In The Trenches


Lessons and Reflections From my Experience Acquiring, Operating, and Selling a Small to Medium Sized Business

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BUYING A BUSINESS

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)”


MANAGING YOURSELF

How to Know When it’s Time to Quit

Listen to This Blog Post Paradox (par·​a·​dox | per-ə-ˌdäks): A seemingly self-contradictory statement or proposition that, when investigated or explained further, may prove to be well founded or true One needn’t look terribly deep within entrepreneurial folklore to be regaled with stories about the importance of persistence to the entrepreneurial journey, includingContinue reading “How to Know When it’s Time to Quit”


MANAGING YOUR BUSINESS

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)”


MANAGING YOUR BUSINESS (SOFTWARE-SPECIFIC)

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”


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”