Don’t Sign That Yet: Small M&A Mistakes That Can Cost You Big

M&A deals usually involve a vast amount of legal fine print, and small oversights can have very costly consequences. To help you navigate this, CJ is joined in this episode by Trey O'Callaghan, a partner in Tech, M&A, and Emerging Companies at Goodwin. Trey breaks down the strategic role M&A lawyers play throughout the deal process in terms of both legal and business advice to help avoid costly missteps. The conversation explores when to involve legal counsel, issues like sales tax and contractor classification, and common deal-killers such as IP ownership and unresolved co-founder disputes. Trey also explains why earn-outs are the most litigated part of M&A deals and how to handle them wisely. The discussion touches on the personal implications of M&A deals for CFOs and how to negotiate adequate compensation. Trey also covers non-compete and non-solicit agreements, and the importance of understanding working capital fluctuations.

—

LINKS:

Trey O’Callaghan on LinkedIn: https://www.linkedin.com/in/trey-o-callaghan-3196896a/

Goodwin:

https://www.goodwinlaw.com/

CJ on X (@cjgustafson222): https://x.com/cjgustafson222

Mostly metrics:

http://mostlymetrics.com

—

TIMESTAMPS:

(00:00) Preview and Intro

(02:12) Sponsor – Navan | NetSuite | Pulley

(06:55) The Types of Law Trey Specialises In

(10:08) When a Company Should Engage With an M&A Lawyer

(16:52) Sponsor – Brex | Aleph | RightRev

(21:24) Deals That Have Fallen Apart

(24:15) Unpaid Sales Tax as a Common, Solvable Issue

(25:27) Issues With Contractors and How To Solve Them

(27:08) Problems With IP Ownership

(28:37) Co-Founder Issues

(29:43) The Most Litigated Part of M&A Deals: Earn-Outs

(34:30) Choosing the Right Plan To Use To Sell the Company

(37:11) Deal Fatigue

(38:36) The TLDR on Earn-Outs

(39:57) The Ideal Mindset for the CFO During the Deal Process

(42:33) When and How To Negotiate Compensation as a CFO

(47:55) Understanding Working Capital Fluctuations

(52:25) Non-Competes: How They Work

(56:34) Considerations for Non-Solicits

(59:51) Closing Words for Anyone Doing an M&A Deal

—

SPONSORS:

Navan is the all-in-one travel and expense solution that helps finance teams streamline reconciliation, enforce policies automatically, and gain real-time visibility. It connects to your existing cards and makes closing the books faster and smarter. Visit navan.com/Runthenumbers for your demo.

NetSuite is an AI-powered business management suite, encompassing ERP/Financials, CRM, and ecommerce for more than 41,000 customers. If you're looking for an ERP, head to https://netsuite.com/metrics and get the CFO’s Guide to AI and Machine Learning.

Pulley is the cap table management platform built for CFOs and finance leaders who need reliable, audit-ready data and intuitive workflows, without the hidden fees or unreliable support. Switch in as little as 5 days and get 25% off your first year: pulley.com/mostlymetrics.

Brex offers the world's smartest corporate card on a full-stack global platform that is everything CFOs need to manage their finances on an elite level. Plus, they offer modern banking and treasury as well as intuitive expenses and accounting automation, bill pay, and travel. Find out more at brex.com/metrics

Aleph automates 90% of manual, error-prone busywork, so you can focus on the strategic work you were hired to do. Minimize busywork and maximize impact with the power of a web app, the flexibility of spreadsheets, and the magic of AI. Get a personalised demo at getaleph.com/run

RightRev automates the revenue recognition process from end to end, gives you real-time insights, and ensures ASC 606 / IFRS 15 compliance—all while closing books faster. For RevRec that auditors actually trust, visit rightrev.com and schedule a demo.

#MandA #MergersAndAcquisitions #MandALawyer #earnouts #CFO