I’m Bob Moore. I’m the CEO and Co-founder at Crossbeam, and a serial SaaS founder, AMA!

Thanks for the question and for the RJMetrics nostalgia!

I think your question is actually offering a false choice. There are many dimensions on which a company might be considered a good idea or a bad one, but I don’t think entering into a market with existing players – even a lot of them – should be a wholesale disqualifier. Nor should category creation be viewed as a golden ticket or something to avoid.

When deciding which business to pursue next (in this most recent wave when I chose Crossbeam), my framework was more about:

  • Founder-market fit: Am I uniquely suited to creating success in this business and laying out a vision that will be differentiated and succeed?
  • Total upside potential: is the TAM large? what are the break points (“kinks in the growth line” that you can foresee) and are they addressable or preventable?
  • Is there a good answer to the “why now?” question?
  • The fun factor: Am I fascinated enough by the problem set to fully live in it for years to come? Can I trigger that passion in other people when I talk with them about the idea?

The fact that Crossbeam was a category-creation play and RJMetrics was a crowded market play were not in the top 5 inputs.

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