I had a debate with an entrepreneur this past weekend about AI and software companies. The question was whether AI will disrupt mission-critical software companies. Think ERP, CRM, and HCM software like NetSuite, HubSpot, Salesforce, Workday, etc.

Having built an ERP system with CRM functionality, my answer is no. In the short to medium term, these software companies will continue to have a strong moat. I believe this for two reasons. First, these systems are very complex and run functions that are mission critical. The risk of replacing one of them with a system that doesn’t work as well is too high, even if the upside is saving money. Disrupted operations can lead to significant financial losses and tarnish a company’s brand. Most companies don’t want to take those kinds of risks (start-ups might, though).

When I was running my company, there was zero chance you could get me to change from the ERP/CRM system we built for ourselves. The risk and learning curve associated with switching were too high. Even if someone had given me the software for free, I would have said “no thanks.”

Cost is the second reason I believe mission-critical companies aren’t about to be disrupted by AI. Having AI build a system as complex as the ones mentioned above would take significant time and energy and cost a ton via tokens. Then there’s maintenance. You can’t just build it and forget about it; you have to maintain homegrown systems, which can require material resources. When a company thinks about the time, energy, and cost required to build and replace a system, they’ll keep what they have and allocate those resources to high-return activities.

My company’s internal software was a living thing. We were always making improvements and changes to it. I learned over the years to budget a certain amount of salary and team bandwidth for maintenance of this software.

Complex, mission-critical software is the backbone of many companies. If one of these systems stops working, a company is flying blind and in some cases can’t operate at all.

As of today, I don’t think these companies are at risk of losing customers. Whether they’ll continue to grow at historical rates is a legitimate question. I think the probability that they will is high, because I doubt that company leaders want to start building these types of systems from scratch. The return on the allocation of resources doesn’t make sense.

Current Project: Reading books about entrepreneurs and investors and sharing what I learned from them

Mission: Create a library of wisdom from notable entrepreneurs that current entrepreneurs can leverage to increase their chances of success

Cumulative metrics (since 4/1/24):

• Total books read: 122
• Total blog posts published: 819

This week’s metrics:

• Books read: 1
• Blog posts published: 7

What I completed in the week ending 7/5/26 (link to the previous week’s commitments):

• Read Market Wizards: The Next Generation by Jack Schwager and George Coyle, a biographical anthology profiling nine people who generated outsized returns in public markets. This book is interesting because the nine people accomplished this at very young ages. The book does a good job of detailing their backgrounds, their origin stories, and how they approach decision-making in highly uncertain situations when the stakes are extremely high.

What I’ll do next week:

• Read a biography, autobiography, or framework book

Asks:

• No ask this week

Week three hundred twenty-seven was another week of learning. Looking forward to next week!

This week, I consumed less content than usual because it’s a holiday week. None of it is worth sharing. Next week I’ll get back to my normal content consumption level. I hope to find a few nuggets worth sharing.

Happy July 4th!

I hope everyone had a great holiday!

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I like to relax and enjoy holidays, but over the last year or two, I’ve established a habit of setting a challenge for myself for each holiday. I missed doing so for Memorial Day, and I want to get back on track for the 4th. The challenges are fun ways to push myself or make progress on a current project. I try to complete the challenge, and usually I do, but sometimes I overestimate what I can do during a holiday. Regardless, it’s fun, I learn something from the process, and I feel like I made progress on something I’m interested in.

Over the last few months, I’ve collected several research reports and articles written by notable people that I want to read. I never get around to reading them, though. They pile up in my office.

My goal for this holiday is to read two of these reports by Tuesday.

That’s it; that’s the challenge. Very simple. Wish me luck.

The book I’m reading this week is great. It’s a biographical anthology about nine people who achieved outsized success. I won’t spoil it (check the post on Monday for the title), but one of the authors said something that’s stuck with me. After reading tons of books in his field and interviewing the nine people in the book, he realized something:

[T]here is almost always someone achieving enormous success in doing something that you think is impossible.

I agree. If most people think something is impossible, it may be more the case that it’s really hard and tons of people have failed at it. If you’re one of the diligent people who figure it out, the reward could be massive. This is a classic power-law outcome. Only a small fraction of people succeed, but the ones who do receive rewards so large they’re hard to comprehend. Think Steph Curry’s salary of $62 million for the next NBA season (per spotrac) or Jeff Bezos’s $256 billion net worth (per Bloomberg as of this writing).

Hard things are . . . well . . . hard. That doesn’t make them impossible. Many hard things seem impossible but are actually quite possible if effort is applied to solving or mastering them over a long period of time. Bezos and Curry spent decades working at and perfecting their crafts. In the early years, they weren’t sure they’d succeed, but they knew their chances of success would continue to go up as they worked at it consistently. Each has achieved what, 20 years ago, many would have said is impossible. In reality, it wasn’t impossible; it was just really hard and required a ton of energy and commitment over a long period of time to make it happen.

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Today is the last day of June. That means Q2 is officially over and we’re halfway through the year. The first half of 2026 went by fast, but for whatever reason, I don’t feel like I made the most of it. I want to make the most of the year as a whole, so I’ll be experimenting with some changes and new habits. Here’s hoping they work!