Your first 5 hires set the tone for the next 50. But what happens after that is where it gets complicated.

Your first 5 are the ones who said yes when the pitch was a Google Doc and the office was a coffee shop. They built the plane while flying it. They wore four hats each and didn't complain about any of them. They are, in every meaningful sense, your co-founders in spirit, even if the cap table doesn't reflect it.

And precisely because of that, this is one of the hardest conversations in building a company.

The skills that take you from 1 to 10 are rarely the skills that take you from 10 to 100. Your first 5, your OGs, your ride-or-dies, very rarely grow at the same pace the company does.

Not because they're not talented, obviously. They clearly are; they built the thing. But because in their heads, you're still the person they sat across from at that coffee shop. They're thinking 1-to-10 when you need them thinking 10-to-100, and they can't always reconcile the shift because to them, you are still mentally in the trenches with them. The company evolved. The relationship didn't. And that gap, left unaddressed, turns into resentment, confusion, or disengagement on both sides.

This is where most founders fumble. They either hold on too long out of loyalty and watch performance and morale erode slowly, or they let go clumsily and lose people who built the foundation they're now standing on. The better move is to start planning for their transitions, kindly, graciously, and early. As soon as you see the restlessness. As soon as the energy shifts. Before it calcifies into frustration. And not all exits look the same.

Some of your OGs deserve a bigger stage than you can offer them right now, so you make warm intros, open doors, be their loudest reference. Some want to build their own thing, so you write them a small check or connect them to the right people. Some would thrive running a smaller, leaner vertical, so you explore co-building that with them.

You design options for them BEFORE they have to design an awkward exit for themselves. It's you saying: I love you. I'm grateful for you. And I want to see you grow, even if it's not with me.

But, and this is important, this has to be real. Not decorative. There's a shadow version of this story that founders need to be honest with themselves about.

The first trap is the self-fulfilling prophecy. If you assume your first 5 won't scale, you stop investing in their growth. You stop giving them the harder assignments, the strategic exposure, the seat at the table when the bigger conversations start happening. You start routing around them instead of through them. You hire senior people above them and call it "bringing in experience." And then when they stagnate, you point at it as proof that you were right. But were you? Or did you just stop watering the plant and then blame it for not growing?

Some of the most consequential careers in tech and business were early employees who did scale spectacularly, but only because someone made a deliberate bet on them doing so. Sheryl Sandberg was not Google's first hire, but the principle holds across the ecosystem: people rise to the altitude you give them access to. Not always. But more often than founders assume.

So before you conclude that your OG has hit their ceiling, ask yourself honestly: did I actually give them a chance to reach a new one? Did I invest in them the way I'd invest in a shiny new VP hire? Or did I write the ending before they had a chance to write a different one?

The second trap is subtler.

Sometimes the OG isn't the one who stopped growing. Sometimes they're the one in the room correctly pointing out that you, the founder, are losing the plot at scale. That the culture is slipping. That the new hires are optimizing for optics over outcomes. That the thing which made the company special at 10 people is being sacrificed for the thing that makes it presentable at 100.

And it is very easy to frame that person as "still thinking small" when what they're actually doing is thinking clearly. "They can't reconcile with our growth" is a convenient story when the alternative is sitting with feedback you don't want to hear. "I'm letting you go because I love you and want you to fly" sounds generous, but sometimes it's a way of saying "I don't want the mirror you're holding up."

Founders: if your OG is pushing back, make sure you're distinguishing between someone who's stuck in the past and someone who's trying to protect what made the past worth building on. Those are not the same thing. One needs a gracious exit. The other needs you to listen.

So here's the full picture:

Your first 5 are sacred. They set the culture, the pace, the DNA. Honor that, always. Some of them will scale with you. Invest in that possibility before you dismiss it. Give them real chances, not performative ones. Some of them won't scale, and that's okay. Plan for their transition with the same intentionality you'd bring to any strategic decision. Design exits that feel like love, not loss.

And some of them will be the ones telling you what you need to hear when no one else will. Don't mistake that for inability to grow. Sometimes the person who's "still thinking 1-to-10" is the only one remembering why you started at 1 in the first place.

Knowing when to let go is just as important as knowing when to retain. But knowing the difference between the two is the actual job.