The marketplace for small and midsize businesses is messy. Having peeked behind the curtain at over 10,000 companies, this book aims to demystify the buyers, the process, and the inevitably emotional journey that is selling a company. If you're reading this, you're likely an entrepreneur, a family member or close friend of a business owner, or an advisor to an owner. Great businesses outlast individual careers, including those of owners and founders. At some point, in some way, each business must be transitioned - years pass, people age, markets change, opportunities appear - as do challenges. Selling, whether it be a stake or the whole company, often carries an unfortunate amount of stress, anxiety, and frustration. Most of the time, selling is a once-in-a-lifetime occurrence, and the traditional paths are unnecessarily opaque. Do something enough and you get good at it. Just as you have built your expertise, my colleagues and I have had the privilege to peek behind the curtain at over 15,000 companies - reviewing financial statements, meeting with leadership, and seeking to understand what makes each company tick. Talking with hundreds of business owners, we noticed that many of the same questions, concerns, and thoughts repeat. And that makes sense. Just as all businesses share many commonalities, sellers of those businesses will have mostly similar experiences, with differences in personality, motivation, and situation driving the nuance. This book attempts to demystify deal-making from a seller's point of view. As much as the finance industry likes to pretend to be "buttoned up," investors and bankers are largely disorganized, and the process is unnecessarily shrouded in mystery. It's a messy marketplace, with every type, temperament, and motive imaginable. The goal of this book is to help sellers, the families of sellers, sellers' advisors, and company leadership to understand the market for smaller companies, allowing them to make better decisions and create better outcomes. Our hope is that you walk away from this book better prepared to understand the path forward, the vantage points of everyone involved, and the process of a transition through a transaction with an outside investor. This is the second edition of "The Messy Marketplace." When initially drafted in 2017, we had a little over 10 years under our belt. In the subsequent years, we've seen the marketplace and valuations continue to evolve, endured a pandemic, and made more than a dozen new investments. While most of the original text is intact, the updates underscore what's new or increasingly important when trying to successfully do a deal.