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- 2 weeks ago31 min
Ep. 190 - The importance of offline community
Timestamps 2:25 - I'm suspended from X 3:53 - You don't own any of your social media relationships 6:20 - You need to have offline community 9:24 - The post that might have gotten me suspended 11:29 - Can I build an offline town square? 17:20 - I propose a political truce 23:33 - My theory on why black people are obsessed with relationship topics Listen and subscribe wherever you get your podcasts. Want to contact the host? Send an e-mail to cruelphilosophr@gmail.com
- Apr 9, 202631 min
Ep. 189 - The Resistance Can't Resist
I hate this war. This war is stupid. Why are we at war with Iran. Also...there is no resistance. We're cooked. Want to contact the host? Send an e-mail to cruelphilosophr@gmail.com Follow me on X @cruelphilosophr
- Mar 31, 202616 min
Ep. 188 - The Workplace Crush
Some episodes are about the state of the world. This one is about the state of the back office. Today I get honest about what a work crush actually does for you, where the line is between harmless and not, and what the post-MeToo moment quietly took from office culture. Plus: eighth grade reinvention and a closing song. Timestamps 1:17 — The difficulty of the solo show 2:22 — The work crush and what it does for you 4:18 — Eighth grade, style changes, and becoming serviceable at sports 9:34 — Is having a work crush cheating? 14:15 — "The Workplace Crush" (closing song) Listen and subscribe wherever you get your podcasts. Want to contact the host? Send an e-mail to cruelphilosophr@gmail.com
- Mar 18, 202633 min
Ep. 187 - As an American, Who Do I Want to Win This War?
Trump is running the tables — Venezuela, Iran, now Cuba. In this episode, I get honest about an uncomfortable question: as an American, do I actually want us to win this war? TIMESTAMPS 1:09 — Welcome back + why timestamps matter now 3:59 — The Iran-America-Israel war — and why everyone is lying 4:59 — Do I want America to win? An honest answer 16:49 — Cuba: "I think I can do anything I want with it" 20:11 — From liberal to libertarian and back again 29:08 — The takeaway every Black and Brown nation should hear Want to contact the host? cruelphilosophr@gmail.com
- Mar 7, 202620 min
Ep. 186 - The War Nobody Voted For
America is bombing Iran — and less than 30% of the country wanted it. So who does this war actually serve? In this episode, I break down the real forces behind the conflict: Netanyahu's decades-long push for regime change, the Greater Israel project, and the Christian Zionist apocalyptic theology embedded inside Trump's cabinet. Add a Congress that just voted to surrender its own war powers, and you have a country drifting toward catastrophe with nobody at the wheel who was actually put there by the people. This is what happens when religious fundamentalism gets a seat at the table. Subscribe on Apple Podcasts and Spotify. Leave a rating and review — it keeps the show going. Contact: cruelphilosophr@gmail.com
- Feb 17, 202625 min
Episode 185: Worst Boyfriend Ever Read in NYC. I Was There.
Worst Boyfriend Ever — one of Substack's most controversial and compelling writers — did a live reading in NYC, and I was there. I took the 2 train down to 14th Street on a Saturday night, something I haven't done solo in maybe a decade, and walked into a packed bar that was definitely not built for 120 people. WBE read offensive material while people walked out mid-reading in protest. He threw books at audience members. He didn't flinch once. What I left with wasn't just a recap of a wild night — it was clarity about the crowd I want to be around and what fearlessness actually looks like in practice. Timestamps: 1:40 – Intro and call for ratings/reviews 3:06 – How I discovered Worst Boyfriend Ever on Substack 4:28 – Arriving at the bar, navigating to the reading space 8:27 – WBE takes the stage and reads chapter one 10:20 – People start walking out mid-reading; WBE starts throwing books 13:14 – Danny Lee reads (the best reader of the night) 13:57 – The Indian girl reads from her phone 16:19 – The Amsterdam dude reads and works the crowd 17:49 – The Louis CK lookalike laughs at his own jokes 19:43 – WBE returns: "Why I Like Asian Girls" and "Why You Shouldn't Love Women" 20:52 – Closing thoughts on finding your crowd and overcoming fear Links: Worst Boyfriend Ever on Substack: jamesguilty.substack.com Contact: cruelphilosophr@gmail.com Enjoyed the episode? Please leave a 5-star rating and review on Apple Podcasts and Spotify — it really helps the show grow.
- Feb 13, 202610 min
The Fringe That Founded America
Episode #184 Only about a third of colonists supported the American Revolution—another third stayed loyal to Britain, and the rest remained neutral. If a motivated minority could overthrow an empire and reshape history, what does that mean for today? This episode challenges the assumption that because most Americans aren't extremists, we're safe from extremism taking hold. Majority comfort might be the wrong measure of democratic safety.
- Feb 6, 20268 min
It's not illegal for cops to lie to you
To all of you who are engaging in illegal activity, asking someone "are you a cop" is not how you avoid getting arrested. Have you ever been arrested after a cop told you he wasn't a cop? cruelphilosophr@gmail.com
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About The Cruel Philosophr
Welcome to "The Cruel Philosophr," the safe place for unsafe conversation. Dive into provocative discussions where no topic is too controversial and no opinion is off-limits. This podcast is your go-to for raw, unfiltered perspectives that challenge the status quo. New episodes are released whenever inspiration strikes, bringing you the most pressing and polarizing topics of our time.
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