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How to Survive as a Bi-Coastal Entrepreneur

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Whether it’s for setting up offices in new cities, doing the Sand Hill Road fundraising circuit or closing enterprise deals, you may find yourself joining the bi-coastal club unexpectedly. It isn't an easy club to join, as it can be even more challenging to get your startup off the ground and manage a team from a distance while not exactly feeling 100 percent at home in a new location.

As CEO of Boxbee, a valet storage company, I’ve been tasked with expanding our on-demand storage service offering city by city, starting with San Francisco, followed by New York and other locations. The presence of teams in multiple cities meant I needed to be splitting my time almost equally on opposite coasts. Even with my nomadic upbringing of having moved 22 times, this was initially a lot to handle. After doing this for over a year I started to develop a talent for it. I learned all the secret tips and handshakes and found ways for my team to develop seamless communication across geographies.

Here is how to make the bi-coastal lifestyle a little easier:

Related: 8 Ways for the Entrepreneurial Road Warrior to Travel Smarter

Travel comfortably.

It all starts with your travel plans. Traveling can be a great way to enjoy disconnected solitude for a few hours. With the roaring engines blocking out many distractions at 30,000 feet, I often achieve my best focus and brainstorming sessions while traveling. However, nothing is worse than an uncomfortable or poorly scheduled flight. Try flying on JetBlue, which was just found to the most comfortable airline according to Airfarewatchdog. Or use websites like Seatguru, which memorize which seats that yield the longest legroom so that you arrive on the other coast ready to do business.

Make yourself at home.

The next trick to managing a bi-coastal lifestyle is to try and feel at home in the subsequent city you are traveling to. By consistently staying in only one or two different places, you’ll begin to make those spaces feel like a second home. For short stays, use the HotelTonight app to choose between a small selection of nice but deeply discounted hotels.

If your team tends to toggle back and forth between the two cities it would be a good idea to rent apartments in each city. When the apartments aren’t in use, rent them out using services like Airbnb to almost completely subsidize the cost.

For more budget-conscious travelers, use TripIt to track when you and your friends are in and out of town and stay at your friend’s when they’re away.

Related: 10 Apps to Save You Time, Money and Energy on Your Next Business Trip

Familiarize yourself with your surroundings.

Once you’ve picked a spot to call home for a few days or weeks, it’s time to really make yourself feel at home. Get to know your new city and find local hotspots by using apps like Yelp or websites like Eater to discover where you should be dinning.

If you need to prepare for your next business meeting and are in need of clean clothes, try services like, which will come by to inexpensively pick up, wash and deliver your clothes for you.

Keep in touch.

A successful bi-coastal arrangement is just as much about the team and communication structure as it is about your travel system. While you’re away, stay in contact with all of your employees with tools like Slack, Asana, and Google Apps, and minimize email usage where possible. It’s a non-invasive way to take a virtual pulse on what’s going on with different members of the team.

Video chat is another great way to stay in touch with your “distant” team members. The more you can shorten the distance between teams, the lower the friction, and the higher the efficiency of communication.

It’s also important to keep morale up and your company’s culture relevant, even while you’re away. Sending unexpected gifts or kudos for a job well done will let your team know you are still present and you don’t take their work for granted. 

Lastly, be consistent about the timing of your bi-coastal trip. If you plan on being in the other city one week out of the month, make sure it is the same week each month. This will help promote efficiency around scheduling and getting things done during this period of time.

Related: Traveling for Business? Consider Packing These Healthy Tips.

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