Selling Your Business with Confidence

A comprehensive handbook for middle-market business sellers

In Selling Your Business with Confidence: A Practical Playbook for Mid-Market Owners, veteran M&A advisor David McCombie delivers an insider's guide to navigating the mergers and acquisitions (M&A) sales process. In plain English, this book covers every essential topic for owners considering the sale of their business. Readers will fully understand the process, the range of options available, and their implications.

In the book, you'll learn to navigate every step of the exciting—yet stressful—business sale journey, such as:

• The overall timeline, mechanics, and typical strategies of a deal
• Understanding different types of buyers and what they prioritize
• Tactics you can implement immediately to make your company more valuable
• Strategies for emotionally and psychologically preparing yourself for the transaction

An essential roadmap to the complicated world of mid-market M&A transactions, Selling Your Business with Confidence is a must-have resource for business owners and the ecosystem of professionals who serve them.

Introduction 1

Chapter 1 The Art and Science of Selling a Company 5

Chapter 2 What’s My Business Worth? 13

Chapter 3 What Are We Multiplying By? 21

Chapter 4 Picking the Right Time to Sell 31

Chapter 5 No Learning on the Job 41

Chapter 6 M&A Is a Team Sport 57

Chapter 7 Who’s Going to Buy My Business? 63

Chapter 8 The Siren Call of the Unsolicited Offer 73

Chapter 9 What Does a Buyer Want? 79

Chapter 10 Choosing the Right Transaction Type 89

Chapter 11 Bad News 95

Chapter 12 Reverse Engineering Your Business 101

Chapter 13 The Art of Selling 109

Chapter 14 Negotiating Strategy 115

Chapter 15 Overcoming Inertia 127

Chapter 16 Documents and Deal Process 135

Chapter 17 Tailoring the Process 143

Chapter 18 Keeping the Secret 153

Chapter 19 It’s a Process 161

Chapter 20 Seeing Where You Stand 169

Chapter 21 Purchase Price and Terms 177

Chapter 22 Negotiating and Signing the Letter of Intent 189

Chapter 23 Playing Defense 203

Chapter 24 Legal Documentation and Critical Elements 213

Chapter 25 Closing Craziness 221

Chapter 26 Managing Your Emotions and Psychology 225

Postscript 235

Acknowledgments 237

About the Author 239

Glossary 241

Bibliography 245

Index 247

DAVID W. McCOMBIE III is the Founder and CEO of McCombie Group, an M&A advisory firm that improves, grows, and sells mid-market companies. A veteran dealmaker, he has personally negotiated billions in transaction value and has been recognized for setting record valuations. Unique among advisors, he is a passionate entrepreneur and has also successfully led various private equity investments himself. He is a graduate of Harvard Law School and the University of Miami.

I know you have plenty of pressing matters on your plate. However, there’s no better investment of your time than reading this book. Applying its lessons can yield not just (tens of) millions of dollars more, but the peace of mind associated with a smoother, less stressful sales process.

Systematically preparing your business for an optimal exit will lead to a dramatically higher sale price, and allow you to sell from a position of strength, on your own terms and timeline. Whether you want to sell now or someday, it’s never too late to get started.

So, what exactly will you learn by reading this book?

• Overall timeline, mechanics, and common strategies of a deal
• Reasoning behind important elements of the process
• Framework for determining the optimal time to sell
• Roles and expectations of various deal team members, expected fees, and how to prioritize selecting them
• Key questions to ask to make informed decisions
• Understanding the buyer’s perspective and their typical strategies
• Negotiation tactics and the underlying psychology behind them
• Interpreting and comparing offers
• Preparing yourself psychologically for this challenging process
• Steps you can take today to improve the value and sellability of your business

Level the playing field against professional buyers

As an entrepreneur myself, I understand firsthand the relentless effort required to build a successful business. Your company is not just an asset—it’s your life’s work, often representing 80-90% of your total net worth. Selling it is a monumental decision that can dramatically impact your financial future, personal satisfaction, and legacy. The stakes could not be higher.

For most owners, selling a business is a once-in-a-lifetime event. However, your buyer and their advisors will be seasoned professionals who have done this hundreds of times and will leverage every possible advantage. This is not the time to learn through trial and error.

For middle-market owners, selling is not just a financial transaction but a deeply personal and emotional journey. Unfortunately, most owners find themselves unprepared, underestimating the time, money, effort, and complexity involved. Because of the many “unknown unknowns,” the sale process becomes an exhausting psychological roller coaster. But with the right knowledge, you can confidently navigate the process and make the best decisions.

Drawing from his decades of experience negotiating billions in deals, David McCombie shares his insights regarding both the art and science of selling a mid-market company. This book offers straightforward guidance—free of academic theories and legal jargon—to support you through one of the biggest decisions of your life.