AI is a hot topic among entrepreneurs right now. It’s a fantastic technology that makes the previously impossible possible. In the last few weeks, I’ve talked to several founders who want to use AI in their companies. They’re thinking along the lines of chatbots and other features. This struck me as odd because it’s not clear if these things would add value to their customers.

After I left one of these conversations, I realized that the founder is building technology in search of a problem. To his credit, he knows that AI is powerful and can change his company and benefit its customers. But he just doesn’t know enough about the technology to determine how to apply it in his business. So, he defaulted to building what he’s seen be successful at other companies: chatbots and the like.  

Companies exist to solve problems. By solving problems, they add value to customers, and customers pay them for that value. If a technology doesn’t help a customer materially or help you help the customer, what’s the point of using the technology in your business?

AI is powerful, and all entrepreneurs should explore and use it in their businesses. I think the best approach to adopting it, if you’re unfamiliar with it, is to pinpoint a problem that’s painful for you or your customers—one that you can’t solve or that’s painfully expensive to solve. Then, search the numerous AI tools for one that can help you solve that problem. Evaluating each AI tool to understand whether it can do that will expose the limitations of each tool and the technology as a whole. This process will accelerate your AI learning and help you get comfortable with the technology.

This approach will help you create a better solution for yourself or your customers and give you a deeper understanding of AI capabilities that you can use to solve future problems.

Yesterday, I shared that I caught up with a friend who’s a serial entrepreneur and avid reader. He’s serious about learning and solving problems, so for years he’s made reading a priority. He has time on his schedule early every morning to read books (I do too).

Today, I’ve been thinking about another takeaway from that conversation. One of his book discovery methods is paying attention to other books mentioned in the books he reads. (Many books cite other books when they borrow concepts.) He likes this approach because an author doesn’t usually mention a book if it isn’t worth reading or it’s not helpful—a mention is like a quality filter. Also, the suggested book will likely align with the period, industry, or person he’s studying. Suggested books allow him to go deeper into an area he’s already learning about. They keep him on topic.

I, too, use books to discover books (see here), so this resonated with me and got me thinking.

The pain point around this approach is that you must read a book to find the suggested books. The suggestions are like needles in a haystack. This isn’t an issue with a book I’m currently reading, but what If I want to know what books are mentioned in a book I read awhile back? Or what if I find a book and want to see what books mention it to determine its quality? As far as I know, that’s impossible. It’d be great to see a list of all the books mentioned in a particular book and a list of all other books that mention it. Books are connected, but it’s impossible to see the connections. Visually displaying those connections could unlock lots of value for readers and make it easier to discover useful books.  

Today, I caught up with a friend who’s a serial entrepreneur. He’s an avid reader, so I told him about my book project and asked him a few questions about his reading habits. One insight is something I’ve heard from other entrepreneurs who like to read.

He reads physical books and reads on a Kindle, but he prefers the former. However, when he reads a physical book, it’s too time-consuming to retype sections he’s highlighted into his note-taking app. He reads on a Kindle because he can highlight with his finger and sync to his note-taking app. The problem is that he doesn’t like reading on a Kindle—but it’s the lesser of two pains.

I’ve not only heard this from several entrepreneurs, I’ve lived it. Getting notes out of physical books so they can be reviewed later is painful for me (see here). I endure the pain and read physical books, but I’m determined to solve this problem. If I do—and do it well—I think other entrepreneurs who are avid readers will embrace the solution!

Tariffs and the stock market decline after they were announced were all over the media late last week. I lived through tariffs with my e-commerce company, and it wasn’t fun. I learned valuable lessons about how tariffs impact wholesale and retail markets for physical goods, especially for the automotive parts we sold online.

I was curious about how entrepreneurs think about tariffs, so I talked to a few e-commerce entrepreneurs, who are also friends, this weekend.

A few things I learned:

• Entrepreneurs in retail (online and physical) are worried about tariffs because they can’t absorb the cost of tariffs—they have to pass the cost on to customers.
• All the entrepreneurs saw sales soften in the last quarter or two before the tariff announcements. The tariffs feel like a double whammy.
• Customers are asking when or if prices will increase because of tariffs.
• All the entrepreneurs are looking at ways to do more with less and exploring whether AI can help.
• They’re all pausing any spending on new growth initiatives.
• They all recognize that they can’t do anything about the tariffs and aren’t dwelling on them—but they’re monitoring developments like hawks and navigating them as best they can.

Tariffs are a big deal for e-commerce companies whose products aren’t manufactured in the US. I’m curious to see how this all plays out, and I’m mentally preparing myself to pay more for physical goods.

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: 57
• Total blog posts published: 364

This week’s metrics:

• Books read: 1
• Blog posts published: 7

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

• Read The Father of Spin, a biography of entrepreneur—and maybe even father of public relations—Edward Bernays  
• Connected with two more developers about this project
• Played with Gumloop and Lindi; I’m trying to find an invitation code to Manus

What I’ll do next week:

• Read a biography, autobiography, or framework book

Asks:

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

Week two hundred sixty-two 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

What I learned:

• Creating a language model isn’t as expensive as I thought if the data set isn’t large or broad.
• I should pare down the features I want before sharing the software. Giving users something that adds value is better and allows me to get feedback sooner.

Those are my struggles and learnings from the week.

This week I finished a book earlier than I expected, so I picked up another one. I usually wouldn’t have read it because of how short it is, but I figured, why not. I’ve just started it, but already it’s changed how I think about myself as “not an idea person.” The book is a framework book that details a process for producing ideas.

Already I’ve had a few lightbulb moments—a sure sign that the book is connecting dots for me and adding value. I’m going to finish it, digest it, and then share what I learned in a post.

The thought that I might be able to generate ideas repeatedly using a proven method has me excited about finishing this book and applying what I’ve learned.

Today, I talked to an entrepreneur who’s a dentist. Over the last decade, he’s steadily grown the business to about 20 dental offices (each office does ~$1 million in annual revenue). To date, he’s used bank loans and hasn’t raised from investors, but he’s considering raising growth capital to accelerate growth and build his company to more than 100 locations.

During our chat, he shared that he recently stopped seeing patients. That decision completely changed his business. He realized that for many years he’d been a full-time dentist and a part-time CEO. He wasn’t giving the business the attention it needed. He didn’t have the bandwidth to work on long-term or strategic planning. He was too busy working in the business, seeing patients.

Now that he’s a full-time CEO, he sees the opportunity ahead of him more clearly, and he realizes he needs to raise eight figures of growth capital to turn his vision into reality.

His insight reminded me of the difference between working in the business and working on the business. For years after I started my company, I was deep in operations to keep the company going. Once I hired more people and removed myself from operations, we grew rapidly. I was finally able to think higher level and longer-term. I identified growth initiatives and focused on making those projects successful so the business could grow.

Like this dental entrepreneur, I didn’t realize for years that to grow my business, I needed to be working on it, not in it.

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.