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June 13, 2024

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Tracy Young is a founder who has been on my radar for a long time. Beyond the fact that she is a successful exited founder, having sold PlanGrid to Autodesk for just under $900 million, Tracy’s family–like my own father–immigrated to the United States following the Vietnam war. With one major success under her belt, Tracy is going for a second, having recently founded a new startup named TigerEye, which focuses on AI-powered strategic planning. I sat down with Tracy to chat about lessons from PlanGrid, what she’s currently working on at TigerEye, and her identity as an Asian woman.

On Identity

I wasn’t the only one with a newsletter on the call! Tracy also recently started a LinkedIn newsletter titled Predictable Growth, a monthly Q&A with women leaders generating revenue for their businesses. I asked Tracy what the motivation behind starting it was, and what she hoped to see it accomplish:

Representation matters. In sales and go-to-market functions, women are underrepresented at the leadership level. However, many impressive, talented, and hardworking women have achieved the CRO/CMO level, and I wanted to hear their stories. So, it’s a way for us to showcase women and give them a platform to tell their stories and how they got to where they are. There are many great jobs in sales, but many women don’t realize that they’re available to them. Anyone can be good at sales, it’s not just men. Reaching the highest levels in sales gives women a lot of power to help out their families, help the economy, etc.

In previous interviews, Tracy has pointed out how women are especially underrepresented in enterprise SaaS. I asked Tracy if she had any ideas why this is the case, and how we can increase representation:

I’m not sure why that’s the case. But you can see it if you look at the stats or walk into any enterprise company. I would guess it’s systemic. I think it starts with the words we use for boys and girls, the way we treat them, and what is expected of them. This is part of our cultural history. One way to change that is to show what is possible. What Predictable Growth aims to achieve is to showcase all these women who are leaders at their companies. There’s no decision that the CEO is making without running it by them. We want to say: “This could be your future, if you want it”, for anyone reading, and hopefully, it’s a young woman reader.

Next, I wanted to get Tracy’s thoughts on how being an Asian woman has affected her experience as a founder:

My PlanGrid co-founder, Ryan, and I met in college. He’s been trying to convince me to start a company with him since I was 18. Being an Asian woman, I didn’t think it was possible. I brushed him off for many years. I thought, “I’m not a founder,” because I looked at all these other founders, and they didn’t look like me. That kept me from starting a company for a long time. Around 2007-2009, I remember Ryan really wanted me to apply for Y Combinator with him. And again, I told him, “I just don’t think it’s going to work.” I didn’t think other people would accept me, and I didn’t want to put myself through it. It wasn’t until Y Combinator put out a request for startups working on the exact problem we were working on that I felt comfortable applying. That request for startups almost gave me permission to apply to YC. But even when we got in, and we were making real revenue, and we fundraised, and we had real customers, and our product was getting better… even then, I still felt that founders should look a certain way. I don’t know how many years in we were before I finally realized how wrong I was.

In an interview eight years ago with Ron Miller at Techcrunch Disrupt, Tracy responded to a similar question very differently. I asked her what motivated her shift in perspective since then:

Back then, I really tried to separate myself from being a woman. I felt like that was not part of the equation. And again, it’s such a big part of me, I am a strong woman. For many years, I pretended that I wasn’t, down to how I dressed. What really woke me up was becoming a mom. Going through pregnancy and birth and postpartum recovery, and taking care of a baby, I think it was really at that point when I realized how strong women are, how strong our mothers and grandmothers are, and how strong my colleagues are. It was a disservice not to acknowledge that our journey is different. It’s not better or worse. It’s just different.

TigerEye

I asked Tracy how she came up with the idea for her new startup, TigerEye:

There’s no shortage of problems to solve in business software. If you talk to anyone who works for a public company, you’ll find a lot of outdated software still in use. After selling my last startup, I worked for a public company and got to use these expensive products that our company was paying for every year. I saw firsthand how they made us less productive and frustrated our team. Many areas need improvement, such as HR software, finance software, sales software, and everything in between, including development tools. 

A common strategy I hear from founders is that they want to start by selling to other startups, and then grow into an enterprise software company alongside their clients. I asked Tracy how she decided to skip that and go straight for enterprise customers:

I like to solve problems that I have experienced. TigerEye comes from my experience running a fast growth company for ten years. When we reflected on our PlanGrid journey, we asked ourselves a few questions: What would have accelerated growth? What would have made the difference between us still running PlanGrid today versus needing to sell? TigerEye is that product. This is a scientific tool that would have helped us grow more efficiently, be more profitable, and would’ve enabled us to be more courageous in our decision-making by providing extra validation. It’s an AI-powered business simulator. You can test out your plans before you make your team execute it. You can test out as many plans as you want and as many scenarios as you want before you bring it to the board for sign-off. Back at PlanGrid, we had a bunch of very smart people trying to generate the same thing that took months that TigerEye is outputting instantaneously now. This is the product that I wish I had to help grow PlanGrid. And this is why we are building for the enterprise. All I know to do is build things to help me with problems I’ve faced.

Starting a Company as a Second-time Founder

I asked Tracy what she thought about distribution at PlanGrid, and how that has changed for TigerEye:

PlanGrid was always mobile first. We really benefited from timing. Steve Jobs announced the first generation iPad, and we decided to start building construction software for that device soon after. We were one of the first enterprise apps to launch on all of the app stores. 

Let’s say you’re a construction person and you’ve got your new iPad or other tablet. You search for construction because that is your profession, and PlanGrid pops up as the top result. If it looks interesting, you might download it, and we had a freemium model so users could try us out. As a mobile-first company, having great SEO on the app stores was crucial for our inbound growth. That’s how we thought about distribution for PlanGrid, but that is totally irrelevant for TigerEye (although we do have a mobile version of our software). TigerEye is an enterprise-grade product, and you can’t just try it out as an individual. It is being deployed to whole departments, and that is a completely different distribution model. For many years, PlanGrid was sold on a per-seat basis. At TigerEye, we have an unlimited seat model, and it’s deployed to several teams at once, and the starting fee is five figures. It’s an enterprise-grade product. And so for us to get deployed and adopted usually takes a field sales team two or three conversations with the company, because it’s not just sales, it’s revenue operations, it’s strategic finance, and then it’s a champion at the C-suite level. It’s very different from PlanGrid’s model, where anyone with a credit card in a job site could swipe their credit card and buy PlanGrid today.

Next, I asked if she felt that being a second-time founder came with any benefits:

There are definitely benefits. For example, the first 15 people we recruited were people we had handpicked and worked with before. As a result, we were able to recruit a talented team with a strong track record and a strong work ethic. It’s difficult for first-time founders in their early 20s to attract talented individuals. The people who worked for us were our friends or recent college graduates. From our decade of experience, we’ve also seen what works and what doesn’t in terms of core values. This time, we made sure to have a set of values that we live by personally and professionally. These core values are non-negotiable and we share them with candidates we’re trying to recruit during our first phone call. We’re serious about it. Everyone says they care about their core values, but we actually hire and fire by them. 

Tracy’s emphasis on core values stood out because this was the first time I had heard a founder emphasize them to this degree. I asked Tracy why this mattered so much to her:

Through my experience growing PlanGrid to 450 employees and scaling the team to 1,300 employees post-acquisition, I got to see what slows down a team. I got to see how infighting can destroy a company. There are minor things that you can put in place to mitigate this, such as basic rules of engagement. We have a document called “Our commitments to working with each other,” which outlines how we work together at TigerEye. The document clarifies our five core values. It’s very simple, you cannot misinterpret what the core values mean. I’ll give you a couple of examples: 1) I will walk it like I talk it. 2) I will never speak destructively behind my teammate’s back. 3) If I have a problem, I will go to you and talk it out because we’re professionals and I can trust that we can have the hard conversations. If everyone follows these rules, then we’re in a really good place. That means that when there are problems, we can speak openly as a team and get through it together. We were very deliberate about the culture and work environment we were creating, especially as a remote company. I think our culture is especially important because we aren’t together every single day.  

Fostering a Culture of Authenticity

Throughout my research, a consistent theme Tracy touched on was being authentic as a leader. I asked her if she felt there are boundaries to authenticity and if it’s fine for CEOs to express fear or lack of confidence to their team.

There is definitely a line in terms of vulnerability and authenticity. It’s never acceptable to be disrespectful. Some might argue that they’re just being direct, but there’s a difference between being direct and being rude. It’s okay to question things and suggest new approaches. When I’m concerned about something related to the company, I share it with the team. I either present a potential solution or let them know that I’m working on one. This approach makes it easier to lead and get the team on board with the direction we’re heading. They may not always agree, but at least they understand why I’ve made certain decisions. If they understand, it’s easier for them to commit to the decision, even if they initially had reservations. 

To your second question, I think it is completely okay for a leader or anyone in the company to show that they are human, and as humans we experience fear and insecurity–they are natural emotions. As a leader and a productive teammate, it isn’t beneficial to dwell on these negative emotions. It’s challenging, if not impossible, to suppress these feelings because they will eventually surface. My approach is to allow myself to experience these emotions when things are tough, but also to take control and not let them linger. For instance, I might allow myself a day to experience these feelings, but the next day, it’s time to put on a game face and figure things out together. As long as there’s movement and progress, then it’s okay. Feelings like anger, insecurity, and sadness, when prolonged, are completely useless. They don’t serve anyone any good. They’re just there making everyone feel bad and that is absolutely not okay.

I asked Tracy what actions she takes to make sure everyone on her team is comfortable being authentic and vulnerable with each other:

We do this fun activity. We all take the Enneagram test. New teammates will take the test and present their enneagram results sometime within the first few weeks. The presentations are basically: “This is when I’m at my best. This is how I am at my worst. This is how I want to get feedback.” This helps us understand who we are as people because there are all kinds of different personalities, and conflict comes from two personalities at their worst coming together. If we can acknowledge and understand that might happen, it’s easier to get through it together. Essentially, it’s having self-awareness and giving your team a blueprint of being aware of who you are. 

For those who don’t know, Enneagram is a popular personality test that emphasizes how you interact with other personality types, making it a popular choice for teams. I am normally skeptical of these kinds of tests, but even I am a big fan of Enneagram, and I think it has helped me better understand myself and my interactions with others. For those curious, Tracy is Enneagram type 1, “The Reformer”. A fitting type for a person with such ambition and vision.

Shoutouts

If you are a leader in sales, RevOps, finance, or marketing, TigerEye has built a go-to-market planning tool to help you track, plan, and predict your go-to-market performance. The tool analyzes every change in your CRM using artificial intelligence to guide decisions and show you where you’re headed.

If you are interested in checking out what Tracy and TigerEye. have built, please drop her a note on LinkedIn or on X (f.k.a. Twitter) @Tracy_Young. Thank you Tracy for the interview!

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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:

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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.

Today, Amy’s work centers on creating space for voices that are often overlooked. Through publishing and community-building, she helps others turn lived experience into stories that resonate far beyond the page.

 

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.

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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

 

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

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:

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