Nate’s Substack
natesnewsletter.skystack.xyz
Nate’s Substack
@natesnewsletter.skystack.xyz
Daily newsletters from the cutting edge of AI, including breaking news, strategy, product breakdowns, and thought pieces.


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Grab my AI Gap-Finder Kit for Operators: 4 Prompts, 5 Areas About to Unlock, the QA Harness That Catches Breaks, and More! • Faster than a speeding...nano banana lol. But seriously, things are about to move faster than we've ever seen--here's how to not only keep up, but get ahead.
Grab my AI Gap-Finder Kit for Operators: 4 Prompts, 5 Areas About to Unlock, the QA Harness That Catches Breaks, and More!
Faster than a speeding...nano banana lol. But seriously, things are about to move faster than we've ever seen--here's how to not only keep up, but get ahead.
natesnewsletter.substack.com
December 26, 2025 at 2:17 PM
Year-end reflections: Why 2025 was a pretty good year for AI (But not for the reasons you think) • All things considered, 2025 was a pretty amazing year for AI. What worked, what didn't, and what surprised me the most--in a good way (I promise this isn't corny!)
Year-end reflections: Why 2025 was a pretty good year for AI (But not for the reasons you think)
All things considered, 2025 was a pretty amazing year for AI. What worked, what didn't, and what surprised me the most--in a good way (I promise this isn't corny!)
natesnewsletter.substack.com
December 25, 2025 at 5:14 PM
9 bets I'm making on AI in 2026 + the audit I use to spot real systems • Call me sentimental but, after some reflection, I'm starting to think things are looking up for AI in 2026.
9 bets I'm making on AI in 2026 + the audit I use to spot real systems
Call me sentimental but, after some reflection, I'm starting to think things are looking up for AI in 2026.
natesnewsletter.substack.com
December 24, 2025 at 5:11 PM
Hallucinations Aren’t the Danger—Fake Confidence IS Risky (Grab My Stay Sane Adversarial Self-Check Kit) • Even the smartest people can fall into the AI overconfidence trap. And that's risky for us, our jobs, and our teams. Here's how to make sure you stay sane (and yes, there are prompts).
Hallucinations Aren’t the Danger—Fake Confidence IS Risky (Grab My Stay Sane Adversarial Self-Check Kit)
Even the smartest people can fall into the AI overconfidence trap. And that's risky for us, our jobs, and our teams. Here's how to make sure you stay sane (and yes, there are prompts).
natesnewsletter.substack.com
December 23, 2025 at 2:16 PM
I’ve reviewed 20+ enterprise AI builds this year—they all skip this conversation + 7 prompts that force it before anyone writes code • Why “what does good look like?” is the only AI question that really matters.
I’ve reviewed 20+ enterprise AI builds this year—they all skip this conversation + 7 prompts that force it before anyone writes code
Why “what does good look like?” is the only AI question that really matters.
natesnewsletter.substack.com
December 16, 2025 at 5:14 PM
Executive Briefing: What Cursor’s $57K CMS Deletion Reveals About Where Agent Value Actually Lives • Agents aren't helpful if your software is stuck in the 2010's. Agents can't fully unlock your workflows if most of your work is in clicky old-fashioned software. Here's what your agents need to cook!
Executive Briefing: What Cursor’s $57K CMS Deletion Reveals About Where Agent Value Actually Lives
Agents aren't helpful if your software is stuck in the 2010's. Agents can't fully unlock your workflows if most of your work is in clicky old-fashioned software. Here's what your agents need to cook!
natesnewsletter.substack.com
December 14, 2025 at 5:14 PM
20 Hours of AI News in 10 Minutes + a Prompt to Cut Through the Noise and Find What Matters for YOU • This week's signal vs. noise—from GPT-5.2's panicked launch to humanoid robots sorting packages, smuggled Nvidia chips, and more!
20 Hours of AI News in 10 Minutes + a Prompt to Cut Through the Noise and Find What Matters for YOU
This week's signal vs. noise—from GPT-5.2's panicked launch to humanoid robots sorting packages, smuggled Nvidia chips, and more!
natesnewsletter.substack.com
December 13, 2025 at 5:11 PM
Grab the 9 prompts I use to turn docs into practice reps + a 90-day pilot you can steal • The case for deliberate practice in knowledge work and why I think knowledge workers should train like athletes.
Grab the 9 prompts I use to turn docs into practice reps + a 90-day pilot you can steal
The case for deliberate practice in knowledge work and why I think knowledge workers should train like athletes.
natesnewsletter.substack.com
December 11, 2025 at 2:16 PM
I filtered 21,000 AI papers so you don’t have to + grab the 8 strategy prompts I’m using for 2026 • Seriously, 21,000 papers at the premier AI conference of the year. Here's what mattered, what you can safely ignore, and the implications for 2026, plus 8 prompts to apply it to your business.
I filtered 21,000 AI papers so you don’t have to + grab the 8 strategy prompts I’m using for 2026
Seriously, 21,000 papers at the premier AI conference of the year. Here's what mattered, what you can safely ignore, and the implications for 2026, plus 8 prompts to apply it to your business.
natesnewsletter.substack.com
December 10, 2025 at 2:16 PM
Grab the 18 prompts I use to diagnose why my days feel wrecked + the math that finally made bad days make sense • My honest field notes on why "try harder" never fixed my focus .
Grab the 18 prompts I use to diagnose why my days feel wrecked + the math that finally made bad days make sense
My honest field notes on why "try harder" never fixed my focus .
natesnewsletter.substack.com
December 8, 2025 at 2:17 PM
Executive Briefing: The Memory Gap Killing Your Enterprise Agent Investments
Executive Briefing: The Memory Gap Killing Your Enterprise Agent Investments
natesnewsletter.substack.com
December 7, 2025 at 5:19 PM
The AI Resume Survival Guide (for 2025 and Beyond) • Resumes aren't doing their jobs anymore because of AI. So I wrote a reset for the AI age: how to talk about AI well, how to use AI in resume creation, and how to handle AI resume checkers
The AI Resume Survival Guide (for 2025 and Beyond)
Resumes aren't doing their jobs anymore because of AI. So I wrote a reset for the AI age: how to talk about AI well, how to use AI in resume creation, and how to handle AI resume checkers
natesnewsletter.substack.com
December 7, 2025 at 2:18 AM
Grab the 4 accessibility prompts I use before shipping AI products + the audit framework that catches what automated tools miss
Grab the 4 accessibility prompts I use before shipping AI products + the audit framework that catches what automated tools miss
natesnewsletter.substack.com
December 6, 2025 at 2:20 PM
Grab the 10 prompts I use to decompose AI workflows into atomic tasks + the debugging template that saves hours of random iteration • Stop asking which model. Start asking which task.
Grab the 10 prompts I use to decompose AI workflows into atomic tasks + the debugging template that saves hours of random iteration
Stop asking which model. Start asking which task.
natesnewsletter.substack.com
December 5, 2025 at 2:14 PM
I Finally Cracked Why AI Agent Projects Keep Failing—And I Built a Workbook with 11 Prompts So You Can Fix Yours Tomorrow • Why Your AI Agents Keep Failing (And the Edge-First Framework That Actually Works)
I Finally Cracked Why AI Agent Projects Keep Failing—And I Built a Workbook with 11 Prompts So You Can Fix Yours Tomorrow
Why Your AI Agents Keep Failing (And the Edge-First Framework That Actually Works)
natesnewsletter.substack.com
December 4, 2025 at 2:16 PM
Get Power Steering for Nano Banana Pro: Grab my world-first translator Prompt that Takes YOUR idea and turns it into perfect images on Nano Banana Pro
Get Power Steering for Nano Banana Pro: Grab my world-first translator Prompt that Takes YOUR idea and turns it into perfect images on Nano Banana Pro
natesnewsletter.substack.com
December 3, 2025 at 5:18 PM
PMs Have It Worst in the Al Era--But
There's Hope: 4 Timeless Skills that Keep You Hired
PMs Have It Worst in the Al Era--But There's Hope: 4 Timeless Skills that Keep You Hired
natesnewsletter.substack.com
December 2, 2025 at 2:17 PM
2026 Sneak Peek: The First Job-by-Job Guide to AI Evolution • Exactly how 15 top jobs mutate into next year—plus the 12 massive roles emerging right now
2026 Sneak Peek: The First Job-by-Job Guide to AI Evolution
Exactly how 15 top jobs mutate into next year—plus the 12 massive roles emerging right now
natesnewsletter.substack.com
November 30, 2025 at 2:13 AM
Executive Briefing: Daily Deep AI Adoption is a Silent Crisis—Here's My Take on How to Drive It + Takeaways From a 20 Year Industry Vet + A Custom Prompt to Get Started • The strategic question has flipped. It's no longer "Does AI work?" It's "Where do we still matter when it's everywhere?"
Executive Briefing: Daily Deep AI Adoption is a Silent Crisis—Here's My Take on How to Drive It + Takeaways From a 20 Year Industry Vet + A Custom Prompt to Get Started
The strategic question has flipped. It's no longer "Does AI work?" It's "Where do we still matter when it's everywhere?"
natesnewsletter.substack.com
November 23, 2025 at 5:15 PM
Raising Humans in the Age of AI: A Practical Guide for Parents • Most articles focus on fear or don't how and why AI works: this guide offers a practical explanation of AI for parents, and a skills framework to help parents coach kids on real-world AI usage.
Raising Humans in the Age of AI: A Practical Guide for Parents
Most articles focus on fear or don't how and why AI works: this guide offers a practical explanation of AI for parents, and a skills framework to help parents coach kids on real-world AI usage.
natesnewsletter.substack.com
November 23, 2025 at 2:16 AM
My Lab Notes on Gemini 3 vs. ChatGPT 5.1: How To Prompt EACH Model + A Custom Meta-Prompt to Build YOUR Prompts • I got my hands dirty comparing ChatGPT 5.1 vs Gemini 3 and I discovered novel prompting strategies that work better on each model. Here's my complete breakdown + a custom prompt to help!
My Lab Notes on Gemini 3 vs. ChatGPT 5.1: How To Prompt EACH Model + A Custom Meta-Prompt to Build YOUR Prompts
I got my hands dirty comparing ChatGPT 5.1 vs Gemini 3 and I discovered novel prompting strategies that work better on each model. Here's my complete breakdown + a custom prompt to help!
natesnewsletter.substack.com
November 21, 2025 at 4:00 PM
I Tested Gemini 3 And It's The Real Deal: Grab My Take + Custom Prompt to See The Impact on Your Role • I put Gemini 3 through its paces and developed the first look at how Gemini 3 is going to shift workflows across the enterprise, plus a custom prompt that explains how to apply it at work today!
I Tested Gemini 3 And It's The Real Deal: Grab My Take + Custom Prompt to See The Impact on Your Role
I put Gemini 3 through its paces and developed the first look at how Gemini 3 is going to shift workflows across the enterprise, plus a custom prompt that explains how to apply it at work today!
natesnewsletter.substack.com
November 21, 2025 at 4:00 PM
Grab the AI Native Job Prompt—A Custom Guide to Make YOUR Role AI Native in 2026 • I think we're asking the wrong question about AI and jobs. Instead of looking for NEW AI roles, the real question we should be asking is: how can we turn our current roles into AI roles? Here's how...
Grab the AI Native Job Prompt—A Custom Guide to Make YOUR Role AI Native in 2026
I think we're asking the wrong question about AI and jobs. Instead of looking for NEW AI roles, the real question we should be asking is: how can we turn our current roles into AI roles? Here's how...
natesnewsletter.substack.com
November 21, 2025 at 4:00 PM
Grab My Prompt To Help Find the 1% of AI Tools That Actually Work (+50 Tool Reviews to Get Started) • The AI tool market is exploding faster than anyone can keep up—this post dives into how to cut through the hype and find a tool that works for you—includes research on 50 tools and a custom prompt!
Grab My Prompt To Help Find the 1% of AI Tools That Actually Work (+50 Tool Reviews to Get Started)
The AI tool market is exploding faster than anyone can keep up—this post dives into how to cut through the hype and find a tool that works for you—includes research on 50 tools and a custom prompt!
natesnewsletter.substack.com
November 21, 2025 at 4:00 PM
ChatGPT Hack Exposed: There's a Real Zero-Click Vulnerability OpenAI Hasn't Yet Fixed • I spent more than 15 hours this week digging through AI news to get you the 6 stories that really matter in 6 minutes. Here they are—plus a conversational prompt so you can apply them in your context!
ChatGPT Hack Exposed: There's a Real Zero-Click Vulnerability OpenAI Hasn't Yet Fixed
I spent more than 15 hours this week digging through AI news to get you the 6 stories that really matter in 6 minutes. Here they are—plus a conversational prompt so you can apply them in your context!
natesnewsletter.substack.com
November 21, 2025 at 4:00 PM