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:

• I had trouble getting started on synthesizing another book this week. I need to adjust my approach somehow.

What I learned:

• Distilling a book or book chapter down to the essence of its main idea should be the goal when I’m writing posts about books. If I can get it down to a maxim, even better. Maxims are easier to remember (including for me).
• Just as my reading must be done first thing in the morning, I’m realizing that the daily habit of working on a synthesis of a book must be done early, too. Once the day gets going, who knows what’ll get thrown at me? The likelihood that I’ll get to the difficult task of synthesizing drops drastically.

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

After reading Getting Things Done by David Allen again, I realized I don’t have a great “inbox” to capture all incoming information and thoughts. The inbox is a core piece of the GTD method. It’s the holding area where you place things until you have time to process and sort them properly. Sure, I have the inbox for my email, but I didn’t have a go-to inbox in a tool I used to manage my productivity.

I’ve been working on cleaning up my GTD system by creating a clean, short-term (to be completed within a year) project list and defining next actions for each project. That’s going pretty well and should be done shortly. But because I don’t have a solid inbox, my GTD system hasn’t been as effective as it could be.

So, this week, I created an inbox in Apple Notes, moved all unprocessed notes into it, and added all new notes to it. I must say, having a single place to drop all new thoughts and incoming information has been helpful. It’s taken some discipline to make sure I put everything there, but now that I have the hang of it, I feel more confident that everything important is being captured so I don’t have to try to remember everything.

Another thing I like about GTD is that processing and sorting are separate from capturing my thoughts and incoming information. I can quickly capture thoughts about an article, book, project, or podcast in a messy note and save the note in my inbox. When I process my inbox, I add more context to the note and save it in the appropriate folder or project so it’s where I need it when I need it.

I’m still early in the process of cleaning up my GTD system and creating new GTD habits, but I think this, along with Tiago Forte’s Building a Second Brain process, will boost my productivity in 2026.

This week, I had a conversation with a good friend about the power of community. He’s an entrepreneur in a traditional industry and is looking for ways to increase awareness of his brand and the products he sells. He’s got good marketing ideas that follow what others in his industry have done successfully.

I introduced the idea of building a community around his product: First, create an audience of people who love the product for a deeply personal reason (i.e., it helps them solve a problem they care deeply about). Then, hopefully, convert some percentage of that audience into a community of people who will engage with each other (with some guidelines and light moderation).

I like this idea because it leans into a key market concept: word of mouth is the best form of marketing. People in a community love talking to one another and will invite other like-minded people into the community. They share what they’re doing in the community and how the community has helped them. This all helps knowledge of the brand and product spread via word of mouth.

I also like the idea of community because it creates a moat, or competitive advantage. When you have a community of people who’ve bought into a brand or product, they don’t want to leave the tribe they’re a part of, so it’s less likely they’ll leave or switch brands or products. Community makes customers stickier and creates a moat that’s hard for competitors to replicate.

Lastly, I really like community because it’s a great way to keep a finger on the pulse of what your target customer thinks of your existing products, learn about ideas for new products, and spot early trends you can capitalize on. It’s a great feedback mechanism and a way to stay connected to customers in an organic way, which leads to product improvements and new products that keep your customers loyal.

All in all, I’m a fan of companies leaning into creating communities, especially when they’re in slow-moving or antiquated industries.

For the last few years, I’ve been using X (formerly Twitter) as a research tool and a news source. I’ve learned a ton from the platform and connected with some great people, but I rarely post anything. What I did years ago was set up an integration to X. Every time I create a new blog post, it creates a post on X with a link to the post on my blog. It’s basically the lazy way of posting on X.

The integration is easy, but not very effective. X doesn’t love it when you link out to external sites. So, this year, I want to change how I share my thoughts on X. I’m going to convert my blog posts into native X posts. Not sure what this looks like or how I’ll do it, but I want to turn it into a habit by the end of the year.

I’ve been reading one book a week consistently for 96 weeks. It’s been a solo activity . . . so far. I read alone, think about what I read alone, and share my thoughts in a blog post. It’s a pretty self-contained process.

A few weeks ago, I was invited to join a book club. I’ve heard of book clubs but never considered joining one. After thinking about it, I decided to give it a shot—mainly because I’m curious to see how a book club operates and how it’s valuable to its members.

I didn’t have a book club on my bingo card for 2026, but this seems like something fun to try, with limited downside and large potential upside. I’m looking forward to my first meeting next month.

A few weeks ago, I wrote about how one start-up lawyer is changing his business model because of AI’s impact (see here). A few people reached out to me after that post and shared their perspectives on the disruption of legal services and other industries by AI. This topic is clearly top-of-mind for more people than I realized.

Today I read a blog post (see here) from Fred Wilson, founder of the famed venture capital firm Union Square Ventures (USV). Wilson describes having always been uncomfortable with the legal costs that USV incurs to close financing rounds for new start-ups they invest in. His latest quote was $50k for a deal he was working on last month (and the start-up’s lawyers probably charge it something similar, so the total for both parties is about $100k).

Wilson decided to try something different. He loaded Google’s NotebookLM with all his firm’s historical closing docs and the start-up’s data room docs. He asked NotebookLM a bunch of questions, and it pinpointed one issue, which he resolved with the start-up and its lawyers.

The end result was that with two hours of Wilson’s time and no legal fees, he was able to get comfortable with the deal docs (and, I assume, close the deal or get it close ready). That’s a tremendous cost and time savings.

This is a very interesting use case of AI empowering law firm customers, specifically investment firms, to move faster and at lower cost. It confirms what the start-up lawyer I spoke with last month believes: AI is disrupting the legal industry by empowering lawyers’ clients, and law firms will be forced to adapt.  

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: 96
• Total blog posts published: 637

This week’s metrics:

• Books read: 1
• Blog posts published: 7

What I completed in the week ending 1/4/26 (link to the previous week’s commitments):

• Reread Getting Things Done, a framework for boosting productivity while reducing stress
• Synthesized The Little Book of Market Wizards

What I’ll do next week:

• Read a biography, autobiography, or framework book
• Write a post sharing what I learned from synthesizing The Little Book of Market Wizards
• Write a post sharing what I learned from synthesizing The Art of Execution

Asks:

• No ask this week

Week three hundred one 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:

• I’m still synthesizing the second book (The Little Book of Market Wizards) of my holiday challenge (see here). I thought I’d be done by now, but making this a daily habit hasn’t stuck yet. I want to find hacks that let me synthesize books more efficiently.

What I learned:

• I posted one synthesis of a book, and it resonated with people. I assume they appreciate getting the main points of the book in much less time than it would take to read it.
• When I synthesize a book, I create a digest in Google Docs and then write a post based on that doc. This week, I was trying to remember something from a book. Instead of grabbing the book, I used the digest and post to refresh my memory. Reviewing either or both is much more efficient than digging into the book itself. I’ll be doing more of this when I want to revisit material from books.

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

A close friend was telling me about how the company he works for completed its IPO in December. I realized I haven’t done an IPO update since Q2 (see here). I know that IPO activity picked up in 2025, but I wanted to know by exactly how much. So today I dug through data. Here are the updated IPO stats for calendar year 2025:

• 2025: 347

Here’s the breakdown by month:

• January: 28
• February: 28
• March: 19
• April: 32
• May: 33
• June: 26
• July: 37
• August: 28
• September: 32
• October: 35
• November: 18
• December: 31

For comparison, here are previous years’ IPO stats:

• 2024: 225
• 2023: 154
• 2022: 181
• 2021: 1035
• 2020: 480
• 2019: 232
• 2018: 255
• 2017: 217
• 2016: 133
• 2015: 206

IPO activity picked up significantly last year. In 2025, IPOs increased by 54% year over year. And increased by 125% from the 2023 post-COVID, post-ZIRP low. Another interesting fact is that if you exclude the COVID years of 2020 and 2021, when interest rates dropped rapidly, and look at more normal years, 2025 was the most active year for IPOs in the last decade.

I imagine that technology CEOs and their PE or VC investors are watching these IPO stats and thinking about taking their companies public in 2026, given public market investors’ appetite for buying shares in tech companies.

I’m curious to see how Q1 IPO activity looks and if 2025’s trend continues.

If you want to see the IPO stats—recent or historical—try here (where I get my IPO data).

I use AI daily, and for most of 2025, I used ChatGPT as my main AI tool. This week, a friend asked me if I wanted some candid feedback. A look in the mirror, so to speak, with the reflection generated by AI’s understanding of me. I love getting candid, raw feedback, so I said yes.

They told me to run this prompt in ChatGPT: “Be blunt and honest with me and tell me what I need to change for 2026.”

Using the 5.2 model, I did. Even though ChatGPT doesn’t have full context about me because I don’t run everything I’m thinking or doing through the platform, it still gave me a thorough, thought-provoking response. It got me thinking, which I enjoyed.

If you’re a ChatGPT user and you’re curious about what it thinks you should change about yourself, run this prompt. It’s fun!