In The Trenches

In his book, The Five Temptations of a CEO, author Patrick Lencioni discusses five areas in which CEOs tend to inadvertently prioritize the wrong things. These “temptations”, as he calls them, can lead to poor decision making at best, and can risk the very survival of the company at worst. My experience leading a software company taught me that there is a sixth temptation, unique to software, that seemed to present itself on a near-daily basis. More specifically: The biggest temptation of a software CEO is to throw bodies (specifically engineers) at problems. It is this sixth temptation that I struggled with most frequently. With the benefit of hindsight, I’ve come to a few realizations that I’d like to share with fellow software CEOs in hopes that they’ll do a better job of managing this temptation than I did. Among other lessons, I share how the following realities should shape the decision of whether or not (and by how much) to increase the size of the company's engineering team: Communication channels grow non-linearly as team size increases Work expands to fill the time allotted for its completion The development team will never be big enough One unit of additional capacity often doesn’t produce a unit of additional output When CEOs add more developers, they’re often attempting to solve the wrong problem It’s much easier to add than it is to take away Hiring engineers can be a very difficult hire to quantify  Please enjoy!

My guest today is Carin-Isabel Knoop, Executive Director of the Harvard Business School Case Research & Writing Group. Carin has spent decades writing cases on managers and leaders all over the world, across a wide array of functions and industries. In 2019, alongside co-author John Quelch, she published Compassionate Management of Mental Health in the Modern Workplace, a book that dove deeply into the relationship between work life and mental well-being, and suggested in which managers can and should act as the "chief mental health officers" of their respective teams.   In today's episode, we dive deeply into the following questions and issues:  Link between employee burnout and turnover Signs for leaders to look for that may be predictive of turnover Prevention strategies, for both the CEO and her employees Can CEOs maintain “high performance cultures” while simultaneously managing the risk of employee burnout? How to detect emotional depletion within yourself Personality traits that are positively correlated with burnout risk  Separating your own sense of happiness from the success of your business at any given time How acquirors of businesses can and should perform due diligence on the employee base that they're acquiring Please enjoy!

Today's episode is aimed towards those who may be wrestling with the question of whether or not to finally pursue their entrepreneurial dreams. I walk you through how I made this decision myself in 2012, and also attempt to compliment those considerations with some of the lessons and reflections that I’ve garnered in the 10 years since then, which of course benefit from the clarity that only seems to come with hindsight.  Whether or not to take the entrepreneurial plunge is a deeply personal question, and as a result no objectively correct answer exists to address it. What I argue in this episode however is that the answer itself will only be as good as the introspection, thought processes, and clarity of insights that led to it in the first place. Entrepreneurship is generally much less risky than most might think, though it is also significantly less glamorous than its depiction in most forms of media today. Though most people understandably focus on the risk of walking the entrepreneurial path, it’s equally important to acknowledge of risks of not doing so. Please enjoy!

In this week's episode, we discuss the importance of having difficult conversations, something that CEOs find themselves doing on a near-daily basis. We discuss three primary types of difficult conversations, including a) Hard conversations around internal company dynamics (eg: terminations); b) Hard conversations about dynamics external to the company (eg: politics); & c) Difficult conversations that CEOs must sometimes have with themselves (eg: how and when to ask for help). This is a particularly special episode of In The Trenches for a number of reasons, including: It is our first ever video podcast! (Video available only through Spotify, however) This is our first ever episode featuring a panel discussion, including myself and a panel of four SMB CEOs, investors and Board members This episode is a recording of a session that I moderated during the 2022 MIT Sloan Search Fund Summit, hosted by the ETA@MIT club  Please enjoy!

My experience as a CEO taught me that the most important skill for any leader to possess is that of clear and effective communication. Indeed, a CEO’s strategy is only as good as her ability to communicate it.  Though some of the basic tenets of effective communication are obvious and intuitive, others are less so. My experience leading a company over many years illustrated that good organizational communication often went well beyond the basics. In this episode, I will share with you some of the most important lessons that I learned about effective communication within my own company, including if, how & when to communicate around terminations, financial results, good news, bad news, and many others. Please enjoy!

Chris Hutchinson, a Partner at Ernst & Young's Transaction Advisory Services, shares his expertise on Quality of Earnings (QofE) analysis, crucial for evaluating sustainable earnings during acquisitions. He explains its importance, particularly in the lower middle market, and highlights common pitfalls for buyers and sellers. Chris dives into working capital adjustments and their significance, alongside insights on navigating post-COVID financial evaluations. With over 15 years in M&A, he emphasizes effective communication to achieve realistic valuations and protect interests in complex deals.

Among the myriad variables that must be carefully considered when acquiring a business is the question of how the acquisition is going to be financed. In today's episode, I will provide you with an overview of the specific lessons that I learned when financing my own acquisition in 2014. I begin by discussing the critical importance of the link between capital structure and strategy, and then discuss more specific lessons learned in raising the debt required to finance the acquisition.  Please enjoy!

Though Aaron Ross wears many hats, he is perhaps best known for co-authoring the global best seller Predictable Revenue, often referred to as “The Sales Bible of Silicon Valley,” which details an outbound prospecting system that’s created more than $1 billion across Salesforce.com and other companies. Most recently, Aaron published From Impossible to Inevitable, a book co-written alongside Jason Lemkin (serial tech entrepreneur, venture capitalist, and founder of SaaStr.com, the world’s #1 resource for SaaS entrepreneurs), which is a "hypergrowth playbook" based on the successes of companies like Twilio, HubSpot, Marketo, and Salesforce.com. In addition to being a sales advisor, board member, and highly sought after public speaker, Aaron also authors his own substack page, Fresh Air, where he focuses on the personal aspects of being a senior executive, including how to best manage anxiety, exhaustion, and stress, all of which are par for the course for substantially all entrepreneurs and CEOs.

The role of spouse to an entrepreneur or CEO is not an easy one, as they are directly impacted by the emotional high and lows that are typical of the journey: They act as a source of consolation during the bad times, keep us grounded during the good times, and in many cases play a large (though often unnoticed and under-appreciated) role in our ultimate successes and failures. In spite of the importance of the role that spouses play however, the role of a spouse or partner in the entrepreneurial journey is a very under-discussed topic, at least within the literature that I'm aware of. In today's episode, I attempt to shine a light on the role that spouses play in the entrepreneurial journey from the perspective of both the spouse and the entrepreneur: I do this by discussing my own experiences, as well as presenting the results of two anonymous surveys, one of which was sent to a group of entrepreneurs and CEOs, and one of which was sent to their spouses.  If you're an entrepreneur or CEO, I encourage you to please share this episode with your spouse!

My guest today is Bob Pritchett, and I’m really excited to be sharing this episode with you. Bob first came on my radar when I read his book titled “Fire Someone Today”, which was published in 2006. Right before I purchased my first software company, one of my investors and mentors purchased the book for me as a gift, and promised me that, in spite of the fact that I had likely never heard of the book, it was full of countless gems for entrepreneurs and CEOs running SMBs. And he was right: Fire Someone today remains one of my favorite all-time business books, partially because of how it was written: Usefulness, practicality, and tactical/actionable advice take the place of the theory and anecdotes that unfortunately populate many other business books that often feel like they were written inside of an ivory tower. Bob is not just an author: He’s also a Founder, lifetime entrepreneur and CEO: Bob founded Logos Research Systems (later Logos Bible Software and now Faithlife) in 1992, and acted as its CEO for 30 years, until recently assuming the role of Executive Chairman. During Bob's tenure, Faithlife has grown both organically and inorganically from two employees to over 500, with the company now serving thousands of customers across 170 countries worldwide. Bob was a also recipient of E& Y's Entrepreneur of the Year Award in 2005. In our conversation today, we discuss how one falls into the bible software business, the merits and risks of pursuing an entrepreneurial venture with a partner, why many business partnerships fail, how much you should actually listen to your customers, what functions to inhouse versus outsource, and the practices and routines that he’s implemented to help him sustain 30 years as an entrepreneur. Enjoy!