Generally speaking expect your hair to go gray at a rate of 10% per funding round, until you go public when the rest turns gray after your first earnings call.

Fun fact: during Box’s Series B we were in the midst of pivoting to the enterprise, with an untested freemium model, and running out of runway. The strategy was speculative. Every partner we pitched passed, but one associate (Mamoon Hamid) fought to push the deal through, saving us.

What a glorious time it is in the tech industry that there’s a raging debate on what level of investor you should be pitching. These are first world problems. Back in my day we’d pitch you if you had a working email address.

It is insane that just 18 months ago the state of the art AI model had a 4K token limit, and today state of the art can reach 1M tokens. There are essentially no examples in history of a technology improving at a rate of 250X in under 2 years.

Oh god “delve” is now stuck in my head and I’m probably going to start using it in like every 3rd sentence.

One of the most common concerns about AI is the risk that it takes a meaningful portion of jobs that humans currently do, leading to major economic dislocation. Often these headlines come out of economic studies that look at various job functions and estimate the impact that AI…

VCs when .ai is in the name

One thing that we think a lot about at Box is how you build software for the future of AI when you have rapid advancements in what's state of the art. Every day, there are brand new AI models that perform better than the last, and we're witnessing a never ending race to lower AI…

Incredibly, when enterprises share the outcomes they want from AI, the answer is increasingly moving from “that will soon be possible” to “that is now possible”. The rate that AI costs are dropping and model quality is improving makes infinitely more ideas viable.

Steps for disrupting a market:

1. Find a market that is unnecessarily constrained due to the cost or complexity of legacy solutions.

2. Deliver a simpler, more integrated solution, and you will increase the size of the market by 10X.

3. Find the next problem and repeat.

Imagine being alive during GameStop and then coming to the conclusion that Reddit is the next stock to short. h/t Nikita Bier

AI definitely getting wild

This is the most important graphic in business. Misunderstand it at your peril.

The main lesson in software is to go after markets that are artificially constrained by bad tech. When you build something far simpler or more integrated than was offered before, you will invariably expand the market size by an order of magnitude.

At Box, we’re fundamentally believers that AI will drive productivity and growth for businesses, and will ultimately be a net boon for jobs in the long-run.

Truly the craziest thing of all time

Truly crazy. Stocks go up and down year to year, so you’d pay taxes on money you never made. And this directly disincentives startup formation. The innovation economy thrives on illiquid stock, so people would need massive debt to pay taxes for gains that haven’t yet happened.

The first Intel chip just 50 years ago had 2,300 transistors. NVIDIA’s new GPU has 208 billion transistors. The pace of technology advancement is amazing.

When we got the idea for Box in 2004, we researched all the ways you could store and share files online and found literally none had a modern approach. It was like discovering a secret hiding in plain sight. When you find one of these, throw everything you’ve got at it.

From a standing start I believe it would take me at least a decade of intense research to understand the significance of this Kate Middleton situation in the same way my wife does.