61 | What You Keep Is The Deal: The $30m Deal That Beat The $50m Deal
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If this was useful, the letter goes further: one short insider note each week on what I'm seeing in live deals right now. It's free, it's two minutes, and replies come straight to me. Join at thejmichael.com/letter.
What if the biggest number you can announce is not the one you get to keep?
Two founders sold their companies the same year, one for $50 million and one for $30 million, and the one who sold for less kept more in the bank. In this solo episode, J. Michael Fischer Jr., Managing Director at DBD Investment Bank, explains how that happens and why the headline number is not the deal.
Michael breaks down what comes off the top before a dollar reaches your account: cash versus paper, debt, fees, the working capital peg, escrow, and the one that matters most, taxes. Structure beats the headline, and the best time to act is long before a buyer shows up.
If a sale is anywhere on your horizon, this is the work most owners do too late. You don’t deposit a valuation. You deposit what survives. Listen now.
Timestamped Highlights[01:12] – Two founders, two exits, and why the one who sold for less kept more
[01:45] – The headline number is not the deal, and what actually is
[02:48] – Cash versus paper, and why $50 million is rarely $50 million
[03:28] – The first question to ask before you celebrate any offer
[04:08] – The working capital peg almost no founder sees coming
[04:47] – Escrow, holdbacks, and the insurance move that frees up your cash
[05:33] – Why structure matters more than the number on the front page
[06:21] – The tax trap that can hit the same dollars twice
[07:01] – Exactly where the $30 million founder won the exit
[09:34] – Why almost every lever is easier to pull before a deal exists
[10:20] – The allies to assemble, and the part most owners get wrong
[11:45] – The one question to sit with today if a sale is anywhere ahead
Important Links- Feel Fully Alive: The 5 Dimensions of Vitality gives you the framework to thrive. Get your copy here.
- Stay Ahead in Business: Michael shares strategies to boost your financial decisions. Read his latest blog.
- Grow Your Wealth: Book a call with DBD Investment Bank.
Going Beyond the Deal is an original podcast brought to you by J. Michael Fischer Jr. Production and editing by Podcast Your Brand.