Don’t let the words “basketball, “football,” or “League of Legends Championship series” fool you—Sleeper is much more than a fantasy sports and messenger app. One of the fastest organically growing, pro-backed, and fan-favorite platforms, the Sleeper app is the literal product of lifelong friendships between Nan Wang and his co-founders, inspired by decades of check-ins, life updates, and casual catch-ups over friendly games of fantasy sports.
In this interview, Nan Wang talks about how sports helped him find community and a sense of belonging throughout his life, and what it’s like to run a business with his childhood best friend. He also shares his early fears and doubts after pivoting from a stable and successful international career in private equity to launch a startup stateside, and talks about his eternal gratitude towards the Asian community and the “giants” before him who have encouraged and supported him every step of the way—tying it all to how we can all pay that abundance forward.
Warning: This interview is full of heartfelt and wholesome stories that showcase Nan’s deep love for his community and how he has built a platform around those inspiring connections.
Play on the Sleeper app and join its community here!
On fateful immigrant journeys and kismet on the tetherball court
I was born in a rural, small village about six hours outside of Chengdu in the southwest of China. I grew up there primarily with my mom and my grandma. My dad was one of the first students studying abroad in the U.S. after the borders opened up following Nixon’s Ping Pong Diplomacy visit and wasn’t around for the first part of my childhood. He came to the United States for grad school, and my mom and I stayed behind until I was old enough to go to kindergarten.
At the age of five, my mom and I joined my dad at a small town in eastern Washington called Pullman, where he was attending grad school. That was actually where I met one of my co-founders and CTO, Weixi Yen, who had a very similar journey—his parents were also first generation students who came here to try to better their lives. Weixi became my very first friend here in the United States.
As first-generation immigrants, we didn’t initially speak English so we had to make friends through shared interests. We would go out into the student union and play tetherball or kick a soccer ball around with the other kids in the neighborhoods, and that’s how we made our first group of friends. Roll forward to now, it’s been 33 years since I’ve met him, and that friendship has actually continued to stay alive through sports. Our other two co-founders, Ken and Henry, also had similar experiences growing up. This shared experience is the foundation for why we built our company, Sleeper, and why our mission is focused so intently on fostering friendships built through sports.
On the origin of Sleeper, an app founded in friendship forged through love of sports
My family and I moved away from Pullman, Washington in third grade. If you think about how many friends you’ve known since third grade, it’s probably not too many, right? Most people drift apart over time. However, for Weixi and me, we used sports as a way to reconnect every single year and keep that friendship alive for over 30 years.
In the beginning, Weixi used to send me basketball and football cards on my birthday through snail mail. And then—I’m dating myself a little bit here—but we had an AOL Instant Messenger chat room back in the day where we would send each other sports news articles in the early days of the internet. We’d even send videos sometimes—although the videos would take 10 to 15 minutes to upload and eat up a lot of bandwidth through our dial-up Internet on our 56k modem. These were the conversations and interactions that helped us stay in touch.
Weixi ended up at Berkeley for college, and I went to Dartmouth. During our freshman year, Weixi started a fantasy basketball league with his dorm-mates and invited me to join his league. I’d never played fantasy basketball before but I joined because it was yet another way for us to hang out. 20 years later, that fantasy league is still around and all of our friends still stay in touch. We’ve used that as a way to check in on each other’s families every year and see how we’re doing. It has become an annual tradition used to reactivate our friendship and serves as a convenient excuse to hang out.
Sports has played a pivotal role in our friendship over the years so for us, we made Sleeper’s mission to strengthen friendships through sports. Our products aim to build the social fabric that we believe every single sports fan ultimately craves and desires—not just die-hard sports fans but also people who want to use sports as a way to stay close and have conversations with their colleagues at work; to be able to share memories with their grandparents; to be able to smack talk and have competition through games with family members; even as a way to stay in touch with high school and college classmates.
That want for continued connection turned into Sleeper. It’s a social sports app where everything you do is about the friend experience. As a result, it’s built as a messenger. The product looks and behaves like Slack or Discord, where the core components of it are a conversation. It has the text, video, voice, GIF, and meme chat features that you would experience on any messenger you would use, but it’s overlaid with content and games specific to sports, including esports, which allows people to hang out and really have a good time with the people they care about.
On starting a business with a friend
I think this applies not just to business partnerships formed with best friends—it also applies to business partnerships with significant others or family members—but it could go one of two ways: either it makes you or breaks you.
Going into business together either strengthens your friendship or relationship, or it tears you completely apart. Every relationship is different, but you need to go into whatever business endeavor knowing that unless you work at it like any relationship, both outcomes are real possibilities.
When we started Sleeper, our founder group had a very frank and honest conversation early on, and we said, “Hey, we’re about to go into this journey as friends, and we want to make sure that one of our KPIs is that we come out of this journey—whether we succeed or fail—as stronger friends.” That was important to us. What that means is that every single decision we make, we always trust each other’s intent. We always try to work at building true partnership and true camaraderie as we build our business.
On how that friendship-forging mission translates into work culture at Sleeper
A lot of that sense of mutual support has permeated across the rest of our team. That’s kind of how we screen and hire, primarily for culture fit. We hire smart people and trust their intent. We also genuinely love the people we work with.
One of the things we’ve done differently from other sports companies is that we didn’t actually go out and actively try to find sports fans to join our team. We valued diversity of thought and experiences. In fact, most people on our team have never played fantasy sports or they don’t care about sports. It’s not part of their daily habit. What you give up initially in a little bit of subject-matter expertise, you more than make up in many other ways. The reality is that smart people learn quickly, and sports are pretty easy to pick up.
The benefits of how we have built the team have been amazing and numerous because now, you have a group of talented people who come into work and who don’t necessarily tie themselves to a singular product or have a linear path or destination. They are more adaptable because they joined our company for a variety of different reasons, including, but not limited to, the company’s mission, our culture, a career experience they are hoping to get, or the team they are working with. All of this is extremely important because during a startup, you can pivot many times. If people are tied to an industry or product, that’s shaky grounds to tie yourselves to because things could change on a dime.
Tangibly, we see it in our team. People genuinely like each other, and they’re friends. They come into work because it’s fun to work with each other. People get together and go hiking together. Pre-pandemic, we’d all go out to lunches and dinners together, and on Fridays, a lot of them are actually esports fans, so we had set up a LAN center at our office where they would play League of Legends and hang out. A month ago last month, we did a company offsite where everybody got together in Hawaii and spent a couple of days just hanging out.
Hiring outside of a niche or specialized field creates a culture and atmosphere where it’s about the people and the journey; it’s about learning and support, which is translated into a really stable team.
One of my favorite philosophies for hiring and building great teams. pic.twitter.com/bOUxsNhdjZ— Nan Wang (@SleeperNan) September 23, 2021
On startup life—from changing industries to building new networks
The very first step of an entrepreneurial journey is often the hardest to take. It oftentimes means sacrificing the creature comforts and security you have become used to, to venture into the unknown. For me, it was giving up a prior job doing finance in Asia to move to San Francisco, a city I had never lived in.
I was an interloper in a brand new market, and as the CEO and co-founder of the business, my job was to go raise money and tell our story. We struggled quite a bit out of the gate since I didn’t have a pre-existing network or experience to rely on. It’s tough when you’re trying to build a network from scratch and trying to raise money from venture capitalists but you don’t even know who to talk to or where to get an intro.
Not once in the first couple of years of running into walls and getting “No” after “No” to fundraising did I ever feel that I was alone. My co-founders kept coaching and supporting me. Weixi, Ken, and Henry would all say, “We’ll figure it out. We’ll raise this. We’ll get more traction on the product. We’ll eventually figure it out,” and slowly but surely, our network grew. I met friends who introduced me to VCs who introduced me to other VCs. Eventually, our network grew, and we were able to get in front of some of the most prominent VCs in the Valley. Now, seven years later, we are fortunate to have the support of some of the best investors in the world.
It started with one person’s support that trickled into two people’s belief in that future, and then eventually snowballed into a group of people’s faith in our work ethic, which allowed us to get through those early days.
On entrepreneurial fear of taking risk, raising funds, and burning bridges
I remember having a conversation with Weixi while walking across China Basin in San Francisco about two years into starting Sleeper. We were stalling on fundraising. I was having business development conversations and early traction on the product, but none of the stuff I was doing was effective, or it was only marginally effective. We were almost running out of cash. I was telling him how I kept feeling anxiety two years into our business because I felt like I was on a life raft that was drifting further and further away from shore, and that fear was really scary.
The analogy I was trying to make was that the shore was everything I knew. It was how to do financial modeling and networks in finance. If things didn’t work out, I could go back into private equity, banking, or consulting. It was all that I had built up from a network and education perspective to be employable.
Every year that our company was not successful felt like the life raft was getting further and further away, and it was harder to swim back to shore. There was no more safety. Say the first year you’re doing your start up, if it doesn’t work, cool. Fold it. If you’re six months in, go find another job and say you were on garden leave, but two years in and you’re still not successful? You’re a failure. And that was the fear that I had.
I talked to him about it, and I said, “I don’t know if you go through this conflict” And he said, “No, I don’t go through this. I’m an engineer, and I’m still engineering. If things don’t work out, Google, Facebook, Amazon, or Microsoft would hire me. I understand why you feel that way now, and I understand why you’ve had so much anxiety about not being able to deliver on fundraising and business development and so on.”
He looked me in the eye, and he said, “How about this? Let me teach you how to code. Let me teach you how to design. Let’s do this to the full extent of our capabilities, and I promise you: if this doesn’t work out, wherever I go, I’ll make sure that you come as a package. I’ll hire you and I’ll train you so that you’ll always be able to get a job, even here in the Bay Area.”
That changed my entire perception.
Just hearing that gave me the confidence to run, not walk. Early on, I felt like I was pulling my punches because I was afraid of burning bridges. I didn’t hit up every single VC or contact whom I could have because I kept thinking, “Oh, what if it doesn’t work out?” Actually, that way of thinking hurts the company. Building anything, you’ve got to go full throttle. If you don’t, somebody else will, especially in the startup world. That was another trigger that fundamentally changed the trajectory of our business, because then, I just stopped looking back at the shore and started paddling. And just paddling, we accelerated our fundraising; we accelerated our business development. That conversation really supercharged me and a lot of the business side of our startup.
1/4: @sleeperHQ is a company founded to strengthen friendships through sports. Thankful to @a16z and our other incredible investors (we appreciate you all) for supporting this mission. https://t.co/hl8BLf6PH3— Nan Wang (@SleeperNan) September 16, 2021
On sharing abundance and the Asian founder community in Silicon Valley
The Asian community in Silicon Valley is incredible. The founder community there is amazing. It is so strong and so supportive. That is what actually helped catapult us into these conversations. There are many people who are part of the Asian Hustle Network community who have been instrumental parts of our journey.
When I moved back initially to SF, I didn’t know a lot of people. However, one of my very good friends whom I had met while working in Asia, Jason, was a venture capitalist in the Bay Area. He started introducing me to everybody, and he’s the ultimate connector, so one conversation led to another and before I knew it, I met Kevin Lin, co-founder of Twitch. And then I met Tim Chen, founder of NerdWallet. I met Dave Lu, founder of Fanpop and Pared. Then through that network, I met their friends, and one became ten; ten became 100; and my network continued to compound from there.
When you look at it, we all share very similar journeys, and it goes back to: hey, we’re first generation. We’re building on our parents’ legacy. We’re succeeding. Now, let’s build community. And that community? Let’s share that—share that abundance with others.
The Asian founder community in the Bay Area is selfless. It’s impactful and powerful now because a lot of these Asian founders are doing some really big things—the Doordash, Zoom, Twitch, Patreon, NerdWallet, and Honeys of the world. These folks are now really supercharging it to the next level. That community is grounded in this ethos that it’s not “I,” it’s “us,” which is really powerful.
On the strength of community and the Asian American diaspora—first generation and beyond
I’m very fortunate to come from a family of first generation immigrants. They’ve taught me what it means to work hard and to hustle. They’ve valued education growing up, and they’ve always invested in me as their son and only child to really pursue the American dream.
There is a huge delta between where I am today and where my family came from.. My parents were born into a small rural village where even getting a basic education wasn’t guaranteed. Their family members and fellow villagers literally starved to death during the famine caused by the Great Leap Forward and Cultural Revolution.
To reflect on that as the starting point, to where I am standing today—I’m fortunate because I’m standing on the shoulders of giants. I am grateful for my parents, as I am sure many other “hustlers” are grateful for their parents, who sacrificed for us so we didn’t have to struggle nearly as much. The roads I have walked on all of my life have been paved.
I imagine a lot of the folks in the Asian Hustle Network community also share similar stories. I follow the Facebook Group, and we’ve got members whose parents literally were refugees during the war in Cambodia or Vietnam. Folks who got dropped into cities and countries completely foreign to them where they had to build a life without being able to even communicate. Those are real struggles. For us, we’re lucky to be able to have those foundational building blocks to continue to build our story and to amplify our impact. Seeing our generation give back and create community through the Asian Hustle Network and similar organizations—seeing the impact that we have on combating Asian hate through work like #HATEISAVIRUS and #StopAsianHate—is really empowering because it means that we’re not idle and we’re not sitting on the laurels of what our parents have done. We’re progressing and moving forward as a community.
It’s going to be even more important now than ever because we all come from different parts of Asia. If you’re not careful about strengthening ties, then it becomes easier for people to divide us. You see that in certain communities, and you see that in certain groups. I think every culture and heritage should be celebrated independently. Don’t let people divide us. Seeing everybody come together in groups like Asian Hustle Network for me is really refreshing because it means that there’s hope for us to really join forces and be a large part of the culture here, despite the fact that we may be immigrants, whether first or second or other generations.