The fact that you are asking where to start already puts you ahead of most people. A lot of people feel the impulse to help and never follow through. You are following through, and that matters.
What inmates need most is hope. Not pity, not lectures, not reminders of how they got there. Hope. The belief that something better is possible and that someone on the outside sees them as more than their worst moment. That is what consistent contact from a caring person actually provides, and it is more valuable than most people realize.
Start with a letter. Introduce yourself, explain that you heard about their situation through Ear Hustle or another source, and let them know you are reaching out because you genuinely want to offer support. Keep it warm and genuine without being overwhelming. A simple first letter opens the door and lets them decide how to respond.
From there, if you learn what their interests are, you can send magazines or books through InmateAid. Reading is one of the most effective tools an inmate has for making time pass productively and keeping the mind engaged. A subscription to a magazine they actually care about is a recurring reminder that someone thought of them.
Encouraging optimistic thinking and forward momentum in your letters is the other piece. Not in a preachy way, but by asking questions about what they want their life to look like after release, what skills they want to develop, what they are working toward. That kind of conversation helps someone stay focused on who they are becoming rather than stuck in where they are.
InmateAid has everything you need to get started in one place.