Sam Hields: What Investors Look for In Roll-Up Founders

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 softwareFront office vs back office automation (and why it matters)Green flags, red flags, and "tourism" in AI roll-up pitchesCapital stack reality — equity, debt, and rollover equityWhere 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