Skip to main content
In The Trenches

In The Trenches

By Steve Divitkos
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 single goal: To improve the personal and professional lives of Entrepreneurs and CEOs running SMBs.
Where to listen
Apple Podcasts Logo

Apple Podcasts

Google Podcasts Logo

Google Podcasts

Pocket Casts Logo

Pocket Casts

RadioPublic Logo


Spotify Logo


Currently playing episode

Running a Business During Inflationary Periods and Understanding Pricing Power (with Jim Sharpe)

In The Trenches

Running a Business During Inflationary Periods and Understanding Pricing Power (with Jim Sharpe)

In The Trenches

Running a Business During Inflationary Periods and Understanding Pricing Power (with Jim Sharpe)
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 to inflationary pressures, and finally how they should deal with vendors who attempt to pass through price increases to them. Jim has been at at the Harvard Business School since 2009, holding positions as a Senior Lecturer in the MBA and Executive Education programs, an Entrepreneur in Residence, and now serves as a Visiting Executive. In 1987, Jim purchased Extrusion Technology, an aluminum extrusion fabricator that he ran as CEO for over 20 years. In 2008, Jim sold the company to a private equity firm, having grown the company from $4MM to $32MM in revenue throughout his ownership tenure. Jim is now an active investor in small and medium sized businesses, holding ownership positions in more than 50 entrepreneurial companies.
June 23, 2022
The Biggest Temptation of a Software CEO
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!
June 09, 2022
Employee Burnout and The Great Resignation
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!
May 26, 2022
Should You Become an Entrepreneur?
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!
May 12, 2022
Having Hard Conversations (Live Panel Discussion from 2022 MIT Sloan Search Fund Summit)
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!
April 28, 2022
A Leader’s Most Important Skill
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!  
April 14, 2022
Quality of Earnings Analysis: What You Need to Know Before Buying a Business
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 others. Chris and I discuss what a QofE is, why it's necessary, and common trends and themes that buyers should look out for. We also discuss the working capital adjustment: What it is, why it's necessary, and common pitfalls for both buyers and sellers to avoid. Please enjoy! 
March 31, 2022
Lessons Learned in Capitalizing an Acquisition
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!
March 17, 2022
Aaron Ross: Author of "Predictable Revenue" and "From Impossible to Inevitable"
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 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, the world’s #1 resource for SaaS entrepreneurs), which is a "hypergrowth playbook" based on the successes of companies like Twilio, HubSpot, Marketo, and 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.
March 03, 2022
The Entrepreneur and the Spousal Relationship
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!
February 17, 2022
Bob Pritchett: Author of "Fire Someone Today" and Founder & Executive Chairman of Faithlife Software
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!
February 03, 2022
The Working Capital Adjustment
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 you don't like the idea of having to wire money back to your buyer after they've wired you the money to purchase your company, then this episode is for you.  
January 20, 2022
All Things Hiring with Randy Street: Co-Author of " Who: The A-Method for Hiring" and Vice Chairman of ghSMART
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 on my radar when I read the book that he wrote in collaboration with ghSMART’s chairman and founder, Geoff Smart, called Who: The A Method for Hiring. I profile this book on my website as being absolutely required reading for all entrepreneurs and CEOs running SMBs. The very specific hiring method that they detail within this book changed the way that I made all of my hires across my entire company. The book quickly become a New York Times, Wall Street Journal, BusinessWeek, USA Today, and Publishers Weekly best seller, and has earned acclaim from countless other publications. Randy also co-authored another Wall Street Journal bestseller, called Power Score: Your Formula for Leadership Success. In our discussion today, we barely touch on Randy’s book because, candidly, I’d encourage you to simply buy it an read it for yourself. In today’s episode, I try to dig one level deeper with Randy and discuss how to evaluate people & teams that you haven’t personally hired, post-hire considerations, lessons from 30+ years of working with CEOs and management teams, compensation, and how to identify and address conflicts within leadership teams. Please enjoy!
January 06, 2022
Considerations Unique to Acquiring a Software Company (Product)
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 to operate and grow. In this way, what start out as technical problems quickly accumulate to become significant business problems. Thus, prospective acquirors would be well served to thoroughly diligence the amount of technical debt possessed by any given target company, and proceed very carefully (or perhaps not proceed at all) with those companies who seem to possess much more than their fair share of it. We break our analysis down into high risk, medium risk, and low risk signs. Enjoy! 
December 23, 2021
Verne Harnish: Founder of The Entrepreneurs' Organization (EO), Author of "Scaling Up" and "Mastering the Rockefeller Habits"
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 Up, a global executive education and coaching company with over 200 partners on six continents. Verne may be best known for being the author of multiple global bestselling books including Mastering the Rockefeller Habits; The Greatest Business Decisions of All Time (for which Jim Collins wrote the foreword); Scaling Up (Rockefeller Habits 2.0) (which has been translated into 23 languages and has won eight major international book awards including the prestigious International Book Award for Best General Business book); and his latest book, Scaling Up Compensation. In our chat today we cover a wide range of topics starting with compensation, and then moving to hiring, managing one’s self, and a bit of a mixed bag at the end. We also conclude with the 3-5 books that Verne would put on his Mount Rushmore of business books, so if you’re a reader, be sure to stay tuned for that one.
December 09, 2021
Implementing a Formal Operating System Like EOS or the Rockefeller Habits
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 implemented an operating system (EOS) in my own company beginning in 2015, and we continued to operate under its various principles and structures until successfully selling the company in late 2020. Though a formal operating system likely isn’t appropriate for all companies and all circumstances, we benefited tremendously from our own implementation. Based on that first-hand experience, in today's audio blog I share a number of FAQs that I often receive from other CEOs related to the implementation of a formal operating system within a SMB. 
November 25, 2021
The Realities of Managing Extremely Rapid Growth
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 now boasts over 250 employees and 75 million active users, making it the biggest residential rental platform in North America. Since founding Zumper, Anth has raised over $150M in Venture Capital funds from a roster of VCs that would likely make many of his Silicon Valley CEO peers envious, including Andreessen Horowitz, Greylock, Kleiner Perkins, and Blackstone, among others.  Since its founding, Zumper has regularly grown at triple-digit growth rates, which of course has presented Anth with both problems and opportunities that some CEOs simply haven’t had to deal with. Among other things, in our discussion today we talk about the tradeoff between raising growth capital and dilution of his personal ownership stake, how he thinks about how much money to raise at any given time, his views on organic versus inorganic growth (and his experience managing both), the systems and processes that often break in the face of high growth, how growth has impacted his hiring and retention strategies, and lastly how managing an ultra-high growth company has impacted Anth personally.  If you run a company that is growing at any pace, I hope and trust that you’ll leave with at least a few nuggets of wisdom that will help you along your own journey.
November 11, 2021
Considerations Unique to Acquiring a Software Company (Financial)
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 software company over the course of many years. Specifically, for every topic that I profile, I discuss why it’s important to dig one level deeper than the simple “headline” numbers or conclusions. In this audio blog I will discuss only financial considerations, while in my next episode, I will discuss non-financial considerations. Enjoy! 
October 28, 2021
What M&A Lawyers Want CEOs to Know About Selling Their Companies
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 within the SMB ecosystem (business owners, CEOs, entrepreneurs, strategic acquirers, private equity firms, banks, non-bank lenders, financial advisors, deal intermediaries, and so on), and regularly acts for both buyers and sellers in both minority and majority SMB sales.  We cover a lot of ground in our discussion, and focus specifically on the most common blind spots that Entrepreneurs and CEOs tend to exhibit when it comes to selling their companies, including:  The most common reason why entrepreneurs over-pay in taxes after receiving their deal proceeds; How to select legal counsel when looking to sell your business, and how much you should expect it to cost; Whether LOIs should be detailed or generic, and why; The circumstances under which buyers and sellers would prefer an asset sale or a share sale; The most frequent mistakes business owners make when negotiating representations & warranties in the purchase agreement; Why rep & warranty insurance is growing as a useful tool for both buyers and sellers; How to deal with unsophisticated legal counsel & advisors in a SMB sale; The top 3 reasons why deals fall apart after a LOI is signed; How to negotiate your non-compete; You can access the show notes by clicking on this link  Please enjoy! 
October 14, 2021
Lessons From my First Month as the CEO of a Newly Acquired Company
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 of the major lessons and observations gleaned from my few months as the CEO of a newly acquired small business, in hopes that you can utilize some of them should you ever find yourself in a similar situation. 
September 30, 2021
Rich Manders: Lessons from Founding, Growing, Buying, Selling, Coaching, and Investing in SMBs
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 The Riverside Company (a leading global Private Equity firm), Rich stayed on with the business, and alongside his partners at Riverside, he grew the company by a factor of 6x, resulting in a 50%+ IRR to his original investors after its next sale to Saw Mill Capital.  Alongside Riverside, Rich has played a key role in seven completed acquisitions and has evaluated dozens of others from the perspective of both a buyer and a seller. Rich has Board experience across several different private companies, and alongside his business partner, now runs Freescale Coaching, where he coaches entrepreneurs and CEOs and helps them grow their business beyond their wildest dreams.   Rich’s entrepreneurial success story is the subject of a Harvard Business School case study, which is where I was first introduced to him in my second year of study there. Since then, Rich has taught several courses and seminars at Harvard, among other leading business schools. He relies on his decades of experience as an Entrepreneur and CEO to inform his structured, systematic, repeatable, and process-oriented approach to growing world-class private companies.  Please enjoy!    
September 16, 2021
Why Your Business Needs a Set of Core Values (or Why Yours May Not be Having an Impact)
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 nobody paid attention to. We eventually came to view our core values as a small set of vital and timeless guiding principles for our company, that defined our culture and our people, both as individuals and as a team. We used them to add a sense of clarity to everything that we did within our organization, including to attract like-minded people, to reward, recognize and appreciate existing employees, and to make more objective hiring, promotional and other personnel-related decisions. If your company doesn't currently have any core values established, (or you do, and they're lacking any real world impact), then this episode is for you. I discuss several of the primary lessons that we learned over the years to make our values truly meaningful.
September 02, 2021
Building and Managing a World Class Product Management Discipline
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 pursue any degree of scale often quickly realize just how critically important this discipline is.  My guest today is Rich Mironov, who is one of North America's preeminent Product Management thought leaders. He has spent 40 years in the software industry in numerous capacities, and currently acts as a Coach, Consultant, and Interim Executive for CEOs and Heads of Product across Canada and the United States, advising them on a diverse range of issues spanning product, marketing, engineering, and sales. Rich has led Product Management at six start-ups, and has now consulted for more than 170 technology companies of all sizes. He is the author of "Product Bytes", a hugely popular and long-running blog on software, start-ups, product strategies, Silicon Valley, and the inner life of product managers. Rich is also the author of the book, “The Art of Product Management”.  Our conversation covers a lot of ground including hiring a Product leader and Product team, how to think about prioritizing products/features/functions, how Product should interface with Sales and other internal departments, how involved CEOs should be in Product, and what fatal mistakes he’s seen Product Managers make. Please enjoy!
August 19, 2021
Busting the Biggest Myth About Selling Your Business
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 true.  In this audio blog, I will share with you some of the more common ways in which sellers may still bear some risk (in some cases, material risk) even after the consummation of the sale transaction. Though this list isn’t an exhaustive one, you should expect to encounter at least some of these sources of risk when the time comes time for you to sell your own business, so it’s worth educating yourself on them from now. As it relates to certain of these risks, I also share certain tools and strategies to eliminate or mitigate these risks as best as possible.  
August 05, 2021
Understanding and Managing The Psychological Toll of Being an Entrepreneur or CEO
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 worry and/or anxiety, how leaders tend to conflate their own happiness with the success of their businesses, signs to watch that may suggest that mental health is suffering, how to find a therapist, books to read, and much more. Please enjoy!    ********************   If this episode provided you with value, would you mind leaving a rating and/or review wherever you access your podcasts? Ratings and reviews help me secure guests that would otherwise be difficult to obtain, and it is exactly these types of people that I want each of you to learn from. Any ratings and/or reviews would be much appreciated
July 22, 2021
Lessons in Managing my own Psychology
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 psychology as a leader, you risk becoming a sort of “victim” to the circumstances that happen to present themselves in your life at any given time.   Against this backdrop, in this audio blog I share the five most meaningful lessons that I’ve learned over the years related to better managing my own psychology as a leader. Though many of these lessons are easier said than done, I suspect that any degree of time and effort that you dedicate towards them will likely yield meaningful results. They include 1) The perils of comparing ourselves to others, 2) Focusing only on what you can control, 3) The value of better understanding yourself, 4) The price of untethered levels of ambition, and 5) How to deal with "first world" problems.  Though mastery of these subjects is something that will likely elude all of us, improvement is probably much easier to attain than you may think.  ********************  If this episode provided you with value, would you mind leaving a rating and/or review wherever you access your podcasts? Ratings and reviews help me secure guests that would otherwise be difficult to obtain, and it is exactly these types of people that I want each of you to learn from. Any ratings and/or reviews would be much appreciated :)  
July 08, 2021
CEO Coaches: What do they do, how do they work with CEOs, and why might you consider hiring one?
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 on the entrepreneur at a personal level, working with them to ensure that they craft meaningful values and live a lifestyle that is meaningful and fulfilling to them.  In this episode we cover a wide array of topics, some of which include: What do CEO coaches actually do? What does a typical coaching engagement look like? When is an appropriate time to hire a coach, if you hire one at all? How much do coaches cost, and how should CEOs think about the ROI on that investment? How does one even go about looking for a coach? How much of the coaching process is focused on the business vs. on the entrepreneur themselves? What are some of the most common areas for improvement that you witness when first engaging with a new CEO client? When should you fire your CEO coach? And countless others.  Please enjoy! ******************** If this episode provided you with value, would you mind leaving a rating and/or review wherever you access your podcasts? Ratings and reviews help me secure guests that would otherwise be difficult to obtain, and it is exactly these types of people that I want each of you to learn from. Any ratings and/or reviews would be much appreciated :)
June 24, 2021
Migrating Your Software Company from On-Premise to SaaS (Part 2)
In Part 1 of this Audio Blog, we evaluated some of the more common challenges that companies face when attempting to migrate both their product and revenue models from that of on-premise to SaaS.  I guided my own company through this transition over many years. Though we did end up achieving some success, our transition ultimately went too slow, required too much time and capital, and came in below our initial targets. In this Audio Blog (Part 2), I leverage this first-hand experience to walk you through the tactics and strategies that you can put into place to make your own transition faster, cheaper, and ultimately less painful than mine was. These include things that we did (that worked), as well as things that we didn’t do (that I wish we had). Enjoy! ******************** If this episode provided you with value, would you mind leaving a rating and/or review wherever you access your podcasts? Ratings and reviews help me secure guests that would otherwise be difficult to obtain, and it is exactly these types of people that I want each of you to learn from. Any ratings and/or reviews would be much appreciated :)
June 10, 2021
What I Learned During my First (Failed) Attempt to Sell my Business
As CEOs, many of you are undoubtedly considering the possibility of selling your business at some point in the future.  In 2018, I attempted to sell my own business, though was unsuccessful in doing so. From start to finish, the sale process took upwards of 12 grueling months. Hundreds of potential suitors were narrowed down to a dozen or so, which in turn were narrowed down to a single acquiror with whom we completed the extensive financial, legal, technical, and commercial due diligence process.  Just as we were beginning to draft the final purchase agreement, the transaction fell apart. At the time, this felt like a big personal failure. I felt as if I had spent a full calendar year pushing myself to the brink of exhaustion with nothing to show for my efforts. With the benefit of time however, I’ve come to realize how enormously valuable this experience was. Indeed, without the knowledge and experience that we had acquired, we almost certainly would not have successfully sold the business in 2020.  In this Audio Blog, I share with you some of the major lessons that I learned during my first (unsuccessful) attempt at selling my company. I hope you’ll find them to be useful.  ******************** If this episode provided you with value, would you mind leaving a rating and/or review wherever you access your podcasts? Ratings and reviews help me secure guests that would otherwise be difficult to obtain, and it is exactly these types of people that I want each of you to learn from. Any ratings and/or reviews would be much appreciated :)
June 04, 2021
Considerations in Selecting Your M&A Advisor
As CEOs & Entrepreneurs, I suspect many of you have at least considered the possibility of an exit, whether it be in the near or long-term future. In my experience selling my own business, the selection of my M&A Advisor was perhaps one of the most important decisions that I had to make, and in retrospect so many other decisions (and their outcomes) flowed directly from this one critical choice. I once chose a bad advisor, and have since worked with a great one. Based on these experiences, I have an enhanced appreciation for the specific variables that I think are important to consider when making this critical decision.     Today’s Audio Blog explains each variable that I think you should consider in selecting your own M&A Advisor, in hopes that you will be able to benefit from my lessons without having to experience the heartache that led to them in the first place! ******************** If this episode provided you with value, would you mind leaving a rating and/or review wherever you access your podcasts? Ratings and reviews help me secure guests that would otherwise be difficult to obtain, and it is exactly these types of people that I want each of you to learn from. Any ratings and/or reviews would be much appreciated :)
June 02, 2021
Pricing Power: How Small Changes Can Have Big Impacts
As CEOs & Entrepreneurs, we all know that there are a countless number of levers that one can pull to grow revenue or profitability, all of which will have varying degrees of impact. Increasing prices is one such lever, however it is somewhat unique. In this audio blog, I explain why. I argue that in certain circumstances, raising the prices that you charge to existing customers is one of the fastest, most effective, and “lowest friction” ways to unlock a nascent revenue and profitability opportunity that may reside within the base of customers that you already possess. It isn’t the right strategy for all companies, but it almost certainly is for some. If you haven’t revisited your pricing in 1-2+ years, then there’s at least a possibility that incremental revenue and profitability are being left on the table. Though this Audio Blog does touch specifically on software companies at times, it's important to note that the insights contained within can be applicable to substantially any business that engages in repeat sales with existing customers, be it within a subscription revenue model or not. ******************** If this episode provided you with value, would you mind leaving a rating and/or review wherever you access your podcasts? Ratings and reviews help me secure guests that would otherwise be difficult to obtain, and it is exactly these types of people that I want each of you to learn from. Any ratings and/or reviews would be much appreciated :)
May 30, 2021
The Private Equity Perspective on Acquiring, Operating, and Selling Software Companies
My guest today is Jordan Bettman. Jordan is a Partner and Co-founder of Radian Capital, a New York-based Private Equity firm focused on B2B software and technology-enabled services businesses. Radian currently has ~$500 million of assets under management, and is now investing out of their second fund. Prior to co-founding Radian, Jordan was a Partner at Bain Capital Ventures for nearly a decade, where he focused largely on financial services and back-office technology investments. He currently serves on the Board of Directors of 5 private technology businesses, and through Radian has made direct investments (both majority and minority) in dozens more. Jordan received his MBA from Harvard Business School and his B.S. from Cornell University. Jordan & I discuss a wide range of topics (some specific to software, others around M&A more broadly), including how he evaluates software companies, how CEOs should evaluate potential acquirors, the pros and cons to CEOs of selling in a sellers' market, why deals fail, how to best align interests of buyers and sellers, and expectations of CEOs after they sell their company.  Please enjoy!   ******************** If this episode provided you with value, would you mind leaving a rating and/or review wherever you access your podcasts? Ratings and reviews help me secure guests that would otherwise be difficult to obtain, and it is exactly these types of people that I want each of you to learn from. Any ratings and/or reviews would be much appreciated :)
May 27, 2021
Migrating Your Software Company from On-Premise to SaaS (Part 1)
Today’s audio blog is specific to software, and concerns the migration from i) a business model characterized by on-premise hosting and one-time perpetual-use licensing fees, to ii) a new business model characterized by cloud-based hosting and a subscription licensing. This process is generally referred to as the "On-Premise to SaaS Migration". Most software companies founded over the past fifteen years or so have never known anything other than the latter model, however, for anybody running a company still selling on-premise software under a perpetual-use pricing model (or is considering investing in one) , I'd humbly suggest that you listen to this episode. In this post, I lean on my first-hand experience in making this transition to describe some of the factors that make it so difficult.  In my next post, I will share with you the tactics and strategies that worked (and didn’t work) for me to overcome some of these challenges, so that you can drastically increase your own odds of success should you decide to make this leap yourself. Enjoy! ******************** If this episode provided you with value, would you mind leaving a rating and/or review wherever you access your podcasts? Ratings and reviews help me secure guests that would otherwise be difficult to obtain, and it is exactly these types of people that I want each of you to learn from. Any ratings and/or reviews would be much appreciated :)
May 26, 2021
Hiring Your Senior Leadership Team
In my experience as a CEO, I came to learn that surrounding myself with A+ people (particularly at the senior leadership team level) was one of the most impactful things that I could do for both myself and my company. Even if you are above average with respect to your ability to hire great people (most people think that they are – yet most people are not), it is a virtual guarantee that you'll make some mistakes as you build out your leadership team.  I certainly did. It took me many years (and many mistakes) to learn about great hiring practices. To prevent you from making some of those same mistakes, in this Audio Blog I’ve compiled a list of the major lessons that I learned while hiring my own executive team over many years.  Enjoy! ******************** If this episode provided you with value, would you mind leaving a rating and/or review wherever you access your podcasts? Ratings and reviews help me secure guests that would otherwise be difficult to obtain, and it is exactly these types of people that I want each of you to learn from. Any ratings and/or reviews would be much appreciated :)
May 17, 2021
Why So Many Companies Rarely Achieve Their Annual Goals
Today’s episode is all about execution, and more specifically what you need to do to give yourself the best odds of actually executing on the goals that you set for your organization.  There’s a well-known maxim that you might be familiar with that states “Strategy without execution is hallucination”, and in today’s audio blog I’ll share with you why I think that’s true. I’ll do so by sharing some of the lessons that I’ve learned over the years related to executing on the strategy you set. In my experience (and in the experience of countless others), strategy is actually the easy part: Almost any mediocre CEO can set logical and compelling goals for a company, but it’s the truly skilled CEO who adjusts her tools, systems and processes to regularly and successfully execute on those same goals.  As Jim Collins and Jerry Porras (authors of the seminal business book Built to Last) said: “Building a visionary company requires one percent vision and 99 percent alignment.” Today, I’ll share with you the best tools that I’m aware of to create that alignment.  I hope you enjoy! ******************** If this episode provided you with value, would you mind leaving a rating and/or review wherever you access your podcasts? Ratings and reviews help me secure guests that would otherwise be difficult to obtain, and it is exactly these types of people that I want each of you to learn from. Any ratings and/or reviews would be much appreciated :)
May 17, 2021
The Entrepreneur and Mental Health (Part 2): My Advice to You
In today's post, I share with you the lessons I’ve learned to deal with (or prevent, as much as possible) the mental health toll that entrepreneurship (or leadership, or success) can take: Of course, these lessons are only now clear to me with the benefit of hindsight vision being of the 20/20 variety. When you’re constantly in the trenches, like so many Entrepreneurs and CEOs are, it’s difficult to see the forest from the trees. For this reason, I hope you’ll find this Audio Blog to be highly practical, and full of strategies that you can actually employ in your own day-to-day life. ******************** If this episode provided you with value, would you mind leaving a rating and/or review wherever you access your podcasts? Ratings and reviews help me secure guests that would otherwise be difficult to obtain, and it is exactly these types of people that I want each of you to learn from. Any ratings and/or reviews would be much appreciated :)
May 13, 2021
The Entrepreneur and Mental Health (Part 1): My Journey
In this Audio Blog, I provide you with a brief summary of my own mental health journey as a leader. My goal isn’t to provide you with an exhaustive account of my journey, but rather to simply discuss it publicly. After all, if I don’t do my own part to contribute to the discussion around the worries, thoughts, and fears that Entrepreneurs and CEOs face, what right do I have to lament that it isn’t being discussed enough more broadly? This will be my only Audio Blog solely about me. Though it may be less practical for you than other posts, I hope you’ll agree that it’s still worth listening to nonetheless. Perhaps you will see some of yourself in the feelings, worries, and anxieties that I experienced.  ******************** If this episode provided you with value, would you mind leaving a rating and/or review wherever you access your podcasts? Ratings and reviews help me secure guests that would otherwise be difficult to obtain, and it is exactly these types of people that I want each of you to learn from. Any ratings and/or reviews would be much appreciated :)
May 13, 2021
Sales: Hiring, Onboarding, Compensating, Scaling & Supporting a World Class Sales Team
In this episode I interview Dave Prusinksi, currently the Chief Revenue Officer at SafeAI, a hyper-growth silicon valley company in the autonomous vehicle space. Here is why I think Dave is a person worth listening to:  Prior to his current role, Dave spent 10 years as the Executive Vice President of Sales and Marketing at FleetComplete, a technology provider to fleet-owning businesses around the world. Under Dave's leadership, FleetComplete grew from $6M ARR to $150M in total revenue, achieving an average 50% revenue CAGR for 9 of his 10 years.   Dave played an integral role in the acquisition of 6 companies, leading the sales and marketing due diligence processes, and ultimately integrating the operations of the acquired businesses into that of FleetComplete.   In addition to acquiring and investing in SMBs for FleetComplete, Dave was also a central member of the deal team helping to lead FleetComplete through multiple investment and acquisition rounds themselves, managing the sales & marketing due diligence processes in each instance.   Dave has served as a Revenue Coach to several SMBs, working directly with their CEOs and Heads of Sales to optimize their sales and revenue generation processes. All of the companies with whom Dave has worked thus far have now exited with great success.   Prior to FleetComplete, Dave was the National Sales Manager at Research in Motion, where he jointly grew and managed one of the largest divisions with over $1B dollars in annual revenue. Dave and I cover a wide range of topics specific to sales, including: Hiring and onboarding sales leaders and individual reps, how to best craft incentive compensation plans, how to manage team attrition, how and when to build out other internal functions that support the Sales team, how and when to scale a team via additional headcount, and what sales metrics he thinks are most important for CEOs to keep their eyes on. Please enjoy!
April 29, 2021
April 19, 2021
April 19, 2021