3 Rookie Mistakes I Made as An Entrepreneur

I started my first company when I was 28 and my second at 34, which recently resulted in a successful exit after five ...

I started my first company when I was 28 and my second at 34, which recently resulted in a successful exit after five and a half years. I became a more experienced business leader from the first to the second.

Did I make mistakes? Yes! Before the pandemic, I believed in hard work and giving it my all, but I also burned bridges, worked myself ragged, and didn't properly invest in my team members.

My companies grew successfully, and my head became swollen with accolades. I felt like I could do it all alone, but each time, things came crashing down on me as I exhausted myself. 

When I founded my second company, House of Revenue®, in 2017, I was determined to set everything right, learn from my past mistakes, and create a company with a solid foundation, strong vision, and values. 

However, I still made mistakes, but that's what makes me human. God gave me the grace to start over as an entrepreneur, and I'm grateful for all my mistakes because they've taught me to be a better person and leader, now as the CRO at PNI•HCM.

Rookie Mistake #1: Not Serving My Team Members

When you can truly appreciate people and serve them first, they will do more than what is expected of them. This thought of serving first was a critical shift for me as a leader during my second business venture. At House of Revenue, our culture was driven by our core values: Serve First, Scale Second, and Succeed Always. 

Through this, I learned to teach my staff to empower themselves in decision-making. I asked them for their opinions and to share possible solutions for each problem they identified. I allowed them to solve problems for themselves first but always let them know that I was available and committed to their well-being.

Commitment includes things like allowing for time off, remote work, professional development, and personal development. It also includes having regular conversations to listen to them and hear about their challenges and celebrations. 

I eventually realized that I only succeeded when my people succeeded. They shined and outperformed all expectations by listening to and meeting their needs. I realized that we could powerfully serve our external clients only when the internal team was strong.

Rookie Mistake #2: Making Assumptions Instead of Agreements

The second mistake I often made was making assumptions based on unrealistic or unspoken expectations instead of agreements. Have you ever had an expectation of someone that they didn't follow through with? If this happens too often and with different people, you need to ask yourself if you are the problem.

For example, I had asked for a report showing the combined marketing and sales funnel. I assumed my staff member would pull data for all outbound and inbound activities, blended conversion rates, etc., because that's how I would do it. I received the report, and it wasn't what I wanted. And then, I was frustrated, and time was lost in redoing the report. It's not that my staff member couldn't do the task, but I wasn't clear on what was needed. 

I've learned to let people know what I need from them and have them repeat it back to me, and in this way, we can all agree on the expectations. Do this, and you will set up your team for success.

Rookie Mistake #3: Trying to Do Everything Myself

The third rookie mistake I made was trying to do everything myself. In school, I was the student who, when assigned to work on a team, would do the work of all my teammates rather than delegate.

When I started my first business, I thought I knew everything and that no one could do things as well as I could. So, I did everyone’s job and it became exhausting and limited me from scaling. I didn’t yet know how to recruit, hire suitable staff, or how to delegate properly. 

By my second business, I learned how to hire brilliant people, but I was still trying to do everything myself - from admin work to client work, networking to pitching - you name it. Eventually, I had to step back from my own company, take time to redefine my boundaries and learn to delegate.

In the beginning, it’s common to think that no one can do the job as well as you can. You conceptualize the idea, know your product and the market, and have the passion to execute your idea. But overextending yourself at the start isn't sustainable in the long run.

Many new entrepreneurs make these rookie mistakes. As an entrepreneur, never be afraid to put yourself out there and make mistakes. But always learn and grow from them. Accepting mistakes and learning from them sets apart a mediocre leader from a great one.