Mark Carr: I want to have a great understanding of warm outreach that I haven't connected with in a while. I'm looking to establish a longer relationship with a mentor that is receptive where I want to reconnect.

• Treat this as the mentor approach, and remind them about the previous interaction, the value that you got out of it, and how it's led you to where you are now.
• Shift the value paragraph to highlight how his guidance changed your actions, decisions, outreach, and trajectory over the last two years.
• Make the ask warmer and more specific by anchoring it to previous impact, then introduce a new, nuanced problem that naturally invites a deeper conversation.
• Aim for the sweet spot question that is too complex for email but perfect for a call, making it easy and exciting for him to help again.
• Keep future updates shorter and more frequent to maintain relationships warm, reinforce progress, and turn every interaction into a virtuous cycle of mentorship.

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