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!

‍

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.

‍

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!

This past weekend, I created a flowchart with swim lanes to dissect what went wrong in a critical situation at a friend’s company. The details are complex, but one thing stood out to me. The more parties that stand between you and what’s happening with your customer or your product, the harder it becomes to understand the issue and quickly resolve it.

I had a loose idea of what happened based on a long email chain, but it wasn’t crystal clear and I wasn’t familiar with all the nuances. Creating the diagram this weekend helped me a ton. I was able to get my head around the situation by visualizing who did what. That helped me identify the parties that likely caused the issue and where and when in this complicated process everything transpired.

I now have a good idea of what needs to happen to prevent a repeat of this problem in my friend’s company. This exercise took longer than I expected, but the output was worthwhile. It’s definitely something I’ll keep in my toolkit.

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: 121
• Total blog posts published: 812

This week’s metrics:

• Books read: 1
• Blog posts published: 7

What I completed in the week ending 6/28/26 (link to the previous week’s commitments):

• Reread The 22 Immutable Laws of Marketing by Al Ries and Jack Trout, a framework for thinking about marketing that describes 22 foundational marketing laws

What I’ll do next week:

• Read a biography, autobiography, or framework book

Asks:

• No ask this week

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

Continuing with my new protocol, here I’m going to share content I consumed and learned from. This week, I spent time doing general learning about a variety of topics.

What I consumed this week and what I learned from it:

• Focusing downside lets you play offense in down markets – YouTube interview with Seth Klarman, CEO of Baupost Group. Klarman joined Baupost at the age of 25 when it was being formed. He owned no equity, but seven years later, he was CEO and owned 40% of the firm. Klarman believes that focusing on risk and a bottom-up approach puts you in a position to be aggressive and play offense when others are panicking. In about three months, he raised roughly $4 billion as the great financial crisis hit, and his firm was a big buyer, deploying $100 million per day across various asset classes!
• The next generation of market wizards – YouTube interview with Jack D. Schwager, author of the Market Wizards series of books. I love learning about the strategies of people who’ve achieved outsized success, so I’ve enjoyed Schwager’s books because that’s what they’re about. He just released a new book, which I bought, that explains how some people, mostly working from their homes, generated astronomical sums over roughly a decade. For example, one person went from around $50,000 to over $500 million in about a dozen years working from home. Schwager won’t write about someone until he verifies their results through account statements and tax returns, which adds lots of credibility to his books. One of the interesting things I picked up on in this latest book was the power of compounding. Key to the success of these people is sticking with their winners long enough to enjoy compounding while cutting losers so the losses don’t impact their overall compounding. This is a common theme I’ve seen before that leads to power-law results for venture capital and other famous public market investors.
• She has to spend +$200k/month – YouTube interview with Anne Mahlum, an entrepreneur who sold her business to private equity. This interview was interesting because she’s transparent about her $100+ million net worth and how it’s invested. She has to remind herself to spend enough money some months, and in some months spends $400,000 without impacting her overall wealth at all. Her experiences with family members made sense. Gifting her husband a substantial amount of money before they got married to avoid fights about money was unconventional but has worked well for her.

That’s what I learned from what I consumed last week.