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

In this episode of First Round’s On Me, Joey and Hannah pull back the curtain on why FROME evolved from a dating app into a social app — and what problem it’s actually trying to solve.They unpack the tension between technology and genuine human connection, the confusion users have felt around too many features, and why the simplest explanation is often the most powerful. From explaining the app in a single sentence to breaking down how drink credits, partner venues, and real-life meetups actually work, this episode is both a philosophy lesson and a practical reset.The conversation expands into Gen Z’s rejection of screen addiction, the growing “analog” movement, and why even the people who built social media won’t let their kids use it. At its core, this episode is about getting people off their phones and back in front of each other — using technology as a bridge, not a replacement, for real connection.If you’ve ever felt overwhelmed by group chats, endless scrolling, or plans that never actually happen, this episode explains why FROME exists — and why real connection still matters.💬 In the comments: Do you feel the shift toward more “analog” experiences happening already?00:00 – Technology vs genuine human connection 01:00 – Why FROME evolved from dating app to social app03:00 – The problem: too many features, unclear core message05:00 – Explaining FROME in one simple sentence06:30 – Turning group chats into real plans08:00 – Incentivizing real-life connection10:00 – Social media’s shift from “we” to “me”12:00 – The return to analog experiences14:00 – Gen Z, screen addiction & social media bans16:00 – Why tech founders don’t let their kids use screens18:00 – How FROME actually works (plans, credits, venues)21:00 – Why plans must involve other people23:00 – Capturing moments vs curating perfection25:00 – Why FROME isn’t Instagram or a dating app27:00 – Community feedback & simplifying the experience29:00 – Final thoughts: get off your phone, meet people29:40 – Outro & gratitude