Country singer Lainey Wilson has revealed that she was so financially strained early in her career that she had to rely on her sister for money, even as her music was beginning to gain radio play.
She described the period in a clip from her Netflix documentary "Keepin' Country Cool," where she reflects on meeting her now-fiancé, Devlin "Duck" Hodges.
"I was broke. I was so broke when we met," she said. "And he thought I was doing a little bit better than I was. But a few weeks after we met, my sister had to Venmo me a couple hundred bucks."
At the time, Wilson had already released "Things a Man Oughta Know" to radio in August 2020.
However, the song's commercial success was delayed, taking several months to gain traction with radio and streaming audiences, according to Taste of Country.
The track eventually reached No. 1 on Billboard's Country Airplay chart in September 2021, though artists typically wait months longer to receive royalties.
Her comments reflect the financial uncertainty she faced on her rise to fame. The documentary describes this period as "her struggles and triumphs at a pivotal career moment."
In the clip, Wilson also discussed her love of songwriting.
"I knew whenever I had written my first song that I loved how it made me feel when I was in the middle of writing the song," she said. "When I was coming up with the idea, feeling like, 'Man, I created something from nothing. How cool is that?'"
She added, "And I knew that that feeling was so special that I couldn't completely let it go, and I think that's why I knew it was my calling."
Her relationship with Hodges developed during that time.
The couple began dating in 2021 after meeting through mutual friends and later became engaged in February 2025.
Wilson had described their first date at a bar called Silverado's, noting its affordability.
"It had free beer and wine from 5 to 10 p.m.," she told People. "I was like, 'This boy likes to ball on a budget, too. This is gonna work out!'"
Wilson said that wedding planning is ongoing but not rushed.
Speaking with People at the premiere of "Reminders of Him," she said, "Girl, I need some help. I need some help," before adding, "It's going good. Honestly, we're taking our time, and I've told him, and he's on the same page."
She said that they just want the wedding to be "about what it's supposed to be about and just enjoy it."
Zoe Papadakis ✉
Zoe Papadakis is a Newsmax writer based in South Africa with two decades of experience specializing in media and entertainment. She has been in the news industry as a reporter, writer and editor for newspapers, magazine and websites.
© 2026 Newsmax. All rights reserved.