Most family beach vacations are about relaxing, but when you have a dad, husband, and brother-in-law who are entrepreneurs, conversations somehow always make it back to business.
“You want a popsicle? “
“Do you know the margins I was just reading about on seasonal consumables the other day?” .
It was August of 2022.
We had just had a record month in our e-commerce business.
It was a perfect time to scale.
And increasingly, after our gifted stay at the Ritz five months prior, all I could think about was Tanner being a McLaren who’s never had an open road
I really sensed it was Tanner’s turn to be at the helm.
Not just running operations and logistics, but being the visionary. Driving the business. Being given the reins instead of just helping me navigate which direction to turn.
So one night after dinner and the endless-energy-horde of adorable small humans were in bed, I turned to my brother-in-law and asked, “Dave, could you see us doing anything else? Is there anything you think we should be exploring”
I glanced at Tanner, who was sitting cross legged and slouched on the other side of the couch… and he was not having it.
“This is shiny object syndrome, Melissa”, he had protested more than once over the last few months when I would bring the idea up. “I am happy doing what I’m doing. Please stop trying to start a new business…… No, there is nothing else I’m interested in right now…. I am FINE.”
With all those past conversations in mind, he had zero interest in this conversation.
Ignoring his downturned eyebrows and annoyed glances, I continued.
Dave, unaware of the silent conversation Tanner and I were having, paused, glanced up, and then remarked:
“You know, I'd love to see you guys do something together… something you are both passionate about. What are some things that you guys really enjoy doing together?”
The first thing that came to mind was our Airbnb.
We had renovated the space above our garage two years prior to host all our out of town family (since our 3 BR home was full at that point with the five of us).
It was Tanner who first wanted to list it on Airbnb
“Tanner, no one is going to want to stay over our garage”, I said drily.
Well was I wrong. Our Airbnb took off. We even earned the privilege of Superhost status in less than 55 days.
And we loved hosting guests. In a season with 3 little kids and not a lot of ability to host the big events and dinners we were used to, let alone go to dinners or events, we had the privilege of having people come to us.
We were able to pour all of our love for hospitality, intentionality, and personalization into this Airbnb.
As we had run our e-commerce business, I always remarked “I wish people raved about what our home decor the same way people rave about our Airbnb”
I shared that comment with Dave, and opened up about the Ritz, and our bigger dream to host and serve people on a bigger scale.
“But, of course, we can’t do that for a long time because we don’t have the capital”
“Well, Melissa, you can always raise the capital” Dave quickly countered.
Thank you Dave. This coming from the guy who runs a very successful SAAS company” I thought drily in my head.
But it also made me pause. Was I thinking too small? Was I operating out of a scarcity mentality? Could it be we were holding ourselves back? Were there others out there who want to help fund our dream project?
…..
6 days later, after big hugs, lots of aloe, 154 popsicles consumed, and 7 small kids, 7 adults, and about 3 pounds of extra sand piling into different cars, we drove off.
Our baby girl soon fell asleep, and the boys quietly watched a movie in the back as we drove home.
In whispered tones, I asked one more time…
“Tanner… could we just dream about this idea for one second together? I’m just curious: would this be something that you might be interested in?”
Tanner sighed. “Melissa. Our e-com business has been your baby. Your dream. I don’t want you to feel unsupported in this business, or take away from what you’ve built. You’ve done such a great job building this and I don't want to take away your dream.”
There it was. The real reason.
“Tanner I don’t! I feel so supported by you! My dream is for you to really thrive. That’s my dream. And if you feel that running operations and logistics is where you’ll thrive best, then we stay. But if thriving means you do something else, then I’d love to at least dream about a pivot”
He nodded. It was almost like he needed the permission to dream about something else for a second.
And so he opened up– sharing about growing up in Young Life and service. He started sharing about how really his dream wasn’t just short term rentals. If we were going to do it, it would be so much more than that.
He would want to build a place where the veil between heaven and earth would be thinned.
Where the dying art of service and hospitality would be renewed.
Where people could come and escape from the grind of daily life--no matter how amazing or tough it was..
Where people could come and be known by their name.
Where instagrammable and cheap would be replaced with timeless beauty and high quality.
Where the fast paced life could be given a pause and people could breathe deeply and slow down.
And so in that sand filled car ride: Cypress was born.
In hushed tones, and hope filled hearts, we leaned into a dream that a week before had felt distant and impossible.
And Tanner, moved from hesitancy to possibility, had his open road.
….
So that’s it. That’s our story. That’s how Cypress Resort came to be.
Thank you for reading these posts and getting to know our story and why Cypress Resort exists.
It really is about serving you and creating a space for you to rest in nature’s embrace without sacrificing comfort or luxury.
Warmly,
Melissa and Tanner
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