

EP 20: Why Men Are Afraid to Say “I Don’t Know” ft. Dr. Dakotah Tyler
What if the smartest thing you could say is, “I don’t know”? In this episode of Learned the Hard Way, Kier Gaines sits down with astrophysicist and former Division I football player Dr. Dakotah Tyler (Dr. Star Kid)for a conversation about curiosity, masculinity, identity, and what happens when the…

EP 19: You Can't Fix People You Love
Sometimes the people we love are carrying more than we can see. A new baby. A growing career. Depression. Anxiety. Burnout. The pressure of leadership. The weight of trying to hold a family together. When someone you love is struggling, your first instinct is usually to fix it but what if that's n…

EP 18: Money Won't Make You Feel Safe ft Tiffany Aliche (The Budgetnista)
Money isn't just something we earn, spend, or save. It's something we feel. For a lot of us especially men money quietly becomes the measure of our safety, our confidence, and sometimes even our identity. A healthy bank account can make us feel secure. An unexpected expense can make us question ou…

EP 17: Don't Trade Peace for Pleasure ft. KevOnStage
Everybody talks about cheating like it's a morality issue.This conversation asks a different question: What are you actually risking... and what are you really chasing? In this episode of (L)Earned The Hard Way, Kier Gaines sits down with comedian, entrepreneur, and husband KevOnStage for one of t…

EP 16: The Performance Tax: The Price Black People Pay to Succeed (Ft. Savon & Antoinette from the Can’t Afford Therapy Podcast)
Some rooms don't just ask you to show up.They ask you to perform. To soften your voice. To shrink your personality. To make yourself "easier" to digest. To become a version of yourself that feels acceptable even if it doesn't feel authentic. For Black professionals, that performance often becomes…

EP 15: You Can Be a Good Person... and Still Be a Bad Partner
Being a good person doesn't automatically make you a good partner. In this episode of (L)Earned The Hard Way, Kier Gaines unpacks one of the biggest misconceptions about relationships: character and relationship skills are not the same thing. You can be kind, loyal, funny, and deeply loved by the …

EP 14: Imposter Syndrome Is Lying to You Ft. Jess Hilarious
How do you know the voice in your head is lying to you? In this episode, Kier Gaines sits down with comedian, media personality, Jess Hilarious, for an honest conversation about imposter syndrome, self-doubt, and what it really means to earn your place in the room. What starts as a conversation a…

EP 13: Are You Leading... or Just Controlling?
Are leaders born... or do they become one decision at a time? In this solo episode of Learned The Hard Way, Kier Gaines challenges one of the most common beliefs about leadership: that it's something you're entitled to instead of something you earn. From relationships and parenthood to business a…

EP 12: How Much Should You Care? Ft. Crissle West
What happens when being the person everyone depends on becomes the thing that's breaking you? In this episode, Kier Gaines sits down with media personality, cultural critic, and podcast host Crissle for a conversation about empathy, emotional labor, boundaries, and the hidden weight of being the p…

EP 11: The Truth About Feeling Unheard in Your Relationship
Why do so many relationship problems feel impossible to solve… even when both people care? In this special mailbag episode of Learned The Hard Way, Kier Gaines answers real voice notes from listeners navigating some of the hardest questions relationships can throw at us. From feeling emotionally …