In this episode of Clover, I sit down with the brilliant and wildly accomplished Tina Sharkey for a conversation that honestly feels like three masterclasses in one: community-building, career design, and the future of human connection in an AI-driven world.

Tina walks me through her very non-linear career path—from hanging out in her mom’s New York fashion office as a teen, to an unexpected pivot into tech and investing, to co-founding iVillage, bringing Sesame Street online, scaling BabyCenter globally at Johnson & Johnson, and launching community-first CPG brand Brandless. Through it all, she shares how she’s always brought the same “toolkit” with her: storytelling, community, curiosity, and a deep belief in creating products and experiences with people, not just for them.

We also dig into her current work at USC, where she’s teaching and backing Gen Z founders, experimenting with GenAI in the classroom, and thinking deeply about what makes us “divinely human” in a world of powerful machines. Tina is both optimistic and clear-eyed: AI can unlock a new kind of renaissance—but only if we protect literacy, critical thinking, and real human connection. And for women in leadership, she shares some tough-love truths about putting your hand up before you feel “ready,” finding hidden doors, and making your career a relay race—not a solo sprint.

Conversation highlights:

• From fashion floors to technology boardrooms
  How growing up with a single, career-focused mom in New York’s fashion world gave Tina early exposure to women in leadership—and how one moment in an investor’s office completely rerouted her from fashion into tech, media, and investing.
• Inventing “social media” before it had a name
  Tina shares the early days of iVillage, why chat rooms and message boards were so revolutionary, and how she coined the term social media to explain this new kind of community-driven content to advertisers and partners.
• Building iconic brands through community
  We walk through her roles bringing Sesame Street onto the internet, scaling BabyCenter into a global platform (including the birth clubs so many of us relied on), and designing Brandless as a community-led, access-first CPG brand.
• Serendipity, hidden doors, and saying yes
  Tina talks about the role of serendipity—from chance meetings in offices and delis to unexpected board roles—and how being open, curious, and willing to ask respectful questions has shaped every major career inflection point.
• Humanity as our moat around the machines
  Tina shares her framework for thinking about AI: why she uses it as a collaborator, not a replacement, and why our empathy, soul, and lived experience are the “moat” that machines can’t cross.
• Gen Z, consciousness, and going “punk” on attention
  From her vantage point teaching at USC, she talks about how Gen Z is already pushing back on screen addiction, what excites her about their creativity, and why reclaiming our own consciousness is non-negotiable in an AI world.
• Literacy, equity, and the stakes of this moment
  Tina opens up about the crisis of literacy in the U.S., how reading levels are tied to incarceration rates, and why democratizing access to education and healthcare is a core part of her mission.
• Real talk for women in leadership
  We close with tactical guidance: stop waiting until you’ve “done the job” to go for it, bring your authentic self everywhere you go, surround yourself with people who are brilliant at what they do, and remember that careers are built in teams and relay races—not through hero moments.

Connect with Tina on LinkedIn (her most active platform), Instagram,