HOW IT STARTEd

I was born and raised in the Boston suburbs of Massachusetts. Graduating from UMASS Amherst, I moved to the Midwest and spent the first 5 years of my career based out of Milwaukee, Wisconsin and working for a Fortune 500 company in Finance. 

Always tugging at my heart from the very start has been the need to create something - getting out of a spreadsheet and into something that would use the right side of my brain. But alas, life happened, and in the meantime, I met the love of my life, Jake, and together we started a family, having our son Charlie in Milwaukee in 2013 and adopting a dog (and then another) along the way. My career at the same time chugged along, with promotions that promised more financial stability for my family and a secure future.

I was called back to the East Coast (don’t get me wrong -- I love Milwaukee, but Boston is my home). We moved home to Boston in 2014 and I begrudgingly continued my finance career until I decided finance was no more for me. I left for a scaling SaaS company in an operational role in 2019. The change made me happier, but there was still something missing. Having roped Jake into the mindset of “let’s do something that’s OURS!” we purchased a cabin in New Hampshire in the spring of 2019 with the intent to turn it into a short term stay for folks looking to either ski the mountains or peep leaves in the fall. I was ecstatic. This would be my business to grow and cultivate.

Another idea sparked while doing all of the real estate paperwork for the home. I started to get overwhelmed by all of the cute cabin aesthetics on Pinterest, and decided that to start a following and get some renters on the books I would host an Instagram design challenge. Three designers from the Boston area designed a vision board for the space and competed on an Instagram post for the most likes to have their design come to life in the New Hampshire cabin. The contest was a huge success and we gained thousands of likes and impressions from the postings and subsequent sharings. Best of all, we had a cohesive design vision for our cabin.

We got to work. It took way longer than we imagined, but we spent every weekend of the summer of 2019 driving up to New Hampshire and renovating the space. We opened the space in October of 2019 and have rented over 90% of available capacity since then. The success of our little cabin has led me to want to do this again and again, optimizing and improving the process in doing so along the way. Even more so, I’d love to help other folks in realizing their dream. A short term rental space is a great way to generate some side income, and the satisfaction of happy guests has been so rewarding.