TeamOut (YC W22)

I have been fully remote for 10 years, and it’s completely changed my life. And now, as an employer building a fully remote company, I truly don’t understand why so many companies are forcing people back into offices if: - The work can be done remotely - Employees are productive - Companies save on office costs - People are happier Seems like a win-win-win… My team is fully remote and global, we do not have any "fixed" offices. Instead, a few times a year, we bring everyone together somewhere beautiful in the world. Last week, it was Puerto Escondido 🇲🇽. It was our office for the week. We surfed, ate amazing food, laughed a lot, and spent real quality time together. And this week? - The energy is completely different. - Faster decisions. - Better collaboration. - More trust. - More connection. That’s what many leaders still miss: Remote work isn’t about avoiding human connection. It’s about removing unnecessary friction from people’s lives and being intentional about the moments that matter. No traffic. No pointless commuting. More time for family, health, travel, and actually living. Remote work is the best thing that ever happened to me. Not because we work less. Because we live more. Bringing a remote team somewhere beautiful a few times a year is literally what we do at TeamOut.com Who’s with me?

My team is fully remote, and global. We've never had an office. Last week, we flew everyone to Puerto Escondido, Mexico. The weeks leading up to it had been hard. Someone had left. The news cycle was heavy. The team had quietly drifted into pure remote mode, heads down, fewer jokes in the chat. We landed. We surfed. We ate too much. We had a few too many margaritas. Then we came home. And this week is different. The meetings have a pulse. People are jumping in faster. Decisions are landing in hours instead of days. I can feel the ownership, and I can feel how much closer everyone is. Remote-first gave us the freedom: hiring anywhere, working by results, building real lives outside of work. But it's the time we spend in person, once a quarter, that turns that freedom into a team. Five days together can repair what three quiet months can erode. That's the trade. Planning the few days together that hold a remote team up is exactly what we do at TeamOut.com

Manager: I noticed you didn't reply to the emails I sent last night. Employee: I saw them this morning and planned to respond first thing during work hours. Some uncomfortable truths about always on culture. Constant availability is not commitment. Most of the time, it is anxiety wearing a costume. A manager who needs replies at midnight is not building a high performing team. They are building a tired one. The email that feels urgent at 11pm almost never is. Tomorrow morning would have delivered the same outcome 9 times out of 10. The real exceptions are rare, and everyone knows when they hit. Burned out employees do not produce better work. They produce work that looks the same on the surface and slowly gets worse underneath. Tenure beats intensity. A great employee staying 5 years contributes more than three great employees cycling through in 18 months. Respect compounds. Resentment compounds faster. The strongest cultures I have seen are not the ones where everyone is on at all hours. They are the ones where people protect their energy because they know they are in this for the long run. Companies are built over years. Not over weekends.

I have one main rule for my team. As long as you deliver your work on time and to the highest standard, I don't care where you do it from or when you do it. Yesterday, one of our team members worked from a café with his 99-year-old grandfather. He'd shipped 3 deliverables before lunch. Another team member took a 2-hour break to pick up her kids from school. She came back and crushed her afternoon sprint. Someone else worked from a different country entirely last week. Their output? Flawless. Here's what I've learned after years of running a remote-first company: The best work doesn't happen between 9 and 5. It happens when people feel trusted, respected, and free to do their best work on their own terms. My challenge: Stop measuring presence. Start measuring impact. Or keep losing your best people to someone who will. We built TeamOut.com so remote teams can come together for the moments that actually matter — without losing the autonomy that makes them great.

As a Founder, I don't care about: - Which city my team wakes up in - Whether they start at 7am or 10am - If they took a long lunch - How many hours they logged this week I do care

As founders of a remote-first company, my co-founder and I don't have to worry about: - Where our team lives, or... - When our employees work, or... - If they work "40 hours a week" (Honestly, the opposite is usually the problem. We're more often reminding people to take breaks and actually use their PTO.) We don't lose sleep over whether someone steps away to: - take a nap, - visit the barber, - see their doctor, - walk their dog, - grab lunch with a friend... We hired these people because they're exceptional at what they do. We trust them to deliver, in ways that fit their lives. No screen monitoring. No "are you online?" check-ins. We set clear goals and everyone moves toward them. We're intrinsically motivated. We genuinely care about our clients and want every team offsite we plan to be an experience people remember. To stay connected and aligned, we use TeamOut to plan our own retreats. (Obviously.) And when someone's struggling, we don't question their hours. We show up, coach them, and figure it out together.