I was talking to a friend who’s a big Warren Buffett and Charlie Munger fan. He shared his views on their long-standing habit of buying cash-flow-generating companies and holding them forever via Berkshire Hathaway and the Daily Journal. I’m familiar with both and with their styles of investing, but my conversation with my friend made me want to dig a little deeper.

Before Berkshire Hathaway, Buffett was investing in publicly traded companies with money from limited partners. It was 1956. He was twenty-five years old when he became an investor entrepreneur by starting Buffett Partnership, Ltd. with seven limited partners (almost all of whom were family) and raising $105,000.

Buffett is well known. He went on to have a wonderful track record as an investor. But what really intrigues me is the fact that he didn’t want to work for anyone else. Deciding to bet on himself, he started his investing partnerships. That’s strong entrepreneurial spirit combined with an investor’s mindset.

I want to learn more about his mindset in those early days and how he went about building his partnerships and investing in other companies. Buffett regularly wrote letters to his limited partners. I’ve decided to read all those letters to learn more about his early days, his entrepreneurial spirit, and, hopefully, what led to his outsize success.

I listened to Mark Leonard, founder of Constellation Software, share his thoughts. His company buys small software companies—it has acquired hundreds since it was founded in 1995. The software companies it targets are profitable and growing.

Mark spent over a decade as a venture capital investor before founding Constellation. He compared the venture model to Constellation’s model, and here’s what jumped out to me:

• Venture capital – The goal is to create companies you can sell either through an IPO or outright sale. The focus is on preparing the company to be sold to someone else, not necessarily building a business that can last a lifetime. He didn’t say this, but most funds have a ten-year life cycle—they’re liquidated at the end of the cycle and proceeds are returned to investors.
• Holding company – Holding companies like Constellation are built using permanent capital. The goal is to keep the capital invested in portfolio companies long-term. There’s a buy-to-hold mentality. This changes decision-making. You build relationships with founders and managers that will last a lifetime. You’re building a business with the intent that it will be around for decades, generating cash.

I love hearing origin stories, and Mark’s makes it clear that he wanted to build companies he could hold forever, not a decade. Given the current interest-rate environment, I wonder if we’ll start seeing more investors embrace the holding-company approach to investing in smaller technology companies.

I’m a big fan of people who share their thoughts publicly. I enjoy reading how others think about certain topics. I’m an even bigger fan of investors who do this. I recently read a memo by Howard Marks, founder of Oaktree Capital, titled “bubble.com.”

The piece is just as you would expect, given the title: Howard shared his thoughts about what he viewed as a market bubble. I’ll describe my takeaways from it in another post, but I want to highlight something else today. Reading the memo, you’d think it was written recently (if you ignore the company names he references). Howard’s insights are accurate and help explain some of the things we’ve seen in the markets over the last three years. The interesting thing is that this isn’t a recent memo. Howard wrote it over two decades ago in 1999 and released it publicly on January 2, 2000.

Howard did a great job of explaining why he viewed the market as a bubble. He clearly had great comprehension of what was happening during a frenzied period in history, and his insights appear to have stood the test of time.

Earlier this week I shared my thoughts on people being less inclined to fit their lives into their work. Here’s a little more on that. I recently spoke with a venture capital investor at a prominent West Coast fund. She shared that she’d reevaluated where she worked. She concluded that the West Coast, with no support system and her aging parents thousands of miles away, wasn’t conducive to a good life with a young family. She ended up moving back to her hometown and working remotely, with the firm’s support.

I’m glad she was able to make a move that works for her family without limiting her options professionally. It’s encouraging to hear that her firm embraces this for her and other team members. I’m curious to see how venture firms react once they realize founders are making similar evaluations. Founders are likely to want to build companies in locations that suit their personal lives rather than relocate to be closer to Sand Hill Road.

Two emerging venture capital fund managers shared their biggest learning during a session I attended today. They said there’s a difference between being a fund manager and being an investor. They spend more time than they anticipated managing their fund versus investing. Managing a fund means doing administrative tasks like working with the fund administrator, doing people related tasks, and managing limited partners. They underestimated the amount of energy and time these tasks require. These tasks also take away from the time they can spend finding great founders to back and supporting the founders they’ve already backed.

Starting your own fund is about more than being an investor. It’s more like being a start-up founder—wearing multiple hats and being spread thin. It’s also a decade-long commitment (assuming your fund is a ten-year fund). For those who haven’t worked at a fund before, it’s even harder as they don’t have a baseline for how a well-run fund operates.

Building a successful fund requires that the founding partners be good fund managers and good investors.

Today I participated in a mock negotiation session that was designed to mirror a negotiation between venture capital investors and founders. Most participants hadn’t negotiated an investment deal before, so I was curious to hear their takeaways.

One of the founders shared something that stuck with me. Their negotiation started off with aggression from the investors, which set a bad tone. And the investors were aggressive with terms throughout the negotiations. Toward the end, the investors realized they were running out of time to get a deal done and offered a better deal. The founder was so frustrated by the experience that she didn’t even realize they had offered better terms and walked out without a deal. She was stuck on the aggressiveness of the entire process and couldn’t bring herself to do a deal with these investors.

Venture investors and founders, when they come to an agreement, are planning to work together for many years. But at deal term negotiations, they have opposing interests. Today’s session was a reminder that starting off with aggressive negotiating tactics isn’t a way to begin a long-term partnership and can blow up the partnership before it even forms. The best deals are ones that everyone is comfortable with, neither side got everything they wanted, and they’re looking forward to working with each other.  

Howard Marks is a successful investor who cofounded Oaktree Capital in 1995. As of today, Oaktree has $170 billion in assets under management, over 1,000 employees, and offices worldwide.  

During a recent interview at the University of Chicago, Howard shared his interesting thoughts about a trait he believes leads to investing success: second-level thinking. He defines it as thinking deeply, differently than the herd, and better than others. Second-level thinking is about insights, he said.

I believe second-level thinking is a key to outsize success in general, not just in investing. You can’t do what everyone else is doing and achieve outsize success. Second-level thinking means taking in information and forming your own conclusions instead of easily agreeing with others. Part of that process is connecting the dots between seemingly unrelated information to produce insights others haven’t had. Those unique insights lead to conclusions and actions that differ from those of the masses. The result is outsize outcomes.

Second-level thinking is important, as it’s the intellectual process that leads to unique insights.

Today I was part of a group that chatted with Scott Kupor, Managing Partner and employee number one at Andreessen Horowitz. a16z, as the firm is known, is a well-known venture capital firm that helped start the trend of having a large operating team of specialized people support the needs of portfolio companies. As Managing Partner, Scott has helped steer the firm from $300 million in assets under management (AUM) to over $30 billion in AUM since 2009.

Scott had a lot of great things to share, but one thing especially stood out to me. He talked about the need for geographic diversity of VC investments. The Bay Area has historically been the center of the industry. This has created a challenging dynamic.

• Founders outside the Bay Area have a hard time getting funding. This means that founders working on problems experienced by broader society but not so much in the Bay Area are less likely to receive the capital needed to solve them. Said differently, some of society’s big problems go unsolved.
• Lots of people fishing in the same pond creates an interesting dynamic for return on venture capital investment. It becomes increasingly competitive as abundant capital chases scarce opportunities to invest in an exceptional founder solving a big problem. As the competition increases, the valuation increases. As the valuation increases, the potential return on the investment is reduced.

I totally agree with these points and all the other great ones that Scott made. He made a strong case for geographic diversity of venture capital investment. Hopefully Scott and the a16z team will spend more time getting to know Atlanta and its start-up ecosystem and learn for themselves why Atlanta is ranked the best place to live in the U.S.

Some founders seed their companies with their personal capital in the early days. There are a variety of ways to handle this, with a loan from the founder as a shareholder being the one I’ve seen most. When a founder plans to grow their company quickly and raise venture capital, they have another option: they can classify their capital as an investment in the company. The easiest way to do this is through a convertible note or simple agreement for future equity (SAFE).

Why would a founder want to do this? For many reasons. One is that it helps to separate sweat equity from financial equity. If a founder must leave the company for some reason and their equity as a founder doesn’t vest, they still have their financial equity. The founder will own a percentage of the company based on their investment, regardless of what happens with the equity tied to their employment.

There are other benefits too, such as owning—for the financial equity—preferred equity versus common equity.

When someone says a company is a Fortune 500 company, people know it’s a large company. But what does that mean exactly? I decided to find out. Apple is the most valuable public US company and has a market cap (i.e., valuation) of $2.42 trillion as of today, so I assumed it would be ranked first on the Fortune 500 list. To my surprise, it was third. Walmart was ranked first and Amazon second. See the complete Fortune 500 list for 2022 list here.

I looked up Fortune’s methodology and learned that it uses total revenue to determine the rankings. Not market cap (i.e., valuation) or profitability. Just top-line revenue. It ranks on how many dollars customers gave a company (revenue) in a year, not how many of those dollars the company kept (profit) or what the market says the company is worth (market cap). Here’s the top three Fortune 500 companies (with 2022 revenue for context):

• Walmart – $573 billion
• Amazon – $514 billion
• Apple – $394 billion

Conversely, the S&P 500 is an index of the largest publicly traded companies listed in the United States. The S&P 500 doesn’t rank companies directly. Instead, each company makes up a certain percentage of the overall index, which is called its index weight. The weight calculation isn’t as simple as Fortune’s revenue methodology, but it is mostly based on market cap. The larger a company’s market cap, the more weight that company carries in the index. Full weighting methodology here.

Here are the companies with the biggest index weights (with market cap as of today for context):

• Apple Inc. – $2.42 trillion
• Microsoft Corp. – $1.89 trillion
• Alphabet Inc. – $1.21 trillion
• Amazon.com Inc. – $962 billion
• Berkshire Hathaway – $684 billion
• Nvidia Corp. – $597 billion
• Tesla, Inc. – $570 billion
• Exxon Mobil Corp. – $447 billion
• UnitedHealth Group Inc. – $439 billion

Interestingly, Walmart is an S&P 500 company, but it has a lower weight in the index than the above-listed companies. It has a market cap of $372 billion as of today.

Interesting to see how Fortune and S&P 500 both seek to identify the largest companies, but their rankings differ because they’re measuring different things.

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