Hard to Kill: A Four-Part Framework for Evaluating Small Business Acquisitions

As I’ve transitioned from operator to investor over the past 5 years or so, I’ve attempted to develop a general philosophy to guide my decision making, given that almost every investment decision seems to present me with a long list of reasons to be simultaneously hopeful and terrified. The four-point framework that I outline in this week's blog post is my attempt to add some structure and objectivity to these decisions. I’m not so vain as to think that my investment philosophy is one that ought to be emulated or studied by others (quite the opposite, in fact: I am a work-in-progress at best, and a complete novice at worst). Instead, I’ve decided to present this framework in hopes that: (1) Searchers might benefit from it as they evaluate potential targets without the years of context and hundreds of repetitions that are typically required to calibrate a sense of what makes for an attractive opportunity vs. a less attractive one; & (2) To keep myself honest, and to create a single place for me to go whenever I feel like I may be deviating from an investment philosophy that makes intuitive sense to me The four primary ideas that I outline include positive asymmetry, the avoidance of existential risks, protecting downside over maximizing upside, and targeting businesses that are "hard to kill". Though such a strategy may sound overly defensive, I do my best to argue that: (1) Achieving "tail" outcomes isn’t necessarily the result of taking unduly risky bets; & (2) While risk and return do indeed tend to be inversely correlated, one shouldn’t assume that higher risk bets necessarily suggest the opportunity for higher rewards. Sometimes, risky is just risky. Please enjoy! https://mineolasearchpartners.com/2025/12/11/hard-to-kill-a-four-part-framework-for-evaluating-small-business-acquisitions/