Building Company Culture: Crew vs. Contractors

When I think about what really makes a company thrive, it all comes back to one thing—company culture. Over the years, I’ve hired both 1099 contractors and W2 employees, and while each has its place, the biggest difference I’ve seen is in how company culture develops depending on which path you choose.

I learned this lesson the hard way during something as simple as a moving experience. One moving company sent a random group of contractors to my house. They didn’t know each other, they didn’t communicate well, and they eventually ended up fighting in my living room. Things got broken, the move dragged on for hours, and I swore I’d never use them again.

The next time, I hired a moving company that used the same crew every time. They worked together daily, communicated clearly, and got the job done in half the time without breaking a thing. That’s when it hit me—this is what a true company culture looks like. A team that trains together, solves problems together, and knows how to move in the same direction.

As entrepreneurs, we often look at the short-term savings of contractors. They’re cheaper, easier to let go, and come with less red tape. But if you want to build something that lasts—a business with a mission, a vision, and a team that truly buys in—you need W2 employees. That’s how you create a culture, not just a collection of workers.

At PT Biz, we’ve found the sweet spot by using both. Contractors make incredible coaches because they bring entrepreneurial energy and expertise. But for the core of our company—the team that drives strategy, culture, and long-term growth—we rely on W2 employees. That’s where the real depth of leadership and company culture happens.

And here’s the part that I’ve had to grow into as a leader: you can’t build a strong company culture if you’re always jumping in to do things yourself. I’ve had to resist that urge and instead let the team figure things out, even if it takes longer. Because leadership isn’t about doing the work for them—it’s about creating an environment where they can succeed, grow, and take ownership.

So if you’re trying to decide between contractors and employees, ask yourself: Do you want a group of individuals who show up to get paid, or do you want a crew that builds something together? That choice will define the company culture you create.

Show Notes

00:30 – Why company culture depends on your hiring decisions.
02:15 – The moving company story: contractors vs. crews.
05:00 – How W2 employees shape stronger company culture.
07:40 – The short-term savings and long-term costs of 1099 contractors.
10:25 – Why we use both contractors and employees at PT Biz.
13:00 – How leadership style impacts company culture.
15:10 – Building a crew you want to lead, not just manage.
16:40 – Final thoughts on creating a lasting culture.