THE OLIVE JAR FOUNDER STORY
Have You Wondered
“What will my guests remember most?”
There’s a lot of passion and expertise that go into running The Olive Jar every day. People often ask me, “How’d you get into serving Airbnb hosts? It’s so…niche.” (I love when they say niche!)
To that question, I usually reply, “How much time do you have?”
If you’re a vacation rental host, maybe you’ve been asked a similar question (i.e. “How’d you get into Airbnb hosting?”). I bet you’ve got years of other careers and work experience on your resume, but you’ve found yourself hosting travelers in the wild Wild West of the short-term rental market, competing with big hotel chains and boutique motels on the rise.
You might feel a little (or a lot of) imposter syndrome creep up now and then, second guessing yourself, “Am I really a 5-star host?” Perhaps the real question keeping you up at night is this:
“WHAT WILL MY GUESTS REMEMBER MOST?”
I have an answer for you in the form of my own story.
Whether you’re a seasoned host, have room to improve, or need a complete makeover, revisit your point of inspiration.
I’m sharing my point of inspiration for The Olive Jar here. Let’s see if we have a thing or two in common, shall we?
CHAPTER ONE
Fresh out of college, I packed my bags and decided to work my way across Europe, partly in search of unforgettable experiences in faraway locations, but mostly in search of gelato.
Italy was the real destination, where my family tree sprouted. As the end of my glorious journey neared, my inner adventurer realized I had forgotten to listen to my inner accountant, and I found myself stranded in Taormina, Sicily with a zero-ed out bank account.
I COULD UNDERSTAND how it sounds dramatic to say “stranded” when you’re looking at one of the most gorgeous parts of the world—but I was literally without a penny to my name, no life line, and no way to get home. In a moment like that, beauty is fleeting!
In desperate hopes of cutting my trip short and heading back to London (home at the time), I resorted to begging my way onto trains that would take me to the Palermo International airport—my brilliant strategy being: simply change my flight right this instant…welp, that didn’t pan out for so many reasons not worth listing.
PANIC STRUCK. Simultaneously, I had another brilliant plan to beg my way into nearby hostels. Just one more train ride into the city would get me there.
This is the point in my story where I am reminded that I tried many times to whip out the only credit card I had on me: American Express. Ya know, it’s everywhere you want to be.
There I stood at the ticket kiosk swiping that worn down AMEX, praying I could buy a train ticket into the city.
Welp. as it turns out, THat AMEX tagline DID not apply EVERYWHERE I NEEDED IT in SICILY.
IN THIS LAST ATTEMPT, the flood gates opened. I broke down in tears, praying, “Save me, please please pleeeease.”
I “Charlie Brown” walked my way to the stationed train, where I reached a train attendant. he could have been my grandfather. SO KIND, He offered a warm welcome, smiling ear to ear…AND ready to take my ticket.
I shook my head, miming “no ticket” with empty hands. Looking back, it was comical.
He consoled me in Italian that I (shamefully) couldn’t translate, pointing me to the ticket kiosk—to which I responded in English, “American Express is NOT everywhere you want to be.”
We were lost in translation.
But, he wasn’t there to teach me a lesson. He simply patted me on the back, allowed me to board his train and offered me a seat. I thanked him, he stepped off the train, and I thought that would be the last I’d see of him.
I was relieved in the moment, but would be forever grateful after what happened next:
He came back. This time with a sandwich in hand — clearly packed from home.
He unwrapped his sandwich, broke it in two, and handed me half.
I was STRUCK—ALL AT ONCE FEELING SHOCKED, comfortED and humbled by his generosity. I will never forget my first bite of that salami & provolone sandwich.
Years later, my husband and I would come to name our first daughter Sicily.
And, you’ll hear more about that train experience by the end of this post.
CHAPTER TWO
Now, I’ve changed my spending habits since college, but my hunger for gelato and a good Italian sub will never die.
Woven throughout my career life, home life and faith journey, I’ve used meal table experiences to tell compelling stories that invite, inspire and engage guests into transformative conversations.
By the end of my 20’s, I was hosting pop-up dinners in Los Angeles with chef-inspired multi-course meals, surprising and delighting guests at every dish.
Producing environments just like this for brands and organizations, I started my first business in 2012. At Tribe of Asher, we specialized in experiential marketing for brands and orgs. We used film, hospitality and design as our mediums to engage and build those companies a loyal following.
But hang on…I should back up a bit.
My very first career right out of college was in film advertising, where I was writing and producing teasers, trailers and TV spots for studio films.
I was never into selling products. from day one, I was passionate about selling stories.
It was natural for me when I transitioned into film production, where I served non-profit orgs producing short documentary stories about their brands. Back then, these were called “branded docs,” but today that’s just advertising.
MY CREATIVE JOURNEY WASN’T LINEAR. Somewhere in THE FILM ADVERTISING & PRODUCTION WINDOW, I started playing with stories through food and hospitality in those pop-ups I mentioned.
IN 2014, I BECAME A MOTHER, WHICH CONTINUES TO BE the greatest CREATIVE ENDEAVOR of my life; AND, 2014 WAS RIGHT AROUND THE TIME I GOT INTO film and commercial production design, styling for screen.
What I didn’t see coming was the fire THAT BOTH MOTHERHOOD AND DESIGN would light within me.
By the way, would you be surprised to hear that my work in production design started with food?
It began with phones calls from within my filmmaker network, asking me, “Can you style a magical dinner scene for my indie feature?” or “Can you be the food stylist for this Sargentos vlogger series?”
Soon after, I was styling home interiors (set decorating) for the next 8 or 9 years. I learned very very quickly how to style spaces and special moments for camera, manipulating sets and details in a way that would evoke emotion, further the plot and deepen the story of every character in the room.
Then eventually, I rebranded Tribe of Asher—combining everything I knew in marketing, film, hospitality and design—to officially identify our company as a boutique experiential marketing agency.
ONE OF THE PROUDEST MOMENTS FOR TRIBE OF ASHER WAS seeing ONE OF OUR films air on oprah’s EMMY AWARD-WINNING show, super soul sunday.
Originally co-produced with Long Winter Media for the launch of Fuller Studio’s Brehm Center digital art gallery, “Come Eat” was a short documentary I was honored to direct—especially because it came after having spent years producing experiential events with an incredibly talented chef, who happened to be a dear friend too.
ABOUT THE FILM: Recovering from a life of addiction, Chef Christian Navarro serves up his recreation of a traditional Filipino dish to reveal how he found redemption and reclaimed his life.
WATCH HERE AND ENJOY.
No matter the medium, whether it was client work on the clock, serving L.A. with my faith community called Mosaic, or any opportunity to host friends and family in our own home…
I just couldn’t stop creating unique ways to invite people in.
CHAPTER THREE
Hospitality was always the heart and soul of my experiential work, because it was always about sparking connection. In every platform, I kept finding my way back to it. It’s what makes me tick.
I never forgot that Sicilian train attendant. His one job was to take tickets and operate that train—he wasn’t paid to share his meal with me. He simply extended himself in an act of generosity.
I had found belonging where I least expected—ON A TRAIN.
As I savored the first bite of that sandwich, I asked him for his name and address, so I could properly thank him later…
his name was Salvatore.
then, after he’d stepped away for good, and the train took off, it suddenly occurred to me: WHAT DOES “Salvatore” MEAN? I cracked open my Italian dictionary, AND…
…Translated in English, SALVATORE MEANS “Savior.”
The prayers of a dumb college grad were answered. I have a feeling I wasn’t the only traveler Salvatore had rescued in his lifetime.
2 decades later, and I am still retelling the story of Salvatore, my Sicilian “host.” It would be an understatement to say…
That single point of human connection I experienced in Sicily became a significant point of inspiration for The Olive Jar as you see it today.
If you’re a vacation rental host who wants to understand what it TAKES to offer your travelers an unforgettable experience, I promise they’ll never forget your generosity.
To us, “home” can be found anywhere—on a moving train; off the grid; around the fire under a starry sky—anywhere there is sharing.
I launched The Olive Jar to serve vacation rental hosts exclusively, because I’m certain we share the same value for hosting connective travel experiences.
AT THE OLIVE JAR, we compassionately serve hosts to create spaces and experiences for your traveling guests to reconnect with themselves and one another. Connection is baked right into our brand’s mission and vision.
Our goal is to reverse the trend of loneliness and isolation that our global community faces by empowering hosts to elevate their guest experiences into engaging environments. Using design, amenities and media as mechanisms to promote deep connection, we foster greater intimacy within all types of relationships.
In the story of my EVOLVING career, The Olive Jar is my favorite chapter yet.
I’ve touched many industries, but the most thrilling by far is the short-term rental market. It’s so…niche. I was intentional about choosing this industry. It was never a side hustle for me. The Olive Jar has been my full time gig since the day we opened shop; and, I’m not surprised that our clients are just as intentional in the ways they serve their travelers.
Every host we have worked with has been beautifully committed to offer unforgettable Getaways to Reconnect.
What’s your story?
What was that unforgettable point of inspiration that got you into hosting? Share in the comments.
Need help in the inspiration department? Just click that button below. I’d love nothing more than to share a moment together.
Photo credits: Anchor Pictures; Valerie Noell; Chandra Wicke; Third Wall Photo; June Choi