The White-Collar Shakeup & How to Stay Ahead with Neil Shepherd
Promptly Speaking
Learning styles, culture, and experimentation
Hosts discuss learning preferences, company culture that tolerates failure, and practical ways to iterate fast with AI.
In this episode of Promptly Speaking, Sara and Dan sit down with Neil Shepherd — a Silicon Valley engineer, entrepreneur, and former leader at PayPal, Scale AI, Cohere, and Play.ai — for a direct, deeply informed look at the AI disruption already unfolding.
Neil breaks down why this wave of technology is unlike any before it, why white-collar roles are more exposed than people think, and why the next five to seven years will reshape entire industries. He dives into how AI is transforming marketing, legal work, medicine, and manufacturing in very different ways — from one-person teams running $60M campaigns to diagnostic models outperforming specialists — and what that means for your career trajectory.
He also shares his latest venture, The American Dream Index, a data-driven tool that quantifies what it truly costs to build a stable, middle-class life in America — and why so many people feel like they’re falling behind.
💡 You’ll learn:
- Why AI is moving faster than any disruption in modern history
- Which roles are most vulnerable over the next few years
- The real skill divide: entrepreneurial thinkers vs handle-turners
- How marketing, law, medicine, and manufacturing are being reshaped by ai
- What separates people who adapt from those who get left behind
- Why curiosity, experimentation, and communication are the new power skills
- How Neil is using AI to map the American dream — and why it’s drifting out of reach for many
🧠 Whether you’re an operator, a leader, or just trying to stay ahead, this conversation offers clear-eyed insight into a future that’s arriving much faster than most people expect.
⏱ Timestamps:
00:00 Disruptive Technology: Why This Wave Is Different
00:19 The American Dream and Shifting Goalposts
00:37 Meet Neil Shepherd
02:05 AI’s Acceleration and Job Disruption
06:27 Marketing’s Massive Transformation
08:58 Career Advice in the Age of AI
15:39 AI in Medicine
19:34 The Future of Robotics and Manufacturing
22:52 Entrepreneurs vs Handle-Turners
23:27 What Job Security Really Looks Like Now
24:11 Adapting to Technological Change
27:04 Introducing the American Dream Index
29:05 Meaning, Purpose, and Mid-Career Reinvention
33:32 Curiosity, Experimentation, and Adaptability
38:37 The Communication Skill That Now Sets You Apart
43:36 Final Thoughts and What to Do Next
How to Find Neil:
LinkedIn: https://www.linkedin.com/in/neilshep/
American Dream Index: www.americandreamindex.com
Follow Sara & Dan:
Sara: https://www.linkedin.com/in/saralynneroberts/
Dan: https://www.linkedin.com/in/danroberts27/
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