Hello friend,
Why you’re getting this: this is my Friends Newsletter; a raw stream of thoughts, war stories, and hopefully-useful screwups from my life as a founder, investor, and professional second-guesser. Unsubscribe anytime. No hard feelings.
Here’s what I’m thinking about…
I’ve made a lot of bad calls over the years.
Most of them came from ignoring a voice in my head that whispered one sentence:
"Should I let this person go?"
If you’ve ever asked yourself that, I already know the answer.
You should have done it yesterday.
Let me tell you a story.
A few years back, I hired a guy; we’ll call him Steve.
Steve was smart. Charming. The kind of person who says all the right things in an interview.
Harvard MBA. Fancy resume. The whole thing.
Two months in, I had this weird pit in my stomach.
He wasn’t bad, per se.
But things were… off.
Projects moved slower when he was involved.
People avoided working with him.
His updates were full of jargon and fluff, but zero substance.
I had the thought:
"Maybe I should fire Steve."
Then I did what every founder does when they don't want to feel like a jerk.
I told myself:
Three months later, I finally pulled the trigger.
Guess what happened?
The team threw an actual party.
(Yes, with cake.)
I’d become the bottleneck.
Everyone had known Steve was a dud.
I was just too afraid to trust the pit in my stomach.
Lesson learned:
The longer you wait, the more damage gets done.
Now, I follow a simple rule:
The moment you think “Should I fire this person?”; you already have your answer.
Not in a cruel way.
Not in a “people are disposable” way.
But in a “you already know this won’t work” way.
Same goes for projects, startups, partnerships, agencies, even friendships.
If I have to ask…
Should I kill this thing?
Should I step away?
Should I cut bait?
The answer is yes.
Always yes.
There’s a lie we tell ourselves as operators:
“Maybe it’ll get better.”
And sure, maybe it will.
But most of the time?
You’re just dragging out the funeral.
Firing someone slowly doesn’t make it easier.
It makes it messier.
People lose respect.
The culture suffers.
You burn time, energy, money, morale.
Rip the bandage.
Have the hard conversation.
Cut clean.
There was a time I got it right.
Hired someone.
Two weeks in, I knew it wasn’t going to work.
No chemistry. No ownership. Red flags galore.
I fired him after 10 business days.
Was it awkward? Yep.
Did I sleep better that night? Hell yes.
Did the company avoid a slow bleed? Absolutely.
I've never once regretted firing fast.
But I’ve regretted every single time I waited too long.
I used to fall in love with my own ideas.
Then marry them.
Then die holding their hand in a flaming house.
We’d spend 6 months building something that no one asked for.
Launch day would come and… silence.
Then we’d keep it alive like a startup Weekend at Bernie’s.
Here’s my new policy:
Momentum is everything.
Dead weight kills momentum.
Kill the dead weight.
I’m in the early stages of building a new AI agent; this one helps you fire faster (just kidding… maybe).
Name: ChopGPT.
One prompt: “Should I fire this person?”
Response: “You already have.” 😬
On a related note, I replaced my assistant with AI and haven’t looked back.
Less admin. Fewer people to fire.
If you’ve built tools that actually help you make hard calls faster (gut-check dashboards, one-pager triggers, deal-kill checklists)—send them my way.
1. Isn’t that too harsh?
No. Keeping someone in the wrong role is crueler than letting them go.
2. What about coaching?
Sometimes. But if you're already asking the fire question, it's usually too late.
3. What if I’m wrong?
Then you made a fast mistake instead of a long one.
4. What about probation periods?
Love them. Use them. But don’t let them become excuses to delay.
5. What about second chances?
Give them once. Not twice. Not three times. Once.
6. How do I know it’s time to kill a project?
When your gut says, “This isn’t working”—it’s already not.
7. Should I listen to my team?
Yes. If they’ve lost confidence in someone, it’s game over.
8. Isn’t this cold?
No—it’s honest. And it saves everyone time and pain.
9. What about the cultural impact of firing?
Firing fast actually improves culture. It shows you care about performance and fit.
10. What if I’m the one who needs to be fired?
Then step aside, my friend. You just passed the founder integrity test.
That’s all for now…
Fire fast.
Fail fast.
Live free.
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