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Jessica Lee Weiss, Esq.

Entertainment & Business Attorney | Intellectual Property Advocate

With over 20 years of experience, Jessica Lee Weiss has built a diverse and accomplished career in business, entertainment, and real estate law. She has worked with some of the most influential names and companies in the industry, providing strategic legal counsel to artists, entrepreneurs, and business owners.

Professional Experience & Industry Expertise

  • Tuff Gong Worldwide
  • Nederlander Concerts
  • The Weinstein Company
  • The Agency Group
  • Major live venues
  • Music Festivals

Experience

Her expertise spans contract negotiation, intellectual property protection, licensing, and business structuring in both entertainment and corporate sectors.
In addition to her legal career, Ms. Weiss has successfully managed and operated multiple businesses with her husband, specializing in:
Entertainment
Asset Purchases
Business Development
Intellectual Property

California State Bar

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New York State Bar

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California Certified Mediator

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California Real Estate License

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Commitment to Clients & Legal Excellence

Jessica is known for her client-first approach, ensuring each client receives comprehensive legal protection and strategic guidance tailored to their specific needs. Whether advocating for artists, business owners, or real estate investors, she brings a wealth of knowledge, experience, and a passion for protecting her clients' interests.
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Approaching Life - Substack

The Details of Life vs. The Big Picture 


Effective approaches to business relationships, negotiating deals, finding and holding leverage efficiently, navigating conflict by managing toward goals, structuring business.


Written By Jessica Lee Weiss, Esq.

Approaching Life Overview

  • The Details of Life vs. The Big Picture:
  • The Personal Narratives, World News, Negotiation & Communication Edition

The Approaching Life Newsletter distills complex ideas into clear, practical insights on how we can and should think, communicate, and navigate life. It bridges everyday wisdom with fresh approaches to help us shape our lives with greater clarity and purpose.

Core of the Approaching Life Work

  • Navigating life’s complexities—how we perceive information and then compartmentalize, push through, and connect with the world around us, as it relates to work, local and world news, relationships, and communication.

     

    ✅ Face life’s challenges with grace and class.

     

    ✅ Take accountability. Reflect. Learn new skills.

     

    ✅ Make as many fun memories as possible along the way.

     

    💡 What can we control? Only how we respond to the world around us.

     

Approaching Life Takeaways

Approaching Life Individually:

How we navigate personal growth at home and in private.

Approaching Life Collectively:

How we interpret and engage with the world, from family and relationships to work, politics, and current events.

  • Can one person know everything?

    I wish. But knowledge isn’t just about answers—it’s about the questions we continue to ask. The more we explore, the more we realize how much we don’t yet know there is to uncover to our understanding.

  • The only constant is change.

    Ideas evolve. Perspectives shift. The more we engage with different viewpoints—questioning before concluding—the stronger our thinking becomes. The moment we stop questioning, we stop growing.

    Understanding is not about defending a position, but about refining it. Ask what more there is to know.

  • We are all doing our best.
    Show grace, speak respectfully, and only respond to respectful communication. Choose to connect rather than divide. Thoughtful dialogue isn’t about proving a point; it’s about seeing if you can discover something new. We can only do this through respectful communication or debate. Respect allows us to engage fully, even when we disagree. Instead of getting sidetracked with character attacks or avoidance tactics, stronger minds can stay focused on an actually discussing the topic.

     

    The best conversations happen when we truly listen to learn.

 

  • Conversations evolve.
    Every topic is a discussion, and discussions should be revisited. We may disagree, but we can handle it. Can you handle it?

    The most meaningful discussions are revisited as needed, leading to new ideas to try, then refine in time. Exploring different viewpoints makes us sharper, not further apart. Can we challenge ideas while staying connected? Can we challenge ideas in a way that moves us forward?

    The most valuable discussions don’t end—they deepen.

  • Warning – I will debate you.
    And I hope you debate me back. Let’s go.
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Approaching Life

  • The Details of Life vs. The Big Picture.
  • The Personal Narrative, World News,
  • Negotiation + Communication Edition.

After 20+ years in business and entertainment, 11+ years of marriage, 8+ years of parenting, 43+ years of being a sister, daughter and friend, here are some Takeaways on how you can be Approaching Life individually, things to consider for yourself, and how you can be Approaching Life collectively, meaning how to decipher, compartmentalize, push through, view, and connect through the world around us – work, news, people, communication, anything legal.

Core of the Approaching Life Book

  • Get through the hard parts of life with grace and class. Take accountability. Reflect. Learn new tools. Falling forward is learning—never failing.
  • Create as many fun memories as possible the rest of the time.

💡 What can we control? Only how we respond to the world around us.

  • Approaching Life personally – How do we navigate personal growth at home and in private?
  • Approaching Life collectively – How do we interpret and engage with the world, from family and relationships to work, politics, and current events?

Approaching Life Takeaways

  • Can one person know everything?
    No. I wish.
    The more we learn, the more we realize how much we don’t know.
  • The only constant is change.
    We must stay curious and open. Here is my current understanding, but what else is going on?
  • We are all doing our best.
    Show grace—to others and to yourself. Choose to connect rather than divide.
  • Conversations evolve.
    Every topic is a discussion, and discussions should be revisited. We may disagree, but we can handle it. Can you handle it?
  • Warning – I will debate you.
    And I hope you debate me back. Let’s do this.

The Mask We Wear

In Approaching Life, we explore:
1️⃣ Taking off your mask at home – Approaching Life privately.
2️⃣ Redesigning the mask you wear in public – Using proven skills and strategies.

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