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.

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.

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 finished rereading Junk to Gold: From Salvage to the World’s Largest Online Auto Auction, an autobiography about Willis Johnson’s journey to build Copart. Its Amazon and Goodreads reviews were extremely positive: 4.8 and 4.4 stars, respectively. (I haven’t read many books rated that highly.) I’ve read many biographies since I first read this one, and this time, I wanted to understand why the book resonated so well with readers—I wanted to deconstruct his storytelling.

I figured out why readers enjoy this book so much. It’s simple, but genius. The story is told chronologically, which is ideal and not new. (Phil Knight mastered chronological storytelling by naming each chapter in Shoe Dog after a year in his journey.) But Johnson presented his story differently.

In most chronological biographies, each chapter represents a period in the subject’s journey. The reader is left to identify the important parts of each long segment and figure out why they’re important. The reader has to think a lot.

In Johnson’s book, in each chapter, he presents several lessons he learned during that segment of his journey. He titles the lesson (e.g., “Admit Your Mistakes”) and then includes a short story to explain how he learned it and the result.

The genius of this approach is that the reader doesn’t have to think. The big takeaway (i.e., the lesson learned) is stated clearly, and reading the story reinforces the lesson. This helps readers learn more of the valuable things Johnson learned.

This method eliminated any fluff; the book is short, only 172 pages. I think Johnson’s book is so highly rated because it delivers maximum value in a few pages (relatively speaking) and doesn’t require readers to figure out what’s important or why.

I like Johnson’s approach, and I’m thinking about how to use it in my project. Snippets of lessons learned supported by short stories is a great way to communicate with entrepreneurs. It might even be a framework I can use to concisely communicate the most important info from biographies.

I’m still on my journey to learn about marketing (see here). One way new companies can market is by defining their ideal customers (and the problem they solve for them) clearly and then figuring out where those people hang out. Instead of attempting to attract them to an unknown brand, go find them where they’re spending time and introduce your solution and brand to them.

So, how do you do this in a way that isn’t spammy and that builds trust in your solution and brand? I had a rough idea but wasn’t sure, so I did some research. I came across a video that gave a great tactical explanation of how a new company contributes to Reddit posts to market itself. Here are a few of my takeaways:

• The goal isn’t to siphon traffic from communities; it’s to become a respected member who adds value to the community.
• Being a respected community member is a long-term strategy, not a quick fix.
• Most people lurk in communities. Contributing is a way to stand out and attract people to you.
• On Reddit, in-depth responses to posts do well.
• Social status in online communities like Reddit and Hacker News is based on how much you contribute.
• Building credibility first is important. It can take months or even a year.
• When you’re contributing to a community, you never know which post will add outsize value to the community and increase your standing in it.
• Because specifics and details that aren’t normally shared or known are so hard to find, people love them.
• Each platform has a unique culture. Learn the culture of the platform

This is tactical advice, but I found it useful. I like the concept of contributor marketing because you lead with adding value to others, which feels more authentic and the way to earn not just customers but people who are fanatic about your company.If you want to watch this part of the interview, see here.If you want to see the Reddit post where some of the above learning originated, see here.

I’m finishing up Building a StoryBrand 2.0: Clarify Your Message So Customers Will Listen by Donald Miller. The book is about a framework for communicating your company’s solution and value add in a way that resonates with customers. A framework is an approach to thinking about problems in a way that increases your chances of identifying a superior solution. I’ve been embracing frameworks, and I now view them as valuable thinking tools that lead entrepreneurs to better solutions in less time.

Miller describes the psychology of customers, what strategies can influence their perspective of a company’s solution(s), and what’s needed to get them to act (purchase or take the next step in the sales process). One of Miller’s principles is that every person is trying to avoid failure. If you can communicate to customers the downside of not using your solution, you position yourself as helping them avoid failure.

Miller, expanding on this idea, shows that one reason it works so well is human psychology—specifically, loss aversion. Loss aversion is a cognitive bias. People perceive losses as being more significant than gains. Someone can lose $1 and then gain $1, but the lost dollar will feel more painful than the dollar gained will feel pleasant, even though the amount lost and the amount gained are the same.

If you can communicate the downside to not using your solution (lost status, time, etc.), your customer will want to avoid that loss and will be more inclined to purchase.

Loss aversion is a real thing, something I’ve noticed in myself when investing. Losses are inevitable when investing. I know this and expect them to be part of the process (but not too large). But when I’ve lost money in the past, it feels more painful than an equivalent gain feels pleasant.

I’d never considered loss aversion as a potentially useful strategy in marketing messaging, but Miller’s point makes a lot of sense. Now that I know this and I’m paying attention, I see this strategy in lots of ads.

Tying marketing messaging into psychology made things click for me, given that psychology is another topic I’m actively learning more about. Interestingly, Charlie Munger talked about loss aversion, and its implications for decision-making, a good bit in Poor Charlie’s Almanack: The Essential Wit and Wisdom of Charles T. Munger. When multiple people who are credible say to pay attention to something, I take heed. Loss aversion is a cognitive bias I’ll consider more heavily in my decisions and marketing.

I’ve been learning a lot about marketing lately. It’s my Achilles’ heel, but I want to change that. To learn the big concepts in marketing, I’ve been reading books, listening to and watching podcasts on YouTube, reading newsletters, etc. I’m even debating attending a conference on written marketing, something I never would have done before.

Knowledge and wisdom are different. Here are my thoughts on this from an old post:

Knowledge is acquired by learning new information or being made aware of something. Learning about marketing is an example of acquiring knowledge. Knowledge acquisition doesn’t always equate to adding value. There’s another step.

Wisdom is the ability to apply knowledge in a manner that aligns with the outcome you desire. Wisdom means changed behavior and improved decision-making—knowing what to do and when to do it. Wisdom is acquired from experience (yours or someone else’s). Growing your company through marketing execution is the result of wisdom.

I’m now trying to move from acquiring knowledge about marketing to gaining wisdom. I’m getting experience by applying my knowledge and running tests on this blog. Here are a few things I’ve been doing:

• Titles – David Ogilvy’s books (and my most-read blog post in 2024) helped me understand the importance of titles. The content can be great, but if no one is curious enough to read it, it doesn’t matter. The title is critical to generating curiosity. My blog post title was an afterthought before. I’d throw something together just before I published to say I checked the box. I’m now more intentional about titling and have the beginnings of criteria for my blog post titles. My titles are much better than before I learned about marketing, but I still have more work to do.
• Descriptions – Similar to the titles, descriptions were a check-the-box exercise before. Each blog post has a description that’s visible in Google search results. I’m now making it a priority to write descriptions that generate curiosity.
• Tagline – People need to know what this blog is about, so I’ve added that info to the tagline. I also added a personal flex and credibility booster by including my number of consecutive posts (1,775+!). Now people know this blog is about entrepreneurship and biographies. The messaging in this tagline might still change, but it’s better than before.
• Calls to action – Marketing is all about getting people to act, usually by buying something. I’m not selling anything, but I still want to test getting people to act through my marketing efforts. Persuading them to subscribe is my focus. I’ve never made it a priority to get subscribers, but I’m changing that. A pop-up has been added to the bottom of blog pages to prompt readers to subscribe. I’ve added some text to the pop-up to test my messaging skills. I’m trying to clarify the value add, but I don’t love what’s there now. I’ll keep iterating on this message.
• Awareness – Awareness is broader; it focuses on optimizing for search engine optimization (SEO). Titles, descriptions, and a bunch of other stuff are being refined to help make posts show up in Google and AI app search results.

Those are most of my marketing efforts underway now. I’m learning a lot from doing them. As I read and learn more about marketing, you’ll likely see more changes to this blog. Everything won’t work, and I’m OK with that. The goal is to acquire wisdom through my own experiences.

I’m a few months into conquering my Achilles’ heel: marketing (see more here). I never understood the big concepts in marketing. More importantly, I never tried to understand them. And I paid the price for it. Not understanding marketing and not hiring someone to fill that gap prevented me from growing my company past our $10 million peak. I’m confident that the company could have gone to over $100 million in annual revenue if I’d filled that gap.

I’ve been reading a lot about marketing over the last few months. Right now, I’m focusing on messaging and telling your company’s story. This means how you position what you’re selling to your customers. From lots of reading, it’s clear that the foundation of messaging (and all marketing, really) is the problem. You must be clear about what problem you’re solving.

This seems pretty straightforward, but it’s not. I went years in my last company without having a clear idea of the root problem we were solving for our customers. Lacking that, I also didn’t have a target customer profile (i.e., what people were experiencing this problem). Therefore, I didn’t know how big our market was (how many people exist that have the problem). Because I didn’t know the market size, I didn’t realize how big the opportunity was. Because I didn’t know how big the opportunity was, I hired based on where we were, not where we could go. There were more downstream implications (that weren’t good), but you get the idea.

Not having a clear idea of what problem I was solving was a major mistake. I was so focused on revenue that I missed the bigger picture. I couldn’t see the forest for the trees and missed out on building my company to over $100 million in revenue.

After learning more about the big marketing concepts, I now realize that not having a clear idea of the problem made it harder for me to understand marketing. It’s difficult to create an effective message when you don’t know how you’re creating value for customers and who those customers are.

Businesses exist to sell solutions to problems. If you’re not clear on the problem, selling (and marketing) your solution is many times more difficult.

One of the things I want to do is expand the reach of the content I share on my blog. I’ve been studying marketing for the last few months (see here), and I’ve learned that a big part of marketing is making people aware that something exists. I figure my blog content is a good way to do some more learning by doing.

One thing I noticed and have read about is that people are now posting blog-type content directly on platforms instead of directing them back to their website. Instead of sharing a link to their blog, they’re posting the blog content directly on X (formerly Twitter) or LinkedIn, for example. Apparently, if your post includes a link to content off the platform, the platform’s algorithms show that post to fewer people.

Learning this reminded me of how I started. When I began blogging in March 2020, I wanted to start in as frictionless a way as possible. I didn’t have a blog site, but I did have a LinkedIn profile. LinkedIn allowed you to post “articles,” so I started sharing my daily posts as LinkedIn articles. Those did well because of my built-in LinkedIn connections. After my writing habit was fully formed months later, I bought a domain, designed a website, transferred my old posts to the website, and started posting daily on both platforms. Then, I stopped sharing content via LinkedIn articles and started creating posts that linked back to my blog site. Eventually, I stopped LinkedIn altogether after about two years and posted exclusively on my blog.

Well, I want to test some of the marketing tactics I’m learning by helping my blog content reach more people, so I’ve been debating posting my content on other platforms. Basically, I’ll start doing what I used to do. I’m familiar with LinkedIn, so it makes sense to start posting there again. I want to learn X, so it also makes sense to post there.

The concern is that I’ll have to manage posting on three platforms—my blog, LinkedIn, and X—every single day. One is fine, but three I’m not sure about. I’ll continue to ponder it a bit, but maybe instead of going from one to three, I should go to two and then move to three after I’m comfortable with the second platform.