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HomeUncategorizedFrom Mad Men to Machine Learning: What Kevin Lee Taught Me About...

From Mad Men to Machine Learning: What Kevin Lee Taught Me About the Future of Marketing

By Jeffrey Hayzlett

I’ve been around marketing long enough to remember when deals were closed over long lunches, handshakes mattered, and buying media was more art than science. That’s why I always pay attention to people who’ve seen every version of this business and still manage to stay ahead of it.

That’s exactly why I invited Kevin Lee, Executive Chairman and Co-Founder of Didit, onto All Business.

Kevin has been in the trenches since the earliest days of digital marketing, before Google, before SEO was a buzzword, before anyone knew what programmatic buying meant. And what struck me most in our conversation wasn’t nostalgia. It was clarity.

Because while the tools keep changing, the fundamentals of smart marketing and responsible leadership haven’t.

The Biggest Shift: Marketing Became a Trading Floor

Kevin put it plainly: media buying has gone from Mad Men to machines. What used to be negotiated over a three-martini lunch is now bought programmatically — more like securities trading than advertising.

That shift changed everything. The old rules of “buy more, pay less” disappeared. Today, the more you buy, the more expensive it can get at the margins. Decisions are made in milliseconds, by algorithms, not relationships.

And here’s the key takeaway for executives: you’re not buying volume anymore, you’re buying precision. You’re buying moments, signals, intent. Whether it’s search, social, display, or CTV, it’s all programmatic now.

And that doesn’t make marketing easier. It makes leadership more important.

Search Isn’t Dead but It’s Not in Charge Anymore

Kevin built Didit on search marketing before most people even understood what it was, back when AltaVista and Lycos ruled the world. The insight then still applies now: when someone raises their hand and says, “I want this,” you better be there.

But today, that hand isn’t always raised in Google.

ChatGPT, Claude, Gemini, AI-driven research is changing how decisions get made. Sometimes there’s no click at all. The answer just shows up, and the buyer moves on.

That’s a wake-up call for brands.

The new game isn’t just ranking links; it’s earning consensus. AI systems don’t just look at one source. They look at many. Mentions, reputation, content quality, credibility. It’s part SEO, part digital PR, part social proof.

If the market isn’t talking about you, the machines won’t either.

Authenticity Wins and Fake Content Loses

We talked plenty about content, and this is where I see leaders getting it wrong.

Yes, AI can generate content at scale. But scale without authenticity is noise. Kevin made it clear: human-created, useful, new content still wins. Regurgitated AI fluff doesn’t.

Executives need to resist the temptation of pushing out more content just because it’s easy.

Content still builds communities. Communities still drive commerce. But only if the content is real, relevant, and trustworthy.

If you’re chasing clicks instead of conviction, don’t be surprised when nothing converts.

Performance vs. Brand: You Need Both

Too many companies swing the pendulum too far.

Performance marketing harvests existing demand. That’s important, especially if you’re new, growing, or fighting competitors (and who isn’t?) But brand marketing is what breaks ties, builds trust, and sustains growth.

Kevin nailed it: if you rely only on performance media, you will hit diminishing returns.

Even brands like Bose have stepped back from pure performance to reinvest in educating the market on why they’re better. That’s not a retreat, it’s strategy.

The smartest leaders know when to harvest demand and when to create it.

Own Your Content or Rent Your Future

This one is non-negotiable for me — brands that don’t own their content don’t own their future. Period.

Your website isn’t the center of the universe anymore; it’s a brochure. Content must live where your audience lives. But ownership still matters, especially as AI becomes the new gatekeeper of visibility.

Consensus doesn’t come from shouting on one platform. It comes from collaborating, syndicating, and showing up consistently across the ecosystem.

If you’re not acting like a publisher, you’re falling behind.

AI Power Requires Executive Responsibility

We also tackled the uncomfortable question: just because we can do something with AI, should we?

With great power comes great responsibility. Marketers influence behavior, opinions, and trust. If the industry doesn’t take that responsibility seriously, government regulation won’t be far behind.

Values matter. Context matters. Where your brand shows up and what it stands next to matters.

This isn’t just a marketing decision. It’s a leadership one.

The Best Advice Kevin Gave Executives

If you want one practical takeaway, it’s this: get an outside audit of your marketing.

Not from people who live in PowerPoint decks but from people in the trenches. Fresh eyes. Real operators. People who understand earned, paid, and that fuzzy middle ground in between.

You don’t have to take every recommendation. But you do need perspective.

Because disruption doesn’t care how smart you think you are.

Final Thought

I always say: adapt, change, or die.

Kevin Lee has adapted through every boom and bust this industry has thrown at him and he’s still building, still experimenting, still pushing forward with purpose.

The lesson for executives is simple: surround yourself with people who challenge you, who think differently, and who aren’t afraid to tell you the truth.

That’s how you stay relevant. That’s how you grow. That’s how you lead.

Watch the full episode on C-Suite TV.

Jeffrey Hayzlett
Jeffrey Hayzletthttp://hayzlett.com/
Jeffrey Hayzlett is a primetime television host of C-Suite with Jeffrey Hayzlett and Executive Perspectives on C-Suite TV, and business podcast host of All Business with Jeffrey Hayzlett on C-Suite Radio. He is a global business celebrity, speaker, best-selling author, and Chairman and CEO of C-Suite Network, home of the world’s most trusted network of C-Suite leaders. Hayzlett is a well-traveled public speaker, former Fortune 100 CMO, and author of four best-selling business books: Think Big, Act Bigger: The Rewards of Being Relentless, Running the Gauntlet, The Mirror Test and The Hero Factor: How Great Leaders Transform Organizations and Create Winning Cultures. Hayzlett is one of the most compelling figures in business today and an inductee into the National Speakers Association’s Speaker Hall of Fame. As a leading business expert, Hayzlett is frequently cited in Forbes, SUCCESS, Mashable, Marketing Week and Chief Executive, among many others. He shares his executive insight and commentary on television networks like Bloomberg, MSNBC, Fox Business, and C-Suite TV. Hayzlett is a former Bloomberg contributing editor and primetime host, and has appeared as a guest celebrity judge on NBC’s Celebrity Apprentice with Donald Trump for three seasons. He is a turnaround architect of the highest order, a maverick marketer and c-suite executive who delivers scalable campaigns, embraces traditional modes of customer engagement, and possesses a remarkable cachet of mentorship, corporate governance, and brand building.
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