Stromboli Volcano Retreat: 10 Entrepreneurs on an Italian Island // Most Memorable Moments


Stromboli 2019 - Most Memorable Moments

Ten entrepreneurs + ten days co-living and co-working on an active volcanic island in the Mediterranean. The result? A completely transformative experience in terms of business growth/clarity, embracing new adventures, and strengthened relationships with both old and new friends.

This was my second year joining Volcano Retreats for their annual excursion to Stromboli, Italy. I linked up with nine fellow founders for ten days of business discussions, authentic Sicilian food, and hiking up an active volcano.


Stromboli = the most explosive of the Aeolian Islands

There is something incredibly surreal about going about your day as a volcano erupts above you. Stromboli is one of the most active volcanoes in the world, erupting every fifteen minutes …as it’s been doing for the past millennia. The island is literally one giant volcano surrounded by the Mediterranean. Needless to say, it’s a striking location to hold an entrepreneur retreat.


The Founders Crew

Each of us had our own incentives for joining the retreat, but we were all looking for opportunities to level up our businesses, create meaningful connections, and find clarity in our big picture goals.

Between the ten of us, our industries are incredibly varied: intellectual property licensing, info products, sales funnels, strategy, education, investing, and several instances of starting from scratch after recent exits. This rich diversity of interests meant that we had an opportunity to learn from the group's collective knowledge.

The majority of us also share a passion for location-independence. For the most past, we have the flexibility to run our business remotely or semi-remotely. We flew into Italy from all corners of the globe to kick things off and similarly scattered back out into the world at the end of the retreat.

Another commonality is that we are all full speed ahead along our entrepreneurial journeys. During the retreat, we all found pockets of time to hunker down behind our laptops and attempt to cram a full day’s worth of work into a few hours.


Memorable Moment #1: Hiking up an Active Volcano

This was the primary factor in my initial decision to visit Stromboli back in 2018. I returned again this year with the same goal: hike up an active volcano and watch hot lava erupt from the crater.

In retrospect, the night before our hike probably wasn’t the best time to pull a near all-nighter on the beach sharing a bottle of booze in front of the campfire, but it is what it is. We all woke up in the morning sleep-deprived and mildly hungover, but once we started our climb up the volcano, the fresh air and steep ascent sharpened our senses.


The prep:

Before we started our hike, we rented hiking boots, head lamps, rain jackets, helmets, and whatever else anyone needed. To prevent ash and sand from getting into our shoes, we folded a double layer of socks down over our laces and taped everything up for good measure.

Prepping our bodies with espresso and cigars before our hike. Power supplements.

Prepping our bodies with espresso and cigars before our hike. Power supplements.

The climb:

The hike up the volcano took a few hours, with plenty of breaks to enjoy the scenery and catch our breaths. We were led by our wonderful hiking guide and friend, Renzo, and his canine companion, Raksha. We were in excellent company.

Six weeks ago, I was recovering from a motorbike accident and my physical therapy involved slowly walking up and down the driveway of my parents’ house. Each step made me wince and my mom or dad walked alongside me in case I slipped. I had a mantra I’d repeat in my mind: “In six weeks, I am 100% hiking up that volcano.” I refused to believe this wouldn’t be possible and my stubbornness paid off.


The summit:

The topography is constantly morphing, but during our time up top, there were four active vents. Some spewed lava, others ash and gas, and one emitted an ear-splitting roar that made us scream and jump back. The volcano is very much active and the eruptions occurred continuously during our time at the summit.


Best moment:

By the time we got to the top, we were cold and wet, so we warmed up by snuggling together into a cuddle puddle. Any time someone moved and precious body heat escaped, they were chastised by those closest in proximity.


Memorable Moment #2: Hot Seats

Every morning, we’d carve out a few hours for “hot seats”. Hot seats provided an opportunity to dive deep in each other’s ventures.

How it works:

Each person gets one hour in the hot seat. To kick things off, this individual has ten uninterrupted minutes to lay out their current business challenges, goals, hesitations, opportunities, vulnerabilities, or anything else they feel like discussing.

Next, the whole group dives in: we ask questions, offer feedback, and share our opinions. Because each of us have different backgrounds and areas of expertise, the resulting feedback is a compilation of collective experience, knowledge, skills, and networks. This structure leads to authentic conversations, creative problem solving, and breakthroughs.

I believe that embracing vulnerability can be a powerful catalyst for personal growth. It invites authentic conversations, deeper connections, and creative problem solving. Hot seats are an incredible opportunity for this.


My hot seat:

Last year, my hot seat focused on balancing opportunities for business growth against the flexible lifestyle I’d established for myself. Essentially, I had a desire to scale my company, but I was also wary of losing the personal freedom that I value so highly.

Because my income is primarily passive and recurring, I have plenty of flexibility over when and where I decide to work. I can hustle my ass off for a few months, then take a couple weeks off without losing too much momentum. I don’t have a team to manage, so I’m responsible only for my own output. Furthermore, I can work from anywhere, whether it’s my apartment in Chiang Mai or a cafe on Stromboli. It’s a sweet spot to be in and I was hesitant to compromise it. I was aware of the potential of untapped markets for art licensing, but was unsure how to reach them without scaling too quickly and recklessly.

Based on the advice I received during that hot seat last year, I decided to sign on with a licensing agency in late 2018 to represent my company. This ticked both boxes:

  • I wanted to grow my business and maximize opportunities while still maintaining my “solopreneur” lifestyle.

  • In addition to this, the agency handles everything I was either bad at doing or had no interest in handling: reaching out to new clients, leveraging existing connections, optimizing and organizing my contracts, representing at trade shows and expos, and generally just pushing my art as far as it will go.


This year, I had a new focus I wanted to discuss.

I am sitting on some interesting potential: I have built a community around myself comprised of art enthusiasts, creative entrepreneurs, and fine artists. Thanks to my role as an educator, I’m seen as an authority figure in my field.

In addition to this, I also have time. Hiring the agency to represent me means I’ve freed up my plate substantially. I am no longer incentivized to actively seek new licensing opportunities because that role has now been filled.

Two of my primary drives in life are financial independence and autonomy of my time so I can pursue what I love and be creative. By pursuing passive income streams, I’ve been afforded both. Whatever I decide to seek next, it must have the potential to earn me recurring revenue and fulfill me on a personal level. I enjoy challenges and one of my biggest fears (besides failure) is that I am aiming below my full capacity.

There are some things I do very well. There are others that I do not. I am good at gauging trends and becoming an early adapter within this industry. I am good at creating artwork that people will buy. I work quickly and efficiently. I do not enjoy micromanaging others. Even with my students, I respond best to the challenging and thoughtful questions that require me to step back and consider fully before I answer. I manage myself well and do not like being tied down with a schedule and responsibilities to others. With all of these factors in mind, I wanted to discuss potential next steps with a group of peers during my hot seat.


Here’s where I netted out:

Path 1: Scale up my education program. Leverage the existing success of online teaching and grow it even larger. The most obvious solution here would be to increase my output: I currently launch a new course every quarter. What if I double that? The systems are already in place, so the additional workload would be feasible. However, there is also potential for thinking broader: Instead of focusing on one-off courses, I’m considering building out an all-encompassing education program under one umbrella: a creative entrepreneur masterclass that includes weekly assignments, personalized feedback, group discussions, and accountability check-ins. There is even an opportunity here to onboard guest educators to teach specialized topics. Essentially, this would be my top-tier offering: an elite course that helps aspiring creatives reach success.

Path 2: Embrace a brand new venture: The potential of this one excites me as well. I’m considering a lot of avenues and am still working on breaking them down in terms of feasibility and estimated success, but here’s the gist: publish a book, organize an affiliate program, pursue artist residencies (hello, Antarctica!), offer/seek mentorship, offer consulting services, curate a licensing program, and build out a well-rounded community for art licensors to unite and share experiences.

Overall, thanks to the hot seats, my mind is bursting with ideas and I’m excited about starting the implementation process.


Memorable Moment #3: Exploring the Island

There is a reason we only took on two hot seats a day– they are draining. We pour such intense focus into each person’s hot seat, which leaves us all mentally spent. My favorite way to recharge afterwards was to put on a good playlist, wander around the island on foot and let my mind wander.


My creative inspiration comes from travel; I paint the things I see around me while I’m exploring the world. Stromboli is bursting with creative inspiration– azure blues, cactus gardens, Mediterranean tiles, lemon trees, washed-up jellyfish, blooming hibiscus, and countless other motifs.

I photographed everything that sparked intrigue during my walks and painted when I was back at the house. Fun fact: If I left my paintings out for more than a couple hours to dry, a fine layer of volcanic ash would accumulate on the surface of the paper. There’s something to be said about hanging out on an active volcano.


Memorable Moment #4: The Food

Oh god, the food… I have favorite dishes all over the world, but nowhere does it quite like Italy. Between home-cooked Sicilian dinners, Neapolitan-style pizzas, charcuterie boards, and syrupy limoncello, I was in culinary heaven.

In Vietnam, I can’t get enough bánh mì. In Thailand, I’m all about that spicy larb. When I’m in Korea, I could eat raw blue crab for every meal. Here in Italy, fresh octopus salads are my absolute weakness.

While the food was a sensory overload all on its own, the experience of gathering with friends for meals was brilliant. We shared dishes, toasted glasses of wine, and dove deep into conversations ranging from discussing our businesses to sharing hilarious travel debauchery moments.

I’m a sucker for lemon desserts, so this meringue pie had me swooning. Thanks for the homemade pie, Renzo!

I’m a sucker for lemon desserts, so this meringue pie had me swooning. Thanks for the homemade pie, Renzo!

A home-cooked dinner at Barbara’s, our favorite BNB hostess on the island. She continued bringing out incredible dishes until our bellies were near bursting.

A home-cooked dinner at Barbara’s, our favorite BNB hostess on the island. She continued bringing out incredible dishes until our bellies were near bursting.

Favorite dining locations:


Eruptions at the Observatory. Our meal was continuously interrupted by the volcano erupting behind us. No complaints. Look at the upper right of this photo to see the hot lava in full-blown action.


Forgoing a table and dining on the ground in Ginostra. We were absolutely starving, so when the charcuterie plates arrived, we clustered together on the pavement and stuffed our faces with cheese, salami, bread, olives, and shrimp.


Paninis on the volcano summit. We ordered sandwiches earlier in the day and brought them with us to the top of Stromboli. They tasted even better because of the effort it took to arrive at the top.

Memorable Moment #5: Letters to Our Future Selves

At some point during the retreat, Logan mentioned digging for treasure. Those of us who attended last year’s retreat knew exactly what he was referring to: A year prior, we’d gathered on the beach and wrote letters to our future selves. We stuffed them in an airtight capsule and buried it near a sea cave. To be completely honest, I had absolutely zero faith that we would ever recover that capsule again. Luckily, I was completely wrong.

As I read my year-old letter, I was surprised with my past self for accurately predicting aspects of my future in terms of big-picture, while completely missing the mark on the actual details. For example, one of my goals was to travel to parts of the globe I’d never been. I expressed that I’d hopefully have a chance to explore Antarctica, Africa, India, or the Middle East at some point in the next year. I never made it to any of those destinations, but I did step foot in seven new countries in the time since I wrote that message. (Just none of the places I’d predicted.)


We decided to continue the tradition and buried a new capsule in the exact same spot with our new 2019 letters. Some of us wrote about goals, current desires, questions we hope to have answered in the next year, or just love letters to our future self.

I’m looking forward to digging out my note again a year from now and seeing what I’ve been able to accomplish and how far I’ve come.


Memorable Moment #6: Campfire at Secret Beach

The timing was arguably our absolute worst: At around midnight as we were wrapping up dinner, we decided that instead of getting a good night’s sleep before our volcano climb the next day, we’d rather drink copious amounts of wine and go swimming in the ocean. Cheers to impulsive decision-making, because this night was absolutely epic.

As we sat around the fire, we passed around a bottle of Żubrówka (Polish bison grass vodka), which was quickly drained. This liquid courage gave us the confidence to jump into the frigid water. Our splashes brought out pinpricks of bioluminescent plankton on the surface of the water, which were even more vibrant in the moonless night.

At some point, when the fire burned low and the booze was long ago consumed, we called it a night and stumbled back to the house to catch a few hours of sleep before our morning check-in. 10/10 wonderful evening.


Memorable Moment #7: Homemade Limoncello Lesson

Limoncello holds a special place in my heart: I first tasted it in 2004 during a Latin Club trip to Sorrento. I remember licking my lips to savor the sour sweetness. Limoncello is an Italian liqueur made out of –you guessed it– lemon zest. It’s syrupy and immensely sweet.

Our friend and BNB host, Barbara, makes the most divine limoncello I’ve ever tasted. She grows the lemons in her yard and usually has a few bottles aging on her shelf at any given moment. She invited a few of us over to learn how to make our own. (Okay, we kind of invited ourselves, but she was still incredibly welcoming.)

We picked ten lemons from our courtyard and brought them over to her place. She taught us how to peel the rinds, which we collected into a jar. The rest of the ingredients were vodka and a kilo of refined sugar dissolved in boiled water.

These are the life skills I came to Stromboli to learn.


Memorable Moment #8: Boat to Panarea and Ginostra

On the last full day of our retreat, we embraced boat life. We packed up the essentials we’d need for the day: sunscreen, snacks, and enough Prosecco to drown an army. Our boat took us on a journey to another one of the Aeolian Islands, Panarea.

En route, we stopped to explore sights along the way, including a patch of ocean rippling with giant sulfur bubbles; the sulfur rose from volcanic vents on the ocean floor and exploded on the surface. The smell was rotten, but the sight was unreal. Logan leapt off the boat and dove right through the middle of them. (“Oh my god the smell!”)


Memorable Moment #10: Meaningful Relationships

Now to wrap this up on a sappy note. The novelty of seeing hot lava in real life lured me to Stromboli for the first time, but the connections I made are what brought me back again this year.

The friendships that I made during my first year on Stromboli altered the trajectory of the past year– I wound up attached at the hip to some of those friends. We even lived together in Bali during the spring and are currently still roommates on the other side of the world, in Tbilisi, Georgia.

Honestly, this is one solid crew. Spending ten days living together, brainstorming together, dining together, and pretty much spending every second together accelerated casual friendships into deeper bonds.

Not only did we come together as a group, but the impromptu meetups and one-on-one connections were incredibly impactful. We’d periodically single each other out for individual chats to get private advice on business ideas, challenges, or life in general. These intimate discussions fostered close connections.

Ultimately, we were all there to not only uplevel our own ventures, but to help each other rise as well. This solidarity brought us together and created an environment of trust, creativity, and excitement about the future.


Cheers, Stromboli! See you again soon!