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

EVE found 400 missed leads in one founder's inbox and closed six-figure deals from them. Vadim Rogovskiy explains how AI is rewriting the acquisition playbook.

Vadim Rogovskiy (CEO, EVE / Founding Partner, Rebel Capital) joins Dylan to discuss acquiring legacy businesses, layering AI to unlock hidden revenue, and why roll-ups are just getting started.

Topics covered:

• Exit timing mistakes and why founders hold on too long
• How EVE discovered $20M in hidden pipeline across client inboxes
• AI agents replacing operations teams (4 people to 1)
• The roll-up landscape: venture returns with PE risk profiles
• Using AI for due diligence and founder outreach at scale

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

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

Most acquirers treat deal sourcing like a numbers game. Andrew Ofori left Goldman Sachs to prove there's a better way.

Andrew Ofori (CEO & Founder, Bloomvine) joins Dylan to discuss strategic deal sourcing for PE-backed roll-ups and acquisitive corporates.

Topics covered: • Why your first 2-3 acquisitions determine the success of your entire roll-up • How culture and language shape cross-border deal sourcing • AI tools reshaping acquisition workflows quarterly • Outreach tactics that actually get sellers to respond • The market rotation from software into asset-based businesses

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

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