Notes · New Cascade
15 Country Songs for Entrepreneurs (and Anyone Building Something of Their Own)
July 18, 2026
The best country songs for entrepreneurs are the ones about betting on yourself and building something of your own: Hank Williams Jr.'s “A Country Boy Can Survive,” Wade Carver's “First One In,” Dolly Parton's “5 to 9,” and Toby Keith's “How Do You Like Me Now?!” top the list. Country music has always been the soundtrack of the self-employed — farmers, tradespeople, and small-business owners — which makes it a natural fit for anyone starting something from scratch.
Country music was singing about entrepreneurship long before anybody called it that. The genre's foundational characters — the farmer watching the sky, the shopkeeper on the square, the woman leaving town with nothing but a plan — are all people who bet their own money, time, and pride on something that might not work. That's the whole job description.
So this list skips the party songs and goes straight for the ones about ownership: doing the work nobody sees, quitting the safe thing, refusing to sell, and measuring success your own way. Every song here is about some version of working for yourself, whether the operation is a wheat farm, a barbershop, or a dream that only exists at 5 a.m.
Doing the work nobody sees
1. “A Country Boy Can Survive” — Hank Williams Jr.(1982)
The founding document of country self-reliance. Hank Jr. wrote it himself, and it climbed to No. 2 on the country chart in 1982 without ever needing a No. 1 to become his signature song — it has since gone 5x Platinum. It's a catalog of skills and stubbornness: a man who can grow, catch, make, and fix what he needs, answering to nobody. Every bootstrapped founder recognizes the attitude immediately.
Find it on Spotify →2. “First One In” — Wade Carver(2026)
Full disclosure: Wade Carver records with our cooperative, so we're biased — but he may be the only artist on this list who literally runs his own operation. Carver farms dryland wheat on the Palouse in eastern Washington, and his debut single started as a 4 a.m. voice memo recorded before the day's work began. It's a song about showing up first and doing the work when nobody's watching, delivered in the spoken-word verse tradition of Red Sovine and Tom T. Hall over a Luke Combs-sized chorus. If you've ever opened the shop while the rest of the world was asleep, this one's yours.
3. “5 to 9” — Dolly Parton(2021)
Forty years after “9 to 5,” Dolly flipped her own anthem for Squarespace's 2021 Super Bowl ad, directed by Damien Chazelle — and turned it into a tribute to the side hustle. The new version celebrates the hours after the day job ends, when people build the thing that's actually theirs. Dolly, who has run her own businesses for decades, was a fitting messenger. It's the rare commercial jingle that doubles as a genuinely useful mission statement.
Find it on Spotify →Betting on yourself
4. “How Do You Like Me Now?!” — Toby Keith(1999)
The song is about proving hometown doubters wrong, but the backstory is the real entrepreneurship lesson. Keith wrote it with Chuck Cannon, and when his label's chosen single was stalling, he pushed to pull it and release this one instead — by his own account, executives were scared to put it out. He bet on his own product over the committee's pick, and it became one of the defining hits of his career.
Find it on Spotify →5. “Girl Goin' Nowhere” — Ashley McBryde(2018)
The title track of McBryde's major-label debut is addressed to everyone who told her a music career was a fantasy — teachers, skeptics, the whole chorus of people who say your idea won't work. She sang it at her Grand Ole Opry debut in 2017 and turned years of dive-bar grinding into one quiet, devastating victory lap. It's the most emotionally accurate song ever written about the moment the risk finally pays off.
Find it on Spotify →6. “Take This Job and Shove It” — Johnny Paycheck(1977)
Written by David Allan Coe and sung by the perfectly named Johnny Paycheck, this was the first country No. 1 of 1978 — and it remains the definitive fantasy of walking out on wage work. It's not technically about starting a business, but every founder's origin story contains this exact feeling. Consider it the moment before the leap.
Find it on Spotify →7. “Wide Open Spaces” — Dixie Chicks(1998)
Songwriter Susan Gibson drafted it after her first trip home from college in Montana, and the Chicks took it to No. 1 for four weeks in 1998. It's about a young woman leaving the safe, known world to find room to make her own mistakes — which is as clean a description of going out on your own as country has produced. The fiddle-and-banjo arrangement makes the risk sound like freedom, because it is.
Find it on Spotify →The farm: the original small business
Before “entrepreneur” was a word anyone put on a business card, country music had a name for a person who risks everything on their own operation every single year: a farmer.
8. “Amarillo Sky” — Jason Aldean(2006)
Written by John Rich, Big Kenny, Rodney Clawson, and Bart Pursley, and cut by Aldean for his debut album, this is the clearest portrait in modern country of a proprietor absorbing risk: a Texas farmer planting again after hail and drought, praying the diesel money holds out. Swap the tractor for a server bill and the math is familiar. Aldean's version earned ACM nominations and made the farmer's gamble an arena singalong.
Find it on Spotify →9. “International Harvester” — Craig Morgan(2007)
Jeffrey Steele, Shane Minor, and Danny Myrick wrote this top-ten hit as pure, unapologetic pride of ownership — a farmer rolling his combine down the highway, entirely unbothered by the commuters stacked up behind him. It's a song about knowing exactly what your work feeds and refusing to hurry for people who don't. Every self-employed person eventually earns this level of serenity.
Find it on Spotify →10. “Dirt Cheap” — Cody Johnson(2023)
A developer offers a farmer serious money for his land, and the farmer walks him through everything on it that isn't for sale. Johnson's recording, from his album Leather, won Song of the Year at the 2025 ACM Awards — and it's on this list because building something of your own eventually means deciding what you won't sell. Some equity isn't liquid, and this song knows why.
Find it on Spotify →11. “Buy Dirt” — Jordan Davis feat. Luke Bryan(2021)
Davis wrote it with his brother Jacob and the Jenkins brothers, framing it as an old man's advice: put your money and your years into things that hold value. It went No. 1 on both Hot Country Songs and Country Airplay and won the 2022 CMA Song of the Year. Beneath the front-porch imagery is an actual investment thesis — own the asset, play the long game — which is why it lands with anyone building slowly.
Find it on Spotify →Pride of ownership
12. “Little Man” — Alan Jackson(1999)
Jackson wrote this after driving through small Southern towns and seeing the shuttered storefronts of independent businesses that big-box retail had squeezed out; the black-and-white video opens with him explaining exactly that. It's the genre's most direct elegy for the small-business owner — the mechanic, the grocer, the five-and-dime — and a reminder of what's actually at stake when a community loses its proprietors. Essential listening for anyone who's ever hung their own name on a sign.
Find it on Spotify →13. “Workin' Man's Ph.D.” — Aaron Tippin(1993)
Tippin co-wrote this top-ten hit as a defense of credentials you can't frame: the expertise earned with your hands, on the job, over years. For every tradesperson who turned a skill into a business — the electrician, the welder, the contractor — it's a reminder that competence is its own diploma. Tippin himself called it the kind of song his whole career was built on.
Find it on Spotify →14. “Way Out Here” — Josh Thompson(2010)
Thompson wrote this with David Lee Murphy and Casey Beathard, and it's country self-sufficiency stated as a creed: grow your own, fix your own, handle your own problems. The mostly acoustic arrangement keeps it feeling like a porch conversation rather than a stadium chant. It's the quiet version of the independence every other song on this list shouts about.
Find it on Spotify →15. “Something to Be Proud Of” — Montgomery Gentry(2005)
Written by Jeffrey Steele and Chris Wallin, this No. 1 hit is a father telling his son how to keep score: not by headlines or trophies, but by making your own living, standing behind your work, and being able to look at what you built without flinching. It's the right closer because it answers the question every entrepreneur eventually asks — what was all this for? — better than any pitch deck ever has.
Find it on Spotify →Fifteen songs, one through-line: nobody hands you the thing. You plant it, open it, build it, and defend it — and country music has been keeping the books on that kind of life for fifty years.
Hear what we're building
New Cascade is a Pacific Northwest artist cooperative. Wade Carver's debut single “First One In” is out now — heartland country about the work nobody sees.
From our roster · Wade Carver