Conversations with serial acquirers, investors, and specialists building roll-ups. Host Dylan Harrocks from PMI Stack digs into the real stuff - acquisitions that went wrong, integration nightmares, and the lessons that only come from doing. New episodes every other Tuesday.
RolyPoly
Claim This Podcastby Dylan Harrocks
10 episodes
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Podcast Overview
Conversations with serial acquirers, investors, and specialists building roll-ups. Host Dylan Harrocks from PMI Stack digs into the real stuff - acquisitions that went wrong, integration nightmares, and the lessons that only come from doing. New episodes every other Tuesday.
Language
🇺🇲
Publishing Since
3/6/2026
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Recent Episodes
June 30, 2026
Nicholas De Poorter on Deal Structures: Earnouts, Equity & Rollover
<p>Most PE funds pick a sector then hunt for companies. Strada Partners flipped it: they back the team first, then build the roll-up.</p><p></p><p>Nicholas De Poorter (investment team, Strada Partners) joins Dylan to break down how a Belgian PE fund runs 15 buy-and-build platforms across Europe.</p><p></p><p>Topics covered:</p><p>• Why Strada backs teams with a thesis, not deals</p><p>• Lighthouse deals vs carpet bombing on the first acquisition</p><p>• Deal structures: equity, rollover, vendor loans and the earnout trap</p><p>• The two-bucket AI framework and inverting the AI-native roll-up</p><p></p><p>RolyPoly is the podcast about all things roll-up. New episodes every Tuesday.</p><p></p><p>Connect: pmistack.com | linkedin.com/in/dylan-harrocks</p>
June 9, 2026
Mac Lackey on Selling 6 Companies: Be Irresistible to Buyers
<p>He sold 6 companies, watched a billion-dollar IPO walk out the door, and bought a 116-year-old Spanish football club. Mac Lackey on how to actually win an exit.</p><p>Mac Lackey (founder, Exit DNA) joins Dylan to discuss why most founders leave life-changing money on the table - and how to be irresistible to buyers.</p><p>Topics covered:</p><p>• Why AI today is the early internet of 1995</p><p>• The integration mistake that emptied a billion-dollar IPO</p><p>• Strategic value vs. EBITDA multiples</p><p>• The founder's paradox and how to escape the critical path</p><p>RolyPoly is the podcast about all things roll-up. New episodes every Tuesday.</p><p>Connect: pmistack.com | linkedin.com/in/dylan-harrocks</p>
May 12, 2026
Sam Hields: What Investors Look for In Roll-Up Founders
<p>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.</p><p>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.</p><p>Topics covered:</p><ul><li>Why services is a 10x bigger market than software</li><li>Front office vs back office automation (and why it matters)</li><li>Green flags, red flags, and "tourism" in AI roll-up pitches</li><li>Capital stack reality — equity, debt, and rollover equity</li><li>Where AI expands TAM (and where pricing collapses instead)</li></ul><br/><p>RolyPoly is the podcast about all things roll-up. New episodes every Tuesday.</p><p>Connect: <a href="http://pmistack.com" rel="noopener noreferrer" target="_blank">pmistack.com</a> | <a href="http://linkedin.com/in/dylan-harrocks" rel="noopener noreferrer" target="_blank">linkedin.com/in/dylan-harrocks</a></p>
10 total episodes available
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This podcast updates daily.
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