Drag Superstar Jaylene Tyme: Two-Spirit Pride

When your kids are little, everybody has advice. The books, the mom groups, strangers in the grocery store. And then one day they’re grown and everyone goes quiet, like the job is over. In this episode, Kortney sits down with Margaret Ruttan, Jennifer Reid, and Marylynne Stella, three women who are either right in the thick of this with her or a few steps ahead. They get into the moment the relationship shifted, what parenting an adult actually looks like compared to parenting a teenager, and the hardest skill of all: knowing when to step in and when to keep your mouth shut. They talk about boundaries around money, advice, and the people their kids choose. About apologizing to your grown children, and what happens when they remember their childhood differently than you do. About what’s been harder than anyone expected, what’s quietly gotten better, and the guilt that never fully goes away. Mostly it’s four women admitting that nobody has this figured out, well maybe Margaret does, and that the relationship doesn’t end when they grow up. It just changes shape.

Season 3 kicks off with the most requested guest in the show's history, Ryan. And he knows it. Kortney and Ryan catch up on a summer that would not quit: the car through the yard, the woman in our yard, the Airbnb incident, the Chicago trip that went sideways, Family Feud, Lennox starting her senior year, and Sully moving back out. They get into marriage, the things that got on each other's nerves, what they're proud of, and what people don't see from the outside. Then there's the trip to Bolt Farm that reconnected them and set everything that's coming next in motion. Link to the last episode with Ryan: https://youtu.be/m6_Lt-8EBlE?si=2s5f7gwrzeBFCQi4 Connect with Kortney: https://www.instagram.com/allthingskortneywilson Podcast IG: https://www.instagram.com/thekortneywilsonpodcast/ Hosted by Kortney Wilson Produced by Emma Stutts Hosted on Acast. See acast.com/privacy for more information.

In this deeply moving conversation, legendary songwriter Beth Nielsen Chapman reflects on a life shaped by music, loss, and unwavering creativity. With a career that includes writing songs for icons like Elton John, Willie Nelson, Faith Hill, and Neil Diamond, Beth shares the stories behind the music, and the personal experiences that have fueled it.

In this episode, Kortney sits down with her dear friend, Karin Thyr. This conversation dives into the nuanced realities of parenting, especially the tension between defending our choices and truly hearing our kids. It explores how well-intentioned advice can sometimes miss the mark, and why listening, presence, and flexibility often matter more than having the “right” answer. Together, they unpack how shifting parenting approaches and centering a child’s perspective can lead to stronger communication and healthier relationships.

In this episode, Kortney sits down with financial educator and author Alyssa Davies for an honest conversation about money and why we need to talk about it more openly, especially as women. Alyssa shares her personal journey with finances and breaks down the basics of investing early, managing debt, and understanding the emotional side of spending. They also dive into money and relationships, including financial transparency in dating and marriage, the importance of emergency funds, and how aligning your money with your values, including giving back, can lead to greater confidence and fulfillment.