Awaken* newsletter

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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Stories

Steve Liu Knows How to Draw a Crowd. With TRI3E, He Wants to Help Communities Grow.

From producing shows with major artists to leading product design at Amazon and Palo Alto Networks, Steve Liu knows a thing or two about bringing people together.

With TRI3E, he’s using what he’s learned to help people, creators, businesses, and organizations build stronger communities.

Understanding What Brings People Together

Filling a venue is one thing. Getting people excited enough to bring their friends is another. Steve Liu learned that firsthand in San Francisco’s nightlife scene.

As a nightclub promoter and event producer, he helped organize shows featuring The Chainsmokers, Far East Movement, MC Jin, and comedian Ali Wong.

What stood out to Steve wasn’t just how people discovered events, but what happened when they came together. Friends brought friends, new connections formed, and people found a sense of belonging through shared experiences.

He realized that the most meaningful part of bringing people together wasn’t filling a room. It was creating experiences people genuinely enjoyed, felt part of, and wanted to share with others.

A Different Way of Looking at Problems

Outside entertainment, Steve was building a career in technology. He eventually led product design teams at Amazon and Palo Alto Networks, working on products involving cloud computing, global supply chains, and cybersecurity.

The work was different from organizing events, but it taught Steve how to approach complex, multidimensional problems. Working across technology, business, and human needs, he learned to connect different perspectives, navigate competing priorities, and turn complicated challenges into practical solutions.

His experience as an entrepreneur also gave him a firsthand understanding of how difficult it can be to grow a business, reach the right people, and keep them engaged.

Over time, those experiences started to come together. He had seen how people brought others into events and communities, and he understood how technology could help make those connections easier.

That got him thinking about what better community-building tools could look like.

Helping Communities Do More Together

Think about a restaurant planning an event, a creator looking to bring supporters together, or a community organizer trying to reach more people.

They already have people interested in what they do. The challenge is finding ways to get those people involved, keep them connected, and encourage them to bring others along.

That’s the thinking behind TRI3E (Tribe), the platform Steve is building.

TRI3E aims to help individuals, creators, businesses, and organizations build and grow their communities. Through the platform, they can share events and opportunities, invite others to participate, and give members more ways to stay involved.

For a restaurant, that could mean inviting regular customers to an event and encouraging them to bring friends. For a creator, it could mean sharing a new project with supporters. For an organization, it could mean helping members discover opportunities and meet others with similar interests.

The goal is to make it easier for people to stay involved, bring others along, and create more opportunities within their communities.

Building What’s Next

For Steve, TRI3E is an opportunity to bring together years of experience in technology, entrepreneurship, and entertainment around an idea with much broader potential.

Whether it’s a neighborhood restaurant, an independent creator, or a network like Asian Hustle Network, communities already have people who want to see them succeed.

What if those people had better ways to make that happen?

That’s the vision behind TRI3E: helping people turn their existing connections into more opportunities for their communities.

Join TRI3E

Build your community. Activate your network. Grow together.

Explore TRI3E | Connect with Steve

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Stories

ChargerGoGo’s Next Chapter: GoGoSpark Brings AI-Powered Entrepreneurship to the Future of Work

ChargerGoGo built its nationwide phone charging network by betting on everyday entrepreneurs.

That bet is paying off. In 2026, ChargerGoGo landed at No. 744 on the Inc. 5000 (top 15%), No.5 in Las Vegas, and No.41 in AI and Data industry, the annual ranking of the fastest-growing private companies in America, after reporting 467% revenue growth over three years.

Led by founder and CEO June Zhu, the company has spent years helping local operators build businesses through its charging network. With GoGoSpark, it’s bringing AI into the picture.

Launched at CES 2026, GoGoSpark is ChargerGoGo’s AI-powered business copilot and operations assistant, built to help operators handle the day-to-day work of running and growing their businesses.

What Does GoGoSpark Actually Do?

As AI reshapes the workforce, the next economic opportunity is not only about making employees more productive, it is about giving more people the tools to become business owners.

GoGoSpark was built around that mission.

ChargerGoGo believes the future of work will include a growing number of people, across both white-collar and blue-collar professions, who want to build independent income, own productive assets, and operate businesses of their own. But becoming an entrepreneur requires far more than capital or a good idea. New business owners need help with sales, operations, financial decisions, technology, strategy, and the hundreds of decisions that come with running a company.

GoGoSpark is designed to put that capability in their pocket.

Serving as an AI-powered COO and business mentor available 24/7, GoGoSpark can help entrepreneurs analyze performance, identify opportunities, improve sales, troubleshoot operational issues, understand financial decisions, and determine what actions to take next.

The vision extends beyond operating ChargerGoGo stations. ChargerGoGo is building GoGoSpark as an intelligent business platform that can lower the barriers to entrepreneurship and help everyday people transition from employees into capable, technology-enabled business owners.

In an economy increasingly shaped by AI and automation, ChargerGoGo believes AI should not simply replace work. It should help more people create, own, and participate in the businesses of the future.

GoGoSpark does not replace the entrepreneur. It gives the entrepreneur a COO, an advisor, and a mentor in their pocket—so they can make better decisions and build with greater confidence.

Five Years in the Making

GoGoSpark came out of five years of working directly with thousands of operators, partners, and small business owners.

Over that time, ChargerGoGo saw the same kinds of questions come up again and again: How do I sell this better? Why is one location outperforming another? What should I focus on next? How can I run this more efficiently?

Those real-world questions helped shape what GoGoSpark became.

Rather than building AI for the sake of having AI, ChargerGoGo built a tool around the work its operators were already doing.

As Zhu said when the platform launched, “GoGoSpark is built to be a business co-pilot, helping operators learn faster, operate smarter, and participate in the post-work economy.”

The Bigger Goal Behind GoGoSpark

The Inc. 5000 ranking is a milestone for ChargerGoGo, but Zhu has been clear that she wants the company’s growth to reach beyond ChargerGoGo itself.

When the ranking was announced, she pointed to a bigger goal: giving ChargerGoGo’s Distribution Partners the technology, infrastructure, business model, and support to grow companies of their own.

She even said she hopes to one day see those entrepreneurs make the Inc. 5000 themselves.

GoGoSpark is one way ChargerGoGo is trying to make that happen.

As AI becomes part of how companies sell, analyze data, plan, and operate, smaller business owners risk being left with fewer resources to compete. GoGoSpark brings some of those capabilities directly to the people running businesses on the ground.

ChargerGoGo’s acceptance into the NVIDIA Inception Program also marks another step in that direction as the company continues developing its AI technology.

“The future belongs to those who engage with their AI,” Zhu said at CES 2026. “Our mission is to make sure everyone has that chance.”

ChargerGoGo made the Inc. 5000 this year. If its operators eventually start appearing on that list too, GoGoSpark may have played a part in getting them there.

Discover how GoGoSpark is helping entrepreneurs grow smarter.

📍Website

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Stories

The Day a Las Vegas Slot Machine Changed June Zhu’s Vision for Entrepreneurship

When June Zhu immigrated to the United States, she wasn’t chasing certainty.

She was chasing the possibility.

Like millions of immigrants before her, she believed in something uniquely American: that regardless of where someone came from, if they worked hard, solved real problems, and created value for others, they could build a better future.

That belief led her to found ChargerGoGo.

At first glance, ChargerGoGo looks like a portable phone charging company. Today, its network spans more than 6,000 locations across all 50 states, serving more than one million users.

But ask June what business she’s really building, and her answer is unexpected.

“I’m not trying to just build the biggest charging network,” she says. “I’m trying to build one of the largest entrepreneurship platforms.”

The Question Every Founder Faces

That vision wasn’t obvious in the beginning.

Like countless founders, June spent years trying to answer the same question that keeps entrepreneurs awake at night:

How do you build something nationally without billions of dollars from venture capital?

Every new market required more equipment.

Every new customer required more investment.

Growth always seemed tied to raising more capital.

The Las Vegas Moment

Then one ordinary afternoon in Las Vegas, while talking with her team, she witnessed something that unexpectedly gave her a new perspective.

A few teammates each pulled a small amount of cash from their wallets and decided to play a slot machine together.

Nobody risked very much.

If they lost, the downside was limited to a few hundred dollars each. But if they won, everyone shared in a prize far greater than they could have won individually.

“It wasn’t about the slot machine,” June recalls with a smile. “It was about the ownership.”

She watched people willingly contribute because everyone had a stake in the outcome.

At that moment, the question in her mind changed.

Instead of asking, “How can I raise enough money to own every charging station?”

She started asking, “Why should I own them all?”

What if every charging station could become an income-producing asset for a local entrepreneur?

That idea transformed ChargerGoGo.

Rather than building a company that owned every charging station, June built a platform where local entrepreneurs could own, operate, and grow businesses under a shared brand.

Every charging station became more than hardware. It became an opportunity for someone to build recurring income and grow a business within their own community.

Building an Entrepreneurship Platform

For June, that model reflects something she has admired since arriving in America.

“The greatest strength of this country isn’t just innovation,” she says. “It’s that ordinary people have the opportunity to become builders.”

Instead of measuring success solely by the size of the network, she measures it by how many entrepreneurs it helps create.

Through ChargerGoGo’s distribution partner model, local business owners can build recurring income while expanding the company’s nationwide footprint. As the platform grows, so does the number of entrepreneurs building businesses of their own.

Why Ownership Matters More Than Ever

That belief feels even more relevant as artificial intelligence reshapes the global workforce.

While much of the conversation focuses on jobs disappearing, June believes the more important conversation is about creating more owners.

“The future shouldn’t belong only to companies with the most capital or the most powerful AI,” she says. “Technology should lower the barriers for everyday people to own businesses, generate wealth, and create opportunities for their families.”

That’s why she believes entrepreneurship is becoming more important, not less.

Her vision extends far beyond portable charging.

She imagines a future where platforms, AI, and connected infrastructure allow millions of people to own income-producing businesses that once required millions of dollars to build.

Redefining the American Dream

For June, that’s what the American Dream has always meant.

Not that success is guaranteed.

But that ownership is possible.

Today, when people ask what ChargerGoGo does, she could talk about charging stations, technology, or nationwide expansion.

Instead, she prefers a simpler answer.

“We’re building a platform that helps more people become entrepreneurs.”

Because in the end, June Zhu isn’t trying to build a billion-dollar company.

She’s trying to help build thousands of million-dollar entrepreneurs.

Perhaps that’s the most powerful way to measure success: not by how much one person owns, but by how many owners they help create.

Learn more about ChargerGoGo here:

📍Website

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Stories

How Stephanie Lau Jensen Turned a Personal Identity Journey Into CULTR, a Marketplace for Cultural Brands

Stephanie Lau Jensen grew up between Hawaii and California. Like many Asian American kids raised in predominantly non-Asian communities, she learned early how to move between worlds. Parts of her culture stayed in the background, not because she pushed them away, but because the environment made it easier to leave them there.

She later returned to Hawaii for college, where her father is originally from. Being there placed her in a community where Asian culture was woven into daily life through food, language, and family traditions. It was not a rediscovery, it was a reminder of what had always been hers.

Years later, as a mother of three and a founder with a background in commercial real estate investing, she built CULTR, short for Created for Culture. A curated marketplace for AAPI  and third-culture families raising kids between cultures, one that makes cultural products easy to find and part of everyday life, not just special occasions.

A Birthday Conversation That Changed Everything

The idea for CULTR took shape at one of Stephanie’s birthday gatherings. She was talking with a close friend about identity and culture when a childhood friend overheard the conversation and joked that Stephanie used to be one of them before she moved to Hawaii and really leaned into her Asian side.

Everyone laughed. Stephanie included. But the comment stayed. It put words to something she had been sitting with for years. Culture is not something that automatically transfers to the next generation. It has to be lived daily. If it is not in the house on a regular Tuesday, it probably is not there at all.

When she became a mother and started looking for books, clothing, and toys that reflected her culture, she saw the problem clearly. The products existed. The founders were there, but their work was scattered across small websites and Instagram pages, invisible to most families who needed them.

The Platform She Wished Had Existed

Stephanie’s background in real estate investing trained her to look closely at markets and recognize opportunity gaps. As she continued discovering founder-led cultural brands online, she saw a clear problem: families who wanted these products had no easy way to find them.

That realization led her to build CULTR, a curated marketplace that brings modern cultural brands from around the world into one central destination. The platform highlights independent founders, many from Asian and immigrant communities, whose products carry culture through everyday objects, from children’s books to home goods, apparel, even everyday products you would have never known were made by AAPI makers. With a refined, modern aesthetic, CULTR presents these brands in a way that feels contemporary, approachable, and deeply connected to heritage.

Building CULTR came with its own challenges because the platform did not fit neatly into an existing category. It sits somewhere between a retail marketplace and a cultural storytelling platform, which meant Stephanie had to develop the platform while also helping people understand the vision behind it.

Bringing Culture Into Everyday Family Life

For Stephanie, culture often lives in the smallest everyday objects. A children’s book written in the language your grandparents spoke, a toy tied to tradition, or a piece of clothing that carries a story can shape how the next generation understands identity and belonging.

Alongside CULTR, she is also building PenPals Collective, a project designed to spark global curiosity and connection for children, and launching a podcast called Series M that explores career, motherhood, and identity. Each project reflects her interest in connecting people across culture, family, and generation.

Through each project, and while raising three young children, Stephanie continues working toward the same goal: creating spaces where culture is not something people rediscover later in life, but something families live with every day.

Learn more about CULTR here:

📍Website