I’m knee-deep in experimenting with the “Entrepreneurs” page on this blog. I’ve been talking to people to figure out the best way to present the list of entrepreneurs and the details on a dedicated page for each entrepreneur. The two pages I have up now are for testing layout ideas and getting feedback from friends.

I’m a fan of copying what works, so I’ve been doing some research. Surprisingly, I haven’t found any great lists of entrepreneurs that aren’t based on net worth. Bloomberg Billionaires Index and Forbes Billionaires are well formatted and insightful. The list of names is easy to go through, and each entrepreneur has a great profile page. The main hook to get you to click on each page is their net worth or the source of their wealth (for many, the company they founded). So, these two do a great job but focus only on the richest people in the world. Other lists I’ve looked at that aren’t based on net worth aren’t high quality from a presentation perspective.

I like some visual aspects of how Bloomberg and Forbes present their lists. They’re clean and simple. Each person’s profile page is laid out well (I love the Bloomberg layout). But wealth is the anchor, which isn’t what I want for my page. I’m going to have to figure out what my anchor will be and how to get people interested in learning more about the entrepreneurs without making it all about their wealth.

Today, I had another two-hour focus session via video. This is the second one I’ve had (see here for learnings from the first one). It was a little different—we started at 8 a.m. I usually don’t take meetings early in the morning because I want to protect the time when I’m most productive (I’m a morning person). But I want to show the software to a few people at a conference in a few weeks and we have a lot to get done before then, so 8 a.m. it was! A few takeaways from today:

• I created a document with system instructions and a process diagram that my developer friend needed to understand before he started writing code. We spent a few minutes walking through it. I’m not sure if that was time well spent—I might have been able to do a Loom video, which he could have watched beforehand. Then we’d address any questions and try the system instructions in the AI studio together before he started coding. The Loom video would be good documentation that’s useful later for other developers. It might have saved a little time (though not a lot) and produced something that would be useful later.
• During the last ten minutes of the session, we both shared what we’d gotten done, discussed our plan for the next session, and identified the blockers each of us should remove before then. Those blockers became to-do lists. For example, he needs me to write another system instruction, so that’s on my list of things to do before our next session later this week.
• Starting at 8 a.m. felt good. Since this wasn’t a traditional meeting but rather a focused working session, I felt like it was a good use of my most productive time. I got a bunch of stuff done in two hours, which is my objective with my morning time. We were done by 10 a.m., and I felt good and in a productive groove. I worked on another project until lunch and got a lot done on it, too. The two-hour session made my morning more productive.

I’m not sure what to call these sessions—my developer friend calls them “pair programming”—but I’m a fan of them. I wasn’t sure about the 8 a.m. start time, but it worked surprisingly well. I think having a bit of structure at the beginning and end of each session helps us get the most out of them by setting expectations and clearly defining the next action each person must take before we meet again.I’m looking forward to the next session.

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: 48
• Total book digests created: 15
• Total blog posts published: 301
• 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 Donald Miller’s Building a StoryBrand 2.0: Clarify Your Message So Customers Will Listen, a framework book about marketing storytelling and messaging  
• Created a system instruction to guide a LLM through a defined workflow
• Created a new, lucid chart to document the above process flow
• Created an “Entrepreneurs” page on the blog to test ideas about presenting data
• Started creating the data structure for other types of data to be presented on the blog
• Started testing various marketing ideas on this blog; see here

What I’ll do next week:

• Read a biography, autobiography, or framework book
• Get feedback on the problem, vision, and mission statements from two seasoned entrepreneurs
• Create a concise hypothesis statement  
• Share the draft taxonomy with two people
• Continue linking blog posts about the same book
• Continue updating descriptions for blog posts about the same book

Asks:

• None

Week two hundred fifty-three 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:

• I didn’t make as much progress on my tasks related to software development as I wanted to this week. We had some good breakthroughs on getting the UI and website to visualize data from the software. I ran hard in that direction, given the momentum (and excitement), but it came at a cost: less progress on the software. I need to figure out how to keep all areas moving forward consistently.

What I learned:

• I still need to work on my pitch. I was rambling when I pitched on the fly twice this week. See more here.
• The Bloomberg-terminal-for-entrepreneurs analogy resonated well during the above-mentioned pitches. I’ve added it to the marketing message list.
• I’m using this blog as a laboratory to test marketing messages and strategies that will help with this project.
• I haven’t figured out a way to show the data from the database in a way that doesn’t overwhelm users. Also, we’ll have lots of data, but I don’t know what information they’ll value most. This blog is a good way to learn by testing. I’m adding new pages to this blog. Hopefully, people will find them useful. If not, I’ll adjust them until they add value. Stay tuned!
• Before entrepreneurs invest time into learning about another entrepreneur, they want to know why it’s worth it. They want to establish credibility before investing time. Quantifying the other entrepreneur’s company size through revenue, profits, or the amount their company was sold for are common data points entrepreneurs look for to establish credibility.
• Building a custom platform to display information from the database doesn’t make sense at this point. There are web platforms with good-enough functionality that can be updated via an API from our database.
• Creating the software that houses the information from biographies is a different project than presenting that information in a way that’s useful to others. The two projects complement each other, but they have different objectives. One is data, and the other is more media-ish. How revenue can be generated from each is different, too. These might need to be two different companies.

Those are my struggles and learnings from the week!

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.

Today, I was leaving a coworking space when two entrepreneurs independently struck up conversations with me. Entrepreneurs love to hear about what peers are working on; it’s their version of talking shop. Both asked me the customary “What are you working on?” question. It was an opportunity to test out my new problem and vision statements, so I dove in. A few takeaways after reflecting on both pitches:

• Problem statement – Having the wording for the problem statement nailed down helped tremendously. Both entrepreneurs quickly grasped the problem. This is the most important part of any pitch.
• Rambling – I caught myself talking too much after I’d described the problem. I was excited about this project, and that energy translated into some rambling. I need to control my excitement and pause to allow the other person to ask questions so it’s a conversation, not me vomiting on them.
• Elevator pitch – I need to develop a thirty-second elevator pitch. I have the pieces of it, but I need to hone it, memorize it, and have it ready. I didn’t have that, which contributed to the rambling.
• Reps – I was a little rusty overall. Putting your problem statement, vision, etc. down on paper is different than pitching them live. Getting more reps is what makes the pitch crisp. I need more reps. I’ll likely go to some pitch practice sessions the coworking space offers.
• Connection – People have a personal connection with books. One person today told me he chose his career after reading a biography as a child. His career mirrors that of the person he read about. If the person I’m pitching has a connection with books, I should explore that up front and lean into it during my pitch.
• Analogy – I tested an analogy today. I said I’m building the Bloomberg terminal for entrepreneurs. I’m not sure why; it just came out during my verbal ramble, so I ran with it. Surprisingly, it landed well. Both people got it instantly. I’m not sure if I’ll use it going forward, but it’s good to know it’s there.
• Stay ready – I wasn’t planning on pitching today, but it happened twice in five minutes. My takeaway is to stay ready to pitch.
• Energy – I was excited and had energy because I’m excited about what I’m working on (and I finally know how to communicate it, lol). My energy got my listeners excited too. I’m usually a laid-back, easygoing person, but I need to embrace and share the energy this project gives me.

That’s it. That’s what I learned from pitching on the fly twice. I didn’t bomb, but it wasn’t as good as it could be. There’s more work for me to do on my pitch. It feels good to be back in the early-stage founder mode.

On January 7, a friend told me about a way to host an AI model on my local computer. He said it could be a cheaper alternative to running in the cloud with Google, AWS, or Azure for my software project. I told him the MVP wouldn’t be used by many people, so for now we’d host in the cloud to move faster. The company he suggested was DeepSeek, and I looked into it a bit that day. It was promising, but I decided to investigate more after my MVP is ready.

Well, on January 20, DeepSeek released a new open-source model that caused a storm in the tech community. It allegedly beats OpenAI in reasoning. This new model was reportedly created with only $6 million and significantly fewer chips for training. Other models are rumored to cost over $100 million to build and require tons of chips.

This chatter picked up significantly this weekend and caught my attention. Then, the DeepSeek app became the most downloaded app on the Apple app store this weekend. This morning the stock market took notice and sold off sharply. Bloomberg says that today, $1 trillion in value was erased for public tech companies and wealthy individuals lost over $108 billion (see here and here). NVDA alone lost roughly 17% in market value today, which means it lost over $500 billion in value in a single day (see here). That’s a record stock market drop in value of a single stock in a single day.

I haven’t played with DeepSeek yet and don’t fully understand all the implications of this open-source model performing better than OpenAI, but I’ll do some digging and have some conversations this week to learn more.

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: 47
• Total book digests created: 15
• Total blog posts published: 294
• 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 John Train’s Money Masters of Our Time, a biographical anthology about seventeen public market investors
• Updated class diagrams showing proposed linkages between various classes (tables) in the database
• Successfully extracted the first data type from a book via code—my developer friend led this and wrote the code to do what I envisioned
• Created UI for MVP—my developer friend wrote code to make this match the requirements I documented

What I’ll do next week:

• Read a biography, autobiography, or framework book
• Create a comprehensive system instruction to guide LLM through a defined workflow
• Get feedback on the problem, vision, and mission statements from two seasoned entrepreneurs
• Create a concise hypothesis statement  
• Share the draft taxonomy with two people
• Continue linking blog posts about the same book
• Continue updating descriptions for blog posts about the same book

Asks:

• None

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