Navigating Pivots and Perseverance: Wei's Journey with Clipboard Health

Awaken* newsletter

July 18, 2024

Wei Deng is the Co-Founder and CEO of Clipboard Health, a company that connects healthcare facilities with local professionals who can work unfilled shifts. Since Clipboard’s inception in 2016, Clipboard Health has filled millions of shifts for thousands of facilities nationwide, putting millions of dollars in the pockets of healthcare professionals. Throughout her journey, Wei has never lost sight of her ultimate mission of helping people socioeconomically. In this interview with AHN, she discusses her upbringing and the early days of her founder’s journey.

HanYue: Tell us about the early days of Clipboard Health, what type of challenges did you have to overcome?

Wei: It wasn’t called Clipboard Health when I started. It was initially a way to refinance student loans. I spent time talking to customers, figuring out who wanted to buy the fintech products, and talking to different customers again but I just didn’t feel the pull of the market, but I noticed that nurses wanted help finding a job. However, the hospitals only wanted to help people with experiences. So I pivoted to a clinical fellowship to help train nurses, figuring out what the clinical partners need, and help nurses find jobs.

After pivoting through 6-7 different ideas – I finally landed on the Clipboard Health model, a marketplace that helps with nurse staffing. In the early days, we were very much focused on launching a product and talking to users.

Edwin: How do you judge when to pivot and when to stop working on an idea?

Wei: I wish there was a magic formula – but there isn’t. Having seen some other friends who have found PMF was helpful. For our products, our customers could live with it or without it. They didn’t have any strong opinions about it. That was a sign to me that it’s not working. For most ideas, I gave it to 3-6 months. What was frustrating is that sometimes you would have some initial glimmer of hope – some people are using it, and you wonder to yourself, is that a real sign?

For a good product, I found out that even if the product isn’t built out, people still want to use it, and people care about it a lot. You can feel the pull of the market.

HanYue: There is clearly an unrelenting drive to pursue entrepreneurship, what kept you going during the early days?

Wei: Quitting just never occurred to me. In the beginning, I mostly called the things I worked on projects, and when they didn’t work out, I just never gave up.

Of course, there were frustrating moments: when I first went fundraising, I got told no 16 times. I was a solo founder, so there was no one to help me. I taught myself coding and sales to get started. I think the big realization is that even if you encounter nos and the product is not working, as long as you keep working and don’t quit, you are getting closer to a yes.

HanYue: That was really inspiring – as long as you keep working, you are getting closer to a yes. Want to switch gears a little bit, how did you meet your co-founder? What was it like building out the initial team?

Wei: In the early days, it was just me. My husband joined me after 3 years. By that time we already raised Series A, we were growing and had some traction. He initially joined to help out for 3 months, then stayed on for a few years.

Building out the team, we had a lot of trials and errors. We definitely made some mistakes – I had engineers whom you couldn’t get ahold of even when I was trying to fire them. We had one head of sales who built out our sales team but it turned out he was working for a competitor at the same time and was giving them our customer list, and all the people who worked for him were also working for the competitor. But luckily, some good people stayed and really they are what made us successful.

HanYue: Tell us about the people who stayed. What made them successful?

Wei: Oh, I love talking about this because it is what we look for during hiring. They have to care about the problem a lot. It is actually very obvious whether people are just here to collect paychecks, going through the motions, or if they really care about the problem.

They are really curious. They are always looking for clues. If a customer says no, or churns, they are always digging in and figuring out why, instead of taking it as a given – oh they just didn’t want to use the product.

They also have ownership and initiative. They never just bring a list of problems. The best people I’ve had, they’ve brought me problems I didn’t know we had, and they’ve already thought about how to solve them.

So initiative, ownership, and curiosity are our people and company values.

HanYue: That’s wonderful to hear that there is such a close alignment between the people’s values and company values. What was your proudest achievement so far?

Wei: Honestly, I think it’s assembling a great team. We’ve gone through a lot of great pains in hiring, but now we have an awesome team to move together. Nowadays, even if I pull my foot off the gas, they are still serving our customers the best they can, and that is very special.

The second thing is the customers we’ve been able to help, but that is honestly more of a proxy of how great our team is.

HanYue: Tell us a bit about your upbringing. How has being Asian influenced your entrepreneurship journey and your general approach to life?

Wei: I grew up with my mom and my dad. We grew up in Kentucky, there were not a lot of Asians in Kentucky.

My dad had this mentality: you don’t need permission to learn something. I remember trying to go to a national science fair – I was 16 and needed to learn calculus, but calculus was a college-level class and I was thinking, “Oh, maybe I can’t because I had to wait to learn calculus later.” My dad just said, get a textbook and figure it out yourself. That’s something I carried forward in life.

When I started, I didn’t have to have someone who knew how to code, I could just learn coding myself and get started. I never did sales before and didn’t have someone I could rely on for sales, but I could just pick up a phone and start doing cold calls. It’s the sense that nothing is beyond my reach, you don’t need to wait for the perfect moment or something/someone to depend on to get started.

There weren’t many Asians in the area I was from. We stuck together but we were also super competitive with each other. There were two people in high school I was constantly competing against, and I think in a lot of ways it brought out the best in me. Personally, I am not competitive, but I found having someone neck-to-neck with you really makes me thrive.

HanYue: Congrats on the unicorn status – it’s an incredible achievement! What suggestion do you have for founders who are still searching for product market fit out there?

The only thing that matters is to understand the customer’s pain points deeper than anything else. Rather than spending time on solutions, spend more time on understanding the problem. Actually, you might find that you are not even starting with the right customers – you might have to pivot a few times to find the right customers.

When you find them – look at their habits. People who are saying they want to lose weight, but if they are not going to the gym or tracking their calories or metrics, then weight loss is just not that big of a deal to them.

When talking to them, you need to look for: Are they spending money on it? Are they spending a lot of money but still can’t solve the problem? That is a potential area you can go to. The chances are that you can find a lot of good solutions – you can have the greatest AI and greatest product, but if it is not solving a real problem, then no one will end up paying for the solution.

Edwin: Are there mechanisms and processes you use to tease this information out?

Wei: We just look at their behaviors. Are they spending money? Is the pain point really painful?

When it came to staffing, it was obvious, that the customers we talked to were spending all of this money to putting together spreadsheets and tracking attendance. It was clearly a big pain point they wanted to solve.

My father passed last year, I remember spending so much time looking for a caregiver for him. If someone gave me a set of solutions, even if not super built out – just a list of caregivers or a list of places that could care for him, I would definitely want to talk to that person.

HanYue: Thanks for sharing a deeply personal moment with us. It really makes sense that as founders we needed to find the most painful problem to solve. Where do you go from here? What’s next for Clipboard Health?

Wei: Personally, I have two kids and I spend a lot of time with them. For the company, we want to continue expanding beyond healthcare professionals. We started with nursing – but we wanted to allow workers of all industries the benefits of flexibility and economic empowerment.

At Clipboard Health, we also have an internal MBA-like program. If you are a product manager but want to learn, we will teach you cross-functional skills – engineering, sales, and other things.

The hypothesis is that eventually if people leave and want to go and start their own company, I could enable them to have a much broader scope than just their own focus. We have engineers doing sales, customer support, and product and they all love it because they get to implement and continue to broaden their scope. One of our heads of sales was a product manager – they kept asking questions and wanted to learn about sales so they got the chance to lean into their curiosity.

I want to scale this program up as the company scales up to develop people. Because if you invest in people internally, what you get is phenomenal: People who are already invested in your culture, and know your product really well have more methods to help your customers and grow better.

Edwin: I see some parallels to your journey as well – the early days when you had to teach yourself coding and sales. One thing you talked about is expanding to verticals, how are you finding the new verticals?

Wei: We have a more systematic approach: we read the Bureau of Labor Statistics, and try to look at professions that need help. Maybe some professions are losing steam, etc. We also have lots of customers in healthcare and there is a a surprising number of professions to fill up there – we need janitors to clean up, cooks to cook for the dining hall, servers and waiters, and trainers for physical therapy patients. There are some natural adjacent areas. Customers are providing those insights to us and where they need help.

Edwin: Are you afraid of losing focus?

Wei: Focus is overrated, You should try to be good at some core competencies – but it all depends on how you define your core. if we define our core as a flexible labor marketplace, then we have lots of room to build.

If you look at any ambitious company, they have a ton of products and they might seem totally unorthodox to each other. Amazing doesn’t look focused: they have AWS and it has nothing to do with selling books. Or if you think of people around you, some of them are good at maths, instruments and some type of sports. No one is like: you should only be good at math – people develop expertise in multiple areas.

There is certainly a concern about chasing shiny new projects. We try to only pursue things that we have pre-thought out and really ask ourselves – do we want to be more ambitious than we currently are, or are we just chasing a shiny new object?

Wei’s journey with Clipboard Health underscores the importance of persistence, adaptability, and deep customer understanding. Her story is a testament to the power of resilience in entrepreneurship, demonstrating that with unwavering determination and a keen focus on solving real problems, success is within reach. The AHN team thanks Wei for having this conversation with us!

Stories

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

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

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

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

From Film Sets to Daily Habits

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

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

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

Nathan Yun (right), Founder of Paire

Learning How to Build Before Building His Own

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

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

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

Nathan Yun (far right), Founder of Paire

The Trip That Made the Mission Personal

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

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

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

Nathan Yun (left), Founder of Paire

Earning Trust Through the Product Itself

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

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

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

Follow Nathan’s journey:

📍 Website
📍 Instagram | LinkedIn

Dec 19, 2025
4 min read

Blogs, Development

What the Creator Economy Really Needs in 2026

The creator economy is no longer a niche corner of the internet. It is a $250 billion industry, powering modern marketing, culture, and commerce. Yet for the creators at its core, the experience often remains unstable and fragmented. Inconsistent rates, shifting platform demands, and “gifting” budgets paired with outsized expectations have left many navigating an ecosystem that hasn’t caught up to their value.

As we look toward 2026, the industry is approaching a tipping point. Growth alone is no longer enough. What creators need now are standards, systems, and support that allow them to build sustainable careers—not just viral moments.

Below are five critical shifts shaping the future of creator work, and the standards Meraki is building to support a stronger, more intentional industry.

1. Stronger Structure for a Growing Industry

Photo courtesy of Vivian Kwan (center), Founder of Meraki Group

While creator content has never been more polished, the backend of the industry remains disorganized. Uneven pay scales, scope creep mid-campaign, and unclear paths to professional growth are still common. Creators are often met with constant brief changes or “gifting” requests that require high-level deliverables without fair compensation.

The gap: There is no shared structure defining fair rates, clear deliverables, or realistic timelines across the industry. Expectations are often implied rather than stated, leaving creators to absorb last-minute changes, unpaid revisions, and expanded usage. Over time, this places most of the financial and emotional risk on creators instead of being shared evenly with brand partners.

The Meraki solution: Meraki builds every partnership on clarity. Terms and rates are established upfront, expectations are clearly defined, and communication stays transparent throughout the process. By setting strong boundaries early, creators are protected from underpayment, and brands begin each project with a shared roadmap for success.

2. Education That Powers Careers, Not Just Content

Image Source: Pexels

The biggest challenges creators face are rarely creative. They are structural. Pricing work correctly, understanding usage rights, and identifying harmful contract clauses remain major pain points—even for experienced creators.

Too often, creators are expected to learn these lessons the hard way.

The gap: Most creators enter the industry without access to professional guidance that supports long-term career growth. Knowledge around contracts, licensing, and negotiation is often gatekept or learned through costly mistakes. As a result, many creators stay stuck in short-term cycles instead of building sustainable paths forward.

The Meraki solution: Meraki focuses on training ethical, creator-first managers who act as true career partners. Through negotiation support and education around contract red flags, creators are equipped to think beyond the next deal and toward sustainable, multi-year growth.

3. Standards in Negotiation and Contracts

Image Source: Pexels

A significant number of creators still undercharge for their work, and 26% report needing help navigating contracts. Without standardized deal benchmarks, creators are often left guessing their worth—leading to pay gaps, rights misuse, and legal risk.

The gap: Negotiation norms vary widely, with no clear benchmarks for fair compensation or usage terms. Many contracts are written in dense legal language that creators are expected to sign without full understanding. This imbalance leaves creators vulnerable to losing control of their work and long-term earning potential.

The Meraki solution: Meraki empowers creators with defined negotiation standards and the confidence to secure fair, market-value deals. By demystifying contracts and usage terms, creators can focus on their craft knowing their income and intellectual property are protected.

4. Work Models That Protect Wellbeing

Image Source: Pexels

Burnout has become one of the industry’s most pressing issues, affecting more than half of full-time creators. The always-on model—driven by algorithm shifts and last-minute deadlines—is no longer sustainable.

Creativity cannot thrive under constant urgency.

The gap: Many campaigns are built around speed and volume rather than realistic creative timelines. Creators are expected to be constantly available, adapt instantly, and produce under pressure without recovery time. Over time, this erodes both creative quality and mental health.

The Meraki solution: Meraki advocates for structured planning and sustainable workflows. Campaign timelines are built to protect both creative quality and mental health, proving that high-level output does not require constant exhaustion.

5. Representation Rooted in Voice, Not Trends

Image Source: Pexels

Creators are increasingly resistant to being reduced to labels or treated as trend-driven checkboxes. True representation starts with understanding a creator’s voice—not forcing them into a predefined brand narrative.

The gap: Many partnerships remain transactional, prioritizing short-term relevance over genuine alignment. Creators are often selected to fill a category rather than for their perspective or long-term vision. This leads to inauthentic work that disconnects creators from their communities.

The Meraki solution: Meraki begins every partnership by listening. By understanding each creator’s goals and vision, Meraki aligns them with brands that share their values—fostering long-term relationships that feel authentic to both the creator and their community.

Photo courtesy of Vivian Kwan (second from left), Founder of Meraki Group

The Next Era: Purpose Over Pressure

As we look toward 2026, the transition from a “Wild West” to a professionalized industry requires more than just better tools—it requires a fundamental shift in how we value the humans behind the content.

Meraki sits at the center of this new era, bridging creative passion with real professional growth. By pushing for fair standards, ethical representation, and sustainable careers, Meraki does more than manage creators; they help protect the future of creative work.wi

Learn more about Meraki Group:

📍Website

📍Instagram

Dec 19, 2025
5 min read

Stories

Joeydolls by Samantha Ong: A Story of a Daughter’s Search and a Mother’s Mission

Where Identity Begins

Growing up in Australia as part of a small minority shaped Samantha’s early understanding of identity. It taught her what it feels like to search for belonging, to look for pieces of yourself in the world and not always find them. Those early lessons sat quietly in the background as she moved into adulthood.

Her career began in finance, a path she chose for its stability and predictability. But creativity eventually led her in a different direction. She built a thriving wedding photography studio—one that grew from passion, long nights, and the joy of capturing love stories. It was a life she couldn’t have imagined at the start.

Then the pandemic arrived. Overnight, hundreds of thousands of bookings vanished. The business she had spent years building collapsed in an instant. And in that same period of loss, another reality weighed heavily on her: the rise in anti-Asian hate. As a mother, the headlines and the stories hit differently. Samantha began thinking deeply about the world she wanted for her daughters—what they would grow up seeing, feeling, and believing about themselves.

That led her on a simple search: dolls that reflected her daughters’ culture. But what she found were options that were limited, stereotypical, and often too expensive. It was a moment that crystallized something important. Realizing how quickly children learn about who they are, the idea for Joeydolls began to take shape—quietly, but powerfully.

Turning an Idea Into a Brand

An idea, however, is only the beginning. Turning it into a real toy brand meant stepping into a world Samantha knew nothing about. She had to learn everything from manufacturing to product design to e-commerce—starting from zero. There was no roadmap, just persistence and a mission that felt too important to abandon.

The timing made it even harder. Pandemic rules slowed communication. Shipping delays stretched out timelines from weeks to months. With very little funding, every decision mattered. Every misstep cost time she couldn’t afford to lose.

Then tariffs on goods from China jumped to 145%, and suddenly even the future of the business came into question. There were moments when it all seemed impossible—too expensive, too complex, too overwhelming for one person to navigate.

But Samantha kept going. She kept refining the vision, pushing through setbacks, and holding onto the mission that started it all. And she didn’t do it alone. Throughout the long nights and the uncertainty, she was supported by a husband working multiple jobs so she could stay focused on building the brand their daughters—and so many other children—deserved.

A Brand With a Bigger Purpose

Today, Joeydolls has sold over 15,000 dolls and earned major recognition. But those numbers only tell part of the story. At its heart, the brand is Samantha’s answer to a question that began during one of the hardest moments of her life: How do we help children grow up seeing their cultures celebrated, not erased?

Joeydolls stands as that answer—a way for children to see their cultures reflected with pride, dignity, and everyday joy. What started as a search for her own daughters became a mission to help thousands of children feel seen, valued, and connected to where they come from.

A single doll can seem small. But for many families, it’s a beginning. And for Samantha, it’s proof that representation—when created with care—can grow into something far bigger than one person’s story.

Learn more about her story here: https://www.joeydolls.com/

Dec 8, 2025
3 min read

Stories

Lucy Liu Stars in “Rosemead,” a True Story of Immigrant Mothers Facing Fear and Mental Health Challenges

Lucy Liu is once again bringing us a powerful performance with Rosemead, a film that has been picked up by Vertical for a December theatrical release. The story follows a mother who begins to see troubling changes in her teenage son, opening the door to a deeper look at fear, love, and mental health.

Recently, the film gathered strong early interest after drawing a full audience at a special screening held at the Metreon in San Francisco. Hosted by Dave Lu, the event sparked conversations about topics often avoided in public spaces, especially within immigrant communities.

With its growing list of festival honors, positive reviews, and a narrative inspired by real events, Rosemead is already being recognized as one of Liu’s most powerful and personal performances to date.

Image Source: BBC

A Story Built on Fear and Family Pressure

At the heart of Rosemead is a mother who becomes concerned as her son’s behavior shifts in unsettling ways. What begins as quiet anxiety slowly grows into a frightening urgency as she realizes the situation may be more dangerous than she imagined.

As her fear rises, she faces the painful question of how far a parent can go to protect the child they love. The tension builds with each scene, making her inner struggle feel both real and universal.

The story takes place within a Chinese American household where cultural expectations and unspoken worries create additional layers of pressure. Lucy Liu captures these emotions with precision, while newcomer Lawrence Shou brings a raw, unpredictable intensity that deepens the film’s emotional impact.

Image Source: The Traveler’s Take

Building Momentum Through Festival Wins

Before reaching theaters, Rosemead had already made a strong impression on the festival circuit. Its premiere at Tribeca drew praise for its gripping approach to storytelling and its standout performances.

The film’s momentum continued as it won Best Narrative Feature at the Bentonville Film Festival, adding to its early recognition. It gained even more attention after earning the Prix du Public UBS audience award at the Locarno Film Festival.

During its time at Locarno, Lucy Liu also received a Career Achievement Award that highlighted her long-standing influence in the industry. Vertical’s Peter Jarowey praised her work for its emotional depth, while also recognizing director Eric Lin’s bold and confident vision in his feature debut.

Image Source: Yahoo

A Strong Screening at the San Francisco Metreon

The event at the Metreon brought together creators, film lovers, and local community members for an open discussion about the upcoming release. The gathering served as a space for people to share expectations, explore the film’s themes, and talk about the real-life issues it aims to portray.

The audience noted how the film reflects real family struggles, especially those found in immigrant households. Its grounded approach to fear and uncertainty sparked discussions about mental health and cultural expectations.

After the screening, conversations centered on Liu’s controlled yet deeply affecting performance. Lawrence Shou also drew attention for his breakout role, adding to the anticipation for the film’s one-week run in selected theaters this December.

Experience the film in theaters and see why it’s already drawing strong early interest. Rosemead is set to premiere in select theaters on December 5, 2025 in New York City; December 12, 2025 in Los Angeles, and more cities to follow on January 9, 2026.

Image Source: Nikolas Liepens

Nov 25, 2025
4 min read

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

What the Creator Economy Really Needs in 2026

1. Stronger Structure for a Growing Industry

Photo courtesy of Vivian Kwan (center), Founder of Meraki Group

2. Education That Powers Careers, Not Just Content

Image Source: Pexels