- The Marketing Factor
- Posts
- Why this marketing moment feels like early 2000s
Why this marketing moment feels like early 2000s
The AI era is wild but Wil Reynolds, founder of Seer Interactive, has seen something like this before. Here’s what we can learn.
Austin Dandridge
August 05, 2025
I just dropped a conversation with Wil Reynolds (founder of Seer Interactive) that I think you'll find fascinating, especially if you're feeling the ground shifting under your feet in marketing right now.
Listen here: Spotify, Apple Podcasts, YouTube
Will compared this moment in marketing to the early 2000s SEO days: "Super fast. No one knows what they're doing." But instead of being intimidated by that, he's energized by it and his energy is infectious.
He’s been a thought leader in the marketing space for a long time, and I had been clamoring to have him on - lighting up his inbox, and he graciously accepted.
Just a few of the things we covered, it’s really worth 30 minutes of your time.
The brutal truth about team dynamics right now: Wil had to tell his team, "This is not the company for you if you want certainty." He's pushing people who can't adapt to innovation seasons – because in a tough job market, people won't quit on their own, but companies can't afford to carry dead weight.
Why content volume doesn't matter anymore: He had a pretty killer Nudie Jeans vs. Banana Republic example he shared. Basically, in traditional search, Banana Republic could throw some text on their site about being "environmentally friendly" and rank. But LLMs understand that environmental clothing means water usage, fair wages, dye processes – so Nudie ended up showing in the LLM above BR. Basically, you can't fake operational transparency anymore.
His personal AI workflow: Wil records detailed notes about every hotel experience, then feeds them to ChatGPT. When planning trips, instead of getting generic "top 10 places" recommendations, he gets suggestions based on his actual preferences with his exact quotes referenced. It's brilliant.
The whole conversation just felt like a masterclass in thriving during uncertainty rather than just surviving it.
Listen here: Spotify, Apple Podcasts, YouTube
I especially liked the part where he breaks down his Claude MCP setup that connects email, calendar, BigQuery, and call transcripts into one workflow. I went ahead and built out my own and wrote a post about it here.
Let me know what resonates with you after you listen.
P.S. You’re receiving this email because you’re a friend or supporter of Cobble Hill. If you no longer wish to receive these, no worries - just unsubscribe. If you know someone who would benefit from this content, I’d appreciate it if you’d share it with them!
If you’re new, here’s how you can follow along with my weekly podcast:
