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

In this episode of First Round’s On Me, we’re joined by Kalissa Persaud — actor, model, and creator — for a wide-ranging conversation about art, identity, confidence, and what it really means to build a creative career in the age of algorithms.

We talk about acting vs. content creation, why follower count is quietly reshaping opportunity, and how micro-influencers are becoming more trusted than celebrities. Kalissa opens up about rejection, craft, modeling for major fashion houses, and the pressure of growing up in industries that reward perfection while punishing humanity.

The conversation expands into AI in the arts, the danger of over-curation, confidence vs. self-belief, and why real connection — eye contact, presence, imperfection — is slowly disappearing in a hyper-digital world. At its core, this episode is a reminder that art is supposed to be human, not optimized.

Funny, thoughtful, and unexpectedly philosophical, this is a conversation about choosing belief in yourself when the world is constantly telling you who to be.

💬 In the comments: Do you think social media is helping or hurting creativity right now?

00:00 – Kalissa Persaud joins the show & modern acting

02:00 – Actors vs influencers: how opportunity is changing

05:00 – Self-love, confidence & identity

08:00 – Modeling, acting & finding your craft

11:00 – Rejection culture in creative industries

14:00 – Content creation vs trained performance

17:00 – Consistency over talent

20:00 – Belief in yourself & confidence erosion

23:00 – Social media as a double-edged sword

26:00 – Eye contact, presence & lost social skills

29:00 – Technology vs human connection

32:00 – AI in the arts: threat or tool?

35:00 – Why imperfection is essential to art

38:00 – Fashion as self-expression

41:00 – Discovering who you are beyond work

44:00 – Modeling, major brands & naïveté

47:00 – Final thoughts