Arrival at the Edge of the World

On January 6, 2026, we left Mendoza (Part 2 of our trip) and took a short flight to Buenos Aires, where we connected onto another flight—about three hours—directly to El Calafate, deep in Argentine Patagonia.

Waiting for us when we arrived was Pol, the uncle of my friend Ignacio in Miami. Ignacio had connected us the year before while we were planning this trip.

That connection turned out to be invaluable.

Moments like this are part of what makes Fearless Journeys different. We don’t just travel—we lean into relationships. Over the years I’ve built friendships in many parts of the world, and those relationships allow us to connect with locals in ways that ordinary tourism rarely does.

Pol welcomed us into his home, where we each had our own bedrooms and bathrooms. Throughout the week he helped coordinate transportation, recommend restaurants, and introduce us to people throughout the region.

Before long we noticed something amusing: everywhere we went, people seemed to know him.

Restaurants. Drivers. Guides. Café owners.

Everyone had a story about Pol.

It quickly became clear that if you go to El Calafate…

you better call Pol.

The first surprise came right at the airport. Even though we had just arrived on a domestic flight from Buenos Aires, we had to run our bags through a scanner before leaving the terminal.

Why?

Because Patagonia is a delicate environmental ecosystem. Authorities want to make sure visitors aren’t bringing in plants, seeds, or agricultural products that could disrupt the region.

As Pol drove us into town he pointed out the massive lake beside the road.

Lake Argentino, the largest lake in Argentina.

“The color is different every day,” he told us.

Over the next several days, we would see exactly what he meant.

Dinner at the End of the World

After settling into Pol’s home, he drove us into town for dinner at El Cucharon.

One item on the menu caught our attention immediately: guanaco.

The guanaco is an animal similar to a llama—or even a camel—and we would soon see them everywhere along the roads of Patagonia.

I enjoy trying unusual foods when I travel. It reminded me of the camel burger I had in Morocco in 2024, so I decided to give it a try.

And let me tell you—it was excellent.

We paired the meal with a Patagonia Malbec called Fin del Mundo—“End of the World.”

A very fitting name for a place this far south on the planet.

Walking on Ancient Ice

The next day we set out for one of the most unforgettable experiences of the entire trip: mini trekking on the Perito Moreno Glacier.

I’ve done a lot of cool things in my life.

But this one might take the cake—make that an ICE cream cake.

As we walked across the glacier, I must have said a dozen times:

“Is this place real?”

The glacier was named after Francisco “Perito” Moreno, the Argentine explorer who helped map Patagonia in the late 19th century.

Today it remains one of the few glaciers in the world that is still advancing.

Standing there surrounded by ice, sky, water, and wind, it was impossible not to think about creation itself—the brilliance and scale of a world like this.

Glaciers store freshwater, shape landscapes, feed rivers, regulate climate, and remind us of the powerful rhythms of Earth’s history.

Our guides from Hielo & Aventura fitted us with crampons and led us safely across the ice.

Ancient ice cracked softly beneath our feet.

One of the most unforgettable adventures of my life.

North to El Chaltén

The following day we drove about two hours north to El Chaltén, the small mountain town beneath the legendary Mount Fitz Roy.

Our plan had been to visit a nearby petrified forest, which Pol told me looks a lot like the Badlands of South Dakota—a place I’ve visited twice—but here it’s filled with dinosaur fossils.

Patagonia was once home to many dinosaurs.

Unfortunately, a rare morning rain made the terrain too dangerous to explore that day.

But Patagonia had another surprise waiting for us.

On the drive north we stopped at what looked like a simple roadside café.

Inside we found dinosaur bones, hand-drawn Patagonia maps from 1868 (many hilariously inaccurate), and stories of explorers and outlaws.

Yes—those outlaws.

Butch Cassidy and the Sundance Kid reportedly hid out there for a month in 1905 after robbing a bank nearby while fleeing the United States.

Eventually they escaped again and spent years on the run through Chile before ending up in Bolivia, where they were ultimately killed.

That’s when I joked:

“That’s also where Che Guevara met his fate—executed in Bolivia.”

Moral of the story?

If you’re a revolutionary… or a bank robber…

maybe avoid Bolivia.

When we arrived in El Chaltén, we grabbed lunch and checked into an Airbnb where we would stay for the night, then headed out to explore the trails.

A Camino Encounter in Patagonia

After arriving in El Chaltén we set out on a short hike to Mirador Cerro Torre.

As we neared the top, a young boy—maybe six years old—pointed at my hat.

“Camino de Santiago.”

I was wearing the same hat I had worn while walking the Camino de Santiago in Spain the previous summer. It features the famous scallop shell associated with Saint James.

His father explained to me they had walked part of the Camino just a month after I completed mine. He himself had walked the entire pilgrimage the previous December.

Then I noticed something else.

Someone was filming us.

They explained they run a travel YouTube channel called Borderless.

The father had grown up in the Soviet Union and was originally from Ukraine. At one point they had lived in Fort Lauderdale, where their son was born. Today they live in Brazil.

I laughed.

I told them I was born in Miami but raised in Fort Lauderdale.

The father looked at his son and said:

“He walked the Camino. He’s from Fort Lauderdale. And now we’re all here in Patagonia.”

“What does that tell you?”

I smiled.

“It tells us it’s a small world.”

Beneath the Towers of Fitz Roy

The next morning we woke early—around 7 AM.

We grabbed breakfast, stopped for coffee, and were on the trail by 8:30 AM.

Our hike took us to Laguna Capri, beneath the towering presence of Mount Fitz Roy.

The hike was about 9 kilometers round trip, taking a little over four hours at a reflective pace.

Some of the deeper trails in the area can stretch 10 hours or more, but even this route delivered extraordinary views.

We paused often—to breathe, reflect, and take it all in.

This may be one of the most majestic mountains I will ever see in my lifetime.

Patagonia teaches humility.

And it reinforces something we often say in Fearless Journeys:

Entrepreneurs need adventurous hearts.

Trips like this reinforce that idea. They push us outside our routines, challenge us physically and mentally, and help us grow the adventurous spirit needed to explore new ideas, new ventures, and new possibilities.

Music, Friendship, and Local Connections

On our drive back to El Calafate we rode with Waldemar, a friend of Pol’s.

During the drive he told us he was actually a musician who sings and plays guitar.

Driving visitors around Patagonia was simply something he did on the side.

Then he mentioned something interesting.

His weekly Thursday night gig was at one of the nicest restaurants in El Calafate called Mako.

And it just so happened that the day he was driving us was a Thursday.

So when we arrived back in town, we went.

Waldemar arranged a reservation and made sure we had some of the best seats in the house.

That evening he performed light rock and jazz while we enjoyed dinner.

Another example of how we prioritize relationships over reservations through Fearless Journeys.

Crossing the Border into Chile

The next day Pol arranged a rental car for us, complete with the special paperwork required to cross the border into Chile.

Both Pol and Waldemar gave us clear instructions—not just about the paperwork, but also about which roads to take and which ones to avoid.

Google Maps often suggests a shorter route that turns into rough dirt roads.

So we followed their advice.

Knowing a local guide—whether on a trip like this or when starting an entrepreneurial venture—can make all the difference. They understand the terrain and the pitfalls outsiders might miss.

As we drove south we passed guanacos wandering near the road, rheas (Patagonian ostriches), and road signs warning about snow and falling rocks.

One of the falling-rock signs looked dramatic enough that it almost seemed like it could also be warning about a meteor shower.

Who knows in Patagonia.

The dinosaurs that once roamed these lands didn’t have such warnings.

Torres del Paine: Patagonia at Its Wildest

Torres del Paine sits in southern Chilean Patagonia, shaped by glaciers, wind, and time.

We spent the day driving through the park, stopping often to walk along lakes, waterfalls, and viewpoints.

These were landscapes I had seen countless times before in photographs and travel books.

But nothing compares to being there.

The Southernmost Point

That night we stayed in Puerto Natales, the southernmost place any of us had ever been on the planet (51.7269 degrees south of the equator!)

Puerto Natales is a small city, very walkable from where we stayed, and even situated on the water — which is technically navigable to the Pacific Ocean. The temperature had started to drop, reminding us that even in the middle of summer, Patagonia carries a chill in the air.

We stayed at a hostel, though each of us had our own private room and bathroom, which made it a very comfortable stay.

That evening we headed to Baguales Brewery, where we enjoyed dinner and some excellent local craft beers. The brewery stayed open quite late, which made sense given the time of year.

In southern Patagonia during January, daylight stretches deep into the evening.

The sun didn’t set until after 10:00 PM.

It reminded me of being in Norway in June, when summer days stretch late into the night. Except this time we were experiencing the same phenomenon in southern Chile in January—also summer, just in the Southern Hemisphere. I guess we know how to find longer days.

The next morning I woke up early and took a short walk around town before we headed to breakfast at an amazing café called Caffetto.

There I had what might have been the best French toast I’ve ever had, and the coffee was amazing too—exactly what we needed before starting the drive back across Patagonia.

From there we filled up our gas tank and began the drive north toward Argentina.

About thirty minutes later, we were approaching the border again.

At the Chilean border control, the guard saw my U.S. passport and asked me a question I definitely didn’t expect to hear that far south in the world.

“What do you think of Trump?”

Yikes.

In a split second I decided on what felt like the safest possible answer.

“Más o menos.”

He nodded.

Then he asked me what I thought about Rubio.

I gave him a big thumbs up.

He smiled and stamped my passport.

As he handed it back to me, I had a small realization: even this far south in the world, someone knows the name of the U.S. Secretary of State. And they appear to like him.

When we got back in the car, I put on my Boca Juniors long-sleeve shirt, the iconic Argentine soccer club, and told my friends:

“Time to re-enter Argentina.”

After we checked in with the Argentine agents inside the office, a border patrol guard asked to search our vehicle.

We let him take a quick look.

As we got back into the car, he looked at my shirt and told me he didn’t like Boca Juniors.

He was a River Plate fan.

I smiled and said:

“Necesito ir.”
(I need to go.)

He laughed.

And waved us through.

Turn Off the News. Go See the World

There was a lot going on in the world during our trip.

But it felt good to step away from it all.

Sometimes the best thing you can do is turn off the news and go see the world.

I highly recommend Patagonia.

And if you ever find yourself heading to El Calafate…

Just remember one thing.

You better call Pol.

If you haven’t yet taken a trip with Fearless Journeys, you don’t know what you’re missing. Reply to this email and let me know some places you’d like to travel with us. You never know. We may already be planning something there.

We had 10 people signed up, and to secure the best group experience and pricing, we really needed 20 or more. Rather than force the timing, I’ve decided to move the trip to 2027.

The good news: with more runway, I’m confident we’ll put together a strong group and an incredible experience.

If you’re interested in joining us in 2027, I’d love your input. I’m currently looking at two options in May and June 2027, and your feedback will help shape the final dates.

Help us choose the 2027 dates here: https://forms.gle/cw6kWiPAmKeoueg86

Sometimes the right move is a reset — and this one sets us up to do Israel the right way, with the right people, at the right time. I hope you’ll be able to join us -- next year in Jerusalem!

That line didn’t come from me.

It came from one of our earliest Fearless Journeys travelers — someone who realized that if you wait for the perfect season of life, the perfect window, the perfect alignment…

You may never leave.

And if there is one place on earth that should not be postponed, it is the Holy Land.

An Important Update

We’ve refined our Israel experience.

After listening to feedback, we shortened the journey from 12 days to 10 days — without stripping out what makes it extraordinary.

We simply removed:

• Two hotel nights

• One partial leisure day in Tel Aviv

• The Gaza Envelope visit (now available as an optional early arrival add-on)

What remains is a powerful, immersive, premium experience.

Jerusalem.
The Western Wall.
The Sea of Galilee.
The Old City.
Sacred history that shaped civilization.

But also:

Meetings with innovators and builders in one of the most entrepreneurial ecosystems on the planet.

Israel is a nation sitting on history — while relentlessly building toward the future.

Few places combine faith, resilience, military necessity, technological innovation, and startup energy quite like Israel does.

You won’t just visit the Holy Land.

You’ll experience it — and meet the people shaping its next chapter.

And most importantly: your faith will deepen.

The Opportunity

With the revised 10-day itinerary, the price drops by $500 per person.

But here’s the key:

We need 20 people to unlock the preferred group pricing we’ve negotiated — hotels, transportation, and private access that allow us to do this the Fearless Journeys way.

Right now, 8 are committed — plus me.

We need 12 more.

Jesus had 12.

We need 20.

Twenty unlocks the pricing.
Twenty unlocks the full experience.
Twenty creates the shared momentum that makes these journeys unforgettable.

Why This Trip Is Different

This is not a bus tour.

This is not a generic pilgrimage.

This is a curated experience built on real relationships — connections that allow you to see Israel through a lens most groups never access.

Entrepreneurs.
Innovators.
Builders.
Faith.
History.
Resilience.

And for those who want more, the Jordan / Petra extension remains available immediately following the Israel experience.

The Timeline

We are reopening enrollment with the refined 10-day format.

👉 View the updated itinerary here: https://drive.google.com/file/d/1N-REicchHX1H-jWi8OX7lJ3WkJ-8UKiD/view?usp=sharing

👉 Secure your spot here: https://docs.google.com/forms/d/e/1FAIpQLSeVI1D665yT-t5Y2JryX9TLh7HXCoiUTiksl32RGcFrQgW4tw/viewform

We will make a final decision by the end of February.

If we reach 20 committed participants, we go.

If not, we pause.

Simple.

New pricing:

$5,774pp (double occupancy)

$7,039pp (single occupancy)

• If you are willing to share a room with a fellow traveler you do not know, drop me a line. We have a few people asking. And I know them all and can make proper pairings.

What’s Included:

• 1x Meeting upon arrival at the airport, assistance and transfer to the hotel

• 1x Transfer from the hotel to the airport. Meeting and assistance for your departure flight

• 9x Full Israeli buffet breakfast at your hotels

• 7 Dinners, including a cooking class and dinner

• 4 Lunches, including 2 Market tasting tours

• Private English-speaking licensed guide for 10 days of touring.

• Official touring vehicle during guided days unless otherwise specified.

• Entrances to all sites as per itinerary on guided days during guided hours

• The Squadron

• Milk & Honey Distillery

• Jeep tour in the Golan Heights

• Winery visit and wine tasting

• 24/7 assistance service while in Israel

• Information package

• Lectures by Einat Wilf, and by Khaled Abu Toameh

• Jerusalem Security fence tour

• Plus everything you see in the itinerary!

Perhaps the Time Is Now

There is never a good time to travel.

There is only the decision to go.

The Holy Land is a place everyone should see at least once in their life.

Perhaps the time for you… is now.

— Francisco
Founder, Fearless Journeys

We’re now at the point where we need to confirm who is seriously planning to join us so we can make this trip happen.

If you intend to come — or are strongly leaning yes — I’m asking you to please take a moment to complete the short Google Form below:

➡️ Complete the interest form here:
https://docs.google.com/forms/d/e/1FAIpQLSeVI1D665yT-t5Y2JryX9TLh7HXCoiUTiksl32RGcFrQgW4tw/viewform

A few important notes for clarity and transparency:

• 5 people have already signed up — we need 20 total to confirm the trip as it is currently planned

• Completing the form does NOT fully commit you yet

• No deposit is due right now

• Once we reach 20 sign-ups, we’ll follow up to collect the $1,000 deposit

• If you sign up, please be prepared to submit that deposit by February 15, once the trip is officially confirmed

• We’re intentionally waiting to collect deposits so no one has money tied up unless the trip is happening

This journey is shaping up to be something truly special — not just a visit to the Holy Land, but an experience that blends faith, business, history, relationships, and reflection in a way you won’t find on a typical itinerary.

If you’d like to take a deeper look at what we have planned, you can view the full trip itinerary below.

➡️ View the full itinerary:
https://drive.google.com/file/d/1Xi4tqyHbjnowBLf8G8KaunG6XwbeY2TP/view

And finally — if this trip resonates with you but you know someone else who needs to be in the room for an experience like this, I’d be grateful if you’d help spread the word. Feel free to forward this post or share the itinerary directly.

Thanks for walking with us as we see what this trip could become.
I’m genuinely excited about the community and conversations that could come out of this journey.

— Francisco

So tomorrow, I wanted to invite you into the conversation.

Tomorrow, Thursday, January 29 at 5:00 PM ET, we’re hosting a live Zoom info call with Yoav Rotem, our Israeli tour guide and local insider who will be leading us through the country.

Yoav lives this story every day. During the call, he’ll walk us through the journey we’ve designed, share on-the-ground perspective, and answer questions about traveling in Israel today — culturally, historically, and practically.

This trip isn’t about checking boxes or rushing from site to site.
It’s about depth.
It’s about context.
It’s about experiencing the Holy Land through real conversations with the people who know it best.

Zoom Details:
🗓 Thursday, January 29
⏰ 5:00 PM ET
💻 Live on Zoom

Whether you’re seriously considering joining us or simply want to learn more, I encourage you to join the call and bring your questions.

👉 RSVP here: https://us06web.zoom.us/meeting/register/_4eZk05RQ4Su385aOOR-Cg

Hope to see you tomorrow.

— Francisco

A 38-minute flight from Santiago, Chile to Mendoza, Argentina, flying almost directly over the Andes Mountains — some peaks rising above 20,000 feet — on a crystal-clear blue sky day. It was easily one of the most scenic short flights I’ve ever taken. Another of our travelers joined us at this stage, connecting through Santiago after flying in from the U.S., and just like that, Part 2 was underway.

From January 2–6, 2026, we spent four unforgettable nights in Mendoza, based just outside the city in the Uco Valley, at Vivacs del Plata, a historic ranch owned by the Palma family, who have stewarded this land for 250 years across multiple generations.

There are many ways to start a new year.
This felt like a special one.

If you missed Part 1 of this journey — which focused on our time in Chile, including Santiago and Valparaíso — you can read it here: Fearless Journeys Encounters Chile - Through Its People

That first chapter sets the stage for what follows below in Argentina.

Day 1 — Arrival at Vivacs del Plata: 250 Years of Stewardship

Shortly after arriving at the ranch, our gracious host Juan Cruz Palma took us on a 4x4 tour across the expansive property. Cattle grazed nearby. Horses roamed freely. The landscape unfolded with sweeping views of the pre-Andes, and beyond them, the towering Andes Mountains themselves.

At one point, we stopped on the side of a mountain — on land also owned by the Palma family — as the sun dipped lower in the sky. Juan opened a bottle of wine produced by his family — one of only 100 bottles made each year. We poured glasses, stood quietly, and simply took it all in.

The Palma family has cared for this land for centuries, and standing there made something very clear: this is not ownership — it’s stewardship.

God is good.

I understood immediately why the Palma family hasn’t left this land since first arriving 250 years ago. I didn’t want to either.

A Home, Not a Hotel

Our stay at Vivacs del Plata was a fully all-inclusive guest-home experience, and it was exceptional.

Each of us had our own bedroom and full bathroom, wonderful beds, great showers, and all meals prepared in-house. Every morning, a full American breakfast awaited us — as it did for all four mornings we spent here. From the covered back patio, we could breathe in fresh mountain air, take walks across the ranch, or simply sit quietly and admire the Andes framed in front of us — including through the large windows in the house.

The interior of the home was warm, thoughtful, and deeply comfortable — a place designed not for turnover, but for presence.

One day, I told Caroline, Juan’s mother:

“You probably don’t need anyone to tell you this, but I’m very well traveled — I’ve been to 38 countries — and you have a very beautiful piece of the planet here; one of the most beautiful I’ve ever seen.”

What struck me most was that the Palma family doesn’t take this beauty for granted. Despite centuries of family stewardship, this generation still finds joy in simply getting on a horse and riding for hours. And now, through Juan’s entrepreneurial vision, they’re opening their ranch to guests like us — without losing its soul.

By the end, we didn’t feel like guests at all.
We felt like family.

Day 2 — Wine, Serendipity, and the Power of Return

Throughout the weekend, the Palma family graciously handled all of our transportation — from the ranch to surrounding vineyards and back again — allowing us to fully relax and stay present as we moved through the Uco Valley. Saturday alone included visits to two very different wineries, each revealing another layer of Mendoza’s wine culture.

Morning: Bodega Monteviejo (Uco Valley)

Saturday morning brought us to Bodega Monteviejo, set at the foothills of the Andes in the heart of the Uco Valley. Founded as part of the Clos de los Siete project led by Michel Rolland and the Péré Vergé family, the winery blends French winemaking heritage with Argentine terroir.

As part of our stay, we enjoyed a guided tour, a tasting of four wines, and a visit into the Péré Vergé family’s private cellar, home to some of their most unique bottles. One delightful surprise? The tiny owls that live on the property — so beloved they inspired one of Monteviejo’s wine labels.

At Fearless Journeys, we don’t just visit places.
We learn from the people shaping them.

Afternoon: Back to Huentala Wines — Where It All Began

Later that afternoon, we returned to Huentala Wines, and somehow, it felt even better the second time.

For two of us, this was our second visit here — the first during our Fearless Journeys Mendoza trip in 2024. That visit turned out to be pivotal. It was at Huentala that we had a serendipitous encounter with Juan Cruz Palma — a single conversation that sparked a friendship, introduced us to Vivacs del Plata, and ultimately brought us back here for this experience.

Lunch was beautifully paced — a multi-course meal paired with five wines, elegant, generous, and relaxed. Huentala, one of Mendoza’s most recognized wine brands since the 1970s, continues to impress not just with wine, but with hospitality. The property itself — dotted with massive animal sculptures — feels like art, identity, and conversation all rolled into one.

By the end of our second winery of the day, we were happily full, a bit wine-tired, and very ready for the nap waiting back at the ranch.

This is how journeys evolve.
You return — and you go deeper.

Saturday Night — Around the Table

That evening, we gathered again at the ranch table and welcomed our local friend Luis Pujol.

Luis is a Mendoza-born architect, deeply rooted in this region, and someone who has long been involved in Argentina’s liberty movement — following and supporting Javier Milei years before he held any elected office. Conversations with Luis don’t just offer opinions; they provide context — the kind you only get from someone who has lived, built, and thought deeply about this place.

Having a local friend like Luis at the table gives us something no guidebook or tasting room ever could: an insider’s understanding of Argentina — and especially Mendoza — from the ground up.

After Luis arrived, we shared mate — Argentina’s iconic herbal drink and a deeply symbolic tradition. When shared among friends, it’s passed around the table in a single cup, one by one — a quiet signal of trust, conversation, and community.

Luis also brought a bottle of wine from a small vineyard he cultivates near his home in Luján de Cuyo. We opened it, poured glasses, and spent hours in conversation — about life, architecture, politics, culture, and everything in between. Dinner was prepared by the Palma family, and the night unfolded slowly and beautifully.

The gifts were thoughtful.
But the greatest gift, as always, was presence.

Sunday — Country Day at Vivacs del Plata

Sunday was Country Day, and it delivered.

• Three hours of horseback riding across the ranch and into its mountains

• A stop at a pond surrounded by cattle, wine opened, cheese laid out

• A traditional Argentine asado back at the ranch

As the day continued, a traditional folklore dance performance was brought directly to the home where we were staying. We could have experienced something like this in a theater or cultural venue — but instead, it unfolded right there at the ranch, just steps from the table, as part of our all-inclusive experience.

Local music, traditional dress, and powerful movement filled the space. Once again, the culture wasn’t something we went looking for — it was brought to us.

Juan’s parents rode horses with us that day — something Juan later told me had never happened before with guests, where father, mother, and son were all riding together — with us.

“I guess we’re part of the family now,” I quipped.

As the night came to a close, it felt like one of those moments that somehow exceeds even your wildest dreams — the kind you know will stay with you.

Days like this make you think: this should be an annual Fearless Journeys tradition. I’m ready to go back when you’re ready to join me here.

Monday — Wine as History, Water as Memory

Morning: Bodega Vinorum (Altieri Wines)

On our final full day, we traveled to Luján de Cuyo — joking along the way that if you stay long enough, they might crown you King of Mendoza. Those jokes were said as we were quite literally crowned and sat on what appeared to be a royal throne, with a large cup of wine in hand.

At Bodega Vinorum, wine isn’t just produced — it’s preserved. This place is a living museum, filled with presses, tools, bottles, labels, and artifacts tracing wine’s evolution across continents and generations. Local art is woven throughout, adding yet another layer of storytelling.

Our guide grew up here. Her family founded Vinorum when she was a child, and today she helps run it alongside her parents and siblings.

This isn’t corporate hospitality.
It’s generational stewardship.

Even the human touches surprised us — including a tennis racket donated by Argentine legend Juan Martín del Potro, with photos of him visiting the winery himself.

It’s one thing to taste wine.
It’s another to walk through history.
It’s something else entirely to meet the people carrying it forward.

Afternoon: Sailing Potrerillos Dam

That afternoon, we headed to Potrerillos Dam, a stunning lake tucked into the mountains just outside Mendoza.

On our first Mendoza trip in 2023, we sat nearby with coffee, simply admiring the view. This time, we went further.

Thanks to Juan, we sailed the lake on a small boat owned by his uncle and run by two friends. Six of us aboard. Midsummer weather. Impossibly blue water. Mountains in every direction. And yes — we even took turns steering.

When the sail concluded, it marked our final experience with Juan on this part of the journey. What began nearly two years ago as a serendipitous encounter had grown into something much deeper — real friendship, shared memories, and new bonds with Juan and his family.

I know we’ll see them again soon.

Juan’s mother then drove us back to the ranch via winding mountain roads, climbing above 7,000 feet. At the highest point, we stepped out, took one final photo, and let the moment settle in.

One last dinner.
One last sleep.
Then Patagonia.

Tuesday — A Grateful Goodbye

We woke one final time at the ranch on Tuesday, January 6. Breakfast once again. Morning light on the Andes. Quiet walks. Deep breaths.

Juan’s sister Sofi had spent much of the week with us — driving us to off-site locations, sharing meals, helping host alongside Caroline and the staff, including a cook and an asador. Juan’s father Fabian gave us our final ride into the city to catch our late-morning flights.

We might have been leaving, but not without so many newly created memories — with the Palma family. This is a family that has been on this land for 250 years. I can see why. I didn’t want to leave either.

From ranch life in Mendoza, we transitioned through Buenos Aires and onward to Patagonia — El Calafate.

That story is coming next.

Mendoza. Vivacs del Plata. I’ll be back.

Stay tuned for Part 3 of this Fearless Journeys adventure.

Join us in Israel this year!

Are you ready to join us for our next big travel adventure?

We’re now accepting early interest for our Biblical Business Trip to Israel (with an optional Jordan add-on) in May / June 2026. Deposits are due February 1, but for now, The first step is to fill out our short interest form so we can know if you’re planning to join us If you want to see more details, check out our itinerary here.

I have already formed a private WhatsApp group for those with strong interest in joining. And this Thursday, January 29 at 5:00 PM ET, we are hosting another Zoom call with our Israeli tour guide, Yoav Rotem. Want to join the call? Reply to this email and I’ll send you the link. There is no obligation. Tune in and see if this voyage to the Holy Land is calling your name.

You can see the holy sites.
You can walk the ancient streets.
You can float in the Dead Sea and pray at the Western Wall.

All of that matters.

But what if a journey could go deeper?

What if, in addition to standing where history unfolded, you could sit with the people shaping what comes next?

That’s what we’ve built with the Fearless Journeys Biblical Business Trip to Israel.

This isn’t a tour.
It’s not a checklist.
It’s not a bus ride from one landmark to another.

It’s a curated, immersive experience built around people — the entrepreneurs, investors, journalists, authors, military intelligence officers, security experts, and current and former government leaders who live inside Israel’s complexity every day.

In the slides below, you’ll meet some of the individuals and organizations we’ll be spending time with privately and in person.

Not in auditoriums.
Not in press conferences.
Not behind velvet ropes.

But in real conversations.

This is not tourism.
This is insider access.

I’ve been to Israel before.

I’ve stood in awe at the holy sites.
I’ve felt the weight of history.
I’ve prayed where millions have prayed before me.

But this journey is different.

This one isn’t just about where we’re going — it’s about who we’re meeting and what we’re learning.

It’s about sitting with people who don’t show up in guidebooks.
People who don’t give rehearsed speeches.
People who live the realities most of us only read about.

It’s about hearing multiple perspectives.
Asking hard questions.
Gaining context.
Understanding complexity.

And yes — it’s about faith, too.
Not as something abstract, but as something lived.

If you’ve ever wanted to experience Israel in a way that goes beyond surface-level narratives…
If you want to understand the present, not just the past…
If you want to wrestle with big questions alongside serious thinkers…

This journey might be for you.

We will be traveling from May 23–June 4, 2026, and because of the private nature of these meetings, space is extremely limited.

If you’re interested, we need to hear from you no later than February 1.

If you are considering joining us, please fill out our short interest form so we can begin delegating rooms and transportation. If you want to see more details, check out our itinerary here. It doesn’t get much better than this!

This is not tourism.
This is insider access.

This is Fearless Journeys.

Fearless Journeys is now in its fifth year—not just as a travel company, but as a community, a mindset, and a way of approaching life and work.

At its core, Fearless Journeys isn’t about checking countries off a list. It’s about helping people develop an entrepreneurial mindset—one rooted in courage, curiosity, adaptability, connection, and purpose. Everything we do is shaped by our 8 Pillars, which guide how our members think about their lives, careers, leadership, and impact.

Our group trips lean especially into a few of those pillars: mindset, action, engagement, leadership, and innovation.

Because when you remove people from their routines, immerse them in unfamiliar environments, introduce them to entrepreneurs and thinkers on the ground, and give them space to reflect, something powerful happens. Perspective shifts. Conversations deepen. People begin to see their own lives—and their own potential—differently.

Over the past few years, we’ve explored Argentina together twice—Buenos Aires, Mendoza, and Bariloche. Those trips leaned heavily into wine, culture, and city life.

This time, we returned to South America for something more expansive.

This journey had three parts:

• Part One: Chile — Santiago and Viña del Mar, with a New Year’s celebration on the Pacific coast
• Part Two: Mendoza — a deeper experience on a private ranch, focused on adventure, reflection, and community
• Part Three: Patagonia — El Chaltén and Mount Fitz Roy, El Calafate, and Torres del Paine

But before the ranch.
Before the glaciers.
Before the vastness of Patagonia…

There was urban and coastal Chile.

This newsletter recaps Part One: five nights in Chile, from December 28 to January 2. It also marked my first time in the country—making Chile my 38th nation.

And it didn’t just meet expectations.

It reset them.

Arrival

After an overnight flight from the U.S.—mine from Miami—we landed in Santiago early Sunday morning — groggy, excited, and running on adrenaline.

Almost immediately, I could tell:

This place was going to leave a mark.

Sunday: History, Art, and First Impressions

We began by grounding ourselves in Santiago’s civic and spiritual heart—Palacio de La Moneda, Plaza de la Constitución, and Plaza de Armas, where colonial architecture meets daily street life.

We stepped into the Metropolitan Cathedral, letting the quiet settle.

I always try to visit a country’s historical, political, and spiritual centers early—it reveals how a nation understands itself.

Lunch took us to Mercado Central, once a defining landmark of the city. While Santiago overall felt clean, ordered, and vibrant, this historic core has deteriorated somewhat.

That’s real travel.

You don’t just see what’s beautiful.
You see what’s changing.

From there, we headed to Bellavista, the city’s bohemian quarter—murals, cafés, artists, lapis lazuli shops. Here we visited La Chascona, the home of Pablo Neruda.

Neruda was brilliant and complicated: poet, diplomat, Nobel Prize winner, and committed communist. He died in 1973, just two weeks after Salvador Allende was overthrown.

Whatever one thinks of his politics, his cultural influence is undeniable.

His home feels less like a house and more like a dream—nautical motifs, strange angles, playful symbolism. Imagination made physical.

Travel isn’t just about seeing places.
It’s about understanding the thinkers and artists who shape them.

Later, we went up—literally.

We took the funicular and then the cable car to the top of Cerro San Cristóbal, where the city spreads beneath you, framed by the Andes.

That’s when Santiago clicked.

Later that night, after some rest back at our hotel in Las Condes, we headed to the El Golf neighborhood.

And that’s when everything came together.

The Table Is Where the Magic Happens

That evening, Kevin and I sat down with three people: one American expat and two Russian expats.

And this wasn’t random.

Months earlier, Magee (an American expat) and Konstantin (a Russian expat) had been featured on the My Latin Life podcast. I had been a guest on that same podcast a couple of years ago, so when I saw an episode about people building lives in Chile, I made sure to listen.

Then I followed them.
Then I reached out.
Then I made a note: If I’m ever in Santiago, we should meet.

That’s just what I do.

I’m a natural connector. And that instinct is exactly why I started Fearless Journeys—to build relationships with innovators around the world and then bring our community into those relationships.

Of course, the best connections always go both ways.

So when we realized we’d be in Santiago at the same time, we didn’t just say hello.

We sat down.

For four hours.

We talked about life, careers, families, travel, ideas, and dreams—over empanadas, pisco sours, wine, provoleta cheese, and steak.

We laughed. A lot.

By the end of the night, it felt like we’d known each other for years.

They shared insights about Santiago no guidebook ever could.

And I was reminded again:

Fearless Journeys isn’t about places.

It’s about people.

The real magic doesn’t happen at monuments.
It happens at tables.

Monday: Layers of Santiago

We began Monday in Las Condes, a modern, orderly part of the city—breakfast near our hotel, connected to a massive mall.

From there, we Ubered to Cerro Santa Lucía, the small hill where Santiago was founded in 1541.

Closed — and not because I picked a day it was closed. It was just randomly closed. Perhaps for a cleaning.

That’s long-distance travel. Things don’t always go as expected.
You adapt.

So we walked through Barrio Lastarria and Parque Forestal—cafés, galleries, ambient streets. A more human Santiago.

We had planned to explore Barrio Yungay and Barrio Brasil, historically important neighborhoods—but in recent years they’ve deteriorated. We passed through briefly — by car — and kept moving.

Cities change.

Next, we made our way toward Gran Torre, the tallest building in South America. But first we got out and walked. We explored a sculpture park, a public art space that lets you experience the tower not just as a landmark, but as part of the city’s living fabric. Walking through contemporary sculptures with the skyline looming above us felt like a conversation between old and new—history and ambition.

Seeing the Gran Torre from the top of Cerro San Cristóbal the day before had already given us one perspective. Standing inside it now gave us another.

From the 62nd floor, we took in sweeping 360-degree views of Santiago, with the Andes stretching across the horizon. There’s also an open-air sky deck at the top, which made the whole experience feel even more expansive—less like observing the city and more like standing inside it.

That layering of viewpoints became a metaphor for our Fearless Journeys experience in Santiago.

Lunch was at Confitería Torres, founded in 1879.

Civilization is built on institutions that last.

Later that day, we visited the headquarters of the Von Mises Institute of the Southern Cone—an institution that only began last year.

We had the privilege of seeing it in its earliest stages, still in its infancy, built largely by a group of young men in their 20s and 30s—idealistic, thoughtful, and deeply hopeful about the future of Chile.

There has been a lot of international attention on Chile’s recent presidential election. But what fascinated me most was meeting the intellectual leaders who are quietly shaping what comes next—people thinking long-term about ideas, institutions, and free markets.

The institute is named after Ludwig von Mises, one of the foundational thinkers of Austrian economics. Their work is rooted in free-market principles, human dignity, and individual liberty—and they’ve taken inspiration from places like the Universidad Francisco Marroquín in Guatemala, where I’ve had the privilege of teaching.

Standing there, in a brand-new space with a brand-new team, it felt less like visiting an organization and more like witnessing the early chapters of a story still being written.

That’s one of the great privileges of travel done this way—not just seeing history, but encountering the people who will shape the future.

That afternoon, we rested—floating in our hotel rooftop pool, staring out at the Andes.

I’ve started saying Chile feels like the most civilized country in Latin America.

I don’t say that lightly. I am well experienced across most of Latin America.

This visit confirmed it.

Learning from Local Leaders

That night, we sat down with my friend Ítalo Omegna.

I first learned about Ítalo several years ago through friends at Universidad Francisco Marroquín (UFM) in Guatemala, where I was teaching in 2021. People whose judgment I trust kept mentioning him—his curiosity, his discipline, his courage to think differently.

We followed each other online, exchanged messages here and there, and finally met in person earlier this year when we both happened to be back in Guatemala at the same time.

Now, during a Fearless Journeys experience in his home country, we were able to sit down for hours, catch up more deeply, and bring him into the fold—to engage with us, share his story, and become part of our journey through Chile.

That’s what I love most about this work: travel becomes a bridge. Relationships move from digital to personal. Conversations become community.

Ítalo grew up in Chile and spent part of his early life chasing soccer, playing semi-professionally in Argentina and Australia. Later, he worked for Disney Cruise Line as a physical trainer, traveling the world—until onboard doctors encouraged him to pursue medicine.

So he enrolled in medical school in Rosario, Argentina.

But that’s where his life took an unexpected turn.

As he studied, he began noticing a disconnect between what he was being taught—especially about politics, economics, and society—and what he had actually experienced.

So he started reading.

Mises.
Hayek.
Hazlitt.

Those ideas reshaped him.

He left med school, returned to Chile, and began engaging in public discourse—first as a thinker, then as a communicator, and eventually as a civic actor.

Today, Ítalo is a frequent radio and television commentator in Chile. He also volunteers with a nonprofit serving some of Santiago’s poorest communities. And he is the co-founder and Director of Outreach of the Von Mises Institute of the Southern Cone.

In Chile’s recent elections, socialist and communist parties suffered major defeats. Ítalo didn’t win his own congressional race—but he’ll soon be serving as Chief of Staff for another member of Congress, continuing to shape the future from inside the system.

What struck me most about Ítalo wasn’t just his intellect.

It was his joy.
His discipline.
His courage to rethink his own life.

This is what Fearless Journeys does best.

It connects people not just to places—but to people who are becoming something. His courageous leadership is inspiring.

Tuesday: From City to Valley to Coast

On Tuesday, we began the slow transition from Santiago to the Pacific.

We drove about an hour west to the Casablanca Valley for a tour, tasting, and long lunch at Casas del Bosque—a vineyard founded by an Italian immigrant family and deeply committed to sustainability.

The cool coastal air shapes this valley’s wines, and you feel that difference immediately.

We walked the vineyards, tasted thoughtfully, and then sat down for a three-hour lunch.

Every vineyard has a story.
Every bottle is an entrepreneurial journey.

Afterward, we continued another hour west and checked into our hotel in Viña del Mar—a beach town on the Pacific, nestled just north of Valparaíso.

That evening, we strolled the boardwalk, felt the South American summer air getting much cooler at night here than in Santiago, grabbed ice cream, had a simple dinner, and rested.

The next day would be the final day of the year.

Wednesday: New Year’s Eve on the Pacific

We spent the morning exploring Valparaíso—a hillside city of murals, old funiculars, and layered history.

Beautiful.
Complex.
Resilient.

Built on steep hills, Valparaíso is best discovered through its historic ascensores, which have been carrying people up and down these slopes since the late 1800s.

Crime has risen in recent years, and locals urged us to explore only during daylight.

Even in hard times, the art remains.

That says something.

From there, we drove north to the quiet seaside town of Zapallar.

After lunch overlooking the Pacific, we wandered the rocky shoreline and took a short Uber ride to a hidden crescent-shaped beach.

And that’s when we saw them.

Penguins.

In the wild.

Our Uber driver—who was from Viña—joined us. He had seen penguins before, but never from this spot.

A small group of strangers, sharing a moment of wonder on the edge of the Pacific — on the last day of the year.

That night, we returned to Viña del Mar for dinner.

Then the fireworks.

Tens of thousands lined the coast.
Music filled the air — and the streets. Latin American style.
The Pacific reflected bursts of light, even through the fog of low clouds.

A beautiful way to close an epic year.

Thursday: Resetting the Compass

On January 1, we checked out of our hotel and drove about two hours back to Santiago.

No sightseeing.
No schedule.

Just rest.

We spent the afternoon and evening quietly—resetting, reflecting, preparing.

One thing I’m always intentional about on our group trips is rhythm.

There are days when we pack in adventure—early mornings, long drives, big views, deep conversations, unforgettable moments.

And then there are days like this.

Days where we leave space.

Space to rest.
Space to wander.
Space to explore on your own.
Space to sit, journal, read, or simply be.

Some travelers use that time to relax. Others venture off the group itinerary and follow their own curiosities. And many—myself included—use that time to stay engaged with work back home.

Remote work has become a natural part of modern life, and I’ve seen how powerful it can be to blend meaningful travel with meaningful work. Many of our travelers appreciate the ability to remain connected to their careers while still immersing themselves in new cultures, ideas, and communities.

This isn’t about escaping life.

It’s about integrating it.

Fearless Journeys is designed for people who want to build, grow, reflect, and explore—all at once.

These travel experiences together also bring out random insights. There was a lot of ways we could have gone in Santiago and Valparaiso. At one point, Kevin said to me: “Let’s just walk and see what happens.”

I love that phrase. Sometimes you just have to let your curiosity take you in various directions. And when you do, the universe opens up to you. We had people helping us every step of the way. Some of those people were already integrated into our planned itinerary. Others just showed up when we needed them. When you really want to see a place for what it truly is, all the universe will conspire to help you. And on this first of our three-part trip to South America, it certainly did.

That evening in Santiago felt like a deep breath before the next chapter.

The next morning, we would fly to Mendoza.

Part Two was about to begin.

And another traveler would be joining us—stepping into the story at exactly the right moment.

What Comes Next

This was Part One.

Chile gave us art, ideas, conversation, celebration, and wonder.

Next: Mendoza.
Then Patagonia.

But those are stories for another time. I hope you’ll stay tuned.

What’s Ahead

If you missed this South America journey, don’t worry—more is coming.

We’re now accepting early interest for our Biblical Business Trip to Israel (with an optional Jordan add-on) in May / June 2026. Deposits will be due by February 1, but for now, I’m asking those who are seriously considering joining us to fill out our short interest form so we can begin planning rooms and transportation. If you want to see more details, check out our itinerary here. It doesn’t get much better than this!

If Fearless Journeys speaks to you, I’d love to have you with us, especially in the Holy Land.

And in many ways, the story of the year began before the calendar turned.

A Journey by Water — Ending 2024 & Beginning 2025

The year began on the water.

At the close of 2024, I met my longtime friend James O’Keefe in Yorktown, Virginia, where he had been slowly bringing his boat — Lucky Charm III — down the East Coast from New York toward Florida over the course of many months.

For just over a week, we traveled together through the intracoastal waterways of Virginia and North Carolina, moving south day by day, experiencing parts of America that can only truly be seen from the water — quiet fishing towns, remote marshlands, and stretches of the Outer Banks that felt almost timeless.

We celebrated New Year’s Eve 2024 in Norfolk, Virginia, bundled against the winter cold on the deck of the boat as we welcomed the new year. The days that followed were often frigid — early mornings, long crossings, and cold nights — but they were rich with reflection, conversation, and the quiet, enduring kind of friendship that forms through shared adventure.

By the first week of January, we reached the Wilmington, North Carolina area — closing one of the most meaningful journeys I’ve ever shared with a friend of more than twenty years. It was a beautiful way to end 2024… and an unforgettable way to begin 2025.

I was also glad to attend his O’Keefe Media Group West Palm Beach office opening in May and his Citizen Journalism Foundation Awards Dinner at Mar-a-Lago in November — a meaningful evening celebrating storytelling, courage, and independent journalism.

Later in the year, in November, James and I reunited again — this time in Daytona — along with two other friends, to continue the final stretch of the journey toward West Palm Beach. We didn’t quite make it all the way — engine issues (and a complete lack of wind when we needed it) slowed our progress — but we successfully guided the 63-foot mast beneath the last major navigational challenge of the voyage: the final 65-foot bridge.

We docked in Cape Canaveral, and a few weeks later James completed the final miles south. Earlier this year, he officially relocated to West Palm Beach — now just up the road from where I live — and I’m grateful to have him nearby after so many years of friendship and shared experiences.

Together, these two chapters on the water — one at the dawn of the year and one near its close — bookended 2025 with adventure, perseverance, reflection, and gratitude.

Fearless Journeys — Building Community Through Shared Experiences

Fearless Journeys remained one of the most fulfilling parts of my work and life this year, continuing to bring people together through meaningful, purpose-driven travel. This year I also upgraded the community to Fearless Journeys 2.0, putting it on a sound foundation of 8 Pillars that include:

• Mindset

• Action

• Leadership

• Innovation

• Health

• Wealth

• Giving

• Engagement

These pillars help to set the foundation for the life and career for those who choose to be part of Fearless Journeys 2.0. If you’re interested in joining us, I invite you to apply today.

Our 2025 group travel experiences included:

• Guatemala with The Currys (January)

• Dominican Republic cigar adventure with Don Doroteo Cigars (February)

• Charleston — “Building Your American Dream” (September)

• The start of our Chile–Argentina adventure, beginning in December 2025 and continuing into January 2026 — it’s where I’m writing from today!

Each journey blended culture, entrepreneurship, fellowship, history, and reflection — reminding us that travel is one of the greatest teachers and one of the most powerful ways to build community.

Looking ahead, we are preparing for our Fearless Journeys Biblical Business Trip to Israel (May 23 – June 4, 2026), with an optional add-on to Jordan & Petra (June 4–7). It will be a journey of faith, business, innovation, leadership, and history across one of the most meaningful regions in the world. Check out the itinerary here and reply to this email if you’re interested in joining us. Deposits are due by February 1.

Leading the Economic Club of Miami — Three Years of Growth

2025 marked my third full year as Executive Director of the Economic Club of Miami — a role that has been entrepreneurial, mission-driven, and deeply rewarding.

This year, we hosted 12 events, plus our second annual full-day Miami Economic Forum, featuring leaders such as:

• Michael Saylor

• Federal Reserve Board Governors Adriana Kugler and Christopher Waller

• Florida gubernatorial candidates Byron Donalds and David Jolly

• Brightline Florida CEO Patrick Goddard

By year’s end, we:

• Rolled out a brand-new logo

• Introduced our first engraved member name badges

• Launched completely redesigned website

• Continued expanding membership, partnerships, and programming

• Held 3 networking receptions and 3 educational seminars

When I first began this role, the Club had 35 members.
Today, we have over 350.

Beyond the numbers, the Club has become a place where newcomers and longtime Miamians come together to connect, learn, collaborate, and build community — and in many ways, it has helped me feel more rooted in the city of my birth as well.

A Week in Bogotá — Rediscovering Colombia

In March, I spent a week working remotely from Bogotá, Colombia — my third visit there over the past three years, and my longest stay yet.

It was an opportunity to get back on the Sunday Ciclovía and to continue rediscovering a country that has grown more meaningful to me with each return — reconnecting with friends, exploring the city at a deeper pace, and reflecting on how remarkably accessible places like Colombia (and much of Latin America) are from Miami.

The extended time I spent this year in Latin America — and later in Spain — also helped strengthen my Spanish, opening the door to deeper conversations, friendships, and cultural understanding through immersion and everyday life.

A Private Retreat on Gasparilla Island

In May, I had the opportunity to attend a private conference retreat on Gasparilla Island — a unique and luxurious corner of Florida I had never visited before.

Set among quiet coastal scenery and historic architecture, the experience was both inspiring and restorative — offering meaningful conversations with entrepreneurs and leaders in an environment that encouraged reflection, new ideas, and renewed purpose. It was a reminder that even in a state I’ve known my whole life, there are still hidden places left to discover.

A Year of Deep Time in Guatemala

Guatemala once again played a major role in my year — personally, relationally, and spiritually.

Between personal time and leading a Fearless Journeys group trip, I spent two weeks there in January. I celebrated my birthday there with my friend Josh Nadal, as we visited Semuc Champey for the first time — a breathtaking experience and a “new era of Guatemala” for both of us.

Later in the summer, I spent five weeks working from Guatemala, reconnecting with friends I’ve made over the past six years and exploring new places — including a visit to the Pan American Silver Mine and dinner with one of its top executives.

I also reconnected with students and faculty at the Universidad Francisco Marroquin, where I participated in several interactive seminars including giving a talk on the lessons from my first two books. Speaking of which, I used the time in Guatemala to work on my third book — forthcoming in early 2026!

Those weeks were unhurried, reflective, and deeply grounding — a reminder of why Guatemala has come to feel like a second home.

Pilgrimage — Walking the Camino de Santiago

Perhaps the most meaningful journey of the year was returning to Spain in mid May.

After two nights in Madrid and two nights in León, I walked 315 km over 14 days on the Camino de Santiago — carrying only a backpack, moving village to village through forests, vineyards, farms, rolling hills, and centuries-old stone towns.

Some days were challenging.

Many were profoundly peaceful.

Along the way, I met pilgrims from every continent except Antarctica — each walking for their own reason, with their own story, faith, or hope.

After finishing in Santiago de Compostela on June 1, I spent two nights there, then returned to Madrid for one final evening — closing a pilgrimage that I will carry with me for the rest of my life.

And the best part? On my first day on the Camino in mid-May, I made a commitment to pray one rosary every day during my walks. Since stepping off the Camino in early June, I have continued that rhythm. I walk every day — often multiple times a day — and I’ve prayed a rosary daily ever since. It’s best not to break good habits — especially spiritual ones. And it has been a gift to lean more deeply into prayer — with the help and intercession of our Blessed Mother.

And now here on the final day of the year in Chile — I am reconnecting with my new friend Luciano who I met on the Camino. My travels show me how interconnected the world truly is and can be.

A Year of Four Santiagos

As the year drew to a close, I realized something remarkable — in 2025, I spent time in four different places bearing the name Santiago.

One in the Dominican Republic.
One in Spain, where I completed my pilgrimage on the Camino de Santiago.
One in Guatemala — where the original name of Antigua was Santiago de los Caballeros.
And now, as I write these closing reflections, I have just spent time in Santiago, Chile during the final days of the year.

“Santiago” is the Spanish name given to Saint James, Apostle of Christ.

To have walked the Camino in his honor — and then found myself, again and again, in cities bearing his name — feels like more than coincidence. It feels like a quiet spiritual thread running through the year:

Pilgrimage.
Friendship.
Journeys of faith and purpose.
Movement toward meaning — across continents, cultures, conversations, and communities.

A year of many roads… but one direction.

Serbia, Switzerland, Chile & New Global Friendships

From Spain, I flew to Serbia, where I spoke at the Pupin Forum in Belgrade — an opportunity to connect with American and Serbian diplomats, entrepreneurs, and scholars.

My friends there showed extraordinary hospitality, and the relationships helped strengthen meaningful bridges between Serbia and Miami.

From Belgrade, I traveled to Zurich, visited my longtime Swiss friend Alexander, continued on to Lucerne and Lugano, and met up with my Swiss friend Stefan, who I first met four years ago in Guatemala. Connections made — and sustained — across continents.

The landscapes were breathtaking — the friendships even more meaningful.

I finished the trip with a short train ride to Milan and a return flight home via Madrid.

Serbia, Switzerland — and now Chile — were three new countries for me this year, bringing my lifetime total to 38 countries visited.

Loss, Friendship, and Remembering Charlie

Just as my busy fall season back in South Florida was kicking off, and as I was preparing to leave to lead my group trip in Charleston, September brought one of the most painful moments of the year — the assassination of my friend Charlie Kirk.

The world mourned. Those of us who knew him personally mourned even more deeply.

I had known Charlie for 13 years.

Later that month, I attended his memorial service in Glendale, Arizona — the largest attended memorial in U.S. history. I was grateful to sit on the floor of State Farm Stadium with friends including Bob Rubin and Maxwell Simonson, each of us tied by years of friendship and shared work through Turning Point USA.

It was a heartbreaking loss — and a powerful reminder of the fragility of life, the impact of one person’s calling, and the enduring strength of friendship. Charlie made an enormous impact on this world during his life and yet after his death, his message continues to resonate with millions more people around the world. It’s still hard to believe he’s gone. A young father of two small children, and perhaps the most gifted person I’ll ever know.

Colorado — Family, Friendship, and Discovery

A month later, in October, I spent 10 days in Colorado — a journey that touched nearly every chapter of my life.

I began in Louisville, visiting my brother Tony, his wife, and my niece and nephew, then spent time in Denver with my closest high-school friend, Sean. While there, I hosted the fourth consecutive Fearless Journeys group dinner in Denver, continuing a growing tradition of connection and entrepreneurial storytelling in the Mile High City. I was also able to include Mike O’Malley, a new friend I made along the Camino de Santiago. Once again, friendships made and strengthened across geographies.

From there, I traveled to Colorado Springs for a conference retreat — staying at The Broadmoor, visiting Garden of the Gods, and exploring the U.S. Olympic & Paralympic Museum.

Colorado Springs quickly became one of my Top 10 favorite U.S. cities.

Family, Weddings & Time Around Florida (and Georgia)

The year also gave me treasured time with friends and family across Florida — and beyond:

• I was a groomsman in my friend Christian Minor’s wedding in Pensacola (March)

• I attended my second cousin Cody’s wedding in Palatka (October), seeing nearly my entire maternal family

• I celebrated the wedding of my friend Valentin Particini in Howey-in-the-Hills (November)

• I spent several reflective days in Jacksonville earlier in the year, reconnecting with many friends there

• And over Thanksgiving, my parents and I spent several days visiting my brother Manny and his wife Tiffany in Albany, Georgia — spending time at their new home on five acres of land they continue to develop, complete with a barn full of chickens, expanding gardens, and their three energetic dogs

At Christmas time, my brother Tony and his wife and kids also visited South Florida where we were able to spend time with them once again.

These moments — full of family laughter, shared meals, everyday conversations, and peaceful time together — were reminders that some of the most meaningful journeys don’t require a passport, only presence.

Miami Moments — Sports, Leadership, and Civic Energy

November also brought two unforgettable experiences here at home in South Florida — each one highlighting Miami’s growing place on the global stage.

Early in the month, I spent two days at the America Business Forum — held at the Kaseya Center in downtown Miami and organized by outgoing Mayor Francis Suarez. I attended alongside my friend Robert Rixer and several other members of the Economic Club of Miami. The forum brought together extraordinary voices across business, politics, and sports — including U.S. President Donald Trump, Lionel Messi, Argentine President Javier Milei, Jeff Bezos, Tony Robbins, Jamie Dimon, María Corina Machado, and many others. It was an energizing glimpse into the conversations shaping commerce, leadership, innovation, and geopolitical change — and a reminder of Miami’s role as a gathering place for global ideas.

Later that month, I attended my first-ever Inter Miami CF match — and what a night to choose. Joined by my friend Max Simonson, I had the chance to see Lionel Messi play in what was the club’s final season at Chase Stadium in Fort Lauderdale before their move to Miami Freedom Park. Even more memorable — it was the Eastern Conference Championship match, where we watched Inter Miami win the title for the first time in club history — in dominating fashion. A week later, they went on to win the MLS Championship. It was an unforgettable Miami sports moment — and a special memory shared with a great friend.

Creative Work, Reading & Podcasting

This year I:

• Completed 19 books — Read my reflection about them here

• Released 14 new episodes of the Agents of Innovation podcast

• Reached 165+ episodes since 2015

Storytelling, conversation, and creative exploration continue to be among the most meaningful aspects of my work — helping connect ideas, people, and experiences across every place I travel.

Looking Ahead

I’ve now visited 48 of the 50 U.S. states — with only North Dakota and Hawaii remaining. With America’s 250th anniversary approaching, I hope to reach at least one of them soon, perhaps both. Maybe complete my 50 in America 250? We’ll see!

We also have big things in store for the Economic Club of Miami, to help take this growing club to yet another level.

As I look toward the coming year — toward Israel and Jordan, new travels, deeper friendships, and another chapter of building community in Miami and beyond — I carry deep gratitude for the people, places, experiences, and journeys that shaped 2025.

Here’s to movement with purpose.
To friendships that endure across miles and years.
To faith, discovery, adventure — and fearless journeys ahead.

Tonight, much of the world pauses to remember a moment that quietly changed human history.

In 2018, during my first visit to Israel, I stood in the shepherds’ fields outside Bethlehem. Our group opened the Gospel of Luke and read the passage describing angels appearing—not to kings or rulers—but to humble shepherds, announcing the birth of Christ.

Afterward, we looked across those same fields and simply stood still.

Right there.
In that place.
He came.

It was one of those rare moments where Scripture stopped feeling distant or symbolic and instead felt anchored—rooted in real geography, real people, and real choices. Divine history intersected with human life in the most unexpected way.

That experience has stayed with me ever since.

And you know what else I learned? Jesus wasn’t born in a stable. There’s no stables here. He was likely born in a cave. We visited one such cave where shepherds would bring their sheep in for the night. Bethlehem is an extremely small place and we certainly walked the same ground Mary and Joseph did as they searched for a place to bring forth this child.

Walking the Story — Not Just Reading It

From May 23 to June 4, 2026, Fearless Journeys will venture to the Holy Land for our Biblical Business Trip to Israel—with an optional add-on to Jordan and Petra.

This will be a journey that brings the life of Christ fully into focus.

We’ll visit a place where the story begins:

• Bethlehem, including the Church of the Nativity, marking the place of Christ’s birth

We’ll also travel to the north — to Nazareth, before following the path of Jesus’ adult ministry:

• Capernaum, where He lived

• The home of Saint Peter

• The Mount of Beatitudes, where he preached the Sermon on the Mount

• A boat ride across the Sea of Galilee

From there, we’ll make our way to Jerusalem, where we’ll:

• Walk the Via Dolorosa, following the Passion of Christ

• Visit the Church of the Holy Sepulcher, the site of His crucifixion, burial, and resurrection

This is not sightseeing.

It is immersion. On a level well beyond ourselves.

Scripture Comes Alive When You Walk the Land

One of the most powerful elements of this journey is our Israeli guide, Yoav Rotem, who brings extraordinary historical depth and cultural insight to every stop. Yoav helps illuminate the historical Jesus—where He lived, taught, worshipped, and preached—grounding the Gospel story in time and place.

From there, the rest of the story becomes one of faith.

When you walk the land, Scripture gains context. Distances make sense. Parables feel tangible. The people Jesus spoke to no longer feel abstract. You realize how ordinary—and how radical—this story truly was.

A Christmas Invitation

Christmas begins in Bethlehem.

And in many ways, this journey begins the same way—not with logistics or planning, but with a decision.

A decision to step forward.
A decision to trust.
A decision to take a leap of faith.

If this story has ever stirred something in you…
If you’ve ever wanted Scripture to feel alive rather than distant…
If you’re open to a journey that blends faith, history, leadership, and reflection—

I invite you to join us.

👉 Learn more about the Fearless Journeys Biblical Business Trip to Israel (May 23–June 4, 2026) and the optional Jordan/Petra extension.

🗺️ Check out the itinerary here! Deposits are due no later than February 1. But it’s time to announce yourself. Will you have the courage to step forward on this Fearless Journey?

This Christmas Eve, as we remember where the story began, I hope you’ll consider walking the land where it all unfolded.

Merry Christmas,
Francisco

👉 Join the Zoom call tonight – https://calendar.app.google/pFGeq6PN12gaLCPD9

Hanukkah is a story of rededication, resilience, and light. It commemorates the reclaiming and rededication of the Temple in Jerusalem and the miracle of a small flame that burned longer than anyone expected — a reminder that faith, identity, and hope can endure even in the most uncertain times.

Jerusalem sits at the heart of that story.

During my first trip to Israel in 2018, I stood near the Temple Mount — the spiritual center of Judaism for more than 3,000 years. This is the site of the First and Second Temples, the very place connected to the Hanukkah story and the Maccabees’ determination to preserve Jewish worship, culture, and self-rule. Even after destruction and exile, Jerusalem has remained a symbol of covenant, continuity, and perseverance.

Hanukkah is not just about remembering the past. It’s about carrying light forward.

That’s why tonight feels especially meaningful.

Celebrating Hanukkah Together — Live from Jerusalem (via Zoom)

Tonight, I invite you to celebrate Hanukkah with us in Jerusalem — virtually, via Zoom — alongside my friend Yoav Rotem, an exceptional Israeli tour guide with deep historical knowledge and firsthand perspective on life in Israel today. (He’ll be waking up to join us at 2:00 AM Israel time!)

Together, we’ll reflect on the meaning of Hanukkah, discuss Jerusalem and the places central to this story, and walk through the vision for our upcoming Fearless Journeys “Biblical Business Trip” to Israel. We’ll also share what makes this journey different from a typical tour and answer your questions live.

👉 Join the Zoom call tonight – https://calendar.app.google/pFGeq6PN12gaLCPD9

The Biblical Business Trip to Israel

May 23 – June 4, 2026

From May 23 to June 4, 2026, I’ll be leading a Fearless Journeys Biblical Business Trip to Israel, in partnership with Yoav.

This journey brings together the full story of Israel — past and present. We’ll spend time in Jerusalem and Bethlehem, walk through Capernum, the Mount of Beatitudes, and along the Sea of Galilee.

We’ll also experience modern Israel in Tel Aviv, one of the world’s most vibrant centers of innovation, entrepreneurship, and creative energy. It’s a rare opportunity to see how ancient foundations continue to shape a modern nation.

Along the way, we’ll visit some of the most important holy sites in the world, engage with Israeli entrepreneurs and leaders, and build meaningful relationships with fellow travelers who want to learn, reflect, and grow together.

Just as Hanukkah reminds us that a small group with conviction can change history, Israel today stands as a modern example of resilience and ingenuity — a place where light continues to shine despite adversity.

An Invitation

Whether you are seriously considering joining us in Israel, curious about the itinerary, or simply looking for a meaningful way to reflect during Hanukkah, I invite you to join us tonight on the Zoom call.

This evening is about learning, connection, and light — very much in the spirit of Hanukkah.

Chag Sameach.
May this season of light bring renewal, strength, and hope.

👉 Join the Zoom call tonight – https://calendar.app.google/pFGeq6PN12gaLCPD9

Last week, I announced something I’ve been hoping to share for a long time: the first Fearless Journeys trip to the Holy Land. (Review that announcement here)

In May 2026, we’ll explore Israel’s most meaningful biblical sites and meet with innovative entrepreneurs and business leaders who are shaping one of the world’s most dynamic economies. This unique blend is why we’re calling it a “Biblical Business Trip.”

👉 View the full itinerary, cost, and travel details here: Check out the itinerary here!

I’d also like to personally invite you to join our Israel Interest Call on Tuesday, December 16 at 7:00 PM ET.

We’ll be joined by our Israeli tour guide, Yoav Rotem, who will walk us through the itinerary, share insights about the places we’ll visit, and help answer your questions.

📅 Add the Zoom call to your calendar and join us here:
https://calendar.app.google/pFGeq6PN12gaLCPD9

If you’ve followed my travels for any length of time, you know I try to fit a boat ride into almost every trip. But the most meaningful one I’ve ever taken—and the one I can’t wait to share with you—happens on the Sea of Galilee.

It’s the same Sea where Jesus called His first disciples, where they cast their nets, where He walked on water, where Peter stepped out in faith, and where some of the most pivotal moments in human history unfolded. Gliding across those waters on a wooden boat is unforgettable—and it will be a highlight of our Fearless Journeys experience from May 23 to June 4, 2026.

This journey begins now—with the interest call. I hope you’ll join us on Tuesday evening to learn more, ask questions, and get a feel for what makes this trip truly special.

📅 Add it to your calendar and join the call:
https://calendar.app.google/pFGeq6PN12gaLCPD9

Feel free to reply here with any questions in advance—they’ll help us prepare an even better session.

Looking forward to seeing you on the call… and hopefully seeing you in Israel in May 2026!

I’m thrilled to share something I’ve been dreaming about launching for years: Fearless Journeys is officially heading to Israel from May 23–June 4, 2026, with an optional add-on to Jordan to visit Petra and several other extraordinary sites.

And this won’t be just any trip.

This will be our first-ever Biblical Business Trip — a journey that blends the ancient and the modern, the sacred and the innovative, the historical and the entrepreneurial.

Why “Biblical Business”?

Because Israel is both the Holy Land and one of the most innovative nations on the planet.

On this journey, we will:

• Stand at the most meaningful Biblical sites spanning Jewish, Christian, and Islamic history

• Walk in places that shaped civilizations

• And then… meet the modern-day builders shaping Israel’s future

Think entrepreneurs, authors, innovators, and leaders behind some of Israel’s most remarkable tech companies and social ventures. Outside of the United States, there is simply no place on earth with a greater density of world-changing ideas.

This trip gives you front-row access to that.

The Best Trip of My Life — And Why I’m Going Back

Anyone who knows me knows I’ve spent my life traveling the world.
I’ve now visited 38 countries and every journey has shaped me in some way.

But when people ask, What’s the best trip you’ve ever taken?
There is zero hesitation:

Israel, 2018.
The Israel Collective group trip I took seven years ago stands alone at the top.

What made it so special was our guide: Yoav Rotem.

Yoav didn’t just give us a tour.
He opened the country to us.
He brought us into places and conversations most visitors never experience.

Since then, Yoav and I have stayed close. Last year, we even hosted an event in Orlando for him to brief friends on the situation in Israel. I’ve always known that when the right moment came, we would build a Fearless Journeys experience together.

And now the time is right.

Why Now?

Over the past few months, life has returned to normal in Israel. Yoav is once again guiding groups safely and seamlessly. The country is entering a new phase of renewal, resilience, and economic transformation, and there is no better time to witness it.

Yoav and I combined our networks — his deep connections across Israel and the Middle East, and my Fearless Journeys community of innovators and entrepreneurs — and together we built something extraordinary.

In fact, just a few days ago Yoav told me on the phone:

“This is the best itinerary I have ever seen put together for a trip to Israel.”

Coming from the person who led the best trip of my life… that means everything.

Join Us for a Preview: Tuesday, December 16 — 7:00 PM ET

Before anything else, I want you to take time to review the full itinerary. Then I hope you’ll join Yoav and me on Zoom on Tuesday, December 16 at 7:00 PM ET.

Being on the call commits you to nothing.

We’ll walk through the journey day-by-day and take questions. And just to show you how committed Yoav is: he’s waking up at 2:00 AM in Israel to be on the call with you.

I even suggested we meet earlier so he didn’t have to wake up in the middle of the night — but he insisted this time works best for you. He wants to make sure you can join without disrupting your workday.

That’s the level of care we’re bringing to this experience.

A Few Important Notes

• Trip dates: May 23–June 4, 2026

• Optional extension: Jordan (Petra + more) June 4-6, 2026

• Deposit: $1,000 due by February 1 to reserve your spot

• Final balance: Due 60 days before departure

• Flight recommendations:

  • Many cities fly direct to Tel Aviv, with Miami and New York being ideal

  • I will be encouraging everyone to take the overnight flight from Miami on Saturday evening, May 23

  • Please do NOT book flights without first checking with me — we want everyone coordinated

We’ve taken care of everything else so you can simply show up and immerse yourself fully.

Why You Should Come

Because everyone should visit the Holy Land at least once in their lifetime.

Because travel can change you — spiritually, intellectually, emotionally.

Because you’ll meet innovators and leaders who are building peace and prosperity in the Middle East in ways the world rarely gets to see.

Because this itinerary is something truly special.

And because I genuinely believe:

There is no better way to experience Israel than on this Fearless Journeys Biblical Business Trip.

I hope you will come experience the Holy Land with us.

→ Check out the itinerary
→ Register for the Zoom call and Add It to Your Calendar
→ Reserve your spot with a deposit by February 1

Let’s walk this journey together — spiritually, culturally, and entrepreneurially.

Hope to experience the Holy Land with you.

— Francisco

In those early days, most guests were people I already knew. Then came introductions from friends, and the serendipitous moments where I’d meet someone new and say, “Hey, I host a podcast—and you’d be a great guest.” What I didn’t fully expect was how many of these relationships would grow far beyond a single interview. Many of these guests were already close friends; others quickly became so. And I’ve never stopped following their journeys.

Today, I want to share some incredible updates from several past guests—trailblazers who are now making headlines, stepping onto major platforms, and continuing the fearless journeys that first brought them onto the show.

Matt Thomas takes Chess Boxing to 60 Minutes

It was a thrill to see my friend Matt Thomas featured on 60 Minutes this past Sunday, sharing the rise of chess boxing with the world. If you listened to our conversation back in 2018 on Episode 45 of the Agents of Innovation podcast, you already know Matt’s story—but this new segment shows just how far the sport has come, thanks in no small part to him.

Matt became the first American to compete in the World Chessboxing Championships in 2018—and he didn’t just compete, he won. That victory lit a fire in him to build the sport here in the United States, and he’s been pushing it forward ever since. 60 Minutes summed him up perfectly: “a chessboxing evangelist.” That’s Matt.

He’s also a Featured Innovator in the Fearless Journeys community and even led our very first book club session in 2021—on The Alchemist, a book he recommended to me years earlier. I’ve now read it five times. That book, and Matt himself, have had a real impact on my life.

Now, with this national spotlight from 60 Minutes, the rest of the world gets a glimpse of the drive, creativity, and passion we’ve long seen in Matt. And that’s a very good thing.

Watch the full 60 Minutes segment here:

James O’Keefe hosts Madison Cawthorn

My longtime friend James O’Keefe recently welcomed Madison Cawthorn onto his podcast, My Price Is My Life, for a powerful two-hour conversation. Both of these men have been part of the Agents of Innovation journey—James on Episodes 111 and 147, and Madison on Episode 82—and it’s been inspiring to watch each of them grow, evolve, and step into new chapters of their work.

Their discussion is well worth your time. It’s raw, reflective, and filled with the kind of insights that emerge only when two people with shared history sit down and speak openly.

It’s also worth noting that Madison relocated to Southwest Florida two years ago, where he is now beginning a 2026 campaign to return to Congress—another significant step in his ongoing journey.

A special congratulations to James as well: he recently moved the O’Keefe Media Group (OMG) headquarters to West Palm Beach and hosted the first-ever Citizen Journalism Awards at Mar-a-Lago last week. I was honored to be there for such a meaningful milestone.

Watch the full episode with James and Madison here:

My Latin Life hosts James Nuveen

James Nuveen recently returned to the My Latin Life podcast—a platform where he’s become a frequent and valued guest. James brings a wealth of insight as an American expat living and working from Colombia, and often from other parts of Latin America and Europe. His global perspective and practical wisdom make every conversation with him worth tuning into.

You may remember James from Episode 132 of the Agents of Innovation podcast, and as a Featured Innovator in the Fearless Journeys community. He also led one of our live sessions last year, guiding members on how to create more freedom and mobility in their lives—a topic he truly embodies.

It’s also a fun reunion: Vance, the host of My Latin Life, joined us on Episode 143 of the Agents of Innovation podcast. Now you can listen to the two of them together.

Watch the full episode here:

Alexander McCobin gets married!

You might remember Alexander McCobin from Episode 138 of the Agents of Innovation podcast and as a Featured Innovator in the Fearless Journeys community. Just two weeks ago, Alexander celebrated a beautiful milestone—he got married! I want to extend a warm congratulations to Alexander and his bride, Camilla, and pray that God richly blesses their new life together.

As you can see, this community that has been growing over the past several years is filled with innovators, creators, and trailblazers—people who continually inspire me and so many others with the fearless journeys they’re pursuing.

If you’re not yet a member of the Fearless Journeys community, I encourage you to apply today and start connecting with leaders and doers like these. Our 2.0 level experience means you get a lot more personal attention from me and get access to even better opportunities — like our much-talked about group trips.

Speaking of trips… this is your last chance to join us for the Fearless Journeys adventure to Chile & Argentina. This three-part experience runs from December 27 to January 12, and you’re welcome to join us for one, two, or all three segments. Simply reply to this email if you’re interested. Incredible experiences await—and you never know who you’ll meet when you travel with Fearless Journeys.

Joe is emblematic of the American Dream: when the trade-offs of one place change—higher costs, higher taxes, rising crime—Americans can vote with their feet. That’s the beauty of our 50 “laboratories”: different taxes, regulations, and cultures. If you’ve outgrown one place, you can build a life in another (and yes, still cheer for the Yankees in a city that once booed them).

I even know a British friend who moved to Miami for opportunity, then on to New York for media and PR—proof that in America, pathways aren’t linear, they’re abundant. Different strokes for different folks.

My new connection with Joe is exactly why I love to travel and attend events. You never know who you’re going to meet, what perspectives you’ll gain, or what opportunities might unfold from a simple conversation. That’s one of the core reasons we incorporate travel experiences into the Fearless Journeys community—not just for adventure, but to intentionally connect with local entrepreneurs and expand our networks in meaningful ways.

Joe and I kept talking about that kind of mobility, mindset, and opportunity—so we hit record. I joined him on his Low Country Lunatic podcast to dig into the American Dream, innovation, and Fearless Journeys. You can listen on various podcast apps like Apple Podcasts here and Spotify here.

You can also watch the conversation below on YouTube:

In our conversation, we covered a wide range of topics:

• 🇺🇸 Charleston & the American story — I shared why Charleston is one of my favorite American cities and reflected on visiting Fort Sumter just days after my friend Charlie Kirk’s assassination. It was a solemn, meaningful moment that tied our nation’s history to the present.

• 🙏 Remembering Charlie Kirk — I spoke about my 13-year friendship with Charlie, the shock of his death, and the powerful way his legacy continues—through international tributes, local memorials, and a surge of engagement with Turning Point USA. I also highlighted his remarkable intentionality, like his weekly tech-free Sabbath.

• 💡 Entrepreneurship & innovation — We discussed how America’s rule of law, property rights, and state-by-state diversity create fertile ground for entrepreneurs. I shared examples like the iPhone’s ripple effect on innovation, and why intentional time management and discipline are core traits of successful builders.

• 🌍 Travel, perspective & opportunity — I explained why I’ve traveled to 37 countries and how those experiences shape my entrepreneurial mindset. Travel expands context, sparks ideas, and reinforces why the U.S. remains the best place to turn ambition into reality.

• 🧭 Fearless Journeys — I described how our community blends adventure with entrepreneurship: online sessions with featured innovators, in-person dinners in cities like Miami and Denver, and curated group trips that connect members with local entrepreneurs around the world.

• ⚡ Faith & innovation in the age of AI — We talked about using technology with purpose, keeping humanity at the center, and setting personal guardrails to make tools like AI work for you—not the other way around.

This was a rich conversation that wove together history, personal stories, and practical insights for anyone building something in today’s world. I hope you’ll tune in!

A Fearless Journeys Dinner in Denver

On October 7, we gathered an incredible group around the table at Bon Ami, a French restaurant in Denver’s Washington Park neighborhood, for our fourth annual Fearless Journeys experience in Denver — and what a table it was.

The evening brought together people from a variety of professional and personal backgrounds, each bringing their own perspectives and intentions to the conversation:

• Sean Gross, a Fearless Journeys Featured Innovator and longtime friend, joined us from the loan and mortgage industry. Sean is featured in my new book The Heart of the American Dream and reminded us of our first entrepreneurial venture together—an auto detailing business we started in high school nearly 30 years ago.

• Helen Mitchell, in the oil & gas industry, reflected on a childhood spent in places as varied as Colorado, London, Oklahoma, and Australia. Her global outlook has shaped her journey, and she’s been a regular collaborator with Fearless Journeys here in Denver for three years running, as well as joining our 2023 group trip to Colombia.

• Jeff Salzenstein, a former top-100 tennis pro turned performance coach and speaker, shared vivid stories from his playing days—including taking the first set off then–No. 2 Michael Chang at the 1997 U.S. Open. We connected two years ago through mutual friends like Jean-Yves Aubone, also featured in my book.

• Michael O’Malley, from Colorado Springs, recently completed four years on the City Council after more than 40 years in military intelligence. We met earlier this year while walking the Camino de Santiago—he walked the entire French Way, over 700 km in 35 days.

• Brian Smith, an accountant and longtime friend from my Intercollegiate Studies Institute days, brought humor and insight from years of managing books for small businesses as he prepares to take over his family’s firm.

• Jeff Hunt, Denver talk radio host, writer, and leader in faith and public policy circles, has been a friend and collaborator for over a decade.

• Keri Pearson, new to the table, shared about her work in home care and her excitement to get more involved with Fearless Journeys.

Some of these relationships stretch back 5, 20, even 30 years. Others were brand new that night. But that’s exactly the point of Fearless Journeys:

🤝 Bringing people together from different industries and walks of life.
🌱 Building lasting connections that transcend time and place.
🎉 Celebrating each other’s wins.
💪 Leaning in to support one another through shared challenges.

By the end of the night, one attendee told me, “That was one of the most fun dinners I’ve had in a really long time.”

📝 How to Join Us

Experiences like our various meet-ups in cities like Denver, group trips to Charleston and our upcoming group trip to Chile and Argentina (in December & January) are exclusive to Fearless Journeys 2.0 members.

If you’ve been thinking about joining us — now is the time. Spots are limited, and flight availability will tighten as we approach the holidays.

✉️ Simply reply to this email to let me know your interest or intentions to join. I’ll personally walk you through the next steps and share with you our planned online, in-person, and group trip plans.

👉 Apply to join Fearless Journeys 2.0 if you’re not yet a member.

From ringing in the New Year over the Pacific Ocean to horseback riding beneath the Andes and standing face-to-face with the Perito Moreno Glacier, this trip is designed to push your boundaries, deepen your relationships, and give you fresh inspiration for the year ahead.

And here’s the best part:
👉 If you decide to join us, I already have all the flights picked out for you.
No stress. No guesswork. Just pack your adventurous heart and say yes.

🌟 Highlights of the Journey

🇨🇱 Part 1: Santiago & Valparaíso (Dec 28 – Jan 2)

• Explore vibrant Santiago and coastal Valparaíso.

• Ring in the New Year with one of South America’s most spectacular fireworks displays over the Pacific.

• We all also include a lunch experience at a vineyard and coastal adventures!

🇦🇷 Part 2: Mendoza (Jan 2 – Jan 6)

• Stay on a private ranch surrounded by the Andes.

• Horseback rides, 4×4 adventures, sailing, and vineyard tastings.

• Authentic Argentine asados and live folklore by the fire.

❄️ Part 3: Patagonia Expedition (Jan 6 – Jan 11)

• Witness Perito Moreno Glacier up close (with optional glacier trek).

• Trek Mount Fitz Roy and road trip through Torres del Paine.

• Explore the Petrified Forest and its prehistoric wonders.

Optional Add-On:
🇦🇷 Buenos Aires Extension (Jan 12 onward) — Tango, plazas, world-class dining, and cultural immersion in one of the world’s great cities.

📝 How to Join Us

This experience is exclusive to Fearless Journeys 2.0 members.

If you’ve been thinking about joining us — now is the time. Spots are limited, and flight availability will tighten as we approach the holidays.

✉️ Simply reply to this email to let me know your interest or intentions to join. I’ll personally walk you through the next steps and send you the itinerary I’ve already prepared.

👉 Apply to join Fearless Journeys 2.0 if you’re not yet a member.

Why This Trip Matters

Travel has the power to change how we see the world — and ourselves. Whether it’s hiking in Patagonia, watching fireworks over the Pacific, or sharing conversations around a fire pit under southern skies, this is more than a trip.

It’s a chance to reset, recharge, and reimagine what’s possible for your life and business in 2026, alongside a community of curious, driven, and fearless fellow travelers.

Our home base for the weekend was the Indigo Inn, a charming boutique hotel tucked into the heart of the historic district. Its courtyard quickly became our gathering place — a space where conversations and community began to form.

Our core group of five shared the entire weekend together: Stephanie (Nashville), Arlie (Chicago), Kevin (St. Petersburg, FL), Doug (Orlando), and myself (South Florida).

Thursday, Sept 11 – Arrival & Kickoff

As participants arrived, we settled into the Indigo Inn and took in the charm of the surrounding historic streets. I had flown in that morning from Fort Lauderdale and shared an Uber with Arlie, who had just landed from Chicago — a fitting reminder that Fearless Journeys is as much about connection as destination.

By late afternoon, we circled up in the courtyard for our Welcome Orientation. Journals embroidered with the Fearless Journeys logo were placed in each participant’s hands — and those who did not yet receive their Chart My Course journal and signed copies of The American Dream is a Terrible Thing to Waste were also given those. These were tools not just for the weekend but for the journeys each member was already pursuing.

That evening, we made our way to the Harbour Club at WestEdge, a modern venue with sweeping views, for The Charleston Meeting. There, 200 civic leaders gathered for a reception and keynote talks. I spoke on The American Dream is a Terrible Thing to Waste, drawn from the title of my first book — but before turning to those entrepreneurial lessons, I began with a personal tribute to my longtime friend, Charlie Kirk, who had been assassinated just the day before.

It was not easy to speak those words aloud, but it felt necessary. Charlie was not only a public figure but a friend of 13 years, and his entrepreneurial brilliance, courage, and faith shaped countless lives, including mine. I have written about my grief, our friendship, and what Fearless Journeys means in light of his passing in my previous newsletter, which you can read here: Grief, Friendship, and Fearless Journeys.

Sharing that tribute with the Charleston audience was, for me, another form of healing. And it set the tone for our weekend together: that the American Dream is not an abstraction, but something we live out in our own lives — often through challenge, loss, and resilience. The American Dream is also about sacrifice, learning by doing, taking action, and being filled with love and passion. These were traits that embodied both the life and death of Charlie Kirk.

Among those gathered was Jerome Hudson, a fellow Fearless Journeyer from Jacksonville, FL, who had spoken at the Charleston Meeting before. Jerome was the one who first recommended me as a speaker to the organizers — a perfect example of how this Fearless Journeys community uplifts one another, opening doors and creating opportunities that ripple outward. His simple act of generosity helped spark the idea of building this entire Charleston trip.

After the meeting, the group dined at Husk, a restored Victorian mansion now serving inventive Southern cuisine. Over plates of fried chicken and heritage grains, Doug Pestana — co-founder of LegalMente AI and a Featured Innovator in the Fearless Journeys community (previously featured on Episode 160 of the Agents of Innovation podcast) — guided a conversation on AI and Your Legal and Entrepreneurial Dreams.

Doug gave concrete examples of how artificial intelligence should not be feared, but embraced as a powerful tool — one that can amplify your work, free up time for higher-level thinking, and ultimately elevate your career. For our group, all of whom work in the legal profession in some capacity, the discussion was both practical and inspiring, helping them see AI not as a threat but as an ally in building their own American Dreams.

Friday, Sept 12 – Vision & Values; Impact & Action

We began the morning with breakfast in the open-air courtyard of the Indigo Inn, enjoying a simple but meaningful start together. From there, we began our walking tour on the Fearless Journeys Entrepreneurial Trail in Charleston. We began with a short five-minute walk to the Charleston City Market, where we breezed through stalls filled with local crafts and paused to admire the intricate sweetgrass baskets — a craft preserved by Gullah families for generations.

After this morning stroll, we settled into Carmella’s Café, a bright and welcoming spot near the Market, for our first group coffee and conversation. Over cups of coffee, each participant shared a glimpse of their own American Dream. This moment set the tone for the day: Fearless Journeys trips aren’t just about sightseeing, they are about bridging connections, creating space for intentional reflection, and learning how to help each other along the way.

From there, we continued along the Charleston Entrepreneurial Trail. At the Old Exchange & Provost Dungeon (1771), we confronted the paradox of a site that once served as a customs house and gathering place for revolutionary ideals, yet also where enslaved people were bought and sold and prisoners were held in its dungeon. It is both a cradle of democracy and a reminder of injustice.

At Rainbow Row, the pastel-colored Georgian townhouses told a story of visionaries who revived what others had abandoned. By the early 20th century, these homes were in ruin, until preservationists like Susan Pringle Frost — Charleston’s first female real estate agent — spearheaded their restoration, sparking a movement that revitalized the city’s historic charm.

At the Heyward-Washington House (1772), we connected with the legacy of Thomas Heyward Jr., one of the 56 signers of the Declaration of Independence. The home is also remembered for hosting President George Washington during his Southern tour in 1791 — a detail that gave profound resonance to our reflections on the American Dream.

Just a short walk further, we paused at a park to admire the statue of George Washington, commemorating that very visit. Standing before it, we were reminded that Charleston itself was a stage for the earliest chapters of America’s experiment in freedom and enterprise.

We also slipped into Stoll’s Alley, one of Charleston’s most hidden passages. Just wide enough for two people to walk shoulder to shoulder, it was once used for secret gatherings and quiet exchanges away from the bustle of East Bay Street. Today, with its cobblestones and flowering window boxes, it’s one of the city’s most charming reminders that history often hides in the narrowest of places.

Just before lunch, we strolled down to The Battery & White Point Garden, a scenic promenade lined with antebellum mansions and shaded by live oaks. Once a site of military defense, today it’s a place of reflection — cannons, monuments, and harbor views reminding us of both Charleston’s resilience and its role in America’s struggles, from the War of Independence to the Civil War between the states.

From there, we made our way to Poogan’s Porch, a charming Victorian townhouse turned restaurant named after a neighborhood dog who once lounged on the porch. Known for its Lowcountry classics like she-crab soup and fried green tomatoes, it was the perfect backdrop for conversation with our guest, Claire Kittle, Executive Director of Talent Market.

Claire shared insights from her work connecting talented professionals with nonprofit public policy organizations and why she chose to work remotely from Charleston over a dozen years ago. Her reflections sparked dialogue about how aligning personal values with professional work is itself a pursuit of the American Dream. Our group left not only well-fed but also inspired by Claire’s reminder that careers built with intention can ripple outward to shape institutions and society.

We then visited the Nathaniel Russell House (1808), a mansion whose famed free-flying staircase is considered an architectural marvel. Yet the home also represents a dual narrative: Nathaniel Russell built his fortune through international trade, including the trade of enslaved people. It stands as both a testament to prosperity and a reminder of injustice.

We also made a brief stop at the Cathedral of St. John the Baptist, Charleston’s French Gothic Catholic cathedral with soaring spires and intricate stained glass. A wedding was about to begin at 3:00 p.m., so we only popped our heads in for a quick glimpse — but even that moment was enough to take in its beauty and grandeur before continuing on.

After wrapping around the scenic campus of the College of Charleston and strolling by Marion Square, our final stop was the Mother Emanuel AME Church (1816), one of the most historically significant Black churches in America. Founded by free and enslaved African Americans, it became a place of faith, resistance, and resilience for over two centuries. It played a role in the Civil Rights era and has long been a hub for community leadership. Yet it is also remembered for tragedy: the 2015 mass shooting in which nine members, including Pastor Clementa Pinckney, were killed during a Bible study. In the aftermath, family members of the victims publicly offered forgiveness to the shooter — an extraordinary act of grace that stunned and inspired the nation. It’s a reminder that violence doesn’t have to be met with violence, but with forgiveness and reconciliation.

It was a solemn place to end our afternoon walk, reminding us that the American Dream must be for all — and that building it requires courage, truth, and compassion. The American Dream isn’t perfect or perfectly attained. There have been and will be challenges along the way. How we navigate this — including ethically — is all a part of what we can each incorporate on our own fearless journeys.

It was during our break after the trail that we were joined by two more friends: Roland, who now calls Charleston home after years in California and Texas, and Rick, a longtime friend I hadn’t seen in over 20 years who had lived in Maryland and North Carolina before recently settling in Charleston. Both added fresh perspectives, joining some of us for conversations on an outdoor patio overlooking Marion Square that carried our reflections deeper.

That evening, our group dined at Frannie & The Fox, a chic spot with delicious Italian cuisine. The evening’s reflections were rich: what did we learn today, and what actions might it inspire in our own journeys? Among those gathered was Rick, rejoining us for dinner.

Afterward, we took to the town and spent most of the rest of the evening at The Rooftop at The Vendue, sipping cocktails with incredible views of Charleston in the cool evening air. There, we were joined once again by Jerome, adding his voice to the conversation as the city lights glimmered around us.

On our way back to the Inn, the group discovered a speakeasy where we gathered for one final night cap as our fellowship with one another increased even more. It’s these moments that aren’t planned on an itinerary but are brought about by the unique gel of personalities that seem to unexpectedly enliven every Fearless Journeys group trip.

Saturday, Sept 13 – Defense of the American Dream

Saturday began with an early morning walk to Liberty Square, where we boarded the ferry to Fort Sumter, the site where the Civil War began in 1861. The 45-minute ride across Charleston Harbor was beautiful — cool and breezy, even a little chilly for some of us. At Fearless Journeys, we always look for ways to get our groups out on the water when possible. It does something to the soul, stirring both peace and reflection, and this morning was no exception.

Ours was the first group on the island fortress that morning, and park rangers invited volunteers to help raise the massive U.S. flag. One of our members, Roland, stepped forward. The symbolism of that act was not lost on us.

But just as the flag was raised, that same flag was lowered to half-mast — by presidential order — in honor of my longtime friend, Charlie Kirk, who had been assassinated only days earlier. The irony of the moment was striking. We stood where political violence once ignited a war that claimed more than 700,000 American lives, and now we found ourselves here again in the days after another tragic act of political violence that has stirred the nation.

When we returned to shore, we made our way to Fleet Landing, a converted naval facility turned casual waterfront restaurant, where we continued the conversation over fresh seafood and Southern fare. Together we reflected on the hope that this moment will not lead to more violence, but rather to greater healing. So far, it has. As I write this, it is just over a week since I attended Charlie’s funeral in Arizona — and more than two weeks since our Charleston trip. In that time, there has been no retaliatory violence, only candlelight vigils, prayer services, and even baptisms inspired by Charlie’s life and legacy.

Standing on that ground at Fort Sumter and then discussing it together over lunch reminded us that the American Dream has always required defense, sacrifice, and courage — and that our own fearless journeys call us to rise to the same challenges in our time.

The afternoon carried us across the Arthur Ravenel Jr. Bridge to Patriots Point, where we explored the USS Yorktown (CV-10), a WWII aircraft carrier nicknamed The Fighting Lady. Commissioned in 1943, it played a pivotal role in the Pacific theater, later saw service during the Vietnam War, and even recovered Apollo 8 astronauts after their return from the moon.

Walking its decks gave us a sense of the scale: nearly 900 feet long, with the capacity to carry more than 90 aircraft and a crew of over 3,000 at its peak. Exhibits showcased everything from fighter planes to the daily life of sailors who once called the ship home. Standing there, surrounded by such immense engineering and history, was a reminder that the American Dream has also been defended on the seas — with innovation, sacrifice, and courage at massive scale.

That evening, we gathered at The Ordinary, an upscale seafood hall housed in a 1920s bank. Over dinner on the outside patio of this cool and pleasant evening , we were joined by one of Roland’s local friends, Joseph, originally from Puerto Rico. Having lived in several places across the U.S., Joseph had only recently settled in Charleston, bringing with him both fresh perspective and a deep sense of purpose. His life story is a testament to the American Dream.

Joseph shared openly about how his life had been transformed when he leaned more fully into his faith. Today he is married, raising a child, and building a career that fills him with meaning.

This conversation was unexpected, but it added extraordinary value to what we were already experiencing together in Charleston, a city dubbed “The Holy City,” in part because of its sheer number of historic church steeples.

Joseph’s story of faith and fulfillment resonated with the group, sparking dialogue about how the entrepreneurial mindset is not only about ventures and investments but also about the intentional pursuit of meaning. It was a reminder that the greater purpose behind Fearless Journeys 2.0 is to take our conversations “higher” — to reflect not just on what we are building, but why — and the importance of having people to share our journey with.

In that moment, our community was able to learn not only more about Charleston, but also more about each other, and more about the deeper callings that guide our lives.

The night didn’t end there. We joined Mike Brown, host of the Pleasing Terrors podcast, for a Charleston Ghost Tour. Under lantern light, we wove through cobblestone streets and narrow alleys as Mike shared stories that blended history with the supernatural. We paused in front of centuries-old churches, graveyards, libraries, courthouses, and shadowy corners where legends of restless spirits have been passed down through generations.

Charleston is a city where beauty and tragedy often coexist, and the ghost tour gave us a deeper glimpse into that paradox. Each tale reminded us that beneath the pastel facades and elegant homes lies a history marked by fires, plagues, wars, and personal heartbreaks — and the enduring power of storytelling to keep those memories alive.

What made the tour especially memorable was Mike’s ability to draw connections between the city’s past and the human emotions that still echo today — fear, loss, resilience, and hope. It was less about being spooked and more about encountering Charleston’s layered soul after dark.

Finally, we ended the evening at Kaminsky’s Dessert Café, indulging in ice cream, pies, and cakes — one last sweet moment of fellowship before returning to our inn.

Sunday, Sept 14 – Reflections & Departures

On our final morning, it was time to say goodbye to each other, one by one. We said our farewells not with endings, but with a sense of continuity — that Fearless Journeys doesn’t stop when the trip ends.

For me, seeing Rick again after 20 years — and seeing Arlie, Doug, Jerome, Kevin, Roland, and Stephanie back on an additional Fearless Journeys group trip — were powerful reminders of that truth: Fearless Journeys is about more than the destinations. It’s about the relationships — old and new — that continue long after we leave a city behind.

✨ Closing Thought:
Charleston gave us more than a weekend. It gave us a stage on which history, community, and vision converged. Each participant left with stories, reflections, and tools to keep building their American Dream — and with the reminder that none of us journeys alone.

Join Our Next Adventure

Ready to experience what it’s like to travel with a purpose-driven community? Come with us on an epic Fearless Journeys group trip to Chile & Argentina — join one, two, or all three segments:

• Santiago & Viña del Mar (Chile): Dec 28 – Jan 2

• Mendoza (Argentina ranch experience): Jan 2 – 6

• Patagonia (Argentina & Chile: hiking + glaciers): Jan 6 – 12

To participate, you’ll first need to join Fearless Journeys 2.0 — our member community that unlocks curated experiences, intentional connections, and insider access. This trip will be a perfect way to ring in the new year!

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When I first planned this trip, it felt unusual to start on September 11th. That date holds deep meaning for all of us who lived through it. It’s hard to believe 24 years have now passed. Still, there was a reason we chose those days.

Earlier this year, I was invited to speak at The Charleston Meeting, a civic forum that gathers monthly to hear from a range of voices. My friend — and fellow Fearless Journeys member — Jerome Hudson had spoken there before and recommended me. The organizers asked me to share insights from my first book, The American Dream is a Terrible Thing to Waste. In many ways, it felt fitting to reflect on the American Dream as we marked another September 11.

That invitation sparked the idea of building a full Fearless Journeys 2.0 group trip around it. Charleston has long been one of my top five American cities. Though I’d only visited briefly on two prior visits, I knew its history, architecture, and spirit would provide the perfect setting for an inspiring three-night experience.

So the plan came together: four members joined for the full weekend, several others dropped in for parts, and I prepared both to lead the group and to address 200 people at The Charleston Meeting.

But then, everything changed.

The Call No One Wants

On September 10, around 2:49 p.m., as I returned home from errands, my phone lit up with messages. The news: my longtime friend Charlie Kirk had been shot on a campus.

Thirty minutes later, I made the mistake of watching the horrific video — Charlie struck in the neck, blood pouring as bystanders screamed. I fell to my knees and prayed, pleading to God:

“Please don’t take Charlie. Please don’t take Charlie. Not now. Not now.”

Deep down, I knew it would take a miracle for him to survive what I just saw on video. Within an hour, confirmation came. Charlie was gone. I broke down in tears.

In those first hours, friends reached out by text and calls. Some I couldn’t answer. I was grieving — and yet also preparing to pack and lead a trip. One trip participant, knowing of my friendship with Charlie, texted that she would understand if I canceled.

But without hesitation, I told her: the trip was on.

And I’m glad it was.

Flags at Half-Mast

The next morning, September 11, I drove to Fort Lauderdale airport for my early flight. As I entered the garage, I saw the first flag that was at half-mast for Charlie, as the President had directed the night before. I broke down crying in my car. For days, whenever I was alone, tears returned — especially with the image of that video seared in my mind.

As a Christian, I know Charlie is with the Lord. He lived his life anticipating that moment. Yet I still wept. He had already given so much in just 31 years — and had so much more left. His wife and two small children now carry on without him. A movement and a nation lost a fearless leader. I lost a friend.

Therapy in Unexpected Places

My early flight from Fort Lauderdale was delayed for hours. During that wait, John McCormack, a longtime friend and reporter for The Dispatch, reached out asking for an interview. I had the time, so I called. For 45 minutes I shared stories of Charlie, personal memories, and reflections on his influence.

I wept through parts of the call. John was patient, kind, and consoling — reminding me that good journalists often serve as quiet counselors when tragedy strikes. That conversation was therapeutic, and I’m grateful. You can read John’s article here.

The flight delay, frustrating on the surface, was a gift. It allowed me to process grief aloud instead of bottling it up. Sometimes God gives us those spaces in ways we don’t plan.

Arrival in Charleston

When I finally landed in Charleston that afternoon, I met up another participant, Arlie, who had landed around the same time. We shared an Uber to our hotel. Soon the rest of the group gathered in the courtyard of the Indigo Inn, a charming spot in the historic district. I set the tone: Fearless Journeys trips are about bonding, new relationships, and taking steps toward our own American Dream.

That evening we attended The Charleston Meeting together, where I was one of the keynote speakers. Before diving into the 10 characteristics of the entrepreneur from my book, I began with a tribute to Charlie — his life, legacy, and entrepreneurial brilliance. Speaking those words aloud, even through tears, was another form of healing. And I hoped — and think I succeeded — in personalizing Charlie’s story for many who may have only known him through screens.

History, Violence, and Reflection

I will have more to share about our full group trip to Charleston later, but I want to give you insight into one activity during our time there.

On Saturday morning, September 13, we ferried to Fort Sumter, where the Civil War began in 1861. Ours was the first group to arrive. Park rangers invited volunteers to raise the massive U.S. flag, and one of our members, Roland, stepped forward.

But soon after, the flag was lowered — by presidential order — in honor of Charlie.

The symbolism struck me hard. We stood where political violence once ignited a war that killed 700,000 Americans. And here, in 2025, we lowered our flag for my friend — another victim of political violence, in a place sacred to the American Dream he spent his life fighting for.

At lunch, our group reflected. The parallel was haunting.

May Charlie’s death never lead to further violence. May it instead inspire healing. As of this writing, two days after his funeral (which I attended and will write about later) and nearly two weeks after his death, it appears the healing has begun. There has been zero violence. Instead, the moment has been met with candlelight vigils, prayer services, and even baptisms, inspired by Charlie’s life and death.

Charlie never hated those who opposed him, despite having many “enemies.” He chose persuasion, dialogue, and courage. Our culture is sick with hate. We can honor him by rejecting it. And so far we have.

As Bill Maher noted recently in conversation with Billy Corgan, Charlie’s assassination is a warning for America. We must keep our discourse civil, not deadly. Differences of opinion should not divide us, let alone kill us. In this spirit, I encourage you to build a bridge today — and then another tomorrow. You can watch Bill Maher’s podcast here.

Charlie’s Enduring Voice

In the days since, I’ve been honored to share more tributes. National Review invited me to write about Charlie, which you can read here.

I also urge you to watch Charle’s final interview with entrepreneur Andrew K. Smith, recorded on his final hours on earth.

Just hours before his death, Charlie spoke not about politics but about life, entrepreneurship, and faith.

Some of his parting wisdom:

• “An entrepreneur at its core is a problem solver against the tide.”

• “The reward is actually the process — the process of solving problems.”

• “All feedback is an opportunity to get better.”

• “This too shall pass” — whether in hardship or success.

• Romans 8:28: “We know that all things work for good for those who love God, who are called according to his purpose.”

Those words carry even more weight now.

Moving Forward

As I write this, I have just left Glendale, Arizona — where, on Sunday, I attended Charlie’s memorial, the largest funeral in America history in a stadium that holds more than 70,000 people with overflow of 20,000 in the arena next door. Tens of thousands of more waited outside hoping to get in. That scale reflects the impact he made. But it wasn’t a funeral. It turned into a revival. And I am grateful to have been a witness to this true turning point for America.

Leaders, pastors, entrepreneurs, and friends gathered to pay tribute to him. While he made an impact on the world, for me Charlie was, first and foremost, my friend. And we shared many friends including with Featured Innovator Bob Rubin (pictured in the center above) who has also personally known Charlie for over a decade.

The candlelight vigils, prayer gatherings, and even baptisms happening worldwide in his honor testify to the man Charlie was — husband, father, leader, mentor, believer.

Charlie Kirk was a gift from God to all of us, even if only for 31 years. He produced so much good in so little time. He taught me more than I can capture here — not just through his words, but through how he lived, and yes, through how he died.

His legacy will not fade. America honors him. And on the Fearless Journeys group trip in Charleston, among friends, I found that this group travel experience provided both distraction and therapy, reminders that grief shared is grief lightened, and that journeys taken together can carry us when we cannot walk alone.

***

If you’re ready to see what being part of a community that travels together is all about, I invite you to consider joining us on what will be an epic Fearless Journeys group trip to Chile and Argentina. We will have three parts (Santiago & Vina Del Mar, Chile, December 28 - January 2; an adventure on a ranch in Mendoza, Argentina, January 2-6, and a hiking and glacier experience in the Patagonia region of Argentina & Chile, January 6-12). You can join us for one, two, or all three parts.

But first — if you want to be part of this once-in-a-lifetime trip, you must join Fearless Journeys 2.0. Membership gives you access to our community, upcoming experiences, and insider connections. We have built so much more intention into the 2.0 version of Fearless Journeys and we hope you will be a part of it.

👉 Apply today to become a member of Fearless Journeys 2.0. And don’t hesitate to reply to this email with any questions or comments. I hope to see you soon!

And if you’re already a member of Fearless Journeys 2.0 and are reading this, please reply to this email for the details on how to join the trip.

It’s always surreal to be getting on a plane on September 11th, as so many of us lived through that horrific day. It’s more unbelievable that 24 years of time have passed since.

But yesterday, another great tragedy hit our nation with the assassination of Charlie Kirk. And it hit closer to home.

Charlie Kirk was a close personal friend for the past 13 years. In fact, he has been a fellow traveler with you on this email list for Fearless Journeys.

With all that he has going on, I was a bit surprised when he texted me last year asking if I wanted to go on his radio show to talk about Adam.

I looked at my text: “Adam?”

Then it hit me. Charlie had received my email about the passing of one of the Featured Innovators in the Fearless Journeys community, Adam Andrzejewski, who had also been on my Agents of Innovation podcast in the summer of 2020. Charlie was personal friends with Adam, he saw my email, and told me: “I’ve been looking for the right guest. I think you would do a great job.”

I was honored. Less than a month later, on September 26, I was in Arizona and joined Charlie in studio. I was on the air with him for two segments lasting a total of about 20 minutes. He had also arranged for me to get a private tour of the amazing TPUSA facilities in Arizona, which I received before going on air. I said to him: Alluding to everything he has built, I asked him: “Did you ever think this was possible when we met 12 years ago?” He just gave a big Charlie smile.

We had a chance to chat for a few minutes off-air both before and after the segment, but I believe that’s the last time I saw my friend in person.

Though it hardly feels like it. We communicate a lot and have traded scores of texts before and after the election and about many topics since.

The thing I was most encouraged about Charlie in the past few years and more so in the past number of months was his transition away from merely political topics and diving more deep into his faith publicly. In addition to that, I loved seeing him use his platform to give simple life advice to young people about getting married, having kids, building the characteristics of courage, a work ethic, and being financially responsible. While I never strayed away from debating with him on a number of topics, I was proud of Charlie and told him so often. But I wish I could tell him one last time.

Charlie had a heart for the American Dream but he also had a giant big heart for all people. There will be a big hole in this country of ours for a long time knowing what we’re missing. But I will thank God for the short span of time he gifted Charlie to us.

***

It’s been a rough less than 24 hours trying to process this, but last night I wrote these words below to share with so many friends who were reaching out to me.

Some of you may have already seen this posted on my social media, but I thought I would share it here with you as well.

***

REMEMBERING MY FRIEND CHARLIE KIRK

Seeing my good friend Charlie Kirk assassinated today doing one of those things that used to be considered "American" -- freely debating one's ideas with others -- was truly horrifying.

It’s unreal. It’s one of those things you always know is possible but can’t believe it when it actually happens.

Charlie was a devoted follower of Jesus and I know today He is with him. That is what gives me solace.

But many of us lose Charlie as a friend on earth. I first met Charlie in 2012, when he was just 19 years old.

He was just getting Turning Point USA off the ground. It has been a wild ride to witness what he built though hard work, determination, and just a strong belief that it could be done. Most of the world knew Charlie through speeches and social media posts. I was privileged to know him before that and to see the true kind-hearted person he remained behind the scenes, despite his meteoric rise.

The entire world lost a great man, a great leader. Given I am 16 years older than him, I could never picture a future where Charlie Kirk didn't exist. But Charlie pictured an America where people could go out in the public square and debate freely. He had the grace to allow others to share their differences of opinion with him.

I was so proud to see him go on Gavin Newsom’s and Bill Maher's podcasts earlier this year and told him so. For years I have been telling people that "Charlie Kirk is the William F. Buckley, Jr. of our times."

There was only one Buckley and there will always be only one Charlie Kirk. Very few people are aware of the amount of different workloads, people, and responsibilities Charlie managed. There are few people that are that multitalented. And there are few people who can rise to such heights and still be so well grounded. Many have heard me tell them: “Charlie Kirk is just a good person.” Charlie often texted Bible verses to close friends, especially friends in the movement he built, to remind them of their first duty: to God.

It is now our duty to follow in those footsteps, even if in our own quiet way. Dedicate your life to Jesus and be willing to give your life so that others might live. When I saw the close up video of Charlie being murdered, it brought me into immediate tears and it is an image I hope no one else has to see and not one that I will probably ever get out of my mind. But perhaps this was done so publicly for a reason.

It is a callous reminder of the true sacrifice it takes so that your friends might live. Charlie was fearless.

It is right to feel anger today. It is human to feel disheveled and disheartened. But Charlie Kirk was an optimist and a believer in Christ. He would not want hate to consume your heart. He probably had more “enemies” than any of us ever will, yet Charlie never allowed hate to enter his heart.

He would want you to dedicate your life to Jesus. Evil is real. We saw it on full display today.

Just four days before his own death, Charlie tweeted: "Jesus defeated death so you can live."

We lost Charlie Kirk here on earth -- but today he certainly hears the words from our Father: “Well done, my good and faithful servant.”

May we prepare ourselves to hear the same. It all starts in our own hearts.

I will never forget my friend Charlie Kirk and the great example he set for me and for our country.

Let us continue his good work.

***

A Few Photo Memories

I will have more memories about Charlie to share when the time is right, but here’s a little photo collage from over the years with brief descriptions.

We will miss you Charlie. Thanks for the gift you brought us.

This journey isn’t just about where we’re going. It’s about who we become along the way. Cultivating an adventurous heart is one of the most essential traits for any entrepreneur, creator, or dreamer. On this trip, you’ll push your boundaries, connect deeply with like-minded travelers, and gain fresh perspectives for the year ahead.

And because Fearless Journeys has spent years building deep relationships with local innovators across Chile, Argentina, and even in remote corners of Patagonia, you’ll experience these destinations in a way few travelers ever do — guided by insiders who know the land, the culture, the people — and us.

✨ Three Ways to Join the Journey

You choose your path — join us for one segment, several, or the full adventure:

Part 1: Santiago & Valparaíso, Chile

Dec 28 – Jan 2

We begin in vibrant Santiago, where modern city life meets breathtaking mountain views. From there, we’ll head to the colorful coastal city of Valparaíso to ring in the New Year in spectacular style.

You’ll witness one of the largest New Year’s Eve fireworks displays in all of South America — a dazzling show over the Pacific Ocean you’ll never forget. Along the way, we’ll enjoy a scenic vineyard stop, soak up Chile’s art and culture, and explore the nearby Casablanca wine region or coastal trails for optional adventures.

Part 2: Mendoza, Argentina

Jan 2 – Jan 6

From Santiago, we take a short flight to Mendoza, Argentina’s celebrated wine country, where we’ll stay on a breathtaking private ranch surrounded by the Andes.

This is a fully all-inclusive experience designed to immerse you in Mendoza’s natural beauty and rich traditions:

• Horseback riding through vineyard country, winding in and out of the ranch where we’ll be staying — all in the shadows of the Andes.

• Sailing along the serene waters near Potrerillos Dam, with panoramic mountain views.

• Tasting world-class wines at two exclusive vineyards in the Uco Valley.

• A 4x4 off-road adventure through the historic ranch of the Palma family, which has been in their hands for over 200 years.

• Evenings by the fire with traditional Argentine asados and live folklore shows under the stars.

This is where luxury meets authenticity — a rare chance to connect with the land, the culture, the people, and each other.

Part 3: Patagonia Expedition

Jan 6 – Jan 11

Our final chapter takes us deep into Patagonia — one of the most awe-inspiring regions on Earth. And we’re doing it the right way: January is peak summer in Argentina, the perfect time to explore this remote paradise when the weather is at its best.

This segment includes:

• Standing face-to-face with the majestic Perito Moreno Glacier — with an option to add on a glacier trek!

• A day trip to Mount Fitz Roy in El Chaltén, considered one of the most beautiful treks on the planet.

• A scenic road trip into Torres del Paine National Park in Chile — world-renowned for its dramatic landscapes and wildlife.

• An otherworldly exploration of the Petrified Forest, often compared to South Dakota’s Badlands, but with one incredible twist: you’ll see dinosaur bones scattered across the terrain!

Thanks to our relationships with local innovators who call this region home, you’ll gain unique insights into Patagonia’s history, culture, and future — an experience you won’t find on any standard itinerary.

Optional Add-On: Buenos Aires

Jan 12 onward

For those who want to extend the journey, you can join me in my favorite city in the world — Buenos Aires. Immerse yourself in Argentina’s vibrant capital: tango, world-class dining, leafy plazas, and the rich culture of Palermo, Recoleta, and San Telmo. It’s the perfect way to savor one more chapter of this South American adventure.

🔗 How to Join Us

Fearless Journeys 2.0 members get exclusive access to this trip.
If you’d like to be part of this once-in-a-lifetime experience, the first step is to apply to join Fearless Journeys 2.0:

👉 Apply Here

Spots are limited, and with the start of a new year, this is shaping up to be one of our most popular adventures yet.

🌟 Why This Trip Matters

At Fearless Journeys, we believe travel is one of the best investments you can make in yourself. It changes how you see the world — and your place in it. When you challenge yourself, whether it’s hiking Patagonia, sailing near the Andes, or watching fireworks over the Pacific, you open doors to new ideas, connections, and possibilities. And we’re sure to have many great conversations around fire pits and along our trail hikes.

This isn’t just a trip. It’s a chance to reset, recharge, and reimagine what’s possible for your life and business in 2026 — alongside a community of curious, driven, and fearless fellow travelers.