In The Trenches

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!

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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 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!

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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, 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. 

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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.  

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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.

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.

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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!  

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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!

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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!

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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!

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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.

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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 :)