Brian Bailey

Head of Product Strategy at 37signals, makers of Basecamp, HEY, and Fizzy. Writing on product at

[Brian Bailey @bb]

We spent a year building Basecamp 5, which launched last week. One phrase kept coming back to me throughout: Don't accept the premise.

But that may have also been because I was watching Taskmaster 😄

https://t.co/DMjz76SlmY

[Brian Bailey @bb]

@JBLEWIS1983 Can't wait. My list of favorite albums is dominated by yours. Thank you, thank you, thank you.

[Brian Bailey @bb]

Quite a week! @Arsenal win the Premier League for the first time in 22 years, @nyknicks reach the finals for the first time in 19 years, and after a week together in Copenhagen, we launched Basecamp 5, the best version in its 22-year history. Take a look: https://t.co/tsityHaunP

[Brian Bailey @bb]

I just happen to follow @Arsenal, @Cubs, and @nyknicks, so the last 10 days have been a lot of fun.

[Brian Bailey @bb]

I've yet to come across two words in product development that make me cringe more than "backlog grooming".

[Brian Bailey @bb]

@K_Scanlan_ Hello! I'm forever grateful for your work and every patiently chiseled sentence within it. Do you, by chance, ever work with writers who aspire for the concision and purity of your writing and NOON? The options are few in the writing world.

Wishing you all the best!

[Brian Bailey @bb]

The only logical follow up to the Recordables podcast is... Adorables!

[37signals @37signals]

Introducing Adorables — a new podcast from 37signals!

[Brian Bailey @bb]

@WatchMarquee Every year starts with ticker experiments and then it's dropped after a bit. Please let that be the case this year 🙏🏼. One of the best parts of the broadcast is no ticker. It's just not the right fit for beautiful games at Wrigley.

[Brian Bailey @bb]

Working on Basecamp 5 and hit a bug. Deleting one weekly meeting deleted all future ones, too.

Or is it? If Fizzy has an entropy feature that cleans up inactive cards automatically, maybe Basecamp should cancel recurring meetings after 3 months to see if anyone misses them. 🙂

[Brian Bailey @bb]

A lovely essay, very much in the spirit of a past project, Uncommon in Common.

"I know how this is supposed to end. I'm supposed to tell you to simplify. Audit your subscriptions. Curate your devices. Own less.

I'm not going to do that."

https://t.co/XVkqIM6Yh0

[Brian Bailey @bb]

"Coding agents dramatically drop the cost of typing code into the computer, which disrupts so many of our existing personal and organizational intuitions about which trade-offs make sense."

We're learning on the fly what the new trade-offs are.

https://t.co/doh4PHlvAr

[Brian Bailey @bb]

This from @davidcrawshaw perfectly captures where things are rapidly heading.

"I implemented that entire Stripe product (as it relates to me) by typing three sentences. It solves my problem better than their product."

Via @simonw

https://t.co/g7xr55igb8

[Brian Bailey @bb]

Great post from @om

"This new power should turbocharge our capabilities. And in order for that, it has to live inside the tools we already use. Smaller, focused, embedded."

https://t.co/ZZ29NO8FY8

[Brian Bailey @bb]

@philsinatra Possibly! Since it's not on a consistent schedule, it works a little better on YouTube, plus there is some screen sharing. You can always listen in your car via YouTube 🙂.

[Brian Bailey @bb]

A new episode of Recordables is here! Beyond the technical insight, it's filled with lessons about how to approach massive projects like this and the human side of dealing with risks and unknowns. Highly recommended!

[Jorge Manrubia @jorgemanru]

Ever wondered how you move 10 petabytes and billions of files off S3 without a second of downtime? @bitsweat explains:

https://t.co/w2yu2F5UEv

Jeremy is probably the best programmer I know. We often joke about how he knows everything about everything computer-related (and this is pre-AI 😂). You should listen.

[Brian Bailey @bb]

This is a great look at Fizzy, plus an interview with @jasonfried.

"I was struck by the presence of a distinctive design and sense of whimsy that’s largely faded from the greater software universe."

https://t.co/erKZJSlz5U

[Brian Bailey @bb]

The big surprise in my Albums app 2025 wrap-up is that there were 49 days when I didn't use it. It lets me curate my music library as obsessively as I like and then tell my friends all about it repeatedly. That it's built by a single developer is madness! https://t.co/UkRktSyYly

[Brian Bailey @bb]

I love a line that catches you by surprise, like this one by @FredKatz on the @nyknicks:

"This seems to be the new way of the Knicks, a Ratatouille-esque belief that anyone can cook, even that unrefined, inexperienced and once-forgotten second-rounder."

https://t.co/YdgQSjMVB2

[Brian Bailey @bb]

I wonder how many conversations at work, home, and school these days include someone saying "Well, AI said it was great."

[Brian Bailey @bb]

@ahmednadar Kind of you to say, Ahmed. I hope to!

[Brian Bailey @bb]

We use Shape Up when we build a new product like Fizzy, but it looks quite a bit different than cycle work on an existing product. We call it New Product Mode. Here's how it works: https://t.co/qqBeVzYiYa