Why Networking Feels Gross (and What Actually Works) with Maya Rupert episode artwork

EPISODE · Sep 15, 2026 · 34 MIN

Why Networking Feels Gross (and What Actually Works) with Maya Rupert

from Flip the Box® with Shari Leid · host Shari Leid

In this episode, Maya and Shari explore what happens when we stop treating connection like networking and start building relationships rooted in trust. They talk about connecting across political and cultural differences, why common ground can open conversations that debate cannot, and how listening to experiences different from our own can reveal what we simply don’t know we don’t know.They also dig into authenticity: what it really means to be yourself, why that can be more complicated for some people than others, and why authentic leadership starts with being willing to examine our own assumptions.At the heart of the conversation is a simple idea: we don’t have to agree with someone to get curious about them.Because you can’t hear someone’s story while you’re busy writing it for them.KEY TAKEAWAYSAuthenticity begins when you're not concerned about who you need to be.Connections deepen when we choose to listen to understand, not to respond.Building genuine relationships can be the key to unlocking career opportunities.GUEST BIOMaya Rupert is an author, political strategist, and social justice leader who has spent her career navigating the intersection of identity, power, politics, and belonging. She served as campaign manager for Julián Castro’s presidential campaign, senior advisor to Elizabeth Warren’s campaign, and campaign manager for Maya Wiley’s run for mayor of New York City. She is also the host of the NAACP Image Award-nominated podcast When We Win and author of The Real Ones: How to Disrupt the Hidden Ways Racism Makes Us Less Authentic.Flip the Box® with Shari Leid is for leaders and entrepreneurs who've built something impressive — and still feel disconnected underneath it all. Each week, TEDx speaker, 4x author, and connection coach Shari Leid helps you connect to yourself, your career, and your community using the Flip the Box® framework,  a four-step method for building real connection in any room, in sixty seconds or less.CONNECT WITH SHARIConnect with ShariWebsite: https://sharileid.comBook tour, February 2027: https://sharileid.com/book-tourYouTube: https://www.youtube.com/sharileidInstagram: https://www.instagram.com/an_imperfectly_perfect_life/Work with Shari: https://sharileid.comMedia inquiries: Kourtney Jason, [email protected] engagements: AAE Speakers Bureau, or email [email protected] the free Connection Audit App, a practical tool for evaluating and strengthening the quality of your personal and professional relationships.Music by Viacheslav Starostin from Pixabay

Episode metadata supplied by the publisher feed · Published Sep 15, 2026

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Why Networking Feels Gross (and What Actually Works) with Maya Rupert

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