Investing 101

Investing 101

Networked Conviction 004

AI Rollups That Don't Suck

Kyle Harrison's avatar
Kyle Harrison
Feb 21, 2026
∙ Paid

This is an entry in Networked Conviction: My Investing Journal; a weekly newsletter for my paying subscribers where I share portfolio updates (including current, future, and anti-portfolio mentions), Requests For Startups, and investing ideas. To access this newsletter weekly, subscribe here:


As part of Networked Conviction, the paid portion of my newsletter, I set out with the intention of revolving my thinking around three different buckets: (1) portfolio updates on the companies I’ve invested in, (2) my own version of Request For Startups, and (3) general investing ideas (frameworks, templates, etc.)

After two editions from my idea journal and one with a portfolio update, I’m finally doing my first request for startups. The insights around this idea come from existing portfolio companies that have already done portions of this, companies I’ve seen but didn’t invest in and what I thought should have been differently, as well as legitimate greenfield I see in the market for someone with passion and a plan to make a difference.

The request? AI rollups that don’t suck. The idea of a rollup has taken the world by storm, but the vast, vast majority of pitches I hear for AI rollups typically have a fundamental misunderstanding of how rollups work... or how AI works... or both. I recently articulated to a friend what the formula for an AI rollup that doesn’t suck ought to look like.

So here we go!

User's avatar

Continue reading this post for free, courtesy of Kyle Harrison.

Or purchase a paid subscription.
© 2026 Kyle Harrison · Privacy ∙ Terms ∙ Collection notice
Start your SubstackGet the app
Substack is the home for great culture