Profitable Paid Challenges (Part 1: Monetization)
Cubicle to CEO
Ellen Yin
5.0 • 580 Ratings
🗓️ 2 February 2026
⏱️ 12 minutes
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| 0:00.0 | Could AI help you do more of what you love? Workday is the next-gen ERP powered by AI that actually |
| 0:06.8 | knows your business. 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. |
| 0:26.2 | As you can tell by the title, today's episode is part one of a two-part series on profitable paid challenges. I thought the timing of this episode would be perfect because |
| 0:32.1 | this October, we are actually running our 11th cohort of paid to create, which is our live three-day challenge |
| 0:38.7 | helping first-time course creators pre-sell an online course and actually get paid to create |
| 0:44.2 | their first online course. And having run this challenge now for 10 successful cohorts, |
| 0:49.5 | about to be our 11th, and then also last year actually happened to be October 23, so almost exactly a year ago. |
| 0:57.7 | We also tested an all access group, a very small, intimate group that I kind of let into the behind |
| 1:04.9 | the scenes process of exactly how we monetize and structure our paid challenges because they are so different from most of |
| 1:13.1 | the paid challenges that I have seen or been a part of in our industry. I don't know if I plan |
| 1:18.3 | to run that all access group again. It was a $1,500 experience. And I really wanted to be able to share a little behind the scenes of both the |
| 1:31.3 | monetization piece, which we're talking about today, as well as the structure piece of |
| 1:35.1 | these paid challenges with a wider group. And I thought this would be the best format to do |
| 1:39.5 | so because I can walk you through the high level of both sides of the coin, the monetization side, |
| 1:44.5 | and again, the structure side, which I think you guys will be able to apply this to a paid |
| 1:49.6 | challenge that helps people with whatever you are an expert in. So that's kind of the context |
| 1:56.0 | of why I landed on this topic. But let's talk about, you know, how paid challenges even fit into |
| 2:02.7 | our ecosystem. Because most people who host challenges or boot camps, they're kind of |
| 2:09.2 | interchangeable for the most part. Most people host them as free events for lead gen purposes. |
| 2:15.3 | So you'll see this all the time where people host like a three day, |
| 2:17.9 | five day, maybe 10 day challenge, where they're really just trying to collect the maximum |
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