Interested in starting your own entrepreneurial journey but unsure what to expect? Then read up on our interview with Connor Gillivan, Co-Founder of Outsource School, located in Denver, CO, USA.

What's your business, and who are your customers?

Outsource School is an online membership that teaches business owners how to successfully outsource work to the Philippines. Our ideal customer is an online business owner with yearly revenues of $250,000 to $10M which has too much on their plate. They want to outsource, but they either don't know where to get started or have had poor experiences in the past.

Tell us about yourself

I've been an entrepreneur since 2009. My business partner, Nathan Hirsch, and I met while we were in college. We started our first eCommerce business selling products on Amazon and scaled it to $25 million in total sales over the course of 5 years. While building that business, we outsourced work from sites like Upwork and Fiverr, but we always felt the experience could be better. We'd post a job, get 100+ applicants, and have to sift through them all ourselves. We wanted a better way.

In 2015, we started FreeUp, a freelance marketplace that only lets in the top 1% of applicants and that specializes in the eCommerce industry. For 4 years, we scaled that business to thousands of customers and were acquired in 2019. After selling FreeUp, we realized there was a major need for business owners who wanted to learn to outsource. There weren't many reliable courses online that they could turn to and so we created Outsource School.

Outsource School has helped hundreds of business owners master outsourcing, and I'm excited about its future. Our mission is to help thousands in the next 3 years.

What's your biggest accomplishment as a business owner?

Building businesses and teams that deliver real value to our customers. This is my personal mission in entrepreneurship. Find true problems that people are facing, understand what's currently being offered in the market, and make a better solution for those people. When we can achieve that, and we have a dedicated team behind the mission, it's the best feeling.

What's one of the hardest things that come with being a business owner?

Firing. Letting go of someone from your team is always the hardest thing to do, but it's necessary for businesses to continue growing and moving through different stages of growth. I've had to fire plenty of people throughout my 13 years of being an entrepreneur, and I never enjoy it, but it's a necessity.

What are the top tips you'd give to anyone looking to start, run and grow a business today?

Tip #1: Validate the Market for your Idea: Talk to 100+ potential customers, pitch them your idea, and make sure that there is real interest. It addresses a real need before you start.

Tip #2: Know Your Differentiators: What makes you different from your competition? Know the 3 things that make you different. You will get asked this question by potential customers, and you want to be able to answer intelligently.

Tip #3: Don't Be a Hero: Many times, entrepreneurs try to do it all themselves. They hoard all of the work, leading to burnout and detriment for the business. Don't be a hero. When you're overloaded, turn your work into processes and outsource. Hire the right people for the right seats and delegate. That's the only way to reach scale.

Where can people find you and your business?


If you like what you've read here and have your own story as a solo or small business entrepreneur that you'd like to share, then please answer these interview questions. We'd love to feature your journey on these pages.

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