In The Trenches
Lessons and Reflections From my Experience Acquiring, Operating, and Selling a Small to Medium Sized Business
BUYING A BUSINESS
Busting the Biggest Myth About Purchasing and Operating Small Companies
Listen to This Blog Post In this second edition of our “Myth Busters” series (the first one can be found here), I attempt to debunk a common misconception among prospective acquirors, particularly those looking to purchase a business for the first time. This myth states that the smaller theContinue reading “Busting the Biggest Myth About Purchasing and Operating Small Companies”
Lessons Learned in Capitalizing an Acquisition
Listen to This Blog Post Among the myriad variables that must be carefully considered when acquiring a business is the question of how the acquisition is going to be financed. My intent in the material that follows is not to cover the countless options available to acquirors stemming fromContinue reading “Lessons Learned in Capitalizing an Acquisition”
Considerations Unique to Acquiring a Software Company (Product)
Listen to this Blog Post: In a previous blog post, I discussed several financial considerations unique to acquiring software companies, specifically those of the small-to-medium-sized variety . In this week’s post, I present several non-financial considerations for the prospective acquiror to consider. Much of what I discuss below isContinue reading “Considerations Unique to Acquiring a Software Company (Product)”
Considerations Unique to Acquiring a Software Company (Financial)
Listen to This Blog Post When contemplating the acquisition of a software company (or any company, for that matter), the number of variables that potential purchasers must consider is overwhelming, and as a result it would be impractical to discuss all such variables in a single blog post ofContinue reading “Considerations Unique to Acquiring a Software Company (Financial)”
Lessons From my First Month as the CEO of a Newly Acquired Company
Listen to This Blog Post “Trying to drink from a firehose” is a common expression that is often used to describe a situation in which one has a difficult time processing an overwhelming amount of information within a given period of time. This certainly described my own experience, whenContinue reading “Lessons From my First Month as the CEO of a Newly Acquired Company”
MANAGING YOURSELF
Should You Become an Entrepreneur?
Listen to This Blog Post Within your first-degree network alone, I suspect you know a large number of people who, at one time or another, have expressed a desire to pursue an entrepreneurial career path. Yet I also suspect that, of those people, only a small percentage of them haveContinue reading “Should You Become an Entrepreneur?”
The Entrepreneur and the Spousal Relationship
Listen to This Blog Post It’s no secret that meaningful and fulfilling relationships require deliberate work, often require trade-offs to be made between partners, and possess more than their fair share of peaks and valleys. Though these realities are true of substantially all long-term relationships, they seem to be especiallyContinue reading “The Entrepreneur and the Spousal Relationship”
Lessons in Managing My Own Psychology
Listen to This Blog Post: Ben Horowitz, the world-renowned Venture Capitalist and co-founder of Andreesen Horowitz, said it best when he 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 aboutContinue reading “Lessons in Managing My Own Psychology”
The Entrepreneur and Mental Health (Part 1): My Journey
Listen to this Blog Post: Generally speaking, the average person is not fully aware of the emotional toll that entrepreneurship (or any other type of leadership, for that matter) can take. This could be due to the fact that most leaders tend to be uncomfortable with the idea of vulnerability,Continue reading “The Entrepreneur and Mental Health (Part 1): My Journey”
The Entrepreneur and Mental Health (Part 2): My Advice to You
Listen to This Blog Post: This post is the second in a two-part blog post on leadership and mental health. Before proceeding forward, I suggest that you read Part 1 here. In the now-famous Netflix Documentary “The Last Dance”, which documented Michael Jordan and the dominant Chicago Bulls of theContinue reading “The Entrepreneur and Mental Health (Part 2): My Advice to You”
MANAGING YOUR BUSINESS
A Leader’s Most Important Skill
Listen to This Blog Post Though effective leaders tend to possess a multitude of different skills and abilities, my experience as a CEO taught me that the most important skill for any leader to possess is that of clear and effective communication. Indeed, a CEO’s strategy is only as goodContinue reading “A Leader’s Most Important Skill”
Implementing a Formal Operating System Like EOS or the Rockefeller Habits
Listen to this Blog Post 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 widelyContinue reading “Implementing a Formal Operating System Like EOS or the Rockefeller Habits”
Why Your Company Needs a Set of Core Values (or Why Yours May Not be Having an Impact)
Listen To This Blog Post Particularly in my early years as a CEO, I couldn’t help but roll my eyes whenever somebody suggested that I needed to codify and publish a set of core values for my company. Weren’t core values the tired, hollow, and meaningless platitudes that companies createdContinue reading “Why Your Company Needs a Set of Core Values (or Why Yours May Not be Having an Impact)”
Why So Many Companies Rarely Achieve Their Annual Goals
Listen to This Blog Post: Few things are as energizing as the annual goal-setting process, where the management team decides on the company’s major priorities for the coming year, usually generating a sense of enthusiasm, optimism, and confidence. Conversely, few things are as deflating as the annual review, where theContinue reading “Why So Many Companies Rarely Achieve Their Annual Goals”
Hiring Your Senior Leadership Team
Listen to This Blog Post: There is no single recipe for building a great company, nor is there a definitive formula for becoming a truly effective leader. Anything that you hear or read that suggests otherwise should be treated with a high level of skepticism. Even among the world’s mostContinue reading “Hiring Your Senior Leadership Team”
MANAGING YOUR BUSINESS (SOFTWARE-SPECIFIC)
The Biggest Temptation of a Software CEO
Listen to This Blog Post In his book, The Five Temptations of a CEO, author Patrick Lencioni discusses five areas in which CEOs tend to inadvertently prioritize the wrong things. These “temptations”, as he calls them, can lead to poor decision making at best, and can risk the very survivalContinue reading “The Biggest Temptation of a Software CEO”
Migrating Your Company from On-Premise to SaaS: Part 2
This is the second post in a two-part series on navigating the transition from on-premise to SaaS. You can read Part 1 here. Listen to This Blog Post: In Part 1 of this blog, we evaluated some of the more common challenges that companies face when attempting to migrate bothContinue reading “Migrating Your Company from On-Premise to SaaS: Part 2”
Migrating Your Software Company from On-Premise to SaaS: Part 1
Listen to This Blog Post: The overwhelming majority of software companies founded over the past fifteen years or so have never known anything other than a cloud-based, single-server-multi-tenant architecture coupled with a subscription revenue model. If you’re running a software business that fits this description, then you’ll (thankfully) never needContinue reading “Migrating Your Software Company from On-Premise to SaaS: Part 1”
Pricing Power: How Small Changes Can Have Big Impacts
Listen to This Blog Post: Inertia is defined as something that remains at rest or in uniform motion unless acted upon by some external force. Though software companies can fall prey to inertia in a multitude of ways, one of the most common ways in which inertia manifests is withContinue reading “Pricing Power: How Small Changes Can Have Big Impacts”
SELLING YOUR BUSINESS
Strategic Considerations When Evaluating a Letter of Intent to Sell Your Business
Listen to This Blog Post For many business owners (particularly those actively looking to sell their companies), few things are as exciting as receiving a Letter of Intent (“LOI”) from a prospective purchaser. Beyond the sense of personal validation stemming from the fact that a sophisticated counterparty sees an assetContinue reading “Strategic Considerations When Evaluating a Letter of Intent to Sell Your Business”
The Working Capital Adjustment
Listen to This Blog Post In a previous blog post, Busting the Biggest Myth About Selling Your Business, we reviewed a number of fundamental facts related to the sale of any company that warrant being repeated here: The single biggest myth about selling a company is that the seller bearsContinue reading “The Working Capital Adjustment”
Busting the Biggest Myth About Selling Your Business
Listen to This Blog Post The entrepreneurial journey is full of innumerable risks: Your largest customers can leave at any time, and for any reason. The market may change faster than your company’s ability to adapt. Your largest supplier may decide to cut you out of the value chain andContinue reading “Busting the Biggest Myth About Selling Your Business”
Considerations in Selecting Your M&A Advisor
Listen to This Blog Post: Many entrepreneurs cite the exit process as being one of the most difficult, time consuming, and emotionally trying experiences of their lives. The reality of selling a company stands in stark contrast to the manner in which it’s often portrayed in the media, where theContinue reading “Considerations in Selecting Your M&A Advisor”
What I Learned During my First (Failed) Attempt to Sell my Business
Listen to This Blog Post: “You think running a business is hard? Try selling one”. That’s what one of my mentors said to me when I approached him in 2017 with the idea of selling my business the following year. His goal wasn’t to dissuade me from pursuing an exit,Continue reading “What I Learned During my First (Failed) Attempt to Sell my Business”
anxiety (4) burnout (4) buying a business (13) CEO time and emotion (8) communication (6) compensation structure (6) core values (6) culture (4) customers (7) deal terms (10) depression (2) disruption (2) financing (10) focus (5) goal setting (4) growth (8) hiring (10) HR (6) imposter syndrome (4) incentives (7) LOIs (7) M&A (16) M&A advisor (7) management team (6) meditation (3) mental health (8) metrics (3) onboarding (2) perfectionism (2) pricing (6) product management (5) profitability (7) SaaS (7) salaries (3) sales (2) sales compensation (3) self care (12) selling a business (6) software (8) spouses and partners (2) stoicism (2) strategy (3) time management (7) transparency (5) valuation (7)
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