Rule 1
Buyers pay for future cash flow, not past effort.
Chapter 1 · The Hidden Reality of Selling a BusinessIsn’t selling my business like selling anything else?
A field guide to selling a privately held company
Most owners walk in blind.The buyer never does.
Maximizing Value, Preserving Legacy, and Selling Your Business on Your Terms
Brent Engelbrekt, author
- CBI of the Year, 2021 and 2024
- Managing Director, True North Mergers & Acquisitions
- Transactions above $100 million
From Chapter 1
An owner hears ten million. Here is what reaches the wire.
The customer concentration gets repriced, the add-backs get knocked out in diligence, a piece is carved into an earnout, a piece is rolled forward, and a piece sits in escrow. Brent opens the book with this example because everything after it depends on understanding the gap.
How a $10M headline becomes $4.5M at close
- Headline and cash at close
- Price actually came down
- Deferred or at risk
Illustrative, not your deal. Where the book uses dollar figures, they are there to show how something works, not to describe your business. Your banker, your accountant, and your attorney will put real numbers to your own situation. Full note.
Inside the book
Built to be used, not read once.
It is organized around the real questions owners ask when they sell, the ones they say out loud and the ones they do not yet know to ask. Each chapter is titled with its topic, and underneath it is the owner question that chapter answers. You can read the book straight through and follow the arc of a sale from first thought to final wire, or you can open to the one chapter you need right now and get a complete answer without having read the nine chapters before it. Each chapter stands on its own and points you to the others when they are relevant.
Part 1
Before You Go to Market
The work that decides your number before a single buyer sees the business.
- 1Isn’t selling my business like selling anything else?
- 2What is the buyer across the table really thinking?
- 3What is my business actually worth?
- 4Should I wait one more year to sell?
- 5Why would I pay to audit my own numbers?
- 6My books are fine. Why isn’t that enough?
- 7What will a buyer use to chip at my price?
- 8Can my business run without me?
- 9How much of the sale do I actually keep?
Part 2
Going to Market
Assembling the team, the buyers, and the story that create competition.
Part 3
The Live Process
What actually happens once your business is in front of buyers.
- 15How do I sell without word getting out?
- 16How do I handle the flood of buyer questions?
- 17What do the first offers really tell me?
- 18How do I handle the meeting where buyers size me up?
- 19What am I really signing when I sign the LOI?
- 20Why is the period right after signing so dangerous?
- 21What happens when the buyer looks under every rock?
Part 4
The Deal Terms
Where the price you agreed to becomes the money you keep.
- 22What am I actually agreeing to in the final contracts?
- 23Should I sell the assets or the stock?
- 24Why does the buyer want a 338(h)(10), and what does it cost me?
- 25What is an F reorg, and whose benefit is it?
- 26What is a 754 election, and should it be on the table?
- 27How much cash do I actually walk away with?
- 28How much of the price is really at risk after closing?
- 29What can still go wrong at the closing table?
Part 5
Structure and the Money
The parts of your price that arrive later, if they arrive at all.
Part 6
After the Close
The part nobody prepares you for.
About the book
The Seller’s Playbook
Maximizing Value, Preserving Legacy, and Selling Your Business on Your Terms
For most owners, selling their business is the one deal they will ever run, and the buyer across the table has run dozens. That imbalance shapes everything that follows.
The Seller’s Playbook is the field guide to what actually happens once a company goes to market: how buyers think, what drives your price, where the leverage sits, and how the money really gets divided at the close. It is the part every other exit book skips.
Built as a reference, not a lecture, it moves the way your deal will: from the first buyer call, through valuation, diligence, and negotiation, to the wire that clears and the life that starts after it. Each chapter answers one question owners actually ask, and each ends with a single rule worth carrying into the room.
Brent Engelbrekt, Author
He is a Managing Director at True North Mergers & Acquisitions, twice named CBI of the Year, and he has sold a company of his own. 34 rules, read about the author.
What you will learn
Ten things this book will teach you.
- How buyers really think, and why the flattering call you got was a screen, not a discovery.Chapter 2: How Buyers Really Think
- What your business is actually worth, and why it is not the number in your head.Chapter 3: What Drives Value, and What Doesn’t
- Whether to wait one more year to sell, and what that year really costs.Chapter 4: Why Timing Matters More Than You Think
- Why you should pay to audit your own numbers before a buyer does it for you.Chapter 5: The Sell-Side Quality of Earnings
- What you are really signing when you sign the letter of intent.Chapter 19: Final Bids and Letters of Intent (LOIs)
- Why the stretch right after signing is the most dangerous part of the whole deal.Chapter 20: Exclusivity
- How much of the price is still at risk after closing, and how to hold on to it.Chapter 28: Escrows, Indemnification, and Post-Closing Risk
- Whether you will ever actually see the earnout money.Chapter 30: Earnouts
- How much of the sale you actually keep after tax, and what to do about it before you sign.Chapter 9: Pre-Sale Tax and Estate Planning
- Who you are, and what you do, the morning after the business is gone.Final Chapter: Life and Identity After the Sale
The Seller’s Rules · with Brent Engelbrekt
One rule per chapter. Thirty-four worth carrying into the room.
Every chapter ends on a single idea worth remembering, a plain rule drawn from Brent’s years across the table. All of those rules are collected in one place in the back of the book, so you can read them on their own as a quick map of everything that matters.
Rule 3
Proven earnings create value; potential only supports the story.
Chapter 3 · What Drives Value, and What Doesn’tWhat is my business actually worth?
Rule 5
Find your own problems before the buyer finds them.
Chapter 5 · The Sell-Side Quality of EarningsWhy would I pay to audit my own numbers?
Rule 19
Most of your leverage disappears the moment exclusivity begins.
Chapter 19 · Final Bids and Letters of Intent (LOIs)What am I really signing when I sign the LOI?
Rule 20
Protect your leverage even after selecting a buyer.
Chapter 20 · ExclusivityWhy is the period right after signing so dangerous?
Rule 28
The deal is only worth what you ultimately keep.
Chapter 28 · Escrows, Indemnification, and Post-Closing RiskHow much of the price is really at risk after closing?
Rule 30
Hope is not a collection strategy.
Chapter 30 · EarnoutsWill I ever actually see the earnout money?
The Final Rule
A successful exit is not the end of the story. It is the beginning of a new one.
Final Chapter · Life and Identity After the SaleWho am I, and what do I do, once the business is gone?
What AI Changes Here · with Dena Neek
What AI has changed about how a company is bought and sold. And what it has not.
Thirteen short sections run through the book. Each one takes a chapter you have just read and says what buyers now do with AI, and the two or three decisions that fall out of it for you. Buyers screen continuously, read everything, and price what they find. The rules of the deal did not change. The speed and the depth did.
Chapter 2 · How Buyers Really Think
That flattering call was a list, not a discovery
The buyer is still asking how much risk are we taking on. They are just asking it earlier now, and often before you know the conversation has started.
Chapter 19 · Final Bids and Letters of Intent (LOIs)
You can look up how this buyer behaves before you hand them exclusivity
The document is still a preview of the person. The difference now is that you can check the preview against their record.
Chapter 27 · Working Capital
The side with the better analysis sets the peg
Working capital is economics, not accounting. The side that shows up with the better analysis sets the peg, and which side that is gets decided a year before anyone asks you about it.
Dena Neek, Technology and AI
She has been applying AI to business outcomes since 2018, first while running teams across multiple business groups, now at ExBrain. Read about the contributor.
Step 1
Pre-order the book.
Brent Engelbrekt with Dena Neek. Hardcover, six parts, 34 chapters, and every Seller’s Rule collected in the back.
- AmazonComing soon
- Barnes & NobleComing soon
- Bookshop.orgComing soon
- Books-A-MillionComing soon
- TargetComing soon
- WalmartComing soon
- Apple BooksComing soon
- AudibleComing soon
Retailer links go live the day the book is available for pre-order.
Be told the day pre-orders open
Step 2
Reader bonuses arrive at launch: the Seller’s Rules as a poster, the pre-market readiness checklist, and the glossary as a pocket card. Until then, Chapter 1 is below.
The people behind the book
Know the whole path before you take the first step.
Brent Engelbrekt
CBI, M&AMI, CM&AP, CEPA · Managing Director, True North Mergers & Acquisitions
Brent Engelbrekt, CBI, M&AMI, CM&AP, CEPA, is a Managing Director at True North Mergers & Acquisitions, where he advises owners of privately held companies on the sale of their businesses. He has guided entrepreneurs through one of the most important financial and personal decisions of their lives: the sale of a company. Brent lives in Minnesota and works with business owners throughout the United States.
He wrote this book because the owners he works with kept asking the same questions, sometimes too late, and there was nowhere to send them for straight answers about what actually happens once a business goes to market.
Dena Neek
Technology and AI · Co-founder and CEO, ExBrain
She is an AI engineer and entrepreneur who has built and sold three technology companies and now designs AI-native systems for operating businesses. In this book she owns a single question: what has AI changed about how a company is analyzed, valued, and bought, and what should an owner do about it before going to market. The deal is Brent’s territory. The technology is hers.
Dena is co-founder and CEO of ExBrain, an AI platform built for the moment every buyer dreads: the founder leaves after close and the business stops working, because everything that made it work was in their head. ExBrain learns how the business actually runs and keeps it running without them. Her latest venture received Judges’ Choice at the 2024 AI Innovation Summit and was selected by the U.S. Department of Commerce as one of twelve startups representing American innovation at CES 2025.
Get Chapter 1
The number you hear is not the number that lands.
The full first chapter, the waterfall, and Rule 1, as a PDF.