Is Money Freedom Or A Trap? Trust, Love & Getting Rich W/ Dave Pechillo If This Doesn’t Work… podcast

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Is Money Freedom or a Trap? Trust, Love & Getting Rich w/ Dave Pechillo

1d ago 1:41:00

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Justin sits down with his longtime friend Dave Pechillo, a finance-minded, crypto-curious realist — to talk about money, freedom, relationships, AI, and why billionaires eventually get bored of everything.

They unpack what real financial freedom looks like, why most people don’t actually want infinite money, and how chasing status turns normal dudes into psychos. From Elon Musk and Trump to cartels, fentanyl, and the CIA, the conversation blends dark humor with sharp insight on how power, addiction, and AI are reshaping modern life.

On the personal side, Justin and Dave get into trust vs love, codependency, why love is “disgusting,” and the real work of becoming self-aware. They share stories of addiction, recovery, and being “invisible” in public when you’re at your lowest, and how humility and growth hit harder than money ever will.

Later they spiral into the future of AI and crypto, universal basic income, and why this is the worst AI will ever be again. It’s a raw, funny, and philosophical conversation about what it means to stay human while everything around you goes digital.

In this episode:
• Money vs freedom — how much is “enough”?
• Billionaires, cartels & why power corrupts
• Trust vs love and the fight to stay connected
• Addiction, recovery, and self-awareness
• AI, Bitcoin, stablecoins & the coming UBI future

🎙 Podcast: If This Doesn’t Work…
👤 Guest: Dave Pechillo

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201 episodes

#Comedy #Justin Anderson #Boys As They Talk