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.
Publisher
Chessa Eskandanian-Yee & Clare Kingsland Roediger
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. :)
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Come hangout on socials! Follow Chessa: https://www.instagram.com/chessayeeFollow Clare: https://www.instagram.com/ckroedigerTikTok: https://tiktok.com/@clareandchessa
19 Feb 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. 💛
31 Jan 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 (https://www.youtube.com/@clareandchessa)
Our TikTok (https://www.tiktok.com/@clareandchessa)
Find Chessa on socials:
Instagram (https://www.instagram.com/chessayee)
LinkedIn (https://www.linkedin.com/in/chessayee)
Find Clare on socials:
Instagram (https://www.instagram.com/ckroediger)
LinkedIn (https://www.linkedin.com/in/clareroediger)
For any business inquiries: clare@advisorey.com
Reach and audience
Public platform figures. Ratings count people who left a rating, not total listeners.
YouTube views
1,356
Score snapshot 15 Sept 2025
Apple Podcasts (US)
5.0 / 5
2 ratings
Podcast Authority Score: 23 / 100
A composite of feed quality, social presence, YouTube performance and engagement. Read the methodology.
Quality
8
Social presence
0
YouTube
65
Engagement
32
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Guest appearances
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