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PODCAST

In The Trenches

The only podcast dedicated exclusively to Entrepreneurs and CEOs running Small to Medium Sized Businesses (SMB). Nobody knows what it’s like to be an Entrepreneur or CEO unless you’ve been one. Though many understand the rewards of company leadership, very few understand the arduous journey that’s required to get (and stay) there. I share my own lessons as an Entrepreneur and CEO, and interview experts spanning Sales, Leadership, Mental Health, M&A, and Operations (among others) all with a

business entrepreneurship

All Episodes

01:30:52

Mike Zani, CEO of The Predictive Index: Hiring,...

In The Trenches ·

2023/01/05

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,

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00:59:39

The Current State of the Debt Capital Markets

In The Trenches ·

2022/12/22

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

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00:30:36

Evaluating 5 Very Different Approaches to Acquiring a...

In The Trenches ·

2022/12/08

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

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01:27:10

Brent Beshore: The "Forrest Gump of Private Equity"

In The Trenches ·

2022/11/24

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

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00:22:33

Tools in Managing my own Psychology

In The Trenches ·

2022/11/10

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, aligning

en

01:13:42

A.J. Wasserstein: Reflections of a Founder, CEO,...

In The Trenches ·

2022/10/27

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

en

00:20:24

The CEO as Chief Capital Allocator

In The Trenches ·

2022/10/13

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

en

01:18:50

Buy at 5X EBITDA, Sell at 8X Revenue: The On-Premise...

In The Trenches ·

2022/09/29

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

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00:19:23

Knowing Who, When, and How to Fire

In The Trenches ·

2022/09/15

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

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01:07:26

Sell-Side M&A Advisors: How to Choose One, How Much...

In The Trenches ·

2022/09/01

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 much

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00:15:32

Strategic Considerations When Evaluating a Letter of...

In The Trenches ·

2022/08/04

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 blog

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01:16:52

All Things Finance & Accounting: Managing Cash &...

In The Trenches ·

2022/07/21

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 of liquidity

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00:13:31

Busting the Biggest Myth About Purchasing and...

In The Trenches ·

2022/07/07

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.

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01:01:55

Running a Business During Inflationary Periods and...

In The Trenches ·

2022/06/23

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 response

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00:15:41

The Biggest Temptation of a Software CEO

In The Trenches ·

2022/06/09

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

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01:08:35

Employee Burnout and The Great Resignation

In The Trenches ·

2022/05/26

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

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00:20:40

Should You Become an Entrepreneur?

In The Trenches ·

2022/05/12

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

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01:00:20

Having Hard Conversations (Live Panel Discussion from...

In The Trenches ·

2022/04/28

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

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00:16:04

A Leader’s Most Important Skill

In The Trenches ·

2022/04/14

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

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01:01:57

Quality of Earnings Analysis: What You Need to Know...

In The Trenches ·

2022/03/31

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, among

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132 results

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