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The Messy Marketplace: Selling Your Business in a World of Imperfect Buyers
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.
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.
238 pages, Kindle Edition
Published September 10, 2024
76 people are currently reading
493 people want to read
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Displaying 1 - 18 of 18 reviews
May 26, 2019
I learned about this book via Twitter, where I started following Brent Beshore (before I knew he owns a private equity fund). I would highly recommend this book for business owners thinking about selling their business, since I am not aware of any other complete sources on this subject. It's also a good reference for advisors and buyers, although most of the content is quite basic. Easy to follow and always clearly explaining jargon, Beshore walks the reader through the more technical financial and legal aspects of a transaction as well as the inevitable emotional side of a deal. In addition, the book contains an extensive information request checklist to guide all parties involved through due diligence.
April 8, 2024
Building a deal team - "Ask intermediaries, lawyers, and accountants who they would use if they were in my position, then talk to the person that they recommend"
Places to look for brokers:
1. M&A source
2. AM&AA
3....
Vetting sellers - have they been thoughtful about who they would like to buy their business or do they just want the highest price?
Deal Structure - anything that can be measured can be tied to an earnout, the further down the line item on the income statement, the more likely it can be influenced by the buyer post acquisition
Ask what is the optimal asset structure (get rid of unnecessary cash, or add more assets, etc.) What is the optimal balance sheet for this asset?
Differentiation from PE buyers - PE will make significant changes to the business, also they often come in with hidden deal fees at the end to reduce the effective purchase price. They will retrade you.
Deal terms - a cap is a limit to the risk exposure for the seller, a basket is a minimum so that the seller doesn't have exposure to items under a certain amount. The seller may personally guarantee for the indemnification, however, there is no knowing that they will have the funds to follow through on that and forcing them to sell their home could be another issue.
Indemnification Insurance - if you don't trust the seller you could have them pay the premium for this. I don't know how hard this is to get or how long it would take.
Real Estate - if the real estate is strategic, because there's something important about the location to the success of the business, then you need to have a long term lease with a ROFR or you need to buy the real estate outright.
Deal Negotiation - what is a deal breaker to you? Don't lead with the best offer because then you're going to come off as obtuse when you refuse to change course. We are focused on the price and willing to give on the terms. We need to find a seller who really cares about the terms because I won't be able to offer the best price.
Legal documents - they come after the due diligence period, and take about a month of the exclusivity so know your timeline on due diligence. If something isn't specifically listed in an asset purchase agreement then it's not being sold.
Deal Addbacks - owner comp, personal expenses (it's really hard to verify what's necessary to the business and what's not and it's not on the buyer to do that. The seller needs to verify it, unless it's a small amount)
NDA agreements - go to see the template at www.aventur.es/mutual-nda/. He doesn't reccomend signing an NDA for something where you as a buyer do not have any involvement. (seller's agreement, compensation for the intermediary)
Seller Expecations - They should expect that buyers are going to ask them about failures and challenges in the business. Reasonable sellers expect these kinds of questions
Approach to search/lead generation - optimize for deal flow or optimize for % of LOI submission. If you want to optimize for LOI submission you need to get much more selective on the search. You can't tell a broker that you are looking for businesses selling below their worth, or that you are looking for a business with latent profitability levers that are easily exploited.
Killing deals - I haven't learned how to be quick at saying "no" yet. I can pass for cause or without reason. If I just don't have any interest in a deal then I can pass without reason, that worked with Jared. Otherwise pass for cause and leave the door open.
Broker interactions - killing quickly for rational reasons will build credibility and rapport with brokers. Ghosting them is easier, but will not build the relationship. I need to start selling myself and my background to the brokers so that they keep me in mind. If I have a reputation of being communicative, they will start to send me anything because they will know that I will look at anything.
Deal Process - you should have discussed a preliminary valuation prior to arranging a site visit. Otherwise you are potentially wasting a lot of your time and the seller's and the broker's time. They aren't going to be happy with you outside of that. During the site visit you have to be hyper focused on how often the owner's phone is going off. What kinds of things they are doing, what the day to day of what they are doing actually looks like.
KD implied that the LOI is a high threshold, where the qualitative aspects of the business need to be well understood. Due diligence is just about verification of the things that you've already asserted. It could be helpful to assert those things to investors and see how they react to them. I can use David Sachs and John Sedgewick as sounding boards for myself.
IOI/LOI strategy - some brokers will pick up on my throwing in LOIs that aren't that detailed and view it as a negative. I do want to be aggressive about moving the deal forward, but I don't want to be so aggressive and careless that it starts to hurt my reputation.
Buyer comfort with ambiguity and processing information goes up the smaller the transaction gets.
April 11, 2019
The Messy Marketplace is a compact, step-by-step guide to selling a small- or medium-sized business that I believe is essential reading for any business owner beginning to contemplate selling their business, or aspiring small business owner-operators (or search fund operators) looking to buy a business.
As the title suggests, the world of small and medium-sized business is not subject to the “neat” standard operating procedures that govern the corporate world. As a result, a guide like the Messy Marketplace is invaluable in breaking down exactly what to except from all stages of the sale process – from deciding to sell to the deal’s closing – even touching with “seller’s remorse” and other similar maladies drawing on his vast professional experience.
Brent is unflinchingly honest about the misalignments in communication, expectation, price, and seemingly every facet of the sale process that can take place between buyer and seller, and writes from a place of comprehension, empathy, and experience. As the book explains, while the process may not be altogether painless, the Messy Marketplace will ensure that you will go into the process fully aware of the experience to come.
One of the best parts of the book is its ‘egoless,’ straightforward approach to the process – have you ever held back on asking a question or clarification for fear of looking (gasp) stupid or uninformed? Of course, we all have. The book seeks to disambiguate the investment world’s seemingly secret world of concepts, terms, acronyms, and abbreviations. There’s even a handy glossary in the back, to quickly consult if needed!
Brent’s firm, adventur.es has long distinguished itself for its commitment to operating from a place of honesty, integrity, and a community-oriented mindset. The Messy Marketplace is no exception.
The Messy Marketplace is a book that I plan to consult often in my career, and believe will save me no shortage of money, time, and confusion down the road. Thank you to Brent & team!
As the title suggests, the world of small and medium-sized business is not subject to the “neat” standard operating procedures that govern the corporate world. As a result, a guide like the Messy Marketplace is invaluable in breaking down exactly what to except from all stages of the sale process – from deciding to sell to the deal’s closing – even touching with “seller’s remorse” and other similar maladies drawing on his vast professional experience.
Brent is unflinchingly honest about the misalignments in communication, expectation, price, and seemingly every facet of the sale process that can take place between buyer and seller, and writes from a place of comprehension, empathy, and experience. As the book explains, while the process may not be altogether painless, the Messy Marketplace will ensure that you will go into the process fully aware of the experience to come.
One of the best parts of the book is its ‘egoless,’ straightforward approach to the process – have you ever held back on asking a question or clarification for fear of looking (gasp) stupid or uninformed? Of course, we all have. The book seeks to disambiguate the investment world’s seemingly secret world of concepts, terms, acronyms, and abbreviations. There’s even a handy glossary in the back, to quickly consult if needed!
Brent’s firm, adventur.es has long distinguished itself for its commitment to operating from a place of honesty, integrity, and a community-oriented mindset. The Messy Marketplace is no exception.
The Messy Marketplace is a book that I plan to consult often in my career, and believe will save me no shortage of money, time, and confusion down the road. Thank you to Brent & team!
December 29, 2019
Introduction
The Messy Marketplace is a book by Brent Beshore, CEO of adventur.es, that focuses on selling a business from the sellers perspective. It’s a very simple stroke of genius and is written in such an easy to follow fashion that any person interested in selling their business will benefit from this book. Heck any person interested in learning about deal structure in general will benefit from this book.
Why Should You Read This Book?
At exactly 100 pages of content this book is the perfect read for entrepreneurs, business owners, and generally anyone interested in how the process to sell a business works. Brent has clearly been successful doing it time and again and he shares some of the simple lessons he has learned along the way.
You should read this book if you are interested in learning some of the basics around selling a business. You should read this book if you are interested in buying a business as well. And you should definitely read this book if you are interested in direct investments into private businesses.
Final Thoughts
Brent Beshore gives really simple and excellent insight into how to get a business sold. The tips in this book are bi-directional, meaning they apply to sellers but can be understood by buyers. In fact, regardless on what side of the coin you are on (buy side or sell side) you will benefit from reading this book.
Regardless of your experience level with deals this is a great refresher and summary for anyone involved in business transactions.
Easy to Read: (5/5) 100%
Deep Content: (3/5) 60%
Overall Rating: (4/5) 80%
The Messy Marketplace is a book by Brent Beshore, CEO of adventur.es, that focuses on selling a business from the sellers perspective. It’s a very simple stroke of genius and is written in such an easy to follow fashion that any person interested in selling their business will benefit from this book. Heck any person interested in learning about deal structure in general will benefit from this book.
Why Should You Read This Book?
At exactly 100 pages of content this book is the perfect read for entrepreneurs, business owners, and generally anyone interested in how the process to sell a business works. Brent has clearly been successful doing it time and again and he shares some of the simple lessons he has learned along the way.
You should read this book if you are interested in learning some of the basics around selling a business. You should read this book if you are interested in buying a business as well. And you should definitely read this book if you are interested in direct investments into private businesses.
Final Thoughts
Brent Beshore gives really simple and excellent insight into how to get a business sold. The tips in this book are bi-directional, meaning they apply to sellers but can be understood by buyers. In fact, regardless on what side of the coin you are on (buy side or sell side) you will benefit from reading this book.
Regardless of your experience level with deals this is a great refresher and summary for anyone involved in business transactions.
Easy to Read: (5/5) 100%
Deep Content: (3/5) 60%
Overall Rating: (4/5) 80%
December 19, 2018
This book is great for what it was created for: a reference guide for sellers looking to sell their small business without experience from previous transactions. This book would also be an incredible educational tool for interns or recent college grads to read on the first week of their job in M&A. Outside of those 2 cases, I wouldn’t recommend this book.
With that being said, Brent Beshore is the man and you should check out every talk or piece of writing he’s done online.
With that being said, Brent Beshore is the man and you should check out every talk or piece of writing he’s done online.
Read
September 15, 2024Another quick read. Written by a buyer, this book pares well with (lots of content overlap, slightly different perspective) HBR’s Guide to Buying a Small Business. The diligence list (www.permanentequity.com/diligence) is an excellent resource for risk review (whether or not being used in context of buy/sell consideration).
January 16, 2019
Disclosure: I've met Brent, listened to his interviews and talks he's given and greatly admire his approach to investing and business. He's looked at thousands of deals and is not coming at this from an academic point of view.
I think this book is a wake-up call as well as a playbook for small business owners that are nearing the end of their working careers and haven't a clue where to start the process of harvesting the fruits of the business they have built over the years. Many owners are too busy managing their business to worry about selling it. Even if a sale is on their radar, this will likely be their only sale while the buyer may have closed on dozens of businesses and seen hundreds if not thousands.
Beshore starts with asking the seller to examine their motivations and manage their expectations. From there, he looks at the various types of buyers, their goals, limitations, and expectations and how these affect the seller. Along the way he takes care to familiarize the reader/seller with the metrics and jargon of the transaction process, the players they'll encounter, and the pitfalls to expect. Though the mechanics of the deal are spelled out in great detail, Beshore never loses focus on the fact that owners, employees, customers, and suppliers are all people and need to handle themselves and be handled with professionalism and grace throughout the entire process.
For advisors and financial professionals, I found this to be a good companion to HBR Guide to Buying a Small Business by Richard S. Ruback and Royce Yudkoff. That book, of course, looks at the process from the buyer's point of view, but the overlap between the two books reinforces the expectations you'll encounter in a deal. Beshore also stresses the importance of having good, experienced advisors on your side. Those advisors who are not experts on the process (and sorry, reading this book doesn't qualify you - or me) should have the humility and professionalism to help their client-owners find someone who is.
Finally, a word on the book's design. I was delighted when I unpacked this book like I have been with no other in recent memory. With a hard, glossy cover sans dust jacket, it immediately reminded me of my elementary school textbooks. Appropriate, because Beshore, like most good teachers, loves his subject and has generously shared his knowledge with the rest of us.
I think this book is a wake-up call as well as a playbook for small business owners that are nearing the end of their working careers and haven't a clue where to start the process of harvesting the fruits of the business they have built over the years. Many owners are too busy managing their business to worry about selling it. Even if a sale is on their radar, this will likely be their only sale while the buyer may have closed on dozens of businesses and seen hundreds if not thousands.
Beshore starts with asking the seller to examine their motivations and manage their expectations. From there, he looks at the various types of buyers, their goals, limitations, and expectations and how these affect the seller. Along the way he takes care to familiarize the reader/seller with the metrics and jargon of the transaction process, the players they'll encounter, and the pitfalls to expect. Though the mechanics of the deal are spelled out in great detail, Beshore never loses focus on the fact that owners, employees, customers, and suppliers are all people and need to handle themselves and be handled with professionalism and grace throughout the entire process.
For advisors and financial professionals, I found this to be a good companion to HBR Guide to Buying a Small Business by Richard S. Ruback and Royce Yudkoff. That book, of course, looks at the process from the buyer's point of view, but the overlap between the two books reinforces the expectations you'll encounter in a deal. Beshore also stresses the importance of having good, experienced advisors on your side. Those advisors who are not experts on the process (and sorry, reading this book doesn't qualify you - or me) should have the humility and professionalism to help their client-owners find someone who is.
Finally, a word on the book's design. I was delighted when I unpacked this book like I have been with no other in recent memory. With a hard, glossy cover sans dust jacket, it immediately reminded me of my elementary school textbooks. Appropriate, because Beshore, like most good teachers, loves his subject and has generously shared his knowledge with the rest of us.
July 27, 2019
A good look behind the curtain for business owners who are considering the sale of their business. It addresses and dispels a number of myths that too many business owners encounter. The section on "exercising buyers" carefully is important and excellently presents the proper processes.
September 11, 2024
Excellent reference
Terrific reference for owners and others around the sale of businesses. Quick, helpful and no fat. Really good for outside advisers that need to get into the concerns of the people driving the transaction.
Terrific reference for owners and others around the sale of businesses. Quick, helpful and no fat. Really good for outside advisers that need to get into the concerns of the people driving the transaction.
September 17, 2025
great book for becoming aware of the steps and people involved in small business acquisitions. if you're getting involved, just make sure you don't go overkill and scare a seller off with the full checklist.
February 13, 2019
Good overview for buying/selling a general business for $5-$30mm. Highly targeted market. No specifics in to tech related companies. All high level overview with things to expect.
September 25, 2022
Great intro book and helpful for those working in M&A as a reference guide.
September 11, 2023
Solid no BS overview of buying and selling a small to medium sized business and the entire process
May 26, 2024
For what it aims to do, it does exceptionally well. No fluff, just straight to the point all the way through.
October 15, 2024
If I ever sell a business, I'll definitely read this again and try apply the clear, practical advice.
October 10, 2020
Tons of valuable information for small business owners. Even if you are not thinking about selling your business, its always important to know what makes a company attractive for a buyer.
July 23, 2024
Best book on private equity that I’ve ever read. Also the only book on private equity that I’ve ever read. Seems like a comprehensive playbook on how to think about selling a business. I would be interested in hearing more from the buyers side. Hopefully Brent comes out with a sequel about that.
Read
December 16, 2018Very, very good primer for business owners. I'd buy a copy for any sellers I work with in the future, except that it doesn't paint search funds, fundless sponsors and even other PEGs in a good light. That said, I read it because I can always learn more about the acquisition process and I very much enjoy the author's thoughtful content and contributions on Twitter.
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