
Episode #319
Jacob Hackworth: What Took You So Long, Songwriting Success & Betting on Yourself
On Episode 319 of Outside The Round , Matt Burrill sits down with longtime Raised Rowdy homie Jacob Hackworth to talk about the wild ride from Missouri railroad worker and Nashville barback to hit songwriter and rising country artist. Hackworth reflects on coming up through the same writers-round scene as Raised Rowdy, building relationships around town, and eventually finding success behind the scenes before stepping back into the spotlight as an artist. The guys dive into Jacob's debut EP, What Took You So Long , a seven-song project that follows the week after a breakup from getting your heart crushed to finally getting back in the game. They also talk about “I Wanna Quit,” the massive country-radio response to the project's title track, touring with longtime friend Tucker Wetmore, upcoming shows with Zach John King, and getting ready to play Red Rocks. Jacob also looks back on his songwriting career, from major cuts and No. 1s to Morgan Wallen recording “Jack and Jill,” and explains the challenge of balancing writing songs for other artists with building his own catalog. It's a full-circle conversation with one of the original Raised Rowdy guys who's been putting in the work for years — and is now getting his chance to show everyone what he can do as an artist. Follow on Social Media: Jacob Hackworth: @jacobhackworth Matt Burrill: @raisedrowdymatt Outside The Round: @outsidetheround Raised Rowdy: @raisedrowdy Chapters (00:00:00) - Intro and recent festival stories (00:00:44) - Country Rising festival in Winnipeg and Missouri river show (00:02:37) - Jacob's rise as a songwriter turned artist (00:04:22) - Crafting the breakup concept EP (00:09:05) - The new single and record-breaking radio add day (00:11:40) - Celebrating the ad day at Duck Blind and bar backing roots (00:13:39) - Grinding to make it in Nashville (00:15:27) - Balancing radio promo, touring with Tucker Wetmore, and home life (00:18:01) - Country music as family and touring culture (00:19:24) - Upcoming tour with Zach John King and new venues (00:21:06) - Venue stories and tour markets (00:23:22) - Cabo festival and bachelor party plans (00:24:53) - Key West Songwriters Festival memories (00:26:43) - Pawpaw's hats and Bro Country Night events (00:27:14) - FGL legacy and bro country nostalgia (00:29:22) - Writer class and award show camaraderie (00:34:41) - Meeting Brothers Osborne and big cuts (00:35:45) - Writing Jack and Jill for Morgan Wallen (00:38:06) - Balancing writing for himself vs other artists (00:39:59) - Building his team with Sam and Goat Island (00:42:44) - The team behind him and momentum building (00:45:10) - Touring all over the country and favorite stops (00:47:19) - Festival culture, tailgating, and fan connection (00:50:19) - Wildest fan interactions and meet and greets (00:52:23) - The concerts that inspired him (00:54:01) - Venue deep dive - Texas Club, Stage AE, Milwaukee history (00:58:32) - Hopes for the project and advice to his younger self (01:00:14) - Closing thoughts and where to find Jacob's music

