Yesterday, I shared that Alphabet (Google’s parent company) was planning to issue some 100-year bonds. According to a Bloomberg article (see here), they were planning to raise around $20 billion. But they ended up raising almost $32 billion in debt in less than 24 hours. It looks like they sold $20 billion in debt Monday. And then raised another almost $12 billion in pounds sterling and Swiss francs. I don’t know why they’d raise in those denominations, and I’m curious to learn more about bonds and why they chose this strategy in particular.

I’m eager to learn more about the world of bonds, and this seems like the perfect time.

In November, I read a book that’s stuck with me. Dangerous Dreamers was a historical recounting of the events that set the stage for the junk-bond and LBO explosion in the 1980s. I was intrigued by how an obscure book and an insight that fast-growing companies couldn’t borrow money in the bond markets at the time sparked Michael Milken’s idea to create (and control) the market for high-yield—junk—bonds.

Ever since then, I’ve been interested in learning more about bonds of publicly traded companies (and governments) and the public market for them. I’ve bought several books and started tracking down people who work in these markets to talk with. Lots to learn, but I think it’ll be a fun multiyear project. I suspect it will complement what I’ve learned from analyzing and investing in public stocks.

Today I read an article (see here) that made me want to begin this project sooner rather than later. It was reported that Alphabet (Google’s parent company) is thinking about issuing a 100-year bond. From what I can gather, a bond with a 100-year duration is very rare and hasn’t been issued by a technology company since 1997 or so.

Reading that article highlighted that I don’t know what I don’t know about the bond market, and it made me more curious and more eager to fill my knowledge gaps. Hopefully I’ll be able to carve out time soon to start reading my new bond books.

Current Project: Reading books about entrepreneurs 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: 101
• Total blog posts published: 672

This week’s metrics:

• Books read: 1
• Blog posts published: 7

What I completed in the week ending 2/8/26 (link to the previous week’s commitments):

• Reread A Man for All Markets, the autobiography of mathematician, card-counting pioneer, author, and hedge fund manager Ed Thorp

What I’ll do next week:

• Read a biography, autobiography, or framework book

Asks:

• No ask this week

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

Current Project: Reading books about entrepreneurs 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

What I struggled with:

• Same as the last few weeks: I had trouble getting started on synthesizing another book. I’ve scratched this for now. I need to come up with a better approach.

What I learned:

• This is more an acknowledgment of the obvious than something I learned. My approach to synthesizing a book I’d read and writing a blog post about it weekly didn’t work. Well, it worked only during a holiday (Thanksgiving). It doesn’t work during a normal week, and I need to figure out another way.
• Video software (e.g., Zoom) removes geographical barriers and drastically expands the potential size of book clubs. I attended a book club meeting with more than 250 attendees (I was amazed). It taught me a lot about the potential of virtual book clubs (see more here).

That’s what I learned and struggled with last week.

This week I caught up with a friend, an entrepreneur who sold his company and has advised founders for over a decade. He pointed out something that differentiates entrepreneurs from others. Entrepreneurs get excited by the potential of an idea and how big the end result could be. That’s enough to get them started. They’re totally focused on the end and the one next thing they can do to move forward. That’s it. That’s all they need to press go.

When they talk with non-entrepreneurs, they can become frustrated because many non-entrepreneurs focus on something different. Non-entrepreneurs can’t wrap their head around the end result because the path to it is unclear or has imperfections. They want to labor over details, achieve clarity, and resolve imperfections before they even think about starting down the path or think about how big the idea could be. The entrepreneurs feel like they’re being dragged into the details and asked questions they can’t answer and that don’t matter yet. They want to talk about the big, high-level opportunity, but they’re being beaten up over the small details of the plan. It’s annoying.

I agree with my friend. I’ve been in this situation many times. Someone asks me detailed questions about something I want to do, and I get frustrated because I don’t think the things they’re asking me matter yet. They’ll be figured out in due course.

A lot of the disconnect is in how entrepreneurs approach getting things done. They’re problem solvers by nature and often must do things they haven’t done before. The way they do that is by focusing on their next action, not all the actions or steps they’ll need to take. They know that with every step they take, they’ll learn something (good or bad) that will help them figure out what the next step should be. Then they’ll act again. This continual process of acting, learning, and acting is essentially an iterative approach to reaching the result they want without starting with a clear path or plan.

When entrepreneurs are asked to provide a detailed plan or path, they become frustrated because they know it isn’t necessary. Things aren’t likely to go as planned, even if there is a plan. Solutions to problems will reveal themselves along the way. The best way to reach a big goal is to get started on it and figure things out along the way.

I’m still curious about the United States from 1968 to 1982. It was a crazy period that saw inflation peak of about 12%, the federal funds rate reaching almost 20%, and the stock market performing poorly. One thing I want to understand more deeply is the reasons underlying the stock market’s performance. Increasing interest rates push down company multiples and valuations, so that makes sense to me. But I think there’s more to know.

I was listening to a podcast when the guest mentioned that Warren Buffett wrote an article in Fortune magazine in May 1977 that explained how inflation robs equity investors. They spoke very highly of the article and explained part of it, which piqued my interest. So, I’m going to find that article and give it a read. Hopefully, I’ll grasp what Buffett was saying and can share my understanding.

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I’ve been thinking about new projects, ideas, and things to work on. I looked at what I’ve done in the past and sought themes or patterns. I think there are three high-level buckets that capture everything I’ve done (and want to do going forward):

• Building – Creating new things. It could be starting new companies or just doing fun personal projects. I like building things that interest me. Even if they’re not commercially viable (or successful), I enjoy the process because I learn a ton along the way. This category includes helping or supporting entrepreneurs who have a vision for what they want to build.
• Investing – Investing, for me so far, means investing in other companies—most enjoyably, early-stage start-ups and publicly traded companies. The process of digging into a company, its market, and the people running it is fun, and I always learn a lot from that analysis. Change is constant, so there’s always something to learn (you never master it), which I love too.
• Learning in public – Sharing online what I’ve learned (or what I’m trying to learn) has accelerated my learning, expanded my curiosity, and, hopefully, helped others along the way. Many times, I thought I understood something until I sat down to write a post or record an audio pod about it. The act of explaining something to other people exposes gaps in my understanding and crystallizes my thinking. Learning in public has also been a great way to stimulate my mind and exercise my brain.

Building companies, investing in companies, and learning about people who build or invest in companies. The common thread is entrepreneurship. That’s it. Those are my interests in a nutshell. If something falls into one of those buckets, I’ll likely be interested in it.

This week I had the opportunity to participate in my first book club. For context, this book club was virtual and academically oriented. A few initial thoughts:

• Over 250 people attended, which shocked me. I didn’t have any expectations, but I hadn’t considered that such a crowd would take part.
• The virtual nature of this club allows it to cast a wide net. There were people from other countries, including Canada. The internet removes boundaries—this group could find people anywhere.
• The author of the book was part of the session and shared his thoughts, which I enjoyed. It’s always nice to hear authors’ deeper thoughts.
• This meeting was styled as something of a debate. It began with people arguing for and against the argument in the book. The author then responded to points against the book.
• Many of the arguments presented were prepared statements.

Overall, I enjoyed my first book club experience. The scale and reach of this club were much greater than I could ever have imagined. That definitely stuck with me and has me thinking much bigger about the possibilities of book clubs.

Recently, I caught up with the founder of a high-growth company. The company exploded in growth over the last few years, and now they’re planning for the next twelve months. The founder mentioned that one of his focus areas is maturing the organization. He wants to add more process and structure so they can continue to scale rapidly without the wheels falling off.

When growth is crazy, you normally see a lot of hiring. Things are happening so fast that no one has time to delve into problems or the things holding them back, so they throw bodies at them and hope the smart people they hire will figure it out. The result is continued growth but a lack of process and structure.

When the leaders start planning for continued growth over the next few years, they realize they can’t get there by doing what they’ve been doing. They want more visibility into what’s happening operationally below them, more operational consistency, and assurance that their operations can scale as the company continues to grow.

It’s a cycle I’ve seen before: growth, efficiency, and then more growth. I like to think of it as the company catching up to the expectations implied by its revenue growth. For high-growth companies, it’s part of their normal cycle.

Current Project: Reading books about entrepreneurs 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: 100
• Total blog posts published: 665

This week’s metrics:

• Books read: 1
• Blog posts published: 7

What I completed in the week ending 1/25/26 (link to the previous week’s commitments):

• Read Take the Measure of the Man, the memoir of Comcast Corporation cofounder Daniel Aaron  

What I’ll do next week:

• Read a biography, autobiography, or framework book

Asks:

• No ask this week

Week three hundred five was another week of learning. Looking forward to next week!