The White-Collar Shakeup & How to Stay Ahead with Neil Shepherd

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/

Email: ⁠hello@promptlyspeakingpod.com⁠