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