The 99 Product Challenge

It’s officially two weeks into the 99 Product Challenge, and I’ve hit the halfway point. That makes this a perfect time to pause, reflect, and tally up what’s been accomplished so far.

20 Products in 14 Days

Here’s the list of product ideas that have already become live, buyable offerings—available either through my website or third-party platforms:

1. Enterprise Coaching
2. Introduction to Business Agility
3. Design Your Operational Model
4. Business Agility Workshop
5. Intro to Portfolio Management
6. Portfolio Management Workshop
7. Value Stream Design
8. Intro to Team Dynamics
9. Managing Remote Teams
10. Team Dynamics Workshop
11. Building Great Working Agreements
12. Intro to Adaptive Strategy
13. Adaptive Strategy Workshop
14. The Little Book of Portfolio Management
15. Agile Mixins Book
16. The Geek’s Guide to Agile Facilitation
17. Consulting via Clarity and Freelancer
18. Substack Writing
19. The 99 Product Challenge
20. Disruption Dynamics

If you had asked me two weeks ago whether I’d have a dozen real, shippable products by now, I might’ve said that was a stretch goal. But here we are—twenty products in, and frankly, I’m blown away by the pace and momentum.

Strategy: Pipelines and Product Pairs

As you look through the list, some patterns might stand out. One deliberate approach I’m using is to break larger offerings into a pipeline of smaller, connected products.

For example, I’ve started developing both introductory and advanced versions of key offerings. A lower-priced intro course helps generate interest and draw people in. Once they’re engaged, the more intensive (and more expensive) workshop becomes a natural next step.

This tiered model creates multiple entry points for different audiences and builds a healthy funnel for continued engagement. Over the next two weeks, I plan to lean into this approach even more, especially as I learn which products generate the most traction.

The Work Doubles from Here

Now that I’ve built a solid base of products, the real challenge begins: marketing, relationship-building, and iteration.

Just because a product exists doesn’t mean people know about it. So the second half of the challenge is going to involve:

• Getting products in front of the right audiences
• Listening to feedback
• Making improvements
• Building partnerships and visibility

Case in point: my calendar is already filling up with calls from folks who’ve come across my work and want to learn more. Tomorrow I’m heading down to the local Chamber of Commerce to meet new people and build community connections. It’s going to be a lot of networking, listening, handshakes—and probably a bit of “kissing babies,” metaphorically speaking.

And honestly? I couldn’t be happier.

What’s Next

At the halfway mark, I’ve already surpassed my own expectations. But I’m not slowing down. With two more weeks to go, I’m aiming to:

• Launch even more products
• Double down on outreach and feedback
• Refine what’s already been built
• See just how far this momentum can take me

So that’s your quick status update. Twenty products down, with many more to come—and a lot of exciting conversations already underway. Onward!