Note: if you like AVC, I have been writing on substack more regularly and you may enjoy it, especially this post about quant in venture capital or this post about Tiger Global.
I’ve been reading Fred Wilson’s blog AVC most days for 4 or 5 years now. I admire the way he writes: simple sentences that have a clear point of view. He doesn’t hide behind complexity or jargon, and he doesn’t hedge every opinion for fear of being wrong. I’ve tried with mixed success to incorporate that into my own writing.
His investment record and reputation as a VC are also obviously incredible, and I value his perspective on the world.
I decided to analyze the text from the posts on his blog. I wanted to analyze both the style and content of his writing, understand the patterns and see what has changed over time. It was incredibly fun. Like strolling through a museum of the history of technology since the early 2000s. These are the things that struck me most.
Wilson is incredibly consistent
Wilson has been writing consistently for 20 years! As someone who has struggled to remain consistent in between bouts of creativity, his commitment is really inspiring.
It seems like he treated the blog similarly to a twitter account before Twitter blew up, and then settled in to a daily posting habit for the next 15 years, slowing down a bit in the last 2.
He was very early to crypto
USV invested in Coinbase in 2013 and Wilson has been writing about bitcoin since 2011. Must be nice!
You can see tech evolve through his writing
I broke Wilson’s posts into 4-year “eras” and used TF-IDF scores to find the most distinctive phrases in each era: the terms he used a lot in each era relative to other eras. For example, “covid” was obviously near the top of the 2019-2022 era while “iphone” was near the top in 2007-2010.
The result is a journey through the past 20 years of Wilson’s blog and his view of technology and society:
A few of my observations:
- You can see companies and platforms rise and fall through the eras. For example: myspace and rhapsody in 2003-2006, Blackberry and Tumblr in 2007-2010, Kickstarter and Kindle Fire in 2011-2014, Quizlet 2015-2018 and now Top Shot in 2019-2022. It is a reminder of how ephemeral business and technology can be.
- I like seeing the evolution of the features in his blog. He wrote about his top albums in the early 2000s, had “MBA Mondays” in the mid 2000s and “Funding Fridays” later on. When you write as much as he has you have to introduce new concepts and evolve what you’re focusing on.
- Even though I’ve been reading the blog since 2016 or so, I haven’t thought of it as particularly crypto-focused, so it’s interesting to see how much crypto comes up in this analysis.
Using these terms as inspiration, I looked into some trends over time in his writing. These were a few of my favorites.
Posts mentioning companies
It’s interesting to see the companies that Wilson talks about. I know USV was an early investor in Twitter and it also is integrally linked to blogging so it makes sense that he mentions it a lot. Yahoo is a fun reminder of how important it used to be and how quickly things can change.
Liquidity routes
One of the things I like most about Wilson is that none of his writing feels like VC Brags. He does not come across as self-congratulatory. But because of the business he is in it is interesting to see how he has talked about various forms of startup liquidity, especially the rise of tokens recently and the decline of mentions of IPOs in the early 2000s.
Tech Evolutions
You can see the amount of attention he has paid to various hype cycles and evolutions in technology. It is interesting and exciting to me that he has been talking about social more in the past few years, perhaps as web3 companies have started to innovate in that space.
The early web seemed really fun
I discovered lots fun things in the history of the internet by looking at the most distinctive phrases from Wilson’s posts from the early 2000s. Some of my favorites:
Wilson used to have a section called VC Cliché of the Week, which I like a lot.
I had never heard of hackoff.com, a murder mystery written online and set in the internet bubble.
There were wonderful retro startup names, many of which were new to me. Boxee, Friendfeed, outside.in, and my personal favorite: audioscrobbler, the name of the recommendation engine for last.fm. Audioscrobbler! Not to pick on Brex, but wouldn’t you rather live in a world of audioscrobblers than a world of Brex’s?
MSO (multi-system operator): I had never heard of this, but apparenlty it refers to operators of multiple cable television systems.
Wilson used to blog about about music a lot (and apparently he really liked Wilco). In part I expect there was a lot more startup activity in the music space in the early 2000s. But it also seems like Fred was writing more for his friends and himself than the public, having fun with a new way of expressing himself and building community:
This makes me nostalgic for a period of the internet I didn’t fully experience. I like Twitter, but it has such a different feel to it than these old posts do: it is so much faster, and of course it is mediated by the algorithm which rewards instant gratification and mass appeal. No one tweets the way Wilson writes and that is too bad. Maybe there are corners of the internet where this sort of wholesome interaction with is happening now (web3 where you at??) but if so I am not a part of it.
He experimented with Google Adwords very early on in order to learn about it. I don’t have the data but I have to imagine people are paying a lot more for “Venture Capital” clicks now than Wilson was in 2003.
I bought some keywords this morning. I bought “venture capital” and “blogs”. It’s too early to tell, but I think “venture capital” will cost me about $0.50/click and “blogs” will cost me around $.25/click
AVC post in 2003
Wilson’s actually gotten a bit more verbose over time
I have always admired Wilson’s brevity and ability to convey a lot of meaning without many words. But his average words per sentence have actually gone up a bit over time. I expected he would become more concise as he gained experience as a writer, but maybe he has always been concise and has actually learned to flesh out his thoughts a bit more over time. I am curious if that is a conscious progression or a natural one.
Closing thoughts
AVC is a great blog and I’d encourage you to read it. There is a lot of nonsense in VC and in tech but there are some very smart people like Wilson who are optimistic about what technology can do for society and I’m glad they are out there.
If you have any questions, feel free to reach out on twitter or via email at joe @ [this website], I’m happy to chat.
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