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

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 | linkedin.com/in/dylan-harrocks

Network Plus is a £585M 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

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

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

Sam Turner's first acquisition went to zero. Here's how he rebuilt a £30M portfolio — self-funded, no PE.

Sam Turner (Founder & Group CEO, Advantos Group) joins Dylan to discuss roll-up integration strategy, self-funding acquisitions, and what most operators miss in due diligence.

Topics covered:

1. Why keeping acquired businesses separate failed
2. The first acquisition disaster and what it taught him
3. Due diligence on people and culture vs financials
4. Building without institutional capital
5. Hiring the people who change everything

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

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

Roll-ups don't fail because of bad deals. They fail because finance can't keep up.

Pavleta Pavlova (Founder & CEO, PPHF) joins Dylan to discuss what actually breaks in a roll-up's finance function — and how to fix it before audit season.

Topics covered:

1. The most expensive mistake: not standardizing your chart of accounts early
2. Why a fractional CFO should start 30 days before your first deal closes
3. The 30-60-90 day financial integration framework
4. When to move from Xero/QuickBooks to an ERP
5. Handling change resistance in acquired finance teams

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

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

87% of deal failures are cultural. So why does nobody measure it before closing?

Simone Vascotto (Founder, Humanaq) joins Dylan to discuss why M&A culture assessments are broken — and how AI-powered behavioral analysis is changing the game for acquirers and roll-ups.

Topics covered:

1. The invisible culture that kills deals — and how to surface it
2. Why "assuming" is the #1 post-merger integration mistake
3. How five open-ended questions can reveal execution risk in under 10 days
4. The tea tray story: a small cultural symbol that triggered a company-wide revolt
5. When cultural due diligence matters — and when it doesn't
6. Cross-border culture clashes and how to navigate them

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

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