Five Predictions for the 2028 Software Landscape (With Receipts)
I’m going on the record with five contrarian calls — from which AI startup hits $100B first to the structural shift that will decide winners and losers for the next decade.
Series: Part 3 of 3 — The SaaSpocalypse Series
In Part 1, I laid out the evidence that AI-native startups are dismantling traditional SaaS — and introduced a practical filter to tell what’s vulnerable from what’s safe. In Part 2, I mapped the opportunity landscape: claimed territories, next-wave verticals, and the meta-layer infrastructure that ties everything together.
This week, I’m doing something uncomfortable. I’m making predictions — five of them — and going on the record with confidence levels for each. These aren’t safe, consensus-friendly forecasts. Every one of them challenges something the current market takes for granted. Some will age beautifully. Some will age like milk. Either way, you’ll know exactly where I stand.
Why Predictions Matter (Even When They’re Wrong)
I’ve always been skeptical of prediction pieces. Most of them are written to sound smart without risking anything — hedged so thoroughly that they’re unfalsifiable. “AI will continue to grow.” “Some SaaS companies will struggle.” Thanks for nothing.
So here’s my commitment: every prediction in this piece includes specific, falsifiable claims with timelines. By 2028, you’ll be able to score me. I’ve assigned each prediction a confidence level, not because I’m unsure about them, but because intellectual honesty demands acknowledging the difference between “I’m almost certain” and “I’m betting on this but the counterfactual is real.”
Why does this matter for founders? Because your startup strategy is a prediction. Every product decision, pricing model, and go-to-market play is a bet on where the market is heading. The founders who win aren’t necessarily smarter — they’re the ones who make their assumptions explicit, pressure-test them, and adjust faster when reality diverges.
Here are my five bets.
