Blocks w/ Neal Brennan Jon Lovett
Oct 16, 2025
Jon Lovett, former White House speechwriter and co-founder of Crooked Media, dives deep into personal challenges and political insights. He candidly discusses his struggles with ADHD and depression while finding humor in life's absurdities. Lovett shares his journey from a long-term relationship to dating again, revealing fears of loneliness and his complex relationship with the gay community. He also explores the current political climate, emphasizing the need for trust in leadership and the impact of social media on activism.
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Surprise Party Tree Moment
- Neal describes hiding behind a tree at Jon's surprise birthday and failing the stealth bit spectacularly.
- Jon recounts watching Neal freeze then jump, and remembers it as a delightfully failed hiding attempt.
Running Media Means Choosing Your Battles
- Jon says Crooked Media grew by focusing on hosting strengths and outsourcing management tasks.
- He highlights the tension of personal well-being amid covering dire national news.
Turning Forty Triggered A Reset
- Jon recounts hitting a depressive period fueled by unmanaged ADHD and nightly edibles during the pandemic.
- He credits therapy and cutting back on edibles for starting his recovery around age 40.
