Meet Wing Pepper: Entrepreneur-in-Residence

Wing Pepper is curious and unafraid to take on a challenge that makes healthcare better. We caught up with him recently to learn more about what inspires him, what he's most curious about and what he's been up to since he joined the Healthworx team. 


Q: What inspires you in your work?

A: Three things inspire me in my work:

  • Mission and Purpose: Sometimes, easier said than done, but I need to have purpose in everything I do. Is my work helping other people? Am I contributing to solving a big problem? Am I making the world a better place for my kids? This can be hard because in our day-to-day work one can’t always draw a direct line between task and purpose. I try to take about an hour per week to make a list and connect my tactical work to bigger challenges. At Healthworx, for example, I’ll frequently ask myself if my deliverables for this week are helping make healthcare more affordable or easier to access or helping those in need. Honestly, sometimes it isn’t, but by consistently asking the question, I find I can strategically reorient my work so that most of the time I can feel like what I do makes a difference.

  • New ways to solve old problems: I am curious to a fault.  Seeing an opportunity to right a wrong, fix a system or invent a new approach to solve challenges inspires me to no end. And the bigger the hill to climb, the better. Sometimes we’ll miss the trees when we’re focused on the forest, but as an entrepreneur, I’m torn (or inspired) by seeing big strategic opportunities then working backwards to see how that might be solved in some new, unusual way.  

  • Collaborating with thoughtful people. When I was younger, I thought I had to know the answers to be taken seriously. As I became more experienced and humbled, I realized my real job was to find the answers. Finding the answers often requires collaborating. I am super inspired by meeting and working with interesting people. Building networks of people from different economic strata, cultures, professions, and ages is essential to getting good advice and guidance on almost any opportunity that arises.  


Q: When it comes to the future of healthcare, what are you curious about?

A: As someone who has been in the digital business, and as an entrepreneur, I tend to focus on how digital platforms can transform the way we seek, receive and manage care. I’m curious about how fast we can move healthcare into the home, the future of digital therapeutics, the systems that put the patient back at the center of the care ecosystem and how government can play a productive role in the healthcare ecosystem.

Like most other industries, healthcare is going through a digital revolution, albeit somewhat later than other less regulated industries. If you think about the car business, for example, twenty years ago the idea of researching a car purchase on the internet was just taking root and it was impossible to purchase a car on the internet – you had to go to a dealer. Now, you can buy a car on your phone and have it delivered to your house within 24 hours. And, your car will download new software independently as the manufacturer updates the software without you ever needing to know.  It took time for this change to happen and brave people to buck the system…but it can happen.

I remember when I was working at a digital agency back in the early days of the web. A client from a major airline looked at me and said, “Son, I can promise you one thing. No one is ever, ever going to buy an airline ticket off the internet.”


My agency then built the platform that sold the first airline ticket on the internet….

So, what gets me excited about the future of healthcare is imagining these new systems and processes to deliver better services in new ways that disrupt the status quo – for all our benefits. Then, shrug off the naysayers and make it happen.

Q: What are you working on that you’re excited about?

A: I am a doer by nature. I work as an entrepreneur in residence within Healthworx. I am exploring a variety of new services and products that can address the issues above. I get really excited not just thinking about ideas but building them. We get to test and learn how we can create new solutions and businesses that open new treatment options for patients while expanding our ability to make an impact in the marketplace.

Q: How can someone best connect with you?  

A: People can reach me at  I am always game to meet virtually or in person, preferably with some paper, so we can draw up the next cool idea.


Healthworx seeks, nurtures, and builds the solutions that are changing healthcare.  We are a team of leaders who pursue their curiosity. We bravely embrace challenges and actively practice empathy. We drive forward with a bias for action and collaborate to unleash the power of collective thinking. Why are we committed to these values? To deliver the transformative results required to improve the way healthcare works for all. If you’re looking for your next career move and our values resonate with you, then connect with us. You can learn more about our open opportunities here. Please note, the link will take you to an external career website.