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Stephen Pao

Stephen Pao

@retiredpdx.substack.com

180 followers 17 following 100 posts

Cofounder, partner, angel investor, and advisor to early stage companies.

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Stephen Pao @retiredpdx.substack.com · 4d

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...

Stephen Pao @retiredpdx.substack.com · 17d

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...

Stephen Pao @retiredpdx.substack.com · Sep 15

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...

Stephen Pao @retiredpdx.substack.com · Sep 3

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...

Stephen Pao @retiredpdx.substack.com · Aug 29

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...

Space-Time Continuum of Family Decluttering

When Two Projects Teach the Same Lessons

www.retiredpdx.com

Stephen Pao @retiredpdx.substack.com · Aug 20

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...

I Realized I Was Writing in Iterations

And why I’m shifting toward raw reflections

www.retiredpdx.com

Stephen Pao @retiredpdx.substack.com · Aug 18

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...

When Technology Becomes My Doctor

Monitoring the care of my toe injury with Apple Fitness and ChatGPT

www.retiredpdx.com

Stephen Pao @retiredpdx.substack.com · Aug 14

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...

Deleting Emails Won’t Save the Planet

But the claim does generate headlines

www.retiredpdx.com

Stephen Pao @retiredpdx.substack.com · Aug 11

🔥 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

A Pleasant “After Burn”

Reflecting on my first hot sauce festival experience

www.retiredpdx.com

Stephen Pao @retiredpdx.substack.com · Aug 8

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

Democracy in Trifecta, Gerrymandering, and Walkouts

Reflections from Oregon's Political Battles

www.retiredpdx.com

Stephen Pao @retiredpdx.substack.com · Aug 6

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...

Cleaning an Old Family Home Room-by-Room

Navigating the overwhelming task of clearing decades of memories

www.retiredpdx.com

Stephen Pao @retiredpdx.substack.com · Aug 2

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

Stephen Pao @retiredpdx.substack.com · Jul 30

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...

MileagePlus Rewards in Retirement: A Different Game Entirely

How airline miles and credit card strategies change when your travel patterns shift

www.retiredpdx.com

Stephen Pao @retiredpdx.substack.com · Jul 27

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...

How My 1990s Startup Helped Pioneer Web Conferencing

From Telephone Conference Calls to Zoom

www.retiredpdx.com

Stephen Pao @retiredpdx.substack.com · Jul 24

“History doesn’t just happen in textbooks. We’re living it.”
I’m choosing not to look away from authoritarianism, disinformation, and silence. #DemocracyMatters #CivicEngagement #GoodTroubleLivesOn #NoKings #HandsOff www.retiredpdx.com/p/not-lookin...

Not Looking Away

Why I am getting more civically engaged

www.retiredpdx.com

Stephen Pao @retiredpdx.substack.com · Jul 21

Ever had to switch from casual to business formal in the middle of your day? My Pacmodo system + a trifold garment sleeve = wrinkle-free suit, no stress.
#Pacmodo #ModularBackpack #UrbanLifeHacks
Read the full story: www.retiredpdx.com/p/beyond-tra...

Beyond Travel: How My Pacmodo Solved an Unexpected Wardrobe Challenge

I have written before about how Pacmodo is my new favorite travel system. Beyond travel, I also use my Medium PAC and Modo for regular walking commutes between home and office. This past Thursday, I d...

www.retiredpdx.com

Stephen Pao @retiredpdx.substack.com · Jul 20

A random encounter with a neighbor 1.7 miles from home, sharing EV chargers, great food, beer, and police marching WITH protesters. Friends. Just another week living in Portland. Here's why I'm grateful to call PDX my home. #Portland #PDX #Gratitude www.retiredpdx.com/p/10-things-...

10 Things I Love About Portland

A Week of Gratitude – July 13-19, 2025

www.retiredpdx.com

Stephen Pao @retiredpdx.substack.com · Jul 14

My car used to reflect my personality. Now it just needs to display Google Maps and play podcasts.
Here’s how my view of cars shifted—from personal branding to functionality. #CarCulture #TechLife #EV #AppleCarPlay www.retiredpdx.com/p/from-statu...

From Status Symbol to Smart Device

How car buying changed for me

www.retiredpdx.com

Stephen Pao @retiredpdx.substack.com · Jul 10

After 23 years, I finally sold my Audi TT yesterday. Bought it at 35 during a midlife crisis with two toddlers at home—made zero practical sense. But here's what I learned about happiness, our belongings, and how we hold on to them. On Substack: www.retiredpdx.com/p/saying-goo...

Saying Goodbye to My Audi TT After 23 Years

Yesterday marked the end of an era.

www.retiredpdx.com

Stephen Pao @retiredpdx.substack.com · Jul 7

I tested AI video creation with Microsoft CoPilot + ClipChamp using the same blog post I used to test Google Vids. One was fast and slick. The other (with some wrestling) could do even better.
www.retiredpdx.com/p/from-blog-...
#AItools #ContentCreation #MicrosoftCopilot #GoogleVids

Stephen Pao @retiredpdx.substack.com · Jul 3

I turned my metrics Substack post into a video using Google Vids. AI handled the script, storyboard, and voiceover—but it felt too impersonal. To try to personalize it a bit, I added an intro, my own voice track, and replaced a clip. #AItools #GoogleVids. www.retiredpdx.com/p/from-blog-...

Stephen Pao @retiredpdx.substack.com · Jun 29

Had Claude rewrite my last blog post—cleaner, clearer, totally on-message. Is writing now more about prompt engineering than wordsmithing? I shared the rewrite, Claude’s analysis, and a poll on which version readers prefer. www.retiredpdx.com/p/rewriting-...

Rewriting a blog post with Claude AI

A quick 3-question survey (and results)

www.retiredpdx.com

Stephen Pao @retiredpdx.substack.com · Jun 25

How obsessing over my Apple Watch stats made me reflect on why everything doesn’t need to measured
www.retiredpdx.com/p/breaking-f...

Breaking free from the capitalist mindset

Old attitudes have persisted through retirement

www.retiredpdx.com

Stephen Pao @retiredpdx.substack.com · Jun 23

Great post by @rbreich.bsky.social . This is a great message, even if @lizcheney.bsky.social didn't send it! open.substack.com/pub/robertre...

A remarkable message

You need to read this.

open.substack.com

Stephen Pao @retiredpdx.substack.com · Jun 22

I spent Saturday afternoon culling through old printed photos that we’ve been carrying around through our 8 moves. Here are some tips to getting mentally ready to toss most of them. Do you have any to share?
www.retiredpdx.com/p/its-ok-to-...

It's OK to... Toss Old Printed Photos

Seven criteria to help “release”

www.retiredpdx.com