Your First 5 Hires Will Make or Break You

Howdy! In today’s blog, I want to talk about one of the most important and also most overlooked decisions you’ll make as a founder: who you hire first.

The first five people you hire are not just employees. They’re the foundation of your culture, speed, and survival.

Hiring your first five people is nothing like hiring your fiftieth. Every decision gets amplified. Every strength multiplies. And every gap shows fast.

If you get this right, everything that follows will feel a lot easier.

Hire Builders, Not Managers

In the early days, you need people who want to build, not people who want to manage.

I generally suggest avoiding hiring anyone who’s more excited about leading a team than actually solving problems. This stage is about doing the work, wearing multiple hats, and figuring it out together.

🚩 Red Flags to Watch For:

“Who will report to me?”

“When do I get a team?”

“I prefer strategy over execution.”

If they’re already focused on the org chart, they’re probably not ready for the startup trenches.

Prioritize Versatile Skill Sets

Early hires should be multi-tools, not specialists.

Look for people who can operate across disciplines. The engineer who knows a little UX. The marketer who can write, run ads, and build landing pages. The operations person who can build systems and manage projects.

If someone needs a narrowly defined role or hyper-specific lane to be effective, they’re not what you need at this point.

Culture Fit > Resume

At this stage, culture isn’t a buzzword; it’s your entire operating system.

It’s how you move fast, make decisions, and handle chaos that matters. Where they’ve worked before doesn’t matter; what matters is how they’ll work with you now.

I’ve hired people with impressive resumes who just weren’t ready for early-stage chaos. They were sharp, polished, and professional, but these hires needed so much more structure than we had to give.

Lesson learned: stage-fit matters more than brand names.

Test for Grit, Not Just IQ

You need people who can figure things out when there’s no playbook.

Ask if they can operate in uncertainty. Can they create clarity for themselves and others?

One of my favorite ways to see this in action is a short project with minimal instruction. See how they self-direct, problem-solve, and communicate. This will tell you almost everything you need to know.

Because at the end of the day, the roles you hire may shift, but the mindset shouldn’t. Look for people who are resourceful, mission-driven, and allergic to excuses.

Important Question to Ask Yourself This Week:

If you had to start over tomorrow, who would you rehire without hesitation—and why?