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RolyPoly

RolyPoly

By: Dylan Harrocks
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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.Copyright 2026 Dylan Harrocks Economics Personal Finance
Episodes
  • Nicholas De Poorter on Deal Structures: Earnouts, Equity & Rollover
    Jun 30 2026

    Most PE funds pick a sector then hunt for companies. Strada Partners flipped it: they back the team first, then build the roll-up.

    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.

    Topics covered:

    • Why Strada backs teams with a thesis, not deals

    • Lighthouse deals vs carpet bombing on the first acquisition

    • Deal structures: equity, rollover, vendor loans and the earnout trap

    • The two-bucket AI framework and inverting the AI-native roll-up

    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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    51 mins
  • Mac Lackey on Selling 6 Companies: Be Irresistible to Buyers
    Jun 9 2026

    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.

    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.

    Topics covered:

    • Why AI today is the early internet of 1995

    • The integration mistake that emptied a billion-dollar IPO

    • Strategic value vs. EBITDA multiples

    • The founder's paradox and how to escape the critical path

    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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    45 mins
  • Sam Hields: What Investors Look for In Roll-Up Founders
    May 12 2026

    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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    1 hr and 4 mins
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