Cleverly Failing

In doing my year-end review, I was thinking through projects I've worked on this year and the success they've had.

I'm quite happy with where AutoPitch stands. I don't have any paying users at the moment, but I'm talking to customers, getting feedback, and building a roadmap based on where the market is pulling me.

I'm doing something distinctly different from what I've done on all my previously shut down projects.

Project graveyard

Let's recount all the serious projects I've built (those that took more than two weekends): FitVitals, BeeSocial,, Slater, SoloSync, and AutoPitch.

Let's look for the problems that these projects share:

  • poor problem selection (no market)
  • not sticking through The Dip
  • building products on the hunch of clever business ideas

That last one is probably the most insidious, mainly because it leads to what PaulG says the biggest issue is for pre-product founders:

The common trend among my projects is at some point I thought 'Oh, that would be such a clever way to XYZ (make money, get users, go viral).'

And we hear advice like this all of the time. Work Smarter Not Harder™️ right? Everything you do should be high leverage. Outsmart your competition. Build something no one else has thought of yet but that somehow everyone needs.

And all of this is a trap.

This is how you end up with a product that no one wants.

So what's the solution? How do we actually achieve our goals and build software that the world finds useful?

Be dumb about it

This advice isn't for everyone. It's for the people stuck in their heads, trying to come up with the best possible way to do something. Often enough, satisficing is the way to go.

The plan

So what's the dumbest plan that could possibly work when building a SaaS?

  1. Talk to users (lots of them, YC Startup School says at least 5 per week)
  2. Ask them to commit to paying if you fix their problems
  3. Build software

Simple idea; time to take it seriously.

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