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.
