This weekend I hosted an AI generated dinner party.

We decided to test the limits and let ChatGPT generate the theme, menu, and even the recipes.

What ensued was surprisingly delightful. Our goal was to host a dinner featuring cuisine that was unique/highly unusual/unexpected.

Can the AI generate a novel experience for us?

First try. Fine, but not unique.

One of the most underrated ways to win in business is to convince very talented people to work in an industry usually occupied by B and C players. Uber beat the taxi cartels by deploying Harvard MBAs.

Flexport took freight forwarding with ex-consultants.

The playbook works.

I launched an Income Share Agreement (ISA) company in 2019.

Our company survived, but our use of ISAs did not.

Overall, I think the ISA experiment has failed and is not the revolution we hoped would transform training and education.

Here's what I learned 👇 ISAs tend to have significant adverse selection problems, stemming from two sources.

First, the lack of skin in the game leads to very poor participant behavior.

Participants haven't put anything down so it's easier to not complete the program.

When starting a startup or launching a new brand, your name really matters.

You don't just want a good brand name, you want an A-PLUSS one:

Appropriate
Pronounceable
Likeable
Unique
Spellable
Short

This is the framework we used to name @placement. Appropriate

Does this name fit your product or business? If you wind up iterating or expanding, can you keep the same name?

ie. Mailchimp is a great name for an email service, but not great for an all-in-one marketing platform

Here is the #1 most important career advice I can give:

DO NOT HAVE A RESUME FULL OF SHORT STINTS.

Roughly, more than 3 consecutive jobs with less than ~18 months tenure is career danger zone. This advice is based on research we've done at @placement.

This is the #1 most cited red flag by hiring managers in knowledge work industries by a *very* big margin.