Chats With Chessa

Chessa Eskandanian-Yee & Clare Kingsland Roediger

Chats With Chessa explores the intersection of business, partnership, and modern leadership. Lesbian life partners Clare and Chessa bring you inside their journey of building a modern recruiting firm, launching a content and media vision — and co-creating a life along the way. This is a podcast about building something intentional, human, and entirely your own.

Episodes

  1. 05/09/2025

    What It's Like Dating & Working Together

    Ever wonder how couples manage to work, date, and build a business together… without losing their minds!? We're talking about it - what works, what’s hard, and what we’ve learned from building a life and a business, side by side. It’s a vulnerable one: the messy, the money, and the magical moments that keep us aligned with our north star. :) --- Come hangout on socials! Follow Chessa: https://www.instagram.com/chessayeeFollow Clare: https://www.instagram.com/ckroedigerTikTok: https://tiktok.com/@clareandchessa

  2. 02/19/2025

    Getting Existential

    Today, we're getting deep - why are we here? What's our purpose? And can existential crises actually bring us closer to the answers? In this Ep., Chessa opens up about her (3) existential crises that shaped her journey: At 15, taking her first existentialism class and realizing there were bigger questions to ask about life, death, and purpose. Post-college, navigating loneliness and feeling disconnected from the things that once gave her meaning. In 2020, forced to sit with her thoughts - no distractions, no escapes - leading to a complete life and business transformation. We also talk about why following the beaten path isn’t always the right move, how trying to fit into a box can hold you back, and why moments of crisis can be the best thing to ever happen to you. We also yap about: The difference between passion and fulfillment (because not everything you love needs to be a career or monetized) The importance of support systems during times of uncertainty How easy it is to take everyday moments for granted These are complex, deeply personal topics, and we’re sharing from our own lived experiences—we welcome the conversation! And don’t worry, we wrap things up on a lighter note by answering some of your questions. 💛

  3. 01/31/2025

    Who We Are & Why We're Here

    Welcome to Chats with Chessa - where work and life are one! Co-hosts Clare & Chessa introduce themselves, share their backgrounds and why they started this podcast, talk a little business and the current state of work, and share this week’s tough love. Find Us on socials: Our YouTube Our TikTok Find Chessa on socials: Instagram LinkedIn Find Clare on socials: Instagram LinkedIn For any business inquiries: clare@advisorey.com

    Who We Are & Why We're Here
  • 3 Episodes

Ratings & Reviews

5
out of 5
2 Ratings

About

Chats With Chessa explores the intersection of business, partnership, and modern leadership. Lesbian life partners Clare and Chessa bring you inside their journey of building a modern recruiting firm, launching a content and media vision — and co-creating a life along the way. This is a podcast about building something intentional, human, and entirely your own.

Information

  • Creator
    Chessa Eskandanian-Yee & Clare Kingsland Roediger
  • Years Active
    2025
  • Episodes
    3
  • Rating
    Explicit
  • Copyright
    © Chessa Eskandanian-Yee & Clare Kingsland Roediger
  • Show Website
    Chats With Chessa