From Bootstrap Exit to $100M Roll-Up: The Rise of Edoardo Maggini

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The Deal Flow Show

Ivan Acuna

14 episodes

2 days ago

The Deal Flow Show is where private equity gets real. No scripted answers, no corporate fluff—just raw, unfiltered conversations with the top dealmakers in the game. We pull back the curtain on the industry, sharing the stories, strategies, and hard-earned lessons that you’d normally only hear behind closed doors. Whether you’re deep in the world of M&A or just starting to navigate private markets, this is where you get the insights, mentorship, and war stories that actually matter.

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From Bootstrap Exit to $100M Roll-Up: The Rise of Edoardo Maggini

The Deal Flow Show

1 hour 2 minutes 28 seconds

6 months ago

From Bootstrap Exit to $100M Roll-Up: The Rise of Edoardo Maggini

In this episode, Edoardo Maggini shares how he went from a 16-year-old Italian immigrant to building a $70M+ private equity roll-up in the coatings industry. He explains why he left the startup world behind, how his team is taking on giants like Sherwin-Williams, and what most entrepreneurs get wrong about building wealth. If you're thinking about buying businesses, building a portfolio, or competing with billion-dollar companies, this episode is a masterclass.For more content like this and an inside look into the world of the largest dealmakers in the world, subscribe to The Off Market Memo https://offmarketmemo.beehiiv.com/ Are you in Private Equity, VC, or a Family Office? Become a guest on the Deal Flow Show herehttps://guestlist.dealflowshow.ai/Timestamps:01:06 How Edoardo broke into ETA03:40 What StarStep Capital actually does05:27 Why they picked the coatings industry07:46 His immigration story + first business10:08 How he exited a startup in 3 years14:51 Advice he’d give his younger self15:55 Why “start from scratch” is overrated18:18 What most small business owners get wrong20:05 His step-by-step process for doing deals21:35 Why focusing on one industry matters22:26 How he thinks about building his team25:30 How his team splits roles without titles28:03 Why solo entrepreneurship doesn’t scale29:54 The hardest part after buying a company31:15 Why he loves keeping sellers' kids in place33:45 How they structure branding + integrations34:59 What long-term value creation looks like36:54 Their current size and 10-year goal38:47 How his Machiavelli mindset gives him an edge41:07 How he developed a big vision early43:21 “I don’t feel big… I feel like I’m just starting”44:42 Where he gets advice and mentorship47:24 The closest thing to a “bad deal” they’ve done48:45 Why proprietary deal flow is key50:26 Why bigger deals are actually easier53:22 What affects multiples in this space55:02 How they consistently win competitive bids57:57 Their long-term model vs. traditional PE59:26 Biggest lesson from 2025 (so far)