Posts from 

March 2025

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Why John H. Johnson Was a Bootstrap Genius

One of my favorite entrepreneurs is John H. Johnson. He was a publishing entrepreneur who created Ebony and Jet magazines. Both were iconic magazines in the Black community for several decades. Johnson bootstrapped his company, and by 1987 it was doing over $174 million in annual revenue—almost $481 million in 2024 dollars. Johnson’s autobiography was one of my favorite reads last year. I bought several copies and wrote a five-part deep dive on it (see here).

I wanted to learn more about Johnson and found Empire: The House That John H. Johnson Built, a biography of him. It was written by Margena A. Christian, who used to work at Johnson’s Johnson Publishing Company.

I’m still reading the book, but a few things have caught my attention:

  • Start-up capital – Johnson “borrowed” the customer list (20,000 names) of the insurance company that employed him. He then wrote a letter to every customer asking them to prepay for a subscription to a magazine he hadn’t created yet. Three thousand people agreed to pay $2, giving him $2,000 in start-up capital—more than $100,000 in 2024 dollars. This biography highlighted Johnson’s copywriting in that letter. He worded the sales letter in a highly effective way and made people want to buy, sight unseen. Johnson noted that this letter was so unique that he could never replicate those results.
  • Curation – Johnson’s first magazine, Negro Digest, didn’t include any original articles. He aggregated all its articles from various publications about Blacks. Making information readily available in a single place made his first magazine successful.
  • Cloning – Johnson didn’t try to reinvent the wheel or create something new. He “borrowed” from successful magazine formats and used them to communicate to the Black community. Life magazine was a picture-based magazine that was wildly successful. Johnson used that format when he launched Ebony magazine.

Those are some of my early takeaways from the book. I’m looking forward to reading the rest of it.

I'm Looking For a Developer

My developer friend has been helping me, nights and weekends, to build the first version of my software. He has his own start-up but was intrigued by the challenge of my project and took it on as a side project. It’s been a great experience; we’ve both learned a ton. He’s deep into artificial intelligence (AI) and building systems to manage large data sets, so he was a terrific fit. It was great to have someone with the right technical experience who could complement what I envisioned. We should have a hosted version of that first product version done this week.

My friend’s start-up is hitting a critical point, and he has less free time, so he won’t be able to devote programming time to my project going forward. I’m appreciative of what he’s contributed thus far. His expertise led to some valuable insights. In the beginning, we had a candid conversation and set clear expectations; we agreed this day would come eventually, and here it is.

He’ll still help with my project, but it will be more high-level as time permits. That being the case, I need to find a developer who can help us knock out the last few features I envision for this project so others can play with it. If you know a talented, full-stack developer interested in building the Bloomberg Terminal for entrepreneurs, let me know. A love of reading books is a strong plus.

Weekly Update: Week 258

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: 53
  • Total book digests created: 15
  • Total blog posts published: 336
  • Total audio recordings published: 103

This week’s metrics:

  • Books read: 1
  • Book digests created: 0
  • Blog posts published: 7
  • Audio recordings published: 0

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

What I’ll do next week:

  • Read a biography, autobiography, or framework book
  • Make it possible for software to be hosted in the cloud instead of locally
  • Get feedback from five people regarding alternative layouts for a list of entrepreneurs on my blog
  • Pick layout for list of entrepreneurs and test live page with real data

Asks:

  • If you know any full-stack developers interested in working on the software for my current project, please introduce us!

Week two hundred fifty-eight was another week of learning. Looking forward to next week!

Last Week’s Struggles and Lessons (Week Ending 3/9/25)

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

What I learned:

  • Entrepreneurs who prefer listening to books struggle to create voice or written notes about important parts of books or their thinking around parts of the book they’ve listened to.
  • It can be difficult to remember to review an annotation from a book. An entrepreneur requested the ability to set an automated reminder that prompts him to do so.

Those are my struggles and learnings from the week.

Albert Lasker’s Lasting Influence on America

I’m finishing up the second biography of Albert Lasker, The Man Who Sold America. The story is set in the early twentieth century, but it’s still a remarkable one for learning about the history of the advertising industry and one of the figures who heavily influenced it and American consumption habits.

Lasker was a complex person who struggled with bouts of severe depression and anxiety. Even with those ailments, he managed to understand consumers and how to communicate to them in an unrivaled way. It took decades, but his skills and his agency’s success eventually shaped American consumer behavior and politics. Lasker’s ability to communicate messages that resonated with everyone led to him heavily influencing American politics all the way to a presidential election.

I’m glad I decided to read these books about Lasker; they’ve made me aware of a period in the advertising industry that I might not otherwise have known about. They also helped explain the strategy behind some of the advertising methods still in use today.

I’m looking forward to reading more about Lasker and others who helped birth modern advertising.

What is Advertising? Per Albert Lasker

I’m reading a second biography about Albert Lasker, The Man Who Sold America. This biography is more detailed than the first and provides more context around events and decisions that shaped Lasker’s journey. Lasker is a famous marketer who founded his own agency and is known for pioneering marketing techniques still in use today. Interestingly, he didn't want to go into advertising, but his father persuaded him to pursue it instead of journalism.

Within a year of going to work for an ad agency, the early ’20s Lasker was selling ads better than seasoned salesmen there. But he still didn’t understand advertising. His clients were spending ungodly sums to advertise, but no one could tell him what advertising is. They couldn’t define it. For context, this was 1904, so there was no internet, no television, and no radio. Only newspapers and magazines.

Lasker’s thinking was that if he could understand what advertising is, he could do an even better job of selling it to his clients. So, he asked around, but no one could really define advertising, which perplexed young Lasker. People told him it was sloganizing, it was news, it was keeping your name in front of people, and other things that didn’t make sense to him. For example, Lasker reasoned that you could keep your name in front of people, but the business could still go broke. Then one day, John E. Kennedy gave Lasker the perfect definition that set the tone for the rest of his career: advertising is “salesmanship in print.”

It was a lightbulb moment. From then on, Lasker viewed advertising as doing the same work as a salesman. It was convincing others to purchase a product. With this understanding and the help of great copywriters like Claude Hopkins, Lasker developed playbooks and techniques that changed how products were sold in ads.

This simple definition from Kennedy stuck with me too. Thinking about great advertising as salesmanship is helpful and reframes how I think about advertising. I now look at ads and think, Is this ad doing a good job of selling me a product?

Lasker had a fascinating way of thinking and a unique temperament. It’s interesting to read about how they combined to make his agency the go-to firm of his day, even during the Great Depression. I’m looking forward to finishing this book and learning more about Lasker and his lasting impact on the advertising world.

Create Titles FIRST: Here's Why

One of the presenters at last week’s Newsletter Marketing Summit discussed how to approach the creation process (videos, blog posts, etc.). I won’t go into everything, but the point that stuck with me was that you should create the title of your piece first. Only then do you create the meat of your content. Most people probably ignored this part of the presentation, but I didn’t. It was the third or fourth time I’ve heard this from a notable marketer gifted at copywriting.

Creating the title first is supposed to have a few advantages. First, packaging is important. Creating the title first means it’s not left as an overthought. You can create an amazing blog post, podcast, video, etc., but if the packaging is bad, no consumer will ever find it. Titles for written pieces are critical to generating interest—similar to what headlines did for newspapers back in the day. For videos, e.g., on YouTube, packaging includes titles and thumbnail pictures. David Ogilvy’s book was written decades ago, but it stresses the same point in relation to newspaper ad headlines (see here). I’ve been thinking more about titles since reading Ogilvy’s book, and I’m more intentional about creating the titles for each blog post.

Second, creating the title first focuses your creation process. It forces you to create something that supports the title. Said differently, your thinking and creativeness are confined to a narrow lane. You can’t wander. This is the opposite of what I do now: I write my blog posts and then try to create an interesting title.

I want to get better at selling and communicating my ideas, and this sounds like an approach that can help with that. I’m going to try writing my blog post titles first for a few posts. I’ve been following my current process for almost five years, so I’m curious to see how this change will impact my thinking and creative process.

Copywriting: Why It Matters Now

In October, I challenged myself to learn the big concepts in marketing (see here). I’m not a marketer by nature, but I figured it’s something I can get better at if I learn the big concepts. Plenty of people understand it deeply, so I read several books about people who pioneered marketing strategies and built agencies—Claude Hopkins, David Ogilvy, Albert Laster, etc. I also read a framework book by Donald Miller, which explained how to craft messages that resonate with customers.

A central thing that kept coming up in these books is copywriting. As I understand it, copywriting is the art of conveying a message in a way that increases the chances of the reader purchasing.

When I attended the Newsletter Summit last week, copywriting appeared again in some strategy sessions. Many newsletters sell advertising, so it makes sense that copywriting is top of mind for many newsletter entrepreneurs whose revenue is based on advertising. Advertisers want readers to convert into customers. If that doesn’t happen, they stop advertising. The strategies these entrepreneurs use to test and optimize their copy are impressive. But when I zoomed out, I saw that they’re using the same strategies as Hopkins and Lasker while using tactics optimized for today’s digital world.

I still have a lot to learn about marketing, but I see the value in effective copywriting. Right now, my gut tells me that it’s a bit art and a bit science. But we’ll see if that’s confirmed or denied as I learn more about it.

Learning Library: Early Feedback

It’s only been a few days since I shared my blog’s new pages (see here, here, and here), but I’ve been gathering feedback. Today, chatting with an entrepreneur, I showed him the searchable list of all the books I’ve read—or My Learning Library, as I call it now. I showed him how he can see each book's profile page and the connections between books on a profile page.

His initial feedback was that My Learning Library is a well-curated list of books. Having all the books on one page eliminates his usual need to search for and research books, which adds friction to his process of finding books to read. Instead, his mind went straight to wanting to purchase a few of the interesting books using the links on my blog.

Selling books isn’t my goal. I want to make it easy for entrepreneurs to find books that can help them solve problems faster or that they’ll enjoy reading for pleasure. It’s early days, but providing a curated list of what I’ve read seems to be accomplishing this.

I like the connections between books and blog posts on the profile pages. Building this out was a decent lift. I think it’s great for discovery. It’s an easy way to follow breadcrumbs between books. I want to get more feedback from people to find out if they see this feature as valuable.

Weekly Update: Week 257

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: 52
  • Total book digests created: 15
  • Total blog posts published: 329
  • Total audio recordings published: 103

This week’s metrics:

  • Books read: 1
  • Book digests created: 0
  • Blog posts published: 7
  • Audio recordings published: 0

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

  • Read Growth Levers and How to Find Them, a framework book about finding the right strategy to acquire customers by Matt Lerner
  • Attended Newsletter Marketing Summit
  • With the help of my developer friend, finished the first version of the software; although it ran locally on his computer, we couldn’t get it to run on mine, so I couldn’t demo it at the conference
  • Finalized descriptions of all the books I’ve read so far and updated them on this blog
  • Published my 2024 Reading List page on my blog; see here
  • Published a searchable library of all the books I’ve read, which I’ll update weekly; see here
  • Published a book profile page for each book I’ve read showing the connections between books, blog posts, and more; see here
  • Showed the pages on my blog to several people at the conference and got feedback
  • Pitched the software idea to roughly twenty people and obtained contact information of five people interested in seeing the software

What I’ll do next week:

  • Read a biography, autobiography, or framework book
  • Conference follow-up
  • Make it possible for software to be hosted in the cloud instead of locally

Asks:

  • None

Week two hundred fifty-seven was another week of learning. Looking forward to next week!