We caught up with the brilliant and insightful Justin & Megan Gross a few weeks ago and have shared our conversation below.
Hi Justin & Megan, really happy you were able to join us today and we’re looking forward to sharing your story and insights with our readers. Let’s start with the heart of it all – purpose. How did you find your purpose?
For both Justin and me, our story really began in childhood. Justin had a natural talent for building—and what he didn’t know, he had the determination and resourcefulness to figure out. Justin’s passion for building was shaped by summers at Door County’s Peninsula State Park and the steady influence of his grandfather, a journeyman carpenter. Surrounded by rustic structures and natural beauty, he developed an early appreciation for craftsmanship and durability. But it was watching his grandfather work—with patience, precision, and pride—that instilled a lasting respect for the trades. That inspiration led Justin to construction management, where he blends technical skill with people-focused leadership. For him, it’s about more than building structures—it’s about honoring legacy, fostering collaboration, and creating spaces that stand the test of time. I spent much of my childhood walking construction sites with my dad, who worked for a residential builder and also built homes on the side. I was always in awe of how he could take an idea, sketch it out on paper, and turn it into a beautiful home that people would live in and love.
I was especially captivated by the interiors—how each home had its own unique personality. I was fascinated by the way interior designers could evoke emotion through color, layout, and style. That early exposure sparked a lifelong passion for design, construction, and the magic of bringing something to life from nothing.
During our college years—at the same school—we naturally bonded over our shared interests. Justin pursued commercial construction and structural engineering, while I focused on electrical engineering with an eye toward architecture. When we weren’t in class, we were walking through historic neighborhoods, dreaming of what we might build together one day.
A few years later, we were married and working in our respective fields—Justin in construction, and me in engineering. We bought a fixer-upper and dove in headfirst, pouring our hearts (and skills!) into making it our own. After nearly a decade in engineering, I paused my career to focus on raising our young kids. But when they headed off to school, I found myself standing at a new beginning, asking, “What’s next?”
The answer was clear: my passion still lived in real estate, design, and creating spaces that people could truly feel at home in. Justin and I both wanted to build something that reflected who we are—not just as professionals, but as a family. And so, we launched our own business, one that brought together our skills, passions, and even our kids. That’s how Cottage & Boutique was born.
At the heart of it all is our purpose: to create unforgettable experiences for our guests, and spaces that feel both beautiful and deeply personal.
Thanks, so before we move on maybe you can share a bit more about yourself?
Location, Location, Location! When we decided to launch our vacation rental journey, we knew Door County, Wisconsin was the perfect place to start—with Cottage & Bay. Door County is a place close to our hearts: Justin grew up vacationing there as a child, and it’s become a favorite destination for our own family over the years. Often called the “Cape Cod of the Midwest,” Door County is known for its charming small towns, stunning Great Lakes shoreline, and endless opportunities for shopping, wine tasting, outdoor adventures, fish boils, and more.
With such a special location as our foundation, we set out to create a truly memorable experience for our guests. The home we chose sits on over four wooded acres, offering a peaceful retreat that’s still less than two miles from the nearest town—so guests get the best of both worlds: privacy and easy access to beaches, restaurants, and shops.
With a lot of hands-on work, years of combined experience, and help from some amazing local professionals, we transformed the space into a cozy, dog-friendly getaway where guests can connect, relax, and explore. Whether it’s roasting marshmallows around the outdoor fire pit, grilling dinner on the back deck, or spotting wildlife in the woods, the outdoor spaces are a big part of what makes it special. Inside, there’s just as much to enjoy—like warming up by the fireplace, playing games in the game room, or soaking up the natural light in the welcoming sunroom.
There is so much advice out there about all the different skills and qualities folks need to develop in order to succeed in today’s highly competitive environment and often it can feel overwhelming. So, if we had to break it down to just the three that matter most, which three skills or qualities would you focus on?
Patience – Building our vacation rental business has been a dream for a long time, but it didn’t happen overnight. It took time to really shape what we wanted it to be and define our mission. Being patient allowed us the space to make thoughtful decisions and grow something meaningful and intentional.
Play to your strengths, and know when to delegate – Justin and I love curating a memorable guest experience, and that’s where we’ve chosen to focus our energy. But we also recognize that we can’t do it all—especially with kids and other life responsibilities—so we brought in an amazing co-host who helps us take that guest experience even further. Knowing when to bring someone in who can do something better (and loves doing it!) has made all the difference.
Community – Surrounding yourself with people who are on a similar path is huge. We’ve learned so much by connecting with others in the vacation rental world—sharing ideas, asking questions, and supporting each other. You can go it alone, but being part of a community brings encouragement, insight, and momentum that you just don’t get solo.
Okay, so before we go, is there anyone you’d like to shoutout for the role they’ve played in helping you develop the essential skills or overcome challenges along the way?
We joined an educational community for vacation rental investors, and it’s been an absolute game-changer for us. It’s given us invaluable insights that helped us steer clear of major pitfalls as we started our hosting journey. Beyond the practical knowledge, it’s also connected us with some incredible entrepreneurs—people who are not only passionate about real estate but also about creating memorable, one-of-a-kind experiences for their guests. The personal connections we’ve developed, in particular, have been one of the most impactful parts of our journey. The support and inspiration we’ve found there have truly shaped the way we approach our business.
Contact Info:
- Website: https://www.cottageandboutique.com
- Instagram: https://www.instagram.com/cottageandbay/
- Facebook: https://www.facebook.com/CottageandBoutique
Image Credits
Kayla Hurst Photo
so if you or someone you know deserves recognition please let us know here.
