Stephen Pao
@retiredpdx.substack.com
Cofounder, partner, angel investor, and advisor to early stage companies.
Check out episode 10 of my podcast where I discuss the government shutdown, ACA subsidies, and the filibuster.
www.retiredpdx.com/p/episode-01...
www.retiredpdx.com/p/episode-01...
November 4, 2025 at 1:38 AM
Check out episode 10 of my podcast where I discuss the government shutdown, ACA subsidies, and the filibuster.
www.retiredpdx.com/p/episode-01...
www.retiredpdx.com/p/episode-01...
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...
October 21, 2025 at 6:26 AM
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...
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...
Google has the data, but withholds it due to "political sensitivity."
www.retiredpdx.com/p/e006-polit...
October 7, 2025 at 4:41 PM
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...
Google has the data, but withholds it due to "political sensitivity."
www.retiredpdx.com/p/e006-polit...
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...
September 15, 2025 at 6:37 PM
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...
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...
www.retiredpdx.com/p/episode-00...
September 3, 2025 at 5:48 PM
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...
www.retiredpdx.com/p/episode-00...
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
August 29, 2025 at 8:13 PM
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...
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...
www.retiredpdx.com/p/i-realized...
I Realized I Was Writing in Iterations
And why I’m shifting toward raw reflections
www.retiredpdx.com
August 20, 2025 at 1:45 AM
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...
www.retiredpdx.com/p/i-realized...
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...
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
August 18, 2025 at 2:29 AM
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...
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...
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
August 14, 2025 at 4:57 AM
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...
🔥 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
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
August 11, 2025 at 10:18 PM
🔥 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
My take: www.retiredpdx.com/p/a-pleasant...
#hotsauce #Portland
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
August 8, 2025 at 8:02 PM
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
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...
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
August 6, 2025 at 1:49 PM
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...
www.retiredpdx.com/p/cleaning-a...
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
#Oracle #SQL #DSS #EIS #BI #DataIntelligence #TechHistory
August 2, 2025 at 2:28 PM
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
#Oracle #SQL #DSS #EIS #BI #DataIntelligence #TechHistory
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
July 30, 2025 at 2:11 AM
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...
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
July 27, 2025 at 2:11 PM
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...
“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...
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
July 24, 2025 at 6:51 PM
“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...
I’m choosing not to look away from authoritarianism, disinformation, and silence. #DemocracyMatters #CivicEngagement #GoodTroubleLivesOn #NoKings #HandsOff www.retiredpdx.com/p/not-lookin...
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...
#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
July 21, 2025 at 7:12 PM
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...
#Pacmodo #ModularBackpack #UrbanLifeHacks
Read the full story: www.retiredpdx.com/p/beyond-tra...
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
July 20, 2025 at 9:30 PM
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-...
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...
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
July 14, 2025 at 12:42 AM
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...
Here’s how my view of cars shifted—from personal branding to functionality. #CarCulture #TechLife #EV #AppleCarPlay www.retiredpdx.com/p/from-statu...
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
July 10, 2025 at 3:24 AM
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...
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
www.retiredpdx.com/p/from-blog-...
#AItools #ContentCreation #MicrosoftCopilot #GoogleVids
July 7, 2025 at 5:17 PM
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
www.retiredpdx.com/p/from-blog-...
#AItools #ContentCreation #MicrosoftCopilot #GoogleVids
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-...
July 3, 2025 at 12:51 PM
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-...
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
June 29, 2025 at 2:25 PM
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-...
How obsessing over my Apple Watch stats made me reflect on why everything doesn’t need to measured
www.retiredpdx.com/p/breaking-f...
www.retiredpdx.com/p/breaking-f...
Breaking free from the capitalist mindset
Old attitudes have persisted through retirement
www.retiredpdx.com
June 25, 2025 at 6:05 PM
How obsessing over my Apple Watch stats made me reflect on why everything doesn’t need to measured
www.retiredpdx.com/p/breaking-f...
www.retiredpdx.com/p/breaking-f...
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
June 23, 2025 at 11:35 PM
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...