Boring Marketing Is Your Biggest Competitor in the AI Era with Jay Schwedelson

If your marketing blends in, it’s already losing. In this episode, Mike Montague sits down with @schwedelson , CEO of Outcome Media, founder of SubjectLine.com, and host of the Do This, Not That podcast, to talk about why “boring” is the silent killer of your campaigns. Jay shares why AI isn’t the enemy, but a partner for amplifying creativity, and how SMBs can use it to produce attention-grabbing ideas that cut through the tidal wave of generic content.

From meme-powered event promotions that generated millions of organic views, to practical tips on balancing “feed the beast” consistency with big creative swings, Jay gives a masterclass in marketing that stands out without burning you out. You’ll hear how to avoid the trap of overcomplication, why focusing on simple, human ideas works, and how to create moments that make your audience stop scrolling and start engaging.

Key Takeaways

1. Boring is the real competition – In a crowded market, blending in is more dangerous than making mistakes; safe content gets ignored.

2. AI is your partner, not your replacement – Use AI as an editor, idea generator, and assistant, not as a content factory that strips away your humanity.

3. The tidal wave of generic content is an opportunity – The more AI slop out there, the easier it is for authentic, human-centered marketing to stand out.

4. Niche down to the basics – Most people don’t need cutting-edge tactics; simple, easy-to-implement ideas resonate with a far wider audience.

5. Make your own GPT – Training a private GPT on your own content and voice can unlock faster idea generation and better alignment with your brand.

6. Create “firehose moments” – Big attention spikes from events, stunts, or campaigns are essential for staying top-of-mind throughout the year.

7. Feed the beast consistently – Maintain baseline activity on key channels so your brand never sends a “we’re out of business” signal.

8. Mix quantity with creativity – Send more emails, post more often, but focus on good-enough consistency while saving energy for bold, high-impact ideas.

9. Leverage cultural formats like memes – Repurposing familiar templates with your message can spark massive organic reach for very little cost.

10. Simplify your focus – Limit email checking, avoid constant reaction to “noise,” and go deep on the channels and formats you actually enjoy.