The End of Predictability

When the Old Strategy Stops Working

For a long stretch, tech felt like a game with a “known” cheat code.

Build a product, ride the bottoms-up wave, run your enterprise motion, stack ARR, and raise at each milestone. Even the way hyperscalers played with startups was formulaic: launch a partner program, host a few dinners, and the founders would beat a path to your door.

But that old paradigm is showing its age.

AI didn’t just redraw the map. It scattered the pieces. Product categories are turning over every six weeks. Startups that used to be “experiments” are landing Fortune 100 logos before the paint dries on their Series A. The SaaS-era script (build, land, expand, repeat) now feels about as relevant as “move fast and break things.” Predictability? That’s become a myth we tell ourselves before the next board meeting.

I hear it everywhere. Operators who used to have a perfect line of sight are getting blindsided by new clusters of fast followers, new teams moving from company to company, and all the new tools. The seasoned plan is out. Sensing is in.

And here’s the uncomfortable truth: We’ve all gotten a little lazy. As investors, we’ve clung to metrics, classic enterprise SaaS KPIs like ARR (which can now mean whatever the **** a founder wants it to mean), NRR, even logo count, that used to mean something deep about a company’s health. But in this new cycle? Those numbers are starting to look like vanity stats. The real signal is shifting. Enterprise and B2B tech motions are starting to look more like old-school consumer: engagement, daily active users, monthly active users, true product stickiness. The boardroom is catching up to what consumer investors have known for years: if your product isn’t getting used, you don’t have a business, you have a spreadsheet.

So what do you do when the familiar patterns break down?

1. Trade the Old Blueprint for Sensing

You can’t just double down on execution. You have to double down on listening. Every signal, startup programs, Corp Dev, CVC, product, sales, customer/industry trend, competitor growth or slowdown, needs to be rolled up, not siloed. Don’t let them run in parallel. Aggregate, rank, and review what you’re seeing. Meet every two weeks, not quarterly. If the market is changing every six weeks, your learning loop can’t be on a quarterly clock. The winners will be the ones who build a nervous system, not just muscle.

2. Shrink Your Decision Window

This one is for the large organizations. Corporate innovation, I say this with love: slow committees are a luxury you can’t afford. The AI era punishes hesitation. Move to 2–4 week pilots. Set clear KPIs, clear owners, and a clear “continue or kill” moment. No more “let’s see how it goes over Q3.” Try, measure, decide, repeat. The teams that build this reflex will outlearn the market.

3. Treat Distribution Like Product

This one is for my founders (and investors). In an AI-driven, services-first world, distribution is the new moat. If you can be the connective tissue between AI-native startups and the buyers who suddenly have an AI budget, you’re not just a vendor. You’re a bridge. Distribution is no longer a postscript. It’s the product that keeps you in the game.

4. Let Churn Be a Teacher

Here’s the part that stings: even great products are going to see logo churn. Budgets are more experimental today, but won’t be very soon. Buyers are trying before they’re buying. Churn isn’t always a verdict on value. It’s a reflection of volatility. Don’t panic. Build faster learning loops and more channels. Make churn a data point, not a death sentence. Learn how to get to the business unit decision maker faster and better.

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Here’s the TLDR I keep giving to founders, LPs, and corporate innovation teams: you’re not supposed to have all the answers right now. Nobody does. Not even the hyperscalers. The ones who’ll win are the ones who admit that early—and build the sensing, distribution, and trust systems to keep learning when predictability is gone.

We’ve left the SaaS era. The next era belongs to those who can find their stance in the storm, read the set before it breaks, and paddle out anyway.

~e