๐Ÿ”ต Compass Guidebook: Run a Successful Online Challenge Part 3

How I turned a free challenge into actual revenue (without being a sleazeball)

Estimated Read Time: 6min

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TL;DR

  • Your challenge is worthless if nobody buys something afterward

  • Start with pure value, then introduce logical next steps

  • Lead with free PDFs, then add paid options that solve bigger problems

  • Don't pitch too early - wait until you've proven your expertise

Hey Challenge Creator!

Let's talk about the elephant in the room.

You're not running a challenge just to be nice. (I mean, you ARE nice, but that's not the whole story.)

You want to transform lives AND make some damn money doing it.

So today, I'm pulling back the curtain on how I turned my 28-day ChatGPT challenge into a client-generating machine without making people feel like they were being "sold to" the whole time.

Jan 28th was when I left for the family holiday ๐Ÿ˜ฎ

Mic Drop Moment: Challenges Without Monetization Are Just Expensive Hobbies

I've seen way too many entrepreneurs pour their heart and soul into amazing challenges... then have ZERO plan for what happens next.

That's like building a restaurant, attracting a crowd, and having no food to sell them. They'll leave hungry and you'll be broke.

Let me share the exact value ladder I created that felt like a natural next step (not a sleazy cash grab).

The 5-Step Value Ladder That Actually Converted

Step 1: Free Immediate-Value Content (Pre-Challenge)

Before anyone joined my challenge, I gave away valuable content on podcasts, in groups, and to my email list. I also created a "Fast Track to Learning ChatGPT" course people got FREE just for signing up.

This wasn't fluffy "5 reasons AI is cool" garbage. It was specific, actionable advice people could use immediately.

The key: Each piece ended with "Want more? Join my free 28-day challenge."

Step 2: The Low-Barrier Challenge ($97)

The challenge itself was $97 (about $3.50 per day). Why not free? Because I wanted commitment. People value what they pay for.

What made this work: Every day delivered standalone value while clearly showing there was MUCH more to learn.

One participant told me: "I'm bummed it's the last day of the challenge but excited to continue learning and growing and developing my new AI skills!"

That's exactly the feeling you want to create.

Step 3: The No-Brainer Bonus (During Challenge)

Throughout the challenge, I dropped surprise free PDFs:

  • 50 Workplace Prompts for ChatGPT

  • Maximize Your Time With AI Guide

  • 100 Practical Use Cases

  • 22 Best AI Tools for Content Creators

  • 10 Proven Principles for ChatGPT

The stealth move: These weren't just nice gifts. They demonstrated my expertise and created anticipation for what else I might offer.

Step 4: The Logical Next Step (End of Challenge)

In the final week, I rolled out three different offers:

  • AI Breakthrough Mentorship (1:1 coaching)

  • AI Integration Blueprint course

  • Ultimate AI Accelerator Bundle (everything)

Why this converted: For 28 days, I'd demonstrated my expertise. These offers were clearly the natural next steps for folks wanting to go deeper.

No hard sells. No manipulation. Just the obvious next step for someone who wanted more.

Step 5: The Premium Experience (Post-Challenge)

Two days after the challenge ended, I offered 30-minute strategy calls to anyone who filled out the feedback form.

The surprise: These weren't pitched as sales calls (they genuinely weren't), but several participants asked during our calls how they could work with me further.

I ended up with new 1:1 mentorship clients, sold several courses AND was able to introduce my high-ticket Entrepreneur's Compass offer to the right business owners.

Want your own 5 step value Ladder? You can borrow my Custom
Value Ladder Lab GPT to help you design it. Thank me later.

Ready to see how this value ladder works in real-time? My next ChatGPT Challenge starts 3/31! It's the perfect chance to watch how I implement everything I've just shared with you. Plus, you'll walk away with skills that put you ahead of 97% of the market. Grab your spot here: https://ed.joshuahale.io/chatgpt-challenge

The Non-Sleazy Promotion Timeline That Works

Keeping It 100: What I Learned About Converting Challenge Participants

What Worked Like Magic:

  1. Creating Genuine Transformation First
    People who had actual results were eager to continue the journey.

  2. Using the Challenge to Identify Super Fans
    I watched for who was most engaged, then personalized my outreach to them.

  3. Offering Different Options for Different Needs
    Some wanted 1:1 mentorship, others preferred the self-paced course, and some wanted it all.

  4. Leading with Free Value, Then Adding Paid Options
    Each free PDF primed them for the next level of help I could provide.

What Bombed Completely:

  1. Trying to Sell Too Early
    I started pitching 45 days before the challenge and got crickets. People weren't ready to buy yet.

  2. Not Having Clear Expectations on My Landing Page
    I needed to be crystal clear about what they'd experience to minimize disappointment.

  3. Assuming Everyone Wanted the Same Thing
    I learned I needed to create separate tracks for beginners vs. advanced participants.

The Million-Dollar Question: What's After Your Challenge?

If you've made it this far, you're serious about creating a challenge that matters AND makes money.

The final piece of wisdom I'll leave you with: Your challenge should deliver a complete win while making the next step irresistible.

Think about it like this: If you're teaching people to bake bread, by day 28 they should have a delicious loaf AND be curious about pastries.

Over the past three emails, I've shared the exact framework I used to:

  • Create a challenge concept that attracted 63 participants

  • Structure a 28-day experience that kept them engaged

  • Build a value ladder that converted challenge participants into paying customers

Now it's your turn.

Hit reply and tell me: What will your paid offer be after your challenge ends? I'd love to help you refine it.

Let's crush it,

- Joshua Hale

P.S. Think of your challenge as the first date, not the entire relationship. If you deliver extraordinary value, people will naturally want more of you. No sleazy sales tactics required.

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