Strategy, Power and Knowing Your Worth with Vanessa Santos

What Jessica's Drinking 🍾

Casa Martinez Wine, Bonitas 2023 Chenin Blanc. A Latiné-owned family brand out of the Napa-Sonoma area, where Daniel Martinez not only runs his own label but stewards vines for other brands. A perfect sip for a conversation this rich.

What happens when the woman who has helped others build empires finally lets her own walls come down?

In this deeply honest episode of Wine & Chisme, Jessica sits down with her amiga and one of her favorite humans on the planet , Vanessa Santos, entrepreneur, board-level strategist, Forbes Most Impactful Woman of Latin America honoree, and the woman behind Letters from the InBetween.

Vanessa grew up as the eldest daughter of immigrants in Washington Heights and the Bronx - navigating survival, community, corporate rooms she wasn't supposed to be in, and a love for storytelling she didn't even realize she had until she got there. She worked her way from retail to the C-suite without an Ivy League degree, scaled ventures to multi-millions in revenue, became a millionaire before 30... and then watched it all come apart.

In this episode, she shares what it really looked like: a divorce, a business exit, losing her home, and sitting with 7-8 months of Airbnbs and friends' couches. And why she's more herself now than she's ever been.

This one is for every woman who has ever performed strength while quietly drowning, and who is ready to hear that the shedding season was always preparing you for what's next.

"Everything is happening for me, not to me. This is just a chapter of my book."

In This Episode, We Talk About:

• Growing up first-gen in New York City and what the hood actually teaches you
• How Vanessa bluffed and asked her way from retail floors to C-suites
• The real cost of performing success — big wedding, reckless spending, and an abandonment wound dressed up as generosity
• Going from millionaire to unhoused — and what that stripped away (and revealed)
• High-functioning depression, PTSD, and what it means to finally receive help
• Colorism in Latinidad and a grandmother's lesson about using privilege as a door you hold open
• Why lack of expression equals depression
• What self-reclamation actually looks like when you're in the middle of it
• Letters from the InBetween, The Table, and Glow Up Hour — what Vanessa is building now
• Her message for any woman stuck in the research phase: it's time to push

Guest Resources & Links

• Newsletter (Letters from the InBetween): vsantos.co/newsletter
• Glow Up Hour (free monthly community)
• Instagram: @vanessasantosleon