Awaken* newsletter

March 14, 2024

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On December 11th, I had the honor to chat with Siqi Chen. Siqi is a legendary figure in the startup space. He has led product at Zynga and growth at Postmates, served as CEO at SandboxVR, and is a 3x founder with two exits. Siqi currently works as the founder and CEO of Runway: a company which develops tools to allow businesses to painlessly model their finances. We had a great conversation which touched on topics such as high/low agency, PMF, insecurity. I thought this conversation was especially fruitful. Without further ado:

DEVELOPING AGENCY

I started out the conversation by asking Siqi if he felt he was always a high agency person, and it seemed so, he said:

Looking back, there were memorable things from my childhood that suggest that I probably did. For instance, when I was three or four, I would ride my tricycle in the yard. When my grandparents closed the gate, I would turn the tricycle around and ride it through the vegetable patch to get to the other side. That seems pretty emblematic of how I turned out. But it’s hard to tell when you’re young… One of the more profound impacts on how I turned out is–my dad is a physicist and he gave me a book by Richard Feynman when I was in the 6th grade. It’s called “Surely You’re Joking, Mr. Feynman”. That had a huge impact on my development. I recommend that book to everyone. He was a very iconic, first principles thinker, didn’t care what other people think. 

I followed up by asking how people like me can work on developing more agency. The short answer is self-awareness, but here’s the complete answer:

In my interactions with people, I think there are feedback loops that can become very productive or very negative, depending on where it starts. And I think maybe where it all starts is self-awareness. Like, what are the feedback loops that are feeding you right now? Where people become low agency, is when they ascribe blame or responsibility to people, to things outside of them. And it’s not even wrong, right? Like, we’re all affected by things outside of our control. But when everything that happens, you assign blame to something outside of you. Then you’re right, and it’s confirmatory. Next time it happens, you’re going to do it again and you increasingly get into this loop where you have less and less agency. And the converse is also true, right? If everything that happens, I could have done something about that. Increasingly, you become more capable and you have more agency. So I think it’s like identifying which feedback loop you want, and understanding what feedback loop you’re in now is probably the way to do it. 

I agreed with Siqi and added that I thought that the positive feedback loop was the more meaningful, but difficult way to live life–surprisingly, Siqi had a different opinion, explaining that a low-agency life is actually more difficult because you end up at the whim of other people, living a life you don’t want to live.

PRODUCT MARKET FIT

Naturally, as the master of all things growth, I had to ask Siqi about PMF. I started by asking him how he defined PMF:

One way I think about it is that product market fit is something that you want to always constantly be chasing. You can have perfect product market fit with the market that you have, but in order to grow you need to extend to new markets and increase the capabilities of it. There’s always going to be a customer in that new segment that is unsatisfied with your product and it’s going to feel bad.

I think it is a continuum that you chase, but there is also another part of my mental model about product market fit. I don’t think it’s a line. I think it’s actually a 2D grid. 

When I think about starting a new startup, there is like, are you even on the path to increasing product market fit? Initially, you’re just like searching in the wilderness for something. You don’t necessarily know what is the right target customer. You don’t know what the right solution is. There’s a bunch of unknowns. As you talk to more customers and you build more things, you can see further out into this forest, you can maybe see the exit from the forest, and that’s when you start getting on the tracks. 

So I think it’s very much a 2D grid, and so you want to first get on the track. To make sure that you understand what you’re doing. You have a pretty good understanding of what your ideal customer profile is, and you’re going to build towards it. Then it becomes like, okay, how many of the market can I actually service? Today is it 10, 100, a thousand? And can I expand to different segments?

Siqi also mentioned another framework he used for PMF which to me seemed retention focused:

One framework I do have is this idea of a boat. The problem with the boat is if you don’t have product market fit. The best boat will sink if there’s a hole in it. You can try to compensate by having a nicer boat, a bigger boat, or a faster boat, but if there’s a hole, you won’t be able to see it unless you focus on it. In terms of metrics, that’s retention. You could be really good at growth hacking and have a million people come in, but if they’re not sticking around, you probably do not have product-market fit.

I also brought up an article I had read recently, The Tyranny of the Marginal User, which is a great article that I recommend our readers read. Essentially, the main idea of the article is that modern apps are catering to the marginal user, the next user they’re going to get. By adding features or tuning our apps or products to reach the widest audience, the product can be degraded, especially for existing consumers. I had Siqi give his thoughts on this:

Andrew Chen referred to this as the next feature fallacy ten years ago. The next feature is the thing that’s going to get you there. What you’re describing is a version of that at scale, where you can only do the next feature because you have so many users. I think the framework that I have about this is that products are path dependent. If you start with a certain audience and a certain user base, they will lead you towards the shape of a certain product. Their asks and their problems are going to be a certain shape. That might not at all intersect with some other segment that you would find really valuable. 

If you’re building a product for a brand new startup with ten to 20 people, there’s a lot of these companies out there. It’s a pretty big market. There’s nothing wrong with that. You’re going to be building new products, but the things that they ask for a lot of the time, if not most of the time, are going to be very different from the things that an enterprise customer will ask for. If you actually want to get the enterprise with any level of latency, sooner rather than later, you have to go directly attack them. You can’t just next feature your way from there to here. You have to figure out, okay, I can focus on this product, but there is some other segment, another value we’re probably going to solve, and I’m going have to treat that almost independently of the product that I have.

I asked Siqi if he had run into this problem with Runway:

It’s a lesson I took for Runway. Initially, the thinking was, we’re going to build something for startups and just for startups. Like, companies of a certain size and we’ll grow with them. We built a product focused on reporting and Runway. It helps you understand your spend because you’re a brand new startup. What do you care about? You just care about burn. You’re not a very sophisticated business. What we quickly found is that we solved that problem.

It’s not that valuable a problem, as it turns out. Once you’re a startup, you learn that Runway tells you very succinctly, that you spend all your money on people this month and next month doesn’t change, right? Meanwhile, you have these larger companies who are making multimillion-dollar decisions, and they need some kind of modeling planning tool. These use cases are so far apart. We could have gotten a million startups, but they wouldn’t have had the pain and the detail of this problem. So we kind of threw it away after a year and focused on the SMB use case or 50,000 employees and you’re on excel, and there’s a lot of complexity. The product, as a result, looks completely different. If we kept on chasing more of those startups, the product would have looked completely different and would never have gotten us to where we are today.

I asked Siqi if they still offered the original product, turns out they’ve sunsetted it to focus their limited resources on building tools for SMBs, but they are planning to eventually go back and serve the very early startup market.

BEING ASIAN AND INSECURITIES

As Asian Hustle Network, I was obligated to ask Siqi how he felt being Asian qualified his experience as a founder–his answer was similar to Webflow cofounder Bryant Chou’s:

I try to avoid it as much as I can. Not because I’m not proud of being Asian. I think there’s plenty to be proud of. It’s generally seen as one of the model minorities. But I do think about it sometimes. I think about conflict avoidance. Or I can be introverted. And I noticed that it will surprise people who don’t know me, but I’m an INTP. I’m super introverted. And I tend to be kind of conflict avoidant. And I do wonder, when I look at people who are more outgoing and into football, would my career would have turned out better if I liked “white people” things. So I have thought about it, but I actively try to avoid thinking about it because it comes back to agency. Whether I’m Asian or not, it’s not something I can control.

I think being introverted is something a lot of Asians can relate to, so I asked him to drill down on that:

I felt like over time, you become confident in the things that you are good at. For me, at least, that was a big moment in my growth as a kid. Finding something that I could be proud of, something that I’m good at. And then you focus on that. I feel like once you have that, the introversion matters a lot less. Because you can focus on the thing that you’re good at and develop more confidence in there. As a byproduct, you sort of express or come off as less introverted.

What I took away from Siqi’s comments was that introversion/shyness and insecurity in your abilities were pretty related. I brought this up, and Siqi had a pretty interesting comment on the relationship between insecurity and extreme outcomes:

One of the things that a lot of entrepreneurs and high performing people have in common is this sense of insecurity. That also causes a desire to please people because you’re insecure. So that you have to push yourself to be better and you want to make sure other people like you because of that insecurity. And that is highly motivating for me, and I think many people. It’s like how people get, I think, to certain points in their life or certain levels of success, at least somewhat. And then once you’re there, all of those causes become less useful. Like, the insecurity, the willingness to please as a CEO, those are, like, really toxic things. That paradoxically got you to this point because it made you push yourself to be better. But once you’re there, it doesn’t get you further.  

BEING A LEADER

The last topic Siqi and I talked about was leading others, the first thing Siqi brought up was something he had recently heard in a Brian Chesky interview.

Brian described the job of a leader as believing that people can level up and exceed their own expectations and get them there. That was really a point of reflection for me. I believe in smart people and hiring and talent and all these things. But if you want to get the best out of people, the prerequisite is that you have to actually believe that they can be amazing. Because if you don’t even believe that, you’re not going to set those expectations or deal with any kind of motivation or inspiration.

I didn’t quite understand this, because I would expect Siqi to only hire people if he believed that they could be amazing. Siqi explained to me:

It’s just that my temperament is to quickly write people off. “They’re good at this particular role that we hired them for, and that’s all they’re going to do.” But people want to know that you have their interests in mind, that there is a growth path for them. If you don’t believe that there is, that’s a problem. You want to hire the best people that you can, but in how you lead and manage them, you have to always believe that they can do better than they are.

We also chatted a little about what made a good employee.

Edwin: One thing I’m curious about. What kind of person do you notice is the best employee? What matters more, their talent and technical ability or how much they believe or align with the mission of the startup?

Siqi: It’s a difficult question to answer because there’s a lot of wisdom out there that says, “This is the most important thing.” I think the reality is they’re all requirements. They’re all important. And you don’t want to compromise on any of those aspects. What are those aspects? High integrity, proactiveness, high agency. Some people think integrity is the most important thing. Others think intelligence is the most important. Those things are important, they’re all absolute requirements. You want extremely high intelligence, extremely high integrity, and extremely high self-awareness and agency. But out of all of those, I think the thing that is the most important is high agency. Intelligence is a lot of nature, so that’s fairly difficult to change, but there’s a certain baseline that you want.

But everything else outside of that is almost entirely driven by agency. Whether you are successful, whether you blame people, whether you can grow. Whether you’re a good collaborator, whether self-aware. There’s so many things that one thing affects. That is the thing that I look for the most. 

SHOUTOUTS

Runway is hiring for engineering and customer-success roles! You can check out current job openings at https://runway.com/careers/ 

[Hint: if this isn’t you but you still really want to work at Runway, I would drop Siqi a line and articulate how you would add value to the company, bonus points for bringing a demo/a plan]

If you are currently having financial planning problems, sign up for early access for Runway at https://runway.com/


Thank you to Siqi for chatting with us!

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The Fighter Mentality Driving Anthony Kwok, CEO and Co-Founder at ZILIO, to Fix Fashion’s Most Overlooked Problem

Anthony Kwok’s journey didn’t begin in a boardroom. It began in places that demanded discipline, resilience, and the ability to keep going when things got uncomfortable. First in the ring as a professional fighter, and later through a medical crisis that reshaped how he approached both life and leadership.

Those experiences now shape how Anthony runs ZILIO, a fashion tech company building AI-powered sizing solutions for brands and uniform providers. What looks like a startup on the surface is really the result of years spent learning how pressure exposes real problems, and how frustration often points to what needs fixing most.

At ZILIO, Anthony brings that mindset to one of fashion’s most overlooked challenges: the perfect fit. Not just as a sizing issue, but as a confidence issue that affects how people show up, move through their day, and feel in their own skin.

The Lessons That Carried Him Through

Before stepping into the tech world, Anthony spent his years as a professional fighter competing on FoxSports. Growing up Asian in a predominantly white environment, he felt he had to work twice as hard to be seen. This drive eventually led him to the ISKA Victorian Title. However, his toughest fight came outside the ring when he suffered two strokes the same year he founded ZILIO.

Walking away would have been understandable. Instead, Anthony leaned into the discipline he learned as a fighter. As he puts it, “Being a professional fighter taught me one non-negotiable principle: Never quit. No matter what. That philosophy carried me through recovery and continues to guide how I build today.”

Solving the “Booty Short” Problem

The idea for ZILIO was born from personal frustration. As an athlete with a specific build, Anthony found online shopping to be a constant gamble. He still remembers ordering gym shorts that arrived fitting like “booty shorts,” an experience that made him wonder why we can dress video game avatars perfectly but struggle to do the same in real life.

ZILIO solves this by replacing confusing size charts with accurate AI recommendations. The company started with corporate uniforms, where poor fit creates massive operational headaches for brands like Coles and Australian Unity. The impact was immediate. ZILIO has helped partners cut returns by 40% and significantly boosted customer engagement by giving them a fit they can trust.

Anthony Kwok (right), CEO and Co-Founder of ZILIO

Helping People Stop Second-Guessing Their Bodies

For Anthony, this mission is personal. He knows that standard size charts often fail people with diverse backgrounds and body types, including many in the Asian community. His goal is to make sizing “invisible” so that people can focus on their style instead of their anxiety.

“Fashion is deeply emotional, and a bad sizing experience can stop someone from exploring style altogether,” Anthony explains. “ZILIO exists to navigate that complexity and give people clarity and confidence, regardless of body type or background.”

With $500,000 in funding and awards like the B&T 30 Under 30, Anthony is proving that a kid with a big imagination can change a global industry. Whether it’s through his upcoming 3D virtual fitting rooms or his work with major brands like Rebel Sport, he is making sure that the next time you shop online, you’re buying a piece of clothing that actually fits your life.

Discover more about Anthony Kwok here:

📍LinkedIn📍Instagram

Learn more about ZILIO here:

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From War Survivor to Literary Leader: The Remarkable Rise of Amy M. Le, CEO of Quill Hawk Publishing

Amy M. Le, CEO of Quill Hawk Publishing, has built her life around stories that matter. Not the polished kind that skip the hard parts, but the honest ones shaped by loss, survival, and growth. Her journey reflects how personal history can quietly become a source of strength.

Every stage of Amy’s life pushed her to adapt and redefine what success looked like. She learned early that resilience is not loud or dramatic, but steady and intentional. Over time, those lessons shaped the way she approaches both writing and leadership.

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Photo courtesy of Amy M. Le, CEO of Quill Hawk Publishing

Born in War, Saved by Courage

Amy M. Le was born during the final months of the Vietnam War, a period defined by intense fear and systemic instability. As an infant, she faced a life-threatening heart condition that put her future in jeopardy before it had truly begun. Because medical resources were scarce in a war zone, her survival was never a guarantee.

Driven by a mother’s fierce love, her family made the harrowing choice to flee Vietnam in search of safety and essential medical care. This escape carried enormous risks, yet it was fueled by an unwavering hope for a life free from conflict. That courageous decision ultimately changed the trajectory of Amy’s life, setting her on a path toward a new world.

Photo courtesy of Amy M. Le (far right), CEO of Quill Hawk Publishing

A New Life and a Turning Point

Their journey eventually led them to Seattle, where Amy underwent the life-saving heart surgery she so desperately needed. This successful procedure gave her much more than physical health; it provided a second chance and a profound sense of purpose. With this renewed vitality, she grew up determined to make the most of every opportunity her new home provided.

Following this recovery, Amy spent over twenty years navigating the high-pressure tech industry to build a stable and successful career. However, the trajectory of her life shifted once again when she faced the devastating loss of her mother. In the wake of this grief, she turned to writing as an essential lifeline to heal her heart and rebuild her sense of identity.

Photo courtesy of Amy M. Le, CEO of Quill Hawk Publishing

Turning Story into a Mission

That personal healing became The Snow Trilogy, a powerful book series telling the true story of her family’s escape from Vietnam and their new life in America. The books resonated deeply with readers who saw their own stories reflected in its pages. What began as personal healing became a collective connection.

Inspired by that impact, Amy founded Quill Hawk Publishing, a hybrid company built to empower authors without stripping away their creative freedom. In just three years, the company has grown to support 70 authors from Seattle to Sydney, proving that no matter where you begin, you can always rewrite your story and help others tell theirs too.

Discover more from Amy M. Le here:

📍Instagram

Learn more about Quill Hawk Publishing here:

📍Website

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4 Creative Ways Trysen Kaneshige Uses Art to Keep Aloha Alive

Some artists create for attention or fleeting trends, but Trysen creates with intention, guided by a deep sense of responsibility to the culture that shaped him. Growing up in Hawaiʻi, he learned that Aloha is not just a feeling, but a way of living rooted in care, respect, and connection.

That belief now guides both his art and his creative studio, Inspire to Create Media. Through murals, design work, and storytelling projects, Trysen uses his business as a platform to protect culture while helping others share their stories with intention.

1. Reviving Local Stories Through Murals

 

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At the core of Trysen’s work is listening. On Kauaʻi, he spends time learning from residents about their histories, struggles, and sources of pride before creating any artwork. This approach reflects the values he also brings into Inspire to Create Media, where storytelling always begins with people.

The murals that follow are rooted in real voices. They transform blank walls into visual records that help locals feel represented and allow visitors to understand the island through the community’s lived experience.

 

2. Designing With Aloha in Mind

 

Photo courtesy of Trysen Kaneshige, Founder of Inspire to Create Media

Aloha influences how Trysen collaborates, how carefully he considers each element, and how much intention goes into every decision. Design, for him, is about respect as much as aesthetics. That same mindset shapes the design work produced through Inspire to Create Media. 

Whether creating branding, apparel, or custom visuals, his goal is to make work that feels warm and grounded. Each piece is designed to reflect care, balance, and a sense of home rather than fleeting trends.

 

3. Empowering Youth and Community Spaces

 

Photo courtesy of Trysen Kaneshige (fourth from left), Founder of Inspire to Create Media

Beyond client work, Trysen uses both his art and his studio to invest in the next generation. Through partnerships with schools and wellness programs, Inspire to Create Media supports projects that turn shared spaces into places for expression and growth.

By involving young people in the creative process, he helps build confidence and identity. These initiatives focus less on the final product and more on giving youth a voice and a stronger connection to their roots.

 

4. Building a Global Bridge From Island Roots

 

Photo courtesy of Trysen Kaneshige, Founder of Inspire to Create Media

While his work is deeply rooted in Hawaiʻi, its reach continues to grow beyond the islands. Through collaborations with global brands like Volcom and OluKai, Trysen shares an authentic island perspective with a wider audience.

These partnerships amplify his message without compromising its foundation. By staying grounded in culture, he shows that it is possible to connect with the world while remaining true to where you come from.

 

Photo courtesy of Trysen Kaneshige, Founder of Inspire to Create Media

 

Carrying Aloha Forward

At its core, Trysen’s work—through his art and his studio, Inspire to Create Media—is an ongoing act of care. Through each project, he honors his home, uplifts his community, and uses creativity as a way to carry Aloha forward with intention, respect, and lasting impact.

More than anything, his work reflects a belief that culture is something you actively protect and pass on. By choosing collaboration over ego and meaning over trends, Trysen ensures that Aloha is not only preserved, but lived, felt, and shared with future generations.

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From Jackie Chan’s Assistant to Building Paire: How Nathan Yun’s Vision for Better Essentials Became a $15M a Year Brand

Nathan Yun did not start his career thinking he would one day build a consumer brand. His early years were spent on film sets and in editing rooms, learning how stories are shaped and how audiences respond to them. Working as an assistant to Jackie Chan gave him a front-row view of storytelling at its highest level. He watched how a single film could reach millions of people and create a shared emotional moment across cultures.

Yet over time, he noticed something that stayed with him. The inspiration was real, but it faded quickly. Once the credits rolled, people returned to their usual routines. That contrast made him question what lasting influence really looked like. Was it found in big, unforgettable moments, or in the small things people interacted with every day?

Paire grew out of that question, built not around trends or marketing tactics, but around everyday essentials, starting with socks. If stories could move people for a moment, Nathan believed products could shape how they lived every day.

From Film Sets to Daily Habits

Nathan came to understand that while stories stay with people selectively, habits are formed through repetition. Clothing, especially everyday essentials, plays a quiet but constant role in daily life. When something feels uncomfortable or wears out too quickly, people notice it immediately, even if they never say it out loud.

This insight marked a turning point. Nathan no longer wanted to create something people felt for a moment. He wanted to build something they could rely on every day. From the beginning, Paire was shaped around that idea.

Instead of chasing trends, the brand focused on fit, fabric, and longevity. The goal was simple: to make essentials people would reach for again without thinking.

Nathan Yun (right), Founder of Paire

Learning How to Build Before Building His Own

Before launching Paire, Nathan spent five years at furniture startup Brosa, where he learned what it takes to grow a business beyond an idea. As the company expanded from a ten-person team to more than one hundred employees, his role evolved from content creation to leading brand and marketing.

During that time, he saw how forecasting affected inventory, how data guided growth, and how pressure increased as operations scaled. He also witnessed what happened when demand moved faster than systems, and how costly it could be to build those systems too late.

Those experiences shaped how Nathan approached entrepreneurship. He did not want to build Paire on instinct alone. He wanted a clear understanding of supply chains, margins, logistics, and customer behavior before committing to his own brand.

Nathan Yun (far right), Founder of Paire

The Trip That Made the Mission Personal

The purpose behind Paire became clear during a trip to India. Away from polished storefronts and online campaigns, Nathan saw the fashion industry in a very different light. He witnessed environmental damage near production sites and spoke with workers whose livelihoods depended on high-volume manufacturing.

“That experience made it clear something needed to change,” Nathan explains. What stayed with him most was how disconnected these realities were from everyday shopping habits.

Much of the damage he saw came from clothing treated as disposable. When he returned home, Nathan reached out to his longtime friend Rex, a textile expert. Instead of launching a wide range of products, they chose to start small. The focus was on improving a single item and making it last.

Nathan Yun (left), Founder of Paire

Earning Trust Through the Product Itself

Nathan understood that values alone would not earn loyalty. The product had to prove itself in everyday life. The team spent months refining fabric blends, improving breathability, and testing durability through repeated wear and wash cycles.

Pricing a pair of socks at twenty-four dollars came with risk. Most consumers were used to buying socks cheaply and replacing them often. But once people tried Paire, many returned. Nearly seventy percent became repeat customers, not because of marketing, but because the product became part of their routine.

By focusing on quality and longevity, Nathan Yun built a $15M-a-year brand that shows meaningful change does not always arrive loudly. Sometimes, it begins quietly, through the simplest things we rely on every day.

Follow Nathan’s journey:

📍 Website
📍 Instagram | LinkedIn