Kieran Flanagan

Things Kieran Says on Podcasts

SVP Marketing @HubSpot, podcast host, investor, advisor

Where to Find Them

Kieran Flanagan hosts Marketing Against The Grain , writes Kieran’s Substack - The AI Marketing Generalist , writes a16z Podcast and hosts The GaryVee Audio Experience . They have also been a guest on MarTech Podcast ™ // Marketing + Technology = Business Growth (7 times) , The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch (3 times) , The Dave Gerhardt Show (from Exit Five) (2 times) , Lenny's Podcast: Product | Career | Growth , My First Million , Ahrefs Podcast and Everyday MBA .

Recently: “We’ve Spent 20+ Years in Marketing. Here’s What We Learned” on Marketing Against The Grain (October 2026); “How a Top AI Expert Actually Uses Claude” on Marketing Against The Grain (October 2026); “How Marketers Can Make $20K/Month With Tiny Apps” on Marketing Against The Grain (October 2026); “Your next marketing hire should probably surprise you” on Kieran’s Substack - The AI Marketing Generalist (October 2026); “The Marketing Teams Of 2027 Will Look VERY Different...” on Marketing Against The Grain (October 2026); “Marketing Experts Turn GrokBot Into an AI Content Team” on Marketing Against The Grain (October 2026).

What They Said

“One of the things that I continue to tell the young generation of marketers today, who are going to, for the most part, not have a world where they did not have AI to help them do a bunch of work, is please, please, please do not forget how to write. I'm starting to come to the conclusion that the best way to grow an audience and to create great content is to use no AI at all.” — Kieran Flanagan, Marketing Against The Grain

Kieran and Kipp were discussing a classic direct-mail copywriting book and how much of marketing rests on psychology and writing. Kieran turns to the effect of AI on marketers, and goes on to say he is avoiding it even for research.

Marketing Against The Grain · 2026-10-29 Permalink → Listen →
Marketing Against The Grain Around 05:22 into the episode
Kieran Flanagan

…they should do. And he says, Tell people you're going bankrupt and you have a great deal because of it. And it saved the business. And so, that's the opposite example of like where you're like overtly to the point and truthful. Like, we're going bankrupt unless we sell all this stuff at a discount.

Kipp Bodnar

…have a really great deal for you. And we care about our customers, even though we're going bankrupt. It's the perspective and the framing of the truth that we're actually talking about, right? And I think in a lot of the books that we have been reading, I think that's a common thread across them.

Kieran Flanagan

Yeah. Yeah. You know, it's kind of interesting how much of marketing is anchored in human psychology and writing. Yes. And one of the things that I continue to tell the kind of young generation of marketers today who are going to, for the most part, not have a world where they did not have AI to help them do a bunch of work is please, please, please do not forget how to write. I'm starting to come to the conclusion that like the best way to grow an audience and to create great content is to use no AI at all. Not even for ideation, not even for

Kipp Bodnar

the other end, folks. I'm going to go back, baby.

Kieran Flanagan

Now, research, but even research. You know, research, because everyone ends up in the same spot, right? You prompt AI differently, you ask it different things, but for the most part, you're probably going to get similar ideas as everyone else, similar research as everyone else. So I think the way I…

Kipp Bodnar

That's a clothing brand. That is like the Aussie surfing clothing brand. That's a fun one. I had a

Speaker names come from our own diarization. The position is estimated from where the line sits in the episode.

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