scripod.com

We had six months left

Shownote

I just had to lay off some of the most talented people I've ever worked with and it fucking sucks.

Highlights

Running a business often means making tough calls, especially when financial pressures collide with personal values and team loyalty. This episode dives into the emotional and strategic weight of leadership during uncertain times.
03:32
75% of the engineering team was laid off to ensure financial stability
10:38
AI is a double-edged sword: it makes Tailwind more popular but also contributes to business struggles.
17:26
Privatized tailwindcss.com repo due to emotional stress from financial pressure
24:01
Jordan can do almost everything and solve any problem
31:01
Business is harder than programming.

Chapters

Is it time to face the music on falling revenue?
00:00
Why did we have to let go of most of our engineering team?
03:32
Returning to the code: can I help save the company by coding again?
10:38
Cutting features and closing doors: what survives in a crisis?
17:26
Who were the brilliant minds we lost—and what did they leave behind?
24:01
How do you stay hopeful after losing your best people?
31:01

Transcript

Adam Wathan: All right, going for another walk this morning in the post-freezing rain winter apocalypse that is Southern Ontario in January. A lot of things to talk about in this one. Some kind of, I don't know what the right word is, but not great things....