The Rejection Exercise

30 days of rejection encourages founders to seek daily, in-person rejections to build resilience against “no.” My recent enhancements include AI analysis of results to reveal patterns in rejections.
The “Cold Market” as the next hot market.
Attention flows to hot markets. Depending on when you look around, that could be AI, crypto, web3, climate tech, SaaS, Fintech, metaverse, VR/AR, or whatever’s trending now. But what if the best startup opportunities are actually in cold markets that most people ignore? I wrote about a version of this phenomenon in my Why Now […]
More on Gen AI Usage in Entrepreneurship
For the last 2 years I’ve made gen AI mandatory in the classroom, but this semester there were so many useful AI tools and other techniques that I brought them in more heavily. A few examples from a class of grad students testing and potentially launching new businesses: Problem: I had the student founders start […]
What Others Say About Timing
If you’ve been following me here, you know that I spent the last couple years workshopping, speaking, and writing about the impact timing has on the success of a product. In extension of that, the following is an overview of different approaches I’ve found of others dealing with the timing question. The following is an […]
What People Miss About Timing

They say timing is everything in business. But how do you determine if your timing is right?
Measuring Your Market? Consider Timing.

10 years ago today, NYU finance professor Aswath Damodaran, well-known for his work on corporate valuations, posted an article on Uber. The rideshare company was already a unicorn (a new term at the time), with a $17B valuation. Yet, Damodaran ran the numbers and came up with a more modest $5.9B valuation. The title of […]
Surviving the Investment Climate with Unit Economics

Understand unit economics (CAC, LTV, and more) and improve your financial sustainability and odds of raising capital.
50 Timing Examples (the Why Now question)

How does startup timing (or the “why now” question) impact business success? Here are 50 timing examples from startup pitch decks, interviews, and articles.
Running a “Why Now” Session

How to figure out if your product is going to hit the market at the right time.
Avoid the Analysis of Others (Why Now)

If you’re finding this post now, I actually wrote a book about all this… It’s called Why Now: How Good Timing Makes Great Products. You’ll get a fuller perspective there. This is another in the Why Now series. You might also like to read these posts: Why Now: Timing and Product Success and Timing Drivers […]