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

From Vancouver to the World: Thomas Vu’s Vision for Hanoi Drip Coffee

Vietnam is one of the world’s biggest coffee-producing countries, yet Thomas Vu rarely saw Vietnamese coffee given the same attention in North America’s specialty coffee scene.

That gap became the idea behind Hanoi Drip Coffee, a Vancouver-based Vietnamese specialty coffee brand that has grown into a multi-million-dollar cafe business in just over two years.

For Vu, the goal goes beyond opening more cafes. He wants people to see Vietnamese coffee differently and prove that a brand deeply rooted in culture can belong on a global stage.

Giving Vietnamese Coffee the Spotlight It Deserves

Vu grew up around the flavors and rituals that make Vietnamese coffee instantly recognizable, from strong Robusta to condensed milk and the slow drip of a phin. Yet despite Vietnam’s rich coffee history, he felt much of that story was still missing from mainstream specialty coffee culture.

That became the opportunity behind Hanoi Drip. Rather than recreate a traditional Vietnamese cafe, Vu and his team asked a bigger question: What could a global Vietnamese coffee brand look like today?

Their answer was to keep the parts of Vietnamese coffee they loved while presenting them for a new generation. Hanoi Drip serves coffee grown in Vietnam, including coffee from Đà Lạt, and puts Robusta, Vietnamese flavors, and phin brewing at the center of the experience.

Learning How to Grow Without Losing the Brand

Building the brand was one challenge. Learning how to grow it without losing what people connected with was another.

When Hanoi Drip was smaller, Vu and the other founders could be involved in nearly every part of the business. As more locations followed, they had to learn how to train teams, develop leaders, manage costs, maintain product consistency, and make sure customers still had a strong experience even when the founders were not there.

Mistakes have been part of that process, and Vu does not pretend otherwise. His approach is to treat them as useful information: fix the problem, build a better system, and move forward, a mindset that has helped Hanoi Drip expand into multiple locations alongside retail coffee, wholesale, and membership offerings.

Taking Vietnamese Coffee Beyond Vancouver

For Vu, some of Hanoi Drip’s most meaningful wins happen when someone tastes Vietnamese coffee for the first time and wants to know more. It also means hearing Vietnamese customers say the brand reminds them of home while still feeling like it belongs to their generation.

That connection has extended beyond coffee. During KOOLFEST 2025, customers purchased more than 1,600 Ube Coconut Coffee and Ube Milk drinks, helping Hanoi Drip raise over $5,500 for a local charity, while the company has also created jobs and collaborated with Asian-owned businesses and creators.

And Vu is still thinking much bigger. He hopes to bring Hanoi Drip beyond Vancouver to markets such as Toronto and Los Angeles, while showing other Asian founders that building something modern does not mean leaving their culture behind.

Learn more about Hanoi Drip and follow the brand as it works to take Vietnamese coffee from Vancouver to a wider global audience.

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Stories

From a $10 Craigslist Job to COO of a $300M Business Group: Richard Nguyen’s Road to E-XPIRE

Richard Nguyen grew up on the east side of San Jose, where he became caught up in street life at a young age. Looking back, he believed the path he was on could have ended with either prison or an early death.

Then came the moment that made him reconsider where his life was headed.

He overheard his mother speaking with friends about their children. She talked about relatives who had graduated from college, while Richard felt she had little she could proudly say about him.

“She couldn’t say anything good about me,” Richard recalled.

His mother was raising the family on her own, and hearing her disappointment became a wake-up call. Richard knew he couldn’t continue down the same path and decided he needed to find a different direction.

He took a job he found on Craigslist for $10 an hour, unsure of where it would lead. It became his entry point into an industry where he would spend the next 15 years learning and building experience.

What started as a decision to change his life would eventually become the foundation for something much bigger.

Years later, that experience would bring him together with Jack and David Nguyen and a growing group of IT hardware businesses.

Twin brothers Jack and David Nguyen

The Brothers Behind the Business

Years before Richard partnered with them, twin brothers Jack and David Nguyen were already building their footprint in the IT hardware industry.

Around two decades ago, they saw an opportunity in used computer equipment and began reselling components, primarily semiconductors and RAM. That business became RAM Exchange, which eventually grew into what Jack described as a $50 million-a-year company.

From there, the brothers expanded into servers, networking equipment, drives, and other data center hardware through IT Server Exchange.

By then, Richard had spent years building his own expertise in the same industry. Their paths were about to come together.

Bringing Richard Into the Business

Richard was working for a competitor at the time, but his experience and reputation had already caught Jack and David’s attention. They knew his understanding of the IT hardware business and respected the grit, loyalty, and work ethic he brought to his work.

Eventually, Richard took a risk of his own and started E-XPIRE, focusing on IT asset disposition, secure data destruction, and electronics recycling.

As E-XPIRE grew, Jack and David saw more than Richard’s industry experience. They saw someone who could build a business, lead a team, and execute.

But Richard had already taken the risk of becoming an entrepreneur himself. Bringing him into their business would require more than offering him a position.

The opportunity became a partnership. E-XPIRE and IT Server Exchange merged, bringing Richard’s ITAD expertise together with Jack and David’s established hardware business. Richard became an equal partner in IT Server Exchange and took on the role of COO.

“We gave him the keys,” Jack said.

The merger brought together two complementary sides of the industry and created an opportunity to build something larger. Richard came in ready to rethink how the operation worked, and Jack and David gave him the freedom to make the changes he believed the business needed.

Their roles complemented each other. Richard took the lead on operations, execution, and building the team, while Jack and David provided the business foundation, resources, and support behind him. Jack described himself and David as Richard’s “pillars.”

Together, they continued growing RAM Exchange, IT Server Exchange, and E-XPIRE. Today, the partners say the three companies are on track for around $300 million in combined annual revenue.

What began with Richard taking a chance on himself and building E-XPIRE ultimately became the start of a partnership that would help reshape IT Server Exchange and support the growth of the wider business group.

Leading Through Culture

For Richard, how the team works is just as important as how the business grows.

He describes a culture built around speed, loyalty, and getting things done. Internally, the team uses the phrase “GSD,” short for “get stuff done.”

Richard also sees his employees’ livelihoods as a personal responsibility.

“I work 18-hour days because it’s for my team and my family,” he said.

David credits Richard with creating a culture where employees feel that same sense of loyalty toward the company.

That philosophy is shared by all three partners. Jack said one of their biggest sources of pride is not simply revenue growth, but the impact their businesses have had on employees and their families.

Finding a Reason to Keep Going

For Richard, success still traces back to the conversation he overheard more than two decades ago.

Today, David says Richard’s mother lights up when she talks about him.

“Every time I see her, she smiles,” he said. “She’s so proud of Richard.”

Richard’s advice for people who feel the odds are against them is simple.

“Anyone can make it,” he said. “You just gotta find a reason to do it.”

More than two decades after that conversation, Richard has given his mother plenty to be proud of. That same drive now carries into the work Richard, Jack, and David are building at E-XPIRE.

While companies race to adapt to AI, Jack, David, and Richard focus on what powers it: infrastructure. Their businesses support its lifecycle, from hardware to responsible decommissioning.

Today, E-XPIRE helps businesses securely destroy sensitive data and responsibly manage retired IT equipment. As technology continues to evolve, so does the need to handle what gets left behind.

Learn more about E-XPIRE and its work in IT asset disposition, data destruction, and electronics recycling.

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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.

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