In The Trenches

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 b...

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 automat...

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 suc...

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 mo...

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...

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 similari...

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 mean...

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 pro...

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...

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...

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 c...

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...

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,...

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...

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 mak...

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...

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...

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...