Frameworks, core principles and top case studies for SaaS pricing, learnt and refined over 28+ years of SaaS-monetization experience.
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But AI is rapidly eating away at this past regime.
The Ouroboros is a mythical serpent that swallows its own tail, a symbol of a thing that consumes itself in order to renew itself. The tail is the last cycle’s body. The mouth is this cycle’s appetite. AI does not simply make software cheaper. It runs a loop in which each new wave of intelligence destroys the businesses the previous wave created, and in the same motion makes possible a class of business the previous wave could never have built at all.
These two halves are different in kind. The destruction half is a deflation story: intelligence gets cheaper, moats dissolve, and last cycle’s product becomes something a competitor rebuilds over a weekend. The creation half is a market-maker story. When software can perform work rather than assist it, whole categories of company become buildable that attack budgets software was never allowed to touch. And this animal moves faster than any technology wave before it.
Even before AI, software always deflated. Eggs inflate. Tuition inflates. Medical costs inflate. Software deflates. Go to the Bureau of Labor Statistics and plot it yourself: software worth $100 in 2015 is worth about $60 today. Televisions and toys deflate at similar rates, but software keeps pace or moves faster. And that was before AI showed up.
AI has been an exponential accelerant. Y Combinator reports that 25% of its Winter 2025 batch has codebases that are 95% or more AI-generated. Lovable went from zero to $100M ARR in eight months, then doubled to $200M in four more. What used to take months now ships over a weekend.
When a two-person startup can ship in weeks what used to take a 50-person team 18 months, the pricing power of the incumbent evaporates.
With this commoditization and acceleration in intelligence, software can do more than it ever has. AI software now works in varying degrees of autonomy to act on behalf of its users and deliver outcomes that a human would create themselves, with or without software assistance.