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37. You Have To Lose Before You Win. Let It Get Ugly

By Leo Skepi

In this episode of Aware & Aggravated, host Leo discusses his decision to end significant business relationships, including his podcast deal and representation with UTA. He explains how trusting his intuition led him to make choices that others might view as risky, choosing to prioritize his values and creative vision over stable income streams and industry connections.

The episode also covers Leo's approach to developing new products and creative ventures, with a focus on maintaining authenticity rather than chasing mass appeal. He shares how meaningful coincidences have validated his career decisions, from a chance encounter leading to potential business opportunities to receiving creative inspiration for future projects like journals and other products. His sister now manages his business affairs, bringing an understanding of his values and professional approach to the role.

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37. You Have To Lose Before You Win. Let It Get Ugly

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37. You Have To Lose Before You Win. Let It Get Ugly

1-Page Summary

Changes in Professional/Business Relationships and Deals

Leo recently made significant changes to his business relationships, particularly regarding his podcast deal. Citing issues with transparency, ad interruptions, and delayed payments, Leo terminated both his podcast agreement and his representation with UTA. Moving forward, Leo has chosen his sister to manage his business affairs, noting that she deeply understands his values and professional approach after witnessing his career journey firsthand.

Leo's Internal Decision-Making Process and Following His Intuition

Despite appearing reckless to others, Leo emphasizes the importance of trusting his intuition in decision-making. He describes ending his largest income stream because his "soul wanted to," demonstrating his willingness to walk away from any opportunity that doesn't align with his values. Leo expresses that past disappointments have led him to rely primarily on himself, prioritizing integrity and authenticity over stable income or industry relationships.

Synchronicities and Signs Guiding Leo's Path Forward

Leo shares how meaningful coincidences have reinforced his trust in his path. After deciding not to pursue his nursing license, a chance encounter led to an unexpected opportunity with a construction company owner. Leo's act of generosity caught the owner's attention, leading to potential collaboration. Additionally, Leo describes receiving vivid visions and creative impulses guiding him toward specific projects, such as developing a journal and other products.

Leo's Plans for New Products and Creative Ventures

In developing new products, Leo emphasizes prioritizing his creative vision over mainstream appeal. His approach involves collaborating with partners who understand and support his process while maintaining authenticity in his creations. Rather than seeking mass appeal, Leo focuses on genuine self-expression, believing that the right audience will naturally be drawn to his work. This philosophy extends to his podcast, where he maintains creative freedom while sustaining financial independence through YouTube advertising.

1-Page Summary

Additional Materials

Counterarguments

  • Trusting intuition can sometimes lead to suboptimal decisions if not balanced with rational analysis and consideration of empirical evidence.
  • Appointing a family member to manage business affairs might introduce potential conflicts of interest or lack of professional distance.
  • Prioritizing integrity and authenticity is commendable, but it may also limit opportunities for collaboration and growth that could benefit from compromise.
  • Relying primarily on oneself can lead to isolation and may prevent one from benefiting from the expertise and support of others.
  • Interpreting coincidences as signs can be subjective and may not always lead to sound decision-making.
  • Focusing on creative vision without considering market demand could result in financial instability or failure to reach a wider audience that might appreciate the work.
  • Collaborating only with partners who support one's creative process might exclude constructive criticism that could improve the final product.
  • While maintaining creative freedom is important, some level of adaptation to audience preferences can be necessary for commercial success.
  • Sustaining financial independence through a single platform like YouTube advertising can be risky due to potential changes in platform policies, algorithms, or market trends.

Actionables

  • You can evaluate your professional relationships by creating a transparency checklist that includes factors like communication clarity, payment timelines, and respect for personal values, then use it to assess current and potential partners or collaborators. For example, before entering a new partnership, score each factor on a scale from 1 to 10 to determine if the relationship aligns with your transparency standards.
  • Develop a decision-making journal where you record instances when you follow your intuition, noting the outcomes and how they align with your personal values. This can help you track the effectiveness of intuitive decisions over time. For instance, if you feel inclined to take a new job despite it being in a different field, write down your thought process and revisit the journal after some time to evaluate the decision's impact on your life.
  • Create a "creative authenticity" plan for your projects that outlines how you will maintain your unique vision and values throughout the development process. This could involve setting specific guidelines for the types of projects you take on, the people you collaborate with, and the way you market your work. As an example, if you're a writer, decide in advance which themes you won't compromise on and choose publishing options that respect your creative control.

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37. You Have To Lose Before You Win. Let It Get Ugly

Changes in Professional/Business Relationships and Deals

The dynamics of professional relationships and deals are constantly evolving, and recently Leo has experienced a significant shift in managing his business affairs.

Leo Exited Podcast Deal Over Contract Dissatisfaction and Disrespect

Leo has expressed his decision to regain control over his professional engagements by leaving a podcast deal due to frustrations and feelings of disrespect.

Podcast Deal Frustrations: Transparency Issues and Ad Interruptions

Leo mentions that he is no longer obligated to do podcasts, highlighting his dissatisfaction with his previous podcast deal. His grievances include disliking ads interrupting the podcast, as he values the listener experience highly. Leo is particular about the ads run on his podcast, only accepting those for products he approves of. He insists on a highly negotiated and specific contract to ensure that his standards are maintained.

Leo Ended Podcast Deal and Uta Representation Due to Disrespect of Boundaries and Lack of Authenticity

Due to a lack of clear communication about payment schedules and empty promises of money being delivered the following month, Leo experienced increasing frustration. The lack of respect for contractual agreements led to Leo constantly having to chase the agreed-upon payments, making him feel disrespected. He voiced that the situation reached a boiling point for him, compromising his desire for flow and authenticity in his work. As a result, Leo decided to end his deal and his dealings with the agency UTA, citing these experiences as conflicts with his core values, despite any hesitations from his logical side.

Sister to Help Manage Leo's Business Affairs

Sister Supports Leo's Professional Decisions

Movin ...

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Changes in Professional/Business Relationships and Deals

Additional Materials

Actionables

  • You can draft a personal values statement to guide your decisions, ensuring that any partnerships or contracts you enter align with your core beliefs. Start by listing your top five values, such as transparency, respect, and authenticity. Use this list as a benchmark when evaluating new opportunities or relationships, and refer back to it when faced with difficult decisions to ensure you stay true to what's important to you.
  • Create a simple feedback system for any collaborative projects you're involved in to maintain open communication and transparency. This could be as straightforward as a shared document or a regular check-in schedule where all parties can voice concerns and updates. This practice helps to preempt misunderstandings and ensures that everyone's expectations are clear from the outset.
  • Consider involving a trusted family member or friend in you ...

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37. You Have To Lose Before You Win. Let It Get Ugly

Leo's Internal Decision-Making Process and Following His Intuition

Leo discusses the importance of trusting in himself and his own decisions, despite seeming reckless to others. He insists that when he fails to trust himself, it leads to negative consequences.

Leo Trusts His Intuition and Soul, Even in Seemingly Reckless Decisions

Leo states that he had to end his biggest stream of income because his "soul wanted to." He describes this move as the right decision, even though it might appear foolish to others. Leo finds anger but also clarity from the decision, confirming his peace with choosing to cut off the deal. He waited for podcast money that was delayed, learning to live without it, which ultimately gave him confidence in his decision. Leo shares, "This is a big source of my confidence as I'm willing to walk away from anybody and anything, no matter what happens."

Leo Only Bets On Himself, Having Been Let Down By Trusting Others

He expresses that he's difficult to manage or represent because he requires a high standard for himself. After being disrespected, Leo reveals that he cannot be told what to do. Leo hints at past disappointments caused by relying on others and reinforces his self-reliance, saying he feels not looked after by anyone.

Leo Defies Convention to Boldly Express His Authentic Self

Leo is ready to abandon any opportunity or relationship that does not resonate with his values and vision. "I'm very transparent and I move with integrity. And when you don't, we're not going to get it on because I'm going to look out for you. And when you don't look out for me..." Leo articulates his commitment to authenticity, suggesting that he would discard offe ...

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Leo's Internal Decision-Making Process and Following His Intuition

Additional Materials

Counterarguments

  • Trusting one's intuition can sometimes lead to confirmation bias, where a person may interpret situations in a way that confirms their preconceptions, potentially overlooking more rational or evidence-based decisions.
  • While self-reliance is important, collaboration and trusting others can lead to synergistic outcomes that one might not achieve alone. It's important to find a balance between self-trust and openness to others' input.
  • Defying convention can be empowering, but it's also important to recognize the value of some conventions, which may exist because they've been tested over time and found to be effec ...

Actionables

  • You can start a "gut check" journal to hone your intuition. Every day, jot down situations where you need to make a decision, and record your initial gut reaction. After you see the outcome, reflect on whether your intuition was on target. This practice will help you trust your instincts more, just like Leo.
  • Create a personal "bet on yourself" challenge where you identify a skill or project you've been hesitant to pursue because of reliance on others. Commit to working on it independently for a set period, such as 30 days, and track your progress. This will help you build self-reliance and confidence in your abilities.
  • Develop a "values vision board" that represents your core values, ...

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37. You Have To Lose Before You Win. Let It Get Ugly

Synchronicities and Signs Guiding Leo's Path Forward

Leo's journey is seemingly directed by a series of affirming events and inner guidance, showcasing the significant role of intuition in shaping his future.

Synchronicities Bolster Leo's Trust In His Intuition and Path

A crucial moment of synchronicity strengthened Leo’s trust in the unfolding of his life's path.

Leo, After Forgoing His Nursing License, Met a Construction Company Owner Excited to Work With Him

As Leo navigated through life after deciding not to pursue his nursing license, he encountered an unexpected opportunity. While moving across an intersection, he was spotted by someone he believes he was not meant to see at that moment. This chance observation, which coincided with the closure of an energetic chapter, further invigorated his trust in his soul's direction.

Leo's Generosity Sparks Unexpected Collaboration

Generosity proved to be the key that unlocked a surprising collaboration for Leo.

Upon offering assistance to someone in need, Leo caught the attention of a construction and remodeling company owner who recognized him. Their ensuing conversation revealed a mutually beneficial opportunity for them to work together. The owner had observed Leo's selfless act across the street, which prompted her interaction and subsequent enthusiasm to collaborate with him.

Leo Receives Intuitive Guidance On Creative Projects and Ideas to Pursue

Leo's life is punctuated by significant realizations that steer him towards specific creative endeavors.

Leo Receives Vivid Visions and an Urge ...

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Synchronicities and Signs Guiding Leo's Path Forward

Additional Materials

Counterarguments

  • Synchronicities may be coincidental and not necessarily indicative of a predestined path.
  • Trusting in synchronicity without critical thinking could lead to confirmation bias, where Leo only notices events that support his beliefs.
  • Forgoing a professional license in a stable field like nursing for an uncertain opportunity may not be financially prudent.
  • Acts of generosity should ideally be done without the expectation of a reward or recognition, and not all acts of kindness will lead to beneficial opportunities.
  • While intuition can be a powerful guide, it should be balanced with rational decision-making, especially in business or creative endeavors where market research and planning are impor ...

Actionables

  • You can start a synchronicity journal to track coincidences and intuitive hits in your daily life. Begin by writing down any unusual coincidences or moments when you feel a strong gut feeling about a decision or direction. Over time, review your journal to identify patterns or guidance that may be emerging from these synchronicities.
  • Create a "Yes, And" jar to encourage openness to new opportunities. Whenever you're faced with a decision that could lead to a new opportunity, write it down and place it in the jar. At the end of each week, pull out one slip and actively pursue that opportunity, even if it's outside your comfort zone, to see where it might lead.
  • Develop a personal "intuition workout" routine to strengthen your inner guidance. Set aside a few min ...

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37. You Have To Lose Before You Win. Let It Get Ugly

Leo's Plans for New Products and Creative Ventures

Leo, a creator and entrepreneur, reveals his intentions regarding new products and creative ventures, hinting at a unique approach that favors intuition and authenticity over broad market appeal and commercial success.

Leo Is Developing New Products, Like a Journal, Inspired Intuitively

Leo has begun to draw upon spontaneous inspiration for his product ideas, with indications that he's been generating concepts for novel items.

Leo's Product Ideas Prioritize Creative Vision Over Mainstream Appeal

Throughout his contemplations, Leo expresses a firm stance on creating products that align with his personal inclinations rather than designing items with mass appeal in mind. He is determined to create things that he personally desires, maintaining a sense of authenticity and integrity in his creations. His connection with creativity seems to fuel his product development, as evidenced by his ventures, which may not be universally liked but remain true to his vision.

Leo Collaborates With Partners to Bring Ideas To Life, Appreciating Their Alignment With His Process

Leo suggests a sense of collaboration in bringing his ideas to fruition. In a meeting with a manufacturing company, his pitch was met with enthusiasm and led to the generation of additional ideas, which can be seen as testament to a supportive working relationship that acknowledges his creative process.

Leo Prioritizes Authentic Self-Expression Over Commercial Success in His Creative Endeavors

Leo’s creative pursuit seems to be driven by a spiritual and expressive quest rather than a chase for commercial success.

Leo Is Uninterested In Appealing To the Masses or Compromising His Vision

Despite the uncertainty of commercial viability, Leo puts faith in the process and in his intuition. He reflects a desire to not manipulate the outcome of h ...

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Leo's Plans for New Products and Creative Ventures

Additional Materials

Counterarguments

  • While intuition can be a powerful guide, relying solely on it without market research may lead to products that don't meet any existing demand, potentially resulting in financial loss.
  • Prioritizing creative vision is admirable, but a balance between innovation and market appeal is often necessary for a business to be sustainable and reach a wider audience.
  • Collaboration is key to success, but it's important to ensure that all partners have a shared vision and that the creative process doesn't become diluted by too many conflicting ideas.
  • Authentic self-expression is important, but it must be balanced with a viable business model to ensure that the creative end ...

Actionables

  • Start a "Creative Vision" journal where you jot down ideas as they come, without filtering for market trends. Use this journal daily to capture any fleeting thoughts, sketches, or concepts that resonate with you personally. Over time, this will become a repository of your most authentic ideas, which you can revisit and develop further when you feel inspired.
  • Collaborate with a friend or family member on a small project that reflects your shared values or interests. This could be as simple as designing a unique piece of art for your home, planning a themed dinner party, or starting a mini garden. The key is to focus on the joy of creation and the strength of your relationship, rather than the potential for external validation or profit.
  • Create a piece of content, ...

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