Starting with the end and breaking down costs

How do some people consistently turn raw ideas into real, finished work—while others stay stuck waiting for inspiration to strike? In this encore conversation, Thanh sits down with legendary creative entrepreneur and Parsons professor Jeffrey Madoff to unpack the mindset and structure behind sustainable creativity. From building a fashion company at 22 to producing campaigns for Ralph Lauren and Tiffany, Jeffrey shares how curiosity—not talent alone—has fueled every chapter of his career.

You’ll hear why creativity is less about magic and more about systems, how organizing principles help tame chaos, and why delegation is the secret weapon behind high-level creative output. Whether you’re a founder, maker, or someone with big ideas you haven’t yet shipped, this episode reveals the practical workflow that turns vision into execution—and makes a living from it.

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Cheat Sheet:

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• From Madison storefronts to global campaigns—meet the mind behind the work, Jeffrey Madoff. [01:19]
• The surprisingly simple tools Jeffrey relies on to keep creative chaos under control. [01:59]
• How a spontaneous leap into fashion launched a career that later pivoted into film and storytelling. [05:56]
• A refreshing definition of creativity that expands far beyond artists and into everyday builders. [16:52]
• Why waiting for inspiration is a trap—and what actually moves creative projects forward. [23:28]
• The organizing principles and delegation strategies that make big creative visions executable. [35:14]
• How to price your ideas, validate them in the real world, and prove they’re worth paying for. [42:10]

Links:

• Shopify
• Gusto
• Notion
• DripDrop
• 25X Productivity Coaching
• Madoff Productions
• A Creative Career
• Google Tasks (in Gmail)
• Trello
• YouTube
• Parsons School of Design
• Book- Creative Careers: Making a Living With Your Ideas
• Instagram
• LinkedIn
• Productivity Academy
• The Productivity Show on Youtube
• The Productivity Show Youtube Clips
• Become a member of TPS+
• Take the Productivity Quiz

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