This episode is brought to you by Warren Coughlin, CEO Coach and founder of JumpStart Coaching. Warren focuses exclusively on coaching CEOs running SMBs, and has been doing so for over 20 years. One of my biggest regrets across my 7 years as a CEO was not hiring a coach, and I want to prevent others from making the same mistake. For listeners of In The Trenches, working with Warren is effectively risk-free: If at the end of the first three months you're not happy with the direction of your business, he will give you your money back. On top of that, Warren is offering $3,000 off of his coaching program for listeners of In The Trenches. Just go to warrencoughlin.com/trenches to learn more. * This episode is brought to you by Cayne Crossing. Cayne Crossing helps prospective SMB purchasers with all aspects of financial due diligence, including producing the Quality of Earnings report.  Unlike any other QofE provider that I’m aware of, Cayne Crossing also co-invests alongside their buyers, aligning their interests with yours in a way that I simply haven’t seen anywhere else. Cayne Crossing is offering a special discount to listeners of In The Trenches: Just go to caynecrossing.com, and scroll down to the “contact form” on their homepage. Enter the offer code “trenches”, and you will get a full $2,000 off of your QofE engagement with them. * CEOs running newly public companies, those who have raised external equity for the first time, and those occupying the CEO seat for the first-time are often intimidated by the idea of reporting into a Board, and are uncertain of how to construct, manage, communicate with, and learn from them. This combination of uncertainty and inexperience often creates undue stress for CEOs, and can create situations in which they are more focused on impressing their Boards than they are on leaning on them for support, guidance, and mentorship. Over many years as a CEO reporting directly into a Board (and now as an investor who sits on Boards and works directly with CEOs myself), I’ve come to learn a few things about how to construct, manage, communicate with, and learn from this critically important group of people. This episode is my best attempt at sharing these lessons with you. 

This episode is brought to you by Warren Coughlin, CEO Coach and founder of JumpStart Coaching. Warren focuses exclusively on coaching CEOs running SMBs, and has been doing so for over 20 years. One of my biggest regrets across my 7 years as a CEO was not hiring a coach, and I want to prevent others from making the same mistake. For listeners of In The Trenches, working with Warren is effectively risk-free: If at the end of the first three months you're not happy with the direction of your business, he will give you your money back. On top of that, Warren is offering $3,000 off of his coaching program for listeners of In The Trenches. Just go to warrencoughlin.com/trenches to learn more. __________________________ This episode is brought to you by Cayne Crossing. Cayne Crossing helps prospective SMB purchasers with all aspects of financial due diligence, including producing the Quality of Earnings report.  Unlike any other QofE provider that I’m aware of, Cayne Crossing also co-invests alongside their buyers, aligning their interests with yours in a way that I simply haven’t seen anywhere else. Cayne Crossing is offering a special discount to listeners of In The Trenches: Just go to caynecrossing.com, and scroll down to the “contact form” on their homepage. Enter the offer code “trenches”, and you will get a full $2,000 off of your QofE engagement with them. __________________________ My guest today is Mike Zani, CEO of The Predictive Index. The Predictive Index serves more than 9,000 clients across 142 countries, helping businesses optimize their hiring and team composition decisions through behavioral science, software, and professional consulting from the world's top workplace behavioral specialists. Mike has been CEO of The Predictive Index for approximately 8 years, after having purchased the business from its original founders. Prior to leading The Predictive Index, Mike successfully purchased, operated, and sold two other companies in the employee wellness and manufacturing industries. The Predictive Index is one of the most widely-used personality profiling tools utilized by SMB CEOs when making hiring decisions, and in today's discussion we discuss these types of tools at length: When they're most useful (and when they're not), the most frequent sources of hiring mistakes, how transferable they are to blue collar industries, how we might utilize them in our personal relationships, and how he would utilize similar tools if looking to buy another business, to name just a few. Please enjoy!  

This episode is brought to you by Warren Coughlin, CEO Coach and founder of JumpStart Coaching. Warren focuses exclusively on coaching CEOs running SMBs, and has been doing so for over 20 years. One of my biggest regrets across my 7 years as a CEO was not hiring a coach, and to the best extent possible, I want to prevent others from making the same mistake. For listeners of In The Trenches, working with Warren is effectively risk-free: If at the end of the first three months you're not happy with the direction of your business, he will give you your money back. If that doesn’t say confidence, I don’t know what does. On top of that, Warren is offering $3,000 off of his coaching program for listeners of In The Trenches. Just go to warrencoughlin.com/trenches to learn more.  __________________________  This episode is brought to you by Cayne Crossing. Cayne Crossing helps prospective SMB purchasers with all aspects of financial due diligence, including producing the Quality of Earnings report.  Unlike any other QofE provider that I’m aware of, Cayne Crossing also co-invests alongside their buyers, aligning their interests with yours in a way that I simply haven’t seen anywhere else. Cayne Crossing is offering a special discount to listeners of In The Trenches: Just go to caynecrossing.com, and scroll down to the “contact form” on their homepage. Enter the offer code “trenches”, and you will get a full $2,000 off of your QofE engagement with them.  __________________________  This episode attempts to directly address many of the questions that I’ve been asked over the past 6 months related to the current state of the debt markets: How pricing has changed, how credit availability has evolved, what risks banks are no longer willing to underwrite, how their diligence processes have changed, how non-price terms have evolved, and so on. To help me better understand the current state of the debt markets, I reached out to Cory Kaiser and Tim Eaton, both of whom work at TD in their commercial lending group: Cory is Vice President of commercial banking and has been with TD for over 21 years, and Tim is an associate vice president, who has been with TD for 23 years. Over the past two decades, their focus has been (and will continue to be) on lending to lower-middle market private companies, not just to finance their acquisitions, but also to finance growth, working capital, and recapitalizations, to name just a few. I hope this episode helps to clarify some of the questions that you might be wrestling with yourself. Please enjoy!

This episode is brought to you by Warren Coughlin, CEO Coach and founder of JumpStart Coaching. Warren focuses exclusively on coaching CEOs running SMBs, and has been doing so for over 20 years. One of my biggest regrets across my 7 years as a CEO was not hiring a coach, and to the best extent possible, I want to prevent others from making the same mistake. For listeners of In The Trenches, working with Warren is effectively risk-free: If at the end of the first three months you're not happy with the direction of your business, he will give you your money back. If that doesn’t say confidence, I don’t know what does. On top of that, Warren is offering $3,000 off of his coaching program for listeners of In The Trenches. Just go to warrencoughlin.com/trenches to learn more.  __________________________ This episode is brought to you by Cayne Crossing. Cayne Crossing helps prospective SMB purchasers with all aspects of financial due diligence, including producing the Quality of Earnings report.  Unlike any other QofE provider that I’m aware of, Cayne Crossing also co-invests alongside their buyers, aligning their interests with yours in a way that I simply haven’t seen anywhere else. Cayne Crossing is offering a special discount to listeners of In The Trenches: Just go to caynecrossing.com, and scroll down to the “contact form” on their homepage. Enter the offer code “trenches”, and you will get a full $2,000 off of your QofE engagement with them. __________________________ Enterprise software is considered to be among the world’s best business models. However, getting access to the world’s best business model doesn’t come cheaply: Software businesses most frequently trade at multiples of recurring revenue, which stands in contrast to most other industries in which businesses tend to trade at multiples of EBITDA or cash flow.  But not all software investment theses are created equally: There are indeed several different approaches to acquiring and building a software company, and each approach presents a different investment thesis, requires different operational and value creation strategies, and is likely to command different asking prices. In today's episode, I present and evaluate 5 very different approaches that buyers might consider in their pursuit of a software business. Though this list of approaches is by no means exhaustive, it does capture those that I tend to see most frequently.  Please enjoy!

This episode is brought to you by Cayne Crossing. Cayne Crossing helps prospective SMB purchasers with all aspects of financial due diligence, including producing the Quality of Earnings report. I have personally read though, analyzed, and relied upon several of their actual QofE reports in my capacity as an SMB investor, and can personally attest to the quality of the work that they do. Unlike any other QofE provider that I’m aware of, Cayne Crossing also co-invests alongside their buyers, aligning their interests with yours in a way that I simply haven’t seen anywhere else. Cayne Crossing is offering a special discount to listeners of In The Trenches: Just go to caynecrossing.com, and scroll down to the “contact form” on their homepage. Enter the offer code “trenches”, and you will get a full $2,000 off of your QofE engagement with them. __________________________ My guest today is Brent Beshore. Brent is Founder and CEO of Permanent Equity, a private investment firm that invests in Founder-owned private companies. Permanent Equity is a (very) long-term investor that typically intends to hold portfolio companies indefinitely, often without the use of any leverage. In addition to his role as an investor, Brent is also a prolific writer: He is a regular contributor to Forbes, and also publishes and releases materials for free on Permanent Equity's website, spanning topics like operating, selling, and investingin SMBs, among others. Brent is also the author of The Messy Marketplace, a book that aims to demystify the process of selling a company. I must say that this conversation was a real pleasure for me to have. Brent is a really thoughtful guy who has a lot of really unique and insightful views on buying, running, and selling SMBs. And, of all the many conversations that I’ve had recently, this one might cover the most ground: So strap in for a very wide-ranging discussion, and please enjoy. 

This episode is brought to you by Cayne Crossing. Cayne Crossing helps prospective SMB purchasers with all aspects of financial due diligence, including producing the Quality of Earnings report. I have personally read though, analyzed, and relied upon several of their actual QofE reports in my capacity as an SMB investor, and can personally attest to the quality of the work that they do. Unlike any other QofE provider that I’m aware of, Cayne Crossing also co-invests alongside their buyers, aligning their interests with yours in a way that I simply haven’t seen anywhere else. Cayne Crossing is offering a special discount to listeners of In The Trenches: Just go to caynecrossing.com, and scroll down to the “contact form” on their homepage. Enter the offer code “trenches”, and you will get a full $2,000 off of your QofE engagement with them. _______________________________________________________ In today’s episode I get unapologetically tactical, and discuss the specific tools, routines, and practices that I have found to be particularly effective in managing my own psychology as an entrepreneur and CEO. I chose to write about this topic based on the following three deeply held beliefs: (1) A CEO’s ability to manage herself is at least as important as, if not more important than, her ability to manage her business; (2) Unless you are deliberate about managing your own psychology, you risk becoming a sort of “victim” to the circumstances that happen to present themselves in your life at any given time; & (3) Over time, the mood of the broader employee base often directly reflects that of the leader.  I hope at least some of these prove to be helpful for you

This episode is brought to you by Cayne Crossing. Cayne Crossing helps prospective SMB purchasers with all aspects of financial due diligence, including producing the Quality of Earnings report. I have personally read though, analyzed, and relied upon several of their actual QofE reports in my capacity as an SMB investor, and can personally attest to the quality of the work that they do. Unlike any other QofE provider that I’m aware of, Cayne Crossing also co-invests alongside their buyers, aligning their interests with yours in a way that I simply haven’t seen anywhere else. Cayne Crossing is offering a special discount to listeners of In The Trenches: Just go to caynecrossing.com, and scroll down to the “contact form” on their homepage. Enter the offer code “trenches”, and you will get a full $2,000 off of your QofE engagement with them. _______________________________________________________ My guest today is A.J. Wasserstein, the Eugene F. Williams, Jr. Lecturer in the Practice of Management at the Yale School of Management. His research, writing, and teaching concentrates on search funds, entrepreneurship, programmatic acquisitions, and small businesses. In addition to his role as an educator, A.J. is also a private investor in lower middle-market businesses. He was the President of Onesource Water, the third-largest bottleless water service business in the U.S., which was sold to Water Logic, a U.K.-based strategic acquirer, in 2016. Previously, A.J. was the founder and CEO of ArchivesOne, the third largest records management company in the U.S. ArchivesOne was sold to Iron Mountain (NYSE: IRM) after 17 years of operation. A.J.'s incredible collection of writing can be accessed here.

This episode is brought to you by Cayne Crossing. Cayne Crossing helps prospective SMB purchasers with all aspects of financial due diligence, including producing the Quality of Earnings report. I have personally read though, analyzed, and relied upon several of their actual QofE reports in my capacity as an SMB investor, and can personally attest to the quality of the work that they do. Unlike any other QofE provider that I’m aware of, Cayne Crossing also co-invests alongside their buyers, aligning their interests with yours in a way that I simply haven’t seen anywhere else.   Cayne Crossing is offering a special discount to listeners of In The Trenches: Just go to caynecrossing.com, and scroll down to the “contact form” on their homepage. Enter the offer code “trenches”, and you will get a full $2,000 off of your QofE engagement with them.  _______________________________________________________  Episode Description: Relative to its importance, capital allocation seems to be a relatively under-discussed subject among SMB CEOs. The subject is at least as important as more common day-to-day issues like hiring, culture, or compensation, though it rarely seems to occupy the same share-of-mind. Though capital allocation isn't a discipline that CEOs consciously or explicitly deprioritize, it often loses the battle for their time and attention when competing with more common day-to-day issues like those mentioned above.   As a CEO you’d be wise to regularly look at your business through the lens of an investor to ensure that you’re allocating your company’s scarce financial resources towards their highest and best use. In today's episode, I discuss some relevant lessons that I’ve collected over the years related to capital allocation, some of which I hope are helpful to you.

My guests today are Steve Lau and Rameez Ansari, co-CEOs of AutoLeap, a software company that services auto repair shops, that counts Bain Capital Ventures among its investors. Prior to founding AutoLeap, Steve and Rameez purchased, operated, and sold D'Esco (later renamed FieldEdge), a software company that helps entrepreneurs run their HVAC, Plumbing, and Electrical Contracting businesses. Steve and Rameez purchased the company from its original founder in 2015 at 5X EBITDA, when its product was entirely on-premise and its revenue was generated solely through the sale of perpetual use licenses. After successfully transitioning the company to one that sold a cloud-based product and generated revenue on a subscription basis, they sold the company to a private equity firm for 8X revenue in 2019. For the past 5-10 years, investors have salivated over the return potential inherent in transitioning a sticky enterprise software product with low customer churn from on-premise to SaaS. Though returns like those generated by Steve and Rameez certainly illustrate that such transitions can be successfully made, the headlines often ignore how brutally difficult this transition tends to be, both operationally and financially. Though software investors and operators will find this episode relevant for what are probably obvious reasons, I’d also suggest that any CEO, in any industry, ought to pay attention to the lessons that Steve & Rameez learned, especially if they’re considering a transformation of any sort within their own companies. We talk about shifts in organizational culture, changes in salesforce compensation, how to communicate the need for change within a company, how to respect the history and legacy of a business while still keeping an eye towards the future, how non-technical CEOs can run a technically-oriented business, and much much more.

Unfortunate at this reality may be, I would argue that firing (specifically knowing who, when, and how to fire) is a required core competency for any CEO, and is arguably as important as hiring, communication, capital allocation, and other tools within the CEO’s toolkit. The extent to which this is an unpleasant (and perhaps even unpopular) topic to discuss doesn’t negate its critical importance in building and sustaining a healthy and vibrant company. Some may associate the idea of firing with toxic, authoritarian, or fear-based work cultures. While firing can lead to these types of outcomes if done in an arbitrary, thoughtless, or fear-inducing way, if and when done correctly, it can actually become one of the CEO’s primary tools in building a healthy, inclusive, fair and meritocratic culture. It’s important for me to note that this isn’t because firing itself is value-creating. It clearly isn’t. Being flippant or cavalier with the professional lives of your employees represents the surest path to destroying your company. Instead, one of the primary reasons why firing is so (unfortunately) important is because of how difficult, error-prone, and subjective most hiring processes are.