If you’ve ever stared down a sea of bland AI content and whispered, “Is this my job now?”, you’ll enjoy this master’s take: “The amount of blog posts that are written with AI is at an all-time high… And all of it is trash.”

Ross Simmonds joins us with some spicy takes on experimentation, distribution, and AI. And I promise: It’s not trash.

Ross Simmonds 

Founder, Foundation Marketing; Digital marketing strategist, entrepreneur

• Fun fact: He once rappelled down a 20-story building in slacks and dress shoes.
• Claim to fame: Simmonds has done something most marketers would be afraid to even attempt — he’s made the front page of Reddit six times over the last few years, and has helped clients do the same.

Lesson 1: Dedicate 20% of your budget and time to experimentation.

Here’s the thing about marketing teams: We love a good spreadsheet, a strong quarterly plan, and the warm, fuzzy feeling of “proven tactics.” But Ross Simmonds wants you to spice things up. 

Don’t worry, we’re not talking about going completely unhinged. “Eighty percent of your work should be low- to mid-risk, but carve out 20% for the stuff your competitors are too scared to try,” Simmonds tells me. 

In other words, treat experimentation like guac at Chipotle: It costs a little extra, but it’s worth it. 

Simmonds suggests allocating time on your team’s calendar for experimentation in the same way you’d block off a week in the Caribbean.

One way to do this is an “experiment week,” in which everybody experiments with a different channel for a few hours each day — TikTok, Reddit, you name it. The teams then present to the larger org, and everyone votes on one winning idea.

If it makes your bowtie-wearing, type-A data analyst uncomfortable and your creative director thrilled, you’re on the right track. 

This lesson is mainly about not falling into the safe zone. Pushing the boundaries and playing bold is the only way to stand out.

Lesson 2: Let AI nurture your leads while you sleep.

I would never waste your time by blabbering on about how AI helps create scalable content. 

That lesson has been hammered into the ground already. But Simmonds offers a sharper, more human take: The real winners will be the brands that empower their marketers to create content that’s insightful, data-driven, emotional, and uplifting.

“Content that gives hope and inspires people — that will win amidst the mediocrity we’re going to see across the internet,” Simmonds says.

So, where does that leave AI? Squarely in the lead-gen space. 

“The most value in B2B that we’ve ever seen will be unlocked when we allow humans to create ridiculously valuable content, and then allow AI to study the other humans who are connecting with these stories and nurture those relationships at-scale. And then AI can bring those two humans back together to do business.”

Simmonds sees a world where, using tools like HubSpot (yep, shameless plug), Clearbit, or Koala, AI could help “unmask” anonymous visitors by figuring out where they work or who they might be. Once it knows that, it could automatically reach out to them — like sending an email or a LinkedIn message — with something that feels personal and relevant.

“And when those things happen while everybody’s sleeping,” Simmonds says with a smile, “It’s going to be fascinating.”

Lesson 1: “Create once, distribute forever”.

Simmonds is infamous for coining the marketing phrase “create once, distribute forever.” 

(As an aside, I’d love to know how to become famous for coining something. I have ideas. “Procrastibaking,” for one.) 

This phrase essentially means that too many marketers spend hours creating content, and little-to-no time or energy promoting it. Which, Simmonds argues, is the wrong approach. 

He suggests marketers should be spending way more time getting that valuable content in front of the right audiences — and repurposing or reposting as they see fit. 

For B2B marketers, Simmonds says LinkedIn is your go-to channel for distribution.

But his suggestion for B2C is a little different: “On a B2C lens, you can connect and scale on TikTok in a ridiculously effective way. And the content you distribute through TikTok is actually highly re-purposeable across every channel: YouTube Shorts, X, Instagram Reels. You’ve set yourself up for success because your content can be spread across all of these different channels.”

If you’re “creating once, distributing forever,” this could look like spending five hours creating and editing a TikTok — and 15 hours over the next few months distributing it on TikTok, and across other video-hosting platforms. 

Because people aren’t sitting around impatiently awaiting your next piece of content to launch. They’re busy and overstimulated. It might just take 15 hours for you to finally get in front of them.

Lingering Questions

THIS WEEK’S QUESTION

You always say ‘create once, distribute forever’ — what’s one piece of content you’ve milked longer than anyone should reasonably admit? And why that one? —Jay Schwedelson, Founder, SubjectLine.com; Host, Try This, Not That! For Marketers Only!

THIS WEEK’S ANSWER

Simmonds says: One piece of content I’ve absolutely milked? A tweet I wrote in 2019 simply said “Create Once, Distribute Forever,” and it was a hit. It wasn’t even meant to be a flagship idea back then — just a brain dump about repurposing strategy. 

But I kept referencing it in talks, turning it into a slide, a workshop, a tweet thread, the title of my book, and eventually the cornerstone of how we approach content at Foundation.

Why that one? Because the concept resonated deeply not just with marketers, but with entrepreneurs, creators, and executives who realized they were sitting on gold without mining it. It gave people permission to stop chasing new and start maximizing what they already had. 

That message stuck, and I’ve been doubling down ever since.

NEXT WEEK’S QUESTION

Simmonds asks: What’s one marketing hill you’ll die on… Even if the data or the trends say otherwise?