Our Story

How We Went From Zero Help to Working With 100s of VAs

Through years of trial and error building different businesses, we’ve developed a proven system for scaling with virtual teams. Read our story below and reach out to connect!

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Our Story


The Early Amazon Years

Outsource School’s founders, Nathan Hirsch and Connor Gillivan, started working together back in 2009. Their first business was in the eCommerce industry helping brands to sell their products on Amazon and they scaled it to $25 million in total sales over 5 years of scaling. 

What they quickly realized though was that they couldn’t do it all on their own…they needed to hire to scale faster…so they turned to hiring from websites like Odesk (now Upwork) and Fiverr.




Frustrations With Hiring

For years, Nathan and Connor hired and fired hundreds of virtual assistants and freelancers from Upwork for their first business. 

And they ran into every obstacle in the book…disappearing assistants, being overcharged for work, empty promises…you name it and they experienced it.

The key problem: they didn’t have a proven hiring system and they had to create their own from scratch. 



Founding FreeUp

Once Nathan and Connor finally figured out a proven method for hiring and scaling with a virtual team, they decided it was time to build a better solution to the Upworks and Fiverrs of the world and they founded the FreeUp Marketplace. 

For 4 years, Nathan and Connor scaled FreeUp from an initial $5,000 investment to $12 million in yearly sales with a team of 35+ virtual assistants. No US office and no US employees. 




Getting Acquired

In 2019, Nathan and Connor were approached by a FreeUp client, The HOTH, expressing interest in acquiring FreeUp. 

After months of careful consideration and making sure that their team would be properly taken care of, FreeUp was acquired by The HOTH freeing them up to work on other ventures.



Founding Outsource School

After fully transitioning out of FreeUp, Nathan and Connor reflected and started to think of new ways they could benefit other business owners looking to scale a virtual business. 

They thought back to the days when they were struggling to find virtual talent and couldn’t find any solutions online. 

They decided that there had to be a better way. There had to be a leading source of education online teaching business owners how to quickly and efficiently hire, onboard, train, manage, and scale with virtual assistants and freelancers. 

That desire led to the founding of Outsource School and the rest is history.



Our Mission

We spent years hiring from sites like Upwork and Fiverr, but we always ran into frustrations and we didn’t have the right hiring systems.

After scaling our last business, FreeUp.net, to an eventual exit with a team of 35+ virtual assistants, we decided it was time we helped other businesses do the same. 

We’re on a mission to make hiring and running a virtual team simpler, more systemized, and turnkey…while also giving back 3% of all sales to the Teach for the Philippines organization. 

The Outsource School Team


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