021: Connor Gillivan – From dorm room to $20 million in drop-shipping sales on Amazon.com in just 4 years


In this episode I speak to Connor Gillivan – a 27 year old serial entrepreneur who started his first drop-shipping company out of his dorm room at Quinnipiac University building it to over $20 million of sales on Amazon.com in just 4 years. After becoming an expert at hiring, he co-founded FreeeUp, an online hiring marketplace bringing together the top 1% of freelancers with growing businesses. He is also the owner of ConnorGillivan.com, where he writes about entrepreneurship and eCommerce.

1:25 – Background information on Connor and how he started his first business.

2:33 – How Connor got started in his business with his business partner.

3:44 – Some of the obstacles in their business early on.

5:30 – What motivated Connor to continue on in the business and not give up; whose advice he sought.

7:06 – Being accepting of advice from mentors.

8:09 – Recognizing and cultivating a long-term vision while still being focused on issues at hand.

9:56 – What mentoring advice he would give himself now if he could go back and talk with himself two months into the business.

11:47 – Expanding the business into dropshipping and learning about that side of the industry.

13:29 – Starting a cash-flow positive business versus starting out without any profit.

16:42 – Challenges that still exist in dropshipping and ways to get started.

22:07 – The most effective way Connor has found to test a business and advertise through social media.

23:18 – Background on Connor’s book, Free Up Your Business.

27:20 – Information on Connor’s venture, FreeeUp and improving on the online freelancing marketplace.

30:11 – The pain point that FreeeUp is solving.

31:53 – Approaching growth in his various businesses and applying that to other businesses.

33:50 – Connor’s view on the importance of a financial plan and how to approach changing circumstances.

35:25 – Story from FreeeUp about staying diversified and how that led to growth.

38:24 – What’s next for Connor and he’s looking into diversification to continue growing into different markets.

39:48 – Background on Amazon’s Mechanical Turk service.

40:36 – Connor’s view for his large scale goals.

42:06 – How his entry to e-commerce is comparable to the online hiring industry now and being driven by empowering other people.

Resources and Links Mentioned:

100 Most Popular Jobs to Outsource to Online Workers

Free Up Your Business by Connor Gillivan

Amazon’s Mechanical Turk service