Reviewing my notes on The Outsiders: Eight Unconventional CEOs and Their Radically Rational Blueprint for Success, I spotted a few patterns. Most of the CEOs displayed the following traits:

• Daily operations – These CEOs hired strong lieutenants who managed day-to-day operations. This time-management hack allowed them to focus on whatever the most pressing issue was at any given time and strategic things like capital allocation. Finding the right number two took years in some cases, but when it happened, it freed these CEOs from the weeds of the business and gave them more control of their time.  
• Frugal – There’s an old saying: “If you watch the pennies, the dollars will take care of themselves.” All these CEOs took this to heart and watched their costs. They were happy to spend, but only when the return was clear. They avoided unnecessary layers of people and the associated costs. Most avoided expensive class A offices, opting for modest, unassuming offices instead. Tom Murphy of Capital Cities Broadcasting used frugality as a defense to his company’s inconsistent ad revenue. He recognized that he couldn’t control revenue but he could control his costs.
• Independent thinking – These CEOs didn’t believe in mimicking others. They didn’t follow their peers or conventional thinking. Instead, they spent time doing their own thinking to arrive at rational and pragmatic decisions. These decisions were often the opposite of what peers were doing and led to returns that exceeded those of their peers.
• Free cash flow – Free cash flow is a recurring focus among these CEOs. They didn’t pay attention to reported profits (i.e., net income); rather, they wanted to know how much cash the business generated that they could allocate. The distinction between free cash flow and net income is an important one. Many entrepreneurs don’t understand that difference, and it shows in their decision-making.

These CEOs ran large public companies, but these are traits that founders of almost any stage company can embrace and benefit from.

Today I finished reading The Outsiders: Eight Unconventional CEOs and Their Radically Rational Blueprint for Success. William N. Thorndike, Jr. profiled these CEOs:

• Tom Murphy, Capital Cities Broadcasting
• Henry Singleton, Teledyne
• Bill Anders, General Dynamics
• John Malone, TCI
• Katharine Graham, The Washington Post
• Bill Stiritz, Ralston Purina
• Dick Smith, General Cinema
• Warren Buffett, Berkshire Hathaway

The book describes how CEOs generated capital and executed creative approaches to capital allocation, and it reports their returns over a long period. I was familiar with Buffett but less so with the others. I took many notes on Murphy, Singleton, Malone, and Graham.

It was interesting to learn about Singleton’s strategy. It was the same as Buffett’s playbook, and Singleton was older than Buffett and deployed his strategies before Buffett did. Buffett has praised Singleton as one of the best businessmen ever, and I’d imagine many strategies that make Berkshire Hathaway successful were borrowed from Singleton’s playbook.

John Malone is the CEO I’m most unfamiliar with and most excited to learn more about. Malone recognized the predictability and high growth rate of the cable industry early. He used various strategies to build one of the largest cable distribution companies. He also helped seed various cable programming entrepreneurs, such as Bob Johnson of BET, and partnered with other cable entrepreneurs, including Ted Turner.

This book chronicles CEOs of publicly traded companies, so most examples don’t apply to early-stage entrepreneurs. But it does a good job of explaining capital allocation, including why it’s the most important job of a CEO, and quantifying the results of superior capital allocation by talented CEOs.

Capital allocation is a mindset and a skill all entrepreneurs should be aware of. For entrepreneurs seeking to grow their companies, capital allocation is a critical skill to master.

I started reading The Outsiders: Eight Unconventional CEOs and Their Radically Rational Blueprint for Success this weekend. The book, written by William N. Thorndike, Jr., and published in 2012, details eight CEOs' methods and why they led to outsize returns for their shareholders over a long period.

The central concept of this book is that capital allocation is the CEO’s most important job. Capital allocation is “the process of deciding how to deploy the firm’s resources to earn the best possible return for shareholders.” It’s investing to get the highest return, so CEOs are both capital allocators and investors.

CEOs need capital before they can deploy it. They can acquire capital in three ways:

• Generating cash from company operations
• Issuing debt (i.e., bank loans or bonds)
• Selling equity (i.e., selling part of the company to VC, PE, or public investors)

When CEOs have capital, they can deploy it in several ways:

• Investing in the company’s existing operations
• Acquiring other businesses
• Issuing dividends
• Paying down debt
• Repurchasing equity (i.e., buying back part of the company)
• Launching new businesses (as the sole owner or in partnership with others)

These options make up a CEO's capital allocation toolkit. Figuring out what tools to use, if any, and when, is the skill of capital allocation. The book emphasizes that no courses are taught on capital allocation (as of 2012), so it’s a skill many CEOs lack. Now, though, Columbia Business School apparently covers this topic in its Security Analysis course.

Core to gauging the effectiveness of a CEO’s capital allocation in the long run “is the increase in per share value, not overall growth or size.” Long-term per share value essentially measures long-term value creation.

When I ran my company, I was focused on two things: running the company efficiently and generating cash. Getting the operations right consumed much of my time, and I didn’t think in terms of being a capital allocator.

So far, the stories of how these CEOs thought about and executed capital allocation strategies to generate high returns have been thought provoking. I’m looking forward to finishing this book.

I finished reading The Davis Dynasty: Fifty Years of Successful Investing on Wall Street this week. The book chronicles three generations of the Davis family and how an initial $50,000 investment in stocks by the patriarch has turned into more than $2 billion for the family and an investment firm that manages over $25 billion in total assets.

This book caught my eye because I enjoy learning about “investor entrepreneurs” —investors by profession who don’t want to work for someone else, so they choose to become entrepreneurs by starting companies that invest capital

In the 1940s, the Davis family patriarch had a unique insight about insurance companies. He realized that (1) the companies had hidden investment portfolios that would compound for long periods until claims were paid out, but they were disguised as unprofitable companies because of accounting rules, and (2) the market for life insurance was exploding because of World War II. He quit his job in 1947 and became a full-time investor specializing in the stocks of insurance companies. His timing proved ideal: his portfolio ballooned from $50,000 to roughly $10 million by 1959.

One key takeaway from this book is the patriarch’s insistence on writing and distributing a weekly bulletin about the insurance industry. In the early 1990s, his grandson began helping him write this newsletter. He asked why they should bother when the lack of feedback suggested that no one was reading it. The patriarch’s response? “It’s not for the readers. It’s for us. We write it for ourselves. Putting ideas on paper forces you to think things through.”

The patriarch used the weekly bulletin as a tool for reflection and learning. Distributing it to others added accountability to the process.

When I read this, I thought about a few successful founder friends with a similar habit—which I remembered because it’s rare. They’ve built companies worth hundreds of millions of dollars or more. Each sends a weekly email update to their investors and/or team. They’ve kept up with this habit for years, since their earliest days. I asked one of them why he keeps doing it. He does it for himself, he said, not the recipients. It forces him to reflect on the past seven days and plan for the next seven.

I’m a proponent of founders sending update emails. It’s a habit with superpower potential. Everyone can do it, and because few people do, it gives those who take the time for it an edge.

Last week I shared my takeaways from reading Built from Scratch: How a Couple of Regular Guys Grew The Home Depot from Nothing to $30 Billion, a book about Home Depot’s founding. One thing I learned is that Home Depot’s founders rethought their market, which changed their growth strategy.

They initially went after the do-it-yourself market, which was consumer focused. Then they realized they were serving the home-improvement market. This change in how they thought about and defined their market was important because home improvement included contractors too. Home improvement was a much bigger and more fragmented market than do-it-yourself. This decision played a role in Home Depot’s annual revenue increasing from $20 billion in 1996 to $135 billion in 2023.

Today it was announced that Home Depot is acquiring SRS Distribution Inc., a “distributor of building products . . . serving the professional roofing contractor’s business.” The deal is for about $18.25 billion. The stated logic behind the deal is that it will help Home Depot grow its business with contractors.

The Home Depot’s founders haven’t run the company for over twenty years. But their insight about what their market is and what customers they serve is still driving the growth strategy today, even if it’s growth through acquisition rather than organic growth.

Markets matter a lot more than some entrepreneurs realize. I’d say it’s one of the most important factors that impact business success and growth potential. Building a big business in a small market is hard because there aren’t enough people willing to buy your product or solution. Home Depot’s realization about its market roughly thirty years ago has allowed it to build a massive business, and it still provides growth opportunities, as shown by today’s announcement.

I recently finished reading Bull! A History of the Boom and Bust, 1982–2004 by Maggie Mahar. The book was published in 2004, not too long after the dot-com bubble burst. I’ve seen the book recommended a few times and noticed that the cover includes an endorsement by Warren Buffett, so I ordered it. Also, the book’s narrow focus on the period when interest rates started what ended up being a forty-year decline through 2004 was intriguing to me.

I enjoyed reading the book. Given the focus on a very specific period, it provides lots of details about the economic environment, who the main figures were who had an impact on the stock market, and the key decisions they made. Mahar does a good job of describing her perspective on the impact those decisions had on inflating and bursting the internet bubble.

One thing that caught my attention was her explanation of the role the inclusion of high-flying technology companies in stock market indexes (e.g., the S&P 500 and NASDAQ Composite) played in valuations reaching levels that were hard to justify. She believes that this, combined with the rise of the 401k and index funds, contributed to a significant amount of capital being allocated to these highfliers even though valuations were hard to justify. The valuations of companies kept rising because capital kept flowing into the index funds until the stock market bubble burst around 2000.

This caught my attention because last month, I listened to an interview of David Einhorn, founder of Greenlight Capital. Einhorn shared his opinion of the impact that passive investing is having on the valuations of certain companies in today’s stock market. Essentially, he believes that valuations of companies continue to rise because they’re part of one or more stock market indexes (e.g., the S&P 500 and NASDAQ Composite). Passive index funds track indexes, which leads to the funds buying more shares in these companies, regardless of the valuation, as more investors allocate capital to the passive index funds. For this section of Einhorn’s interview, listen here.

I found this interesting because there’s a twenty-year gap between this book’s publication date and Einhorn’s interview.

This weekend, I was chatting with a friend about public markets and IPOs. Neither of us knew how IPOs are trending this year, so I decided to check the stats. Here’s what I found:

2024 IPOs

• January: 15
• February: 16
• First two months total: 31

For comparison, here are the stats for the same months for the last five years:

2023 IPOs

• January: 8
• February: 17
• First two months total: 25
• Full-year total: 154

2022 IPOs

• January: 34
• February: 32
• First two months total: 66
• Full-year total: 181

2021 IPOs

• January: 118
• February: 132
• First two months total: 250
• Full-year total: 1,035

2020 IPOs

• January: 12
• February: 20
• First two months total: 32
• Full-year total: 480

2019 IPOs

• January: 6
• February: 21
• First two months total: 27
• Full-year total: 232

The number of IPOs completed in the first two months of this year has increased compared to the same months in 2023 (which was an anemic year). But we’re well below the number of IPOs we saw in 2021 (which was a record year).

Interestingly, the stock market reached an all-time high this past week. The NASDAQ Composite Index reached a record high close of 16,274 this past week. Its previous high was 16,057 over two years ago in November 2021.

I’m curious to see how IPO activity plays out for the rest of this year, especially if the NASDAQ Composite Index stays above the records set in 2021.

Yesterday I shared a key concept I took away from reading Home Depot cofounder Ken Langone’s book I Love Capitalism!: An American Story. Today I read a section where Langone shared the details of how he orchestrated Home Depot’s successful IPO in 1981. It was a tough environment in which to raise money from public-market investors. The economy was in a recession, inflation was through the roof, and interest rates were surging. But Home Depot was just a start-up and needed cash.

One week before the IPO date, bankers said they could fill only $3 million of the target $6 million the company needed to raise. Langone got to work and figured out a way to craft a creative deal and sell it to the existing investors (who ended up not being able to sell shares in the IPO). Everyone agreed to the new terms, and the company raised the $6 million it badly needed.

Langone’s reflection on this difficult situation stuck with me:

If there’s anything I would take a bow for throughout this whole process, it would be this: never giving up, and thinking creatively, instead of reactively, when the chips are down . . . . You get to enjoy lemonade instead of the lemons God gives you . . . .

Langone was in a tough spot. Home Depot cofounders, employees, and existing investors were all counting on him to remove the IPO roadblocks before the deadline. He was in a high-pressure situation, and he kept pushing. He focused on figuring out how to accomplish the goal given the hand they’d been dealt. His solution was unorthodox but ended up working. Absent Langone’s persistence and resourcefulness, Home Depot might not have gone public in 1981 or, worse, survived.

A few weeks ago, a friend suggested that I learn about the founding of Home Depot, since I’m in Atlanta. I did, and one of the cofounders wasn’t what I expected. His name is Ken Langone. He’s a colorful character from humble beginnings, a hybrid between entrepreneur, venture capitalist, and investment banker. I watched a few YouTube videos of him and got more interested in his story.

I discovered that Langone wrote a book called I Love Capitalism!: An American Story. It’s about his life and adventures in business. I bought it as soon as I found it and started reading. I’m not finished yet, but so far I’m enjoying it.

One concept that Langone shares in the book is over-delivering to cement relationships. Langone was the banker who IPO’d Ross Perot’s company, Electric Data Systems (EDS), in 1968. Langone had never taken a company public before and had a lot riding on the EDS IPO being successful. He thought highly of Perot. He wanted this transaction to be a success, and he also wanted to build a long-term relationship with Perot. Because of EDS’s uniqueness and growth potential, he was sure the public markets would be receptive to the IPO. He told Perot he could take EDS public at 100 times earnings (a number far higher than other bankers thought possible), or $15 per share.

The IPO was a success, and Langone was able to deliver Perot 115 times earnings, or $16.50 per share. Perot was ecstatic. He publicly praised Langone whenever the opportunity arose. Perot’s praise and the publicity about the EDS IPO got Langone a flood of new business. It also cemented his relationship with Perot because he far exceeded Perot’s lofty expectations.

Langone watched others over-promise and under-deliver. They’d close a transaction but ruin relationships because they’d lost people’s trust. Langone didn’t want to ruin relationships, so he took a different approach. To build a relationship and trust, he set what he thought were reasonable expectations and worked doggedly to over-deliver.

Fun fact: Because of Perot’s relationship with Langone, Perot was one of the first people who got the chance to invest in Home Depot when it was an early-stage company in 1978. Perot came close to investing $2 million and would have owned 70% of Home Depot if the transaction had been completed. As of the writing of this post, Home Depot has a market cap (i.e., valuation) of roughly $375 billion.

I’m following the rumored Reddit IPO, as it’s anticipated to be the first major technology IPO of 2024. The performance of this IPO could affect the actions of other late-stage technology companies and venture capital investors. With the NASDAQ trading just shy of all-time highs as of this writing, a well-performing IPO could unleash a wave of technology IPOs.

Last week, Reddit officially filed its Form S-1 with the SEC, indicating its intention to publicly list on the New York Stock Exchange (NYSE). Per CNBC, the company’s public market debut is expected in March (but that isn’t confirmed and is subject to change).

I’m curious to learn more about Reddit’s business and follow its post-IPO performance (assuming it moves forward with its public offering).