Awaken* newsletter

March 14, 2024

SHARE:

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!

Related Articles

unnamed-jpg

Stories

The Spirit of a Fighter: How Stepping Into a Muay Thai Ring Changed the Way Alice Shikina Works as a Mediator and Negotiation Trainer

The first time Alice Shikina stepped into a Muay Thai ring, the moment felt bigger than the fight itself. The gloves were heavy, but what weighed more was everything she had been carrying in the months before.

She was in her late thirties, newly divorced, and raising two young children on her own. Her kids were just two and five years old, and the life she had carefully built no longer looked the same.

At the same time, she was trying to establish herself as a mediator and build her own business from the ground up. She didn’t know it yet, but the self-trust she was about to forge in that ring would become the foundation of how she led others through their own conflicts.

The Fight Before the Fight

Kickboxing began as a way to cope during a season that felt completely overwhelming. It gave Alice a physical outlet when her thoughts wouldn’t quiet down and her emotions felt too heavy to carry.

A few months later, Alice’s coach asked if she would consider competing. The idea unsettled her because she had never fought before and had never faced someone trained to strike back. For two months, she wrestled with the decision. What frightened her most was not losing, but the possibility of doubting herself under pressure.

When she finally committed, her routine became disciplined and demanding. She trained three hours a day, carving out time in the early mornings and late evenings while continuing to care for her children and grow her work.

The night before her first fight in Iowa, a coach told her that the real fight was already over because it happened during the grueling months of preparation. Once she realized that, her nerves calmed and a quiet steadiness took over. Even as she approached the ring to step in and fight, she felt unusually calm. She didn’t win that match, but she stayed on her feet until the final bell, and for a woman rebuilding her life, that was more than enough.

What the Ring Taught Her About Pressure

Alice went on to fight three more times. Afterwards, Alice turned her sights to competing in triathlons and even placed first in her age group at the Alcatraz Duathlon. While the medals were nice, the real reward was the quiet discipline she built through the discomfort of training.

She came to understand that fear does not simply fade with time. It softens only when you decide to move toward it.

She also learned that preparation changes how you carry yourself in difficult moments. When you put in the work, you stand differently, breathe more steadily, and think more clearly under pressure.

Today, those lessons shape how she sits with couples navigating divorce and teams facing workplace conflict. When emotions rise and conversations begin to unravel, she remains steady, drawing on the same discipline that once kept her composed in the ring.

Building Her Practice on Her Own Terms

Alice now runs Shikina Mediation and Arbitration full-time, helping divorcing couples, families, and organizations reach agreements they once thought were out of reach. Most clients come to her when communication has broken down and trust feels fragile.

Early in her career, she tried building her business by networking with attorneys, but quickly saw the bias against non-attorney mediators in a field long dominated by older white men. Instead of forcing herself into a system that did not fully welcome her, she shifted her focus to working directly with couples and workplace clients, growing her practice into a thriving full-time business over the past decade. In 2025, Alice was awarded the prestigious Raymond Shonholtz Visionary Peacemaker Award by San Francisco’s Community Boards.

Her work has expanded beyond the mediation room. She hosts the podcast, Negotiation with Alice, now over 100 episodes strong. She authored the book Negotiating with Your Kids, and continues to teach communication and conflict resolution to executives and C-Suite staff. As a second-generation Okinawan American whose parents survived the Battle of Okinawa as children, resilience runs deep in her story. 

Nothing in business, she says, will ever feel as intimidating as stepping into a ring to face an unknown opponent. In that ring, she rebuilt her confidence. At the mediation table, she now helps others rebuild their lives with clarity, courage, and peace.

Discover more from Alice Shikina here:

📍LinkedIn

Learn more about Shikina Mediation and Arbitration here:

📍Facebook

📍Website

99-jpg

Stories

From a Childhood Dream to the Red Carpet: How Elenor Mak’s Two-Year Mission to Give Michelle Yeoh a Personalized Doll Finally Happened

What started as a small tribute from a mother turned into a two year journey filled with patience, rejection, and hope.

Elenor Mak simply wanted to honor Michelle Yeoh and show her daughter that Asian girls can be the hero of the story too.

No one expected that the journey would end on the red carpet at the Hollywood Walk of Fame.

Image source: Elenor Mak

The Childhood Inspiration

Elenor Mak grew up watching Michelle Yeoh on Cantonese VHS tapes at home. Seeing an Asian woman lead films and command the screen made a deep impression on her as a child. It showed her that someone who looked like her could be strong, fearless, and at the center of the story. That belief stayed with her for years.

When Michelle Yeoh won the Academy Award for Best Actress, Elenor listened closely to the speech. Michelle spoke about being a beacon of hope for children who were waiting to see themselves represented. The moment felt personal to Elenor. That was when she decided to create a doll that captured that historic win.

Image source: Elenor Mak

A Two Year Mission

Creating the doll was a careful process that took five months. A professional stylist in Los Angeles helped shape the look, while a supporter in Hong Kong hand sewed the detailed feathery gown. Each part was made slowly and thoughtfully. Everyone involved wanted the doll to reflect Michelle Yeoh’s iconic Oscar moment.

At the center of it all was Elenor’s mother. She sat at the kitchen table attaching the final accessories with crazy glue and steady hands. When the doll was finished, the real challenge began. For two years, Elenor tried to find a way to get the doll into Michelle Yeoh’s hands.

Image source: @jonmchu (Instagram)

The Hollywood Moment

When Michelle Yeoh’s Hollywood Walk of Fame ceremony was announced, Elenor knew she had to try again. She flew to Los Angeles with her friend Dion Lim, an Emmy Award winning journalist, hoping for one last chance. They waited behind barricades for hours as the crowd gathered. After hearing no from security several times, they almost gave up.

Then something unexpected happened. Janet Yang, a producer and former head of the Academy, stepped in and helped make the moment possible. Soon after, Michelle Yeoh lifted the doll on the red carpet while Sandra Oh and Awkwafina cheered nearby. For Elenor, the moment meant more than giving a gift. It was for the little girl who once watched Michelle Yeoh on old VHS tapes and believed she could belong too.

IMG_9529-jpeg

Stories

Jonathan Quach Was Told He Was Too Young and Too Asian to Lead—Now He’s Built Team Quachro Into One of California’s Largest Youth Basketball Platforms

At 19 years old, most people are still trying to figure out who they want to become. Jonathan Quach, who also goes by Johny, was already thinking about how he could create space for others to grow.

He did not have investors backing him or access to elite facilities. What he had was a deep love for basketball and a growing frustration with how many talented kids were being left out of high-level programs simply because they lacked money, connections, or visibility. 

The name Team Quachro (TQ) was originally created just to enter his first eight kids into a local youth league. What started as a play on words from his last name, ended up becoming a staple in the Orange County Basketball community, competing with the other heavy hitters in the industry.

Starting at 19 with Nothing but Belief

Starting a program at 19 meant stepping into rooms where almost everyone was older. Johny had to lead coaches and speak with parents who had decades more life experience than he did. When he had only 50 kids in the program, a handful of larger, established programs recognized the early growth and tried to buy him out from the start.

As Team Quachro began gaining attention and players began leaving other programs to join his team, some competing coaches sent negative emails to others behind his back. Instead of responding with arguments, Johny chose to respond with action. He focused on developing his athletes and strengthening the culture of the program.

Now 26 years old, Johny has built one of the largest basketball programs and tournament operations in California. By remaining consistent and treating every family with respect, he gradually turned early skepticism into long-term trust. Team Quachro now serves more than 300 athletes, with thousands of families having come through the program over the years.

Carving a New Lane for Asian Leadership

Building one of California’s largest platforms by age 26 is a feat in itself, but doing so as an Asian founder carries even more weight. In the youth basketball world, Asian founders are rarely seen in leadership roles. Johny understood that reality and wanted younger players to see someone who looked like them leading from the front.

Representation, for him, was not about making statements. It was about building something real and lasting that could create opportunity for others. Every partnership and every opportunity had to be earned through persistence and relationship building.

Over time, that work transformed a small training group into one of the most respected sports organizations in California. Johny proved that leadership is not determined by age, background, or stereotype. It is shaped by commitment, integrity, and care for the people you serve.

Leaving a Legacy Bigger Than Trophies

What began as a handful of local training sessions has grown into a thriving ecosystem of teams, tournaments, and mentorship. The results of that dedication are visible at the next level, with TQ athletes playing at the Division I college level, as well as at JUCO and NAIA programs.

Despite that growth, Johny has worked intentionally to keep the heart of the program intact. He continues to cover costs for athletes who cannot afford to participate and organizes free clinics to make the game more accessible. He believes that financial limitations should never be the reason a child cannot pursue their potential.

Johny did not inherit a platform, and he did not receive a head start. Today, the program stands as more than a basketball organization. It stands as a family built on loyalty, mentorship, and shared belief. For him, that culture is the greatest achievement of all, far greater than any trophy or tournament win.

Discover more from Johny Quach here:

📍Instagram

Learn more about Team Quachro Basketball here:

📍Website

image (1)-png

Stories

Taiwan Heir Andre Koo Jr. Steps Beyond a $6.3B Dynasty to Build the Future of AI in New York City

Andre Koo Jr. was born into one of Taiwan’s most influential business families, where legacy and leadership have shaped industries for more than a century.

As a fifth-generation heir to a $6.3 billion empire, he had every reason to remain within the comfort and stability of an established dynasty.

Yet instead of staying home, he chose to build something new in New York, placing a focused bet on the future of artificial intelligence.

Image Source: NYU Stern

Honoring a 130-Year Legacy While Charting His Own Path

For generations, the Koo family has played a defining role in Taiwan’s business landscape, building institutions that span finance, infrastructure, and beyond. Growing up within that environment meant understanding both the privilege and the responsibility tied to the family name. Legacy, in this case, was not just inherited wealth but a long-standing commitment to growth and impact.

Still, Andre Koo Jr. believed that honoring tradition did not require standing still. While remaining actively involved in the Koo Family Office, he set his sights on expanding the family’s global footprint. His move to Manhattan marked a deliberate step toward independence, signaling a desire to test his vision in one of the world’s most competitive markets.

Image Source: Private Wealth Institute

Building K8 Capital for the AI Era

That vision took shape through K8 Capital, a firm designed to invest in artificial intelligence and enterprise software. Rather than following typical venture capital models, Andre structured a hybrid strategy that blends private credit with venture investments. This approach allows him to pursue innovation while maintaining disciplined risk management.

The strategy is already delivering results, with gains of over 50 percent achieved through carefully structured short-term loans. K8 Capital has secured five major investors and is actively deploying capital into promising technology companies. By combining the prudence of established wealth with the speed of modern tech investing, Andre Koo Jr. is building a bridge between a historic dynasty and the next generation of innovation.