The Working Songwriter: Mary Chapin Carpenter

Our guest this week on the Working Songwriter hails from my neck of the woods, Washington, D.C. Mary Chapin Carpenter got her start in the proto-Americana music scene of 1970s and ’80s D.C. She broke out of that local circuit with her signing to Columbia Records; her 1992 album, Come On Come On, went quadruple platinum.

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Carpenter has toured with Emmylou Harris, Shawn Colvin, and Rosanne Cash, she’s won five GRAMMY Awards, two CMA Awards, and two Academy of Country Music Awards. Her song, “Shut Up and Kiss Me,” went to the top of the country radio charts. She has appeared on the Late Night with David Letterman and Rolling Stone calls her “one of the most grounded, sentient songwriters of her generation.” NPR has said that she’s “a singular voice in country and folk” and the New York Times praises her “intelligent, literate songwriting with emotional depth.”

Simply put, she’s an all-timer. I got a chance to catch up with her earlier this year and hear about her musical journey so far.


Photo Credit: Aaron Farrington

Basic Folk: Abraham Alexander & Kashus Culpepper

We are live at sea aboard Cayamo 2026 with Abraham Alexander and Kashus Culpepper! The pair had not met prior, but we found a couple of very cool parallels between them, so we decided to interview them together. Plus, we knew it would be more fun to have them both up on stage in front of an audience. Abraham, based in Ft. Worth, Texas, and originally from Greece, has had an impressive rise in profile thanks to opportunities from friends like Leon Bridges, Gary Clark, Jr., and Adrian Quesada (Black Pumas). Quesada actually worked with Abe on the song “Like a Bird,” which was nominated for an Oscar for its inclusion in the deeply moving 2023 film Sing Sing. Navy veteran Kashus Culpepper, born and raised in Alexander City, Alabama, grew up singing in church and learned to play guitar while deployed in Spain. His deployment actually occurred during the pandemic in 2020; left with nothing to do and nowhere to go, he spent his time learning guitar, drinking plenty of sangria, and playing for his fellow sailors (who would also be enjoying said sangria).

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Abe and Kash have a few things in common that we discuss: their emotive and boisterous singing voices, learning guitar as adults, intense histories with sports, and, of course, being very handsome. We introduce our conversation with the two musicians as “Handsome Club,” (a shout out to Lizzie No’s OnlyFans handle, @handsomelizzie) and ask them to speak about their relationship with beauty. After ensuring them that we were for real, they spoke of beauty found in the process of turning pain into something positive, and how confidence in yourself is everything. We have some poignant moments and some major laughs that are enhanced by an awesome crowd. Thanks to everyone on board Cayamo for making the first meeting of Handsome Club so successful!


Photo Credit: Joel Parks

The Other 22 Hours: Jeff Hanna (Nitty Gritty Dirt Band)

As a founding member of the legendary Nitty Gritty Dirt Band and a three-time GRAMMY winner, Jeff Hanna has navigated nearly 60 years in the music industry. His resumé includes credits with the likes of Linda Ronstadt, Emmylou Harris, Johnny Cash, and many others. In this episode of the Other 22 Hours we explore the geography of inspiration, from the 1970s Troubadour scene in LA to his 40 years anchored in Nashville’s songwriting community. Jeff reflects on the economy of a perfect line, the creative vitality of a “hard reset,” and why the bedrock of this work has to begin with the simple intention of having fun.

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In This Episode:

Jeff Hanna
Nitty Gritty Dirt Band
Matraca Berg
Ep 16 – Rodney Crowell
The Troubadour
The Station Inn
Vinyl Tap
Jackson Browne
Tim Buckley
Poco
Ep 144 – Suzy Bogguss
Ep 43 – Gretchen Peters
Stephen King, On Writing
Jerry Jeff Walker, Mr. Bojangles
The Mavericks
Ringo Starr
Levon Helm
Sheryl Crow
Fred Eltringham

Go Deeper:

Watch: View this entire conversation above or on YouTube.
Explore: Find similar conversations in these themed playlists.
Connect: Join the conversation on Instagram.

The Other 22 Hours is hosted by Aaron Shafer-Haiss (producer, mixer, musician) and Michaela Anne (songwriter, artist, creative coach). More about Aaron’s workMore about Michaela Anne’s work.


Produced by Aaron Shafer-Haiss. Original music written, performed and produced by Aaron Shafer-Haiss.

Photo Credit: Joshua Britt and Neilson Hubbard

The Working Songwriter: Charles Kelley (Lady A)

Our guest on the Working Songwriter this week hails from Augusta, Georgia, but has made his professional bones in Music City USA. Charles Kelley was one of the founding members of Lady Antebellum – now known as Lady A – and is one of the group’s principal songwriters. Their crossover hit, “Need You Now,” became one of the defining songs of the 2010s.

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Lady A have sold over 18 million albums, won 7 GRAMMY awards, and their songs have been streamed over 5 billion times. Along the way Charles has also released a pair of solo albums, including last year’s Songs for a New Moon. He’s recorded for Capitol Records Nashville and Big Machine and he’s toured with Luke Bryan, Tim McGraw, Keith Urban and many others. He’s also appeared on The Tonight Show and The Late Show with David Letterman.

Rolling Stone has said that Lady A’s “vocal harmonies helped redefine country radio in the 2010s” and Billboard calls them “one of Nashville’s most successful songwriting teams.” I got a chance to catch up with Charles a few months ago to hear about his musical journey so far.


Photo courtesy of the artist.

Basic Folk: Dawes

We are so excited to kick off our Interviews at Sea series with DAWES! We had the chance to talk to brothers Taylor and Griffin Goldsmith aboard Cayamo: A Journey Through Song in front of a packed audience during the music cruise’s 18th voyage in March 2026. The guys have been performing as Dawes since 2009, but the band has been a duo since their 2024 album, Oh Brother.

The Goldsmiths have been singing and playing together their whole lives inspired by their musician father, Lenny Goldsmith, who toured as the lead singer of Tower of Power in the 1980s. Taylor was never told it was hard to play guitar or sing, so he just did it. He always knew he wanted to be a professional musician. We talk about the ways his musical career turned out as not quite what he had expected. We also touch on how their singing has evolved over the course of their lives together.

Both Taylor and Griff are fathers, so of course we asked about the freedom that comes with priorities changing in their lives and careers – as well as what toys they may have regretted ever letting their kids have.

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One thing following Dawes around for the past year is the aftermath of the January 2025 Eaton Fire in Los Angeles. Both brothers and their parents suffered immense loss due to the flames sweeping through Altadena, California, destroying thousands of homes and causing over 30 deaths. Griffin’s son was born two weeks after the fire, a month early. Dawes became the musical face of the disaster with an emotional performance on Jimmy Kimmel Live! and opening the GRAMMYs with Randy Newman’s “I Love LA” with a veritable supergroup: Sheryl Crow, Brad Paisley, Brittany Howard, St. Vincent, and John Legend. The brothers get into what the experience taught them about healing and reaching a place where this tragedy does not define them. We hear a bit about Taylor’s love of collecting first editions and his fear of the comment section and we wrap up with a fun “Which One?” lightning round. Thanks to Dawes!


Photo Credit: Joel W. Parks

The Other 22 Hours: Derek Trucks

What happens to the creative spirit when you have been a professional “lifer” since the age of nine? Derek Trucks, widely considered one of the greatest guitarists of all time and a veteran of the Allman Brothers Band and Eric Clapton’s touring lineup, joins the Other 22 Hours to discuss longevity and leading a 12-piece musical circus. with his Tedeschi Trucks Band co-founder and wife, Susan Tedeschi. We explore the gradual shift from student to teacher, the grounding force of a musical marriage, and the essential practice of “turning the crops” to stay inspired.

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In This Episode:

Tedeschi Trucks Band
Allman Brothers Band
The Beacon Theater
Eric Clapton
Kofi Burbridge
John Lee Hooker
Koko Taylor
Ace Moreland
Colonel Bruce Hampton
Buddy Guy
Joe Walsh
Gregg Allman
Jim Scott
Tom Dowd
A Love Supreme
– Krishnamurti
Mad Dogs & Englishman (movie)

Go Deeper:

Watch: View this entire conversation above or on YouTube.
Explore: Find similar conversations in these themed playlists.
Connect: Join the conversation on Instagram.

The Other 22 Hours is hosted by Aaron Shafer-Haiss (producer, mixer, musician) and Michaela Anne (songwriter, artist, creative coach). More about Aaron’s workMore about Michaela Anne’s work.


Produced by Aaron Shafer-Haiss. Original music written, performed and produced by Aaron Shafer-Haiss.

Photo Credit: Chapman Baehler

The Other 22 Hours: Suzy Bogguss

How does an artist outlast the industry machine to build a career entirely on her own terms? We sit down with GRAMMY-winner, 1989 ACM Top New Female Vocalist, and 1992 CMA Horizon Award recipient Suzy Bogguss to explore the evolution of her 40-year career, which includes platinum records and her 2026 induction as a member of the Grand Ole Opry. Our conversation is an invitation to reconsider what we all value, moving away from the noise of major label machines and toward a philosophy of quality over quantity, independence, and deep community.

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In This Episode:

Suzy Bogguss
Matraca Berg
Jeff Hanna
Ep 43 – Gretchen Peters
Patty Loveless
Ep 46 – Mary Chapin Carpenter
Capitol Records
CAA
Kathy Mattea
Folk Alliance
Ep 16 – Rodney Crowell
Chet Atkins

Go Deeper:

Watch: View this entire conversation on YouTube.
Explore: Find similar conversations in these themed playlists.
Connect: Join the conversation on Instagram.

The Other 22 Hours is hosted by Aaron Shafer-Haiss (producer, mixer, musician) and Michaela Anne (songwriter, artist, creative coach). More about Aaron’s workMore about Michaela Anne’s work.


Produced by Aaron Shafer-Haiss. Original music written, performed and produced by Aaron Shafer-Haiss.

Photo Credit: Doug Crider

The Working Songwriter: Ricky Montgomery

Our guest this week on the Working Songwriter resides in Los Angeles, but spent many of his formative years in St. Louis, Missouri. Ricky Montgomery first built an audience on Vine in his early twenties before releasing his self-titled debut album in 2016. That bedroom pop album was a cult favorite until 2020, when several of its songs exploded on TikTok, leading to a deal with Warner Records.

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Montgomery’s singles, “Line Without a Hook” and “Mr. Loverman,” are RIAA-certified platinum and, all told, his catalog has collected more than a billion streams worldwide. That grassroots support has led to headlining tours with stops at the Wiltern in Los Angeles, Irving Plaza in New York City, and the Pageant in St. Louis, to name just a few.

This interview was recorded nearly 18 months ago and has been delayed due to a snafu on my end, but I’m so glad we get to hear it now. I think you’ll very much enjoy hearing about Ricky’s musical journey through his own words.


Photo courtesy of Prelude Press.

Basic Folk: Julian Taylor

One of the things I really enjoyed about interviewing Toronto-born singer-songwriter Julian Taylor is his relationship with the truth. He has a really peaceful attitude towards learning and sharing new information. For example, at the beginning and the end of our interview, there were biographical facts about him that I had gotten wrong in my research. Gently and matter of fact he fact-checked me and we just moved on. It was such a cool example of, “Oh, you’ve got this a bit wrong and it matters that we get it right,” but nothing about that is personal. In an era of misinformation and alternate facts, it feels really grounding to have an hour-long conversation with someone who really cares about getting it right. That shows through in his songs and in his storytelling.

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Julian experienced an eclectic musical upbringing thanks to his classical-and-gospel musician father, his mother’s love of Motown and folk, and wide influences from pop to blues. Oral tradition in his family shaped how he tells a story. Especially on his mother’s side with his Mohawk grandfather, a pastor who told incredible stories. He also discusses being pigeonholed by race and genre. Oftentimes, people will think that he performs a certain type of music because he looks a certain way. He mentions that audiences can be shocked when he pulls out a country song while sporting hair that looks more reggae than Johnny Cash. Taylor discusses his breakthrough 2020 album, The Ridge, he talks about his writing process (often starting with lyrics), and the intent behind his latest release Anthology: Volume Two – including “Hunger,” “Don’t Let ’Em” (with Jim James), “Dedication,” and “Weighing Down” – addressing mental freedom, identity politics, and self-forgiveness.


Photo Credit: Lisa MacIntosh

The Other 22 Hours: Amythyst Kiah

GRAMMY-nominated songwriter Amythyst Kiah has performed with Moby and Billy Strings and is a member of the supergroup Our Native Daughters. She joins us for a startlingly honest look at the “farce of surface-level success.” After a label debut and a whirlwind of global exposure, she found herself “barely hanging on for dear life” amidst the pressure of a rat race industry. We explore her journey to achieve detachment from outcomes, writing for sync licensing as a creative recharge, and the ancient wisdom that helped her trade the self-improvement doom loop for a slower, sustainable creative life.

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In This Episode:

Amythyst Kiah
Our Native Daughters
Brian Eno
Music for Airports
Allison Russell
Tao Te Ching
Marcus Aurelius
–  Siddhartha

Go Deeper:

Watch: View this entire conversation on YouTube.
Explore: Find similar conversations in these themed playlists.
Connect: Join the conversation on Instagram.

The Other 22 Hours is hosted by Aaron Shafer-Haiss (producer, mixer, musician) and Michaela Anne (songwriter, artist, creative coach). More about Aaron’s workMore about Michaela Anne’s work.


Produced by Aaron Shafer-Haiss. Original music written, performed and produced by Aaron Shafer-Haiss.

Photo Credit: Kevin King