M&A Science

Matt James, EVP, CFO & Chief Acquisition Officer at Oakbridge Insurance
Roll-up platforms that skipped real integration are getting exposed when they go to market. Buyers want proof of organic growth, clean data, and a platform that actually functions as one. A lot of processes are breaking down because those proof points aren't there.
Matt James co-founded Oak Bridge Insurance in 2020 and has since closed 60+ acquisitions, integrating 100% from day of close. This conversation covers how he built that system, what went wrong with billion-dollar competitors, and what he would fix first if he walked into a revenue-aggregating roll-up right now.
 What You'll Learn
Why multiple arbitrage is gone, and what buyers are scrutinizing instead
How Oak Bridge evaluates cultural fit before any financial criteria
What a failed billion-dollar roll-up sale process looks like from the inside
Building integration continuity from LOI through 90 days post-close
How distributed equity drives buy-in across an acquired organization 

If you're evaluating targets and want to know if they're integration-ready pre-LOI, the Intelligence Hub can help you score cultural fit, data readiness, and technology maturity. Join the professional membership at  mascience.com/membership.
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This episode is sponsored by DealRoom
DealRoom's State of M&A Report gives you data to back up your M&A priorities.
The State of M&A Report reveals the gap between what teams think matters and where the real bottlenecks are.
Download it now to get expert insights: https://hubs.ly/Q03ZxRvD0
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Episode Chapters
[00:03:00]  Introduction & Matt's Background
[00:05:00] How Buyer Diligence Has Shifted
[00:06:00] Organic vs. Inorganic Growth and Why It Matters
[00:11:00] The Four-Criteria Deal Evaluation Framework
[00:14:00] Validating Cultural Fit Before LOI
[00:17:00] Deal Structure: Equity, Earnouts, and Alignment
[00:20:00] What Billion-Dollar Platforms Got Wrong
[00:26:00]Building the Integration System at Oak Bridge
[00:31:00] Bridging Diligence and Integration
[00:38:00] Data Infrastructure: Databricks, Power BI, and Why It's Worth It
[00:45:00] Building Proprietary Deal Flow
[00:52:00] First Moves When Integration Is Broken

Dan Caruso, Managing Director, Caruso Ventures; Founding CEO of Zayo Group
This is Part 2 of our conversation with Dan Caruso, founder and former CEO of Zayo Group. Be sure to start with Part 1. It covers the Zayo thesis, deal sourcing, structure, and the negotiation playbook, whereas this episode picks up at the execution.
Part 2 is about the equity value-creation framework Dan built at Zayo, applying the same IRR math PE firms use for their portfolio companies to daily operating decisions. It replaced budgets and tied every compensation decision to a single equation. It ends with the exit and how Dan put together a competing bid after a buyer consortium locked up the debt market.
What You'll Learn
How Zayo's integration process matured across 45 deals +  where it broke post- IPO
The equity value creation model: the IRR metric that replaced budgets and tied compensation to a single equation
Negotiation tactics: countering lower, manufacturing urgency, and splitting the CEO from their investor at the table
Culture during integration: one culture, take it or leave it
IRR compression as a sell signal and how Dan acted on it before most saw it coming
The sell process: engineering a competing bid after buyers locked up the debt market
The ICG deal: $8.7M in, $250M out, 18 months
Want to apply Dan's framework to your own business? The Intelligence Hub has the Equity Value Creation Operating Model, a step-by-step guide to replacing budget-based management with IRR as your operating compass. Access here. 
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This episode is sponsored by DealRoom
M&A Science is heading to ACG DealMax in Las Vegas, April 27–29 and we'd love to see you there. Stop by the booth for a book signing, swag, and a look at what the M&A Science and DealRoom teams have been building.
Learn more and save the date: https://hubs.ly/Q043VnNH0
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Episode Chapters
[00:02:28] Public company vs. private: what changed about deal execution.
[00:03:40] Negotiation tactics: countering lower, manufacturing urgency, the CEO-investor wedge. 
[00:08:15] Integration maturity: how execution evolved across 45+ deals.
[00:18:43] Culture: join us or don't. 
[00:20:35] Going public: super voting shares, activist investors, and the PR game Dan skipped. 
[00:24:40] Post-IPO talent drain and what Dan would restructure in management equity. 
[00:29:26] When to sell: reading value compression. 
[00:33:03] The sell process: competing bid against a cornered debt market.
[00:39:18] The equity value creation model: replacing budgets with IRR.
[00:43:29] IRR as a real-time operating metric. 
[00:49:50] Cruso Ventures, quantum, space, and Boulder Roots Music Fest.
[01:01:06] The ICG deal: $8.7M in, $250M out

Dan Caruso, Managing Director, Caruso Ventures; Founding CEO of Zayo Group
Dan Caruso built Zayo from a startup into a $14B+ 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.

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Episode Chapters
[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

Rodrigo Dominguez Sotomayor, Partner at White & Case LLP
Most US buyers approach Latin America M&A the same way they do a domestic deal — optimize the process, close fast, move on. That approach gets deals killed.
Rodrigo Dominguez Sotomayor, Partner at White & Case LLP, has spent 25 years closing transactions across every major Latin America market. In this episode, he walks through what actually determines outcomes: antitrust consent timelines, labor regimes that make post-close restructuring expensive, and the relationship dynamics that can unwind a billion-dollar deal a week before signing.
What You'll Learn In This Episode: 
How a PE fund lost a billion-dollar deal over 2% — and why it was avoidable
Why LatAm antitrust approvals can take up to nine months and how to plan around them
What no employment-at-will actually costs you post-close
Why showing up to a LatAm auction without reps & warranties insurance is a disadvantage
How to negotiate with family founders when price isn't what closes the deal
Why 80% of Latin America deals now run through auctions
Your standard diligence process will miss things that kill LatAm deals — statutory severance you didn't model, title searches that go back a hundred years, antitrust consent timelines that block close for months, auctions where R&W insurance is already expected.
Running diligence on a LatAm target right now? The M&A Science Hub has two resources built directly from this episode — the LATAM Diligence Delta Checklist and the Latin America M&A Entry Playbook — plus an AI tutor trained on 400+ practitioner conversations you can pressure-test your current deal against.
Members get access before the episode goes public. → Access inside the Intelligence Hub — members only. 
This episode is sponsored by DealRoom
Stop juggling six different tools to run one deal. DealRoom brings pipeline management, diligence tracking, document sharing, and team collaboration into one platform. Purpose-built for M&A teams who need to move fast without losing control. request your demo today: https://hubs.ly/Q03ZMvQX0
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Episode Chapters
[00:04:26] Rodrigo's background: 25 years across Latin America M&A
[00:06:57] How a cross-border acquisition actually starts
[00:10:17] Bilateral deals and family-owned businesses
[00:12:52] Reading the room: when not to push on numbers
[00:14:12] The billion-dollar deal that fell apart over 2%
[00:20:02] Antitrust consent regimes across LatAm
[00:29:49] The union leader story
[00:27:14] Labor, employment, and statutory severance
[00:34:04] Reps & warranties insurance: now standard in LatAm
[00:38:44] Auction vs. bilateral: the 80/20 split
[00:44:01] FinTech opportunity in Latin America
[00:48:05] NVCA forms and deal documentation
[00:52:48] Post-close integration: what actually determines success
[00:55:51] Craziest Thing in M&A

Chrissy Cox, VP & Head of Corporate Development, Booz Allen Hamilton
​​Booz Allen Hamilton didn't build one of the most active acquisition programs in federal tech by waiting for banker inbounds. They built it by showing up years before anyone else.
Chrissy Cox has built Booz Allen's corporate development function from scratch and done it twice. Her team was named Deal Team of the Year by the Association for Corporate Growth, and under her leadership, roughly 80% of their acquisitions come from companies they already have a relationship with. That's not luck, it's a system.
In this episode, she breaks down exactly how that system works — from pipeline development to cultural diligence to integration ownership — and what most corp dev teams get wrong before they ever get to LOI.
What You'll Learn in This Episode
How to build a proprietary pipeline that makes you the preferred buyer before a process starts
The specific cultural fit questions Chrissy asks — and the one answer that ended a deal on the spot
Why she tells founder-led sellers to hire their own banker, even on proprietary deals
How to navigate a carve-out when scope is impossible to fully define upfront
When spinning out a business beats building it internally
The three mistakes that derail most corp dev functions before they find their footing
This episode is sponsored by M&A Science Intelligence Hub
If you're trying  to move from cold outreach to genuine relationship-building with targets, the Intelligence Hub has the Partner-First Acquisition Evaluation Playbook — a practitioner-built framework for structuring pre-acquisition partnerships, evaluating targets through the lens of existing relationships, and moving from partner to acquirer with conviction. Become an M&A Scientist at www.mascience.com/membership 
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‍This episode is also sponsored by DealRoom‍
The best M&A teams close deals faster...not because they work harder, but because they have better systems. DealRoom helps you manage your entire deal lifecycle from target identification through close. No more hunting for documents or wondering what's blocking progress.
Request a Demo today: https://hubs.ly/Q03ZMvQX0
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Episode Chapters 
[00:00:00] Intro
[00:04:20] Chrissy Cox's path into M&A
[00:05:04] Building Booz Allen's corp dev function
[00:10:32] How Booz Allen builds a proprietary deal pipeline
[00:15:08] The partner-first approach to acquisitions
[00:20:31] When founders should consider selling
[00:23:49] Why culture can kill a great deal
[00:29:40] Carve-out lessons from the PAR Government deal
[00:33:24] Why founders should hire bankers
[00:43:43] Integration: protect the secret sauce
[00:48:01] The biggest mistakes in corporate development
[00:49:33] The craziest thing about M&A