Day 5: The Content Upgrade Loop

How Jonathan Goodman generates 500–1,000 leads per month using existing content.

Welcome to Day 5 of the 30 Days of Growth.

This is a pop-up newsletter put together by Chenell from Growth In Reverse. I’ve pulled 30 creators together to help give one short, actionable way you can either grow or improve your email list.

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You can view all past issues of the 30 Days of Growth here.


Most people treat lead magnets like homework.

They agonize over creating the perfect PDF or checklist…then hope it magically drives new subscribers.

Jonathan Goodman knows better.

He generates 500 to 1,000 leads every single month — not by creating new content — but by repackaging what already exists.

Podcast interviews. Guest features. Articles. Even content about his students.

It all becomes fuel for what he calls: The Content Upgrade Loop.

Instead of creating a lead magnet and hoping people care, he uses content that’s already proven to resonate and builds a system around it to capture emails and start conversations.

🔍 How Jonathan Did It:

Jonathan started by auditing his existing content library – looking for anything that solved a specific problem or shared a story his audience cared about.

It didn’t matter whether he created the content or if someone else did (one of his best-performing upgrades is an interview of his student on another podcast).

He built simple landing pages for each piece, often just:

  • A short headline
  • A description of what someone would learn
  • And an email opt-in form

Once someone joined, the content was delivered immediately through email or automated DM tools like ​ManyChat​.

But the magic happened after delivery.

His team followed up personally with a short, human message:

“What are you hoping this helps you with?”

That opened a genuine conversation, not a sales pitch.

💭 Side note: Remember how Jason Resnick did the same thing with his ​4-Hour Email​? Building relationships and asking questions works.

Understanding what the subscriber wanted and guiding them to the right next step.

Over time, Jonathan tested different content topics to see which converted best. Once a winner emerged, he amplified it with paid traffic — sometimes spending $30,000/month sending people to a single podcast interview landing page because the conversion numbers worked that well.

🧠 Why It Works:

There are a number of reason’s this works, but here are a few:

  1. Turns passive content into active conversations: No hard pitch required
  2. He didn’t need to create new assets: Repackage what’s already working and use it to provide value
  3. Context-rich opt-ins: People know exactly what they’re getting
  4. Personal follow-up feels natural: Opens the door for real connection

📊 Results

Jonathan has been doing the content upgrade thing for years, only recently transitioning it to Instagram. But this method has helped him:

  • Build his coaching business to $5-$7 million per year
  • Book 500-1,000 calls a month off of this strategy via ​his Instagram account​

So, I’d say it’s working quite well 🙂

💡 How You Can Implement It

  1. Audit your content library. Look for podcasts, interviews, or articles you’ve already published that solve specific problems. Again, these don’t even have to be pieces of content you’ve created – these can be interviews you’ve done (or your clients have done) on other shows or channels.
  2. Build a simple landing page. Use a clear headline, a short description, and an email opt-in form.
  3. Promote it through social posts. Share regularly on Instagram Stories, LinkedIn, or Twitter to drive traffic.
  4. Deliver the content immediately. Send the resource right away via email or DM so there’s no waiting. Speed is key.
  5. Follow up personally. Ask a quick, low-pressure question like, “What are you hoping this helps with?”
  6. Double down on winners. Run paid traffic to the content upgrades that perform best. Or just keep promoting them on different channels if you don’t want to use paid traffic.

🛠️ Tools

  • ManyChat or similar for automated replies
  • Kit, Beehiiv, or any landing page builder
  • CRM to manage follow-ups and track conversations (or a Google sheet and a Zapier zap can work)

💭 Final Thought

Jonathan didn’t out-create his competition, he out-curated them.

By turning existing content into a conversation starter, he built a repeatable system that drives leads every single day.

See you tomorrow,
Chenell

P.S. What content could you dust off and turn into a lead-generating machine? It’s probably already out there, waiting for you to package it right.

P.P.S. Jonathan writes an incredible newsletter called 5-Reps Friday. The landing page says it’s for “jacked nerds” but I am only one of those things (spoiler: not the first one 🤓), and it’s a really great read, even if you’re not jacked.