Finding Win-Win Deals Versus Stock-Picking

Dan Caruso, Managing Director, Caruso Ventures; Founding CEO of Zayo Group

Dan Caruso built Zayo from a startup into an $8.5B bandwidth infrastructure platform through 45 acquisitions. In Part 1, he walks through the full buyer-led playbook — how the thesis was built on a contrarian bet that everyone else got wrong, how proprietary deals were sourced through early relationship-building, and why fast integration wasn't a reputation problem — it was a competitive advantage.

He also breaks down the metric trap most roll-up operators fall into: mistaking EBITDA growth for true value creation. If your board is tracking acquisitions individually or your deal structure is loaded with earnouts, this conversation will challenge how you're running the program.

What you'll learn:

• How to identify and build a contrarian acquisition thesis with investor alignment
• Why proprietary deal flow is a brand and relationship problem, not a sourcing problem
• How Zayo executed an unsolicited, fully funded offer on a larger public company — and won
• Why tracking individual acquisitions kills synergies in a roll-up
• When earnouts hurt more than they help — and what to use instead
• How clean, all-cash offers win on certainty, not price

Dan's approach to thesis validation, investor alignment, and platform value creation is documented in the Roll-Up Readiness Assessment inside the Intelligence Hub, a stage-gated guide built directly from this conversation. Access inside the Intelligence Hub — → Access inside the M&A Science Hub — members only.

This episode of M&A Science is presented by DealRoom. DealRoom just automated Pipeline Management with AI so you can spend less time updating deals, and more time working them. Automatically push deal context from Outlook to DealRoom Pipeline and use AI to keep deal target data and tasks updated, so follow-ups never slip through the cracks. No manual logging. No stale pipeline data. See for yourself: https://hubs.ly/Q045fXp50

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[00:02:00] Introduction: Dan Caruso and the Zayo Story

[00:03:51] Background: From Ma Bell to MFS to Level Three

[00:08:58] Lessons from WorldCom: What Fake Value Creation Looks Like

[00:10:35] What First-Time Acquirers Get Wrong

[00:12:39] Building the Zayo Thesis: Fiber Orphans and Accidental Owners

[00:17:20] Raising Capital When You Have a Track Record

[00:23:50] What Must Be True for the Thesis to Work

[00:26:54] Why EBITDA Doesn't Measure Value Creation

[00:29:15] The Danger of Tracking Acquisitions Individually

[00:31:17] What Actually Drove Zayo's Success

[00:36:10] Convincing Sellers: Proprietary Sourcing and Relationship Strategy

[00:45:30] The Above Net Acquisition: Unsolicited, Fully Funded, at a Conference

[00:51:02] Negotiation Tactics: Unpredictability, Silence, and Team Play

[01:02:16] Deal Structure: Why Zayo Avoided Earnouts

[01:03:56] Clean Cash Offers and Certainty of Close