When I started posting daily in 2020, I had a decade-plus of entrepreneurial experience from building a company. I thought about those experiences and identified insights about entrepreneurship. Then I shared my insights in a way that people could understand (and hopefully find useful).

Lately, I haven’t been getting as much from the process of creating my posts. I thought about why I feel this way and concluded that I haven’t been as consistent in sharing insights in my posts. More of my posts have contained information but not shared deep understandings. I realized that the process of gaining an understanding of a topic and then distilling and sharing it concisely is fulfilling. It isn’t always easy to come up with insights and communicate them, but I’ve enjoyed it when I have.

I want to get back to writing more insightful posts. To do so, I’ll need to accelerate the rate at which I acquire knowledge on certain topics and come to understand them.

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

• Schedule experiment – I’m almost two months into my schedule experiment. It’s no longer an experiment. It’s a habit now. Dedicating more time daily to reading to acquire knowledge led to my realizing that I was approaching reading the wrong way. I spent time learning how to be intentional about reading, and I began implementing a new approach this week. The early results are impressive. This could have a big impact on me going forward.
• Compounding – Most people think about interest and money in connection with compounding. But it applies to much more in life than money.
• Closing windows of opportunity – Some opportunities won’t be around forever. This week was a reminder to make opportunities with expiration dates—in all aspects of life—priorities. I may not know when they’ll expire, but I know they will and that I need to make the most of them while I can.

Week one hundred sixty-nine was a short but productive week. Looking forward to next week!

Bloomberg published an article today entitled Shares of Startups Are Turning Dirt Cheap, Attracting Venture Funds. It contains some insights into the current state of the secondary market for start-ups.

A secondary sale is usually a transaction between two parties to exchange equity in later-stage start-ups. The start-up isn’t involved, except that sometimes it must approve the transaction.

I know a few investors, both individuals and institutions, who bought or sold shares on the secondary market in 2020 and 2021. Usually, it was a way for the buyer to get exposure to a company when they couldn’t become an owner in a funding round. The seller was typically an early employee, angel investor, or seed-stage venture fund. These investments were done at a valuation premium relative to the last funding round.

Things appear to have changed. According to the Bloomberg article, recent secondary sales have been done at steep valuation discounts relative to the most recent funding rounds. And there is increasing appetite by funds to buy on the secondary market and increasing desire by institutions such as pensions to sell private investments on the secondary market.

As more institutional investors, venture capital funds, and start-up employees seek liquidity when an IPO isn’t an option, I’m curious to see how secondary markets evolve.

People emulate the habits of successful people. I think this is a good approach because consistent positive habits increase the likelihood of positive outcomes. But going deeper is even better. Understanding what actions led to success is helpful, but understanding why successful people consistently took those actions can be even more valuable. If you emulate actions without understand why, you might not get as much value from them because you don’t know what you’re looking for.

When I learn about habits that led to success, I now dig to understand the why behind them. Understanding this has helped me maximize the value of those habits I’ve emulated.

A while ago, I listened to an investor share that he keeps a log of all his lessons learned from each investment. (This is different than the investment memo that he writes when he’s evaluating whether he should make the investment.) After the investment is made, he keeps a log of lessons and observations. He started the log to try to minimize making errors more than once. Identifying the lessons, writing them down, and reviewing the log periodically was helpful to his investment process.

I’ve started a similar log, albeit a less formal one. I’ve been keeping a running list in the Notes app on my iPhone and laptop. I recently reviewed the log while considering a new investment and altered my approach to making that investment because of a lesson learned.

I’m a fan of logging my lessons learned. I hope to keep the habit up and compile a single list of lessons learned over many years that I can eventually share.

Today I listened to an investor describe how he prepares mentally for investing. It’s a process of continual learning by being focused and intentional with his reading. He reads with an intent to acquire knowledge on a specific subject. After picking a topic he wants to understand better, he finds books written by people who understand the topic better than he does. He focuses on identifying and understanding the main argument of each book, not consuming every supporting detail. This allows him to consume the most important parts of the books at the rate he deems appropriate (instead of consuming the books—with every detail and example that supports the main argument—at the pace the authors intended). This approach also allows him to compare what he’s reading in various books on the same subject and uncover valuable insights more easily.

There’s more to his approach, but that’s the gist of it. It really got me thinking. I’m going to learn more about it.

I’m a fan of evaluating people by how far they’ve traveled in addition to what they’ve accomplished. Two people may start at the same time and end up accomplishing the same thing, but one may have traveled twice as far because his starting position was much farther back. For example, if you’re evaluating two runners who finished a race in 10 minutes, you surmise they’re equally talented. Now consider that one runner’s starting position was twice as far back: he ran 2 miles while the other ran 1 mile. They both finished in an amazing time, but one runner outworked the other by traveling twice as far in the same amount of time.

My dad is the runner who traveled twice as far. He was born into a great but extremely poor family, in a place with limited economic opportunities, in a less-than-equitable period in America’s history. Through thirty-plus years of hard and consistent effort, he accomplished more than many of his peers, elevated his family’s economic well-being, and gave his children access to opportunities he couldn’t even imagine. All without a college degree.

From him I learned the following:

• The improbable is possible if you consistently work hard.
• You can win the game of life even if you’re dealt a bad hand. Focus on playing the hand you’ve been dealt as best you can—don’t dwell on your hand being bad.
• Don’t let yourself be defined by your starting position in life. You’re in control of your destiny.
• You can’t do what everyone else is doing if your situation is different than theirs. Make decisions and act based on your situation, not what others are doing.

Happy Father’s Day, Pops! Thanks for being a great example and putting in the effort to win even though you had to travel twice as far as everyone else.

Tiger Global is an investment firm founded over twenty years ago by Chase Coleman. Tiger has been investing in public and private technology companies for many years and has tens of billions of dollars’ worth of assets under management. It made waves in the venture capital industry for its investment pace in 2021.

Tiger closed a fund in 2021 that was reportedly $6.65 billion. And it closed on a $12.7 billion fund a year later (including $1.5 billion from firm employees, so $11.2 billion from outside investors) that took less than six months to raise. Read more about these funds and the firm here.

Last fall it was reported that Tiger was raising a new fund targeted at $6 billion. As of now, it has reportedly raised $2.7 billion, according to regulatory filings. (It’s still raising, and this figure could change.) Tiger’s ability to raise capital for technology investments has declined, and it’s not alone. Insight Global is a venture capital firm that reportedly has cut the target size of its latest $20 billion fund because of the challenging fundraising environment.

I don’t have inside information, and I haven’t talked to anyone at any of these firms or their LPs. But given rates paid on US Treasuries, returns required by LPs to justify illiquid venture capital investments are likely higher than they’ve been for ten years. Translation: LPs probably want venture capital funds to produce higher returns to compensate them for the risk of capital loss and the inability to access their capital for a decade. Combine that with the compressed multiples that technology companies experienced in 2022 (i.e., falling valuations), and fund managers are in a tough spot. They’re being asked to produce higher returns when exit valuations have come down (though this could go back the other way during the fund’s life).

This dynamic will likely have an impact on the venture capital industry if it continues. I’m curious to watch this and see how it plays out.

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

• Valuation methods – I’ve learned about another evaluation method. It’s interesting to listen to investors look at the same company and, using different valuation methods, arrive at different values. Sometimes great investments are in plain sight, but no one sees them. Investors just need to adjust the lens they’re looking through to see their true value.
• Wisdom – A friend shared a quote from Benjamin Graham. The publication of one of his books was delayed, but the book included better material because the delay allowed him to include “wisdom is acquired at the cost of much suffering.”
• Odds – I’ve been learning about how successful investors think about odds and risk. Sometimes you can reduce the risk materially by waiting until the odds of the investment having success tilt more in your favor.

Week one hundred sixty-eight was an enlightening week. Looking forward to next week!

I chatted with a friend who’s in the process of acquiring a business. Instead of using a bank to finance the debt portion of the purchase price, he’s using seller financing. That is, instead of taking out a bank loan and paying the full purchase price in cash, he’s accepting a loan from the seller. The seller gets paid part of the purchase price in cash at closing, with the remainder repaid over time with interest.

This is common, but I hadn’t heard about it being used as much in the last few years because interest rates have been so low. I was curious how the seller felt about it, so I asked my friend.

He said the seller envisioned selling the business, getting cash in a lump sum, and riding off into the sunset. Seller financing, which prevents a clean break from the business, wasn’t part of his vision. It took a bit of convincing by my friend, but in the end, they made a deal after a detailed walkthrough of the math.

Riding off into the sunset is every founder’s dream scenario if they want to sell, but it doesn’t often play out that way. Things like earnouts and seller financing are common and can mean the seller will get delayed payments over a period of time.