Entrepreneurs share about hiring their first employee

by | Dec 1, 2020 | Blog

Caroline Lee

Caroline Lee

Co-Founder of CocoSign

There were rather mixed feelings in hiring my first employee, involving confidence, doubts, hope, fear, excitement and uncertainty. It’s a bit overwhelming to feel so many emotions at the same time, being excited about the first progress in expanding the team, doubtful if I could really be a good team leader, and help such a wonderful talent fulfill his biggest potential; hopeful about the company prospect with more talents joining, yet uncertain about where my new business will be heading. CocoSign

Stephen Keighery

Stephen Keighery

Founder of Home Buyer Louisiana

I have built a company to 300 staff which is going to IPO next week, but this week I hired my first employee at my new business. I have hired hundreds of people during my career but it is funny how excited (and nervous) I am about this one. I spent so much longer on the job description as usual and agonized over getting the decision right. There is no margin for error when you are doubling the size of your company with 1 hire. Cultural fit is always important but with an early hire like this you are still establishing the culture and this person is going to have a big impact on it. I also have a sense of excitement about a plan coming together and excited to execute as I have a clear path for the next 3 positions I want to create. Start up phase is so exciting and getting the first hire under my belt is a huge milestone which I am proud to reach. I have been here before though and know I am only at the beginning of this journey and the next step is to help them thrive in the role. Home Buyer Louisiana

Nat Miletic

Nat Miletic

Owner of Clio Websites

In one word, liberating! Before I decided to hire my first employee, I felt like I needed to do it all myself in order to maximize my profits. I quickly realized that this is not a great long term growth strategy since I am in the services industry. In order to grow and expand, I would either have to work an insane amount of hours, or let someone else do the work and make a little bit less money. In the IT services business, hiring others and outsourcing is the only way to scale and grow. When I hired my first employee, I felt way more liberated and free to focus on growing my businesses, instead of doing all the work myself. I would recommend this approach to anyone who is looking to scale and grow their business. Clio Websites

Brian Robben

Brian Robben

CEO of Robben Media

Hiring my first employee felt like a mix of joy and fear. Joy that I could partner with another talented individual to drive business growth and service clients. Fear that now I really had to perform, sell, and make money because someone else’s livelihood depended on it. Fortunately, I rose to the occasion and sold some new clients to get the fear monkey off my back. Growing a business, including when you hire your first employee, takes getting outside your comfort zone for a greater future. Robben Media

Chris Norris

Chris Norris

Managing Editor of Sleep Standards

As a business owner, going through the process of hiring my first employee felt exhilarating, like taking the first step when setting out on an adventure. Although it signaled the end of the planning phase, it was the spark of the next one. There was an amalgam of emotion: the fear of uncertainty and thrill of unlimited possibilities. It brought the feeling of growth as a company, and carried a sense of completion as the business strategy came into fruition. Sleep Standards

Shayla Dempsey

Shayla Dempsey

Owner of Four19 Properties

When I hired my first employee, I was more nervous than she was. Although I had run my own company for years, the idea of someone coming onboard was intimidating. The way I ran my day to day operations made complete sense to me in my organized chaos but to let someone in to see behind the curtain was a bit nerve wracking. Four19 Properties

Michael Fenech

Michael Fenech

CEO of VoiceByte

Hiring my first employee was really exciting but at the same time, daunting. I soon realised that my every move was going to be responsible for putting food on my employee’s table. I felt a tremendous obligation to do the best possible job I can to ensure we succeeded as a company to keep my employee in a job. I used the fear of failing as the fuel to drive me towards success, and it was all centred around maintaining the money flowing into my employee’s bank. It’s funny, but I never knew this line of thinking would have ever come into my mind, but when the realisation of my responsibility hit, this is what went through my mind. I must admit, these thought processes did calm down, but it was undoubtedly a good shot in the arm to make sure I perform! VoiceByte

Andrew Cabasso

Andrew Cabasso

Founder of Postaga

Hiring my first employee was simultaneously exciting and terrifying. It was exciting because it was a milestone. It meant that my company was growing enough that my partner and I couldn’t do everything ourselves anymore; it meant that we needed help to be able to handle our workload, and ultimately help us take the business to new heights. It was terrifying because I had never hired an employee before. Since I never hired anyone before, I didn’t know whether the person I hired would be the right person for the job just based on our interview. I was worried because I knew that it would take time to train this new hire, and that for awhile it would cost us time and money to be able to get them up-to-speed. If it didn’t work out with the new hire, it would have been a costly lesson for us. But, if it did work out (and, spoiler, it did work out well in the end), we could achieve so much more. Having another team member meant that we would have more manpower dedicated to helping us grow the business, and it would be more than my partner and I could do alone. Postaga

Scot Chrisman

Scot Chrisman

CEO of The Media House

As a business owner, I can say that the feeling of hiring my very first employees was so surreal. I have this mixed emotions of nervousness, anxiousness and excitement all in one and I don’t know how to contain it but I still hired one anyway. I was nervous and scared during that time because a lot of questions are running on my mind, like “Can he really help me?”, “Can I give him his salary and benefits that I promised?” “Can we succeed in this business together?” and other thoughts that hinders me from enjoying the moment. But luckily, through our combined efforts we are still working together as of today, and we are continuously doing our best together with our other colleagues to run the operations continuously and smoothly. The Media House

Lindsey Wander

Lindsey Wander

CEO of WorldWise Tutoring

For the first three years of my business, I was working with students 60-70 hours a week and was turning away referred new clients simply because I did not have the time in my schedule. A conversation with my college friend made me realize I needed to hire tutors. She said, “The first one you hire will be the hardest. Then you will wonder why you didn’t do it sooner.” She was so right! Initially, I struggled with how to hire someone: the process, legalities, and precautions. Once I got the logistics sorted, I struggled with finding the right person and entrusting them with my students. Over time, the positive reviews and elevated student scores built my trust. Now I consider it one of my superpowers to seek out and inspire incredible instructors. I have found myself in the unique position of teaching the teachers, sharing my methodologies to educators passionate about my company’s mission. So, while the first was the hardest, I am glad I took that leap that got me where I am today: helping thousands of children all over the world to grow into confident and independent lifelong learners. WorldWise Tutoring

Jacob Sapochnick

Jacob Sapochnick

Founder of Law Offices of Jacob J. Sapochnick

As an entrepreneur, nothing beats the feeling of hiring your own first employee. After planning all the things about your business, you got someone to share your passion with and he/she will be somehow your business partner and you want him/her to be as dedicated as you. You’re excited to teach all the things that they need to learn in order to ensure your success. As a business owner myself, I will never forget the feeling of hiring my first employee. When I hired my first employee, I was full of excitement because this will be the start of growing my business. It didn’t feel like I was working with my own employee, it just felt like I was working with a colleague and I shared all the ideas that I want to implement soon. As I’ve said earlier, I treated him not as an employee but as a business partner. Law Offices of Jacob J. Sapochnick

Ryan Naylor

Ryan Naylor

CEO of VIVAHR

Hiring my first employee felt absolutely valuable and was a great indication that I was moving in the right direction for the growth of my business. Of course, it was a bit nerve-racking and I had a lot of expectations but I knew that in order to have a successful employee and boss relationship, I had to set the tone. I had a general idea of the goals they would achieving for my business; however, I knew that I would need to be a mentor and provide feedback to support this person for the overall growth of my business. I knew from the beginning of hiring my first employee that every responsibility, task, and expectation that I gave to this individual was eventually creating my company’s culture. As an entrepreneur, I believe strongly that this aspect of building a notable company culture is a vital part of running and growing a business successfully. What I have learned from hiring my first employee to my most recent, is that finding the ideal employee all starts with me being an exceptional leader and presenting a position that is more than just a place to receive compensation. VIVAHR

Valerie Smith

Valerie Smith

Founder & CEO of Klei Beauty

I hired my first employee in May 2020. Maire started with Klei as a paid marketing intern, and I knew after working with her for a few months that I needed her on my team as the first-ever Klei employee. Once she graduated from college, I offered her a position as my marketing assistant. It felt exciting to hire her, like I was investing in not only my company’s future, but hers, too. Klei Beauty

About the Community

On the podcast, Sean talks with entrepreneurs about the reality of their struggle to succeed, as well as answering questions from the community, and sharing nuggets of wisdom from his own life.


Discover through these amazing episodes the courage to open your mind, heart, and soul to the world so you can be the best entrepreneur possible, respect the people you work with, and improve the world with your company while not hurting others or yourself in the process.

Sean Weisbrot

Sean Weisbrot

Sean is an entrepreneur, investor, and advisor based in SE Asia for over 12 years. He is passionate about Psychology and helping others improve themselves.

Sign-up for the FREE
How to Start Meditating guide

Discover the answers to these questions and more:

  1. What is meditation and how can it help me?
  2. What are the kinds of meditation and which is the best for me?
  3. How can I start right now and build up my technique?

Share This