Hays and Leah Westbrook of Cloudfit On Why Prioritizing Self-Care Is No Longer Optional for High-Performing Leaders

Hays and Leah Westbrook of Cloudfit On Why Prioritizing Self-Care Is No Longer Optional for High-Performing Leaders

Hays and Leah Westbrook of Cloudfit On Why Prioritizing Self-Care Is No Longer Optional for High-Performing Leaders

An Interview With Jim Hamel


11 min read
·
Jun 11, 2026
Press enter or click to view image in full size

I’d shift the belief that burnout is a sign of ambition. Long-term success comes from sustainability, clarity, and consistency, not constantly running yourself into the ground.

High-performing leaders are expected to be “on” all the time, making decisions under pressure, carrying other people’s stress, and pushing through nonstop demands. For years, many have treated self-care like a luxury, something to get to after the next deadline or the next milestone. But burnout, health breakdowns, strained relationships, and declining focus are catching up with even the most driven executives. What does real self-care look like when you are leading at a high level, and why has it become a requirement rather than a nice-to-have? In this interview series, we are talking to founders, CEOs, executives, coaches, doctors, and anyone who is an authority about “Why Prioritizing Self-Care Is No Longer Optional for High-Performing Leaders”. As part of this series, I had the pleasure of interviewing Hays and Leah Westbrook.

Hays Westbrook is an entrepreneur, real estate professional, and brand builder with more than two decades of experience launching and growing consumer-facing businesses. Over the course of his career, he has combined creativity, marketing expertise, and a strong understanding of lifestyle branding to build ventures that connect with audiences both locally and nationally. In 2003, Hays founded a Nantucket clothing accessories company inspired by the coastal lifestyle of Nantucket Island. The brand quickly gained popularity for its distinctive style and became widely recognized in resort and coastal markets. Over nearly two decades, his Nantucket company grew into a successful lifestyle brand before Hays sold the company in 2022, marking the completion of a long and successful entrepreneurial chapter. In 2007, Hays expanded his entrepreneurial vision by partnering with Cheryl Fudge Fashion Camp on Nantucket Island. The concept was a pioneering experiential retail store that blended fashion, entertainment, and hands-on creativity. The store quickly became a destination for visitors and fashion enthusiasts and eventually expanded nationally. Cheryl Fudge Fashion Camp gained significant media attention and was featured on several reality television programs, helping establish it as a unique cultural phenomenon within experiential retail. The brand also developed a loyal celebrity following, attracting high-profile visitors including Barack Obama and Michelle Obama, members of the Kim Kardashian and Kris Jenner family, Ben Affleck, Kimora Lee Simmons, Chris Martin, Naomi Watts, Reese Witherspoon, and Jennifer Lopez, among many others. Today, Hays brings the same entrepreneurial mindset and strategic thinking to his work in real estate. As an agent with Berkshire Hathaway HomeServices California Properties based in Santa Monica, he advises buyers, sellers, and investors throughout the Westside of Los Angeles. His background in branding, negotiation, and customer experience allows him to approach real estate with a business-minded perspective, helping clients navigate complex transactions while maximizing value. Known for his creative approach and ability to identify opportunities across industries, Hays Westbrook continues to combine entrepreneurship and real estate expertise while pursuing new ventures in lifestyle, retail, and digital commerce with his newest venture, Cloudfit. Leah Agus Westbrook is a seasoned sales professional and entrepreneur whose career spans hospitality, advertising, and business development. Known for her strong client relationships and strategic marketing insight, Leah has built a reputation for helping businesses effectively connect with their audiences. She began her career in the hospitality industry at Domenico’s Italian Restaurant, a beloved institution in Pasadena, where she worked for 16 years. During this time, she developed exceptional customer service and relationship-building skills while gaining firsthand experience in the dynamics of running a successful local business. Leah later transitioned into media and advertising, joining Outfront Media, one of the largest outdoor advertising companies in the United States. Over the next 27 years, she served as an Account Executive in Los Angeles, managing billboard and outdoor advertising campaigns for both local and national brands. Throughout her tenure at Outfront Media, Leah worked closely with companies across a wide range of industries, helping them design and execute strategic advertising campaigns that delivered visibility and impact. Her role required a deep understanding of marketing strategy, audience targeting, and brand positioning, as well as the ability to manage high-level client relationships and large-scale advertising programs. Despite her long and successful corporate career, Leah always maintained an entrepreneurial mindset and a passion for building something of her own. That ambition ultimately led to the creation of Cloudfit, a brand born from her vision to develop a product that combines comfort, functionality, and modern lifestyle design. Cloudfit represents the culmination of Leah’s decades of experience in marketing, sales, and consumer insight. As founder, she brings her expertise in brand development and audience engagement to the company, guiding its growth with the same dedication and strategic perspective that defined her earlier career. Today, Leah Agus Westbrook continues to focus on expanding Cloudfit while applying the lessons she learned from nearly three decades in advertising and client relations. Her career reflects a consistent commitment to innovation, entrepreneurship, and building brands that resonate with people.

Thank you so much for joining us in this interview series! Before we begin, can you please introduce yourself? Our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘Origin Story’ and how you got started?

The idea for Cloudfit was born out of a simple yet frustrating daily chore, making the bed. As busy professionals, we found ourselves constantly grappling with messy, disheveled bedding and the time-consuming task of tidying it up every morning. We quickly realized we weren’t alone; countless others struggled with the same issue. This inspired us to reimagine bedding entirely.

Enter Cloudfit, the world’s first innovative fitted comforter. Our mission was clear: create a comforter that stays in place, eliminates the hassle of bed-making, and still delivers on quality, design, and comfort. After months of research, prototyping, and refining, the Cloudfit fitted comforter was brought to life.

Today, Cloudfit stands as a testament to our commitment to improving life’s little moments. Through Cloudfit, we aim to transform the way people experience their homes, one perfectly made bed at a time.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

Hays: Leah has been my biggest supporter and partner throughout this entire journey. From the earliest idea stages of Cloudfit to building the business together, she’s always brought creativity, perspective, and determination when things got challenging. One moment that stands out was during the product development phase when we were working through countless prototypes and setbacks. Leah kept pushing us forward and helped turn a simple frustration into a real product and brand. I truly wouldn’t be where I am today without her partnership and belief in the vision.

Leah: Absolutely. I’m incredibly grateful for my husband and business partner, Hays. We’ve built Cloudfit together from the ground up, and there were so many moments early on where the idea could have easily stayed just an idea. I remember sitting at home talking about the daily frustration of making beds and wondering why nobody had solved it differently. What started as a simple conversation turned into sketches, prototypes, late nights, and a real shared vision. Having someone who believed in the idea as much as I did and who kept pushing forward through all the uncertainty made all the difference. Building something together as a family has been one of the most rewarding parts of the journey.

Ok, fantastic. Let’s now shift to the main focus of our interview. High-performing leaders are often celebrated for resilience and endurance. At what point did you realize that self-care wasn’t a luxury, but a leadership responsibility?

Hays: I realized self-care was a leadership responsibility the first time I answered a business call while looking for my phone… that was already in my hand. Between startups, real estate, family, and Cloudfit, I learned pretty quickly that running on caffeine and four hours of sleep is not actually a scalable business strategy. At some point you realize if the founder crashes, the whole operation gets a little shaky too.

Leah: I realized pretty quickly that self-care wasn’t a luxury when I started balancing business, family, and the nonstop pace of entrepreneurship all at once. There’s this idea that constantly running on empty means you’re working harder, but I found the opposite to be true. When I’m rested, present, and taking care of myself, I make better decisions, communicate better, and show up as a stronger leader for both my family and our business.

How has prioritizing your own well-being directly impacted your decision-making, company culture, and long-term performance outcomes? Can you share a specific example?

Hays: Prioritizing my well-being has made me a much better decision-maker because it helps me slow down, clear my head, and stay present instead of constantly reacting. One of the biggest things for me is taking our dog on long walks. It gives me time to think without distractions, reset mentally, and often that’s where my best ideas or solutions come from. I’ve noticed that when I’m more centered, I communicate better with our team, make calmer decisions, and create a healthier culture around balance and sustainability instead of burnout. Over the long term, that mindset leads to better performance and clearer leadership.

Leah: Prioritizing my well-being has had a huge impact on how I lead and make decisions. One thing that really helps me stay grounded is baking. It’s something that forces me to slow down, be present, and focus on the process instead of constantly multitasking. Some of my clearest ideas and best decisions have actually come while I’m in the kitchen. I’ve also noticed that when I’m calmer and more balanced, it positively affects the energy around our business and family. It creates a healthier culture where creativity, patience, and sustainability matter just as much as productivity.

What systems, boundaries, or non-negotiable rituals have you implemented to prioritize self-care, and how have those practices evolved as your responsibilities have grown?

Hays: One of the biggest non-negotiables for me is getting enough sleep. Early on, I used to think pushing through exhaustion was part of being an entrepreneur, but I realized pretty quickly that poor sleep affects everything from decision-making, patience, creativity, and overall leadership. As my responsibilities have grown with business and family, I’ve become much more disciplined about protecting my energy and recovery. I’ve learned that being well rested isn’t a luxury, it’s what allows me to consistently show up focused, productive, and present for both my team and my family.

Leah: One of my biggest non-negotiables is trying to avoid screens after 9pm. Running a business and balancing family life can make it easy to feel constantly connected, so creating that boundary helps me mentally slow down and be more present. I also pray the rosary regularly, which has become an important way for me to reset, reflect, and find peace in the middle of busy seasons. As my responsibilities have grown, I’ve realized that protecting quiet time and creating intentional routines isn’t selfish, it’s necessary for staying grounded, focused, and able to lead well over the long term.

If you could shift one belief that high-achieving executives hold about burnout, productivity, or balance, what would it be and why?

Hays: I’d shift the belief that burnout is a sign of ambition. Long-term success comes from sustainability, clarity, and consistency, not constantly running yourself into the ground.

Get Jim Hamel’s stories in your inbox

Join Medium for free to get updates from this writer.

Remember me for faster sign in

Leah: I think a lot of high achievers confuse being busy with being productive. Some of the best decisions and ideas come when you slow down enough to actually think clearly and be present.

Press enter or click to view image in full size

Please share your “Five self-care routines you need in order to succeed and thrive as a high-performing leader”. If you can, please share a story or an example for each.

1. Making the Bed

It sounds simple, but making the bed helps us start the day feeling organized and productive. Ironically, creating Cloudfit came from being frustrated with making beds in the first place. Now it’s become a small daily reset that makes the whole room, and our daily mindset, feel calmer.

2. Long walks with our dog

Some of my best ideas happen while walking the dog. There’s something about getting outside without staring at a screen that clears our head. We’ve solved countless business problems while picking up tennis balls at the park.

3. Baking

Baking forces us to be patient and present. You can’t rush bread or cookies, no matter how many emails you have waiting. It’s one of the few times we can fully unplug and focus on something creative just for fun.

4. Getting enough sleep

We used to think functioning on very little sleep was impressive. Then we realized we were forgetting simple things like where we left our coffee or keys, while holding it. In the craziness of running a startup, we treat sleep like it’s a non-negotiable part of our workday.

5. Praying the rosary

The rosary has become a grounding ritual for me. It helps quiet the constant mental noise and gives me a moment to reflect, reset, and put things into perspective during stressful seasons.

You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. :-)

Hays: I’d love to start a movement focused on making everyday life easier and less stressful for families. Small innovations or habits can have a surprisingly big impact on people’s happiness and well-being. You never know how one simple idea can improve someone’s daily routine, mindset, or quality of life.

Leah: I’d start a movement around slowing down and being more present with the people we love. I think so many people are overwhelmed, distracted, and constantly rushing through life. Sometimes the greatest impact comes from simple things, family dinners, meaningful conversations, putting the phone away, or even making the bed and creating a calmer home environment.

How can our readers further follow your work online?

https://www.gocloudfit.com/

https://www.instagram.com/gocloudfit/

https://www.facebook.com/Cloudfitcomforters/

https://www.tiktok.com/@gocloudfit

https://www.youtube.com/@GoCloudfit

This was very inspiring. Thank you so much for the time you spent with this!

Back to blog