Text Analysis of Howard Lindzon’s Blog

After analyzing Fred Wilson’s blog posts, I got connected with Howard Lindzon and did the same thing for his blog. I wasn’t as familiar with Lindzon’s writing and it’s been fun to dig into it — where Wilson is measured and understated, Lindzon shoots from the hip and is irreverent. I most enjoyed reading some of his takes from the mid 2000s. It reminds me that the more things change, the more they stay the same:

We need VC’s to stop writing panicky letters to their CEO’s that they OVERfunded the week before and move forward. When our ‘leaders’ panic and get all philosophical and whiney, you get what we have now.

We need to abolish the FED and get back to capitalism. Too many rules equals fluff and excuses.

This of course sounds like it could be a tweet from 2022, but Lindzon wrote it during the Great Financial Crisis in 2008.

The Power of Consistency

Like Wilson, Lindzon has been an extremely prolific blogger. Also like Wilson, he seems to have started blogging in a similar way to how people now use twitter, with several relatively short posts per day. Then, once the conversation moved to Twitter (and to StockTwits, which he founded), he slowed down, before settling into a daily blogging habit in 2017.

Note: a few months in 2007 are missing from Lindzon’s archives; thus the gap.

Analyzing both Wilson and Lindzon’s writing has further impressed on me the value of consistency and volume in creation. Very few people consistently produce things for years and those that do seem to benefit immensely from it.

Lindzon’s Interesting career path

You can see the fascinating range of things Lindzon’s worked on since he started the blog. He ran a hedge fund in the late 90s and has continued to reference that world in his writing.

He built WallStrip, a daily YouTube financial show, and sold it to CBS. Then he founded StockTwits, the social platform for investors (and pioneered the $cashtag). He then started Social Leverage, a VC fund. He’s been an angel investor throughout, though he mentioned it in his writing most frequently between 2012 and 2016. He also started a podcast, Panic with Friends (which is near and dear to my heart since I work on podcast creation right now).

Economic Trends Over Time

Lindzon writes a lot about financial markets and you can see what he’s focused on over the years. It is a slice of the last 16 years of financial trends. For example, you can see his focus on real estate increase during the mortgage crisis in the mid 2000s, dip, and then start to increase again as the housing market has heated up the last few years.

Clearly today inflation and how the Fed is handling it is at the forefront of his mind.

The Rise and Fall of Companies in Lindzon’s Writing

Technology Companies

You can see Lindzon’s focus on different technology companies move through the years. He has paid a lot of attention to Apple as a stock since the beginning of the blog. He invested in Robinhood through Social Leverage and has written a lot about it since 2014.

I included E-Bay because I was just listening to the excellent Acquired podcast episode about Amazon and it discussed Amazon’s battles with E-Bay in their early days, which seems so foreign now.

Investment Banks

Lindzon really seems to have a bone to pick with Goldman Sachs (the “Page Not Found” page on his blog likens the page to a Goldman banker’s ethics). He goes just a tiny bit easier on my close personal friend Jamie Dimon and JPM (I shook hands with Dimon once).

Value of Reading Old Posts

Doing this analysis has made me appreciate how valuable it is to read real-time reactions to historical events. We read so much analysis that is done after the fact but real-time analysis lets you pattern match things that already happened to current events: it lets you “backtest” the methods of thinking.

For example, Lindzon links to this post by Dave Winer about Facebook’s potential value and it is clear that Winer was thinking about Facebook’s potential in the exact right way, and Zuckerberg and Facebook executed beyond his expectations:

And there will be an easy way for an app to authenticate someone, and access data private to the app, and data that the user has let the app have access to. That way when I register to be part of a new community I don’t have to re-enter all my data again.

If Facebook has the guts and vision to become this network, then it’s worth everything, even $10 billion isn’t enough. Instead of Yahoo or Microsoft acquiring them, they will be in the buyer’s seat. And Facebook has a clear shot at doing it. But there’s no evidence that they get this, and no evidence that if they do get it, that they’re going to move aggressively to fill the need. (emphasis mine)

What is Facebook Worth, by Dave Winer, 2007

I could easily imagine this type of thing being written about a web3 social network today. And most people would think it is wildly optimistic. It is an interesting way to calibrate your thinking about current conditions. That is why I am hesitant to make fun of web3 companies even as that has come into vogue – you can find lots of writing doing the same thing with Facebook!

It also gives you a look at alternative histories that people forget about. Here Lindzon is writing about Microsoft buying Facebook for $10B. Even more fun, here he argues that Coke or Pepsi should buy it! Imagine that!

I still think Coke (or Pepsi for that matter) should come in this weekend and up Microsoft.

Coke can cut $10 billion in advertising over 10 years and at worst pay for itself that way. Microsoft could do the same really if they used Facebook properly, but they won’t 🙂


There are also lots of cultural references that it is fun to be reminded of. In this post Lindzon writes “I love seeing what all my Web 2.0 friends are doing.” One of his friends was making a remix of the Obama Girl video, which I haven’t thought about in 15 years.

This view of his mentions of US presidents demonstrates just how much Trump dominated our collective consciousness. Lindzon first mentioned him back in 2006, with a rather prescient post titled Trump – asshole?

He has an amusing preoccupation with millennials (disclosure: I’m one of them). I expect this is due to his home life: his About page reads, “My hobbies include golf and cycling. I am an empty nester (I own and operate two millennials).”

Gen X, as seems standard, goes completely unmentioned.

He also notes there that he is in pursuit of the perfect sleep solution, which makes two of us. If anyone from 8Sleep is reading this and wants to set something up, get at me.

Tech Waves

Since Lindzon writes a lot about tech investing you can see his view on tech trends develop as they ebb and flow. I am excited to see him writing a bit more about Social in the past few years because that space needs innovation.

He is particularly interested in fintech and so has written a lot about crypto and fintech startups. It’s fun to see his references to the 3 “phases” of the internet so far:

As each new phase develops, he references the previous phase as a basis of comparison. For example, lots of ink has been spilled this year about web3 and how it differs from web2 and web1 — this is the most concise summary I’ve seen:

Thanks for reading! I highly recommend you spend some time going through the old archives to read Lindzon’s takes on events from the early 2000s. It will help sharpen your perspective on things that are happening today.

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