Today's track: Killers — The Red Clay Strays

My listening has always been eclectic. I'll obsess over one artist for weeks, then pivot to something completely different just to see what happens. When Spotify and Apple Music came out, it felt like someone handed me access to the entire archive of human emotion. Before that, it was mix CDs. Burning tracks. Sequencing moods. Trying to make the transitions feel right.

In college, I was a breakfast server at the Hilton at the Green in Lexington — it's not a Hilton anymore — but back then I'd clock in at 5 a.m. It felt aggressive at the time. But it paid well, you met interesting people, and honestly, it taught me something I didn't know I was learning.

One morning, I had the privilege of serving Aretha Franklin. And I knew how amazing that was. Even then, I understood I was in the presence of something extraordinary. I also once served the Blue Man Group — less blue in person than you'd think.

That same season of life — same early mornings, same late nights — the college bar-band scene was buzzing. Sundy Best was one of my bands. Tyler Childers. Just raw, local talent tearing it up in small rooms before the rest of the world caught up.

There I was, refilling coffee for the Queen of Soul at sunrise... watching the Blue Man Group eat eggs like normal humans... and then listening to Sundy Best and future stars play college bars at night.

Life felt stitched together by music.

A few years ago, I read Dave Grohl's The Storyteller. If you don't know who Dave Grohl is — he was the drummer for Nirvana and the frontman of the Foo Fighters. In the book, Dave wrote about the early touring days. Sleeping in his car. Crashing on stages with beer spilled all over them. Just uncomfortable, broke, exhausted — the way every band starts out.

Then one night, they were in California, and someone put them up in their beach house. Gave them a scooter. Gave them some great weed. And in the book, Dave just talked about how nice it was to have that. That break. That moment where someone saw them grinding and said, "Hey — let me take care of you for a minute."

And I remember reading that and thinking: Man, if the opportunity ever comes, I'd like to be able to do that too.

There's a place locally called Zanzibar, and they're usually up on bands much earlier than everyone else. I've gotten to speak to Julien Baker for five minutes. I've gotten to talk to Maggie Rogers. A lot of people who really blew up — and I caught them at Zanzibar before anyone else did.

So one night, I didn't have any shows coming up — which of course, I had Bourbon & Beyond that weekend, I just kind of forgot about it — and I was scrolling through Zanzibar's calendar. I saw The Red Clay Strays.

I listened. And I was like — oh wow, these people are pretty good.

Then I had one of those ideas that starts small and gets bigger in about thirty seconds. First it was: Wouldn't it be cool to get a group together to go? Then it was: You know what would be funny? Let me invite the entire Louisville subreddit.

So I did.

About sixteen of us showed up. It was the RCS first show outside of Alabama.

And here's the thing I'll never forget — the band asked to take a picture with me and my girlfriend. Not the other way around. Because nobody had ever made shirts for them before. We showed up in Red Clay Strays shirts, and they couldn't believe it.

I gave them my business card. I asked them where they were staying.

The next three times The Red Clay Strays rolled through Louisville, they stayed at my Airbnb.

And I thought about Dave Grohl sleeping in his car. I thought about that beach house in California. I thought about what it meant to someone grinding on the road to just have a moment of real hospitality.

So I gave them great local craft beer. Bourbon — because you can't come through Kentucky and not. Please and Thank You cookies — the top-ranked cookie in Louisville, and if you haven't had one, fix that immediately. Local weed. And a few books.

I eventually gifted Drew Nix — the lead songwriter — a signed Wendell Berry book. If you don't know Wendell Berry, he's one of Kentucky's greatest writers. Poet, novelist, farmer, philosopher. The kind of person who writes sentences that rearrange something inside you.

Berry once wrote: "It may be that when we no longer know what to do, we have come to our real work." He said poetry isn't a career but a vocation — a calling. He wrote "Do not be ashamed to say what you feel, even if you are one of the few who feel it."

If you've ever listened to The Red Clay Strays — really listened — you can hear that philosophy in their music. The honesty. The calling. The refusal to be ashamed of what they feel. Berry also wrote, "Practice resurrection." And that's exactly what these guys did — five guys from Alabama who kept showing up, kept believing, kept playing small rooms until the world caught on.

I gave Drew that book hoping maybe I could inspire someone who inspires me. And wouldn't it be something if he read Berry's words and heard echoes of his own music in them? That's how neat and intimate life can be. The inspiration just keeps circling back.

One Christmas, the band sent me a hand-drawn picture that they'd all signed. Just showed up. No ask attached. No reason other than they're genuinely good dudes. That's who they are.

If you don't know The Red Clay Strays yet, you're about to. Five guys from Mobile, Alabama who formed as the successor to a Gulf Coast cover band in 2016. They spent five years building a grassroots following the old-fashioned way — relentless touring, small rooms, earning every single fan one show at a time. They crowdfunded $50,000 to record their debut album. No label money. No shortcuts. Just belief.

Then "Wondering Why" took off and they blew up — and the rest of the world finally caught up to what the people in those small rooms already knew.

They won Best New Duo/Group at the Academy of Country Music Awards. Then they won Vocal Group of the Year at the CMA Awards — ending Old Dominion's seven-year streak. Brandon Coleman and the guys dedicated that award to a late band member, and if you watched that moment, you felt it.

They've been on Joe Rogan. They just released "Live at the Ryman." New music is coming this summer. And in August 2026, The Red Clay Strays will headline Madison Square Garden.

Madison Square Garden.

A band that stayed at my Airbnb in Louisville is headlining the most famous arena on the planet.

And would you believe it — a few short years after that first show at Zanzibar, they were one of the headliners at Bourbon & Beyond. Right here in Louisville. The same weekend I'd actually forgotten about because I was too busy scrolling for new music. Life has a sense of humor like that.

When I look back, it feels like I've had front-row seats to moments that later became history.

Serving Aretha Franklin breakfast and knowing exactly how amazing that was. Watching Tyler Childers play college bars before he sold out arenas. Buying a house from the bass player of Steppenwolf — yes, the "Born to Be Wild" band. Hosting The Red Clay Strays before CMA trophies and MSG.

And almost all of it traces back to one thing: hospitality.

Real estate didn't just put me in rooms. It taught me how to host.

Serving breakfast at 5 a.m. was hospitality. Buying Airbnbs was hospitality. Building short-term rental portfolios in places like Red River Gorge is hospitality at scale.

Reading Dave Grohl's book and thinking "I want to be the guy with the beach house" — that was the instinct. Short-term rental investing is what gave me the ability to actually do it.

That mindset is what turned a college kid pouring coffee into someone who builds real estate businesses. The instinct is the same — take care of people, pay attention to the details, and create an experience worth remembering.

It’s why I answer every single reply to this newsletter. It’s why I still get excited helping my clients find the financial freedom they’re looking for — speeding up retirement, helping a significant other stay home with the family, getting time freedom back. That’s what gets me hyped.

I started this by saying I've always loved mixing business and pleasure. I want to come back to that, because I think most people have it backwards.

We're taught to keep things separate. Work is work. Play is play. Don't blur the lines. Stay in your lane.

I think that's terrible advice.

Getting into short-term rental investing opened a door I never expected. It let me be the guy with the beach house. It let me hand a band from Alabama some bourbon, some Please and Thank You cookies, and a signed Wendell Berry book — and hope that maybe I could give back a fraction of what music has given me.

That didn't happen because I kept business and pleasure in separate boxes. It happened because I let them bleed into each other.

I couldn't be more thrilled for those guys. They're genuinely great dudes — kind, humble, the real deal. They were big-time the moment I heard them. And I expect them to be making music and killing it for a long, long time.

Here's what I'd leave you with today.

You don't have to keep everything separate and delineated. The things that light you up and the things that pay you — they don't have to live in different rooms. In fact, the most interesting things in my life have happened in the overlap. Serving Aretha Franklin. Hosting The Red Clay Strays. Building a business I actually love showing up for every day.

There is magic happening all around us. All the time. You just have to tune in and be a part of it. Life rewards action — not perfection, not waiting for the right moment, not overthinking it. Just jumping in.

I didn’t have a plan when I invited the entire Louisville subreddit to a show. I just thought it would be fun. And that one impulse led to friendships, stories, and a front-row seat to watching five guys from Alabama go from my Airbnb to Madison Square Garden.

So jump in. Follow the instinct. Mix business and pleasure. Let the things you care about inform the work you do. Make your life more interesting and more fulfilling — on purpose.

You might be surprised where it takes you.

Hit reply and tell me — what’s your version of this? When did jumping in lead to something you never expected?

Warmly,
Rob Bergeron

Owner–Realtor at Award-Winning Winner Realty
OffMarket.deals | Property Partner Data Company

PS: My mowing playlist from the weekend, enjoy! Mow Time

PSS: If you're new here — welcome. This is The Morning Bergeron. I write about Louisville real estate, investing, and occasionally the moments that remind me why I do this. If someone forwarded this to you, subscribe here so you don't miss the next one. And if you're ready to invest in Louisville, I've got 11 deals live right now. Let's go get one.