The Emotional Sign That You Should Make Your First Hire

I was 23 when I started my first business. My brother was doing freelance web design work and had a few customers who needed website hosting services. I stepped in to help. In months I was cash flow positive, and it wasn’t long before I had thousands of accounts.

When you start a business at the age of 23, there aren’t a lot of other things competing for your time. I didn’t have to spend time with a family or go to class. I could pour myself into the business without limitations, save for physiological needs like eating and sleeping.

That worked when I was young and my business was too. Inevitably, however, my business and I began to grow. With that growth came more business opportunities but less time to pursue them. This was especially true when I acquired another hosting company.

I nearly doubled my accounts, but still had just one customer support representative: Me.

In retrospect, it seems like a given that I would make my first hire after I acquired the second hosting company. At the time, however, I remember being anxious about the decision. And with good reason.

There are universal drawbacks to making your first hire:

  1. Hiring is hard. It requires you to step away from the fast-and-furious pace of productivity that you’re used to as a solo entrepreneur. It demands you articulate what, exactly, you need to delegate on a day-to-day basis. And it means you need to trudge through a thicket of unqualified applicants to find someone who may be just good enough.
  2. Cash flow will decrease. When you work for yourself, every paycheck goes straight to your bank account. Your first hire, however, will take a significant bite out of every paycheck. The hockey stick growth that motivated you when you started the business flatlines. So might your motivation.
  3. You will lose control over operations. The purpose of making your first hire is to delegate responsibility to someone else. But you can’t delegate responsibility without delegating control. After spending years building a business with your own two hands, this is likely the scariest part of making your first hire.

Despite these drawbacks, there was a singular moment when I realized that I had more to lose by taking on an employee than by continuing to grow the business on my own.

When I noticed myself getting angry every time a customer called, I knew it was time to make my first hire.

This was a gradual realization but a startling one nonetheless. I caught myself getting upset with customers almost every time they called to ask a question. I got upset because the answers were usually obvious and I had better things to do with my time than walk them through the solutions.

Compared to the drawbacks of hiring, the drawbacks of frustrated interactions with customers is worse.

According to a study cited in the Atlantic, when we’re angry, we’re more likely to minimize the danger of risks and rely on stereotypes. Another study cited in Harvard Business Review adds that angry people are quick to resort to cognitive shortcuts and blame individuals.

If I had continued to struggle through customer calls alone, I would have been too fixated on stereotypes to try to understand my customers. I would have blamed them for not understanding the service rather than evaluating the service for its ease of use. I would have been so focused on freeing my time in the near term that I would have missed opportunities to learn from customers and improve my business in the long run.

In the end, I hired my first customer support representative four years after starting the web hosting business. While it took us a while to adjust to each other, having Vincent on board helped me improve business to the point of being able to sell it in 2016. I didn’t waste time bringing good people on the board the next time I started a business: I made my first hire for Uscreen within six months of starting the business.

This was my experience, but I’m curious to hear from other entrepreneurs. When did you know it was time to make your first hire?