MEMO 001 / SEASON 01

The Technology You Depend On Is Already Being Replaced

What if the companies, technology, careers and business models we think are permanent are actually just temporary bridges to something better?

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THE BRIDGE MEMOS

Published August 22, 2026 · 17:38

Published in collaboration with @awkrad ↗

ORIGINAL PUBLICATION · August 22, 2026WATCH ON YOUTUBE ↗
View the original production thumbnailOriginal production thumbnail for The Technology You Depend On Is Already Being Replaced
Chapters from the published video
  1. — Nothing Is Permanent
  2. — Kodak Had the Future
  3. — Sears Was Amazon Before Amazon
  4. — Bridges We Thought Were Permanent
  5. — The Bridges in My Own Career
  6. — AI Changes the Equation
  7. — Is Software Just an Interface?
  8. — We Can See the Pieces
  9. — What Is The Bridge?
  10. — The Next Bridge: Software
THE RECORDED WORDS

Full transcript.

Original record · August 22, 2026

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00:00:02:07 - 00:00:34:04

I think it's time to question everything. Because some of the things that we feel most permanent in our lives probably aren't. The companies we depend on. The technology we use every day. The software we build our business around. The way we communicate. The way we entertain ourselves. The careers we choose. Maybe even the things we believe will always have value.

00:00:34:06 - 00:00:57:10

Some of those things are going to be around 20 years from now. And some of them absolutely will not. And the problem is we don't know which ones yet. But maybe we can figure some of it out. Because when you really look back at technological change, there's a pattern. Humans have a need. We build something that satisfies that need.

00:00:57:10 - 00:01:23:06

And because that solution works, we start believing the solution itself is permanent. But sometimes it isn't. Sometimes it's just the best way we currently have of getting from the need to the outcome. And I've started thinking of those things as bridges. Some bridges last five years, some last 50, some last 100. But eventually somebody builds a better bridge.

00:01:23:09 - 00:01:55:17

And when that happens, the old one can become irrelevant incredibly fast. So the question behind this whole series is what are the bridges around us right now? Are we on the right ones? Where are they taking us? And most importantly, do they lead somewhere? Or are we building our careers, our companies, our investments, our entire lives on bridges to nowhere?

00:01:55:20 - 00:01:59:26

Let me show you what I mean.

00:01:59:29 - 00:02:25:27

Kodak is the first example that I'm going to use. And what's interesting, and I thought this is kind of neat. I found these lenses and these are made by Kodak, probably from the early 2000s, maybe late 2008 or 910 somewhere in there. Anyway, I just thought it was interesting that I had these, and I'm using one of these lenses to film today to give us this kind of rounded look.

00:02:25:27 - 00:02:51:00

So that's kind of cool. The Kodak two, it's a really good example. There was a time when Kodak looked impossible to kill. And Kodak especially is especially interesting to me because, you know, they're in my region. They're in Rochester, New York, which is where I shop. I even work in Rochester. I grew up around the history of Kodak.

00:02:51:01 - 00:03:22:18

I've heard the stories. I knew people that work there. And at its peak, Kodak employed an unbelievable number of people. It wasn't just a company, it was part of the economy. Part of the identity of this whole area. And Kodak wasn't merely successful, it was dominant film cameras, processing pictures. Kodak was photography. And then in 1975, which is the same year yours truly was born, an engineer built one of the first digital cameras.

00:03:22:20 - 00:03:47:21

Think about that. They didn't miss digital photography because nobody could imagine it. They didn't get blindsided 20 years later by some technology that came out of nowhere. They actually had it in 1975 inside the company. The future was literally sitting in front of them. And yet Kodak was making an enormous amount of money selling film. Film was the engine, film was the business.

00:03:47:21 - 00:04:13:20

And from where they were standing, film looked like the destination, but it wasn't. Film was just the bridge because nobody actually wanted film. Nobody woke up in the morning thinking, you know what I need more of in my life? Chemically treated strips of plastic. I mean, that's not true. A lot of people who were, you know, hobbyist or professional photographers love their film, love their product.

00:04:13:23 - 00:04:38:15

But I'm talking about the human need here. We wanted to capture moments, take pictures of your kids, your wedding, your vacation, your dog, whatever. Capture the moment. Keep it, share it, and look at it again someday. Kodak even gave us the phrase a Kodak moment. That was the actual business preserving memories. Film was simply the technology we had at the time to accomplish it.

00:04:38:17 - 00:04:55:04

Then digital came along and found a fundamentally and dramatically better bridge to the exact same human need. And eventually the bridge Kodak had spent decades dominating collapsed.

00:04:55:06 - 00:05:17:08

But there is another company whose story might bother me even more, because the more I thought about this one, the more I couldn't believe it. Sears. Sears and Roebuck. Now, depending on how old you are, Sears might mean completely different things to you if you're younger. Sears might be just some dying department store in your your parents dragged you to.

00:05:17:11 - 00:05:39:25

And I'm all. But if you're somewhere around my age, you remember what Sears actually was. Sears had the catalog, and that catalog was a big deal. I remember going to my aunt's house around Christmas time, grabbing that giant Sears catalog, going straight to the toy section and circling everything I wanted. Everything. You'd have this giant Christmas list. You ripped the page out.

00:05:39:25 - 00:06:02:07

Give it to your mom, give it to your aunt. Give it to your family. There you go. Christmas shopping. Done. But think about what Sears actually built. You sat in your house. You browse through thousands and thousands of products clothes, tools, furniture, appliances, farm equipment, toys, pretty much anything you could imagine. You decided what you wanted. You placed an order remotely and they shipped it to you.

00:06:02:10 - 00:06:25:07

And they would even sell you a house. That's right, an actual house. You could order a Sears kit house and have the materials delivered right to the job site. Now stop for a second and think about what I just described. Massive product selection, shopping from home, remote ordering, warehouses. Inventory supplier relationships, distribution, shipping directly to the customer. Returns, trusted brands.

00:06:25:15 - 00:06:50:23

Convenience. What does that sound like? Sears was Amazon before the internet existed. And that's what makes this story so damn sad, because the internet should not have killed Sears. The internet should have been the greatest thing that ever happened to Sears there. He knew how to sell remotely. They had the customers. They had the warehouse, the suppliers, distribution and trusted brands.

00:06:51:00 - 00:07:17:27

They had decades and decades of experience doing almost exactly what the internet commerce would eventually become. They already had the business model. The only thing that really changed was the interface. The catalog wasn't the business. The catalog was just the interface. And somewhere along the way, Sears lost sight of that. They started thinking the department store was the business, just like Kodak's Kodak thought film was the business.

00:07:18:00 - 00:07:43:22

And that's the pattern. Companies start confusing the bridge with the destination blockbuster. Another one wasn't really in the plastic disc rental business. People wanted entertainment. AOL wasn't really the thing we wanted, although I think everybody wanted AOL at the time, but we really just wanted access to the internet. RadioShack wasn't about little stores full of resistors and weird cables.

00:07:43:23 - 00:08:09:29

It was about giving people access to technology they couldn't easily get somewhere else. Cassette tapes, eight track CDs, DVDs, VCRs, home telephone, circuit city, blockbuster AOL all of these things were everywhere. And when we were living through them, they certainly didn't feel temporary, did they? They felt normal. They felt established. They felt like the way things worked right up until they didn't.

00:08:10:00 - 00:08:33:16

And that's what has started making me suspicious of anything that feels permanent today. Because I've watched these bridges disappear in my own career. I've spent more than 30 years working in technology, but when I was young, I didn't really know anything about computers. I computers, I was interested in them. I was curious about them, but I didn't really know how they worked.

00:08:33:18 - 00:08:52:00

At one point, I was working this horrible factory job about an hour away from my house, and I would drive by Barnes and Noble every day. One day I decided to stop, and I really couldn't afford to buy a bunch of books about computers. But Barnes and Noble had chairs and nooks and places where you could go to read books so you could grab a book, sit down and read it.

00:08:52:00 - 00:09:14:13

And that's what I did. I read about computers and networking and computer repair whenever I could get my hands on. I read and I read and I read, and eventually I saved up enough money to buy my own computer. And one of the first things I did, I tore it all apart. That's right. I tore it down to nothing because I wanted to know how it worked and how to put it back together.

00:09:14:14 - 00:09:33:01

And if I ran into a problem, I just referred back to the book. Somewhere inside one of those books was the answer. You just had to find it. Then the internet came along and suddenly I didn't need the book anymore. I could google the problem, and for a long time in technology, one of the most valuable skills you could have was knowing how to search.

00:09:33:09 - 00:09:54:26

Knowing how to Google. Seriously, if you knew how to Google something properly, you could solve problems that made you look way smarter than you actually were. I think they call that fake it to make it. But the important thing wasn't necessarily having every answer in your head, it was knowing where to find the answer. Kind of still is, right?

00:09:54:28 - 00:10:14:15

Then YouTube came along, and now I didn't even have to read some of these explanation. Someone could literally show me books, search engines, YouTubes all different bridges, but all of them were getting me closer to the thing I actually wanted. I didn't really want the book. I didn't really want Google. I didn't really want YouTube. I wanted the solution.

00:10:14:17 - 00:10:45:01

And now something different. Very different is happening. AI doesn't just help me find the solution anymore. Increasingly, I give it the problem. And that's a very, very different thing. The other day I had an issue with the user account. And, you know, this was a tough one, and it really meant that I had to go dig through thousands and thousands of logs and log, you know, each one of those logs had lines of, you know, log files in them.

00:10:45:01 - 00:11:05:29

And I started doing what I've done my entire career. I open the file log, I started searching, started reading through it, I started digging, I was looking for a literal needle in a haystack. And then I stopped and thought, what the hell am I doing? I uploaded the log to I. I basically came back and said, that's a pretty huge file.

00:11:05:29 - 00:11:24:21

And I said, no shit. That's why I'm giving it to you. Find it. And a couple of minutes later it had found the problem. That moment stuck with me because something had changed. I wasn't searching a manual. I wasn't googling the error message. I wasn't watching somebody else's tutorial. I wasn't really operating a tool in the traditional sense.

00:11:24:21 - 00:11:50:03

I was describing the outcome that I needed, and intelligence was figuring out how to get me there. That's a massive change, because for my entire career, software has been basically a toolbox. You accomplish this useless application. You want to accomplish this, you use this application, you have Photoshop, Excel, whatever. Every piece of software has buttons, menus, training, licenses, subscriptions, limitations.

00:11:50:03 - 00:12:12:14

And usually it does maybe 80% of what you actually need. And then for the other 20%, you're still doing it manually, or you buy another tool for the other 20%, then another. Then you figure out a way to integrate them or use them in your workflow. Then you pay somebody to support them. Then someday they raise the subscription price and you keep paying it because you need the software.

00:12:12:17 - 00:12:39:08

What else are you going to do? That's been the model for decades. But now I keep coming back to Sears. The catalog wasn't the business. The catalog was the interface. So what if the application isn't the business either? What if the application is just the interface? And what happens when the interface stops being necessary? Now, I'm not saying we're there today with AI.

00:12:39:09 - 00:13:12:29

We're not. I screws things up. It misunderstands you. It produces garbage. It writes bad code. Sometimes you have to explain what you want. Five different ways to Sunday. Sometimes it's incredibly frustrating. But here's the thing I'm not particularly interested in what I can do today. I'm interested in understanding the direction because I've watched this movie before. Technology gets a little better than cheaper than, faster than, easier than good enough, and eventually something that looked completely permanent starts looking ridiculous.

00:13:13:01 - 00:13:38:12

Imagine trying to explain Spotify to somebody surrounded by cassette tapes. Yeah, there's basically every song ever made. You can instantly listen to whichever one you want on this tiny computer you carry everywhere. That would have sounded insane. Imagine going into Kodak in 1975 and saying the billions of human beings will eventually carry high resolution digital cameras in their pockets.

00:13:38:14 - 00:14:01:03

They take unlimited photographs at a time, instantly send them across the planet, store thousands of them, and almost never print one. Imagine telling Sears that somebody was going to take almost their exact model, put the catalog on a computer network, and build one of the largest companies on Earth. That would have sounded crazy, too, because at the time, most of the pieces weren't visible.

00:14:01:03 - 00:14:35:08

And I think that's what makes right now different. Look around. The pieces are visible. Artificial intelligence. Humanoid robots. Autonomous vehicles. Reusable rockets. Satellite internet. I generated software, images. Music, video. Increasingly cheap computation machines becoming capable of navigating and interacting with the physical world. We don't know where all of this lands. I certainly don't. And anybody that tells you that they know exactly what the world likes and in 20 years is full of shit.

00:14:35:11 - 00:15:00:20

That's not what I'm trying to do. I'm talking about something different direction. Maybe we can look at the pieces we already have and ask some basic questions. What's becoming cheaper? What's becoming easier? What's becoming abundant? What's becoming unnecessary? And then the question I think maybe more important than all the others is what remains scarce because there's extreme value in scarcity.

00:15:00:22 - 00:15:24:11

And if we can follow those changes, maybe we can identify some of the bridges around us before they collapse. Maybe we can recognize when a company or a career, or an entire industry is getting paid to solve a problem that might not exist much longer. Because sometimes companies don't fail because their product sucks. Sometimes the product is great, sometimes customers love it, and sometimes everybody knows the company.

00:15:24:18 - 00:15:46:28

Sometimes they're making billions of dollars and everything looks perfectly fine. And then someone finds a better way to satisfy the same human need. That's what happened to Kodak. People didn't stop taking pictures. That's what happened to blockbuster. People didn't stop watching movies. That's what happened to AOL. We're more connected than humanity has ever been before. That's what happened to Sears.

00:15:46:28 - 00:16:10:17

We buy more things from from home than Sears could have ever imagined. The human desire survived. The mechanism change, the bridge changed. And that's what this show is about. The bridge. I'm going to question things around us that feel permanent. Not because I know they're disappearing, because I don't. I may be completely wrong about some of them, and I probably will be.

00:16:10:18 - 00:16:34:19

But I want to ask, what human need does this actually satisfy? Will that need exist 20 years from now? And if it does, will we still need this particular company? This technology, this career, this product or this business model is satisfied and then the question that gives the whole thing its name. If we're standing on a bridge, where does it lead?

00:16:34:22 - 00:17:06:23

Is it taking us somewhere or nowhere? And the first bridge I want to walk out on to is the one that I've spent most of my life standing on. Technology, in this case, software subscriptions, applications, SaaS, all of these tools businesses pay enormous amount of money to use every year, and right now, almost every software company on earth seems to be doing the exact same thing adding AI, adding copilots assistants, AI agents, AI inside the application.

00:17:06:26 - 00:17:33:26

And maybe that's exactly the right move. Maybe integrating AI saves them, but Kodak had digital cameras. Sears had the catalog. So I can't stop asking one question what if I isn't a feature software companies need inside their applications? What if I changes whether we need the application at all?

00:17:33:28 - 00:17:38:13

I don't know where this bridge ends, but I think it's worth finding out.

THE BRIDGE IN THIS MEMO

The need.
The mechanism.
What comes next.

An editorial reading guide to the original recording.

Human need
Meet a human need.
Current solution
Companies and technologies that feel permanent.
The bridge
The mechanism changes while the need remains.
Better / next solution
A better way of meeting the same need.
PRIMARY MATERIAL

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THE HUMAN TRAIL

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AFTER PUBLICATION

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NEXT MEMO · 002

Why AI Could Make Apps Disappear