Insights

Most M&A deals don’t fall apart in one moment. They leak value at a dozen decision points between the first conversation and the wire. This series, drawn from my Founders’ Series webinar, takes those pitfalls one at a time, from the first buyer conversation to life after closing.

Start here

• Everything That Goes Wrong in an M&A Deal, and Six Ways to Avoid Most of It

  The four stages where M&A deals leak value, and the six imperatives that separate clean exits from the ones that bleed value between the LOI and the wire.

Before the LOI

• Your Number and the Buyer’s Number Are Never Close

  Why the buyer’s number and the seller’s number start far apart, the four ways valuations diverge before the LOI, and why to anchor to the market median.

• Tension Is Leverage: Run a Process, and Read Your Banker’s Engagement Letter

  Why bilateral deals close 10% to 30% below a competitive process, how to choose an M&A banker, and the engagement letter terms worth negotiating.

• Fix Your Cap Table Before the Buyer Reads It

  Six cap table problems to fix before the LOI: dead equity, 409A history, undocumented grants, drag-along mechanics, consents and the option pool.

• Your Investors Aren’t on Your Side of the Table

  Why your investors’ interests diverge from yours in a sale, from liquidation preferences to appraisal rights, and how options, SAFEs and pools really pay out.

• Asset Deal or Equity Deal: The Fork That Decides Who Pays

  Asset deal or equity deal: who carries the historical risk, who gets the tax step-up, and why C-corp sellers need to model both structures before the LOI.

• QSBS: The Founder Tax Break Most Often Lost at Signing

  How Section 1202 works, the five eligibility gates, the new tiered holding periods, Section 1045 rollovers and the states that don’t follow QSBS.

• What Olaplex v. L’Oréal Teaches About Sharing Secrets With a Buyer

  Olaplex v. L’Oréal, TAOS v. Intersil and Propel v. Phillips 66 show what protects a seller’s trade secrets when a buyer walks away from a deal.

• Buyers Price Uncertainty

  Six credibility mistakes that cost sellers money, why deal momentum matters, and the diligence findings that move price, including customer concentration.

• The LOI Is the Last Moment You Have Full Leverage

  Why the letter of intent is a seller’s last moment of full leverage, and the terms to settle or frame before exclusivity flips it to the buyer.

Diligence and documents

• Indemnification in the Age of R&W Insurance

  Caps, baskets, survival and sandbagging in 2025 deals, how R&W insurance rewrote the seller’s indemnity, and what the policy won’t cover.

• Disclosure Schedules Are a Structured Confession

  How disclosure schedules soften a seller’s reps, and the three battlegrounds: cross-application, bring-down updates and drafting discipline.

Signing to closing

• Signing Is Not Closing

  Between signing and closing: MAE and walk rights, operating covenants, gun-jumping, the bring-down and the third-party consents that stall deals.

• Regulatory Approvals and Who Pays for the Wait

  HSR, CFIUS and foreign investment reviews, plus the outside dates, ticking fees, efforts standards and reverse termination fees that decide who pays for the wait.

After closing

• After the Wire Clears

  Earnout disputes, rollover handcuffs, non-competes and the working capital true-up: where value is lost after an M&A deal closes.

• After Closing, the Contract Is Your Only Recovery Path

  After closing, the purchase agreement is the only recovery path: indemnity claims, the tax indemnity and choosing the Stockholder Representative.