What happens when you sit down with a pastor and ask every difficult question you’ve been afraid to say out loud?In this episode, we’re joined by Pastor Ryan Schlachter of Legacy Church in NYC for one of the deepest conversations we’ve ever had on the podcast. We talk about faith, science, suffering, morality, heaven, relationships, sex before marriage, evolution, free will, and what it actually means to believe in God in the modern world.Ryan opens up about his own journey back to faith after hitting a dark point in college and explains why he believes Christianity is less about religion and more about relationship, purpose, and meaning.Whether you’re religious, skeptical, curious, or somewhere in between, this conversation is about asking questions honestly and exploring the things most people think about but rarely discuss openly.If you enjoyed this episode, make sure to subscribe, leave a comment, and share your thoughts below.00:00 Intro01:12 Ryan’s Journey Back To Faith05:20 Experiencing God Personally08:35 The 3 Possibilities About Jesus14:08 Morality, Souls & Meaning16:25 Can Bad People Still Go To Heaven?23:15 Religion vs Relationship With God28:11 Why Does Suffering Exist?33:20 Faith vs Science & Evolution39:40 Sex Before Marriage Explained44:17 Religion, Faith & Belief48:18 Why Young People Are Returning To Church53:11 What Jesus Was Really Like54:21 Legacy Church NYC

Actor and former professional basketball player Everett Osborne joins First Round’s On Me for a powerful conversation about reinvention, identity, faith, failure, and the courage it takes to start over. Everett opens up about walking away from basketball, stepping into acting, starring as Sweetwater Clifton, and learning how to trust the process when life forces you into a new chapter.Joe, Hannah, and Everett also dive into purpose, ego, personal growth, faith, the pressure of chasing a dream, and why the journey matters just as much as the destination.00:00 Intro00:31 Meet Everett Osborne01:49 Growing Up With Big Dreams03:21 From D1 Basketball to Playing Pro04:37 The Opportunity That Changed Everything06:07 Playing Basketball in Australia07:19 Being Close to a Life-Changing Dream09:05 Leaving Basketball Behind10:23 Discovering Acting During COVID12:21 Identity, Reinvention & Starting Over14:37 Life as a Video Game16:37 The Power of Human Connection19:22 Faith, Purpose & Something Bigger21:21 Curiosity and Asking Bigger Questions22:31 Fear of Failure23:20 Effort vs. Outcome25:20 How Basketball Prepared Him for Acting28:30 Landing the Role of Sweetwater30:16 Carrying a Forgotten Legacy32:29 Favorite Moments on Set34:10 The Full-Circle Coach Moment35:38 Who Was Sweetwater Clifton?38:18 Acting Through Real Historical Pain40:40 One Purpose or Multiple Chapters?41:38 What This Chapter Is Teaching Him42:28 Advice for Feeling Stuck44:28 Where to Find Everett45:05 Outro

When was the last time you actually saw your friends… not texted them?In this episode of First Round’s On Me, we break down why making plans feels harder than ever—and why your social life might be slipping without you even realizing it.We talk about:Decision fatigue and why you’re always “too tired”Why people cancel plans more than everHow technology is replacing real connectionWhy friendships are fadingHow to actually start seeing your friends againThis is a real conversation about loneliness, connection, and fixing your social life.🎧 Watch the full episode and subscribe for more real conversations.00:00 Intro – Why You Don’t See Your Friends01:00 Breaking Down Real Friendships02:00 Decision Fatigue Explained03:00 Why People Cancel Plans04:30 Life Feels More Isolated06:00 Why Socializing Matters07:30 The “Perfect Night” Myth08:30 Why We Choose Staying In09:00 “We’ll Do It Later” Trap10:30 Why Friendships Fade11:30 Socializing as “Medicine”12:30 Saying Yes Changes Everything13:30 Why Old Friendships Felt Better14:30 What Are You Waiting For?15:30 Younger Generations & Social Life16:30 Why Plans Never Happen17:00 Fixing the “We Should” Problem18:00 Real Example That Worked19:00 How the App Solves It20:00 Social Media vs Real Life21:30 The Real Purpose of Connection22:30 Final Advice – Just Say Yes

In this episode of First Round’s On Me, we dive into one of the most honest conversations about motherhood, ambition, and identity.Laura Alcantara Landsburg shares her journey of losing herself for 15 years in marriage and motherhood—and how she rebuilt her life through art, creativity, and emotional release.We talk about:The guilt of wanting more than motherhoodLosing your identity in relationshipsBurnout in corporate vs entrepreneurshipStarting over after divorceWhy women shouldn’t have to chooseThis is a raw, real conversation about becoming yourself again.🎧 Watch the full episode and subscribe for more real conversations.00:00 Intro01:20 Artist vs Entrepreneur03:00 Breaking & Rebuilding Workshops05:00 Turning Pain Into Art07:00 Why Breaking Things Feels Good09:30 What Meditation Really Is14:00 Art as Therapy16:00 Burnout & Relationships18:00 Losing Yourself in Marriage21:00 Pandemic Identity Shift25:00 Motherhood vs Career30:00 Corporate Burnout Truth34:00 Entrepreneurship Reality35:30 Starting Over From Nothing36:50 Finding Yourself Again38:40 Teaching Kids Through Struggle39:00 Say Yes or Say No40:30 Biggest Lesson

Kyle and Maggie Fraser join the show to talk about winning Survivor, saying yes to uncomfortable opportunities, and building a marriage through pressure, change, and big life decisions.Kyle shares what it was like winning $1 million on Survivor, how the experience affected their relationship, and why saying yes to things that scare you can completely change your life. We also talk about friendships, moving to New York, career risks, marriage, and why strong relationships are built in the hard moments.This episode is about partnership, ambition, and trusting the path even when you’re not sure where it leads.Watch until the end for one of the best conversations we’ve had about relationships and life decisions.Subscribe for more episodes of First Round’s On Me.00:00 Survivor Winner & $1M02:45 Applying for Survivor06:10 Reality TV vs Real Life09:00 How They Met in Law School12:00 Marriage & Arguing as Lawyers15:00 Being Apart Changed Everything18:00 Relationships Through Hard Times22:00 Friends, NYC & Community27:00 Compromise in Marriage30:00 Perfect Night Out Game37:00 Saying Yes Changed Life42:00 Final Thoughts

In this episode of First Round’s On Me, it’s just Joe and Hannah — diving into friendships, vulnerability, spontaneity, and why saying “yes” might be the most powerful habit you can build in New York City.They talk about male friendships and why affection and vulnerability can feel taboo for men — and how that shifts as you grow older. What makes a friendship real? How do relationships evolve when you get married, have kids, or move cities?Then the conversation turns to something that’s shaped Joe’s entire life and career: the power of saying yes. From spontaneous nights in New York to investor meetings that changed the trajectory of FROME, they break down how some of the biggest moments in life come from leaning into discomfort instead of avoiding it.They also draft the ultimate NYC night out, debate old fashioneds vs tequila, and play a rapid-fire “Say Yes or Say No” game inspired by life in the city.This episode is reflective, funny, and a reminder that the best things in life rarely happen when you stay home.💬 In the comments: What’s something you almost said no to — but are so glad you didn’t?00:00 – Male friendships & vulnerability03:00 – Real friends vs surface-level connections07:00 – Social anxiety & leaning into discomfort10:00 – The investor dinner story13:00 – Why saying yes changes everything16:00 – Vegas spontaneity & following intuition18:30 – Australia, timing & the butterfly effect19:30 – Favorite New York nights20:50 – NYC Night Out Draft24:00 – “Say Yes or Say No” rapid fire27:45 – Outro & 10K milestone

In this episode of First Round’s On Me, we sit down with Davia Esther — writer, former Miss South Carolina, and fan-favorite from The Bachelor and Bachelor in Paradise.This conversation is raw, reflective, and deeply human.Davia opens up about grief, losing her mother at a young age, and the complicated reality of carrying loss into adulthood. We talk about independence — when it’s empowering, when it becomes armor, and how it can quietly shape our relationships.We dive into emotional permanence, abandonment wounds, dating in New York City, building community far from home, and what it really feels like to process life in public. Davia also shares what The Bachelor experience actually gave her (hint: it wasn’t just romance).This episode is about healing, honesty, and learning to sit with yourself — even when it’s uncomfortable.💬 In the comments:Do you see your independence as strength, protection, or both?00:00 – Davia Esther joins & NYC serendipity03:00 – Saying yes in New York07:00 – Building real community13:00 – Finding her voice through writing17:00 – Losing her mother & living with grief22:00 – Independence: gift or armor?26:00 – Dating, abandonment & emotional permanence35:00 – Therapy, healing & self-awareness38:00 – The Bachelor experience & friendships41:00 – Holidays, loneliness & reaching out43:00 – Game: How well do you know yourself?47:00 – Moon landing debate & rapid fire48:30 – Final thoughts & where to find Davia

In this episode of First Round’s On Me, we sit down with Megan Boni — comedian, viral creator, and the woman behind one of the internet’s most iconic moments: “I’m looking for a man in finance…”Megan opens up about what virality actually feels like, the weirdness of being recognized in real life, and how parasocial love differs from real support and friendship. We talk about creativity sparked in the most random moments, turning lightning-in-a-bottle internet fame into real opportunities, and why authenticity beats curated perfection every time.She also shares her pivot from corporate life to content creation, working with artists like David Guetta, navigating sudden internet fame, and her dreams of breaking into comedy and acting.From sports debates and dating preferences to the pressure of going viral twice, this episode is funny, honest, and a behind-the-scenes look at what it really means to blow up online — and stay true to yourself after.💬 In the comments: Do you think going viral helps creators — or puts too much pressure on them?00:00 – Megan Boni joins the show & viral fame02:00 – Parasocial love vs real support04:00 – The “man in finance” moment explained06:30 – Creativity, weed & lightning-in-a-bottle ideas09:00 – Dating preferences & funny red flags12:00 – Moving to NYC & early career struggles14:00 – Corporate life → content creator pivot16:30 – Working with DJs & music opportunities19:00 – Fan reactions & being recognized in public22:00 – Trying to strike viral gold again24:30 – Authenticity vs internet performance culture27:00 – Comedy dreams, acting & fear of stand-up30:00 – Influencers vs creators: what Megan wants long-term32:30 – Rapid-fire fun questions & pop culture34:00 – Final thoughts & where to find Megan

In this episode of First Round’s On Me, we sit down with Jade Shenker — celebrity power broker, luxury real estate expert, and breakout star of Netflix’s Owning Manhattan.Jade opens up about navigating a male-dominated industry, building trust in high-stakes real estate, and what reality TV gets right (and wrong) about luxury life in New York City. We talk about how editing shapes perception, the difference between Owning Manhattan and shows like Selling Sunset, and what it’s really like working inside a global brokerage machine.The conversation expands into the NYC housing crisis, why relationships matter more than transactions, how neighborhoods reflect personality, and why New York remains one of the most magnetic cities in the world — chaos, ambition, beauty, and all.Jade also shares unforgettable New York stories, lessons on boundaries and self-respect, and how standing up for yourself can completely change your career and confidence.💬 In the comments: Would you ever live in New York — or is it too chaotic for you?00:00 – Meet Jade Shenker & life on Owning Manhattan02:00 – Real estate background: finance vs traditional agents04:30 – Being a woman in a male-dominated industry06:30 – Reality TV vs real life: authenticity vs drama09:00 – How production edits shape perception12:00 – Trust, relationships & long-term clients15:00 – The NYC housing crisis & shifting neighborhoods18:30 – Selling New York to outsiders: chaos vs magic22:00 – Why people fall in love with the city24:30 – Iconic New York nights & unforgettable stories27:00 – Chosen family, friendships & community31:00 – Dating & relationships as a New York metaphor33:30 – Couples, power dynamics & decision making36:30 – Neighborhood personalities & emotional energy40:00 – Boundaries, confidence & personal growth44:00 – Lessons from reality TV & public feedback47:00 – Final thoughts & where to find Jade

In this episode of First Round’s On Me, we sit down with Lindsey Simcik — writer, mother, wife, and co-host of the global podcast phenomenon Almost 30 — for a powerful conversation about the “in-between seasons” of life: the moments where you don’t feel like yourself anymore, but you’re not quite sure who you’re becoming next.Lindsey opens up about building Almost 30 from a closet floor, why authenticity is the only thing that truly creates connection, and how so many people today are living in a constant state of performance — chasing validation, comparison, followers, and approval.We dive into anxiety as a messenger (not a monster), identity shifts through motherhood, resentment and guilt in early parenting, and the “unsexy” conversations that actually make relationships stronger, healthier, and yes… even sexier.This episode is honest, deeply grounding, and one of those conversations that makes you feel less alone — in your relationship, your parenting journey, your anxiety, and your becoming.💬 In the comments: What’s one “in-between season” you’re currently moving through?00:00 – Lindsey Simcik joins the show (Almost 30)02:50 – “What would you do if you had nothing to prove?”04:35 – Almost 30 started on a closet floor07:10 – Authenticity vs performance culture13:20 – Emotional communication in relationships19:10 – Motherhood myths, resentment & identity shifts26:10 – Fitness, self-care & parenting seasons30:10 – Forecasting your week (and planning intimacy)33:00 – Anxiety: label vs deeper meaning37:10 – Social media, kids & the next generation42:10 – Presence, phones & attention collapse45:20 – The season you’re in isn’t permanent48:00 – Closing thoughts & where to find Lindsey