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

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 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 [http://pmistack.com] | linkedin.com/in/dylan-harrocks [http://linkedin.com/in/dylan-harrocks]

Vadim Rogovskiy on Why AI Makes Roll-Ups Unstoppable

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 [http://pmistack.com] | linkedin.com/in/dylan-harrocks [http://linkedin.com/in/dylan-harrocks]

Andrew Ofori on Deal Sourcing: How to Actually Get a Seller to Respond

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

Andrea Allegrini on HVAC Roll-Ups: More Plumbers, Less Managers

Italy has 12,000 HVAC companies and no national player. Andrea Allegrini from Lindbergh is building the first one — 14 acquisitions in two years, zero competition. Andrea Allegrini (Head of Waste Management & IR, Lindbergh S.p.A.) joins Dylan to discuss how a logistics company became Italy's first HVAC roll-up. Topics covered: 1. Buying "a little of everything" to share workforce across heating and AC seasons 2. Fixing a €2M loss in France, then selling it to chase a better opportunity 3. Why word-of-mouth deal flow beats cold outreach 4. The one integration non-negotiable: ERP on day one 5. Paying technicians 30-40% above average to retain them RolyPoly is the podcast about all things roll-up. New episodes every Tuesday. Connect: pmistack.com [http://pmistack.com] | linkedin.com/in/dylan-harrocks [http://linkedin.com/in/dylan-harrocks]

Ryan Imison: £700M Platform on Acquiring Services Your Clients Already Need

Network Plus is a £700M+ UK utilities contractor that acquires complementary services — fencing, vegetation, wastewater — and cross-sells them into the clients they already serve. Ryan Imison (Head of M&A, Network Plus) joins Dylan to talk about what integration actually looks like when you're adding new capabilities to an existing platform — from onboarding 300 people overnight to sending executives on-site with an open door for weeks. Topics covered: 1. Why Network Plus acquires new services instead of building them internally 2. The mobilisation advantage — how winning contracts gives you integration practice 3. Drop-in sessions: the simple tactic that builds trust with acquired teams 4. Why something will always go wrong and how fast you react matters more than the plan 5. First-time acquirer advice: be deliberate or run around like a headless chicken RolyPoly is the podcast about all things roll-up. New episodes every Tuesday. Connect: pmistack.com [http://pmistack.com] | linkedin.com/in/dylan-harrocks [http://linkedin.com/in/dylan-harrocks]