Hello friend,
Why you’re getting this: This is my Friends Newsletter; a dispatch from the frontlines of running weird businesses, hiring even weirder people, and learning things the hard way so you don’t have to. Unsubscribe anytime, no therapy required.
Here’s what I’m thinking about…
Over the last 15 years, I’ve hired hundreds of people across 75+ companies.
Some were A+ on paper.
Fancy degrees.
Big brands.
Impressive titles.
Bulletproof cover letters written by ChatGPT.
But here’s what I’ve learned:
The resume tells you what they’ve done. The interview tells you how they think. But the DNA? That tells you everything.
Let me tell you a story.
We once hired a rockstar exec from a high-flying SaaS company.
Enterprise sales legend. Polished deck. Great references.
We brought him in to lead a marketing-led, product-driven startup.
He told us he’d adapt.
He told us he “respected product.”
He told us he was “ready to learn the new playbook.”
Guess what happened?
He rebuilt the entire funnel around sales.
Out went content, brand, and community.
In came cold calls, SDRs, demos, discounting.
The lesson?
People don’t become what you hope; they become what they already are.
DNA > promises.
Forget resumes.
When I hire now, I look for a few specific traits:
The person who can’t stop learning.
The one who sends articles unprompted.
The one who says “I didn’t know, but I figured it out.”
They do what they say.
They tell the truth, especially when it’s hard.
They own their mistakes before I notice them.
Startups are chaos.
If you crumble in the first storm, you’re not ready for the sea.
Talk is cheap. Show me what you’ve built.
They know what “good” looks like.
This one’s underrated—and critical.
Here’s one of my go-to questions:
“What’s something you’ve done that felt totally unreasonable; but you pulled it off anyway?”
The best people light up when you ask that.
They tell you about:
It’s not about what they studied.
It’s about what they chased.
The best hires I’ve ever made:
We hired a customer service rep who’s now running ops across multiple businesses.
We brought on a designer from a tiny agency who now leads creative at Dribbble.
We hired a part-time finance analyst who became a CFO across three portfolio companies.
They didn’t have perfect credentials.
They had character.
Let’s rapid-fire what I don’t care about anymore:
All noise.
None of it predicts performance.
I’m working on a tool that scans your resume and replaces every buzzword with what you actually meant.
“Cross-functional leader” → “had 12 Slack channels muted”
“Strategic operator” → “made Notion templates”
“Results-oriented” → “vaguely remembered the goal once”
Still looking to hire character-driven weirdos.
If you’re not “qualified,” but you’re obsessed with something and you work like a demon… email me.
1. What if someone has great experience but bad attitude?
Nope. Hard pass.
2. What if they’re amazing but don’t interview well?
That’s okay. Most geniuses are weird. Give them a project, not a panel.
3. Do you believe in “culture fit”?
Sort of. I care more about “culture add.” Show me your weird.
4. Can you teach character?
No. But you can spot it early.
5. What about raw intelligence?
Overrated. Smart is easy to find. Driven is not.
6. Do you hire generalists or specialists?
Generalists early. Specialists when it starts to break.
7. What’s the biggest hiring mistake you keep repeating?
Believing people will “change” into what I need. They won’t.
8. How long before you know it’s a bad hire?
Two weeks. Sometimes two hours.
9. Should I trust my gut?
Yes. It’s usually right. Especially if you’ve hired 100+ people.
10. What’s your one-line hiring philosophy?
Hire for DNA. Train for everything else.
That’s all for now…
The best resume is how you live.
Get Your Copy of Never Enough at https://www.neverenough.com
Did you enjoy this newsletter? Say thanks by checking out one of my businesses:
