Why Unicorn Founders Don't Expect Loyalty (And What They Do Instead)

Every now and then, I have similar conversations with different founders.

A top performer just quit.

The founder feels disappointed, angry and scared. They often feel betrayed (“after all the time and energy I put into developing them…”)

Before telling the team, they're terrified of what happens next, convinced that one departure will cascade into a mass exodus. That everyone's secretly unhappy and this resignation will be the spark that sets everything on fire.

I usually ask them the same questions: "What if the story your mind is making up isn't true?" "How might the opposite of your story is just as true?"

The silence on the other end tells me everything. They've been so consumed by their catastrophic narrative – the domino effect, talent drain, team collapse – that they haven't stopped to question whether any of it will actually happen.

Here's what usually happens instead: They tell the team. Most people are fine. Some even step up in surprising ways. The catastrophe that consumed weeks of mental energy and stress never materializes.

But the anger and resentment most founders feel when someone quits reveals a fundamental misunderstanding about loyalty.

You’re Not Entitled To Loyalty

First, let's get something out of the way: You’re not entitled to loyalty. You can't guarantee people will stay.

And honestly, asking "How do I ensure my team stays loyal?" might be backwards, especially when most leaders aren't willing to offer the same loyalty in return.

If times get tough or revenue falls, you'll probably lay people off. So is it reasonable to expect your team to be more loyal to you than you are to them?

I'm not saying layoffs are wrong, sometimes they're necessary. But let's acknowledge what's true: loyalty is a two-way street, and most of us aren't driving both directions.

Here's the better question: "How do I create conditions where people actually want to stay?"

That reframe shifts where you put your energy and attention, which actually increases your chances of keeping your best people.

How to Create Conditions Where People Want to Stay

1. Be Genuinely Generous (Before You Have To)

Here's the pattern I see constantly: Leaders get stingy with appreciation, compensation, and development. Then someone gets a competing offer, and suddenly they're willing to match it.

But by then, it's too late.

People don't stay for the compensation, but they might leave for it. What they really want is to feel valued. And if you're not conveying that every day through your actions and words, scrambling to match a salary offer won't fix the underlying issue.

Be generous with your appreciation before you have to be. Catch people doing things well. Tell them what you noticed and why it mattered. Your direct manager has a bigger influence on your health than your doctor. So if you're someone's manager, be thoughtful about how you make people feel valued.

And this isn't about maintaining assets or tuning engine parts so your machine runs smoothly. Actually care about them as humans. Get to know them. Understand what they want to build in their careers and their lives.

I see leaders close their hearts because they think it'll be easier if they have to fire someone later. Yeah, it'll be easier emotionally. But you'll have lost every day of connection until then. That's a terrible trade-off.

There's this exchange that captures it perfectly: A CEO asks the CFO, "What if we invest in training all our people and then they leave?" The CFO responds, "What if we don't and they stay?"

When you invest in your people's development and growth, you create capacity as a team. And people who feel genuinely invested in tend to want to stay.

2. Don't Tolerate the Wrong People

One of the best things you can do for your top performers is not tolerate low performers or bad culture fits.

I call it the tolerance tax. Every day you keep someone who's not a fit, you're taxing your best people. They see it. They feel it. They get frustrated that they're holding themselves to a high standard while others aren't.

I worked with a founder who hired extraordinary leaders in one division, and those leaders hired extraordinary team members. But in another division, it wasn't happening. The top performers got frustrated: "Wait, we hold ourselves to this standard, but it's not true across the company?"

That's what actually makes people leave.

Most leaders tolerate the wrong people way too long because of their resistance to fear. Scared they can't find better, scared of the confrontation, scared that having someone doing something is better than having the role empty.

Those trade-offs erode culture faster than anything else.

But there's this line I love: "Our most fulfilling lives and relationships are one five-minute sweaty palm conversation away."

Which means, if you can sit with the discomfort for just a conversation, you can protect your culture and ultimately your company.

And here's another truth worth considering: If someone would actually be better off elsewhere, maybe that's okay. What's optimal is people thriving in their roles. If they're not thriving, it's lose-lose for everyone.

3. Paint Futures Worth Living Into

There's a book called The Three Laws of Performance that points out something powerful: People's performance and morale correlate to the future they're living into.

In the quiet of their own thoughts, what do people imagine about the next year?

Do they imagine it being fun, with the company growing and them learning a lot? Or do they imagine frustration, stalling out, just grinding through challenges?

As a leader, one of your core levers is shifting the future your people are living into. Not just a vision statement on the wall, but literally, when they think about next year, what do they see?

In one-on-ones, in team meetings, in all-hands – paint them your brightest vision of the future that they can replace their current one with. Help them see themselves growing, the company thriving, the work being meaningful.

And this connects back to genuinely caring about them: Have conversations about how they want to develop. Then actually make efforts to help them build those skills, ideally by putting them in roles where they get to develop naturally.

Your job isn't just to align people with what the company needs. It's also to align them with what they need and want.

When people feel valued, see a bright future, and are growing in the ways they want, they don't need convincing to stay.

The founders who get this right all realize the same thing:

It was never "How do I keep people from leaving?"

The question was always "Am I creating something people want to be part of?"

Because the teams that stay are the ones being pulled together by something worth building.

They stay because they feel genuinely valued, not just compensated.
They stay because the standards are high for everyone, including the leader.
They stay because when they imagine next year, they see themselves growing, not just grinding.
They stay because they're cared for as humans and not just optimized as resources.

This goes beyond loyalty. People stay because they want to, not because they feel they should. Because you've created conditions where leaving would mean giving up on something they care about.

Build that, and you're doing more than retaining your people. You're developing leaders who transform everything around them.

With love,

- Dave Kashen

P.S. If you find yourself constantly worried about people leaving, ask yourself these three questions: What am I tolerating that I shouldn't be? What appreciation am I withholding? What future am I painting for my team?