Naysayers and History: It Doesn’t End Well

This piece originally appeared in my newsletter , the Operating Partner. As you may have noticed, I do not post all OP content to LinkedIn. To subscribe to the OP for free, click here .

I recently spoke with an enterprise sales rep from an AI company that’s developed a competitor to Canva and Adobe. They’re out there hunting for new clients and found their way to me through a colleague. Their goal is to sell to brands and ad agencies, but they haven’t quite nailed down the path of least resistance—or the path to the greatest opportunity.

The sales rep mentioned two common reasons agencies have been lukewarm about their pitch:

1. They believe AI-generated content isn’t as good as what their Chief Creative Officer can produce.
2. They worry that AI could disintermediate the agency layer, making them less relevant.

I’ve spent years working with B2B marketing technologies, helping them shape their go-to-market (GTM) strategies, and history tends to repeat itself: those who resist change are often irrelevant within 5-10 years.

Let me walk you through three examples from the marketing (and ad) technology space.

1990s: The ‘90s brought us the digital age, with the first advertising opportunities on the web—banners. Some of the original banner creators are OP newsletter subscribers and close friends of mine. At the time, many in traditional agencies dismissed banners. Smaller digital agencies emerged, gaining traction not just with banners, but also co-registration, affiliate marketing, email, and eventually, the fast-growing search engine business. These "small" digital agencies grew into giants, challenging—and in many cases replacing—traditional agencies that couldn’t adapt.

2010s: The debate between broadcast vs. digital video was fierce in the late 2000s and early 2010s. Digital video platforms—YouTube, Roku, Amazon, TikTok—couldn’t be ignored. These platforms became major players, dominating traditional broadcast channels. Many agencies clung to their broadcast business, failing to innovate in time. They soon found themselves scrambling to catch up—or worse, filing for bankruptcy—after audiences migrated to digital platforms. While hindsight makes this shift seem obvious, it was highly contentious at the time and far from a clear-cut decision.

Today: To AI or not to AI—that’s the question. Is AI on the right side of history or the wrong side? For me, the answer is clear: it’s on the right side. I believe AI will lead to creative efficiencies and effectiveness we’ve never seen before. But it comes with costs, and we must watch and govern for them. If agencies and brands don’t adopt AI, what’s the ultimate price? I think it will be steep. Agencies must continuously reinvent themselves. A friend of mine, Rishad, once described agencies as the “ultimate cockroaches” —they survive by adapting.

Most humans love stasis. We don’t love change. I do not always like change. But those who embrace change are often the ones who get out of the gate first and have the potential to stay ahead. If you’re in marketing and resisting AI, I believe you’re positioning yourself on the wrong side of history. And as history has shown us, it tends to repeat itself.