The 99 Product Challenge

Finding a Focus

Today, I decided to take one of my product ideas and dig into it more deeply. My first step was to review my idea board and look for a common theme. I knew I wanted to write a book about portfolio management, so I scanned the board for any products and tools related to that topic. From there, I was able to form a small cluster of related offerings.

The portfolio management cluster included:

• Simulations
• Assessments
• Classes
• Coaching
• Meetups
• Other supporting activities

Thinking in Bundles, Not Silos

Rather than treat each idea as a standalone product, I began thinking about how they might come together to enhance the book project. I took inspiration from people like Tim Ferriss, who often package books with podcasts, videos, tools, and other value-added content.

The goal here is to create a more compelling and meaningful portfolio of offerings—not just a book, but an ecosystem. This way, the book becomes a centerpiece around which I can offer supplementary services like training, tools, and community—all potentially marketed and sold together through a dedicated website.

Making Progress on the Book

I also spent some time actually working on the book itself, drafting a few chapters. I’m using AI to help accelerate the process—blending my own written material with slide decks and other content I’ve created over the years.

So far, things are moving along nicely. I’ve already got several thousand words drafted and I’m feeling optimistic about making significant progress in the coming days.

Balancing Work and Life

Admittedly, today was a bit of a challenge in terms of productivity—it was a beautiful Saturday in Seattle, and I had lots of personal commitments. I squeezed in some sailboat racing, enjoyed time with my kids, and tried to make the most of the day.

That meant I had to cram in product work early in the morning and again late in the evening. It wasn’t ideal, but I still managed to keep momentum going—which feels like a small win in itself.