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.
In today’s email:
If your data analyst is sweating and your creative director is smiling, Ross Simmonds says you’re doing marketing right
How (and why) Gong's head of content flipped the SaaS marketing playbook
Job: Ross Simmonds is a digital marketing strategist, entrepreneur, and founder of Foundation Marketing, best known for helping B2B brands create and distribute content that drives growth.
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.
Fun fact: He once rappelled down a 20-story building in slacks and dress shoes.
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 humanswho 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 3: "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.
|Make Yourself a Master
We know you’re an expert on something
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Do you also love the idea of making money while sitting in your favorite chair?
Then it’s time to launch your very own pod. Take our step-by-step launch plan and become one of the guinea pigs that make us look good.
In a year or two, when you’re talking about your podcast on another podcast with someone you once called your hero, you’ll probably think about us — doing you a solid right now, and probably publishing a case study about you later.
🤸 A former salesperson turned head of content at Gong shares how flipping the SaaS marketing playbook — by creating demand instead of just capturing it — became their unfair advantage.
📈 With Black creators often left to navigate the creator economy alone, we asked experts Ross Simmonds and Natasha Pierre for their advice on overcoming challenges and achieving meaningful growth.
✍🏾 With video and podcasts on the rise, we asked 10 marketing experts from SEO to YouTube whether blogging is really on its way out, or just evolving.
Want a free live session with Jay Schwedelson?
Masters in Marketing is teaming up with Guru Media HUB to bring you our first free live session. Join Jay Schwedelson, founder of Guru Media and Subjectline.com, for a tactical conversation on what actually works in email marketing — and what doesn’t. Expect tips, tricks, and conversion-boosting strategies you can put into practice immediately.
|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: 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?
This week's email was brought to you by Caroline Forsey. Editing by Laura M. Browning and Curt del Principe.
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