Journal · May 29, 2026 · 2 min read

How we evaluate a software business before we build or buy

We evaluate software businesses with a focus on durability, revenue, retention, margins, and AI leverage.

The Foundation of Our Evaluation

When we evaluate a software business, we focus on several key metrics. Our approach is systematic and thorough because we aim to build or acquire companies with staying power. The first step is to ensure that the problem the software addresses is durable. A durable problem outlasts passing trends. It persists over time and across varying market conditions.

Take Elder Voice, for instance. The need for companionship among the elderly isn't tied to a fleeting moment. It's a consistent requirement, driven by demographic trends and societal changes. That makes it a perfect candidate for our model. Similarly, JellyPal addresses a growing need for medication management as more people use GLP-1 medications.

Revenue and Retention

Next, we look at revenue models. We prefer businesses with recurring revenue. This could be through subscriptions or long-term contracts. Recurring revenue provides stability and predictability, which is crucial for planning and scaling operations.

Retention rates offer another window into business health. High retention rates indicate customer satisfaction and the software's integral role in users' lives or businesses. We analyze churn rates and customer lifetime value to assess this.

Margins Matter

We also scrutinize profit margins. A business with healthy margins has more room to maneuver in terms of growth and investment. We examine cost structures to understand where efficiencies can be gained. High margins suggest a business is well-positioned to reinvest profits into further growth without the need for constant funding rounds.

The AI Leverage Test

AI leverage is a crucial aspect of our evaluation. We assess how artificial intelligence can enhance the business model. Can AI streamline operations? Improve customer interactions? Increase efficiency? These are questions we ask because AI integration can significantly boost a company's scalability and appeal.

For example, Elder Voice uses AI to provide seamless interactions, making it an indispensable companion for the elderly. This AI-driven approach enhances user experience while keeping operational costs low.

Simplicity and Optional Capital

We believe in simplicity. A business model that's too complex can become a burden rather than an asset. We look for businesses with straightforward models that are easy to manage and scale. This involves understanding the core operations and identifying potential bottlenecks or inefficiencies.

Another factor is the optionality of capital. We prefer ventures that don't require constant injections of capital to stay afloat. Instead, they should have the capacity to grow independently, with additional capital used as a lever rather than a lifeline.

Putting It All Together

Our checklist is a tool to ensure we acquire or build software companies that align with our philosophy of durability and efficiency. This process allows us to maintain focus and direction, ensuring that our ventures like Elder Voice and JellyPal thrive in their respective markets.

By sticking to these criteria, we achieve a balance between innovation and practicality. It's a disciplined approach that has served us well, enabling us to create and sustain successful software businesses.