On January 27, 2020, I had lunch with an entrepreneur friend. He encouraged me to share what I’d learned from scaling my bootstrapped company to over $10 million in annual revenue. I’m private and was reluctant, but I wanted to help others who were just like me when I started my company—people who didn’t know what they didn’t know. I agreed, and we began a 60-day challenge. We both posted content daily to help other entrepreneurs (see our challenge details here). That challenge began on March 9, 2020, and ended on May 10, 2020. I didn’t miss a day—and I learned to enjoy the habit of reflecting and writing every day.

That was five years ago. Since then, I’ve written and shared a post every single day. That’s over 1,825 consecutive days of sharing my thoughts. When I agreed to the challenge, I had no idea I’d still be posting five years later, but I’m glad I am.

Every March, I reflect on my writing journey. Here are a few reflections:

• Strike zone – I read a book a week, mostly biographies. I used to think of reading and writing as independent hobbies. But writing about the books I’m reading has enhanced my learning and thinking. Combining them feels like it’s put me in my strike zone.  
• Format – I’ve played with a few different formats for creating posts about biographies I’ve read. The format I like best is a deep-dive series about a biography (see examples here and here). I’m aiming to get back to that format, and I’m building software to help with the creation process.
• Luck – Bringing value to others by writing has increased my luck surface area and led to magnetic luck (more on luck types here). When I focused more on writing about biographies, it led to more magnetic luck. Entrepreneurs want to know what other entrepreneurs have figured out but don’t always want to read an entire book.
• Audio – Last year, I tested doing a solo podcast about the books I was reading. It was really an audio version of this blog. I did 100 episodes to get reps and learn. Audio is a powerful format but requires significantly more work than writing. Publishing a podcast episode daily wasn’t sustainable. I’ll revisit doing a podcast, but I’ll need more support next time, and I’ll test different formats.
• Level up – I want to take this blog to the next level and create more value for others. Adding a page detailing all the books I’ve read and creating a profile page for each book (see here) is an experiment and just the beginning.
• Annual contract – Every March, I’ve asked myself if I’m enjoying this and want to keep doing it. If yes, I re-up for another one-year contract with the option to renew. I’ve now signed through 2026.

Those are my reflections. I’m looking forward to the next year. I feel like year six will be epic!

This summer, I set a goal of creating 100 podcasts about books I was reading. It forced me to start tracking my reading in a spreadsheet. It’s nerdy, but it was necessary because every week, I read a book, wrote a blog post series, and created a podcast series about each book. The spreadsheet helped me keep everything organized. I paused the latter two after the summer because they were too inefficient and time-consuming, but I kept updating the spreadsheet and reading a book a week.

I looked at the spreadsheet as I was reflecting on the books I read in 2024. I figured I’d share some stats and learnings.

High-level stat for 2024:

• Books read: 52

2024 breakdown by month:

• January: 0 (I did read, but I can’t remember what books)
• February: 2
• March: 6
• April: 6
• May: 7
• June: 5
• July: 4
• August: 5
• September: 4
• October: 3
• November: 5
• December: 5

Here are a few things I learned along the way:

• Reading two books a week was too aggressive. I tried it in the March–May period, but I wasn’t absorbing as much of what I was reading or making as many connections. I was focused on finishing the books, which isn’t why I read. The pace was too fast, so I reduced it to a book a week, which feels more sustainable.
• Sharing what I learned from my reading was the big unlock. It took my learning and thinking to another level. Writing a blog post series and recording a podcast series forced me to identify insights and organize and communicate my thinking. The key tool in that process was creating a digest of each book, which was an extraction of the information I found important in each chapter, along with my insights.
• E-readers, such as Kindles, are great devices, but I prefer reading physical books. I highlight and add notes about insightful sections and ideas in the books. Those highlights and notes are trapped in each book, so finding and using them later is difficult. See here for more. As I’ve read more, this has become a painful problem. Trying to find something sometimes means reviewing several books’ notes and highlights. Experiencing this pain led me to several feature ideas for the “book library.”
• Reading a book is simple—but learning from what I read is more involved. It’s inefficient and involves lots of steps. The process of sharing what I learn from my reading is complex. It’s hard and has many steps and lots of moving pieces. This realization led me to add several more feature ideas to the “book library.”
• The value in reading lots of entrepreneurial biographies is that you’re exposed to the best ideas and experiences of entrepreneurs, and you can pull from them when you’re faced with a problem. The challenge is that this requires a great memory or knowing exactly where to look to quickly find something you’ve read. I don’t have a photographic memory, and I don’t always remember where I read something. I want to make it easy to find what I’ve read, which will be a big part of the “book library” MVP.
• My best ideas in 2024 came from piecing ideas together from various books. Making those connections was a great way to build upon what other entrepreneurs figured out. Solving a problem by building upon the knowledge of others rather than starting from scratch led to my having better ideas. I’m not an idea guy, so this was perfect for me, and I want to do more of it going forward. I don’t think this has to be completely manual and inefficient. Figuring out how to solve this and incorporate it into the “book library” is challenging, but I think it can be done, and I’m excited to figure this out because it’ll be a huge unlock for myself and others.

Those are my takeaways and reading stats for 2024!

2/26/25 Update: I finally published a list of all 52 books. You can see the list here.

2/27/25 Update: I created a searchable list of all the books I’ve read, and I’ll be updating it weekly. See here.

Data is telling me to write more long-form posts.

I looked at the data around my blog posts in Google Analytics. My most-visited pages are longer posts about biographies I’ve read. This post about Ted Turner’s wealth is my most-viewed post over the last six months and ranks on the first page of Google (search “Ted Turner net worth”). It’s part of a series I wrote on Ted’s autobiography.

People like these longer posts about entrepreneurs and books more than my shorter posts. I suspect the segment who read these longer posts in their entirety is small, but they’re also more likely to share a post (one was shared on Reddit).

The dilemma is that I write posts every day, and sometimes I need to write a short post about something that’s been on my mind. I’m worried that if I commit to writing only these longer posts, I’ll lose the ability to write short posts that help me crystallize ideas or problems. Writing has become a valuable tool to help me think clearly and I want the flexibility to write about whatever.

I noticed that some people who share their thoughts online separate their writings. The shorter ones are considered blog posts; each can be read in a minute or two. But the longer posts, called “essays,” require much more time to consume and are in a separate section of their website.

I started linking related posts at the bottom of each page, and I think that’s helped readers quickly find all posts in the same series. But it’s still pretty hard to find them among my 1,850+ posts, most of which are short. Discovering a long post if you’re already on my blog isn’t a great experience and needs to be improved.

I’m not sure if I’ll do this, but I do like the idea of making it easier for people to see all the longer posts in one section. I’ll think about this more. If you have feedback or suggestions, I’d love to hear them.

I learned the growth hack The New York Times used to explode readership.

Last week I read An Honorable Titan, a biography about Adolph Ochs, who acquired The New York Times and turned the paper into an institution. Adolph executed this strategy in around 1900, but I think it’s ingenious and something others could find helpful. So, what’d he do exactly?

The Times’s daily circulation was stuck at 26,000, and it was losing money. The Times made money from sales at newsstands and advertising revenue. Adolph determined that he needed to double his circulation to 50,000 to break even.

His paper was respected and sold for the going rate of $0.03. Papers that sold for less than that were deemed sensationalized and from the yellow press. These lower-quality papers sold for $0.01. At the time, the thinking was that anyone who wanted to read a respectable paper would have $0.03. The $0.01 and $0.03 tiers were accepted pricing norms.

This pricing logic didn’t make sense to Adolph, and he decided to blow it up. He hypothesized that “the requisite number of readers could be found among those to whom the difference between three dollars a year and ten dollars a year for a newspaper was a material difference.” Using this logic, he priced the Times at $0.01. The move shocked everyone. His advisers and other publishers thought he was crazy because he essentially reduced his revenue from newsstand sales by 66%. Said differently, he had been losing money before, and he would lose money faster—and be wiped out—if he were wrong.

A funny thing happened. Circulation skyrocketed from 26,000 to 75,000. This jump allowed him to increase advertising rates because more people saw the ads. The Times went from losing money to being solidly profitable. The newspaper world called Adolph’s move a stroke of genius.

What did Adolph see that others had missed?

The unsaid and accepted logic behind pricing at that time was that the poor were unintelligent and, therefore, had no desire to read a respectable paper. Adolph recognized that intelligence is evenly distributed through the population at all economic levels. Doing the math, he realized that the rich are a small percentage of the population and if intelligence is evenly distributed, there was huge unmet demand among the largest segment of the population, the poor.

If, say, 10% of people are intelligent and 100 people are rich, 10 would desire a respectable paper like the Times. If 1,000 people are poor, 100 would want the paper if it was affordable.

Adolph didn’t just accept the status quo. He did his own thinking to reach his own conclusions instead of accepting the thinking of others. This approach allowed him to see an opportunity everyone stared at but couldn’t see.

Today, I bought a book on impulse.

I was listening to an interview of an entrepreneur I’m researching. When asked about things that shaped his career, he mentioned a book and how it shaped his thinking—and I immediately bought it. I didn’t look at reviews. I didn’t look at the price. My purchase decision was already made.

I reflected on the purchase later. It wasn’t a biography or framework book. It was a historical book containing the author’s opinion about how past events contributed to boom-and-bust cycles. I wouldn’t normally be excited to buy a book like this, but I was excited about this one. But why?

Simple. It was recommended by someone I deem credible. And that recommendation carried more weight than other factors.

I know that recommendations are how most people buy books. But I hadn’t thought much about it in the context of my book project. I’m thinking about it now, and I think a lot of value can be added to other entrepreneurs if you can show them in a simple way which books credible entrepreneurs found helpful (in addition to all the other cool stuff I want to show them). The information is out there; it’s just not organized in a way that’s easy to use.

Social proof is a proven psychological phenomenon, and deploying it could be a great way to enhance discovery of books by entrepreneurs who’d find them helpful.

I need to think about this more, but those are my preliminary ideas.

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: 56
• Total blog posts published: 357

This week’s metrics:

• Books read: 1
• Blog posts published: 7

What I completed this week (link to last week’s commitments):

• Read An Honorable Titan, a biography of entrepreneur and publisher Adolph Ochs, who bought The New York Times
• Caught up (mostly) and rekindled conversations with prospective developers

What I’ll do next week:

• Read a biography, autobiography, or framework book
• Reach out to two more developers about this project
• Explore using Gumloop, Lindi, and Manus to see if they can help with this project
• Adjust layouts for a list of entrepreneurs on my blog
• Crystallize and write down idea for a biography-related website

Asks:

• If you can get me an invitation code to Manus, please let me know!
• If you know any full-stack developers interested in working on the software for my current project, please introduce us!

Week two hundred sixty-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:

• No material struggles this week related to this project. Just playing catch-up after being out for a few weeks.

What I learned:

• I’ve been seeing “vibe coding” references lately. A friend explained it to me as “using natural language to create actual code by prompting to focus on features and capabilities but not line-by-line code. It’s different from no code, which is building blocks. Vibe coding is what people are doing in cursor. They prompt something that writes an entire application for them.” This definition was useful to me.
• This same friend shared with me a free DeepLearning.AI course about vibe coding taught by Replit. I signed up for it. Enroll here.
• I had more conversations this week with developers, but when I was asked about the details of the technical stack, I could answer only some of the questions. My gut tells me this signaled negatively to one senior developer I chatted with this week. My developer friend is available and will help transition things, but I need to understand the stack better and be able to communicate how it all works together.
• I looked at data about the posts I’ve written about biographies. The long-form posts about part of an entrepreneur’s journey get more visits than the shorter posts about one takeaway. A few shorter posts have done well, but they’re the exception. I suspect that the longer posts are also shared more.
• I learned about Manus and Gumloop. Manus is an AI agent tool, and Gumloop is an AI workflow tool. They may be able to help me with certain aspects of this project. I plan to experiment with both.

Those are my struggles and learnings from the week.

This week there was lots of discussion in financial media around the CoreWeave IPO. CoreWeave provides cloud-based GPUs to AI developers. The IPO was completed today after the number of shares being sold in the IPO was reduced from 49 million to 37.5 million and the share price was lowered to $40 from the planned $47 to $55. (see here)I haven’t kept close tabs on the IPO market since my last update in October 2024 (see here), so I took a look today. Here are the updated IPO stats through March 28, 2025:

• 2025: 73

For comparison, here are prior years’ IPO stats:

• 2024: 225
• 2023: 154
• 2022: 181
• 2021: 1,035
• 2020: 480
• 2019: 232

IPO activity picked up in 2024. We were pretty much back to the 2019 level. COVID and ZIRP contributed to the 2021 IPO explosion (see here). When interest rates began rising sharply in 2022, we saw an implosion of IPO activity in 2022 and 2023.

Time will tell how receptive the market is to CoreWeave. It took almost a year before public-market investors were interested in buying technology companies that IPOed in 2023 and 2024, such as Reddit, Instacart, and Klaviyo.

CoreWeave has seen explosive growth in the last year or so because of soaring AI demand (OpenAI is one of its biggest customers). I’m sure venture capitalists and technology entrepreneurs are watching to see how receptive public-market investors are to buying the company’s shares.

I’m curious to see how CoreWeave performs and whether we’ll see more technology companies going public via IPOs in 2025.

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

Two weeks ago, I read a second biography about Albert Lasker, The Man Who Sold America. It mentioned how Lasker worked with Adolph Ochs, who owned The New York Times, to free Leo Frank, who had been charged with the murder of Mary Phagan in Atlanta in 1913. Lasker and Ochs, both Jewish, felt Frank was being wrongly accused because he was Jewish. Learning how Lasker and Ochs created a sophisticated media campaign to draw attention to this case nationally was fascinating.

I’d never heard of Ochs, but I was curious about his journey and how he became the owner of The New York Times. This week, I began reading a biography about him, An Honorable Titan, by Gerald Johnson.

I’m early in the book, but I’ve already been surprised by Ochs’s history: The publisher of a nationally recognized and New York–based newspaper dropped out of school at 14. He wasn’t from an elite family or background. He had to start working full-time at 14.

Adolph began his career as an information entrepreneur in Chattanooga, Tennessee, where he sold a directory at age 19. In 1878, he and a partner created a directory of all the businesses in Chattanooga. This was a manual effort requiring them to canvass the entire city house-by-house to collect the information before they compiled it in a book.

The benefit of this grunt work was that Adolph developed a detailed understanding of the town, its businesses, and the entrepreneurs who owned them. His directory became a valuable resource that allowed him to establish relationships with all the entrepreneurs in town and add value to them by providing aggregated information about where to buy goods and services.

Adolph was selling information that, for the most part, was readily available to everyone in Chattanooga. But by compiling it and making it easy to use, he created something of value that others were happy to pay for. It’s not exactly the same, but it reminds me of how Michael Bloomberg took publicly available bond market data, centralized it, and made it easy for people to make buy-and-sell decisions around bonds (more here). The information product is still, as of this writing, the anchor of his empire and over $100 billion fortune.

It’s interesting how these two information entrepreneurs took a similar approach when they started out though there’s a 100-year gap between them.

I’m curious to learn more about Ochs and how all this led him to The New York Times.

Yesterday, I shared what I learned about how much of the company each Netflix cofounder owned (see here). I also learned from reading Netflix’s S-1 document that VC firm Technology Crossover Ventures (TCV) owned roughly 43% before the IPO and roughly 34% after it. I learned that TCV partner and cofounder Jay C. Hoag has been a Netflix board member since 1999 (see here). Jay and TCV invested before the IPO, so they’ve seen the company go from a promising start-up worth tens of millions to a global, publicly traded company worth over $400 billion.

I view investors who found investment firms as entrepreneurs, so I was curious to learn more about Jay and TCV. I’m early in my research, but I found Jay’s interview (listen here) from 2021 on the Invest Like the Best podcast. A few things I found interesting:

• Netflix stock traded down 15–20% after the 2002 IPO and stayed down for about six months.
• TCV was founded as a private and public (i.e., “crossover”) investor. This means that it invests in private technology companies (i.e., start-ups) and technology companies traded publicly on the stock exchanges.
• In 2011, TCV made a PIPE investment in Netflix after the stock had declined 70%. The stock traded down further after the PIPE investment, which was for $400 million, with T. Rowe Price participating, too. More details are here and here.  
• “By being a private investor, it made us better public market investors” and “By being a public market investor, it made us better private investors.”
• “The capital allocation exercise is to look across the technology landscape, take advantage of all the research and knowledge that we have, and look for the best investment . . . and not be bucketed by either private or public.”

Jay and TCV also invested in Zillow, Peloton, Facebook, Airbnb, Tripadvisor, Spotify, and many more wildly successful technology companies. I’m excited to learn more about Hoad and what led to his outsize success.