Celebrating Yourself Instead of Shaming Yourself - Looks Like Work, Season 1, Ep 22
What if big life changes weren’t something to hide—but something to celebrate?
In this deeply personal and practical conversation, Chedva Ludmir sits down with Olivia Howell, CEO and co-founder of Fresh Starts Registry and March Lion Media, to talk about building a business rooted in empathy, emotional honesty, and mission-driven strategy.
Olivia shares how her own divorce, paired with her social media background and a natural instinct for connection, sparked the creation of Fresh Starts—a platform designed to support people navigating life’s toughest transitions. From job changes to heartbreak, Olivia believes those moments deserve community, rituals, and confidence—not shame.
This episode covers everything from the vulnerability of pitching VCs to the everyday work of staying grounded while growing something big. It’s a candid look at rewriting what it means to be a founder, embracing Yenta energy, and building systems that reflect your deepest values.
What We Talk About:
The origin story of Fresh Starts Registry—from journal entry to public platform
How Olivia used her own transition to build support for others
Serving both people navigating change and the experts who help them
Why confidence starts with small, physical decisions
Building a business with your sister (and a shared brain dump Slack channel)
Moving from service business to tech startup
Taking Fresh Starts from bootstrap to pre-seed funding
Staying values-driven: no user tracking, no vanity metrics
How a course for moms emerged from real-world conversations
Building rituals, tools, and language that normalize hard changes
Olivia’s Powerful Question:
What kind of life do you want to live—and who do you need in your corner to live it?
A grounding prompt for anyone navigating a big shift.Key Lessons:
Big changes deserve visibility, not shame
Confidence during transitions starts with small, embodied decisions
Support structures should work for both users and service providers
A values-first business model can shape everything—from privacy policies to pricing
Sisterhood, whether literal or metaphorical, can power sustainable growth
It’s never too late to seek investment on your own terms
“When you change the stuff around you, the stuff around you changes.”
Listen to this episode on Spotify | Apple | Wherever you get your podcasts
Resources & Mentions:
Visit the Fresh Starts Registry website
Olivia & Chedva's recent faves: Somebody Feed Phil, Only Murders in the Building, Summer Breakdown by Colleen Temple
For more information on the course Olivia is launching, follow her & Chedva on Instagram @thedigitalyenta & @chedvakl
Catch up on previous seasons of Looks Like Work wherever you get your podcasts: Spotify | Apple | Podbean
Subscribe to the newsletter: chedva.substack.com
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