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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

00:21:06

Lessons Learned in Capitalizing an Acquisition

In The Trenches ·

2022/03/17

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

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00:51:25

Aaron Ross: Author of "Predictable Revenue" and "From...

In The Trenches ·

2022/03/03

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

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00:21:09

The Entrepreneur and the Spousal Relationship

In The Trenches ·

2022/02/17

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

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01:14:55

Bob Pritchett: Author of "Fire Someone Today" and...

In The Trenches ·

2022/02/03

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

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00:12:19

The Working Capital Adjustment

In The Trenches ·

2022/01/20

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). If

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01:10:52

All Things Hiring with Randy Street: Co-Author of "...

In The Trenches ·

2022/01/06

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, and has been ranked by Forbes as one of America’s Best Consulting Firms from 2017-2020. Randy first came

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00:27:01

Considerations Unique to Acquiring a Software Company...

In The Trenches ·

2021/12/23

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 competitors, regularly miss release targets, and are generally much more expensive and capital intensive

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01:00:56

Verne Harnish: Founder of The Entrepreneurs'...

In The Trenches ·

2021/12/09

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 Giants” held at MIT, a program in which he still teaches today. Verne is also the Founder and CEO of Scaling

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00:15:53

Implementing a Formal Operating System Like EOS or...

In The Trenches ·

2021/11/25

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 (based on the books Mastering the Rockefeller Habits and Scaling Up, both by Verne Harnish). I

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01:19:13

The Realities of Managing Extremely Rapid Growth

In The Trenches ·

2021/11/11

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 growing company, it’s Anth. Consider this: Despite being founded less than 10 years ago in 2012, Zumper

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00:18:46

Considerations Unique to Acquiring a Software Company...

In The Trenches ·

2021/10/28

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 acquiror to consider based on my own experience acquiring, running, and selling a small- to medium-sized

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01:17:37

What M&A Lawyers Want CEOs to Know About Selling...

In The Trenches ·

2021/10/14

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 based out of Toronto. From a legal standpoint, Mario has worked with substantially every type of stakeholder

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00:20:36

Lessons From my First Month as the CEO of a Newly...

In The Trenches ·

2021/09/30

In January, 2014, I became the CEO of a software company (after having acquired it from its original founders), powered by all of the wisdom and experience that one would expect from a 27-year-old who had never managed as much as a fruit stand in his entire life. The pace was intense, the volume of information to be processed was overwhelming, and the lessons learned were numerous. In this audio blog, with the benefit of 10 years' worth of hindsight and perspective, I attempt to share with you some

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01:27:00

Rich Manders: Lessons from Founding, Growing, Buying,...

In The Trenches ·

2021/09/16

My guest today is Rich Manders, who has essentially done everything that a CEO and Entrepreneur can do: He has founded companies, operated and grown them substantially, sold them (several times), acquired them (several times), and now acts as a coach for other CEOs and Entrepreneurs looking to do the same. Rich Co-Founded and led iAutomation, a Massachusetts-based machine control and automation company, and grew the company from $0 to $90M in sales with 180 employees. After selling that business to

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00:12:50

Why Your Business Needs a Set of Core Values (or Why...

In The Trenches ·

2021/09/02

Early in my tenure as a CEO, I thought core values were tired, hollow, and meaningless platitudes that companies created simply because they felt they had to. Many of you may view them in a similar light. What I came to learn over time however was that my skepticism towards core values wasn’t because the CONCEPT of them was hollow and meaningless, but instead because so many companies had done such a poor job in establishing theirs, and as a result, their core values BECAME tired platitudes that

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01:04:31

Building and Managing a World Class Product...

In The Trenches ·

2021/08/19

Today’s episode is specific to software companies, and is all about the Product Management operation. As most software executives can attest to, a non-functioning (or worse, a non-existent) product management operation can get companies into all kinds of trouble, and those problems often manifest across Engineering, Sales, Customer Support, and other areas. Some software companies, particularly more mature ones, often start out without a formalized product management discipline, but companies who

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00:23:26

Busting the Biggest Myth About Selling Your Business

In The Trenches ·

2021/08/05

As a business owner, if you're thinking about the sale of your company as being the singular event that will finally eliminate all of the risks that you've personally assumed for so many years, then I hate to be the one to tell you this, but: Think again. Indeed, in my experience, the single biggest myth about selling a company is that the seller bears no further risk after the sale of his or her company is completed. In most cases, especially with respect to the sale of SMBs, this is simply not

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01:21:42

Understanding and Managing The Psychological Toll of...

In The Trenches ·

2021/07/22

In today's episode, I speak with Dr. Eliana Cohen, a Clinical Psychologist who works with (among others) a wide variety of Entrepreneurs and CEOs. Dr. Cohen's practice integrates performance psychology, strategy, emotional intelligence, and knowledge of neuroplasticity and the brain to serve her various clients. In our discussion, we cover a lot of ground including the psychological similarities that Entrepreneurs and CEOs tend to present, how to differentiate between healthy and unhealthy levels of

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00:21:53

Lessons in Managing my own Psychology

In The Trenches ·

2021/07/08

Ben Horowitz, the former CEO of Opsware and now world-renowned Venture Capitalist, once said: “By far the most difficult skill for me to learn as CEO was the ability to manage my own psychology . . . very few people talk about it . . . In the end, this is the most personal and important battle that any CEO will face.” I suspect that almost all entrepreneurs and CEOs know exactly what he meant when he said this. My own experience taught me that unless you are deliberate about managing your own

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01:09:08

CEO Coaches: What do they do, how do they work with...

In The Trenches ·

2021/06/24

In this episode I interview Warren Coughlin, who has been a Coach to SMB CEOs for upwards of two decades, helping them achieve everything from hugely successful exits, to 7-figure salaries, to significantly reduced day-to-day operational roles, and countless other outcomes. Warren is the creator of The Business That Matters Playbook, a tool that streamlines and automates the strategic planning process for CEOs and Entrepreneurs. His coaching practice focuses not only on the business itself, but also

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132 results

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