When You’re An Entrepreneur Your Team Means Everything

When You’re An Entrepreneur Your Team Means Everything

What they say is true. Being an entrepreneur is one of the hardest things you’ll ever do. I know because I’ve lived it. We started operations for Tailored Stay in December of 2019. My team was fresh faced, excited, getting orders and driving momentum.  And then the pandemic hit. So what did we do?

 We pivoted our operations, like so many other companies had to do. Luckily, our beta test was in the greater Taos area of New Mexico where services like Instacart and Door Dash didn’t exist. So we shopped and delivered groceries and supplies to locals. We were glad to help yet it felt awkward and disappointing from a team standpoint that what we were doing was so off the mark of what we had envisioned for the vacation rental industry.

I can honestly say that I don’t think we would have gotten through that period without an amazing and resilient team. They have stuck with me through and through. Working nights and weekends, supporting me during the tough days and encouraging me with the excitement and top-notch skills they bring to the table.

In the summer of 2020 we were back to wowing guests of vacation rental properties with curated groceries, vacation amenities and celebrations all set-up in their units before they arrived.


Bachelorette party decor
Birthday Decor
vacation grilling

Our product market fit was great. We were able to place over 250 orders with some repeat and loyal customers. 75% of the property management companies that we worked with approached us for our services and we have a signed ‘Letter of Intent’ from several more who want to work with us throughout the US.

Even with these successes, some days are still hard so I will turn my attention to what I am grateful for:

Like many startup founders, I would love to spend 100% of my time on working on my business but being bootstrapped, to date, means also finding investors and partners.

What I am Grateful for as an Entrepreneur

1. Investors have been willing to take my calls. I have received terrific feedback from industry leaders, executives, Angel Investors and VC’s. Each call puts us closer to our goal.

2. This industry that we have chosen and are passionate about is young and supportive of one another as startups in the vacation rental space. Having attended the VRMA Conference in Chicago I was so warmed by how much people wanted everybody else to succeed. It’s truly an exciting, the sky’s the limit, space to be in.

3. Definitely not lastly, is my team. I could brag about them all day. Please indulge me as I do just that.

The Team, as a Founder, I am so Lucky to Have

Stephen Fitzgerald CFO

I know better than to not call out my husband first. Anyone who has the privilege of knowing Stephen knows these two things about him: he has a solid sober prospective and an abundance of integrity in intention and follow through which makes him a great partner and leader. Stephen has spent his entire career in Executive positions within leading hospitality companies such as Saber, Hotwire & Hilton. He brings decades of experience to the table in Ecommerce, Finance and his success and thorough knowledge of OTA’s.

Nicholas Armstrong CTO

A true Texan at heart, there is not a problem that Nick can’t meet. He gladly tackles new IT projects and pulls out some sort of magic wand combining experience and fierce intelligence to make them work. He has earned successes and leadership positions in the world of IT. Currently he works with highly sensitive healthcare data but lucky for us, in his early career also worked with grocery inventory. This man understands his item files and UPC’s!

Cecilia Cuff Hospitality & Operations Director

When I first contacted Cecilia on LinkedIn to work with Tailored Stay, I thought there was no way she’d be interested. With her background at Hyatt hotels and having been handpicked to renovate Taos Ski Valley, I didn’t think she’d have much interest in a startup. Boy, was I wrong! Cecilia has the largest appetite for entrepreneurship of any of us. She co-owns several successful businesses including the newly opened Bronseville Winery which celebrates the cultural history of the Bronzeville neighborhood in Chicago.

Pat Parker Lead Website & WooCommerce Developer 

Pat is another team member that we happened to stumble a pon and bring into the fold. Pat started as a contractor for us but we quickly knew that both her experience and personality made her a great fit for our team. Pat has drove numerous projects throughout her long career in development and IT. She is a true expert when it comes to web development and WooCommerce inventory. Her passion and specialty is writing code to make things work that typically wouldn’t have otherwise.

Mark Grosso Head of Product & Legal Council

When you take someone who has extensive leadership experience in product marketing during his decade with Verizon, combined with a J.D. that he earned at night, you get a two-in-one combination with a sense of humor to boot. Mark’s sharpness and attention to detail are team assets we rely on every day. His emotional support is invaluable. He props everyone up. Mark is a remarkable leader and team player.

Anna Arrow PR & Customer Success

Some little known facts about Anna: she graduated as Valedictorian from High School and had the talent and ambition to move to Hollywood after college where she had a sucesful run as an actress. Anna’s passions are people and animals (she now helps run a small hobby farm in Northern, IL). An extremely affective communicator and commited to providing world-class guest services that she gained in running large nightclubs and international festivals in the US and abroad, Anna has a unique skillset. She fosters creation and sees through complexities with unique and inspired views.

I couldn’t be more grateful for the talent, support and perserverence of this team. The startup grind is definately not for everyone. We’ve somehow found the perfect ingredients to align us with success. Thank you my team, my family, my friends.

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