It's harder to procrastinate on "I do this every day" than on "I do this 3 times a week".

Making sleep non-negotiable is the only thing that made me survive building Plane post-YC without any major long term damage to my health.

If you think of "storytelling" as "spin", you refuse to learn one of the most powerful skills to get ahead in life.

No judgement lol. I just haven’t seen the same effect scaling @plane.com.

At the scale where that matters scaling support will likely be a bigger worry than tax admin.

Lots of great reasons to keep your team small, don’t get me wrong! But the administrative overhead is the least of your worry.

The communication/management overhead ends up being the dominant factor. And it’s much harder to pay someone to take care of it for you.

It doesn’t have to be. You could choose not to offer retirement/benefits to folks and let them figure it out. Or pay someone to manage it for you, like a PEO.

I hear that Chrome may soon be up for sale. www.theinformation.com/articles/openai-consider...

It seems like if you have a large Postgres table and need to add a virtual column to it you’re out of luck? Postgres only support stored virtual columns and adding one locks reads and writes.

Congrats on the launch! This looks great. We’re on Heroku Postgres for our warehouse but query performance is starting to be an issue.

Stripe → Fivetran → Postgres to do our own analysis is how we do it. Was never able to get an off the shelf tool to report MRR correctly.

Second-time founders often see why things won't work first, and forget to ask, what if it does? Experience kills boldness.

github.com/Shopify/limi... with Sidekiq capsules is also a good option

Cookies Are Forever would make a great Austin Powers reboot.

Any Paul-organized event is a default yes!

As a founder, moving from doer-in-chief to builder-in-chief is *hard*.

Early on, you do everything. But as you grow, you need to start focusing on things only you can do.

Setting the vision, allocating resources, hiring top talent.

Your job isn't to do more—it's to enable more.

🌶️ take: listening to podcasts too much is bad for you

You get used to always having someone in your ears. It makes you less comfortable with silence. Less likely to have your own original thoughts.

AirPods made this much worse for me because they're always in.

TIL: You can prompt AI by giving it the outcome you want (for example of a piece of writing) and asking to write a prompt that will produce that outcome.

Strong stratēchery vibes :)

Is there a starter pack for startup founders and investors?

Great list! Been missing other founders and builders here.

👋

Let’s get @plane.com on the list! 🙌

Great write up! I’m happy Plane was a tiny (haha) part of your journey leading up to this outcome. 😊