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.

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.

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.

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!

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:

• At the conference I attended, the goal was to show off an early version of the software and an MVP of a book directory built on my blog (My Learning Library). The blog feature was done, and people were impressed when I showed it to them. The software was finished the morning of the conference, but it was designed to run locally, and we couldn’t get it to run on my computer. It was frustrating to not be able to show it to people. I had to pitch it without demoing it, which went over decently. A few people are interested in seeing the demo.

What I learned:

• I tested a name at the conference, “I Study Entrepreneurs,” and it did well. I’m definitely using that name in the future.
• Discovery platforms and relationship platforms are materially different. Discovery platforms have algorithms that help people find you. Think TikTok or Instagram. The downside is that you don’t own the relationship with the user. It’s borrowed distribution, meaning someone can change your ability to reach people anytime. Relationship platforms give you a direct relationship with a user that you own, but discoverability is much harder. Think blogs, newsletters, or SMS. This is owned distribution, meaning no one but you can change your ability to reach users (mostly).
• Several entrepreneurs’ entire business model revolves around creating content that’s a deep dive on a person, industry, or topic. I met a few of them at the conference.
• Buying local newsletters that people are running as side projects and scaling them is a strategy that can do well.
• A newsletter can be a great growth engine if you sell products or software. If you’re savvy, you can convert your newsletter marketing from a cost center to a profit center by paying to acquire subscribers and getting paid to make them aware of other products or services.
• I learned a ton more from conversations and presentations!

Those are my struggles and learnings from the week.

Last year, I read a lot of biographies about media entrepreneurs. I knew nothing about the industry and wanted to understand it and the people in it better. All that reading totally changed my perspective. Media is an industry that I now have an appreciation for and wish I’d studied when I had my e-commerce company.

My research led me to a subset of the industry: email newsletters. As I dug into newsletters, I discovered newsletter entrepreneurs building massive businesses (tens of millions in annual revenue). A couple have sold in the last few years for ~$30 million and ~$75 million.

I’m interested in learning more about newsletters because I think they could be an effective way to market the software I’m building and to share what I’m learning from the biographies I read. I also want to meet the entrepreneurs in this space and see the industry behind the scenes. Last month, I learned about the Newsletter Marketing Summit and decided to attend as a way to check all these boxes.

The conference wrapped up today. It gave me exactly what I was looking for. I met some amazing newsletter entrepreneurs who shared the secret strategies that led to their success.

I’ll digest my notes and the presentations in the coming days, but here are a few initial takeaways:

• Advertising  – Generating revenue from advertising was emphasized. This makes sense given it’s media, but advertising revenue is new to me. I learned a ton. Side note: I heard several conversations about advertisers pulling back.
• Metrics – Lifetime customer value and customer acquisition cost were also discussed a lot.
• Early – This industry isn’t developed and structured. It had an upstart and wild west‑ish feel to it. It’s getting harder to build a newsletter business, but I get the feeling that it’s still early days.
• Newsletter mafias – A lot of the successful people in the space were early employees at a handful of companies, including The Hustle and Morning Brew.
• Scalability – You don’t need a huge team to have a sizable newsletter. One presenter is doing over $21 million in annual revenue and has only 21 employees. That’s $1 million in revenue per employee, which is amazing.

I saw some great, eye-opening presentations. I’m going to dive into reviewing them and likely will share insights from them later. I didn’t know what to expect from this conference, but it was a great event and I’m glad I attended.

I’ve been working on a project to share more about the books I’m reading. It all started with my frustration around how painful it was to share the books I’d read in 2024 (see my post here). Two days ago, I shared a list of the 52 books I read in 2024, sorted by month (see my post here). Yesterday, I shared My Learning Library, a searchable list of all the books I’ve read, and I’ll update it weekly (see my post here).

Those were all lists of books, but I built something else, too. Today, I’m sharing the third part of this project: Book Profile Pages. Each book I’ve read has a dedicated page on my blog that includes a description, my notes, and other information about the book. The stories of entrepreneurs often overlap. It’s common for entrepreneurial biographies to describe deals or battles with other entrepreneurs. They also mention other books (I find most books I read this way). But it wasn’t easy for me to see those connections visually, so I built Book Profile Pages to solve this problem. It’s something I hope other people find helpful because it makes it easier for them to discover books and other information about people they’re interested in learning more about.

To see examples of book profile pages, check out the page for The Gambler, a biography about Kirk Kerkorian. This biography helped me discover another entrepreneur, Billy Wilkerson, and I read two biographies about him. Another example is A Passion to Win, the autobiography by Sumner Redstone. See the profile page for A Passion to Win here.

This is the third part of this project that I’ve shared this week, but the project isn’t done yet. I need to do more work on other parts before sharing them, which I hope will be in a few weeks. In the meantime, I hope the book profile pages and other pages I launched this week are useful!

In yesterday’s post, I shared that my 2024 reading list is live and that creating that list led to a much bigger project. I realized I don’t just want to share my reading list at the end of each year; I want to share it in real-time. I want people to know what I’m reading every week, not once a year. I want people to be able to see the personal library I’m building to help me learn.

So, today I’m sharing the second part of this project: My Learning Library. This is a searchable list of all the books I’ve read, and I’ll be updating it weekly. It includes a description of each book, my notes about it, and when I read it (some I’ve read multiple times).

If you want to see a list of the books I’ve read in 2024 and 2025, check out my learning library here!

This is the second part of a bigger project, but there’s still more that I’ll share in the coming days.

On January 3, I shared my reading stats for 2024 (see here). After I wrote that post, I realized I wanted to share a list of the individual books—and how hard it is to do that (see here). I tried creating lists in GoodReads and played with creating something in Airtable, but I didn’t like those options. I wanted something that didn’t require updating another platform and that would look good visually on my blog. So, I ended up building something, which turned into a bigger project than I’d planned for.

To create this reading list, I had to create a database with lots of details on each book. Some of that I shared here. But the thing I underestimated most was creating descriptions for each book (see here). Most of that tedious work is now done (I still have a few descriptions I need to clean up).

I’m sharing the first part of this project today: my much-promised 2024 reading list. This is a list of every book I read; it includes a description of each book, my notes on each book, and the month I read it.

So, if you’re interested in seeing the 52 books I read in 2024 and what they’re about, take a look here!

Like I said, this is just the first part of a bigger project. I’ll share the rest of it in the coming days, but hopefully this 2024 reading list will be helpful.

Early-stage founders often take one of two paths. Sometimes they lived a problem and used their experience to build a solution and market it to people like them. Other founders learn about a problem and then must learn more about it to figure out what solution to build. You can do both, too, but that happens less frequently.

If a founder has lived the problem, they are the customer. They’re building something for themselves and people like them. If founders haven’t lived the problem, they need first to understand it from the customer’s perspective. To do this effectively, ideally before they start building, founders would be well served to do customer discovery interviews. Simply put, they should interview customers to understand a problem from their perspective and, ideally, uncover unique insights about a problem. When done correctly, customer discovery saves time and resources by preventing founders from building something customers don’t want.

Customer discovery is more difficult than it sounds because founders want to tell everyone about their ideas. This process isn’t about the founders’ ideas; it’s about the customers’ problems. So, founders have to go from sell mode to listen-and-learn mode, which isn’t always easy. Ideally, the founder’s ideas shouldn’t even be mentioned during customer discovery conversations.

Luckily, there’s a great book written for founders that details a framework for conducting effective customer discovery interviews. It’s called The Mom Test. I’ve read it a few times and gotten value from it each time. Whenever I want to learn about a problem, I refresh myself on the framework. It reminds me how to ask questions in a way that leads to my gaining a better understanding of the problem, which leads to unique insights and creative ideas about how to solve the problem.