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This AI Prompt Turns $27 Customers Into $2,000 Customers (Digital Product Ladder Strategy)

ByJillian Leslie

Most creators are stuck on an exhausting hamster wheel. They’re constantly hunting for new customers to buy their $27 product. Let’s say they make a hundred sales in a month. Great job! But next month, they start all over, hunting for those same $27 customers again.

But what if that same customer became worth $2,000 to your business? Same effort to acquire them, but 235 times more profitable.

Bethany, one of our MiloTree customers, did exactly this. She made $11,000 last month with a small email list of just a few hundred subscribers—because she figured out how to sell more to each customer.

 

 

Show Notes:

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The $27 Trap: Why Most Creators Are Leaving Money on the Table

Here’s what most of us do: We create that one product, price it at $27, and pour all our energy into getting new people to buy it. We’re constantly putting up Instagram posts, Pinterest pins, writing blog posts, sending emails, running ads.

And even when it works, the math is terrible.

Let’s say you get 100 new customers at $27 each. That’s $2,700. Sounds good, right?

But next month, you need 100 more new customers to make that same $2,700. It never ends. You’re always hustling for new people.

Meanwhile, those 100 customers you already have? They trusted you enough to buy once—but you’re ignoring them while you chase strangers.

That’s where most creators are leaving thousands of dollars on the table and burning out.

If you’re feeling this exhaustion, you’re not alone. In my post on why people won’t pay for information anymore, I talk about how the old model of selling one product isn’t working in 2026. The solution isn’t more hustle—it’s a smarter business model.

What Is a Digital Product Ladder?

Here’s what smart creators do instead. They build what I call a digital product ladder, and it completely changes the economics of your business.

Instead of selling one thing and moving on, you create a journey for your customer:

The 6 Rungs of a Product Ladder

  1. Freebie/Lead Magnet – This is how you earn their trust. They end up on your email list.
  2. Tripwire Product ($27) – Something small that goes deeper at solving their problem. They buy it, get results, and now trust you even more.
  3. Product Bundle ($97) – A comprehensive solution combining multiple resources.
  4. Course or Coaching ($297) – Premium transformation and deeper support.
  5. Membership (Recurring) – They’re paying you every month for ongoing value and community.
  6. Mastermind/High-Touch Program – For serious implementers who want direct access to you.

Same customers. One acquisition cost. But instead of making $27, you’re making over $2,000 over time from that same person.

And here’s the beautiful part: Each sale after the first one costs you almost nothing. They already know you. They already trust you. They are easier to sell to than a complete stranger.

This is exactly why I teach the upsell and order bump strategy inside MiloTree—it’s the fastest way to increase your customer lifetime value without finding new customers.

The AI Prompt That Builds Your Entire Ladder

I created an AI prompt to build your entire ladder in one session. Here’s exactly how it works.

Go to ChatGPT and paste this in:

Help me create a complete digital product ladder for [YOUR NICHE] and the problem you solve.

Create a six-step customer journey that transforms a free subscriber into a high-value customer.

Step 1: Create a valuable freebie that solves one specific pain point and delivers a quick, tangible win.

Step 2: Design a tripwire product. This product naturally follows from the freebie and provides deeper value.

Step 3: Develop a product bundle that combines multiple resources for comprehensive results.

Step 4: Structure a mini course or coaching package that ultimately leads customers into joining your membership.

Step 5: Design a monthly membership that provides ongoing support and community.

Step 6: Create a premium mastermind or high-touch program for serious implementers.

For each step, provide the product concept, the main benefits, your suggested price, and how it connects to the next level.

Watch what happens. Boom—in 30 seconds, AI just mapped out your entire business model.

Yours might look a little different, but notice how each step builds trust and relationship with your customer so they naturally want to keep going with you.

👉 Grab the complete Digital Product Ladder AI Prompt as a free download

How to Set Up Your Product Ladder in MiloTree

Here’s where most people get stuck. They think, “Okay, great. But how do I actually build all of this without losing my mind?”

This is where MiloTree becomes your best friend.

Setting Up Your Freebie

In your MiloTree dashboard, you can set up your freebie in minutes. MiloTree generates the email opt-in page and delivers your freebie automatically to your subscriber on the thank-you page.

Adding Your Tripwire

Your tripwire product gets set up as a normal product in your dashboard. Then you choose it to show up right after someone downloads your freebie. They’re already excited, and boom—you can offer them that $27 product right there on the thank-you page.

Notice how everything leads organically to the next offering.

Bundles, Courses, and Memberships

Your bundles, courses, and memberships all live in one place. And MiloTree’s AI writes your sales pages for each product.

Plus—this is huge—you can add order bumps, upsells, and coupons. So when someone buys your $97 bundle, you can direct them into the right next product, right when they’re most ready and with the right incentives.

That’s how you maximize every customer relationship.

Pricing That Makes Sense

  • Free Plan: Perfect for testing. Sell a product, offer a freebie, add a social media pop-up to grow your followers—all free forever.
  • Grow Plan ($19/month): Build your full ladder with tripwires, upsells, multiple products, and multiple freebies.

Think about it: For less than the cost of one coffee per week, you can manage your entire customer journey that’s generating thousands in revenue.

Sign up for MiloTree’s free plan and start building your ladder today

Bethany’s Real Results: From Zero to $11,000/Month

Bethany started with just one freebie: “How to Look for a Job After Staying Home With Your Kids.”

Then she added a $27 daily planner for moms looking for jobs. People bought it and asked for more—so she created a bundle.

Then they wanted ongoing support, so she added a membership for moms getting back into the workforce.

Each step was fast. Each step was tested with real people. Each step built off the previous one.

Six months later? Boom—she’s making $11,000 a month.

And that’s the game. You want to move fast. You want to listen to your customers and give them what they’re asking for. The ladder builds itself when you focus on actually serving your people.

The math is simple: It’s way easier and cheaper to sell to somebody who already trusts you than to convince a stranger to buy.

Your Action Plan: Start Today

Here’s what I want you to do right now:

Step 1: Grab the AI Prompt

Download my complete Digital Product Ladder AI Prompt — it’s free. Run it for your topic tonight. Don’t wait.

Step 2: Sign Up for MiloTree’s Free Plan

Sign up here — no credit card needed. Set up your freebie lead magnet, test it, and see how easy this all is.

Step 3: Build Your Full Ladder

When you’re ready to build your full ladder, upgrade to one of our paid plans. They start at just $19/month. Most people do this within the first two weeks of signing up.

What gets them upgraded? The ability to offer multiple freebies to grow their email list faster—so they have more people to sell to.

The Bottom Line

With MiloTree, you have everything you need to turn that $27 customer into a $2,000 customer.

Stop chasing strangers. Start building real relationships.

That’s how you get to $1,000, $5,000, $10,000 a month without burning out.

Ready to build your product ladder? Start with MiloTree’s free plan →