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Posts by Stephen Pao

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A Familiar Town Hall, a Sharper Edge What people are asking now, and why protest keeps coming up

A familiar town hall felt different this year. Harder questions, tighter limits, and why participation still matters.
www.retiredpdx.com/p/a-familiar...

1 week ago 0 1 0 0

I echo this sentiment.

2 weeks ago 0 0 0 0
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Separating Meaning from Voice in Product Marketing How AI enables a clearer division of responsibilities, and where that division breaks down

Most problems people blame on “AI writing” aren’t about models or prompts.
They’re about who owns meaning.
I wrote this up as a longer piece here →
#ProductMarketing #AIinMarketing #ContentStrategy
www.retiredpdx.com//p/separatin...

2 weeks ago 1 0 0 0
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Vibe Coding in Practice What building a real scheduling tool taught me

I tried building a real scheduling tool with AI. It worked faster than I expected—and broke in ways I didn’t. Some reflections,,, open.substack.com/pub/retiredp...

3 weeks ago 1 0 1 0
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The Unreliable Assistant Notes from the bleeding edge of AI deployment

AI can be operationally fragile and confidently wrong at the same time. That’s the reliability problem no demo shows.
www.retiredpdx.com/p/the-unreli...

4 weeks ago 0 0 0 0
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Running OpenClaw AI Three tradeoffs I did not expect

What surprised me about running OpenClaw wasn’t the tech. It was how often I had to choose which tradeoff I could live with.
www.retiredpdx.com/p/running-op...

1 month ago 0 0 0 0
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I Switched My Internet Provider It Will Not Be Enough

I switched ISPs to protest ICE contracts. It was easy, private, and largely symbolic. The real question is what happens when symbolism isn't enough. www.retiredpdx.com/p/i-switched...

1 month ago 0 0 0 0
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Teaching a New Assistant How to Be Useful Lessons from a day of configuring OpenClaw permissions and constraints

Teaching an AI assistant to be useful isn't just about the tech. It's about deciding what values to encode and what boundaries to keep. www.retiredpdx.com/p/teaching-a...

1 month ago 0 0 0 0
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AT&T, ICE, and My Internet Why I May Leave QuantumFiber

Leaning toward a #QuantumFiber boycott after AT&T’s ICE ties and Lumen’s sale. When the choice is real, I’d rather act. www.retiredpdx.com/p/at-and-t-i...

1 month ago 0 0 0 0
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An Accidental AI Convert There is hope even for a Retired Techie

I was an early AI experimenter but a late adopter. Turns out the problem wasn’t AI. It was my assumptions. 2 days of “vibe coding” changed that. www.retiredpdx.com/p/an-acciden...

2 months ago 0 0 0 0
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Am I Being Nudged? Right-wing foreign policy media hitting my feed

Lately I’ve noticed my feed trying to change how I see U.S. foreign policy. Not with conspiracies—but with polished, “reasonable” arguments.
www.retiredpdx.com/p/am-i-being...

2 months ago 0 0 0 0
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Alien vs. Predator, but for Streaming Why I’m Hitting Pause

I don’t want either Netflix or Paramount to control WBD. For now, I’m taking a pause from those services to protest a little, save some money, and give my brain a rest from streaming. A triple win. www.retiredpdx.com/p/alien-vs-p...

3 months ago 0 0 0 0
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Nyquist didn’t just invent—he amplified others. At Bell Labs, proximity bred brilliance. Remote can’t match that. #ReturnToInnovation

4 months ago 0 0 0 0
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I Technically Met My Goals Why doesn’t it feel like it to me?

open.substack.com/pub/retiredp...

4 months ago 0 0 0 0
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SMART goals are less appropriate when applied to situations that aren’t about execution! Clip from episode of my podcast.

4 months ago 0 0 1 0
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Check out episode 10 of my podcast where I discuss the government shutdown, ACA subsidies, and the filibuster.
www.retiredpdx.com/p/episode-01...

4 months ago 0 0 0 0
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Just returned from a Bay Area trip visiting old friends. What strikes me is how work became the foundation for decades-long relationships spanning multiple life phases. I don't envy young people starting careers in fully remote environments. www.retiredpdx.com/p/a-long-dri...

5 months ago 0 0 1 0
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Google Search AI gives balanced summaries about Biden's decline and Reagan's Alzheimer's. But search Trump and dementia? No AI overview—just raw results.
Google has the data, but withholds it due to "political sensitivity."
www.retiredpdx.com/p/e006-polit...

5 months ago 1 0 0 0
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We had our 40th high school reunion over the weekend, and I shared a “top 10” list of reflections on my podcast. The common conversation topics was #5 on the list. #40YearReunion #BellevueWA #NewportKnights www.retiredpdx.com/p/e003-old-f...

6 months ago 1 0 0 0
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Excerpt from my first Retired Techie podcast episode where I discuss how “eat your own dog food” was a success pattern for tech companies.
www.retiredpdx.com/p/episode-00...

6 months ago 1 0 0 0
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Space-Time Continuum of Family Decluttering When Two Projects Teach the Same Lessons

We discovered a hole in the space-time continuum while decluttering her childhood bedroom. No matter how much we remove, more stuff magically appears! Plus: why digitizing vinyl is way harder than expected. Two projects, same lesson. www.retiredpdx.com/p/space-time...

7 months ago 1 0 0 0
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I Realized I Was Writing in Iterations And why I’m shifting toward raw reflections

Starting in year 2 of my Substack, I’ll be shifting gears: recording raw verbal reflections on a podcast with an AI notetaker. More topical posts may follow, but for now, I’ll be more free flowing and conversational.
www.retiredpdx.com/p/i-realized...

7 months ago 0 0 0 0
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When Technology Becomes My Doctor Monitoring the care of my toe injury with Apple Fitness and ChatGPT

My Apple Watch shames me for resting an injured foot (declining steps = "failure")
ChatGPT accurately diagnosed my toe but feels like "cheating"
When did we get so attached to our metrics and suspicious of helpful AI?
www.retiredpdx.com/p/when-techn...

7 months ago 0 0 0 0
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Deleting Emails Won’t Save the Planet But the claim does generate headlines

I’m a retired techie. When the UK said deleting emails could meaningfully save water, I cringed. It’s really clickbait climate advice—novel, misleading, and headline-driven. I wish media hadn’t evolved to this. www.retiredpdx.com/p/deleting-e...

7 months ago 0 0 0 0
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A Pleasant “After Burn” Reflecting on my first hot sauce festival experience

🔥 I wrote about the “after burn” from an unforgettable day at the #PDXHotSauceExpo! From award-winning sauces to wrestling and craft beer, this festival was pure 🔥🌶️🍺
My take: www.retiredpdx.com/p/a-pleasant...
#hotsauce #Portland

7 months ago 0 0 0 0
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Democracy in Trifecta, Gerrymandering, and Walkouts Reflections from Oregon's Political Battles

Living in Oregon taught me lessons in politics. I used to oppose walkouts—until gerrymandering silenced voices. Why I reluctantly support "fighting fire with fire" www.retiredpdx.com/p/democracy-... #Gerrymandering #Democracy #Oregon #Redistricting #Politics #VotingRights

7 months ago 1 0 0 1
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Cleaning an Old Family Home Room-by-Room Navigating the overwhelming task of clearing decades of memories

Clearing a lifetime of belongings from the old family home has felt overwhelming. Our first approach wasn't working, so we're trying something new: tackle one room completely instead of making endless passes. Here's our plan (and hope) 🤞
www.retiredpdx.com/p/cleaning-a...

7 months ago 0 0 0 0
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My Oracle Data Browser V1.0 demo disk from 1992 still works! The seeds of what we did back then are still relevant today! End user access / SQL abstraction / interactive data exploration! My take: www.retiredpdx.com/p/before-ai-...
#Oracle #SQL #DSS #EIS #BI #DataIntelligence #TechHistory

7 months ago 2 0 0 0
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MileagePlus Rewards in Retirement: A Different Game Entirely How airline miles and credit card strategies change when your travel patterns shift

Retirement award travel is more complicated than business travel ever was. United's mileage pools solve one problem (booking together) but create others (can't use pooled miles for upgrades, 24-hour delays). 😅 Read more here. www.retiredpdx.com/p/mileageplu...

8 months ago 1 1 0 0
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How My 1990s Startup Helped Pioneer Web Conferencing From Telephone Conference Calls to Zoom

Behind every Zoom call you join now was a history of adoption of rich meeting tech. Our 1990s startup, Latitude, built servers to in-house voice and data conferencing. Browser-based sharing & VoIP followed. All over 20 yrs ago! www.retiredpdx.com/p/how-my-199...

8 months ago 0 0 0 0