In The Trenches

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...

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 i...

Today’s episode is for anybody who ever plans to sell a company. Most entrepreneurs will sell a business once in their entire careers (if they’re lucky), and as a result many understandably don’t have a lot of context or experience in the finer points of exiting, specifically when it comes to how to select an M&A advisor. Most advice that I’ve come across in this domain is frankly too high lev...

For many business owners, few things are as exciting as receiving a Letter of Intent (“LOI”) from a prospective purchaser. Beyond the sense of validation stemming from the fact that a sophisticated counterparty sees an asset worth paying for, many business owners likely view an LOI as a just reward for decades of hard work, sacrifice, and illiquidity.  Understandable as these reactions may be...

Today's episode is all about the finance & accounting function: My guest is Nicholas Andrews, who is the Founder of Aspen Consulting Group, a company that performs finance, accounting, and operations consulting for a wide range of small and medium sized businesses. Aspen’s services include technical accounting, corporate finance, valuations, operations planning and M&A due diligence, among others....

In this episode, I attempt to debunk a common misconception among prospective acquirors, particularly those looking to purchase a business for the first time. This myth states that the smaller the business in question, the easier it is to purchase and operate. In the material that follows, I will attempt to explain why the exact opposite statement is likely true: That smaller companies are actuall...

My guest today is a particularly personal and a particularly special one for me: I have been fortunate to call Jim Sharpe a mentor and friend for over 10 years now, and I am thrilled that he agreed to join the podcast. In this week's episode, we discuss the realities of running a business during high inflation environments, including the risks and opportunities that may present themselves during s...

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, tha...

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...

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...

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 conversati...

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 organizationa...

My guest today is Chris Hutchinson, a Partner in Ernst & Young's Transaction Advisory Services Group. Chris has over 15 years of experience advising clients on M&A, financings, valuation projects, and due diligence mandates, with a specific focus on private lower-middle-market businesses. Chris and his team have completed an untold number of Quality of Earnings ("QofE") mandates spanning countless...

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 disc...

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...

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 impo...

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...

The Working Capital Adjustment is part of substantially every M&A transaction, yet it is the calculation (and concept) with which most business owners remain largely unfamiliar. Without a proper understanding of what the working capital adjustment is, why it's necessary, and ways in which it can be manipulated, business owners risk leaving a lot of money on the table when dealing with a more s...

Today’s episode is all about Hiring, and we’ve managed to secure one of the world’s foremost experts on the subject. My guest is Randy Street. Randy is Vice Chairman of ghSMART , which is a global consulting firm that helps CEOs, boards, and investors build valuable companies specifically through hiring and developing world class leadership teams . During Randy's tenure, ghSMART has grown tenfold,...

In today's episode, I discuss the signs that prospective acquirors should look out for when attempting to uncover how much “technical debt” any given target company may possess within their code base. Though substantially every software company has some amount of technical debt, those that are weighed down by an asymmetric burden of it tend to ship code less frequently, struggle to keep pace with...

Verne Harnish quite literally wrote the book (or, in his case, books), on being an entrepreneur and CEO running a small to medium sized business. Verne is the founder of the world-renowned Entrepreneurs’ Organization ("EO"), a global network of entrepreneurs and CEOs that boasts over 16,000 members worldwide. For the past 15 years, Verne has chaired EO’s premiere CEO program, the “Birthing of Gian...

Throughout recent history, there has been substantial growth in the number of companies who have decided to implement formal “operating systems” to govern certain strategic and operational decisions within their businesses. Though there are many operating systems in existence today, two of the most widely used systems are EOS (based on the book Traction, by Gino Wickman) and The Rockefeller Habits...

Today’s show is all about GROWTH. Specifically, I want to dig into the personal and professional realities of running a high growth company that often aren't terribly visible from the outside looking in. Today, I talk to Anthemos Georgiades (or Anth, for short), who is the founder and CEO of Zumper, an apartment rental platform based out of San Francisco.  If anybody knows about running a rapidly...

Acquiring any business is hard. Acquiring a software company is no exception, and indeed may prove to be even more intimidating to the inexperienced acquiror due to certain non-obvious considerations unique to software companies and the business models under which they operate. In this audio blog, I explore several of these unique and non-obvious considerations for the prospective software acquiro...

Today's episode is all about the legal issues and considerations involved in selling a small to medium sized business ("SMB"), many of which tend to be unfamiliar to CEOs and Entrepreneurs.  My guest, Mario Nigro, is one of Canada's preeminent M&A lawyers, and currently serves as a Partner in the Mergers & Acquisitions and Private Equity & Venture Capital Groups at Stikeman Elliot...