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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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
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Take the Productivity Quiz

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