In The Trenches

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!

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.

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.

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.

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!

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.