AI Anxiety, Resistance, and Why We Need a Token Tax, with Don Shin

None of us signed up to help train superintelligence.  That’s the case Don Shin, CEO of CrossComm, makes on this episode of High Octane Leadership — and it’s just one of the uncomfortable ideas he brings to the table about AI. Don has spent 25 years building digital products, from Netscape-era websites to mobile apps to AI-driven platforms, and he tells Donald Thompson plainly: AI is a bigger shift than the internet ever was. Not because the technology is flashier, but because it automates judgment and decision-making, not just deterministic tasks — and it’s moving faster than society has time to adjust to. The conversation covers a lot of ground: why 30,000 layoffs at a profitable Oracle are really an AI-infrastructure bet, why anxiety about AI is turning into outright resistance, and Don’s case for a “token tax” — a proposal to tax the electricity and water consumption of AI data centers so the economic gains of AI don’t just accrue to a handful of companies that trained their models on data none of us knowingly volunteered. Don shares the PROMPT framework, a five-part method for getting better results out of any AI tool, and a sobering warning about AI sycophancy: an assistant that never disagrees with you is not therapy, and it’s not friendship either. This is a conversation about where the next five years of work, leadership, and human connection are headed — and what to do about it before the choice is made for us. **Key Talking Points** - **The Abundance of Intelligence —** Don’s framework for understanding AI as an economic shift on the scale of previous “abundance” moments in history — and why this one is moving faster than any before it. - **AI Anxiety Becomes AI Resistance —** Why simply reassuring employees isn’t enough, and what leaders actually need to offer people to bring them along. - **The Case for a Token Tax —** Don’s proposal to tax the electricity and water consumption of AI data centers, and why he believes the true cost of AI tokens is being artificially subsidized. - **You’re Using Claude Wrong —** Donald’s own experience learning that an AI’s first two drafts are educated guesses — and what changes once you actually train the tool on your voice and judgment. - **The Danger of Sycophancy —** Why an AI that never disagrees with you may be a bigger risk to the next generation than job displacement. - **The PROMPT Framework —** Don’s five-part model — Persona, Request, Output, Mandatories, Priority — for getting dependable results out of any AI tool. **About the Guest** Don Shin is CEO of CrossComm, a digital product studio he founded as an undergraduate — building websites in the Netscape 1.1 era before leading the company through mobile apps, augmented and virtual reality, IoT, and now AI-driven development. A 25-plus year technology industry veteran and Duke University alum, Don is a sought-after speaker on artificial intelligence and its impact on business and society. He is the creator of the PROMPT framework, a practical model for effective AI prompting, and Speak To My Future Self, a personal AI reflection tool. **Resources** **CrossComm:** https://www.crosscomm.com/ Don Shin LinkedIn: https://www.linkedin.com/in/donshin1/ **Donald Thompson LinkedIn:** https://www.linkedin.com/in/donaldthompsonjr **Donald's Newsletter & Substack:** https://substack.com/@donaldthompsonjr **Donald's Books:** https://donaldthompson.com/books-resources/ Stay connected with Donald: Get his newsletter packed with actionable insights and the kind of straight-talk leadership intelligence that helps build authority, drive performance, and stay ahead of what’s coming next: donaldthompson.com. - (00:00) - — Cold Open: The Data We Didn't Know We Were Giving Away - (01:00) - — Welcome Don Shin, CEO of CrossComm - (02:00) - — The Abundance of Intelligence: How AI Changes the Automation Equation - (04:00) - — Why AI Is Bigger Than the Internet: Don's CrossComm Origin Story - (06:00) - — The Velocity Problem: Why Buffer Time Matters for Economic Disruption - (07:00) - — Oracle's Layoffs and the Rising Anxiety Data - (08:00) - — It's Not Just AI Anxiety, It's AI Resistance - (10:00) - — The Controversial Take: Game Theory and a Broken System - (11:00) - — The Case for a Token Tax - (13:00) - — Reddit, Data, and the Price of “Free” AI Tools - (15:00) - — You're Using Claude Wrong: Donald's Lawnmower Analogy - (18:00) - — Let AI Do the Routine So Teams Can Do the Remarkable - (20:00) - — Why Top-Down AI Mandates Failed in 2025 - (22:00) - — The Loneliness Economy: Why Therapy Is AI's #1 Use Case - (23:00) - — The Danger of AI Is Sycophancy - (27:00) - — Assigning a Persona: Why AI Defaults to Reassurance - (28:00) - — The PROMPT Framework - (31:00) - — The Next Problem: What Happens When Token Costs Explode 5–10x - (34:00) - — Closing Thoughts: Lead From the Front High Octane Leadership is hosted by The Diversity Movement CEO and executive coach Donald Thompson and is a production of Earfluence. Order UNDERESTIMATED: A CEO’S UNLIKELY PATH TO SUCCESS, by Donald Thompson.