In The Trenches

All Things Hiring with Randy Street: Co-Author of " Who: The A-Method for Hiring" and Vice Chairman of ghSMART

Today’s episode is all about Hiring, and we’ve managed to secure one of the world’s foremost experts on the subject. My guest is Randy Street. Randy is Vice Chairman of ghSMART , which is a global consulting firm that helps CEOs, boards, and investors build valuable companies specifically through hiring and developing world class leadership teams. During Randy's tenure, ghSMART has grown tenfold, and has been ranked by Forbes as one of America’s Best Consulting Firms from 2017-2020. Randy first ...

Considerations Unique to Acquiring a Software Company (Product)

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 inten...

Verne Harnish: Founder of The Entrepreneurs' Organization (EO), Author of "Scaling Up" and "Mastering the Rockefeller Habits"

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 Sca...

Implementing a Formal Operating System Like EOS or the Rockefeller Habits

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 impl...

The Realities of Managing Extremely Rapid Growth

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, Zump...

Considerations Unique to Acquiring a Software Company (Financial)

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 so...

What M&A Lawyers Want CEOs to Know About Selling Their Companies

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 stakehol...

Lessons From my First Month as the CEO of a Newly Acquired Company

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 s...

Rich Manders: Lessons from Founding, Growing, Buying, Selling, Coaching, and Investing in SMBs

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...

Why Your Business Needs a Set of Core Values (or Why Yours May Not be Having an Impact)

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...

Building and Managing a World Class Product Management Discipline

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 more mature ones, often start out without a formalized product management discipline, but companies wh...

Busting the Biggest Myth About Selling Your Business

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...

Understanding and Managing The Psychological Toll of Being an Entrepreneur or CEO

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 level...

Lessons in Managing my own Psychology

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 ps...

CEO Coaches: What do they do, how do they work with CEOs, and why might you consider hiring one?

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 ...

Migrating Your Software Company from On-Premise to SaaS (Part 2)

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...

What I Learned During my First (Failed) Attempt to Sell my Business

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...

Considerations in Selecting Your M&A Advisor

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 experience...

Pricing Power: How Small Changes Can Have Big Impacts

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 op...

The Private Equity Perspective on Acquiring, Operating, and Selling Software Companies

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 ...

Migrating Your Software Company from On-Premise to SaaS (Part 1)

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 c...

Hiring Your Senior Leadership Team

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 m...

Why So Many Companies Rarely Achieve Their Annual Goals

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 ...

The Entrepreneur and Mental Health (Part 2): My Advice to You

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 p...

The Entrepreneur and Mental Health (Part 1): My Journey

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...

Sales: Hiring, Onboarding, Compensating, Scaling & Supporting a World Class Sales Team

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 ...

In The Trenches (Trailer)