Volodymyr vs Vladimir: The 1st Native Analog vs Native Digital War (And What It Means For Every CEO)

Christopher Lochhead
7 min readMar 22, 2022

The analog world used to determine what happened in the digital world. Now, the two have flipped.

(By Category Pirates 🏴‍☠️)

Part I

Over the past year, we have written extensively about the bifurcation between Native Analogs & Native Digitals.

Native Analogs are Baby Boomers and Gen Xers born anywhere from the 1940s all the way up to the early ’80s. Today, they range between the ages of 40 to 75, and make up approximately 136.8 million Americans.

Native Digitals are Millennials, Gen Zers, and beyond, born between the early 1980s to as recently as the 2010s. These demographics are around 35 years of age on the high end, down to as young as 6 years old, and make up approximately 140.1 million Americans.

Much has been written in the past 20 years about “Digital Natives,” but this is a loose understanding of the chasm between these two demographics. When we say “Native Analogs” and “Native Digitals,” we are not talking about age.

We are talking about identity.

“Native Digital” is not a mindset. It does not mean “some people embrace technology while others do not.” It also doesn’t mean if you’re old, you’ll never “get it.” We created the terms Native Analog and Native Digital to introduce shared language that would allow society to discuss the differences between people whose primary life experience is Analog-first (in the real world) from people whose primary life experience is Digital-first (online). For example: Pirate Eddie and Pirate Christopher cannot, and will never be “Native Digital,” even though they have worked with technology for over 30 years. And the reason isn’t because they “don’t get it” or refuse to embrace the digital world. “Learned Digital” is possibly a middle ground. But they will never be Native Digitals because their primary life experience still takes place in the real world. Their identity is still rooted offline.

Pirate Cole (a Millennial), on the other hand, is the opposite.

Between the 3 of us, we see these differences in our interactions constantly. And without the language of Native Analogs & Native Digitals, we may have fallen into the same trap corporate workplaces, organized education systems, and even the media fall into every single day: misunderstanding each other, judging each other, and failing to appreciate each other’s primary life experience.

For example, every Friday we get together digitally to create and write Category Pirates together. When we asked ourselves, as a group, “What do we call our Friday sessions?” the two Native Analogs called it “a Zoom call” and the Native Digital called it “a face-to-face meeting.” This is not an accident. If you are a Native Analog, you see the digital world as an addition, extension, or even distraction to your analog life.

If you are a Native Digital, you see the digital world as your primary life, and the analog world as an addition, extension, or even distraction from your digital life.

Again, this is not an Old vs Young issue.

This is a first-time-ever-in-human-history phenomenon: Native Analogs are the last of a dying breed, and Native Digitals are a new category of human.

And from here on out, there will never be another Native Analog generation born ever again.

Think about that.

Part II
Native Digitals grew up integrated with the digital world.

They had smartphones before they had college degrees, high school diplomas, or (for Gen Zers) a bicycle to ride around the neighborhood. (“Bicycle? Why? All my friends are online.”) They grew up integrated with the cloud. They don’t know what it’s like to not have the answer to any and every question in their pocket, two taps and a swipe away. The digital world is where they primarily live.

(And when parents restrict their screen time, whether they realize it or not, they are removing them from their primary lives and threatening their core life experience.)

The Native Analog & Native Digital lens is fascinating in and of itself, but it gets more powerful when changes in the world are viewed and understood through it.

For example:

Nowhere in the media have we seen anyone discuss the Russia/Ukraine war through the Native Analog & Native Digital lens.

And we think this is a giant misunderstanding of what’s happening — and why Ukraine (unlike so many other war-torn countries) have rallied the globe and received more than $13.6 billion in aid from the United States alone.

Most people think this support for Ukraine “just happened” (the same way most business media think demand for a given business just “happens,” like the weather). It did not. The support was created — in exactly the same way Category Designers create net-new demand out of thin air.

Europe’s population is approximately 747.7 million people — with the most common age being 34. Think about this. (Then think about it again!) Native Digitals get their information in the digital world. In addition, they most value information from others in the digital world and they mistrust most analog media like CNN, Fox News, or The BBC. And now only 41% of Americans trust traditional media to report the news “fully, accurately, and fairly”.

Ukraine’s president, Volodymyr Zelenskyy is a former actor and comedian, and a master digital communicator. If President Barack Obama was the first president to use digital methods of reach like Facebook advertising, and President Donald Trump was the first president to push digital methods of reach (like Facebook advertising and Twitter) into the mainstream media, then President Volodymyr Zelenskyy is the first war-time president to leverage digital methods of reach (like posting selfie videos on Twitter and Instagram) to bring digital air cover to an analog war. In addition, he has empowered his nation to share the horrors of the analog killing in Ukraine on digital platforms, which further amplifies these analog atrocities in an environment where they scale like never before. Where images of a pregnant mother being evacuated from a bombed hospital can be seen by hundreds of millions of people in real time.

As a result, Volodymyr’s digital dominance has led to historic pressure being put on governments and corporations to inflict more economic pain on Russia than has ever been levied on any country, ever. It used to be that what happened in the analog world dictated what happened in the digital world — but now, the two have flipped (and most people don’t see this radical transformation happening in plain sight). Digital stories, digital messages, digital photos, digital conversations, and the subsequent digital movement in support for Ukraine that has had catastrophic consequences for Russia in the analog world.

And whether Volodymyr, Vladimir, or the rest of the world consciously realizes it, we are observing humanity’s first Native Analog (Russia) vs Native Digital (Ukraine) war.

Volodymyr is rallying the entire digital world, which is having a direct impact on their analog ability to fight the war. He is inspiring U.S. voters to influence politicians, but also U.S. consumers to influence U.S. CEOs. Make no mistake that while the sanctions are hard-hitting, cutting everyday consumers off from the global economy is more immediate and visceral.

It can’t be stressed enough that digital actions are driving analog results.

No government made the countless number of major corporations stop doing business in Russia. Nike, Coke, McDonalds, Apple (and dozens of other major companies) made the choice because of the massive roar of digital voices surrounding them.

Voices that would be almost impossible to hear, at the same speed and scale, in the analog world. (Even ExxonMobil doesn’t want to be on the wrong side of history.)

Meanwhile, Vladimir is banning troops, government officials, and Russian civilians from posting anything in the digital world — which means he is (unknowingly) surrendering the digital war. By all accounts, he is extremely paranoid of the analog risks of COVID or a potential coup around him, but may not see the blowback coming from taking away smartphones from soldiers.

Part III

Goldman Sachs CEO, David Solomon (Native Analog), recently mandated that his employees return to the office.

Only 50% of them did.

Until Native Analog leaders understand that Native Digitals are a new category of human, with a 180-degree difference in the way they experience life and world, they will not understand one of the biggest changes in the development of our species.

And their ability to successfully lead will diminish at ever-accelerating rates.

Vladimir Putin is fighting an analog-only war.

Volodymyr Zelenskyy is fighting an analog AND digital war.

(That’s a big part of why Volodymyr is winning.)

And this is exactly what’s happening in the business world today.
Apply the Native Analog & Native Digital lens to business, and what you’ll see is that almost every company run by Native Analogs will not be able to successfully recruit, retain, or market to Native Digitals — unless they change. Because they don’t understand that this is not an age conversation, it’s an identity crisis. It’s two different categories of humans yelling at each other, arguing over which reality is the “real” one.

We believe that the inability to see this obvious change to a new category of human will be the cause of more CEO firings

and more market cap (aka value) destruction in the next ten years than ever before in history.

As more and more companies run by Native Analogs fail to embrace this new reality, more and more new categories of startups and innovations will displace the analog old with the digital new. This might be the biggest threat and biggest opportunity of this generation.

If you’re a CEO, you must lead this change (Volodymyr).

Otherwise, you will become Vladimir — 100% reliant upon analog brute force, with the entire digital world against you.

Category Pirates 🏴‍☠️

Nicolas Cole

Eddie Yoon

Christopher Lochhead

PS: If you don’t believe this is the first Native Analog vs Native Digital war, consider where we would be if Ukraine’s president, Volodymyr Zelenskyy, had made a similar choice as Putin to shut down all digital communications. Imagine if he too had banned people in Ukraine from sharing what was happening on social media. Imagine if he, himself, had chosen not to take to social media, speak directly into the camera, and address the digital world directly. Would the world be as invested in Ukraine? Would the U.S. have sent billions in aid? Would global companies have pulled out of Russia?

Not a chance. 🏴‍☠️



Christopher Lochhead

13X #1 Bestseller | Snow Leopard | Play Bigger | Niche Down | Podcaster | Investor/Advisor