Today, I listened to an interview of Matt Mullenweg, founder of WordPress and Automattic. WordPress is an open-source content management system for websites. The platform helps you manage what your website shows. WordPress is extremely popular, powering roughly 43% of all websites (hundreds of millions of them) on the internet. Automattic is a holding company that owns several internet businesses, including WordPress. It did over $500 million in revenue in 2024.

Matt started WordPress when he was 19. One thing in the interview got my attention. WordPress is a platform that people can build businesses on. To develop his platform strategy, Matt didn’t try to reinvent the wheel. Instead, he studied another platform company—and not just any platform company, but the most successful one: Microsoft. He read about Microsoft and realized that the Windows operating system had Microsoft Office (Word, Excel, PowerPoint, etc.). For Microsoft, building its own application on top of its platform was a key strategy that turbocharged its financial performance.

Learning about Microsoft’s strategy led Matt to ponder what the WordPress equivalent of Microsoft Office would be. What application could he own that sat on top of the WordPress platform? Matt leaned into the strategy but didn’t build an application. He bought one. He ended up purchasing WooCommerce, an e-commerce plugin for WordPress. It allows people to turn a WordPress website into an e-commerce site where people can complete purchase transactions.

WooCommerce, according to Matt, has been one of his best acquisitions. Last year, $30 billion worth of transactions occurred on WooCommerce.

Matt’s a pretty sharp dude. Even so, he got his inspiration from reading about the history of another successful company. He copied its strategy (clearly, it worked, since his product is running a little less than half the internet) and modified it for his situation. He didn’t waste time trying to figure out what would work; he focused on modifying and executing a wildly successful strategy.

This resonated with me because I’ve had a comparable experience. This past summer I read about Michael Bloomberg’s strategy in a biography. After that, everything clicked, and I knew what my strategy was for my book project. I’ve been executing on it  since.

My takeaway from Matt’s interview and my experience is that there’s immense value in the biographies of founders and histories of companies. If you’re unsure about what strategy to take to grow your company, reading biographies and learning about other entrepreneurs’ strategies and why they worked is a good use of time. You might just read one that clicks and changes your business or idea, too.

If you want to see this strategy section of Matt’s interview, it’s here. If you want to watch the entire interview, which is good, see here.

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 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.

Today, I had a good chat with a founder friend. He mentioned an idea that I thought about for the rest of the day. Sometimes, early-stage founders struggle to reach their next milestones. They know what they want to do to get there, but they don’t have the necessary skills. Their weaknesses hold them back, and they can’t afford people with high-level expertise. However, they often know tons of other founders—and some are strong where they are weak. And vice versa.

My friend’s observation was that early founders, especially those who are bootstrapping, may be able to complement each other temporarily. For example, Bob struggles with marketing but is strong in engineering. John is a killer marketer, but nontechnical. Instead of complaining to each other about not being able to afford or find high-level talent to get them to the next milestone, maybe the two entrepreneurs should temporarily partner with each other. Bob helps John with his technical problems. John helps Bob market his software. Again, temporarily.

My friend took this even further and suggested that these two founders not accept cash compensation. Instead, they pay each other with a very small amount of equity ownership in their respective companies. This aligns interests, helps both companies be capital efficient, and allows each to get high-level talent it otherwise couldn’t access (or afford). Again temporarily. Of course, vesting and other things would need to be clearly outlined.

My friend’s thesis was that certain high-level expertise can make a big difference in the early days. It can help you reach those critical milestones, but it isn’t a full-time job. It’s more of a gap that needs to be filled until you have sufficient traction and resources to hire someone full-time. Also, discussing strategy with another founder who has expertise in a critical area makes those strategy conversations richer and results in better ideas and solutions. Lastly, no one goes as hard as founders. Having a founder on your side, even part-time, can be a game changer.

Today, I chatted with a friend who’s building a new software company. He shared his milestones with me, and I asked how he came up with them. His answer was simple. There’s a major industry conference in March. He wants to do a big launch at that conference, so that’s the date of his public launch. He needs to test it beforehand, so he’s doing a beta launch in the first week of February to select users. He shipped an early version of the product last week to get something out the door so he can iterate before the beta launch.

His approach makes a lot of sense. Pick an event where you want to make the product available to everyone, and then work backward. Create milestones so you can take advantage of feedback cycles and improve the product.

I like his strategy because choosing a public launch day that’s aligned with an event means the launch date can’t change. There’s no pushing it back. You either hit the date or you miss a big opportunity. This adds urgency, and setting mini milestones a few months ahead creates accountability. You can’t wait until the last minute to prepare for the public launch. It also allows you to get and incorporate feedback from early users and adjust the product before the general public sees it.

Over the past two years, I’ve studied countless investors who’ve had outsize success. One firm I studied was Altos Ventures. It popped up on my radar when I read the S-1 for Roblox and learned the firm had an almost 25% ownership stake when the company IPOed at a $35.5 billion valuation (see my post here). Altos’s stake was worth over $8 billion at IPO, an enormous haul for a single firm. (The Altos ownership stake can be seen on page 172 of the S-1, here. The ownership is under the name of Altos partner Anthony P. Lee, who serves on the Roblox board.)

Today, an interview of Ho Nam, an Altos founding partner, was published. I’ve watched several Ho interviews; this one was deeply personal and highlighted his struggles while building Altos. Ho described how Altos struggled for over fifteen years. The firm raised four funds and hadn’t generated meaningful returns. The partners hadn’t made any money and weren’t seeing eye to eye.

Their struggles led Altos’s three partners to change their strategy. They originally played what Ho calls the VC lotto game. They’d find promising companies early and focus on preparing them to raise the next funding round from a brand-name VC firm at a higher valuation. That strategy imploded when the dot.com bubble burst. The Altos partners realized they were playing a game they weren’t suited to win. They changed their strategy to focus on helping founders build enduring cash flow–positive businesses that didn’t require excessive venture capital funding. They focused on helping the founders create value for customers in a capital-efficient manner, not on hyping them up to later-stage VC firms.

This strategy change worked in a major way for Ho and Altos. The firm has since had several early-stage companies that each has gone on to be worth over $1 billion; a few, over $10 billion. The firm still owns a stake in Roblox, although it’s been distributing shares to LPs since the IPO, likely for liquidity reasons. As of this writing, Roblox has a market cap (valuation) of almost $42 billion. Coupang is another company Altos invested in early, and that company is publicly traded with a market cap of over $40 billion as of this writing.

Here are a few of my takeaways from Ho’s interview:

• Everyone can’t play every game. Figure out what game you can play and win. Play that game, even if it’s not popular at the time. Winning fixes everything, and you’ll look like a genius in the end.
• Struggle is often a prerequisite to outsize success. The painful times force you to evaluate why things aren’t working, hopefully leading to changed behavior. The wisdom gained during struggle leads to better decision-making, which is required for outsize success.
• Companies exist to add value to customers. You add value to customers by solving their problems. Focus on solving the customer’s problem and capital to grow your company is less likely to be an issue.
• The best founders are capital efficient. Constraints force creativity, which leads to better solutions for customers. Raising too much money leads to loose spending, which leads to founders focusing on raising capital from investors, not solving their customers’ problems.
• Control matters a lot for founders. If you’re constantly raising rounds of capital, you're losing control, and your board could fire you.

I enjoyed this interview, which contains nuggets of wisdom for founders and investors to learn from. If you want to watch this section of the interview, you can find it here. You can watch the entire interview here.

Note: Roblox is probably one of Altos’s most capital-efficient portfolio companies. Ho shared on X (formerly Twitter) that Roblox raised only roughly $10 million in funding to get to cash flow positive. All other capital raised was for secondaries (to buy shares from other investors) or to put on the company’s balance sheet.

The book The Money Masters: Nine Great Investors: Their Winning Strategies and How You Can Apply Them by John Train introduced me to Thomas Rowe Price Jr. (aka T. Rowe Price). I’m familiar with the investment firm bearing his name but not the man himself. I wanted to learn more, so I’m reading T. Rowe Price: The Man, the Company, and the Investment Philosophy by Cornelius Bond.

The book says that Price was one of the first investors to recognize the value of growth investing and adopt it as a strategy. After the Depression began, many people focused on preserving capital, so bonds were popular. In 1934, he recognized that the largest fortunes in the country had been created by owning growing businesses. He developed an investment strategy based on this insight and pitched the investment firm he was working for to test the approach.

With the country still feeling the Great Depression, the firm turned him down. Frustrated and having conviction about his approach, Price quit in 1937 to launch his investment firm, which would become T. Rowe Price Group.

After reading several biographies about famous investors, I’ve noticed that they all came to similar realizations about their investment approaches: investing in growing businesses is the key to outsize returns (Price’s biography details why this works so well). However, how these investors executed their strategies and built their firms varies drastically. Price built a firm that made decisions by committee and was paid by fees from customer accounts. Buffett created a decentralized conglomerate (after he shuttered his investment partnership) and increased his wealth through equity ownership in the conglomerate.

There’s more than one way to capitalize on an insight, as the stories of these investors prove. The most important thing is doing so in a way that aligns with the beliefs of the founder of the investment firm (or the investor, if they’re independent).

I’ve been struggling to articulate the problem I’m solving with my “book library” project. It’s critical to clearly state the problem in such a way that people will understand why it’s worth solving. When you can do that, people are more engaged and want to hear about your solution. But I wasn’t doing it, so I had to fight to keep people’s attention. And this was when I was talking to friends, not strangers, and I wasn’t asking them to use or pay for the solution.

I decided to use the holiday to review all my notes and start crystallizing the problem in a clear sentence. Creating a problem statement is something that sounds simple, but it’s been hard for me in the past. Getting to a concise statement is usually a process of refinement and wordsmithing. In the past, I’ve done it alone (with no success) or with a group of entrepreneurs as part of a retreat.

I didn’t want to do it alone and had no planned retreats, so I decided to use Google Gemini and ChatGPT as thinking tools. Both offer mobile apps that allow you to speak your thoughts instead of typing them. For this kind of ideation exercise, I wanted to capture my thoughts as they were flowing, so speaking was key.

I chose to use two models because no model is perfect. They all have strengths and weaknesses. But I’ve found that feeding my thoughts to both, reviewing their outputs, incorporating the outputs into my thinking, feeding my updated thoughts to both, and repeating that loop has worked well. I also ask each model to rate and give feedback on the output from the competing model. Together, this created a rapid iteration cycle, something I can’t normally do alone.

After many cycles, I’ve finally landed on two versions of what I think is a clear problem statement. I feel pretty good about both, but I’ll get feedback before I make final decisions.

Clearly articulating the problem sounds like an obvious thing that all entrepreneurs do, but many don’t have clear problem statements, which causes lots of issues down the road.

A few days ago, I shared that a founder friend suggested that I start my book library project with the end in mind—that is, with the desired output. The idea was that since I’m building a solution to a problem I’m experiencing, I’m in a position to produce hypothetical examples of the kind of output this solution could create that would solve the problem.

I've created three hypothetical outputs over the last few days. I wasn’t sure how to approach this at first, but I decided to base it on my journey with this project so it’s somewhat grounded in reality. I started with problems I’ve solved for myself during this journey or am actively trying to solve. For two examples, using problems I solved the old-fashioned way with the help of my notes and highlights from various biographies, I figured out the ideal outputs that would have gotten me to the same results more efficiently.

This was a fun exercise. Having already solved the problems, figuring out how this solution could have helped me get there more efficiently was interesting. What kind of information should it have provided to me? What kind of questions should it have asked me to get me thinking? What stories needed to be shared for suggestions to resonate with me?

I shared these outputs with my developer friend today. Having them to work backward from led to a productive discussion. We narrowed our focus to what must be built to make those outputs a reality. We realized that a structured approach to solving certain problems is required for consistent results. This reinforced the importance of data structure.

This exercise has been helpful and something I want to do going forward when I’m trying to build a solution to my own problem. I’ve got three example outputs that are complete now, and I’ve got another two or three that I want to document before the end of the year.

This past weekend, my developer friend and I chatted with a founder friend about the book library project. This founder has a unique perspective because he’s a self-taught developer, a trained designer, and a self-taught user experience (UX) person. He can take a product from idea to launch by himself—and has done so successfully by scaling and selling a software company—so he has credibility.

I wasn’t sure how the user experience should flow, so I wanted his input. The conversation was helpful, and he made a key suggestion: since the solution is being built to solve a problem that I’m experiencing firsthand, I could start with the output I’d be happy to see as a user instead of starting with the user experience. That is, I could create hypothetical examples of what kind of output I’d want this solution to create that would be tremendously valuable to me.

His point was that we could work backward to determine what the UX would need to create the output. But also, looking at this way would inform what would technically need to be built to create that output. My developer friend and I agreed that’d be a great exercise, so I’ve been working on it.

Doing this analysis has been a great exercise. It’s forced me to think about how the tool will improve my current workflow and, hopefully, that of other users. With so much information in so many books, whittling it down to the key pieces of valuable information in response to a specific question was thought-provoking. Thinking about how information and the connections between it (ideas, people, books, etc.) should be presented and how to do this without drowning myself in information was eye-opening.

I’ve completed one of these, and I’ll do a few more. A big takeaway is that the connections between information in various books make the library unique and valuable. Connections can uncover new insights. New insights help entrepreneurs develop unique solutions to problems or identify the unconventional next action to take given their goals. Today, the people who are able to take advantage of this process are mainly those gifted with a photographic memory, which isn’t me (more thoughts on that here). Showing these connections can’t be done using only text. A visual component allowing people to easily see the connections from a high level and decide where to double-click is necessary.

I’m a big proponent of starting with the end in mind and working backward, but I didn’t do a great job of doing that with this project. My friend pointed out that since I’m experiencing the problem myself, I’m too close—it’s hard to see past the details and stay focused on the big picture. He’s right. His suggested exercise is forcing me to articulate what will add value and how it looks. This will help my developer friend and me reprioritize the features and also highlight shortcomings in what we’ve already built and plan to build.

Sometimes, bringing in a fresh pair of eyes to look at things from 50,000 feet can be helpful. I’m glad my friend made the time to chat and share his candid feedback.