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Jan 24, 2019

On today’s episode of Just the Tips, I welcome a new and improved Dean Holland. He hasn’t actually changed a thing, but I’m trying to spice things up a bit. And Dean and I together welcome Nathan Hirsch. Nathan started his first eCommerce business out of his college dorm room and has sold over $30 million online, and is now the co-founder and CEO of, a marketplace that connects businesses with pre-vetted freelancers in eCommerce, digital marketing, and much more. We talk with Nathan about how he started FreeeUp, the pitfalls of hiring freelancers, and how his first business nearly put his college bookstore out of business.

From cease and desist to rise and persist

Nathan told us a great story on this week’s Just the Tips of how, when he was in college, he began selling books out of his dorm room and the trunk of his car, until the school sent him a cease and desist letter. But by then he had set his eyes on bigger pies, and he began selling products on Amazon. He tried to move beyond books, but no matter what he tried to sell, he kept failing, until at the age of 20, he sold the one thing that all 20-year-old, male college students think about: baby products. But it all took off for him, and taught him hard lessons about selling online.

The number-one problem for entrepreneurs: That first hire

When Nathan was in college as a business major, he remembers one talk by the woman who led his school’s entrepreneurship program. While all of the business professors were telling him to take economics or finance, she just got onstage and said, “If you want true financial freedom, be an entrepreneur.” And from there he was hooked. But I had to ask him, what was the one lesson he’s really learned out in the field that they never taught him in college. And sure enough: It was hiring. Luckily, there’s no one better to talk to about hiring than Nathan, and that’s why we got him on this week’s Just the Tips.

How Nathan made his best and worst hire

Nathan told us about how when he first started his business, the only people he knew he could hire were college students; not exactly the most reliable pool of workers. His first hire was a buddy in his business law class, and that ended up being his best hire ever. But it also gave him the false impression that hiring was easy. So he then made bad hire after bad hire, not really understanding what was going wrong. It took him years to figure it out, and that process is what led to

FreeeUp and solving the problem of freelancers

FreeeUp receives hundreds of freelancer applicants each week to join its marketplace. Nathan’s team interviews and vets them, and takes the top 1% (based on skill, attitude and communication), and makes them available to their clients quickly whenever they need them. It’s a little different than, say, Fiverr, which is an open market. FreeeUp, because it was built by entrepreneurs, is build to solve entrepreneurs’ problems. They have 24/7 support and have a no-turnover guarantee covering replacement costs if the freelancer ever quits. Nathan really has hiring down to a science, and he gives us a ton of great advice on how entrepreneurs can improve their own hiring.

Outline of This Episode

  • [3:45] How Nathan nearly put his college bookstore out of business
  • [8:45] When the entrepreneur seed was planted
  • [11:19] Why Nathan decided he had to hire his first person
  • [14:30] FreeeUp’s model
  • [21:35] How FreeeUp has mastered hiring
  • [23:30] Who uses FreeeUp

Music for “Just The Tips” is titled, “Happy Happy Game Show” by Kevin MacLeod ( Licensed under Creative Commons: By Attribution 3.0 License

Resources Mentioned

Connect With James and Dean

James P. Friel:

Dean Holland: