Nathan Hirsch and Connor Gillivan
June 24, 2019

Interview with Nathan and Connor, owners of Freeeup

Thinking of creating your own remote startup? See how Nathan and Connor built a successful and effective remote team from scratch.

How did you get started with remote work?

It was back in 2012 or so when we were building our first eCommerce business. We had just graduated from college, and we were reaching a point in the business where we needed to start bringing on more people to help grow the company. We already had a core team of full-time and part-time team members, and we were looking to expand that team without breaking the bank.

It was around this time that we were introduced to the idea of hiring remotely from another entrepreneur that we had met. He tipped us off to a site called Odesk (now Upwork).

We started posting jobs on the platform and began interviewing. Eventually, we quickly became addicted to building up a team of remote talent from all over the world to help as we continued to scale the business.

After years of hiring remotely with our first business and running into many frustrations, we decided there must be a better way, and we started FreeeUp.

Read 114 answers from other remote workers

What are you working on?

Today, we run full time. FreeeUp is a marketplace connecting virtual assistants, freelancers, and agencies with digital businesses in the eCommerce and marketing spaces.

As I said above, we founded FreeeUp out of frustrations we were having with the other online hiring platforms. We wanted a more reliable way to find top talent remotely.

FreeeUp interviews and vets thousands of freelancers every single week then only allows the top one percent into the network. We take care of the pre-vetting, and interviewing for business owners, saving them time on the front end of the hiring process.

As businesses post jobs, we introduce them to one qualified candidate from the network at a time. Businesses can meet as many freelancers as they need until they’ve found the best one for their work.

On the backend, FreeeUp protects businesses from turnover. In the rare case that a freelancer has to quit, FreeeUp will replace them immediately and cover any applicable replacement costs.

Read 107 answers from other remote workers

What's your typical work routine?

We are both early risers. We like to get up early, get on the same page with our teams, clear our emails and Skype, address any major issues, get planned for the day, then launch into meetings, phone calls, interviews, and projects.

The crazy thing is that we both live on opposite sides of the country in different time zones. I’m in Denver, Colorado. Nate is in Orlando, Florida.

Our days are different in that Nate takes most of the company’s podcast interviews, client calls, sales calls, etc. while I am more focused on behind-the-scenes marketing, content, advertising, and recruitment.

Read 92 answers from other remote workers

How has your routine changed over time?

We’ve both matured a lot over the past eight years of working with one another. I think that our ambitious attitudes and ways of approaching business have rubbed off on each other and taught us how to be most effective working with one another.

When we first started working together on our first business, our work styles were slightly different. Today, I’d say that we are very much on the same page and work to share best practices as we find them in our own daily routines.

Read 22 answers from other remote workers

Do you have a dedicated space to work?

We both have dedicated workspaces within our homes where we regularly work and move around from throughout the day.

We both also enjoy getting out and going for walks while taking phone calls. I also tend to move around to different coffee shops in my local area as well when I need to change up the space and get different inspiration for the day.

Read 93 answers from other remote workers

How do you stay on task?

We both have our own ways of staying organized and keeping the ship moving forward. Given that most of Nate’s time is spent on interviews, recordings, and phone calls, Google Calendar serves as his main tool for keeping his day on task and moving forward.

On my end, I spend more time working on different growth projects within the business.

I plan out my day the night before to make sure that I allocate enough time to each project that I’m working on. I then follow that game plan each day while allowing for some adjustments when needed.

Read 100 answers from other remote workers

What do you like about remote work?

We both love the freedom that it allows. With our first business, we had an office with a staff that we went into every day. While it had its perks, we both really love the independence of working from home, communicating online, and being able to work from anywhere we go.

We also love that we’re not limited to whom we can hire.

With the rapid growth of the freelance economy all over the world, we can tap into talent from all over the world. It’s allowed us to meet some really amazing people and build a completely remote company. We wouldn’t have been able to do that without remote work.

Read 106 answers from other remote workers

What do you not like about remote work?

I think anyone that works remote will say this...sometimes it gets lonely. There are days that we wish we lived closer so that we could get together, brainstorm, and spend the day working together. It’s a different dynamic when together in person rather than on a phone or video call.

Read 103 answers from other remote workers

What tools do you use to stay productive?

Skype, Viber, and Zoom for live chats, phone calls, and video meetings. Trello, Jira, and Notes for project management. Calendly and Google Calendar for scheduling appointments and meetings.

We’ve been working together for 8+ years, so we’ve really figured out the best ways to keep communication strong between ourselves and our entire team even though we’re all located around the world. For us, communication is everything.

Read 108 answers from other remote workers

How do you decide priorities?

Together. Every week, we have multiple phone calls where we go over the highest priority projects within the business. We make sure that one of us is leading the project and that we have other people on the team supporting our efforts.

For FreeeUp, it all really boils down to three things:

  • Get more clients signed up and using the network.
  • Get more qualified freelancers into the marketplace.
  • Continue to improve the overall software experience at all times.

The majority of our projects have a connection to those three core goals. If we can always be focused on those, we believe that we’ll continue to see growth in the long run.

Read 40 answers from other remote workers

Do you have any advice for remote workers?

Communication, communication, communication. Have set methods for providing daily updates, meeting weekly, and staying on the same page with clients.

The more you stress communication upfront, the stronger the relationship could become over the long run.

You could be the best at what you do, but if you can’t communicate, you’ll struggle with remote work.

Read 39 answers from other remote workers

What are the challenges of building a remote team?

Motivation. When you’re in an office, you can be a hands-on leader more easily. You can pop over to people’s desks, hold meetings together, etc. When running a remote team, you can still do all of those things, but it becomes more difficult. That’s why having great communication channels set up is so important.

Skype chat can be the equivalent of stopping by someone’s desk. Just have everyone on your team on Skype when they’re working. Then that check-in is simple as a chat. Schedule weekly meetings where you meet with the entire team and then smaller groups of people. Do it in a Skype group chat or using a tool like Zoom.

The challenges are definitely there, but with today’s digital resources, there’s a solution to all of them. You just need to figure out which ones work best for you and your company.

Read 11 answers from other remote workers

What are the benefits of building a remote team?

There are a variety of benefits to building a remote team:

  • Access to talent from all over the world.
  • The mix of different cultures and mindsets with a common company goal.
  • The ability to hire at different rates depending on the skill level needed and where the person is located.
  • Lower overhead with no need for an office.
  • The ability to travel and work from anywhere as long as you have reliable Internet.

Read 12 answers from other remote workers

What did we forget to ask Nathan Hirsch and Connor Gillivan?

At RemoteHabits we're always trying to improve our interviews, what question should we have asked Nathan Hirsch and Connor Gillivan?


Nathan Hirsch and Connor Gillivan

Nathan Hirsch and Connor Gillivan are the owners of FreeeUp, a rapidly growing freelance marketplace catering to professionals and businesses in the eCommerce and marketing industries. Before founding FreeeUp, Nathan and Connor scaled their first business to over $25M in total sales. The two now run FreeeUp full time 100% remote with 35+ contractors located around the world.

Work remotely? Share your story on RemoteHabits!

Want to be interviewed? If you have a remote position, head over to the interview me page!

Looking for a remote job?

RemoteHabits Jobs has everything you need to find your next great remote work position!

Related Interviews

Interview with Grainne, a professional writer and content marketing manager who works remotely

Grainne's freelance work led to her landing a remote work job—see how she manages distractions and balances her work with and her clients.

Interview with Emma, a freelance marketing consultant

Emma is thriving as a freelance marketing consultant—see her tips on managing client demands & making yourself marketable as a freelancer.

Interview with Paul, a remote product designer who has found his zen

The COVID-19 pandemic drove Paul to embrace remote work. See how he has adapted his routine to this new normal, and the one tool that keeps him organized.

Keep your remote working skills sharp—get notified when we post the next remote work interview! RemoteHabits will help you achieve your remote work goals!