Alright – so today we’ve got the honor of introducing you to Kim Riera. We think you’ll enjoy our conversation, we’ve shared it below.

Kim , thanks for taking the time to share your stories with us today Do you take vacations? How do you keep things going – any advice for entrepreneurs who feel like they can’t step away from their business for a short vacation?

As someone who runs a vacation rental business, you’d think I’d be the first to take a getaway. But in the early days, I was glued to my phone—answering inquiries at midnight, troubleshooting Wi-Fi issues from a dinner table, and checking reservation calendars like my life depended on it. The irony wasn’t lost on me: I was creating beautiful escapes for other people while feeling like I couldn’t take one myself.

Eventually, I realized that always being “on” wasn’t sustainable—and it certainly wasn’t why I became an entrepreneur in the first place. So I made a shift. I built systems, automated what I could, and surrounded myself with trusted local partners. I created checklists, templates, and plans that didn’t require me to be in the driver’s seat every single day.

And it paid off. This past year, I was able to step away with my family and travel to Argentina. We explored vineyards in Mendoza, hiked the Andes Mountains, soaked in new experiences, and spent uninterrupted time together—no phones, no inboxes, no last-minute guest messages. It was the kind of trip I used to dream about, and now I had built a business that made it possible.

That trip was a milestone, but the same mindset allows us to enjoy smaller, more frequent escapes too—quick weekends in the Adirondacks, hikes and lake time in the Finger Lakes, even day trips or overnights in NYC. These short breaks help us stay connected as a family, recharge, and enjoy the kind of freedom that inspired me to start this business in the first place.

More than anything, these moments remind me why balance matters. As a parent, I want to be a good role model for my kids—not just in ambition, but in presence. I want them to see that you can work hard and still make time for joy, adventure, and connection. That success isn’t measured only in productivity, but in the life you get to live because of it.

My advice for fellow entrepreneurs—especially those in hospitality who feel like they can’t step away—is this: build a business that supports your life, not the other way around. With planning, trust, and intention, it’s possible to take a deep breath, stretch your legs, and enjoy the kind of moments you’re working so hard to create for others—and for your own family, too.

Kim , before we move on to more of these sorts of questions, can you take some time to bring our readers up to speed on you and what you do?

Meet the Entrepreneur: From Organizing Closets to Curating Escapes

Hi! I’m the founder of Stay Catskills, a vacation rental business built with heart, intention, and a deep love for the Catskills. The idea for this business came to me during a quiet but pivotal moment—when my youngest child was about to start school. Like many parents at that stage, I found myself asking, What’s next for me?

At first, I considered starting a professional organizing business. I’ve always loved creating beautiful, functional spaces, and organizing felt like a natural fit. But after mapping out a business plan, I realized that my ideal client—second homeowners—probably weren’t looking to hire an organizer for their vacation homes.

Then someone asked me if I knew anyone who could clean their vacation property. That one question flipped a switch. I realized that by helping care for these homes, I could learn exactly what second homeowners needed—how they used their homes, what challenges they faced, and what made their escapes feel seamless. Around the same time, Airbnb was going mainstream, and I saw an opportunity to offer something more thoughtful and personal—rooted in my love for the area and my excitement to share it.

That was nearly ten years ago. Today, Stay Catskills is a boutique vacation rental business with a handpicked collection of properties and a focus on delivering exceptional guest experiences. I work closely with both homeowners and travelers to ensure every stay is comfortable, thoughtfully designed, and stress-free—from arrival to checkout.

Beyond managing homes, I’ve built something I’m truly proud of—a business that strengthens the local economy and gives back to the community. Over the past decade, I’ve provided steady work to family-run businesses like garbage collectors, landscapers, contractors, and maintenance crews, helping to keep both jobs and dollars right here in the Catskills.

I also lead a team of dedicated cleaners—an all-women crew, many of whom are mothers or single mothers who rely on this income. My sister works alongside me as both co-host and cleaning supervisor, making sure every home is guest-ready and every detail is handled with care. Their support, reliability, and hard work are the heart of Stay Catskills. Truly, my business wouldn’t be what it is today without them. I’m proud to provide flexible, meaningful work that supports their families—just as they’ve supported the growth of mine.

A few years ago, my husband and I added two of our own properties to the Stay Catskills collection. One is a peaceful, off-grid tiny cabin—designed for guests who want to unplug and fully immerse themselves in nature. The other is especially close to my heart: we purchased and renovated my childhood home, transforming it into a warm, welcoming Airbnb that blends nostalgia with comfort. It’s been a full-circle moment—creating new memories in a place that holds so many of my own.

What sets Stay Catskills apart is the personal connection. I’m hands-on, thoughtful, and truly invested in every guest’s experience. Whether it’s a cozy ski weekend, a wedding celebration, or a last-minute escape from the city, I help people find rest, connection, and joy in the mountains.

I’m proud of the trust I’ve built—with homeowners who hand me the keys to their beloved properties, and with guests who return year after year. And I’m proud that my children get to see me doing meaningful work that blends creativity, care, and community—on my own terms.

Can you tell us about a time you’ve had to pivot?

Before starting my business, I was living in Sarasota, Florida, managing a fitness center that was part of a larger chain. I was working over 60 hours a week, newly married, and starting to think about having a family—but I wasn’t sure how that would fit into my career. I loved the sun and warmth of Florida, but I missed my hometown of Bovina Center, NY. More than anything, I missed that sense of community and belonging.

Then came the moment that changed everything. At a company-wide management meeting, one of the managers—who was also a single mother—was recognized for a big achievement: leading her team to hit a major sales goal by staying late on October 31st. Everyone applauded and cheered. But then it was shared that in doing so, she had missed her daughter’s first Halloween.

She was doing what she needed to do to support her daughter, and I had deep respect for her strength and commitment. But all I could think was, She missed her daughter’s first Halloween. And I realized that if I stayed in that career path, I would likely have to make those same kinds of choices—and my priorities had shifted.

That was my wake-up call.

Soon after, my husband and I made the decision to move back to my hometown in the Catskills. He started a contracting business, and I focused on starting and raising our family. That pivot—away from the corporate grind and toward a life centered on family, flexibility, and community—ultimately set me on the path to launching Stay Catskills.

It’s a business that reflects the life I wanted to build: one where I could do meaningful work, support other families, and be present for the moments that matter most.

How’d you think through whether to sell directly on your own site or through a platform like Amazon, Etsy, Cratejoy, etc.

My vacation rental business is fully online. I list my properties on major platforms like Airbnb, VRBO, and Booking.com, as well as smaller niche sites—and I also have a direct booking website. While I’d love for more guests to book directly, the reality is that SEO and platform algorithms make it hard for independent sites to compete with the visibility and reach of large booking platforms. So, the majority of traffic still comes through Airbnb and similar sites.

There are pros and cons. The platforms provide access to a huge audience and offer built-in protections for both guests and hosts, including insurance and support systems. But the increased fees—platform service fees, state and county taxes, and cleaning fees—can feel overwhelming to guests and are often a source of frustration. This gets a lot of press, especially around cleaning fees, and I understand why.

That said, the cleaning fee reflects a real service. Cleaners need to be paid a fair, living wage—especially in a rural economy where reliable work is essential. It costs money to maintain high standards between guests, and as a business owner, I need to price that service responsibly to support the people behind the scenes. I work with a team of professional cleaners, many of them mothers or single mothers, and their work is the backbone of each guest’s experience.

It’s hard to compete with private hosts who clean their own properties and can reduce or eliminate the cleaning fee to make their listings more attractive. But those hosts often make up their profit in the nightly rate—it’s just structured differently.

I believe transparency and fairness matter. I do my best to offer pricing that reflects the real cost of quality hospitality, while continuing to build relationships and encourage guests to book direct whenever possible. My goal is always to provide not just a place to stay, but a truly thoughtful, comfortable, and well-supported experience.

Contact Info:

• Website: https://www.stay-catskills.com
• Instagram: https://www.instagram.com/staycatskills607
• Facebook: https://www.facebook.com/profile.php?id=61559691830149
• Linkedin: https://www.linkedin.com/in/kim-riera-994351311

Image Credits

Photographer: Joe Damone Photography