06/18/2026
Blake Brewer lost his father unexpectedly. What his mother found in a briefcase hours later became the foundation for one of the most meaningful gifts a parent can leave behind.
In this conversation, Keith and Doug host Blake Brewer, founder of Legacy Letter, who has helped more than 20,000 people write meaningful, lasting letters to the people they love most. Blake walks through the complete Legacy Letter framework: how to open with honesty, how to apologize in a way that actually lands, how to tell your children you love them with the specificity that changes lives, and why advice only sticks when it follows affirmation. He also shares the stories he's collected from parents across the country, including a daughter who called her mom on Christmas night to say it was the best day of her life because of a letter.
Key Topics:
• Why Blake's father wrote a letter no one knew existed, and what it contained that made grief bearable
• The five common mistakes people make when apologizing in writing — and the one that derails the whole letter
• How to answer the question your child will ask for the rest of their life but stop asking out loud
• Why pride in character matters more than pride in achievement — and how to make that distinction in writing
• The Apple stock analogy: why starting this letter sooner compounds its value over a lifetime
If you've been meaning to write something down for the people you love, this one is the nudge worth hearing.
Apple Podcast: https://podcasts.apple.com/us/podcast/up-your-average/id1768337684?i=1000773243937
YouTube: https://www.youtube.com/watch?v=_oWNOH9SIgI
Blake Brewer lost his father unexpectedly. What his mother found in...