In this episode of Drip Trickle Flow Flood, we sit down with the brilliant Jessie Rosen, USA Today bestselling author of The Heirloom and All the Signs, screenwriter for major studios like Warner Brothers and Netflix, and creator of a Substack newsletter all about bravery. Jessie opens up about the realities of money as a creative in Los Angeles: the shame, the hustle, the luck, the leverage, and the life choices that shape not just a career, but a sustainable and fulfilling life.

Takeaways from this episode:

• Why money conversations can feel taboo among creatives.
• The mix of luck, leverage, skill, and tenacity that shapes creative pay in Hollywood.
• How Jessie built multiple income streams: from writing, teaching, copy gigs, and publishing, to Airbnb hosting.
• The hidden shame many creatives feel about side hustles.
• Why comparing your behind-the-scenes to someone else’s highlight reel is a losing game.
• Jessie’s reckoning with what she truly wanted her life to feel like, and how money became a tool for designing that life.
• The importance of financial literacy, asking “embarrassing” money questions, and saving early for long-term freedom.

Links

Check out Jessie’s website and buy her books

Subscribe to Jessie’s Substack

Tony’s website

Melissa’s website

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Disclaimer:

The information provided in this podcast is for informational and entertainment purposes only and should not be considered financial, investment, tax, or legal advice. The opinions expressed by the hosts and guests are solely their own and do not reflect the views of any companies or organizations they may be affiliated with.

Listeners should conduct their own research and consult with a qualified financial professional before making any investment or financial decisions. While we strive for accuracy, we do not guarantee that the information presented is complete, current, or applicable to your specific situation. Investing involves risk, including potential loss of principal.

By listening to this podcast, you acknowledge and agree that the hosts, guests, and producers are not responsible for any financial decisions you make based on the content discussed.