Vadim Rogovskiy on Why AI Makes Roll-Ups Unstoppable

In 2017 he cut his startup from 100 people to 50 and told his VCs the hypergrowth plan was over. Two acquisitions from the growth years, paid for with equity because the bank said no, became Tourism Software Group: an eight-company holdco that now funds deals from its own cash flow and keeps debt low on purpose.Philippe Willi (Group CEO, Tourism Software Group) joins Dylan to discuss going from VC-backed startup to Constellation-style roll-up.Topics covered: • Raising VC to be one of "the cool kids", and the churn problem that followed • Telling investors the hypergrowth plan was over • Funding acquisitions with equity, "the most stupid way you can do acquisitions" • Dinner with Mark Leonard, and what makes Constellation different • What TSG centralises (payments) and what it leaves to founders • Customer tiering, price normalisation and the Rule of 40RolyPoly is the podcast about all things roll-up. New episodes every Tuesday.Connect: pmistack.com | linkedin.com/in/dylan-harrocks

Most founders raising debt for the first time chase the cheapest facility. Wrong metric. In the lower mid-market, with hundreds of lenders and no two term sheets alike, it's the structure that makes or breaks a roll-up.Linus Eriksson Noren (Founder & CEO) and Resat Ozutok (Co-Founder & Partner, Tech Credit Partners) join Dylan to discuss how acquisition-driven companies actually raise debt, and when they shouldn't.Topics covered:• Why the lower mid-market is "a completely different beast" for debt• Structure beats price: 2.5x EBITDA can beat 3x depending on the definition• What lenders underwrite: the whole story is your borrowing base• When debt enters a buy-and-build, and the first-acquisition myth in Europe• The biggest mistakes: too early, wrong type, equity plan used as covenant caseRolyPoly is the podcast about all things roll-up. New episodes every Tuesday.Connect: pmistack.com | linkedin.com/in/dylan-harrocks

Everyone obsesses over which roll-up structure to pick. Alex Prokofjev says that's backwards, start with your own objectives, because investors back the person, not the idea.Alex Prokofjev (co-founder, RollUpEurope) joins Dylan to break down how to actually build a roll-up: choosing your model, raising capital, and avoiding the mistakes that quietly kill most of them.Topics covered:• Why to talk to investors now, not once you have the perfect thesis• The number one reason roll-ups fall apart• How much money you can really make from a roll-up• AI in roll-ups: Bending Spoons vs Team Shares, and the gunfight most founders don't see comingRolyPoly is the podcast about all things roll-up.Connect: pmistack.com | linkedin.com/in/dylan-harrocks

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-upRolyPoly is the podcast about all things roll-up. New episodes every Tuesday.Connect: pmistack.com | linkedin.com/in/dylan-harrocks

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 pathRolyPoly is the podcast about all things roll-up. New episodes every Tuesday.Connect: pmistack.com | linkedin.com/in/dylan-harrocks

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 softwareFront office vs back office automation (and why it matters)Green flags, red flags, and "tourism" in AI roll-up pitchesCapital stack reality — equity, debt, and rollover equityWhere 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 longHow EVE discovered $20M in hidden pipeline across client inboxesAI agents replacing operations teams (4 people to 1)The roll-up landscape: venture returns with PE risk profilesUsing AI for due diligence and founder outreach at scaleRolyPoly 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 businessesRolyPoly 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:Buying "a little of everything" to share workforce across heating and AC seasonsFixing a €2M loss in France, then selling it to chase a better opportunityWhy word-of-mouth deal flow beats cold outreachThe one integration non-negotiable: ERP on day onePaying technicians 30-40% above average to retain themRolyPoly is the podcast about all things roll-up. New episodes every Tuesday.Connect: pmistack.com | linkedin.com/in/dylan-harrocks

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:Why Network Plus acquires new services instead of building them internallyThe mobilisation advantage — how winning contracts gives you integration practiceDrop-in sessions: the simple tactic that builds trust with acquired teamsWhy something will always go wrong and how fast you react matters more than the planFirst-time acquirer advice: be deliberate or run around like a headless chickenRolyPoly is the podcast about all things roll-up. New episodes every Tuesday.Connect: pmistack.com | linkedin.com/in/dylan-harrocks