Cautious Optimism

Cautious Optimism

Home
Archive
About

Sitemap - 2023 - Cautious Optimism

Four things I'm curious about in 2024

In defense of looking like shit

The platforms will never stop hungering

Seven years of not drinking is a good time to question your life's direction

One good way to engender a crisis of self is to have a baby

Sorry, but I don't think that you deserve a bailout [Updated] [Updated again]

Bonding

How much did Stripe's growth slow in 2022?

Tech tries a new trick: efficiency

What's the point of having a billionaire owner if you don't get to avoid economics?

Why great startups are built in lousy times

How screwed is Twitter now that its debt payments loom?

It's duck hunting season but instead of ducks it's Duck Creek and instead of hunting it's private equity

Big tech won't save you

If you like startups you should love anti-trust

Elon Musk isn't even an interesting Republican

The venture slowdown could save blogging

How hard will corporate cost cutting hit startups?

© 2025 Alex Wilhelm
Privacy ∙ Terms ∙ Collection notice
Start writingGet the app
Substack is the home for great culture

Share