500+ Entrepreneurs Later - Who I’d Work With Again (and Who I Wouldn’t)

Spotting the right people early makes all the difference

After working with hundreds of entrepreneurs, a few patterns start to show.
Pitches. Projects. Collaborations.
Some turn into long-term partnerships. Some into genuine friendships.
And some… just a one-off call I quietly hoped wouldn’t happen again.

Recently, I decided to sit down and write a list.
Not out of frustration - just to get clear on something: What kind of people do I actually want to work with again?

Time’s too short to waste it on the wrong fits.
And life’s too short to work with assholes. But how do you know if someone’s solid before you’ve actually worked with them?

You don’t always. But there are signals. Small things early on that usually give you a pretty good idea. I used to ignore these. Now I pay close attention.

So here’s what I’ve learned - what separates the ones I’d go back to in a heartbeat from the ones I’d rather not cross paths with again.

1. Kindness > Ego
The sharpest people I’ve met are often the kindest.
No flexing. No power games. Just quiet confidence and respect.
The arrogant ones? Usually overcompensating.
Kindness lingers - it’s what you remember long after the work ends.

2. Contagious hustle
These founders have energy that moves the room.
You leave a call with them thinking: “Yeah. Let’s go.”
They don’t talk about doing the work - they do it. And you want to keep up.

3. True collaboration
They don’t treat you like a service provider. It’s a partnership.
They value your time. They listen. They work with you.
No drama, no ghosting, no tug-of-war over dumb stuff.

4. They go deep
You can tell when someone’s done the work.
They know their space inside-out.
They don’t bluff or wing it. When they talk, you learn.

5. They ship
They’re not waiting for perfect. They’re pushing things live, learning, improving.
They know speed beats perfection and that perfection’s an illusion anyway.

6. Pure focus
They’re not chasing shiny objects or riding trends.
They know exactly what they’re building. And they stay locked in.
Every yes is thoughtful. Every no has purpose.

7. No bias
They don’t care where you’re from, what you sound like, or what box you fit in.
They care about clarity. Good ideas. Clean execution.
That’s it.

8. Solution-focused
They don’t spiral when things get messy.
They adapt. They reframe. They get back to building.
They play the game as it is, not how they wish it was.

9. High-trust operators
They hire people they believe in and let them lead.
No micromanaging. No second-guessing every pixel.
Just trust, accountability, and momentum.

10. Always learning
The best ones? Still learning. Still listening.
Even when they’ve got the money, traction, press - they’re still curious.
That mindset? Rare. And magnetic.

Writing this list was a reminder.
To focus my energy where it counts.
To build with the right people.
To say no more often - and hell yes when it feels right.

Because the older I get, the more I realise:
The people you work with shape everything.
Your energy. Your growth. Your joy.

Choose wisely.

♡