The 2025 Return on Security Year-End Letter

The second installment of this letter comes to you as part of an annual series I’ve implemented at Return on Security. It’s one part self-reflection, and one part ode to Warren Buffett and his famous Berkshire Hathaway shareholder letters.

As another Blockbuster year in the cybersecurity industry winds down, I wanted to take the time to share a few updates on the business of Return on Security and offer additional commentary on how I’m thinking going into 2026. My goal is to communicate with you as if you were an active investor in Return on Security, and in a manner I’d like to receive if the positions were reversed.

For those of you wondering what's happening with Return on Security behind the scenes or how I've been making this work, this letter is for you.

While 2024 marked the leap to doing Return on Security full-time, 2025 was the real test. This was the “make it or break it” year.

2025 was the first full year of trying to thrive solely through the work I do at Return on Security.

To help you understand the business behind the scenes, it’s best to view Return on Security as a universe composed of distinct “worlds.” The goal is to ensure that every minute spent and every dollar invested result in the highest possible level of real, lasting meaning and growth.

This is the most established and well-known asset in the Return on Security universe. What started as a simple newsletter from a Google Sheet with some data and basic charts has evolved into something much bigger.

In 2025, the newsletter audience grew by 34%, while sponsorship revenue doubled. This level of growth was an absolute stretch goal for me this year, and I’m thrilled to have hit it.

This part of the Return on Security universe has no close substitutes and is not going anywhere.

This is the world that had more demand than supply in 2025. After a very successful pilot in 2024, demand for deep-dive writing exploded in 2025.

While AI-produced writing had exploded in volume in 2023 and 2024, the value of that writing has plummeted. As such, a need for more human-centered writing made a resurgence.

When done with the right approach, these deep dives can reveal the larger functions at play in our industry and society alike that we may often miss. It also gives me the opportunity to work with some great people behind the companies out in the industry, trying to solve problems.

Not every company warrants a deep dive, of course. Just like not every company warrants an angel investment. I plan to remain selective with these deep dives going forward, as the goal is not to maximize the number of posts, but to maximize the impact of each one.

You can see the current archives of deep dives here, and be on the lookout for a few more in 2026. If your company is solving a problem that the rest of the industry needs to understand, my door is open for 2026 collaborations.

While this world currently serves a small, focused group of customers, it has transitioned from a small experiment to a sustainable model.

Monthly revenue grew by nearly 400% this year, and this is becoming a proprietary source of truth, providing a consistent and necessary service. Rather than competing on low-quality data or volume, my focus has always been on the accuracy, uniqueness, and quality of the data itself.

Strategically, it makes sense to ramp up this business, as it leverages the research I’m already doing for the newsletter each week.

Strategic compounding is the name of the game.

In 2026, I plan to continue compounding returns in the areas the business is already winning. A central theme is to maximize the leverage of work I’m already doing and remain open to business opportunities that emerge from that research.

I plan to run a few targeted experiments aimed at vertical integration and finding ways to apply the insights from Return on Security in more high-impact collaborations.

As always, the focus will remain on intentionality and prioritizing high-leverage activities that have the greatest long-term value for the time and capital invested.