Someone sent me these three question about having a remote team. My answers below.

1. Why do you hire remote workers?

This question strikes me as backwards.

Having an office and requiring every team member to live and commute in the same place is way more costly and hard to justify. It seems to me the burden of proof should be reversed.

Why would you build an on-site team? Do you think the city you’re in has talent superior to every other city combined? Will the best people always want to move there? Will your team work better in a physical office to the tune of (insert amount paid for rent)?

Non-remote workers are very tough for me to justify. Remote workers are just workers. They need no special justification.

2. How have remote workers benefited you?

Allowed me to build two companies. No chance in hell I’d have been able to had I needed on-site workers from day one.

Remote allows me to easily experiment with interns and contractors and see who develops into full-time talent as we grow. It allows me to attract world-class talent at below market wages (because adjusted for quality of life, and cost of living in city they pick, they come out ahead).

It allows me to live in a smaller city that’s ideal for raising my four kids even though it’s not ideal for the talent my company needs.

How many times is the best place to raise four kids also the best place to find startup talent? Probably never. Why compromise on either when you can have both?

3. How do you keep them engaged/interested in the work?

Hire the people who don’t need me to keep them interested.


When you’re remote from day one, this isn’t hard. People know what to expect. You attract those who can handle it.

Many people say that team members will have a hard time focusing or being motivated if not in an office. The dirty little secret is that anyone who would have that struggle as a remote worker is already having that struggle in the office, it’s just going unnoticed because people can see them there and assume they must be working.

The bar and accountability are higher with remote teams. If you don’t reply to a message, it’s easy for people to assume you’re asleep or at the beach. You need to maintain a great reputation by delivering results. In an office if someone pops in to chat and you’re not there they just assume you went to the bathroom. You can get away with more.