This past week, I watched a video in which the creator of Claude Code, Boris Cherny, explains what Claude Cowork is and walks through a hands-on demo of how to use it. Cowork is basically agentic AI that can do things on your behalf through your computer. The demo was helpful, and I decided to download Claude Cowork. It was easy to install.

Before I started playing with it, I wrote down one problem that I wanted Cowork to help me with (I’m trying to be mindful of Kindlin’s law). I did this because using a tool to help me solve a specific problem I’m excited about helps me better understand the tool (and its limitations). Otherwise, I poke around and get only a surface-level understanding of its capabilities, which I likely won’t retain.

I then started to work with Cowork to get connected via MCP to the data sources it needed to help me solve the problem. Connecting to Google Sheets API and Google Drive API took some troubleshooting, but Claude helped me figure out the issues quickly. Then I started putting the tool to work in Google Sheets.

I haven’t leveraged all of Cowork’s capabilities, but so far I’m impressed. Playing with it got my wheels turning about what’s possible. I feel like Cowork is something that nontechnical people can use to gain leverage and become more resourceful. I think it’s especially useful for entrepreneurs who are actively building because it’s like a quasi-employee you don’t have to pay and who never gets tired.

This tool is new, but I think becoming familiar with it is worth the effort because of the potential gains. Cowork feels like a potential force multiplier of my efforts that will increase my output and improve my outcomes.

‍

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: 103
• Total blog posts published: 686

This week’s metrics:

• Books read: 1
• Blog posts published: 7

What I completed in the week ending 2/22/26 (link to the previous week’s commitments):

• Read How to Decide, a framework and workbook from Annie Duke that details tools and a multistep process to improve your decision-making

What I’ll do next week:

• Read a biography, autobiography, or framework book

Asks:

• No ask this week

Week three hundred eight 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:

• No material struggles related to this project this week.

What I learned:

• No material learning related to this project this week.

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

Yesterday, I shared a post about technology and software company valuations (see here). It included my back-of-the-envelope process for valuing companies. Today, I had several conversations with friends who read that post and are similarly interested in some of the companies because their valuations are attractive. I hadn’t planned on that, but it was a nice, unexpected benefit of sharing my thinking publicly. My takeaway is that I should share more of my thinking and analysis publicly because doing so sparks interesting conversations with people who are thinking along the same lines.

This week, I looked deeper into publicly traded software and technology companies. Over the last two or three months, some of these names are down over 30%. I wanted to know if they’ve become cheap and could appeal to value-minded investors.

Now, a lower stock price doesn’t mean a company is being offered at a cheap price (see cheap vs. low here). The only way I can determine if something is cheap is by determining its value first and then comparing its value to the price at which it’s being offered. If its price is below its value, it’s likely cheap.

I picked a few names and did some quick, back-of-the-envelope math to value them. I looked only at software and technology companies that were increasing in three areas: revenues (or equivalent), cash provided by operating activities, and free cash flow. Said differently, they had to be increasing top line, generating more cash, and putting more cash in their bank account.

I determined how much net cash each company has on its balance sheet. Think cash, treasuries, etc., minus short- and long-term debt. For example, a company has $ 4 billion in cash equivalents but $1 billion in total debt. Its net cash position is $3 billion.

I then subtracted that net cash amount from the market capitalization (i.e., valuation) to determine the enterprise value of the company. For example, a company with a $10 billion market cap but $3 billion in net cash has an enterprise value of roughly $7 billion.

Next, I looked at the statement of cash flows to determine the trailing 12 months of cash provided by operating activities. Some people like free cash flow, but I like cash provided by operating activities because it’s a good estimate of how much cash the company generated from its core business and could hypothetically distribute to shareholders. Again, this isn’t the perfect figure to look at, but for quick, back-of-the-envelope math, it does the trick for me.

I then divide the enterprise value by the trailing 12 months of cash provided by operating activities to determine the operating cash flow yield. For example, a company with a $7 billion enterprise value that generated $700 million in cash from operating activities in the last year is generating a 10% annual operating cash yield on an investment made at a $7 billon enterprise value. In theory, over 10 years (assuming no growth, no taxes, etc.), the company would generate an additional $7 billion in cash. It could distribute that $7 billion to shareholders, which means anyone who bought at a $7 billion enterprise value would have made their money back over those 10 years. Alternatively, if no distributions were made to shareholders, there’d be an extra $7 billion in the company’s bank account, so net cash would increase by $7 billion (assuming they didn’t reinvest any of the cash). This is a simple example that ignores lots of potential nuance, but you get the gist.

The result of my analysis was eye-opening. Some of the software and technology names I examined (mid- and small-cap companies) were trading at very attractive yields considering that the current 10-year treasury is ~4% and historically it’s ~6% (see here). One mid-cap software name was trading at an almost 9% yield. It’s an application software company, so the threat of AI is a real unknown for them and the durability of their cash flows isn’t crystal clear right now. But that’s still an attractive yield for a company that’s currently growing at over 20% and whose growth rate likely won’t go down in the short-term to medium-term.

My gut feeling is that the baby might have been thrown out with the bathwater. Some software and technology names are currently offering attractive operating cash yields. There’s more risk than with something like a 10-year treasury, for sure, but I’d imagine that savvy, value-oriented investors are analyzing these companies and closely watching the ones with strong moats that AI can’t easily erode and whose cash flows seem durable and likely to continue increasing.

I can’t predict the future, but my rough math indicates that today, some (not all) public software and technology company valuations reflect reduced potential downside (risk) and increased potential upside (reward).

I’m curious to see how things in the stock market play out going forward.

Yesterday, I shared a post (see here) that includes my reading stats for 2025. After writing it, I realized that since I began my book-a-week reading habit in April 2024, I’ve read 100 books in roughly 100 weeks. For whatever reason, that hadn’t occurred to me before yesterday. It made me feel accomplished and motivated, and it feels like a material milestone that I want to keep extending. So now I’m more motivated than ever to read a book every week!

In 2024, I began reading a book every week. I wanted to share what I’d read, so I posted a recap of my 2024 reading stats and lessons learned (see here). I was frustrated by how hard it was to share a list of all the book titles (see here), so I created a page about each book I read in 2024 (see here). I wanted to replace the Google Sheet I use to track all my reading, so I created a searchable library of all the books I’ve read (see here). I update it weekly.

Last year, 2025, was year two of consistently reading a book every week, and I want to share a recap of my stats and lessons learned. Sorry it’s late (the goal was January).

High-level stat for 2025:

• Books read: 51

2025 breakdown by month:

• January: 4
• February: 4
• March: 4
• April: 4
• May: 4
• June: 5
• July: 4
• August: 5
• September: 4
• October: 4
• November: 5
• December: 4

If you’d like to know what those 51 books were, see my 2025 reading list here.

Here are a few things I learned along the way:

• Reading for general information is critical if I want to generate new ideas—and I do. A Technique for Producing Ideas reinforced this. I have to learn about ideas so I can borrow from them when I’m trying to come up with a new one myself.
• Rereading high-quality books is sometimes better than reading new books. I reread a few books last year, and that helped me a ton. I’m now trying to reread at least one book every month.
• Synoptical reading is key to leveraging books to solve hard problems or deeply understand something. See more here.
• Framework books are a good fit for my personality, and they’re helpful. They give you the framework or process to use when you’re trying to accomplish something. They don’t give you the answer, but they show you how to get to the right answer.
• I get the most out of books when I read with intention; that is, with a clearly defined purpose for reading that book. That purpose should be a problem I’m actively trying to solve or a topic I want to understand better. This year, I’ve started writing down the problem I need to solve or the topic I want to understand before I choose a book. That’s helped me do more synoptical reading and get more from my reading that I can quickly put to use.
• There are no hacks with reading. I have to not only read but also do the work to understand what I’m reading. The best way to do that (that I’ve found so far) is to synthesize a book and share what I learned with others. But I haven’t found a way to be consistent with that.
• Learning through reading doesn’t feel like a chore anymore. It’s something I enjoy doing in my downtime. The personal-growth aspect of it appeals to my curious nature, and I feel like I can sustain it for a long time.
• Application of knowledge is the key to getting better outcomes. A priority of mine in 2025 is to apply what I’ve learned from reading, specifically around decision-making with imperfect information and probabilistic thinking.

Those are my takeaways and reading stats for 2025!

I’m a huge fan of podcasts. Watching them is one of the main methods I use to learn. Whenever I’m trying to learn about a topic, I find the most knowledgeable and credible people (i.e., they’ve had outsize success) in that field and listen to them being interviewed on podcasts. Like many, I started off on Apple Podcasts, but over the last few years I’ve been consuming podcasts via YouTube. I don’t watch the videos, really; I just listen. But YouTube’s search and discovery algorithm makes it many times easier to find relevant podcasts. Combine that with the fact that most podcasts (even audio-only ones) can be found on YouTube, and it became hard to stick with Apple Podcasts.

Today, the battle for podcast dominance heated up a bit. Apple announced that its Podcasts app will start supporting video in addition to audio podcasts (see here). This likely isn’t enough to get me to switch back to Apple for podcasts, but it signals the importance of podcasts to Apple and how video is becoming a dominant part of the podcasting landscape.

I’m curious to see what other changes (if any) Apple makes to its Podcasts app. YouTube has shown how lucrative placing ads in videos can be, and I imagine Apple wants in on this revenue source—especially when you consider that they pretty much invented the podcast space.

‍

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: 102
• Total blog posts published: 679

This week’s metrics:

• Books read: 1
• Blog posts published: 7

What I completed in the week ending 2/15/26 (link to the previous week’s commitments):

• Reread Limping on Water, the memoir of Philip Beuth about his time building Capital Cities Broadcasting and ABC along with Tom Murphy

What I’ll do next week:

• Read a biography, autobiography, or framework book

Asks:

• No ask this week

Week three hundred seven 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:

• No material struggles related to this project this week.

What I learned:

• No material learning related to this project this week.

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