In The Trenches

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! 

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.

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!    

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.

Rich Mironov, a Product Management thought leader with 40 years in the software industry, shares invaluable insights on building a world-class product management discipline. He discusses the critical role of effective hiring practices for product leaders and emphasizes the importance of aligning sales with product management. Rich also navigates product roadmapping, balancing immediate needs with long-term vision, and the strategic decision-making between building in-house solutions versus purchasing from vendors. His experience offers vital lessons to technology companies striving for success.

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.

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

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 :)  

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 :)

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 :)