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Cubicle to CEO

Profitable Paid Challenges (Part 2: Structure)

Cubicle to CEO

Ellen Yin

Marketing, Business, Entrepreneurship

5.0580 Ratings

🗓️ 4 February 2026

⏱️ 12 minutes

🧾️ Download transcript

Summary

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Transcript

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0:00.0

Could AI help you do more of what you love?

0:03.1

Workday is the next-gen ERP powered by AI that actually knows your business.

0:08.4

We help you handle the have-to-dos so you can focus on the can't-wait-to-dos.

0:13.2

It's a new workday.

0:25.2

This is part two of a two-part series on profitable paid challenges.

0:30.6

For today's episode, we're going to be more focused on how we actually structure the back end of our paid challenges and some of the things that I think make the experience

0:35.9

raveworthy for our attendees and overall just create

0:40.1

a more unique challenge experience again compared to some of the other ones that we've

0:45.1

experienced in our industry. So here in no particular order are some of the things that I think

0:51.0

make our paid challenges really successful. Number one, this is probably

0:55.1

the most important one. Our paid challenge is a three-day challenge. Now, there's no magic

0:59.7

time frame. I would say that if you want high engagement, anything under a week is probably your

1:04.9

best bet. But more importantly, we're really focused on creating a specific, tangible outcome from our paid challenge.

1:12.9

You really want to make sure that when you're hosting a challenge, that there is some sort of

1:16.7

immediate result or fast action win that they can leave the challenge having completed.

1:23.6

So this is not where you want to place a really long-term goal on your students. So for example,

1:30.3

our challenge paid to create is all about helping first-time course creators turn their existing

1:36.3

knowledge into an online course that they can pre-sell to paying students within three days.

1:43.1

So in a 72-hour window, we literally help them go from

1:47.2

idea to income. And they can get their first paying student in the door by the end of our

1:52.5

challenge. This is very specific, right, because we're only focused on the pre-sell phase of their

1:58.6

course and getting them the minimum viable product and checkout

...

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