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Recap: Group Trip to Nashville

Written by
Francisco Gonzalez
October 31, 2022
Our October 2022 group trip connected with insiders in Music City, U.S.A.!

The first U.S. city that Fearless Journeys chose to run a group trip to was Nashville, Tennessee. This was not by coincidence. Nashville is one of the most fun and innovative cities in the United States today. It’s also one of the top places in the country that people are moving to.

Traditionally known as Music City, Nashville attracts singers, songwriters, and so many who surround every facet of that industry. But it’s no longer the only major industry that makes its home there.

One of our travelers said the biggest takeaway he learned after visiting Nashville with Fearless Journeys October 19-23, 2022, was that “Nashville has pockets of pretty much every industry – you just need to know where to look to find them.”

And that’s exactly the kind of experience that Fearless Journeys provided.

Insights to the Entrepreneurial Environment in Tennessee 

We started the official part of our trip by meeting with Justin Owen, the President & CEO of the Beacon Center of Tennessee, a public policy think tank that provides solutions for citizens and government officials. They recently formed a council on entrepreneurship and innovation, a working group (made up entirely of entrepreneurs), which is coming up with ideas on how to make Tennessee more hospitable to those looking to start businesses here. 

Justin was careful to make us aware of the difference between the entrepreneur and a big business – and how corporate interests are often different from what is needed for new entrepreneurial ventures to enter the market.

He and his wife Kara (who also joined us for dinner at Urban Grub in the 12 South district) are native Tennesseans and they gave us some great perspectives on the many changes the Volunteer State has seen during their lifetime, and the great promise the future holds for those here.


Amazing Historic Home for Our Group

After dinner, the group returned back to our group home. We rented a massive Airbnb, a Victorian-era home known as The Waverly (built in 1887) that has been on the historic register here since the 1960s. It has been used in music videos, photo shoots for magazines like Rolling Stone, commercials, and television shows. While back at our group home on a brisk Wednesday night (temperatures plummeted into the 30s overnight), we lit a bonfire in our backyard fire pit, got to know each other better, and prepared for a few more exciting days ahead. Each traveler had their own full bedroom and bathroom, a huge kitchen and common living spaces, as well as a big backyard with a nice covered patio. This was ideal during the fall weather that only got nicer as the week progressed. 



Southern Breakfast & Music Row

On Thursday morning we were up early and ventured out to have breakfast at Midtown Cafe. It has been here for over 35 years and is considered one of Top 50 Southern restaurants in the United States by Food & Wine magazine. It was delicious! 

After breakfast, we walked just 10 minutes over to Music Row, where we passed by many record companies and recording studios. 

In Nashville, “it all begins with a song,” and that’s why we visited the Nashville Songwriters Association International (NSAI), an organization dedicated to protecting the property rights of songwriters, which has become especially challenging in the age of streaming music. While there, we also had a private songwriting session with songwriter Greg Wilson. 



He talked to us about his own previous career as an assistant principal and high school football coach in Kentucky and how his journey led him into the songwriting field. Greg also gave us a private performance (in a storyteller session) of some of the songs he is developing for other performers. 

We then toured a few songwriting rooms at NSAI that songwriters can use here for sessions to develop music. If you’d like to learn more about NSAI, I suggest checking out Episode 112 of the Agents of Innovation podcast, which featured their Executive Director, Bart Herbison, who has led the organization since 1997.


Country Music Hall of Fame & RCA Studio B

We took a short ride over to the Country Music Hall of Fame, where the history of American music is on full display. It is huge and contains collectibles from artists from all aspects of country music. One of my favorites was seeing one of Elvis Presley’s Cadillacs and a jacket from his wardrobe.

When you walk through the galleries, read the stories, and hear the music, you really do get a sense of how each artist and genre within country music influenced each other and evolved over time. While here, we also had the opportunity to see a ridiculously large wall of gold and platinum records that fall into the country music category (my boy Elvis had quite a few). 

You end the tour by stepping into the rotunda where you can see plaques all over the walls of the official inductees into the Country Music Hall of Fame. Elvis Presley, Willie Nelson, Dolly Parton, Jerry Lee Lewis, Ray Charles, Jimmie Rodgers, George Jones, and Loretta Lynn were among just a few that I spent time reading about. What an amazing place.



If you’re a real buff, you could easily spend a half day here. Fearless Journeys spent 90 minutes here before we caught the shuttle to the historic RCA Studio B. That tour starts at the Country Music Hall of Fame, where it must be reserved in advance, as we did for our group. 

When you come on a Fearless Journeys group trip every detail is taken care of. Just book the trip and we include everything in advance like a one-stop shop. Food, transportation, accommodations, and admissions to places like these – all included. We know you have other things in your life to attend to. Leave the planning to the planners.

Once we arrived at RCA Studio B, we realized we were in the room where it happened. 

It was in this room that Elvis Presley recorded more than 100 of his songs. It was in this room where Dolly Parton recorded many of her hits, including “Jolene.” Thousands of hits from musicians we all know were recorded in this humble little studio. 

We listened to some of the recordings of so many of these songs during our tour including “Now or Never,” as they dimmed the lights and let the voice of Elvis sing to us as he recorded them in the very place before us.



There is a marked spot here that our tour guide told us was where Elvis Presley reportedly fell to his knees in exhaustion after recording his last take of “How Great Thou Art.” Elvis poured his heart and soul into that song and recorded it over and over and over again. At the very last take he fell to his knees and almost fainted. Perhaps he gave it all to God.

What really stood out to all of us was that there was nothing fancy about the studio. It was just a room, with some interesting acoustics that they really never perfected but tried to figure out. We were left in awe of how much American culture was created here in this humble studio, including so many songs by The King. 

It’s a reminder that as we each go on our own Fearless Journeys, we don’t need fancy. We just need to take our talents and put them out there, in whatever humble abode we might find ourselves. Just take action. And if you can, find some other talented people to collaborate with too.


Dave Ramsey Solutions


Before departing from Music Row, we found a quick bite to eat at the Funny Library cafe at the Virgin Hotel. Then we took a ride 25 minutes south of Nashville to Franklin, Tennessee. That’s where we visited the headquarters of Ramsey Solutions, the company founded and led by Dave Ramsey. 



While Dave was not in town the week we visited, we were still able to sit in on a segment of his radio show, with his substitute hosts Rachel Cruze (Dave’s daughter) and Dr. John Delony. This show runs on 600 stations across the country, is livestreamed on YouTube, and available on many podcast apps.


We also met with a member of his EntreLeadership team, Nathan Janson. And, we got an amazing tour of this 1100-person company, all put together by my friend Carolyn Ohme. They even had us meet in the “Journey” conference room which they temporarily renamed (with magic marker) to “Fearless Journeys” during our visit.




While Dave Ramsey is a household name to most, his entire journey may not be quite as well known. We really enjoyed seeing how he shares his own Fearless Journey, his triumphs and failures, even his 1988 bankruptcy petition (a photo of which is hanging on the wall for all to see). If you’d like to read a more detailed account of our visit to Ramsey Solutions, check out this post in the Fearless Journeys newsletter.

Learning more about Dave's journey inspired us to keep moving forward on our own path. The Fearless Journeys community is currently reading Dave’s book, EntreLeadership and we will have one of his EntreLeadership coaches, Mike Howerton, join us on a live session on November 10. Send us an email (fearlessjourneysLLC@gmail.com) or visit the “Learn” page at FearlessJourneys.org to learn more about this opportunity. 


BBQ & Honky Tonks

We had an action-packed Thursday but it wasn’t done yet. We went back to our home for about two hours of relaxation and then ventured out to Edley’s BBQ in the nearby 12 South neighborhood (a mere 5-minute drive from our front door). While much more money was dropped on other meals, Edley’s BBQ proved to be a fan favorite. This is what people come to the South for!

We then took a 10-minute ride over to Broadway and visited some of the famous Nashville Honky Tonks including The Stage On Broadway, Dierks Bentley’s, and Tin Roof. 


We were able to experience so much amazing live music in these small bars – with even smaller stages! The honky tonks are a major reason that Nashville is perhaps the most fun city in the USA, especially for those of us traveling here! 

None of the travelers on this group trip knew each other before they arrived. They all came as single entities and they all made new friends. Seeing them sing and dance with each other, after the many great fun learning experiences we had together all day, really brought together what this community is striving to do.


Lunch with AI Innovators

Given our action-packed day on Thursday, we left Friday morning to leisure. However, some of our travelers used the time to get work done. Since we bring entrepreneurial-minded people together on these trips, we know it’s smart to give each of them some free time built-in to the trips. 

During these pockets of open time, travelers can choose to relax, sleep in, get in some exercise, do work, or find some things to do on their own. By this time, things had warmed up in Nashville nicely on Friday and the weather for the rest of the weekend was absolutely perfect. 



We came together for lunch at the Mockingbird Cafe near The Gulch area of Nashville. It features a menu created by the two in-house award-winning culinary chefs. Our lunch included an exclusive experience with Tim & Natasha Drisdelle. Tim previously worked on the Siri team at Apple; Natasha has worked as an event planner, including for Omni Hotels. Originally from Canada, they have lived in Switzerland and California and moved to Nashville about 6 years ago.

More recently, they have been developing AI software for hotel concierge services and continue to shift and adapt to find the right needs of the market and how they can scale. Their journey is still underway – including as parents; they have twin 17-year old boys and a 3-year old daughter. They both recently passed their citizenship test and will be U.S. citizens soon. None of our travelers knew very much, if anything, about Tim and Natasha. All of them came away super impressed, with most of our group citing them as the most impressive people we met in Nashville.

After lunch, one of our travelers went for a workout. The rest of us went to a coffee shop so we could each get a little bit of work done before the rest of our action-packed afternoon and evening.


Exclusive Experiences with Bitcoin Leaders

We took a 10-minute ride over to the recently revitalized Chestnut Hill neighborhood of Nashville. This is an old industrial area that is now inhabited by Nashville locations  of Apple, Spotify, and Live Nation.

We spent the middle to latter part of the afternoon here at the headquarters of BTC Inc, the parent company of Bitcoin Magazine, meeting with one of their co-founders and current CTO, Tyler Evans. This is the organization that is at the center of currency innovation for the world. They are the ones that host most of the major Bitcoin conferences in places like Miami, Amsterdam, and beyond. The most insightful conversations about the latest happening with Bitcoin is taking place in their circles. And, here we were, just sitting around the living room area of their office chatting away with Tyler for about 90 minutes.



Tyler also walked across the street with us for a local craft beer at the nearby Jackalope Brewing Company. This is another example of how this community is not just about business but also about forming personal friendships. 

As one of our travelers, Zach Newman, said after his experience with us in Nashville, “Going on a Fearless Journeys trip allows you to access people and places you wouldn’t otherwise have access to!”

After a fun time at Jackalope Brewing company (complete with playing games like cornhole), we walked back across the street to the Earnest Bar & Hideaway, which has the feel of a library inside. The check at the end of the night was even delivered inside of a classic book.

Our dinner guest here, Robert Breedlove, continued the theme of Bitcoin for the latter half of our Friday. He is the host of “The ‘What Is Money?’ Show” and talked to us about a deeper philosophy behind Bitcoin and the promise he believes it has to bring true restoration to monetary policy, provide more freedom, energize entrepreneurship, and ultimately create more innovation for humanity. Robert recently had Jordan Peterson on his podcast, interviewing him for a live audience in Miami this past spring.


After dinner, the group went back to our beautiful home, and sat around the bonfire in our backyard fire pit, while engaging in conversations about the many experiences and people we met throughout the day.


President Andrew Jackson’s Home

Saturday morning started leisurely as well, giving our travelers free time to rest, relax, or explore on their own. Our home was equipped with plenty of food for breakfast and snacks and that served us especially well three out of four mornings here.

At the end of the morning, we ventured out to The Hermitage, the home of the 7th President of the United States, Andrew Jackson. The home is about a 25-minute drive from where we were staying. During Jackson’s time, it included over 400 acres of land. Today, the estate has over 1100 acres under its care and looked absolutely gorgeous on this peak fall day. 


About 90 percent of what we saw inside the home was original to the home during Jackson’s time. Outside, we saw cotton in the fields, toured the slave quarters, and visited Jackson’s tomb, as well as the graves of many of his family members. 

One thing we appreciated is how they told Jackson’s story honestly. He was a complicated man. He pulled himself up by his bootstraps, went from poverty to elite status, led men to victory in important battles in the War of 1812 and in the Indian wars in Florida. He was a slave owner and, as President, he sent native Americans on a “Trail of Tears” out of places like Georgia westward. He fought in duels. He was a tough son of a gun. He was not a perfect man, but his Fearless Journey was made possible by grit, determination, and perseverance. This really comes through well in his story. Everyone who came to The Hermitage on our trip remarked how this visit made a big impact and was an especially great place to experience.

We went back to our home and took a couple of hours to relax. We then went out for dinner at Emmy Squared Pizza in The Gulch. It features Detroit-style pizza (deep dish but not as deep as Chicago style). Everyone loved it. We only visited this place because of a site visit Fearless Journeys did earlier this year, finding this award-winning pizzeria through discovery. We do the trial and error for you at Fearless Journeys and only take you to places we know you’re going to love.


One Last Party – Comes With a Bus! 

From there, we had a little down time. This time we kept an open mind and tried a suggestion from one of our travelers. Since we were right next to the high-end Thompson Nashville (a Hyatt hotel), she suggested we visit the rooftop bar. We did.




More than a dozen stories above Nashville, with a great view of Broadway, we had quite the view. After an hour there, we took a 10-minute ride to the headquarters of the Honky Tonk Party Express. This is the original “party bus” company in Nashville and they are probably the best to go with. They have a fleet of open air party buses, which must be reserved in advance as they are very popular (especially with the huge number of bachelorette parties in Nashville). They are BYOB, so we brought our alcohol on board with us, handing it over to the bartender who served it on demand for our two-hour experience. 

During that time, the bartender (who doubled as a DJ) also blasted any tunes we wanted to hear as we toured nearly all of the vicinity around downtown Nashville and the surrounding neighborhoods, whipping by historic venues like the Ryman Auditorium, and driving across the bridge over the Cumberland River, with glorious sites of the Nashville skyline.

Saturday night was quite the time to tour Nashville as the streets were packed with partygoers who waved and cheered as our bus went by blasting tunes. 

On this final experience in Nashville, Fearless Journeys gave “Chart Your Course” a whole new meaning. 


An Unforgettable Experience

We leave nothing on the table for those coming on a Fearless Journeys group trip. We give you the best experiences our locations have to offer while connecting you with top-of-the-line innovators and entrepreneurs, designing a trip around the collective interests of each member of our group, while helping all form friendships with each other. No one who came on our trip knew anyone else other than the organizer. They all left with deep friendships and a commitment to help each other on the rest of the journeys that lie ahead.

After coming on our trips to Guatemala and Nashville, Kevin Comer said that on Fearless Journeys group trips, “you get great stories and meet interesting people who you can work on projects with later.”

There is only one question that remains: when will you Chart Your Course with us?

We have trips coming up in Guatemala (December 2-10, 2022) and Uruguay & Argentina (March 24-April 2, 2023), with more in the works. 

Where do you want Fearless Journeys to take you? 

Journey Fearlessly, Together.

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