Welcome to The Nightcrawler, a weekly collection of thought-provoking articles and analysis on technology, innovation, and long-term investing. The Nightcrawler is published every Friday evening by Eric Markowitz, Nightview Capital’s Director of Research. Follow him on X. 

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In this evening’s email… 

Quote of the week: “Knowing what you don’t know is more useful than being brilliant.” — Charlie Munger

The rebel who invented IBM’s first PC

I finally got a chance to read this long-form story about Don Estridge, a “cowboy-boot-wearing mid-level executive” at IBM who assembled a team of corporate misfits and led Big Blue into the personal computer revolution in the early 1980s.

Despite his success, Estridge’s tenure was marked by internal conflicts and limited recognition. Ultimately, it’s an insightful story about how the best leaders (many of whom never get the recognition they deserve) deliver results simply by creating a culture of meritocracy of ideas—and a fierce sense of loyalty among their team. 

• Key quote: “Estridge was hugely charismatic, although his personal magnetism was drawn from a different source than that of Steve Jobs at Apple or Adam Osborne at Osborne Computing. They were men who sold their own visions. They could create ‘a reality distortion field’ around themselves (a term coined by Apple’s Bud Tribble about Jobs). They could convince you of the value of their ideas and inspire you to give everything in their service. Estridge was the polar opposite. He listened and supported. His role was to set objectives and provide people with the resources or political cover they needed. This approach inspired a different kind of loyalty from those who worked for him, but it was just as fierce. And it delivered results.”

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How to escape “the black sheep paradox”

For my second column in Big Think Business, I wrote about an idea I think about often: In order to achieve success — be it as an investor, entrepreneur, writer, intellectual, artist, or really any creative field — one must resist the temptation to conform, often when it is the most painful to do so.

It’s a paradox because success is the result, typically, of some sort of contradiction: a willingness to underperform (or be ridiculed) in the short-term that will create the necessary platform on which to succeed in the long-term. In the column, I offer three ideas—effectively a practical mental framework—to circumvent the “herd mentality” mindset. The three ideas are: deep learning, diverse learning, and writing. I continue: 

• Key quote: “Throughout history, some of the most successful individuals, companies, and technologies began as black sheep. They were outsiders who were either dismissed (or detested) by the mainstream, only to achieve extraordinary success years later. For instance, shortly after Alexander Graham Bell introduced the telephone in 1875, Sir William Preece, chief engineer of the British Post Office, remarked: ‘The Americans have need of the telephone, but we do not. We have plenty of messenger boys.’ So what makes a black sheep? I don’t think there’s any singular trait, but I do think there’s an element of biochemistry — or even neurodiversity — to it. This is something we’ve all probably witnessed to some degree or another in our lives: some people are simply born with an ability to ignore what others might think of their actions and behavior, which can create leverage to pursue ideas that others might not dare touch.”

A few more links I enjoyed: 

Crashes and Competition – via Stratechery

• Key quote: “In any massive failure there are a host of smaller errors that compound; in this case, CrowdStrike created a faulty file, failed to test it properly, and deployed it to its entire customer base in one shot, instead of rolling it out in batches. Doing something different at each one of these steps would have prevented the widespread failures that are still roiling the world (and will for some time to come, given that the fix requires individual action on every affected computer, since the computer can’t stay running long enough to run a remotely delivered fix). The real issue, though, is more fundamental: erroneous configuration files in userspace crash a program, but they don’t crash the computer; CrowdStrike, though, doesn’t run in userspace: it runs in kernel space, which means its bugs crash the entire computer — 8 million of them, according to Microsoft. Apple and Linux were not impacted, for a very obvious reason: both have long since locked out 3rd-party software from kernel space.”

The hard thing about hindsight: Why looking back has its limits: Q&A with Ben Horowitz – via Mike Hodgkinson / Big Think

• Key quote: “It’s very easy to read a business case study to figure out how a decision should have been made. Unfortunately, it’s a somewhat useless exercise in the real world when you have to make business decisions with maybe 5% of the total information that you’d like to have, and you rarely have time to get more information before the decision comes due. In hindsight, you have perfect information, so that doesn’t really inform the process.”

From Failure to Success: The Hidden Stages of Change with Dr. Meghaan Lurtz and Ted Merz – via Matt Ziegler / Cultish Creative

• Key quote: “Our conversation weaved through personal anecdotes, from dental hygiene habits to life-changing decisions, illustrating the complex interplay between emotions, behavior, and storytelling in the process of change. We discussed the impact of data and technology on our self-perceptions and the stories we tell ourselves. I was particularly struck by how our guests’ different perspectives – Ted’s intuitive, story-driven approach and Meg’s analytical, research-based view – complemented each other, offering a rich, multifaceted exploration of how humans adapt and evolve. This episode truly highlighted the universal nature of change and the power of understanding its processes in our personal and professional lives.”

The problem with problem-solving is slowly destroying the world – via Matt Joass / Whole Brain Investing

• Key quote: “For those that love investing, shifting to a whole brain approach is also the best way to identify the extreme outlier performers that I call Monsters. The small group of companies that generate insane, life-changing returns for shareholders. As Tom Morgan presented at Sohn so brilliantly, this mindset shift is the difference between analyst and PM, and between satisfactory and legendary. In future articles we’ll be digging into the practical and applied steps to implement a Whole Brain approach to understanding business and investing.”

From the archives:

Confessions of a Crazy Stockpicker – via Arne Alsin

• Key quote: “My weapon is my biochemical computer and the quality of its decision-making process; brain science shows performance is highly variable. Elimination of distractions, rituals, there’s all kinds of things you can do to think better. I’ve found if I consciously slow down the research process, I get the best results. Really dive deep into one thing at a time, to the exclusion of all else. Make it personal, get obsessed sort of thing. To work diligently and slow takes a lot of time, of course, and I’ve developed lots of silly time-savers. Same sandwich for lunch everyday, you’d be surprised how much time that saves, no more where to go, what to eat. No football watching or playing golf for last two years. (Of course, I hope my opponent enjoys such things, and to the fullest extent.) Ambidextrous shaving in the morning, what of it? You’ve got two hands. Two cheeks. For the cost of an extra shaver you get the job done in half the time. Good for hand-eye coordination too. Saves 14 hours per year.”