I ended up choosing Tomorrow Health

Litquidity

Larger equity holding
More role autonomy
Part of job is writing
Learn how to build a digital audience
Getting in earlier, get to see more of what it takes to get from 0 to 1 vs 1 to 10

Longer hours
Some aspects of finance culture
Centered around finance and the news, neither of which I love
Ultimately the business is selling ads which I don’t know how transferable that is nor how excited that makes me
Reputation risk if the brand becomes too polarizing
Key man risk if Lit stops making good content or something happens to him, he is the brand and the business at the end of the day
Funding uncertainty currently
Crowded space, land grab mode, hard to differentiate