Connor Gillivan


Connor Gillivan is the CMO and co-founder of FreeeUp, the hands-on online hiring marketplace connecting hundreds of businesses with reliable, pre-vetted remote workers. Connor is a 29-year-old serial eCommerce entrepreneur. From his experiences bootstrapping multi-million dollar businesses since his college days, he has written Free Up Your Business: 50 Secrets to Bootstrap Million Dollar Companies, and become an expert at online hiring. With his first eCommerce business – where he sold over $20 million worth of product – he managed over 60 freelance workers.

Connor Gillivan now leads FreeeUp’s marketing efforts from his home in Denver, Colorado. Connor is the man behind the scenes at FreeeUp. You won’t always see him on the front lines, but that’s because he’s heading off the silent engine that drives this fast-growing hiring marketplace. He balances this focal area and his other businesses, his personal mentoring website,, and several other endeavors, including sharing business advice in top publications.

So who is FreeeUp’s Connor Gillivan, really?

I interviewed Connor to get deeper into what drives him as an entrepreneur, specifically with regard to his involvement with the online marketplace. I was excited and awed by what I learned.

1.  Connor, what first interested you in entrepreneurship and drove you to pursue this lifestyle?

I was first introduced to entrepreneurship by my older cousin. My first job was working for him in the landscaping business that he had built from the ground up. I worked with him for over 8 years as I went through high school and college. During that time, I learned the ins and outs of the landscaping business.

I saw how he was able to build a stable life and income for himself without depending on anyone else. I absolutely loved the freedom and security that it offered – something that does not often come together in the working world. I was also intrigued by the idea that my future and success were dependent upon my hard work and efforts, and not someone else’s whims.

So, from a young age, I was hooked into the idea of being an entrepreneur and living that kind of liberating and invigorating lifestyle.

2.  Who most influenced your journey and prepared you for a life of building and running businesses?

My parents were an amazing influence on me as I grew up. They were always there for me as I figured out my path towards entrepreneurship. They were both extremely supportive in any decision that I made, as long as I was making sure that my education always came first.

After graduating from college, they really trusted me to chase the entrepreneurial path. That trust was a very important factor in my confidence to succeed. My parents also never pushed me towards any particular profession or type of work life, and I really appreciate that. I think that this allowed me to experiment without worrying about taking my own risks or experiencing that duality about which path was right for me.

3.  How did the idea of FreeeUp play into your goals as a social entrepreneur?

During my college days, I spent a summer in rural South Africa on a 3-month internship focused on social entrepreneurship. I was always interested in building a business that made a positive impact on the people using the product or service. But this was a life-changing experience that opened my eyes to implementing working solutions to real world problems.

After graduating from Quinnipiac University in Florida, I returned to run the same internship program. With over 30 people and a good budget, I was determined to make a difference and help others experience the growth that I had enjoyed there. Many of the core beliefs that I now have about myself and that I apply as an entrepreneur and a leader come from these experiences.

So when my business partner, Nathan, and I came up with the idea of FreeeUp, it was something that I was immediately attracted to. The idea of FreeeUp allowed me to tap into that passion for meaningful impact. We conceptualized a business that would give freelancers and clients a better place to build their online companies by working with each other. We felt strongly that the mutually beneficial synergy that we envisioned was a great solution to a very real and difficult pain point for both sides.

As FreeeUp has grown over the past two years, it has been amazing to see the impact that the marketplace has had on thousands of freelancers and business owners. It means a lot when we get stories from freelancers and clients thanking us for creating the platform and telling us about how it has allowed them to change their lives. For me, having that impact is priceless, and nothing can compare to it.

4.  What about FreeeUp impassions you?

I love the work that I do with FreeeUp for many reasons.

First, it always challenges me to learn new things and become a strong overall entrepreneur. I chase opportunities where I can grow and learn from my mistakes. Being the CMO of FreeeUp allows me to do that every single day.

Second, the impact that we are able to make on the freelancers and clients that use the platform is tremendous. Knowing that I wake up every day to help someone grow their business keeps me constantly motivated.

Third, I’ve found an extremely diverse and rapidly growing industry where I can stay on the cutting edge of what is happening. I am in a position to shape the trajectory of the industry towards more positive outcomes for everyone involved. Running FreeeUp is a genuine dream come true for me as an entrepreneur.

5.  How do you realize your goals through FreeeUp as it is now?

I love running a business because things are always changing and there is always something that you can make better. I work extremely closely with my business partner and our CEO, Nate Hirsch, to set realistic yet challenging goals for FreeeUp each year.

As we make it through each month and quarter, we reflect on progress, celebrate the small victories, and find ways to improve. Both Nate and I are always on a hunt to constantly improve the business and experience for freelancers and clients. Running any business is a marathon, and building this marketplace on the basis of having that positive impact on people’s daily walks is life-long trust.

Who is the personality behind your business?

Answer for yourself the above questions and learn – or re discover – what drives the core of your business. Knowing this is a powerful realization that can shape your future success.

Are you inspired by the passion behind the FreeeUp marketplace?

Become a client today and begin to reap the benefits of hiring through a marketplace that has your growth at the core of its goals.


Julia Valdez

Julia Valdez is a professional teacher and decades-long lover of the art of words on paper, the stage and the big screen. She spends most of her time doing freelance content and project management, community volunteer work with the Philippine Advocates for Resilient Communities, adventuring with the Greenhouse Christian Fellowship, and sharing lots of laughs over little crazy things.


Free Up Your Business with FreeeUp

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