What I Learned From Hiring My First Employee

Diane Prince
4 min readJun 12, 2021

And the beginning of my entrepreneurial journey

This story is for entrepreneurs who want to scale their business but are feeling stuck in being overwhelmed by doing everything themselves. I share from my own experiences of building companies for over 25 years, including building a $50 million business and selling it to a public company.

This is about my first employee and what I learned.

In the beginning

I hired my first employee when I was 27 years old. I’d quit my job a few months prior, set up office in a rental home in Pasadena. My then husband quit his job a few weeks later. We borrowed $35,000 from my family and we went all in.

We started a staffing agency that placed title searchers and examiners and we had only surface knowledge of both staffing and title insurance. For the first few months, we stayed close to our super tight niche, but our clients consistently asked us to expand. They wanted us to find them escrow assistants and officers too — those were closely related roles to the ones we were already filling, but they were still out of our scope of business.

Our first employee was at least 30 years older than us. We hired her because she had the experience that was needed for that role. She had expertise in placing escrow people and we did not. She had connections, she was all about business, and we liked her. We hired her away from a competing agency.

For those looking to hire their first employee

A lot of startups today want to hire people for free. They offer equity in exchange for work. Founders want to find other people who are equally as passionate about their vision who will work for the chance that the company will be a success. I’m not saying that doesn’t work sometimes. Sometimes it does, but 80–90% of the time the company fails and the people on the team are left with nothing but the experience.

Not only that, it’s all fine when business is good and everyone’s excited. But vague agreements, shady payment terms, and employee misclassification can turn into expensive and stressful legal battles when companies go under.

Back when “startups” and “entrepreneurs” weren’t a thing like they are today, we…

Diane Prince

I built an 8 figure business and sold it to a public company. Now I coach startups through their growth pains so they can scale successfully too