Podcast Episode 70 — Running Our First Major Challenge: The Real Numbers, Strategy, and Why It Worked
Running a successful multi-day challenge often looks simple from the outside.
A few live sessions.
Some community engagement.
A final offer.
But behind the scenes, there’s far more happening than most people realize.
In Episode 70 of The Digital Shift™, Jessica Green pulls back the curtain on Self Made’s first major challenge at scale—sharing the real numbers, the real strategy, and the lessons learned along the way.
No hype.
No highlight reel.
Just a transparent look at what it actually takes to run a profitable challenge.
Because challenges don’t succeed by accident.
They succeed by design.
Why We Decided to Run a Challenge
The decision to run a challenge wasn’t driven by hype.
It was driven by infrastructure.
Today’s digital marketplace is experiencing what many entrepreneurs call a trust recession. Buyers are slower to commit and more cautious about where they invest their time and money.
While workshops can provide quick value, multi-day challenges offer something deeper:
Daily proximity with your audience
Repeated trust-building touchpoints
Real-time implementation
Community-driven momentum
Instead of simply watching content, participants actively build alongside you.
For the Self Made audience—entrepreneurs stuck between big business visions and confusing tech systems—a structured challenge provided the perfect environment to create clarity.
The Real Numbers Behind the Challenge
Transparency matters when discussing marketing strategies like challenges.
Here’s what the data looked like for our first major challenge.
Ad Spend
Total ad spend on Meta platforms:
$7,174.94
These ads drove both registrations and workbook purchases.
Ticket Revenue
Initial revenue from challenge tickets and workbooks:
$5,540
On ticket sales alone, that resulted in a negative ROAS of 0.77.
But this is where many entrepreneurs misunderstand how challenges work.
Tickets are not the primary revenue source.
Total Event Revenue
Total revenue generated from the challenge so far:
Approximately $20,000
This included:
Program enrollments
Upsells following the challenge
Follow-up sales calls
That brings the overall return to approximately 2.78 ROAS—meaning every $1 spent on ads generated about $2.78 in revenue.
And that number will likely increase as follow-up sequences continue.
Show-Up Rate
Out of roughly 45 registered participants, about 28 attended live sessions daily.
That’s around a 60% show-up rate, which is strong for a paid challenge.
Paid environments attract builders—people committed to participating and implementing.
Conversion Rate
Immediate purchases after the challenge totaled:
6 confirmed sales, with 2 additional prospects likely to convert.
That places the conversion rate between 13% and 18% of attendees.
And many challenge conversions happen weeks later through follow-up emails and calls.
What Made the Challenge Work
The success of the challenge wasn’t just about great content.
It was about structure.
Each day of the challenge focused on one clear outcome.
Day 1: The Tech Reality Check
Participants assessed the tools and systems currently running their businesses.
This helped them identify:
overlapping software
lead leaks
unnecessary complexity
Because automation can’t fix chaos.
Day 2: Communication and Follow-Up Systems
Participants mapped the complete conversation journey:
Comment → DM → Lead → Nurture → Call → Client.
Many businesses don’t lose sales because of weak offers.
They lose sales because follow-up systems are broken.
Day 3: Revenue Infrastructure
The focus shifted to the systems supporting revenue:
offers
payment flows
forms
product delivery
When someone says “yes,” the buying experience must be seamless.
Otherwise, a business doesn’t have a system—it has stress.
Day 4: Delivery and Automation
Scaling happens during delivery, not marketing.
Participants mapped systems for:
onboarding
automation
course access
testimonial collection
A strong backend ensures that growth doesn’t create operational chaos.
Day 5: The Next 90 Days
The challenge concluded with participants building their own 90-day execution plans.
Instead of leaving with inspiration, they left with clear direction.
The Systems Behind the Challenge
What most attendees didn’t see was the infrastructure powering the entire event.
Key systems included:
automated checkout flows
tagging and segmentation
reminder emails and SMS
replay delivery automation
homework tracking threads
sales pipeline management
automated cart close sequences
Without this technical backbone, the challenge would have been impossible to run smoothly.
Automation allowed the team to focus on teaching and supporting participants rather than chasing logistics.
Lessons We Learned
Even successful events offer opportunities for improvement.
Future challenges will include:
more networking time early in the event
live testimonials throughout the week
slightly longer sessions for deeper implementation
an improved virtual challenge dashboard
These changes will create even smoother participant experiences.
10 Tips for Running Your Own Challenge
For entrepreneurs considering hosting a challenge, here are several key lessons from our experience:
Focus on one transformation.
Teach concepts in logical sequence.
Start advertising earlier and push harder in the final 72 hours.
Use one clear call-to-action.
Build community threads immediately.
Offer premium experiences like audits or hot seats.
Track numbers daily.
Automate reminders using email and SMS.
Deliver replays automatically.
Follow up after the challenge—most revenue happens there.
Challenges aren’t magic.
They’re engineered.
Want to Run Your Own Profitable Challenge?
If you’re ready to build a challenge that actually converts—without duct-taping tech or guessing your way through it—the Self Made team teaches the entire structure inside Challenge Lab.
Inside the program you’ll learn:
the strategic framework
automation setup
daily content structure
challenge conversion strategies
👉 Join the next Challenge Lab:
https://www.self-made.biz/challenge-lab
You can also experience the process firsthand by joining the next 5-Day Go High Level Without the Guessing Challenge.
Final Thoughts
The biggest lesson from running our first major challenge was simple.
From the outside, the event looked easy.
Behind the scenes, the infrastructure was anything but.
But when the systems were in place, the challenge became scalable.
Because momentum isn’t luck.
It’s engineered.
And the entrepreneurs who understand that are the ones building the future.
