The Largest Arbitrage in Technology - by Evan Lyseng

Just over a year ago I jotted down some thoughts about a pattern I was seeing: venture investors backing software companies to acquire their customers. The idea has caught fire – now branded ‘AI-enabled rollups’ with nearly every Tier 1 venture fund circling the table. Publicly, we’ve seen dedicated vehicles and a quiet second wave is forming in private: Over the past year, I’ve had the privilege of working with and swapping notes with operators who are stitching these platforms together, and decided to sit down and update my preliminary thoughts with some of the lessons we’ve learned. The appeal of AI-enabled rollups is clear: AI has reduced barriers (ie development costs) to building software, so distribution is theoretically more valuable. Agentic software can execute full workflows. If you are selling this software with seat-based pricing, you’re leaving value on the table. Selling software to legacy industries (particularly in SMB categories) has traditionally been difficult for a

Just over a year ago I jotted down some thoughts about a pattern I was seeing: venture investors backing software companies to acquire their customers. The idea has caught fire – now branded ‘AI-enabled rollups’ with nearly every Tier 1 venture fund circling the table. Publicly, we’ve seen dedicated vehicles and a quiet second wave is forming in private: Over the past year, I’ve had the privilege of working with and swapping notes with operators who are stitching these platforms together, and decided to sit down and update my preliminary thoughts with some of the lessons we’ve learned. The app