. So you don’t, we don’t know what it, what it’s, what is the bottom gonna
be? Be here, you know? Exactly. But something’s gonna happen.
Totally. Something’s gonna happen. Um, now we’re seeing valuations. I mean, I saw a company doing half a million of revenue, half a million of revenue, and they raised that like 400 million post and they did that six months after their previous round at a hundred, which like just feels
Chieh: I almost choked my drink.
Yeah.
the way, because I,
David: it it [00:29:00] just feels like the peaks of these other times where something doesn’t, something is not adding up. You know,
Chieh: I, I don’t blame the entrepreneur and in a lot of ways, hats off to them. ‘cause if
they’re squirreling that away, um, then they’re gonna survive winter. Um, when
you look@thefirst.com boom and bust The folks that actually made it to the other side,
some of the most prolific companies that we know today. Um, but there were a lot of great
promising companies that just didn’t have enough to go.
Um, and unfortunately they fell by the wayside.
David: So, but you just said something real. I think if someone’s listening to this and they are one of those types of companies, it is squirreling it away. Yeah. And not assuming that tomorrow the same money is available at
the same valuation. Yeah. Because most likely it will not be. Yeah.
Most likely. And so if that’s the case, you have to put it away.
That’s why I tell a lot of the 25-year-old entrepreneurs crushing
it with their aI company and they’re raising all this money, i’m like, don’t spend it.
Like, you have it,
Chieh: you know? Yeah. I, I,
um, a very prolific investor that was, an investor in Boxed, [00:30:00] um, after we raised our first a hundred million dollars, um, he said, I thought he was kidding, but he said, take 20 of it and 80% of it, we, we consider amending the doc so that the. It’s in a separate account that the board that you have to get board approval in order to access.
Whoa.
Um, and at the time oh, it’s like, that’s lunacy that what, you know, you worked so hard, you finally got to a stage. You had plans for that a hundred million dollars on how you were gonna grow it.
But now, kind of a decade after that conversation, I I know his mindset now because, you know, for a bunch of reasons, because you never know where the world goes. But also more importantly, in times when resources were not as abundant, that’s when a lot of the good, um, kind of, uh, uh, I guess habits uh, uh, of a company are, are formed. Like that’s when the time that those habits are formed, because you don’t have a lot, so you have to be scrappy and that you have to make do with what you have. Whereas when you have a ton of [00:31:00] money, you know, that money can kind of cover over some, some potential, uh, um, kind of, I I guess parts of the business that can be solved by money. Mm-hmm. Uh, but fundamentally are not. Um,
David: actually, when
you look at the, like you said, I think it’s kind of like that li limiting yourself or whether it’s forced or manufactured drives the innovation to even think, like just look at the business in a different way and say, do we actually need this?
Do we actually need this? I mean, it’s, it’s a ter doing layoffs is a terrible, terrible thing that I think any CEO will say, it’s probably the worst moments of their kind of career.
Yep. But many times after a layoff that I’ve done or that I’ve talked to other CEOs about, they end up saying, wait a minute, I actually we’re moving faster.
Yeah. Where at we’re we’re more efficient, we’re doing better, we got rid of a bunch of projects that weren’t even important to us, and it’s a forcing function to kind of see that.
Yeah. It’s hard to remember [00:32:00] that, you know, when the money’s available. It’s hard,
but, but I think you’re making it, it’s a good point of like, you get better in those times, even if it’s. The uncomfortable of those times. Yeah. I couldn’t agree more. Um, so now whatever a company I start next, I feel like that’s probably what the board’s gonna say.
Chieh: It’s like, Hey, remember that podcast where you said we’re gonna amend the docs? Um,
but it’s a good inspiration that, and a good reminder even for me that. Um, even if it’s not, you actually put it in the docs so that you need to access it as
David: a
Chieh: special vault, even if you just start a separate account. It should be the mindset. I think.
David: Yeah. There’s a really weird analogy, moved, my family just moved
from one apartment to the other after, I don’t know how
many bar move or, uh, like two Oh,
Chieh: Did you use a mover?
David: We Did use a mover. I actually, my first job ever was a mover.
Is So I have like a lot of anxiety from moving in New York City.
Chieh: I thought you’d be like, I don’t need to.
David: No, no. I, I mean I probably don’t need to, but I like, it gives me anxiety, especially 10 years of life. Yeah. And so we moved, but the move took a [00:33:00] really long time
and we were left in our apartment with nothing. Nothing. I mean, I think actually four cups. Four plates, like for nothing for I think like three weeks.
We only had two outfits
Chieh: each.
David: And, and at the end I said, do we even need any of our other stuff that we just moved because we’ve been living just, just fine.
Chieh: I, I couldn’t agree more, I, um, so. Um, I, I feel the same way. So like, every time, you know, you upgrade an
apartment, you’re like, you know, you start to amass all this stuff. Um, so it’s a good analogy, right? It is kind of kind, a similar thing, you know, and I, at the end, I said to my wife, literally, we do not need any of this. 80%, not like 50, probably 80. Why do we have so many cups? Like we, we, we don’t need that many. You know, like, why do we have, and, and it’s the,
David: it’s
unfortunately, it’s a very similar dynamic where you’re like, wow, okay, I can do a lot more with less than I thought.
Chieh: Yeah. Yep. Know? And was she like, well, then we’ll get rid of 99% of your stuff.
Yeah, yeah. Exactly. Now, now
David: if
you saw our closets, you would know that I already have 1% of the stuff. Um, [00:34:00] so, so let’s just talk now the journey of kind of going public, which, um, that was 21, 21, 21, So really the peak of everything. And,
and, uh, yeah. What Was that, did, did you have a dream of being a public company? CEO?
Chieh: I did. I, I um, uh. I thought we have to do, of course, What is best for the company
as a entrepreneur? When I put on my personal hat, you know, um, it’s kind of like that, that’s what I think most entrepreneurs dream of. It’s like I’m a public, I’ve, I’ve made it from the garage to a public company, CEO, of an enduring company that will last for the next hundred years. Um, and when you think about companies that last for a hundred years,
many of them end up being public companies at some point in their life cycle. Um, especially if you’ve raised outside money. Um, and so yeah, it was a, a personal dream of mine, uh, to be that.
David: and how did you do that?
Chieh: So perhaps, uh, um, it was a sign of the times.
Um, we did, we went public via spac. Um, [00:35:00] and so
I think most folks know what a SPAC is, but if you don’t, it’s a, it’s a special purpose acquisition company where they’re already
public and
they basically, uh, merge with a private company and thereby, voila, you have a
new public company.
David: And that the pe the reason people were doing that at that time was ‘ cause it’s faster.
Chieh: Faster. There was guaranteed money, uh, at the time because the SPAC itself has, a certain amount of funds in trust. And then also, they would also help you raise
another round to bolster whatever they had in trust, um, um, uh, at that time. it. Yeah.
David: And so from the time you decided to do that to doing it, how long was that?
Chieh: Way? longer than we way longer. Because when we first started the process, um, it was a very kind of, I guess, uh, um, uh, popular way to go public that was very, very hot. But by the time we had gone, it ended up being way longer of a process, way more [00:36:00] arduous of a process and if we had just filed a regular s one.
Oh my God. Yeah. So, uh, but once you’re halfway through it, there’s no way to. Rip the bandaid off and go right back and and start over again. Um, and
David: so yeah,
Chieh: looking back, we, we, oh, I didn’t know that. There’s probably a mul, a multitude of ways we should have, um, uh, gone public.
David: Whoa.
And then how long were you, you were public for a couple years? Yeah, Yeah, about eight quar, seven something like that. How was it to be a, was it, was it everything
you dreamed of to be a
Chieh: public
company?
CEO? Uh,
David: Uh,
Chieh: I have no, well, good dreams and bad dreams too.
So, you, um, um, in some ways, uh, yes because, uh, I had a very supportive board. Um, the sponsors uh, the original founders and sponsors of the SPAC stayed on the board, so they were very supportive and they were great, uh, uh, individuals.
Um, so in some ways, uh, yes, like it, it was, uh, I had the tools that I needed, um, in other ways. I didn’t have the [00:37:00] tools that I needed. and in some ways it was very market driven. Um. The market acts in sometimes in very rational, but yet sometimes in very irrational ways, uh, especially in the short term. And so once we were put in the penalty Boxed that were just sPACs in general,
new instances in general, that became a very difficult kind uh, dimension to, to navigate.
So already if you think about you being a private company,
you’re probably thinking you’re already playing a hundred dimension chess at the moment, but then to have a daily report card out there,
and now, you know, up rounds and down rounds by the millisecond,
it just creates a whole new dynamic that you have to, that you have to kind
of navigate
And yes, you know what we said on the day we went public is like, don’t watch the ticker.
In the office. We weren’t allowed to have the ticker
up because let’s just focus on the best way to make a great stock and a great, company is to just focus on our jobs.
But at the end of the day, your vendors, your partners, they’re all watching the same ticker, you know? And so they’re [00:38:00] gonna call when things go well or when the things go poorly,
and you can’t control that.
And so that, makes it yet another dimension. on being a CEO.
David: I, I talked to, uh, I talked to A CEO, I’m just trying to remember who it
was. And they were saying how people were just glued to the screen watching the stock price. Yeah. And he said, no, we would do nothing wrong, nothing different.
And
it
Chieh: would
go
David: down, and then people would start freaking out that it went down and ask the cEO, why did it go down? He’s like, I don’t know why it went down.
Chieh: Yeah. I,
I, you know, um, what’s interesting is that
I think once you’ve been,
uh, once you’ve kind of
felt that, um, you know, in the, sorry to take a step back. In the private world,
um, the, the evaluation of a company is set by one lead. It’s one trade, realistically. Um, and so. Everyone’s very worried about up and down rounds. Um, which is fair because as a VC, that’s really how you, you make money and that’s
how you make sure that the, the overall portfolio is, is going well. But once you turn public, it’s [00:39:00] like
up, round, down rounds, literally by the millisecond. I, I mean, it’s just like the ticker,
It’s a ticker, is a ticker. Um, and so someone is trading a stock because someone’s buying because they’re, they think there’s brighter days ahead and someone’s saying, no, I’m gonna sell because I don’t think the days are Um,
and so every millisecond that’s
David: happening
Chieh: with
your company, um, and so it puts it all into perspective, I think, very quickly. Well,
David: you, you’ve, we’ve talked a lot about the investors. You talked about the investors who stayed on. When you think about all the investors who were part of Boxed, is there one or two that really stick out that, like,
we all had a lot of investors, but there’s usually one or two or three that like, really were value add to you?
Oh,
Chieh: for sure, for sure. I I would say not even just two or three.
Um, And i’d say of course there were some that were so amazing at helping us navigate, uh, business challenges.
But there were also some, some advisors as well as investors that were great. Just making sure that the team [00:40:00] was well equipped mentally and from a livelihood perspective to be able to tackle the business challenges that they were not opining on.
David: Um, warranted. I’m curious about that. Yeah.
Chieh: I, I, I think at the end of the day, um, it’s, a, being a CEO of course it’s, it’s
outside in, it’s very glamorous. It’s like you’re the CEO you work for yourself, but the reality
is you don’t, the minute you take outside money, you don’t work for yourself. Like you have a board that you report to and the board actually reports to then probably their LPs as well.
So you’re, you’ve then put yourself in this chain. And so it’s actually quite a lonely job, uh, at the end of the day because you’re making oftentimes very unpopular decisions based upon imperfect information.
Um, and that just creates this kind of vacuum that you have to sit in yourself oftentimes. And then anyone who’s gone through that, who will lend a hand and say, Hey, these are my shared experiences, this is how I’ve navigate similar challenges,
I think it’s really helpful. Um, and it’s helpful even if you don’t [00:41:00] follow their advice, um, to just kind of delete out the, the, the standard deviations up and down, um,
from your daily psyche because, you know, maybe I just think too much about stats of math, but you know, if it’s, if you’re having a day that you’re, two ds above, uh, or two Ds below, uh, um, uh, um, you should probably think twice and you should call that mentor or, or that investor.
David: That’s, yeah. That’s good advice. That ‘ cause is, it’s a lot of like this
oscillating line. Yeah. And sometimes that oscillation in like one day is,
Chieh: you know, exactly a perfect way to, uh, to explain it. That that. That oscillation. It’s,
it’s not even the altitude in which you’re flying, but that, that up and down oscillation.
That’s what can really get you. Um, and I didn’t know that my, throughout our first
company, so the gaming company, I would just ride it. I’d be like, there there would be like
up and down. Yeah. up and
down. 10:00 AM we’re taking over the world. [00:42:00] 11:00 AM Ooh, this is not gonna work. 1:00 PM taking over the world and you just come back so fatigued and exhausted.
Whereas again, you just delete out the tops and the bottoms and you’re just like, doesn’t matter who says what about a company?
Both, both good and bad. You know, if we get a great giant client, guess what? We need to get 10 more. If we, if one of our biggest clients kind of ditches us, it’s okay. Uh, we got, because there’s a pipeline with 10 more. Um, and so just being able to stay focused and just one step at a time, as cliche as that sounds, it really helps you in your kind of
mental state to just say, okay, doesn’t matter, whatever anyone says, whatever happens. I still gotta do the job in this next hour.
David: Mm.
Chieh: Um,
I, I, it was a lesson, a hard lesson that I learned that really helped me kind of withstand 10 years at a consumer company.
David: Mm. Uh, I heard you describe being a CEO at the event that we were at. Um, and I
think you were kind of getting there. Like, I would love if you could share, like, how would you describe this job to someone [00:43:00] hasn’t done it before?
Chieh: Oh, it’s like you’re, um, you’re trying to be, um, as, again, as
cliche as it sounds, you’re trying to be the
GOAT right So you’re trying to be the greatest of all time, but most folks don’t realize the sport in which that
they’re trying to be the goat of is a broken glass eating competition.
So that’s, if you ask any entrepreneur, it’s like no one will ever say amazing. Yeah. Just fun, fun, fun every day. You know, it really is like one challenge after another.
but yet. Next day you wake up, you’re like, oh, more broken glass. Let’s put it in my mouth. Let’s chew it, and let’s put a smile on our face and like, let’s keep marching so that I can be the best at this.
And
so like, unless you really enjoy it, it becomes a really difficult
existence. But I guess that’s what makes some of us kind of just, I guess, different and cut from a different cloth is like,
I’m a fish in water when that happens. you know, I’ve lived kind of [00:44:00] peacetime livelihood as well, and it just didn’t sing to me as much as kind
David: of
Chieh: like
just being in it and, knowing there’s challenges and knowing it’s painful, but just maybe perhaps is what I was put on this earth to, do professionally.
David: Yeah. Yeah. I, I, I think that is, that’s such an accurate description and what my, I, I
I was at this event and it was a small group and we were talking about this and someone said, I was really, it was like a 40 person group, and one of the founders in the group said, how do you deal with burnout? You know, because I’ve been doing this 10 years, he said, and I just don’t know.
In front of everyone. I was, you know, he said, I, I don’t know how to deal with it. You know, like, when did you have that and that, and I think that I would consider myself really good at the glass heating contest. Yeah. But then
at
some point,
you know, at some point it’s, it’s, it’s exhausting, yeah. I Even if you enjoy it, you know,
Chieh: for sure. I, I used, so our first company, um, I couldn’t agree more. And I think when you don’t have the perspective of multiple companies, [00:45:00] I think there’s a stigma out there, or there’s this kind of preconceived notion that entrepreneurs need to work 27 hours a day, 400 days a year. And if you are like
a, a decently wise investor, like you had chip hazard here. Yeah. I think, I think Chip was saying, no, we don’t want that because you’re gonna last six months if you work like that. Um, we need you for the long haul. And actually being able to get some perspective and recharging once in a while actually probably makes you a much better cEO.
Yes.
Um, so our first company. Uh, I remember when we were being acquired, I told, um, the corp dev teams of some of these companies. I’m like, it’s just the speed at which we work. Come to the office. 2:00 AM I’ll give you a copy of the key. You open the door anytime we’re all there working. It was a small team. Um, and that was generally true, but actually the team got pretty burnt out working at that, at that pace.
Um, now you still have to work in a frenetic manner, but there is a fine line between like going to the point of burnout, [00:46:00] um, and, and also kind of like not working hard enough.
Yeah. So you have to really make sure you’re balancing that correctly.
David: Yeah. Yeah. I think my lesson at the later stage of better Cloud was how to go almost burned out, like almost to that dark red.
Yeah.
And then pull
back when it was necessary. Yeah. And then pull back. When it was unnecessary, you know what I mean?
How did you back? Like what were, what were my biggest things? Like I can remember, for example, every fundraise we did post a certain time, I think post series A or every single one. I took a three day weekend with my wife.
As soon as the money was in the company bank account, we took a three day weekend where I was fully disconnected. And it’s not that much, but actually three days of actually being disconnected and my, it also helped me with my wife, so she wasn’t pissed off because I hadn’t been there for three months leading up to that.
So it’s things like that where I, I, we did that every single time that we did around, for example, um, some weekends I would just say to my wife, like,
Chieh: I
David: can’t,
I need
like a day and I would just crawl up on the couch and do nothing for 24 hours. And that’s all I [00:47:00] needed. You know,
Chieh: I, it’s, it, I I’m glad you’re saying this because like it’s different for everyone. Uh, but you, you, didn’t say, I. I I went away for three months. Right. I went away for a weekend.
Right. Wait, what? That’s that’s normal. You know? Uh, and so, um, you know, yeah. Um, so taking a weekend once in a while, again, it just depends on the person. Yeah. Um,
it could be just one day and like, i’m just not, you know, the phone’s gonna be
on the table, like, actually call me if there’s an emergency, but I just need to recharge or actually get some perspective about what we’re up to.
Um, and I think that could be powerful and it’s different for everyone. You know, some folks it just might be, I don’t know, I just wanna go for a, a long drive somewhere. Right. Um, some folks I want a weekend off, Some folks I just want an evening where i’m with my friends Right. And I don’t talk about work.
Right. Um, it’s just different. And I think, uh, every entrepreneur just needs
to know that that’s normal. Um, and then you have to modulate.
There are times when you should be working 27 hours. But there are
times when did, like, company’s not gonna fall apart if you take the night off and go out with your [00:48:00] friends and watch the game or, or, or of just have a nice dinner with each other. And then, you know, in the morning, like.
David: Everything’s gonna still be there, Everything’s gonna be there most likely. You
know, and so, yeah, i, I think sometimes in your first company, you don’t have that perspective.
Yeah. Um, what, what has been the greatest, a lot of challenges, uh, glass heating Contest. What has been the greatest challenge you faced at Boxed, and how did you overcome that if you did?
Chieh: The greatest challenge, um, was being a public company. And I don’t think we, like, I, I don’t think I passed that challenge based upon what we, what we, what, what the scorecard says. Um, so meaning that, yes, like we became a public company and actually in 2022, we were one of the best traded public debuts of the class of 21.
But in the end Boxed didn’t turn out in a great place. Um, the market didn’t like emissions. Interest rates were rising, we were unprofitable, um, uh, went public via spac, uh, smallish cap, like our [00:49:00] peak market cap was one point x billion.
So it’s still re relatively small when you’re in that kind of world of public companies. So I don’t think, I, i, um, I don’t think, I think, I don’t think i, I kind of won the super bowl.
Uh, I feel like in some ways going and ringing the opening bell at the new York Stock Exchange or the nasdaq, it’s like, yes, that’s your ticket to enter the Super Bowl, but I don’t feel good that I I got blown out.
And so, yes, there’s a certain amount of pride and like, yeah, not a lot of people playing the Super but again, like doesn’t feel good if it’s 42 to zero at the end. Um, and there’s no prizes handed out for that. So I think now that i’m equipped with the hard lessons,
of having early stage company that sold of having a company that went public, of, you know, of, of seeing all that scale from small to large, um, and the ups and downs over the last 15 years, I do think I’m better equipped to make it back there and be better and actually
have
a better result.
So. Mm. Um, but yeah, I can’t sit here and say like. I [00:50:00] passed with flying colors. The biggest challenge of my professional career.
David: How was that la The end of Boxed that must have been, um, ‘
Chieh: cause sounds like, from what I understand, like a pretty finite end.
Oh yeah. Yeah. So at the end of Boxed our software business that was, um, uh, quite profitable ended up, um, uh, in the hands of, um, uh, of, of, of BlackRock.
Um, who it was, we had a, so sorry. it, we were, we started off as a consumer company. Then actually we sold more and more people, A lot of people don’t know this, but we actually were servicing every airport in America. Um, so if you’ve been on a if you were on a flight through some of those years, there’s a high chance that like you are a Boxed
customer and you just didn’t know it. Um, and then also, um,
going on, we actually began to sell the software that powered all the technology uh, that was Boxed. Um, and so that was packaged up, the software part was packaged up into a separate company. that, Um, uh, that was acquired. [00:51:00] Uh, the e-commerce
business, unfortunately shut down and was, uh, was bought for pennies on the dollar. Uh, but you can still order it from an Yeah. Um, you can still be a customer.
David: Um, so you, you, what I see on your linkedIn and from the conversation we’ve had, you’re you’re gonna do this again yeah, Looks like. exactly.
So you can’t, you’re back at it after all that pain I just talked about, like, can’t wait to do it again. How long, that’s what, how long between stepping
away
from Boxed
and making the decision you were gonna do something again? Was it in, like, did you know like, i’m gonna, I’m definitely doing something.
Chieh: Oh, I, uh, it was a millisecond, like, meaning that I remember what I told our team, um, that if this doesn’t work, like we, this is one of those times where we’re gonna work 27 hours a day and do everything possible, um, uh, in order to make sure that.
We, we can get back to becoming a, a, you know, a a good company again in, in the public markets. [00:52:00] And if it doesn’t work out, then it won’t be because we
didn’t do everything we humanly could have, uh, in order to, to make it a good result.
Um, and I think that mentally was good for everyone because we worked so hard and we, there was no stern stone left unturned, uh, um, um, at the end
of Boxed. Um, and so when the board said, okay, we just gotta call it, this is, you know,
it is, it is what it is at this point. Um, I remember telling the board member, well, he, he asked me like, what are you gonna do next? And I’m like, I mean, I’m starting a company like tomorrow. Like, i’m going filing paperwork.
I’m gonna start a new company. And he, he said, I will, you know, i’ll be here for you for the rest of your life. Um, I have that much kind of
respect for what you’ve done. Um, but if you do that. If you don’t at least take the summer off, uh, or even a month off, he’s like, he actually said,
I will never pick up [00:53:00] your phone call. I will never invest in anything you do. I won’t even
pick up your phone call. Um, and at the time, again, sometimes advice and shared experiences at the time seemed so counterintuitive.
But looking back, it’s what I needed. So, uh, i, I ended up going on a, I took a, a sabbatical for, um, uh, about three months. Um, which, you know, some people out there will say that’s not a sabbatical. That’s just some Time off. Um, but three months felt like an eternity. And then actually, um, I ended up, uh, uh, working at the World Economic Forum for a few years after that. So now you’d have
to say
about two years. Plus i, i’ve been, uh, uh, kind of out of early stage,
David: but But um, but you come back. Yeah. You know, when we’re talking
about weekends off yeah. Think about what two years off does for you. I feel like,
Chieh: yeah. I got a wealth of knowledge to deploy again, so i, I feel good about it.
Yeah. Um, do you have any general sense of what, is it gonna be a consumer company? Uh, no. It will not be a consumer company,
not a knock to any consumer founders [00:54:00] out there.
It’s, you know, alluring, um, uh, it’ll be the enterprise. Okay. Um, and the themes that, you know, I’ve been trying to discover is that when you look at
kind of history and technological innovation throughout history, no matter small or large, um, if you focus on actually the large ones, but this applies for even small ones.
There’s massive job destruction, um, uh, in certain categories, but there’s actually job creation as well. So how do you kind of,
how do you make sure that folks are transitioning well into that and the economies that. You’re dealing with, um, uh, are transitioning their kind of citizenship? Well, um, perhaps it’s a bit of kind of my last job at, at, at an nGO that kind of has inspired this. But, um, entire companies, entire countries need to navigate how AI will change work in their, in their countries, uh, and in
their
David: And
Chieh: so, um, how do we make sure that we create a company that can help folks do that?
That’s kind of, uh, very cool. That’s a theme
that I want to investigate.
David: Very [00:55:00] cool. Um, so let’s transition to your background a little bit. So, did you always know you wanted to be an entrepreneur?
Chieh: i, I was always interested in building businesses. Um, ‘ cause I remember, i, I was like, I used to sell candy at the, I used to play a lot of basketball when I was younger. I used to. And I just realized, oh man, like, like Can, like people are on the courts
they like,
there’s
kids with a few dollars in their pockets, like. Like and Yeah, they want can, they don’t have to go all the way to the convenience store to get it. And so I brought it to them and uh, and yeah, that was my first, I guess
David: entrepreneur at, at what age?
Chieh: was Definitely sixth grade maybe before Yeah. I kind of caught that bug bug early. Um, but then, you know, maybe it was that, um, uh, because of family pressure, I went for more, stayed down the middle kind of career. So I was an english teacher first, and then I was an attorney after that. Um, and then I think at some point, wow. Yeah. When you’re at a big law [00:56:00] firm and I, I, I loved my law firm. Like they, they treated me quite well. But when you’re, it’s like 3:00 AM and you hadn’t gone home in two yays and you’re like staring at documents like it will. It will make you think about what else you enjoy in life. Uh, and so I fell back to entrepreneurship and said, okay, this iPhone thing came out. Let’s, let’s build. Games for it.
Yeah. You went from the law firm to the gaming yeah. Yeah. I, it was and in, oh my God, in 2010 too, in the middle of the great recession. So I remember the, my, all of my colleagues thought a hundred percent che got the boot. Yeah. Because no one was
quitting their jobs at the time.
People were hanging on by their fingernails. And so I was like, oh, I, i, I was the first person in my class to voluntarily leave. Um, and so I remember people were like, sure, you know, and what are you doing next? I was like, oh,
I’m gonna join, uh, uh, this video game company that my
friends.
Are doing. And They’re like, what?
Like
David: what did your parents think?
Oh my [00:57:00] gosh. Um, where are your parents from?
Chieh: Uh, so my parents are are from Taiwan. Um. But background is a bit of mix of Taiwan
and Japan. And so a bit of everything like, um, but um, they were, they’re, they’re first generation, so, uh, they, it, I think they were so, I wouldn’t even say angry or disappointed. They were just so perplexed.
You know, it’s like my mom for the first, not for the first time, but she wasn’t even angry. She didn’t yell at me. She just said like, she doesn’t understand the decision. Like, most folks work their whole lives to become an attorney or a doctor or something. And now you’re starting out, you’re, you’re just gonna throw away the years that you like, and to, to what make video games. Like
what? But I’m like, yeah, we’re gonna do it. And I guess again, that probably makes us
uh, quite exactly, uh, quite strange. But, uh, but it seemed natural.
David: Um, what, did you have a role model or a me, let’s say a mentor. [00:58:00] Kind of in those, making that transition is a pretty big kind of transition. Did you have someone in those years or did you have someone at Boxed, like one person that kind of was mentor to you?
Chieh: yeah, yeah, for sure. Um, i’d say role model. Um, uh, definitely several just from um, kind of like, um, uh, in like, for example, an Asian American that had made it, uh, like at that time Jerry Yang. And so, And so really kind of eventually
being able to meet him and actually having him as an investor.
That was
an awesome whoa. thing, You know, just to be able to meet him
David: in the gaming company?
Chieh: Uh, in the, no, in, in Boxed. Yeah. Wow. Uh, and that’s Yeah. -And um, but then as a true mentor, uh, there were a few, but actually I would say one of the folks that really helped us, uh, just a few country bumpkins from new jersey really get into the startup game, um, was our attorney of all folks.
So, um, uh, He was in Silicon [00:59:00] Valley. Um, uh, he’s not an attorney anymore. Uh, he’s actually, a, I think a coach. He’s an investor and coach.
So we had a, um, uh, ted wang as our attorney. Um, he was kind of facebook’s attorney at the time, twitter’s first attorney square. So he was like that person.
And I was so naive that I just cold called him like, you know, like, I was just like, and left a voicemail. Yeah. And, called. ‘ Cause we were interviewing lawyers at the time, and I remember my first question to him was like, you know, Ted, um, and being from a law firm, like everyone’s trying to get business, but I didn’t realize that, like, when you’re in that realm, like you pick your clients and once you get a certain realm, it’s like, I don’t, I I represent who I want. Yeah. Like, And so, you know, being this naive kind of guy from New jersey, I was like, Ted, tell me why you should be our attorney.
And he was like, and I I will never forget this. He said, um. He took a deep breath and said, you could just tell [01:00:00] he was restraining himself. Like, kind of like, how did you get this number?
Like, what, well who are you? And like, but he’s like, he actually said, I don’t think you know how this works. He’s like, I pick who I wanna represent. I don’t know you, and where are you from again? Like, and how, like, and so it didn’t end well.
The first call I remember after hanging up, I turned to one of uh, uh, kind of, uh, the folks on our, our cOO who was also with me at the law firm. Yeah.
And I was like, dude, I just had the worst conversation with the biggest asshole ever. Like, clearly like that we’re not using that guy. But to Ted’s credit, he called us, he called me back a few hours later. He was like, you know what? He’s like, I kind of like how naive you are. Like, I kind of like how it’s an open blank canvas. And I think, and he said, I think gaming is gonna get hotter and hotter and mobile gaming. So I think the company has legs and I think I can help you guys. Uh, and I was like, at that time I kind of thought like, I don’t want you to help so [01:01:00] mean dude. Um, but actually I was like, you know, let’s, it seems like he can really teach us.
Um, and we went for it. And he did. He helped us navigate our rounds of funding. He helped us, uh, navigate our our first ever acquisition of the company. And then years later, he
really helped even when I was like, should I stay? Should I leave? Which I yeah. was more like a business and, life cons than he was our attorney.
David: Wow. That’s a good, yeah, that’s a good one.
Yeah. Um, what, what is it that really drives you? You know, we, we’ve talked a lot about entrepreneurship, how hard it
is,
but like,
deep, deep, deep down at your core, what drives you to keep going, to keep building, to try to be a public company? CEO. Like what does that drive, where does that come from?
Chieh: Um, I think it morphs over time, right? Because you’re not born with a chip on your shoulder. Uh, but after having kind of the ups and downs of entrepreneurship.
A big part of my drive is having a chip on the shoulder. It’s like going to the super bowl, getting blown out. It’s like, i, i, i’m, i’m going back there,
you know, [01:02:00] like, whatever I do next, we’re going back there.
Um, and that’s a big part of my drive. Um, but then the exact idea and the exact, like how you get back there with the company, I think
David: it
Chieh: needs to be deeper
than just a chip on your shoulder.
And so really grafting myself onto things that have been personally important to me, i, I think will be important for this next company as well.
David: Hmm. Okay. Last question for you. Um, knowing everything you know today, all the experiences that you’ve had, if you could go back and give yourself one piece of advice at the very beginning
of your whole career, what would that one piece of advice be?
Ho in the early, in the,
like before you start as a lawyer, you know,
like remember I was a teacher. that. back those Um, before you start as a teacher. Oh my gosh.
Chieh: Like Make that seatbelt tight as hell. It’s about to be a ride. Um, i, I’d say be yourself and don’t have regrets. Um, because even [01:03:00] if things don’t work out in the end, if you did everything you possibly could and you were authentic,
like to yourself, uh, um, I think, I think you’ll end up probably realizing it was a,
a life well lived. It’s like I was myself. This is what, you know, god and the heavens have given me in terms of my abilities. Um,
and I did
everything I could
to make the most of it. I really don’t regret many things of anything in life in terms of how I try to take advantage of that.
David: Be yourself. The be yourself is a really, I I, that one resonates me a
lot. That I think a lot of, I find a lot of first time cEOs, founders. Yeah. They have, they don’t, they’re not themselves. Actually,
Chieh: this is how, remember we, we bonded Because it’s like
you meet a lot of, especially exactly. First time entrepreneurs at these cocktail hours or how’s it going? They’re like good, good, good, good, So good. Gooder than good. I can’t imagine anything being bad.
[01:04:00] you know? And just like, alright, uh, i’m gonna get a refill. I’m going back to this conversation because,
know, just we’re, we’re all going through the ups and downs of being an entrepreneur and it.
David: Even the multi-time. That. I think that’s the most important thing that, that’s what I’ve learned from these interviews is that for me, i, when you’re in it, even if you’ve done it a couple times, you feel like only my company is struggling.
Everyone else is doing great. Oh, and then when you, when I’ve been doing these, it doesn’t matter. It literally doesn’t matter. I’ve met people who got to two employees and then shut down, and i’ve met people who’ve built $5 billion public companies, you know,
like the whole spectrum. And every person has these issues. Every person has these challenges, every person. And, and I think being yourself, not just with other
entrepreneurs, but with your own team, with your family, with, I think that it makes it, it makes it easier actually. If not, it makes it really
difficult.
Chieh: Yeah. Yep. I, I, um, um, it makes it less tedious as well. Like mentally taxing
when you just have to like, put up this facade or it is [01:05:00] just
like, it’s just the business doesn’t get better just because you’re telling everyone
that it’s perfect. You know, it’s like you still gotta fix these problems. and actually if you kind. Of, not op not like to the whole world, but for to folks that you trust, and especially in kind of the realm of other entrepreneurs, the reality is probably they might be going through the same challenges. And if you share some of those challenges, like they might have solutions
or
you might jointly come up with solutions or actually might just feel better, you know, knowing that, to your point, we’re all going through this together.
Um, and so yeah. I, I remember we we had
a
good line. yeah, yeah, yeah.
I’m sure you’ve, you’ve, yeah, you’ve been the same.
And I’m sure, you know, people listening to this or watching this have, have also been the
same. You’re like Exactly. Man, That person’s life is perfect. Exactly. Exactly. Wow. How do i, you know, just like, mm. Um, but uh, but yeah, I think so again, going back to your original yeah. Yeah,
David: That’s probably
what I
would
Chieh: tell myself
I love be authentic and no regrets.
David: I love it. Um, cha, thank you so much for doing this. I, I did not disappoint. I really enjoyed this conversation.
Chieh: It’s fun. It’s fun. Cathartic for me. Yeah. Too, [01:06:00] know.
David: Thank you. And for everyone listening, I hope you enjoyed this
episode. If you did, please share it out your networks and we’ll see you for the next episode of not another co podcast.
