This is my one-hundred-ninetieth weekly reflection. Here are my takeaways from this week:

• Brainstorming – This week I spent time brainstorming with a fellow investor. We ended up landing on an interesting idea we’re both excited about digging into more. Neither of us entered the conversation with the idea. This was a reminder of the power of brainstorming with high-caliber people. I need to do it more regularly.  
• Public markets – I’ve been spending more time looking at companies in the public markets. This exercise has me thinking about early-stage investing a bit differently.
• Randomness – The world is full of randomness. Things that have a low probability of happening nevertheless happen sometimes when you least expect them. This week was a reminder of how randomness sometimes produces unexpected surprises or unexpected disappointment (or even pain).
• Fundraising – Next week is Thanksgiving. If founders haven’t received a term sheet by next week, their likelihood of completing a fundraise before year end will have decreased materially.

Week one hundred ninety was another week of learning. Looking forward to next week!

A friend called me today to say he’d been offered a complimentary, all-access pass to this weekend’s Formula 1 race in Las Vegas. He was on the fence at first but decided to accept the offer because it’s a once-in-a-lifetime opportunity. He pulled the trigger and made travel arrangements.

Once-in-a-lifetime opportunities don’t come my way often (of course), but when one does, I try to quantify the magnitude of the opportunity and then act quickly to capitalize on it if it’s truly great and rare. I’ve found that truly rare opportunities don’t last long. If you don’t take advantage of one, someone else will—with lightning speed.

A few months back, I purchased a book that was recommended by several investors who’ve had outsize success over a long period of time. I typically buy a book only if credible people recommend it and the Amazon reviews are 4.5 stars are higher. This book fit both criteria, so I quickly ordered it.

When I received the book, I realized two things. It’s 800 pages long, and it was first published almost a century ago. Both facts made me cringe. I generally read books of 300 pages or less. In my experience, the longer the book, the more fluff it contains. I enjoy books that get their points across succinctly. With verbose books, my attention wanders. I also personally don’t enjoy books written long ago because the writing style is so different. It can be a struggle for me to grasp the authors’ points because I’m not used to that way of writing. I put the book on the shelf to read later. That was months ago, and I haven’t touched it.

This book is so well regarded that I don’t want to keep putting it off or, worse, never read it. Today I set a goal: read this book by the end of the Thanksgiving weekend. That means I need to read all 800 pages by November 26. Setting this challenge for myself reenergized me in relation to this book. I can’t wait to hit this goal and learn the insights in it.

I’m a believer in non-consensus investing—that is, taking advantage of investment opportunities that don’t fit into the conventional framework used by other investors. A leap of faith is sometimes necessary. I like these investments because they require independent thinking and going against the grain, two things I embrace. To get to conviction on these opportunities, I usually do a deep dive into them, so I understand them well.

After I’ve made one of these investments, I sometimes share my thinking with other investors who are using more conventional frameworks. Recently, an investor agreed with my analysis but still didn’t think my investment was a good one because this kind of investment hasn’t historically produced significant returns.

I respect his opinion—after all, I asked for it—but I disagree. Someone must be the first to do something. The person who makes a non-consensus investment first or early is usually going to reap an outsize return, assuming it works out. When other investors follow, their returns are likely to revert to the mean because of the increase in capital chasing the opportunity. I’d rather be in the former group. I like investing in things others might not. It’s more mentally stimulating, has more upside potential, and is a better fit with my personality and wiring.

Today it was reported that Google has a revenue-sharing agreement with Apple that pays the iPhone maker a staggering 36% of the revenue that Google earns from search ads on Apple’s Safari browser. The two companies have had a partnership since 2002 that makes Google search the default search engine on Safari. These details were revealed in testimony in an antitrust lawsuit.

I don’t know how much revenue Apple receives under this agreement, but I’d imagine it’s in the billion if not tens of billions of dollars annually, given the global popularity of iPhone and other Apple devices.

Apple’s successful hardware business has another benefit for Apple. These devices are highly effective modes for distributing software and other digital tools, and companies wanting to distribute digital offerings to consumers will pay Apple to do it for them. Apple’s App Store and the revenue-sharing agreement with Google demonstrate that Apple is aware of its distribution power and plans to continue to monetize these capabilities.

I had a conversation this past week with an entrepreneur who’s run a successful business for several years. During our conversation, I realized he didn’t know the cash flow of his business—or what that means. After more chatting, I realized that he didn’t understand his balance sheet either. He didn’t know how much he owed others or how much he’s owed. He mainly bases his decisions on his bank account balance and profit and loss statement. This approach to decision-making has hindered the business’s growth over the years.

In college, I was forced to take accounting classes as part of my finance curriculum. I’m not much of a rule follower and hated memorizing countless accounting rules. Many years later, I can’t remember any of those rules to save my life. But the concepts stuck with me. How to read core financial statements and how the statements work together to show you a complete picture of the business are the biggest takeaways from those courses. When I was an entrepreneur, those foundational concepts improved my decision-making. Now that I’m an investor, they’ve helped me spot opportunities and problems early that others have missed. I hated my accounting courses and don’t remember most of what they covered, but they taught me how to understand accounting. 

Accounting is often called the language of business. To thrive in business, entrepreneurs need to speak the language—or at least understand the foundational concepts underpinning accounting. If you’re an entrepreneur or aspiring to be one, consider taking time to learn basic accounting concepts. It may be difficult, but it will likely pay off in the long run.

Early in 2023, I challenged myself to read more SEC filings of publicly traded technology companies. I’ve been reading S-1 initial registration reports for companies preparing to go public for several years. This year I’ve incorporated 10Q quarterly reports and 10K annual reports into my reading. I wasn’t sure when I began whether it would be worth the time and energy, but I figured I had more to gain than lose by trying it. 

Here are my takeaways:

• Financials – The company’s financial performance is laid bare in these reports. The good, the bad, and the ugly are there for everyone to see. Some company financials are complex; others, simple. Interpreting what the numbers mean sometimes requires work. It isn’t always fun, but once I figure it out, I’ve usually learned something useful.
• Business model – Companies detail their inner workings and how they generate revenue. They share all kinds of interesting tidbits, such as plans for future revenue sources and concerns about the stickiness of current revenue. I usually got lots of ideas after reading the specifics of a company’s business model.
• Risks – Companies detail all risks associated with the business. This is basically a list of what keeps the CEO up at night. Sometimes the risks listed surprise me.
• Competitors – Most companies list their top competitors.
• Trends – After I’ve read multiple reports from a company, I start to see trends and patterns (good and bad).
• Executive compensation – Executive compensation usually has its own section, with compensation plans described in detail. Large stock option grants based on hitting lofty stock price or market cap objectives seem common in CEO incentive packages.
• Ownership – The S-1, and sometimes other reports, detail how much of the company executives and investors own. Very interesting. Especially if it was VC backed.
• Stock-based compensation – A good number of technology companies have high stock-based-compensation expenses. This is essentially the expense the company incurs for paying employees with RSUs, stock options, etc. I’m curious whether this practice will continue at the levels seen in the last fifteen years, given how much it dilutes the holdings of other shareholders.
• Perception – After reading these reports, I sometimes reach a conclusion about a company that differs from popular opinion in the financial media.
• Dense – These reports are typically long. I can read them only when I’ve got an uninterrupted block of time when I can focus.

The filings of public companies are full of information that entrepreneurs and investors will find helpful. I wish I’d read public filings from companies in my industry when I was building my company. I’m sure it would have positively influenced my thinking and decision making. Anyone interested in reading these reports for their favorite company can search for them on the SEC Edgar website here.

This is my one-hundred-eighty-ninth weekly reflection. Here are my takeaways from this week:

• Suitable investments – Some generally accepted opinions about what constitutes a quality investment opportunity are illogical. They create pricing inefficiencies around supposedly unsuitable investments. Therefore, this type of investment can be acquired for less than fair value, which can lead to outsize returns. Investors who think outside the box and question the status quo are more likely to realize the outsize returns made possible by these unconventional opportunities.
• Constraints – Constraints, real or artificial, are helpful in spurring creativity and focus and business and personal pursuits. I want to experiment with adding more constraints to certain areas of my personal life. I’m curious to see what the results will be.

Week one hundred eighty-nine was another week of learning. Looking forward to next week!

I recently had a conversation with a friend about investing strategies. He’s smart and well educated, has an amazing career, and is forward thinking. We talked about public market investing, and I brought up the topic of compounding. He said he understood it and quickly moved on in the conversation.

He understood the concept, but I wasn’t convinced he understood the power of compounding. I shared a post containing a simple example that I wrote a few months back. When he looked at the numbers, it clicked. He understood how rate of growth and time work together to produce outsize results.

Albert Einstein famously called compound interest the eighth wonder of the world. It’s one of the most powerful forces that can be applied in many facets of life, not just money. Still, many don’t truly understand the power of compounding and aren’t taking advantage of it. They’re making progress toward their goals—but at a much slower pace than they could be.

I recently caught up with a friend who happens to be an investor at a large, Silicon Valley–based venture capital fund. His firm focuses on the seed stage, so they’re used to being the first check into a company before the incorporation papers are completed. He said his firm reviews over a thousand deals every month and he attends countless pitch meetings. 

I was fortunate enough to sit in when a seed-stage founder pitched him. At the end of the pitch, he gave the founder great advice on how to improve his pitch by communicating the company’s potential and his vision unapologetically (i.e., with extreme confidence). He left the founder with a quote that stuck with me:

Good founders help you see up the road. Great founders help you see up the road and give you a peek around the corner. What’s around the corner—IPO, big exit, big impact, etc.?

Seeing what’s ahead on the current path is easy because everyone can see it. No imagination or convincing necessary. But to help people see around the corner, you must paint a picture of what can’t be seen and get people excited about the possibilities. A great founder can do this, and it helps with raising capital, recruiting, and closing deals with customers and partners. My friend’s firm believes that the ability to help others see around the corner is a superpower that great founders have. Building a company is hard, but this superpower increases the chances of outsize success.

If you’re a founder or aspiring founder, ask yourself, “Am I helping people see up the road and around the corner?”