Jack

Kept building companies. Kept getting stuck at hiring. So I'm fixing hiring.

[Jack @jackcheshire]

@alex_barashkov Got two brand decks this month. Agency: three weeks, four creative directors, $40k. Intern: Higgsfield, one sandwich. Picked the intern's

[Jack @jackcheshire]

@RayDalio swapped our first engineer for a "real" vp eng at sixteen heads. board called it maturing the org. we matured right out of shipping

[Jack @jackcheshire]

@shotguncaio company two we shipped every friday for 14 months. grew nothing. consistency on a broken loop is the most expensive habit you can build

[Jack @jackcheshire]

@ggreenwald every bridge round deck reads like this. dying and dominant, simultaneously. pick one

[Jack @jackcheshire]

@tenacious_ar company two, paid a KOL 28k. 1200 signups, 9 still active by day 30. most expensive user research we ever bought

[Jack @jackcheshire]

@DavidOndrej1 @OpenRouter more providers isn't redundancy when half of them route to the same coast. our pipeline died for 4 hours last month and the openrouter dashboard stayed green the whole time

[Jack @jackcheshire]

@ole_eth shot 40 before one didn't feel like a hostage video

[Jack @jackcheshire]

@NiphermeDave watched a founder pass on a sale at company two. called it discipline at the time. company was dead 14 months later. word usually means whatever the outcome lets it mean

[Jack @jackcheshire]

@paulg every "bad take" in a board meeting i've sat through was code for "i didn't read the deck"

[Jack @jackcheshire]

@TTrimoreau internal dashboards. built three at company two for visibility. nobody opened them after week two

[Jack @jackcheshire]

@RayDalio hired a fractional cfo at company two. eight months in his runway slides were six weeks longer than the bank account showed. board meetings got quiet after that

[Jack @jackcheshire]

@dhh company two, everyone picked their own keyboard. no logos, no palette. that was the bespoke part. the branded stuff we ordered ended up in a drawer

[Jack @jackcheshire]

@chooserich took four days off earlier this year. came back to two model drops and a pricing page I had to rewrite from scratch. haven't tried it again

[Jack @jackcheshire]

@base @OpenGradient every funding cycle someone tries to solve a product problem with cryptography

[Jack @jackcheshire]

@DeryaTR_ what used to take a couple days, you did before your morning was over

[Jack @jackcheshire]

@ardent__dev third company deep. what pattern are you noticing that nobody's talking about yet?

[Jack @jackcheshire]

@SaidAitmbarek taste is the one thing that doesn't compress

[Jack @jackcheshire]

@OpenAI as long as you dont degrade performance like someone else we know im here for it

[Jack @jackcheshire]

Started company thinking I'd finally hire like a grown-up.

Monday: posted a role. 400 applications by Tuesday.
Wednesday I'm drowning.
Thursday I gave up and built a tool to read resumes for me.
Friday I hired one of the candidates it ranked in the top 3.

No regrets. Actually using it on every role now.

What's the hiring shortcut you swore you'd never take?

[Jack @jackcheshire]

@bradbuildss symmetry not enthusiasm is the whole game. best collabs I've seen, both sides could sketch the other's win on a napkin before anything started