Riding Technology Waves | Stay SaaSy

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22 Jun 2026

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strategy

Technology businesses are heavily influenced by waves of technology change, like the rise of the internet or AI. Knowing how to adjust strategy for these changes is one of the most important skills to develop.

As technology has advanced, technology waves have become larger, more frequent, and more sudden. In just the last 30 years (less than a full career, literally less than the time between graduation and your first 401k payout) we’ve seen:

The rise of the consumer internet, creating massive companies like Google, Amazon, Meta and Netflix, and essentially killing dozens of industries from print media to Blockbuster videos.

The rise of cloud (enterprise internet), which was an extinction event for on-prem B2B software that companies like Adobe, Bloomberg, and Microsoft managed to survive.

The rise of mobile, creating massive companies like Uber and Instagram, turbo-charging companies like Apple and Meta, temporarily shoving Microsoft into a corner, and reshaping where we spend our attention.

Aborted technology waves for 3D printing and Virtual / Augmented reality.

The “rise” of crypto / Web3, creating a large public company (Coinbase) and a large illicit marketplace (The Silk Road) and some stablecoin infrastructure, but few other major businesses or use-cases. More on this later.

The rise of AI, creating lightning fast growth for OpenAI, Anthropic, and Cursor, turbocharging Nvidia and AMD, and shaking essentially all industries to their core.

This has happened for thousands of years. I’m sure there was some Bronze Age metalsmith in 3000 BC who had to explain to his pissed-off wife that he lost his job because some asshole figured out you could make a better sword out of iron. Disruption from technology waves has been happening for thousands of years and will continue for the indefinite future.

What To Do

I’ve been around long enough to watch multiple technology waves swell and break on the shore. There are a few super simple questions below that I ask as early as possible in a technology wave that I’ve found invaluable for orientation. The key is to ask them, in order, every time:

Does this technology actually matter? Does anyone that I know actually use it? Is anyone changing their habits because of it? If it’s a new speculative technology (e.g. internet, AI, blockchain) does it like, actually do something anyone cares about?

If it matters, you need to ask how the new technology actually functions . Could I explain it to my mom at a very high level if I had to? Talking points from social media or (worse) traditional media don’t count.

Once you know how new technology works, you need to ask what new functions it will enable . Since we’ve established that it matters and understand how it works, what behaviors will it change? You’re looking for ground truths about the future, even if they’re obvious: AI lets people create images faster, AI lets you synthesize huge amounts of text, AI generates working code. Establish the facts in a boring way; inoculate yourself from hype and grifters. For mobile, instead of “all of the internet, directly in your pocket,” go with “it will be possible to perform business tasks in places with broadband, as long as they work on a small touchscreen.”

Finally, you have to ask whether your product or business is impacted . Do buyers care about any of the things that the new technology does? Does it impact your cost structure? Does it impact your customers’ businesses? If you gave yourself a cold enough shower at the previous step, you’ll be left with the distilled reality of whether this wave matters for your business.

These questions are not hard to answer. They do not require a deep math background or Machiavellian cleverness. If this is a road trip, you’re not trying to find a shortcut through backroads, you’re just trying to figure out if the bridge you’re about to drive over has collapsed. But it is essential that you actually take the time to ask them, which is surprisingly hard because…

People Are Lazy

Whenever a new technology wave comes along (like the internet, mobile, or AI), a huge number of businesses simply ignore it because change is annoying. Maybe if we ignore these dumb phones they’ll go away. This GPT thing can’t count how many Rs are in the word “strawberry,” it’s useless.

(Worth noting that the tendency to ignore new technology waves seems to have gone down over time. There were many, many more internet skeptics than AI skeptics)

Ignoring new technology waves feels good because most technology waves do sputter out. The few big businesses built on crypto have (so far) been mainly related to speculating or buying drugs. VR games never got mainstream adoption. Only weirdos and tinkerers have 3D printers in their homes. Being lazy pays off pretty often. It also lets you talk down to others, which many people unfortunately enjoy.

Additionally, just...