After being sentenced to federal prison, Amanda and Legend wrote over 300 letters to each other — letters that would eventually become the foundation of their nonprofit, 300 Letters. In this powerful episode, they join Roselyn to share their journey from incarceration to inspiration.

We talk about:

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  Growing up in survival mode

  
  


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  What it really means to be labeled a “felon”

  
  


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  How incarceration impacts entire families — not just individuals

  
  


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  Rebuilding after prison, raising emotionally-aware sons, and founding a nonprofit that’s rewriting the system

  
  

This episode is raw, honest, and full of the kind of healing our community needs to hear.

🎧 Listen now and support Amanda and Legend’s work at 300letters.org.

🎭 Attend their Masquerade of Miracles Gala on June 5th in Miami → Get tickets here

📲 Follow them on Instagram: @300letters

⏱️ Timestamps:

00:00 – Spanish Word of the Week: Embarazada

04:00 – Meet Amanda & Legend

08:00 – Growing up in survival mode

12:30 – From college student to indictment

17:00 – Why incarceration is a family issue

26:00 – Finding out she was pregnant in prison

31:00 – The truth about medical care while incarcerated

39:00 – The cost of prison on families

45:00 – Reentry and healing through 300 Letters

52:00 – Redefining “felon” and changing the narrative

1:07:00 – Raising emotionally-aware kids

1:13:00 – Starting a nonprofit as returning citizens

1:19:00 – Real success story from a 300 Letters family

1:22:00 – Gala info + final thoughts

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