Podcast Summary: Aware and Aggravated – Episode 40: "Self Trust Will NEVER Make Sense In The Moment"

Release Date: May 18, 2025
Host: Aware and Aggravated
Description: Make Leveling Up Your Natural State Of Being.

Introduction: Embracing Self-Trust Amidst Chaos

In Episode 40 of Aware and Aggravated, host Leo Skeppy delves deep into the intricate concept of self-trust, emphasizing its elusive nature when navigating tumultuous moments. Skeppy candidly shares personal experiences that highlight the challenges and revelations associated with trusting oneself, especially when situations don't align logically or emotionally.

Business Deal Breakdown: The Pitfalls of Profit Splits

Skeppy opens the episode by recounting a recent business encounter that underscored the importance of understanding deal structures. During a collaboration meeting envisioned to resemble a "Leo Skeppy version" of a product—a comprehensive and polished venture—the discussion seemed promising until payment terms surfaced.

Leo Skeppy [05:30]: "If you are ever dealing with someone in business and they say they will give you a profit split, do not take it. You never negotiate on profit splits because companies can legally even if there's a contract, they can legally get away with not paying you shit."

This revelation stems from a prior negative experience where a profit split arrangement led to financial discrepancies and unfulfilled promises. Skeppy advises listeners to avoid profit splits, likening them to tax evasion strategies companies employ to minimize payouts, thereby protecting themselves at the expense of collaborators.

Navigating Intuition: The Inner Voice of Self-Trust

Post-meeting, Skeppy experienced an inexplicable sense of irritation and rejection regarding the deal. This emotional response wasn't rooted in logical assessment but rather an inherent protective mechanism from his "soul."

Leo Skeppy [12:15]: "My soul is telling me no. It's not aggressive or mean or panic. It was just like no."

This internal dialogue led Skeppy to reflect on past experiences, particularly a flawed profit split deal from his "forgiveness collection" merch launch. Recognizing the pattern, he realized the importance of honoring his intuition to avoid repeating detrimental business mistakes.

The Cartier Earrings Desire: More Than Meets the Eye

A significant portion of the episode centers around Skeppy's intense desire for a pair of Cartier earrings priced at $11,800. This craving was not just about the luxury item but symbolized deeper emotional and psychological triggers.

Leo Skeppy [20:45]: "It's not just about the earrings, okay? It ain't about the 12 grand. I'm in a pivotal, changing moment right now."

Skeppy connects this desire to his personal journey, relating it to themes from Tina Turner's song "We Don't Need Another Hero," which resonated with his evolving sense of self and the rejection of performative heroism.

Decoding Desires: Messages Beyond Material Wants

Through introspection, Skeppy identifies that his escalating desires correlate with his emotional state and need for validation. He explains how pursuing these desires served as a mechanism to feel alive and maintain a sense of safety by constantly striving for more.

Leo Skeppy [35:20]: "When desires cause you frustration, there's messages in them. Because now I understand the whole thing of why it kept raising. It was my way of feeling alive."

This realization led him to discern the difference between genuine desires and those driven by a subconscious need to prove self-worth. By acknowledging this, Skeppy aims to align his spending with authentic intentions rather than societal or internal pressures.

Podcast Hosting Challenges: Balancing Passion with Practicality

Shifting focus, Skeppy discusses the logistical and financial hurdles of hosting his rapidly growing podcast. Transitioning between different hosting platforms has proven problematic, leading to loss of listeners and increased costs.

Leo Skeppy [50:10]: "I'm not paying every single month to put out my podcasts for free. I'm not doing it. I'm not putting myself in that position."

Faced with mounting hosting fees due to the podcast's popularity, Skeppy contemplates either absorbing the costs, introducing minimal programmatic ads, or ceasing audio distribution altogether. Seeking advice from his Substack community, he opts for a balanced approach by incorporating brief ads to offset hosting expenses without compromising the listener experience.

Building Support Systems: The Role of Trusted Relationships

Throughout the episode, Skeppy emphasizes the importance of having reliable support systems. He highlights his relationship with JWoww, a long-time follower and trusted confidante, who provides unwavering honesty and assistance.

Leo Skeppy [60:35]: "JWoww is someone who has followed me for years now. And now when I have issues or concerns, I text her because she ain't gonna bullshit me."

Such relationships reinforce Skeppy's self-trust journey, demonstrating that leaning on trusted individuals can complement one's internal intuition, especially during challenging times.

Conclusions: The Essence of Self-Trust and Authentic Living

In wrapping up, Skeppy reflects on his transformation from someone who used to "hurt themselves to prove a point" to a person who values self-respect and the well-being of others. He underscores the significance of discerning genuine desires from those driven by inertia or the need for validation.

Leo Skeppy [78:50]: "Self trust, it's like, you used to hurt yourself to prove a point fully, and now I can't prove the point by hurting myself because I'd have to hurt you guys in the process."

Skeppy's journey encapsulates the struggle and eventual harmony between trusting one's inner voice and maintaining rational decision-making. By honoring his intuition and building supportive relationships, he navigates both personal and professional landscapes with greater clarity and authenticity.

Key Takeaways:

1. Avoid Profit Splits: Skeppy warns against entering business deals with profit splits due to the potential for financial exploitation.

2. Honor Intuition: Trusting one's inner voice is crucial, even when decisions don't make immediate logical sense.

3. Decode Desires: Understand the underlying reasons for strong desires to ensure they align with personal growth rather than external validation.

4. Manage Practical Challenges: Balancing passion projects like podcasts with practical considerations is essential for sustainability.

5. Build Support Systems: Having trusted individuals provides a safety net and reinforces self-trust.

Notable Quotes:

• [00:02]: "This set is not how it's supposed to go. It’s not how it's supposed to look. But I'm just going to trust it and follow it."

• [05:30]: "If you are ever dealing with someone in business and they say they will give you a profit split, do not take it."

• [12:15]: "My soul is telling me no. It's not aggressive or mean or panic. It was just like no."

• [35:20]: "When desires cause you frustration, there's messages in them."

• [50:10]: "I'm not paying every single month to put out my podcasts for free. I'm not doing it."

• [60:35]: "JWoww is someone who has followed me for years now. And now when I have issues or concerns, I text her because she ain't gonna bullshit me."

• [78:50]: "Self trust, it's like, you used to hurt yourself to prove a point fully, and now I can't prove the point by hurting myself because I'd have to hurt you guys in the process."

Final Thoughts

Episode 40 of Aware and Aggravated serves as a profound exploration of self-trust, intertwining personal anecdotes with valuable lessons. Leo Skeppy's vulnerability and honesty offer listeners a roadmap to navigating their own inner conflicts and fostering genuine self-reliance. By sharing his journey, Skeppy not only enlightens but also inspires others to listen to their souls, trust their instincts, and live authentically.