Charles Hudson

Teaching AI to Think Like Me Made Me Rethink How I Think I started building a lot of AI tools for myself and learned more about how I think than I did about how AI tools work.

open.substack.com/pub/chudson/...

First time not doing a fantasy football league in 20+ years and it feels weird!

I think this is a healthy development, but I've basically replaced most of my doomscrolling with tinkering around with Cursor and Claude code, and it feels like a much more satisfying way to kill time

One thing I find interesting about VC investing in AI cos is the investor desire to declare early winner. Last year very few ppl I know thought Claude would be a major player, it was all Cursor’s market to lose. Now many view this market as way more competitive - customers decide, not investors!

Charles Hudson (@chudson) I’ve been trying to find a better way to articulate some of the challenges investing in AI companies as a seed-stage investor. I’ve been thinking about the companies I meet and evaluating them on two ...

substack.com/@chudson/not...

Apparently!

First time seeing Lady Gaga live - she’s an incredible performer. High energy from start to finish.

I’ve been learning Python as a fun side project and as a way to better understand a few things that eluded me. It has been way more fun than I expected, especially now that I’m getting into MCPs!

Fund Size is Strategy - Extreme Power Law Will Make Portfolio Company Conflicts a Relic of the Past As multi-stage funds get larger and larger and the need to get into all of the power law winners is required to make their own fund math work, what happens to portfolio company conflict policies?

open.substack.com/pub/chudson/...

Today I learned that a lot of things people call co-pilots are just projects in Claude!

Uncomfortable and Unanswered Questions I Have as an AI Investor I've been in a lot of rooms with a lot of smart people who are working on the future of AI and a few important questions still feel unanswered to me.

Spent some time thinking about the questions im not hearing answered when it comes to the near-term impact AI is already having on white collar work: open.substack.com/pub/chudson/...

A lot of people seem to just want to be famous for anything, no matter what the thing is or what it costs them. Seems weird to me.

YouTube video by The Learning Corner by Precursor Inside Startup Purgatory: Retention, Returns & Recession Warnings

www.youtube.com/watch?v=REDN...

This week I got a lot of emails from work people that were clearly AI generated. This was the first week I didn’t roll my eyes or find it annoying - they were easy to read and well organized, but maybe lacked their personality and voice. Something felt different - maybe it was me, maybe it was AI

Investors Worry Trump’s Tariffs Could Cause a ‘World of Hurt’ for Startups Donald Trump's unpredictable tariff policies have unsettled the venture capital world, further darkening an already gloomy outlook for IPOs.

www.wired.com/story/tariff...

What Does It Mean to Be a Venture Capitalist Today? Some thought on our business and where things might go from here

chudson.substack.com/p/what-does-...

I've heard of people declaring email bankruptcy - I'm considering declaring text messaging bankruptcy!

Whenever I look at the number of daily logistical text messages I exchange with my wife, I can’t imagine what parenting logistics looked like before phones.

Celebrities want to stay famous, rich people want to stay rich, and politicians want to maintain power. Sometimes it’s just that simple.

Early in my investing career I heard the old saw “never try to catch a falling knife” when markets fall. As a VC, I feel like I need the equivalent of “never try to grab a knife attached to a bottle rocket” to describe investing in AI startups. Either way you end up with a bloody hand in the end.

I wrote this before I saw the posts about the book after talking to a bunch of friend who worked at a variety of big tech cos!

Only worked at one public tech company, glad it wasn’t that one

I hope it was worth it

Lifelong NBA fan. Never thought I’d see a year where my adopted Warriors and my hometown Pistons were both legit playoff teams!

I spoke with a journalist asking for tips on the most interesting consumer AI companies. It was hard to think of good examples at scale other than ChatGPT and Perplexity.

I have no idea why it took me so long to find @thestorygraph.com but I am so glad that a fellow reader encouraged me to sign up.

What if the Current Tech IPO Drought isn't a Drought but the New Normal for Venture? What happens in a world where we have fewer, bigger IPOs that take longer to mature?

First new longform post of the year! I’ve been thinking a lot about the lack of tech IPOs and what that means for smaller funds like mine. I think we are in a new normal of bigger but less frequent IPOs.

open.substack.com/pub/chudson/...

Lately I’ve seen a lot of people at the airport traveling in full hiking/trail gear - hiking pants and utility hiking shirts and sometimes hiking shoes, too. Is this a thing now? Is this about comfort, utility, or something else?