Navigating the Risks of Selling a Company

How do founders and finance leaders prepare for the sale of their company when the other side of the negotiating table does this every day? In this episode, CJ interviews David Siegel, Partner at Grellas Shah LLP, a Silicon Valley law firm that guides some of the biggest names in tech through their most significant raises and exits. David shares insights from countless deals, revealing what it really takes to prepare for a sale, negotiate with buyers, and manage conflicting advice from bankers and lawyers. He unpacks investor dynamics, deal timelines, and why the $150 million to $350 million valuation range is the “awkward middle.” The conversation also covers how companies can de-risk themselves before going to market, how to spot a bad banker, what critical pitfalls to avoid in Letters of Intent (LOIs), the emotional realities founders face when selling their “baby,” and the shifting power dynamics in today’s M&A landscape.

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LINKS:

David Siegel: https://www.linkedin.com/in/david-siegel-a271265

Grellas Shah:

https://grellas.com

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

Mostly metrics:

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TIMESTAMPS:

(00:00) Preview and Intro

(02:06) Sponsor – Brex | Aleph | RightRev

(06:41) The Average Time To Close M&A Deals Today

(10:55) How To Start the Process of Selling a Company

(13:09) Being Realistic About Your Valuation

(15:13) Sponsor – Navan | Rillet | Pulley

(19:08) VCs Versus Acquirers

(20:12) The $150 Million to $350 Million Valuation Awkward Middle

(23:17) Investor Behavior and Founder Incentives in Deals

(24:59) The Banker Versus Relationship Route in Selling

(27:46) What Makes a Bad Banker

(28:43) PSA: Investment Banker Engagement Letters Are Negotiable

(34:43) LOIs: What Sellers Should Push To Include Before Signing

(39:43) What To Prioritise as a CFO in an LOI

(43:21) The Worst Case Scenario for Vague Networking Capital Targets

(46:22) De-Risking Your Company in the Eyes of an Acquirer

(49:17) How Acquirer Risk Aversion Derails Deals

(52:07) The Emotional Impact of Selling a Company

(55:32) The Rules of Negotiation

(57:19) Current State of M&A in Tech

(1:01:30) Wrap

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#TechAcquisitions #AcquisitionLaw #StartupExit #MergersAndAcquisitions #ExitStrategy

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