THE ULTIMATE OFFSITE: This Startup Treats The Entire Office To A Month On The Beach

David Barrett, ExpensifyExpensify CEO David Barrett has approved of this expense.

Photo: Expensify

David Barrett, the cofounder and CEO of Expensify, offshored his entire team in October.That doesn’t mean he replaced them with cheap workers.

Instead, he flew 20 colleagues at the online expense-reporting startup to Thailand for an entire month so they could hang out together on the beach.

He’s been doing this for years, and he says “there’s no better way to gel a team.”

“We go for a whole month, to somewhere that has the holy trinity of power, Internet, and beach,” Barrett says. “We look for somewhere inexpensive.” Last year, it was Vietnam. This year, it was Railay Beach in southern Thailand.

Expensify had six new employees start in September, right before the trip. At most companies, they’d still be ramping up, but at Expensify, they’ve had a once-in-a-lifetime experience with their new colleagues already.

Far from an all-expenses-paid vacation, this was a working trip for everyone. People kept up on their normal job duties and participated in long-range planning meetings as well.

Expensify covered flights and some meals. it already buys employees lunch in San Francisco, where the company’s based 11 months out of the year, so that wasn’t an additional expense. Employees covered their own lodging expenses. (Some rented out their homes while they were away to defray the cost.)

All told, Barrett estimates, the trip cost the company $30,000. That’s not a big hit on the company budget. Expensify, one of our top 10 startups of 2009, has raised $6.7 million, and Barrett forecasts it hitting profitability without any extra money, though he’s thinking about raising a round to accelerate the company’s expansion early next year.

The trip is optional, but almost every employee participates, Barrett says. (One new hire was in the middle of moving across the country and couldn’t make it this year.) Some only do the middle two weeks of the trip, which is fine.

“We think this is the most productive month of the year,” Barrett says. “You take them out of their time zone. They don’t speak the language. It’s this very inclusive environment.¬†You have time for the conversations you never have otherwise. Our best ideas for the company come out of these trips.”

The trip began in Bangkok. From left, lead designer Shawn Borton, software engineer Jason Kruse, and lead software engineer Matt McNamara ride a ferry across the fast-flowing Chao Phraya.

Barrett takes a break from watching a muay thai fight to reboot a server.

For travel, Barrett swears by his ageing Sony PictureBook, on which he's installed a Linux operating system.

The Expensify team lines up after landing at the Krabi airport. Next up: a bus ride, then a boat ride.

Here's the destination: Railay Beach, outside the town of Krabi in southern Thailand.

Expensify founder and CEO David Barrett gives it the thumbs-up, too. Including past companies, this is the eighth offshore trip he's organised.

The team celebrates making it to the beach.

Kruse prepares to dive.

Expensify's Daniel Vidal takes a dive. (Also totally buff, so you know he's in sales.)

The company held a big planning meeting at a villa in Railay Beach.

For the last part of the trip, the company returned to Bangkok and held a big team dinner.

The view from the restaurant, 64 floors up, was stunning. The bill for the meal: $1,000.

Unforgettable.

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