The brutal question every VC asks an AI roll-up founder: where's the headcount going to drop? Sam Hields breaks down what separates a venture case from a financial engineering pitch.

Sam Hields (Partner, OpenOcean) joins Dylan to discuss why services will eat software in the AI era and what VCs actually look for in roll-up founders.

Topics covered:

• Why services is a 10x bigger market than software
• Front office vs back office automation (and why it matters)
• Green flags, red flags, and "tourism" in AI roll-up pitches
• Capital stack reality — equity, debt, and rollover equity
• Where AI expands TAM (and where pricing collapses instead)

RolyPoly is the podcast about all things roll-up. New episodes every Tuesday.

Connect: pmistack.com | linkedin.com/in/dylan-harrocks