Connor Gillivan, 7-figure Amazon drop-ship seller AND author of ‘Free Up Your Business’ (episode 102)

Connor Gillivan built a seven-figure business trading dropship items on Amazon before founding Freeeup, where you can find over 400 vetted freelancers to outsource your technical and time-consuming eCommerce tasks. Connor also just published a book called Free Up Your Business: 50 Secrets to Bootstrap Million Dollar Companies, which is packed with great tips and advice from Connor’s years of experience.

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Getting Started

Connor was studying in college when he met his current business partner in a business law class. His partner was purchasing textbooks from students who were unhappy with the payment they would receive from the school bookstore and selling those textbooks on Amazon Marketplace. He asked Connor if he’d like to join, and Connor accepted. As Amazon expanded into more categories, the two of them expanded as well, forming an Amazon store called Portlight.


As Portlight expanded into more categories, they built over a thousand dropship relationships with manufacturers around the United States, eventually building up to around 500 thousand products through the Amazon store. They would form relationships with manufacturers who were making their own products but lacked the expertise to sell on Amazon, strategically seeking out retailers who were utilizing the dropship business model and going after the manufacturers those retailers were working with.

Listen to learn more about the mutualistic relationships between Portlight and manufacturers.

One challenge was how to deal with manufacturers who made a best-selling item but were bad at customer service. Portlight would have conversations with those manufacturers and try to build a better relationship with them, and if the manufacturer could not handle the customer service, Portlight could take it over.

Another challenge was transferring product data from the manufacturer’s files to Portlight’s files.

Listen to learn how the data transfers were completed.


The experience of training and managing people for Portlight was a trigger in creating Freeeup. The Portlight team had hired about thirty freelancers from online hiring platforms, but had some bad experiences due to their desire to hire people quickly, at lower rates, and without proper vetting. It was frustrating to post a job, recruit for it, interview for it, and hire someone, only to find a couple weeks later that they hadn’t hired someone who was a good fit.

Over the years, the Portlight team came up with their own formula for properly vetting their workers, then thought that other eCommerce companies may be going through the same troubles. They wanted to create a better solution, where people didn’t have to spend their time recruiting, interviewing, and vetting, where they could simply go to a site where others with eCommerce backgrounds and skills were already pre-vetted and ready to start working. Freeeup snowballed from there. Customers come to the site and fill out a worker request form specifying everything they want in their freelancer, which Freeeup then uses to find the best match.

Listen to learn about the four main categories with 45 different skillsets that you can find at Freeeup.

You can save $1 per hour with our special MasterPlan World Freeeup deal – find it here

Passion for Sharing Knowledge

Connor’s passion for sharing his knowledge with others to help them build their businesses or lead more meaningful lives convinced him to write a book. He’s been writing for about ten years and publishing his writings on his own website for about two, but he and his business owner wanted to bring together all of the lessons they’d learned from building the businesses and offering it as an additional resource.

Listen to learn which of the six main tips in the book Connor thinks is the most important, and which one most entrepreneurs fail at.

Trial and Error

Connor believes entrepreneurs should always be looking for opportunities to do trial and error and figure out which is working best. He recommends creating a hypothesis, testing it, and gaining feedback from customers. Iterate off of the original test, and repeat.

Listen to learn how Connor’s trial and error approach has helped him in the past.

eCommerce Book Top Tip

eCommerce Traffic Top Tip

  • Referral programs or affiliate programs

You can hear about all this on the podcast, for free – right now…

Tool Top Tip

  • Skype
  • Wisestamp

Start Up Top Tip

  • Find the right niche

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