I went live with Jennifer Dragonette a few days ago.
She’s a bestselling author, a storytelling strategist, and a top 1% podcaster. She also had 19 Substack subscribers. And she already landed a high-ticket coaching client off this platform.
Nineteen.
Sit with that number for a second. Because every time someone tells me they “need 10k subscribers before they can monetize,” I think of conversations like this one.
What's her secret?
No secret. She just applied the strategies in the SUBSTACK QUEST with what she already knows best: how to use storytelling for business.
You can watch the full recording above. But if you want the condensed version, here’s what stuck with me.
The quote I can’t stop thinking about
Halfway through the live, I asked Jennifer what she thinks about Substack compared to the other platforms she’s used.
Here’s what she said:
“I have 19 subscribers and I already got a paid client from here.”
Then she clarified. It wasn’t a paid subscriber. It was a high-ticket client. Someone found her on Substack, a conversation happened, and that person became a high-ticket client.
19 Substack subscribers → one high-ticket client → pretty decent money off Substack already.
Compare that to the standard growth advice. Grow first, monetize later. Wait until you hit 10k.
You know me, I lean on data. And the data says something different. Monetization isn’t about audience size. It’s about the match between the reader and your offer.
Jennifer is the living proof.
Why she’s done chasing virality
Jennifer came to Substack burned out.
Top 1% podcast. Bestselling book. Keynote on a stage of 3,000 people last year. All the metrics most creators are trying to hit.
And she said this, out loud: “I’m done with virality.”
Ok, let me tell you why that line hit me. A lot of us nod along the first time we hear something like this - and then go back to chasing subscirbers on Notes the next morning.
Jennifer’s argument is different. She’s not saying virality is bad. She’s saying it didn’t build her business.
Her top 1% podcast, her viral stage moment, her thousands of listeners - those didn’t move the needle the way one real Substack conversation with the right person did.
She calls it “look at me” content versus “oh my goodness, that sounds like me” content.
The second one is what converts.
And Substack, she argues, is structurally built for the second one. “It’s a depth platform,” she said. “I like to go deep with people.”
The storytelling technique that changed how I think about content
This was the part of the live where I had to stop and process.
I asked Jennifer for one technique anyone could use to find their story. I was expecting a framework. Three steps. Maybe a worksheet.
Her answer:
Record yourself telling your whole story. Then listen back. Pay attention to where your body reacts.
That’s it. That’s the whole method.
“There’s going to be parts of that story that are going to react in your body,” she said. “Those are the parts that you infuse into your thing.”
Here’s why this is brilliant.
Most people try to manufacture a story that “sells.” They look for the problem hook. The one that sounds marketable. The transformation story that’ll test well on a sales page. And the result is content that sounds performative….because it is.
Jennifer’s method flips it. Your body already knows what matters. The lump in your throat, the tightening in your chest, the place where your voice catches- those are the moments of actual truth. And those are the only moments that transfer emotionally to a reader.
Try it this week. See what happens.
The metric that isn’t a vanity metric
Finn Tropy asked a great question in the chat: how do you quantify storytelling beyond engagement metrics?
I watched Jennifer light up.
Her answer surprised me.
“For me, 19 subscribers and a paid client - that’s a pretty good metric.”
And she asked me back: “If that was your metric, would that be enough for you for knowing a story was great?”
Ok, I’ll be honest. I’m a data person.
My version of her answer would probably involve conversion rates, cohort analysis, and a dashboard. I shared with her that I currently run around 9–10% free-to-paid conversion for readers coming from Notes and recommendations — which is well above the Substack benchmark, and it’s a number I track closely.
But Jennifer’s deeper point is right. Engagement for its own sake is noise. The real metric is whether it landed somewhere. Whether it changed something. Whether a person did something different because of what you wrote.
Her 19-to-1 ratio? Actually, that’s a better conversion than mine.
Your competitors aren’t competitors
I believe competitors are your best collaborators.
And Jennifer shares this belief.
When she talks about other creators in her niche, she doesn’t call them competition. She says they’re “hanging out on your block.”
“We’re having a block party,” she said. “Who can you kind of collaborate with - their audience might share your audience, you might be able to give and take.”
This is such a better model than the scarcity-brained creator advice of “find your gap in the market and defend it.” Especially on Substack, where the whole platform is built around collaborations, cross-recommendations, restacks, and guest appearances.
Her entire business runs on referrals. Not because she has some sophisticated affiliate program. Because she showed up and gave first, for years. The block party kept growing until it became a business.
If you’re wondering what to actually do on Substack besides posting - this is it. Go to the chat. Do restacks with intention. Set up lives. Comment meaningfully on people you actually admire. Reach out for a collab. That’s the work.
What she’d do differently (this is the good part)
I asked Jennifer what she’d change if she could rewind her Substack journey.
Three things:
Turn on paid from day one.
Launch the founding membership immediately.
Go back to the foundations before anything else.
“Substack offers you such great opportunities,” she said. “I would have turned on paid sooner. I would have launched my founding membership as my community.”
This is exactly what I keep telling new writers. And Jennifer is the proof of why it matters. She enabled paid once she realized what was possible - and within weeks she had a high-ticket client from the platform.
Most people wait until they have “enough” subscribers before they monetize. And they miss the window where the tiny, early audience is often the most ready to buy.
If you’re new here and still holding off on turning paid on — this is your sign.
One thing I’d add to what Jennifer said
Jennifer’s whole argument is that Substack rewards depth over surface. I agree with her. But I’d add a layer.
Depth without structure is still a hot mess.
Jennifer said this herself. She described her early Substack as “a hot mess express.” Then she went through the QUEST, did the foundations, tightened her positioning, clarified her offer - and the results followed within weeks.
The story matters. But the story has to be attached to an offer someone can actually buy.
That’s the piece a lot of storytelling-first creators miss. They get so invested in crafting the narrative that they forget to build the product underneath it. Then they wonder why the beautiful writing doesn’t convert.
Jennifer’s 19-to-1 happened because the story AND the offer were both in place. Not one without the other.
The TLDR version
If I had to compress this live into something you can actually use on your Substack this week:
You don’t need a big audience. You need the right readers and an offer that fits them.
Find the parts of your story that react in your body. Those are the parts worth sharing. Everything else is filler.
Stop chasing virality. Start chasing depth. Substack is built for the second one.
Turn on paid on day 1. Not after 1k subs. Not after 10k. When the offer is clear - that’s where you start.
And talk to people. In the chat. In restacks. In lives. Substack is not a content machine, it’s a place to connect.
Watch the full live above for the parts I couldn’t fit in here. Jennifer goes deeper on the storytelling method, the referral strategy, and the moment she almost tapped out of Substack early on.
And if you’re into story-first business, subscribe to Jenn’s publication - she’s one of the most grounded, vulnerable, and practical voices I’ve met on this platform in a long time.
Read Jen’s book: Your Story is Someone’s Life Raft - Your story is your superpower. Learn how to tap into its power to unleash your tsunami of change!
Yana
P.S. Jennifer mentioned the QUEST several times in the live, that’s the 7-domain Substack strategy system she went through before her foundations clicked. If you want what she had, it’s right here.
👉 Start a discussion in the Unplugged community! Get help or simply introduce yourself and connect with like-minded members, and create meaningful connections.
Kickstart Your Substack Growth:
Get a FREE 10-Day Substack crash course to grow your first 1000 subscribers
Join my FREE Masterclass on how to start making consistent $5,000/month
Join the One and Only Substack Quest to build a high-converting Substack
Work with me to get your Substack up and growing
Save Tons of Time! Use My Custom GPTs:
The Title Generator that gives me headlines that stop the scroll
The Notes Writer that writes Viral Notes, bringing me and my paid members hundreds of subs
The Writer Pro that turns my Notes into >90% human drafts (here’s the free version).
Or get the bundle with all the tools, now at a very special price ;)
Become an Affiliate:
Earn 30% from each sale. Apply below, I approve everyone.
Apply here for my Gumroad store
Apply here for my Teachable school
Become a sponsor:
Reach thousands of engaged buyers.
More from me:
FREE Daily BiTES: A daily mail with just 3 bullets from the most helpful things I read about writing and making money online with AI
Unplugged: The place to be if you want to grow an AI-powered paid newsletter and create content that sells itself.
