Running a business with people you've never met

I’ve never met my business partner. I’ve never met two others who work for me. And chances are, the next time I bring new people on board, I will never meet them face to face.

In the year since I founded Scott’s Cheap Flights, an email subscription service that alerts users anytime exceptionally cheap fares pop up, and grown the team to four people, none of us have ever been within a thousand miles of one another, much less the same office. And in my opinion, the team is stronger for it. 

I founded the business working in a Colorado coffeeshop. Not long after launching, an aspiring entrepreneur Brian, an American who lives in southeast Asia, emailed me to see if I would do an interview for his travel blog. I said yes, we chatted for an hour, he posted the interview, and I figured that was the last we’d hear from each other.

A couple months later, Scott’s Cheap Flights began growing exponentially and I realised that it needed a second pair of hands. I sent Brian a quick inquiry. I’d read back through his work, and his enthusiasm for joining a start-up on the ground floor and helping it grow was apparent. We had a getting-to-know-each-other phone call where I explained the nuts-and-bolts of Scott’s Cheap Flights and he pitched some ideas for improvement. We agreed on terms and he started the next day.

Bringing on a business partner who I didn’t know and had never met was undoubtedly a risky move. But dawdling and letting myself get mired in a months-long search for a business partner had its own risks, with no guarantee of success.

As the business grew from a manageable number of subscribers to over 100,000, we put for-hire posts up on Reddit to scout out new talent. Dozens and dozens of applications later, Brian and I settled on Cassandra, who lives in Canada, to head up customer support and other behind-the-scenes aspects of the business, and Nicole from Sydney to expand Scott’s Cheap Flights into Australia and New Zealand.

When I tell people that the business is comprised of four people living in four countries who have never met each other and perhaps never will, many are in disbelief. After all, office culture is well-ingrained in our collective sense of what work is supposed to look like.

But what many see as a bug, I see as a feature.

Brian, Cassandra, and Nicole have been invaluable members of the team, but I only found them because I set aside the notion that prospective applicants had to live near me. Though none of us are in the same room, we’ve made it work by establishing expectations of accessibility and utilising an array of different online tools to optimise productivity.

First, my management style focuses on outcomes, not hours put in. It doesn’t matter to me how many hours each person works on any given day so long as they get done what they need to get done. In addition, our roles within the business are fairly distinct, so each person can get most of their work done on their own without much need for collaboration.

Of course there are times when we need to discuss something. For minor issues, we reach out to one another over Gchat or email. In rare instances that there’s a pressing matter, every team member is accessible on fairly short notice, whether through text message, Google Hangouts, or WhatsApp. And when Brian and I just want to chew over random ideas, we know that we’ve got a few hours where our waking hours overlap every morning and evening.

We also take advantage of various online collaboration tools. Rather than emailing documents back and forth, we use Google Docs and Google Spreadsheets. Instead of morning meetings, we keep up on what everyone’s working on through Asana.

Though we’ve had success, businesses built on all-remote workers wouldn’t work for every start-up. Differing schedules, slower communication, and less collaborative teamwork would be a death knell for many businesses. 

But for us, working remotely from one another has been an unadulterated success. We can bring the most talented people onboard, rather than people who just happen to live within 30 miles of me. We don’t have to pay for an office and all the associated overhead costs. We get to set our own schedules and run errands during the day when shops are empty. We can work from anywhere (Brian has already moved cities three times since joining the team). And because we don’t have an office we’re expected to be in until 5pm, we don’t have to pretend to work if we’ve finished everything we need to do by 3pm.

It’s not that I don’t want to meet Brian, Cassandra, and Nicole. But the fact is that if I only hired people I could meet, I never could have hired them, and Scott’s Cheap Flights wouldn’t be half the business it is today.

This is a guest blog and may not represent the views of Please see for more details. Thumbnail from gettyimages.


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