This episode is brought to you by Avidbank . Avidbank is one of the most experienced search fund lenders in North America, having funded over 40 separate transactions since 2014, for a total of over $300M. They are deeply familiar with the search fund model, and understand the nuances of the fundraising process, dealing with sellers, communicating with your equity investors, LOI reviews, and everything else in between. Reach out to Anthony Rodriguez (arodriguez@avidbank.com) or Conor Tidgwell (c...
Mar 16, 2023•28 min•Season 6Ep. 7
This episode is brought to you by The Profit Line . The Profit Line is a boutique finance and accounting firm that provides a wide range of accounting services to small and medium businesses generating anywhere between $5M to $50M in revenue. On a fractional, outsourced basis, they do day-to-day bookkeeping, bank reconciliations, month-end accruals, tax compliance, and financial statement preparation, among countless other things. I was a customer of theirs for 7 consecutive years while running ...
Mar 02, 2023•1 hr 38 min•Season 6Ep. 6
This episode is brought to you by The Profit Line . The Profit Line is a boutique finance and accounting firm that provides a wide range of accounting services to small and medium businesses generating anywhere between $5M to $50M in revenue. On a fractional, outsourced basis, they do day-to-day bookkeeping, bank reconciliations, month-end accruals, tax compliance, and financial statement preparation, among countless other things. I was a customer of theirs for 7 consecutive years while running ...
Feb 16, 2023•15 min•Season 6Ep. 5
This episode is brought to you by The Profit Line . The Profit Line is a boutique finance and accounting firm that provides a wide range of accounting services to small and medium businesses generating anywhere between $5M to $50M in revenue. On a fractional, outsourced basis, they do day-to-day bookkeeping, bank reconciliations, month-end accruals, tax compliance, and financial statement preparation, among countless other things. I was a customer of theirs for 7 consecutive years while running ...
Feb 02, 2023•1 hr 30 min•Season 6Ep. 4
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 bus...
Jan 19, 2023•22 min•Season 6Ep. 3
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 bus...
Jan 05, 2023•1 hr 31 min•Season 6Ep. 2
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 w...
Dec 22, 2022•1 hr•Season 6Ep. 1
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 w...
Dec 08, 2022•31 min•Season 5Ep. 10
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, ali...
Nov 24, 2022•1 hr 27 min•Season 5Ep. 9
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, ali...
Nov 10, 2022•23 min•Season 5Ep. 8
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, ali...
Oct 27, 2022•1 hr 14 min•Season 5Ep. 7
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, ali...
Oct 13, 2022•20 min•Season 5Ep. 6
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 w...
Sep 29, 2022•1 hr 19 min•Season 5Ep. 5
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 ...
Sep 15, 2022•19 min•Season 5Ep. 4
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 level to be useful, so today I wanted to get really detailed on how to select an M&A advisor, how m...
Sep 01, 2022•1 hr 7 min•Season 5Ep. 3
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, I would argue that they are premature at best, and misleading (or even incorrect) at worst. This audio b...
Aug 04, 2022•16 min•Season 5Ep. 1
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. Our conversation begins with several questions about how to manage cash and other sources o...
Jul 21, 2022•1 hr 17 min•Season 4Ep. 10
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 actually much harder to both purchase and operate when compared to their larger peers.
Jul 07, 2022•14 min•Season 4Ep. 9
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 such times. We also discuss how CEOs should think about pricing their products and services in respon...
Jun 23, 2022•1 hr 2 min•Season 4Ep. 8
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 sof...
Jun 09, 2022•16 min•Season 4Ep. 7
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 ...
May 26, 2022•1 hr 9 min•Season 4Ep. 6
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 ques...
May 12, 2022•21 min•Season 4Ep. 5
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 part...
Apr 28, 2022•1 hr•Season 4Ep. 4
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...
Apr 14, 2022•16 min•Season 4Ep. 3
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 industries, including software, technology, business services, distribution, and retail, am...
Mar 31, 2022•1 hr 2 min•Season 4Ep. 2
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 en...
Mar 17, 2022•21 min•Season 4Ep. 1
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 res...
Mar 03, 2022•51 min•Season 3Ep. 10
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...
Feb 17, 2022•21 min•Season 3Ep. 9
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 ...
Feb 03, 2022•1 hr 15 min•Season 3Ep. 8
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 sophisticated and experienced counterpart (even AFTER the sale of their business is already complete)...
Jan 20, 2022•12 min•Season 3Ep. 7
