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!

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:

• Keeping the momentum going on projects is important. I lost momentum but got back on track this week with focus video meetings. See more about this here. Lesson learned: don’t lose momentum.
• Diagrams and charts that explain my thinking are helpful to others, especially developers. Creating them forced me to think through things that I might not have if I’d just had to explain verbally. Also, a lot of people are visual learners.
• I want to attend a conference and show the early version of the product to a few people at the conference. This conference deadline has motivated us and forced us to focus on what can and must be done before the conference. Lesson learned: Targeting industry events is a way to heighten focus and intensity. See more here.
• I need to share my posts about the biographies I’m reading on other platforms. Links on other platforms to my blog posts aren’t effective today.
• SEO is changing a lot. People are using ChatGPT and other AI apps to answer questions instead of going to Google. However, based on my testing this week, many of these AI tools seem to use Google’s search results to answer their users’ questions.
• I pitched the idea a few times this week. The problem statement I crafted over the holiday resonated with and excited listeners. That felt great. I need to trim the wording, but I can clearly state the problem, and people get it quickly.
• When Google’s Gemini releases new models, it doesn’t always make them available via API. The Gemini 2.0 Flash Thinking Experimental model just got released and is impressive. I’m using it for personal things, and I love it. We tried to use it via API for this project, but there isn’t an API for the model yet.

Those are my struggles and learnings from the week!

A few weeks ago, I read The Money Masters: Nine Great Investors: Their Winning Strategies and How You Can Apply Them by John Train. The book introduced me to T. Rowe Price, and I read his biography, too (more here). I really enjoyed learning a little about several people from a single book. I decided to make biographical anthologies a bigger part of my reading and discovery strategy (more here).

This week, I’m reading another book by John Train, Money Masters of Our Time, and I’ve been reintroduced to another investor I want to learn more about. Julian Robertson founded Tiger Management. I learned about him two years ago while exploring an idea for a studio for venture capital managers. During my research, I was lucky enough to get connected to someone who worked in Robertson’s back office during his heyday who explained to me how the operation ran with the Tiger Cubs.

Robertson was a successful hedge fund investor, and he also seeded and incubated tons of investors who wanted to start their own investing firms. These budding investor entrepreneurs worked out of his office and were known as the “Tiger Cubs.” The list of people Robertson helped in this way is impressive; it includes well-known investors such as Chase Coleman of Tiger Global and Philippe Laffont of Coatue Management.

I think Robertson pioneered a model of seeding and incubating budding investors that’s needed today. The model is clearly lucrative, as Robertson’s economics in the firms of some of his successful Tiger Cubs made him another fortune.

I want to learn more about Robertson, so I’m going to see if I can find a biography of him.

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.

The last few weeks have been full of distractions. It snowed twice in Atlanta, shutting the city down. Before that were the holidays. Traction on software development of my personal project slipped. A developer friend is helping as a favor. All of the above, plus other stuff, impacted our ability to schedule time to work in person on the project.

With snow forecasted for this week, we made a change to get going again. We couldn’t meet in person, so we decided to try a video meeting instead. But we didn’t want to have sessions where we talked. We wanted to have sessions where we got stuff done. So here’s what we did:

• We booked two-hour blocks to meet over video twice this week.
• Beforehand, we defined what we would each do during the working sessions.
• If my friend’s work depended on my completing something, I did it in advance so he wouldn’t be blocked during our session. And vice versa.
• At the end of each session, we discussed, and demoed if applicable, what we worked on.
• And we discussed what we would work on during the next session and what needed to be completed beforehand.

During our working sessions, he wrote software, and I fine-tuned class diagrams, workflows, etc. Our work didn’t overlap unless we had a question. This is where the benefit of this working style became clear to me. Instead of stopping what I was working on, sending an email or text to him, waiting for a response, and restarting work hours or a day later, I could get an answer instantly and keep working. Of course, this was true from his perspective too.

There are a few names for this type of work. Some call it “parallel working.” My developer friend called it “pair programming.” Whatever the right name, I’ve never tried it before this week, but so far, I’m a fan. We were able to get a lot done in a short time.

I was thinking about why the sessions were so effective. A few things stood out to me:

• People block out focus time on their calendars. These sessions are the equivalent of scheduled focus time on a specific project, but for a team.
• Friction and blockers are removed as soon as they arise, so more continuous work gets done.
• There’s an increased level of accountability. You can’t BS during these sessions.
• The work is planned beforehand, so sessions are execution focused, not discussions or attempts to figure out what to work on. I think this is a big reason this works so well.

I’m happy my friend suggested we work like this. I feel like it’s time spent efficiently. I’m also happy this project is rolling again.

I’ve been making daily learning a top priority for the last few years. Some time ago, I shared how I approach daily learning (see here). That list is still relevant, but the prioritization of the items has changed. I aim to read a biography a week, so that’s the method I focus on most. But I do a lot of other learning throughout the week. For example, I challenged myself to learn the big concepts around marketing (see why here) and have consumed a ton of information. I now have a better understanding of the big marketing concepts and how marketers think.

I’ve recently started creating notes documenting what I’ve learned, and from what sources. I’ve been sharing some of that with founders and friends. They’ve found it helpful. In blog posts, I share what I’m learning from books—but not non-book learning. I want to find a good way to share on my blog the best non-book information I’ve consumed.

I haven’t settled on how to do this, but an idea I’m thinking about now is a weekly list of the top five to ten sources I consumed that week and what I learned from them. I don’t want to keep good information to myself. I want to get into the habit of sharing more useful sources from which others can learn. I just need to figure out how to do it in a way that’s not a huge lift so I can do it consistently. I’m open to ideas. If you have suggestions, send them my way.

I finished reading Poor Charlie’s Almanack: The Essential Wit and Wisdom of Charles T. Munger last week. It’s a memoir and collection of famous speeches by Charlie Munger. I’d put off reading it for a while. Looking back, I regret that decision. The book unlocked a different way of evaluating decisions and exposed me to new psychological concepts—some that aren’t even taught in schools. It felt like an introduction to practical psychology for entrepreneurs and investors. I made tons of highlights and notes while reading this book.

I’ll eventually create a blog series on this book, so I won’t go into everything here. But here are a few more takeaways:

• Checklists – Countless times throughout the book, Charlie mentioned using mental checklists as a way to avoid mistakes in your decision process. Checklists are also a central part of David Allen’s Getting Things Done (unrelated) framework. My takeaway is that checklists are simple tools that are available to everyone, but they’re more powerful than people realize when used consistently.
• Multidisciplinary learning – I mentioned this in my post last week (here). If you have a narrow understanding of topics or a small tool set, you increase your risk of the cognitive bias of relying too much on one tool or a limited number of tools. Mark Twain described it well: “To a man with a hammer, everything looks like a nail.” You apply tools to situations for which they’re not appropriate and increase the chances of making subpar decisions. Broad learning about topics that interest you helps prevent this. Often, you discover nonobvious relationships between topics that others have missed, which improves your decision-making and gives you an edge. Charlie mastered this, and it led to a life of curiosity-driven learning and a billion-dollar fortune from shrewd decisions.
• Hard work – Acting and getting things done is one form of hard work. But learning and thinking is another form, one that many people underestimate. Learning and thinking are preparation. Good preparation leads to better decisions and allows you to practice “extreme decisiveness,” which is valuable during extreme uncertainty. From an investing perspective, preparation allows you to identify when something is mispriced and gives you the confidence to bet heavily based on your work, even if everyone else is selling for dear life.
• Incentives – Incentives heavily influence individual decision-making. Getting them right is critical for entrepreneurs and managers. If you want to understand someone’s actions or thought process, think about how they’re being incentivized.
• Lollapalooza effect – When two or more factors work at the same time, they magnify outcomes. This works positively and negatively. This reminded me of twin tailwinds, which I’ve noticed when reading about Henry Singleton (see here), Warren Buffett (see here), and 2021’s IPO explosion (here). These are lollapalooza-effect examples that led to massive wealth creation.
• Mastering wisdom – Mastering the best things others have figured out is a discipline. It’s also a hack. Trying to figure out everything from scratch on your own is hard to do, and most people aren’t smart enough to do it (Charlie’s words, not mine). It’s better to take what others have figured out and build upon their wisdom. Everyone can do it, but many people won’t because it requires a passion for learning and curiosity and is hard work.
• Inversion – If you’re not sure what to do about a problem, think it through backward to figure out what not to do. By knowing what not to do, you’re one step closer to understanding what to do.
• Outsourcing thinking – You can’t outsource your thinking. You must think for yourself and, ideally, in a multidisciplinary manner.

Those are just some of my takeaways from this book. I’m glad I read it and will likely reread it someday.