In The Trenches

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 :)

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 :)

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 :)

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 :)

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 :)

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 :)

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 :)

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 :)

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 :)

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!