There’s an old saying: sometimes you can’t see the forest for the trees. I agree. As a founder, I was jumping from one detail to the next to keep the business operating. It was hard to see the bigger picture.

A few years in, I joined EO and had monthly accountability meetings with other entrepreneurs. To prepare for these meetings, I had to think through the business at a high level and make notes. I then shared my thoughts and the previous month’s metrics with my EO forum members. I engaged in this ritual every month for years, and it was transformative for my business.

The meetings forced me think about my business more broadly. I had to consider what strategic things I wanted to accomplish and what was hindering me. I got perspective from people who didn’t know the details of my business but were familiar enough with it at a high level to ask tough questions, share relevant experiences, and point out insights I was staring at but couldn’t see.

I learned from my years in EO that, as a founder, it was easy for me to live among the trees. But I couldn’t stay there all the time. To take my business to the next level, I had to get a bird’s-eye view of it. These regularly scheduled sessions with credible people I respected—whose only view of my business was from high up—were invaluable.

You’ll always have a ton of problems to solve down among the trees. But being intentional about looking at the business from a higher level on a regular cadence can be transformative. I did it with EO, but you can accomplish this in many other ways. Whatever your method, make time for it. The forest looks different from up there.

I’m making my way through Direct from Dell: Strategies That Revolutionized an Industry, Michael Dell’s autobiography. He’s the founder of Dell and, according to Forbes, worth about $115 billion as of this writing. A big part of Dell’s successful direct-sales model was understanding customer needs deeply and offering appropriate solutions.

Michael said he spent roughly 40% of his time with customers at the time this book was published, even though he was the CEO. How he did that caught my attention. “By spending time with your customers where they do business,” Michael wrote, “you can learn more than by bringing them to where you do business. You can experience the issues and challenges they encounter in their daily lives, and better understand how your product ultimately affects the ways in which they serve their customers.”

This passage gave me pause because it wasn’t the first time I’d heard this. Sam Zell was a prolific entrepreneur and real estate investor. In his book Am I Being Too Subtle? Sam shared a story about learning the value of observing people in their own environments. Because of this lesson, Sam didn’t have people meet him at his office. Instead, he spent over a thousand hours a year on his plane, traveling the world to meet people. He wanted to see them in their environments so he could learn more about them.

Sam, like Michael, was wealthy. He was worth billions when he passed in 2023. People would gladly come to see either of these guys in their office. But both insisted on leaving the office to go see people because observing someone in their home or workplace is an immense learning opportunity. The better you understand someone, the easier it is for you to add value and have a positive relationship with them.

When two credible and unrelated people say the same thing, I take note. The lesson is clear. Get out of your office and go see people—especially your customers—in their offices.

This week, I started reading Direct from Dell: Strategies That Revolutionized an Industry. It’s the autobiography of Michael Dell, founder of Dell. The company is famous for being the first to allow customers to order custom-made computers directly from a manufacturer.

I’m early in the book, but already one line has caught my attention: “The $1,000 required to capitalize a company in Texas was the extent of my initial start-up capital.” Michael incorporated the company in January 1984 while he was in college. He dropped out after he finished his freshman year, to his parents' chagrin.

So, Michael is super young and starts this company with $1,000. By the end of 1986, three years later, the company was doing $60 million in annual revenue. And Michael set a goal to do $1 billion in annual revenue by 1992 (which he exceeded).

In the first three years of Dell’s existence, it did $160 million in total revenue and raised zero outside capital. This is probably one of the craziest growth stories for a bootstrapped company I’ve ever read. Growing fast is expensive. You have to put people, systems, and processes in place ahead of that kind of growth. It’s very rare to grow that fast and not raise outside capital.

This is where the genius of Michael’s model shines. A lot of this can be attributed to how Dell sold computers then. It didn’t make computers ahead of time and ship from inventory. Customers paid up front, and then Dell built and shipped the computers. Getting paid up front was a stroke of genius. It allowed Dell to obtain growth capital from customer revenue instead of having to raise money from outside investors. Now, Dell did have to buy parts and other stuff to assemble the computers, but it did so as close to just in time as possible, minimizing the amount of money tied up in raw materials inventory.

In October 1987, Dell completed a private placement on Black Monday and raised $20 million, even though the stock market was crashing. The following summer, Dell went public. The company merged with EMC Corporation in 2016, so it has changed a bit. But that combined company has a market capitalization (valuation) of over $78 billion as of this writing and over 120,000 employees. And Michael Dell is still CEO, more than 40 years later.

I was impressed when I read the details of Dell’s early growth and how Michael did it. His story is a reminder that customer revenue is always the best source of growth capital, especially if you can get customers to pay up front.

I’m rereading Junk to Gold: From Salvage to the World’s Largest Online Auto Auction. It’s the autobiography of Copart founder Willis Johnson. Johnson is worth roughly $3 billion today, most of which is his stake in Copart. I listened to an interview he gave recently, and it made me want to read his book again. He founded Copart in 1982 as a salvage yard. He purchased wrecked cars and sold the parts and scrap metal for a profit. The company has expanded. It’s now a global online auction market for used and repairable vehicles. As of this writing, it has a market capitalization (i.e., valuation) of over $56 billion.

In his book, Johnson describes himself as rough around the edges. He isn’t polished and doesn’t always use the “right” words. He attended community college for one semester on the GI Bill and then dropped out. So, how did Copart become a massive company?

As I shared last year when I read the book, Johnson didn’t have a big vision for the company. He didn’t even have a plan. But he knew he wanted to grow. The key to Johnson’s success was his ability to master two things.

He was a cloner. He paid close attention to what was happening around him and what others had done. If he liked an idea and thought he could make money with it, he tried it out. He learned about a new model involving people pulling parts off cars themselves called “Pick-A-Part.” He studied it closely and copied it by creating “U-Pull-It.” The idea was a massive success. When he heard a competitor was raising capital to expand rapidly by doing an IPO, he paid attention. Two years later, Johnson’s company was trading on the stock market too.

Johnson also was an astute student and avid reader. He believed he could teach himself anything. For example, to figure out how to do an IPO, he started by trying to get a basic understanding of IPOs. He read the IPO prospectus of his competitor many times to understand what the IPO involved and to understand the Wall Street terminology. He then went to his local library to find books that explained the IPO process and all the terminology in more detail. He had trouble finding a book because nothing came up when he searched for “IPO.” He went to three different library branches. It wasn’t until someone at the third library branch told him that “IPO” stands for “initial public offering” that he found a helpful book from Ernst & Young, which he studied extensively.

Being an avid learner and reader is a great way for entrepreneurs to get ideas and strategies to grow their businesses. Some of the most successful entrepreneurs and investors didn’t invent new ideas or strategies; they copied other people’s great ideas. For example, Warren Buffett got the idea to have an insurance company (and maybe decentralization too) as part of Berkshire Hathaway from Henry Singleton and Teledyne. Henry Singleton got the idea by reading the book My Years at General Motors by former General Motors chairman Alfred Sloan.

The beauty of both of these—copying others’ good ideas and self-learning—is that anyone can do them. They don’t require permission or consent from anyone else. Not sure what to do to solve a problem? Not sure how to grow your business? No problem; start reading biographies of credible entrepreneurs. Learning about their journeys to build their companies is bound to give you some ideas about how to grow yours.

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.