Last weekend was a holiday weekend, and I challenged myself to add five of my old reads to the library on this site (see here). It took longer than I’d planned (see here), but it forced me to review the notes and highlights in books I read in 2023, which was helpful and much needed. I want to regularly add more old reads to the library and review their highlights.

I know myself. If it’s not a regular habit, the chances of it happening are much lower. So, I’m going to experiment with a new challenge this weekend. If it works, I’ll keep doing it every weekend, hopefully. The challenge: add two old reads to my library by Monday.

It’s a simple goal, but it involves a lot of work behind the scenes. I’m hoping I can knock it all out this weekend, learn from it, and repeat it next weekend.

Wish me luck!

I enjoy learning about venture capital firms, and First Round Capital is one I kept tabs on. Its investments in Roblox and Uber were what originally sparked my interest in the firm a few years ago (see here and here). Josh Kopelman, founding partner, gave an interview recently in which he shared facts I didn’t know about First Round and explained some important concepts in VC.

Here are a few of my key takeaways from the interview:

• VC firms have grown from fewer than roughly 850 employing 1k–2k investors writing checks in 2004 to, today, over 10k funds employing over 20k investors writing checks.
• Venture firms, to attract larger pools of money into the VC asset class, are beginning to adopt the Blackstone asset management firm model. Blackstone is playing a scale game that focuses on cash-on-cash returns. Traditional venture capital has focused on alpha, which provides a superior internal rate of return (IRR, a measurement of compounding rate of return). Blackstone’s model is to provide higher cash dollar returns, as its dollars under management are massive, but lower-percentage returns that are steadier.
• The Venture Arrogance Score is a calculation Josh runs that looks at two things: how big the fund is and what percentage of a company the fund owns when the company exits. He said a hypothetical $7 billion venture fund that aims to own 10% of a company when it exits would need to capture roughly 50% of the dollars that venture capital realizes at exit during the three-year period when the fund is making investments. No firm has ever captured more than 10% of the total venture capital dollars realized from companies exiting.  He details the math in this section of the interview. He doesn’t say this, but assuming that a single firm can get 50% of the total exit value created by all founders in the U.S. when history says the very best get less than 10% is arrogant. The math doesn’t math on generating superior returns for massive venture funds.
• First Round aims to make 70 to 80 investments from each fund and own 12%–15% of a company initially. It targets 8%–9% ownership after dilution when a company exits. The firm takes Series A pro rata.
• First Round has been in business 20 years and made 90% of its profits in a 36-month period. VC makes its money by holding investments until the market is at the irrational disequilibrium or “extreme f*ing greed” part of the cycle. Bill Gurley agrees with this view (see here).
• A VC investor who started in 1980 and retired in 2000 made 17% of his profits in the first 17 years (1% per year). He made 83% of his profits in the last, 1997–2000 period.
• Multiple expansion in irrational disequilibrium and “extreme f*ing greed” is how VC returns are maximized.
• First Round is run like a company, not an investment firm. The firm has a CEO-type partner who doesn’t invest. He focuses on strategic planning, running experiments, iterating and learning, and offering products and services that add value to founders.
• First Round’s partners make their money from carry (profit sharing), not management fees.
• For the first seven years, First Round spent more on staff and products and services for founders than it took in from management fees. It invested ahead of planned growth. The partners had to contribute almost $8 million from their own pockets to fund the management company during this period.
• First Round still spends most of its management fees and has a staff of approximately 50 people.
• Value in venture capital firms is created by how they make decisions. Yet, many firms don’t capture their decision-making process so decisions can be analyzed and learned from later.
• Many venture capital firms are run poorly because founding investors don’t think of the firms as companies creating products or offering services to customers.
• First Round created a 36-question rubric that each investor answers before the partners discuss a potential investment. They want to capture each partner’s independent thinking before groupthink has a chance to creep in. This creates the fabric for debates about investments and game tapes to be reviewed later. Their goal is to capture the root of their investment decisions.

Those are my big takeaways from Josh’s interview, but he discusses a lot more. If you’re interested, check out the entire interview here.

In 2024, I began reading a biography (usually) every week, and I’ve added all those books to the Library page of this website. But I read books before 2024 too, and I want to share those as well. I aim to add them to the Library page on this site over time. A few days ago, I said I’d set myself a Memorial Day Challenge to add five of them.

I’m happy to report that I checked that box. Here are the books I added:

• Limitless by Jim Kwik
• Unknown Market Wizards by Jack Schwager
• Broken Money by Lyn Alden
• The Dhandho Investor by Mohnish Pabrai
• The Little Book That Still Beats the Market by Joel Greenblatt

This was a fun challenge. It took longer than I expected, but it was worth it. I spent a decent chunk of time reading the highlights and notes in each book. It was a nice refresher and reminded me of concepts I hadn’t revisited in almost two years.

Hopefully, sharing these books via my Library will add value to someone else.

As a first-generation entrepreneur, I’m committed to learning as much as I can about entrepreneurship. The best way I’ve found to do it is to study other entrepreneurs. To do that, I read a book every week, usually a biography. I share it in my Library on this site, and every Sunday, I post the latest book I read.

I recently listened to an interview of Josh Kopelman, founding partner of First Round Capital, a well-known, seed-stage, venture capital firm. One of Kopelman’s points is that most of the profits in venture capital are made in parts of the financial market cycle driven by “extreme f*ing greed” and “irrational disequilibrium” (see the clip here). This interview reminded me that financial market cycles have a profound impact on entrepreneurs and the investors who back them.

Last year, I read Bull!, which chronicles the financial booms and busts between 1982 and 2004. I wanted to go back further. I found exactly what I was looking for in a book that goes back hundreds of years, A Short History of Financial Euphoria. It’s short, a quick read, but does a great job of recounting history’s most famous financial bubbles—from the 1600s’ Tulip Mania to the 1980s’ junk bond frenzy and savings and loan crisis.

This book was straightforward and read like a mini biographical anthology. It details each bubble, including its origins, how it was created, and who the major players were. It describes the patterns each major speculative financial bubble follows and how to spot the signs of a bubble.

Anyone interested in the financial cycles and how to spot speculative euphoria may enjoy this book.

Current Project: Reading books about entrepreneurs and sharing what I learned from them

Mission: Create a library of wisdom from notable entrepreneurs that current entrepreneurs can leverage to increase their chances of success

Cumulative metrics (since 4/1/24):

• Total books read: 64
• Total blog posts published: 413

This week’s metrics:

• Books read: 1
• Blog posts published: 7

What I completed this week (link to last week’s commitments):

• Read A Short History of Financial Euphoria, a recounting of history’s most famous financial bubbles—from 1600s’ Tulip Mania to the 1980s.  

What I’ll do next week:

• Read a biography, autobiography, or framework book
• Add five more books to the library on this site—see more here

Asks:

• If you know any senior full-stack developers interested in working on the software for my current project, please introduce us!

Week two hundred sixty-nine was another week of learning. Looking forward to next week!

I hope everyone has a great Memorial Day with friends and family!

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Current Project: Reading books about entrepreneurs and sharing what I learned from them

Mission: Create a library of wisdom from notable entrepreneurs that current entrepreneurs can leverage to increase their chances of success

What I struggled with:

• No material struggles last week

What I learned:

• A first-generation entrepreneur who has had some success but is trying to scale further: This is a profile of an entrepreneur with unique problems. More thoughts on this here.
• X (formerly Twitter) bios matter. They help establish credibility. People are more likely to respond to cold DMs if your bio shows you’re credible.
• Google Tag Manager (GTM) is up and running on the blog. GTM allows for much more granular tracking of actions and events on a website than Google Analytics. But before I can make any changes based on GTM data, I need to increase the traffic to this blog.

That’s what I learned and struggled with last week.

I like to use my holidays to unwind, but I also enjoy challenging myself. When I do, sometimes I succeed, and sometimes I fail (I chronically overestimate what I can accomplish). Regardless of the outcome, it’s fun to have a challenge to work toward. I always learn something during the process.

I haven’t done a Memorial Day challenge before, but I want to experiment this year. I’m proud of the library section I added to this site. It includes all the books I read in 2024 and 2025. Now I want to expand it to include all books I’ve read over the last decade or so. I think it’d be cool to have all the books I’ve consumed and found helpful listed in one place. It’s a longer-term project and I haven’t gotten started on it yet. I want to change that.

My goal for this holiday weekend is to add five books to my digital library by Tuesday. These will be books I read before 2024.

That’s it. Super simple. Wish me luck.

Last year, I read a book by Felix Dennis. The title—How to Get Rich—isn’t my favorite, but it grabs people’s attention. The book is about succeeding as an entrepreneur, which leads to wealth—it’s not just about how to get rich. Dennis shares numerous lessons he learned the hard way as he built several companies, including Maxim magazine.

The book is a good read and contains lots of useful lessons for entrepreneurs. To see my takeaways, read my blog post series here.

One takeaway that stuck with me is about persistence and stubbornness. I regularly ask myself if I’m being persistent or stubborn when things aren’t going as I’d hoped. Here’s how Dennis describes the difference between the two:

Persistence is having the conviction that you’re right about something and that your point will be confirmed in the future (hopefully shortly). You simply keep going until you’re proven right. This is what entrepreneurs are known for. Simple enough, right? Well, how does persistence differ from stubbornness? Stubbornness is a form of persistence. You persist at something because you think you’ll be proven right. Stubbornness comes in when data or other evidence points to your likely not being right. Said differently, stubbornness is persisting even though signs are pointing to your being wrong.

Persistent people keep going, but they pay attention to red flags. If they’ve made a mistake, they change their plans. They persist, but in a different way—one that’s more likely to be successful. Stubborn people keep going and never course correct when they should.  

I think of persistent people as rational, clear thinkers. They’re grounded in reality and have the mental flexibility to acknowledge when they’ve made a mistake or bad decision. They acknowledge their error, regroup, and refocus their energies on the right activities so they can still achieve their goal.

I was stubborn once. I ignored signs that I was going hard in the wrong direction, and I regretted it. I vowed to do my best to avoid those kinds of mistakes going forward. Since reading Dennis’s book, I regularly ask myself if I’m being persistent or stubborn. I look for signs or data points that signal that I might be right. If I can’t come up with any, I know I’m likely being stubborn and need to course correct and put my energy into different actions that still align with my goal.

Recently, I started reading a book on financial history. I’m curious about the topic and think it could help me better understand the current financial landscape. I was excited when I received the book and began reading it, but I quickly realized I wasn’t feeling it. I was somewhat academic and a chore to read. The writing style wasn’t a good fit for me. I struggled to read thirty or so pages before I pulled the plug.

I’ve put pre-read steps in place to reduce the likelihood that I’ll start reading a book I won’t like, so this hasn’t occurred in many months. Because it isn’t happening as often, I second-guessed myself for a moment before I realized that I wasn’t the problem. The book was.

I read to gain wisdom from others and an understanding of topics that interest me. If a book isn’t helping me achieve those goals, I need to move on and find another book that will. There’s no shame in that. I’ve got an objective, and I’m on a mission. The world is full of books. If one isn’t working, there are plenty more to take its place.

I enjoy reading books from start to finish, one book at a time. But I’m not going to waste time. I finish books only if they align with what I’m trying to accomplish and aren’t a struggle to digest or comprehend.