How a ‘workcation’ worked for our startup

We were in the middle of a product review session when Gary looked up and asked, “Are we going to Bali in a couple weeks?” The idea of a “workcation” had been floated a week ago and then forgotten in the midst of frenetic deadlines before the holiday season.

But it was an intriguing concept — most of our customers would be on vacation anyway in early January. And it would be a chance for the founding team to come up for air out of the concrete jungle and establish some foundational pillars of what we envisioned our company to be. And why not push the boundaries of team chemistry with some surf sessions and volcano hikes mixed in?

Making the Decision to Prioritize Company Culture Is Not Natural.

I initially was a bit ambivalent about blowing off for halfway around the world. For a young company that needed to improve product, sales, etc., I could think of many other things we could prioritize. But as the rest of the world attacked Day 1 of their annual New Year’s resolutions they are sure to complete, we found ourselves eating breakfast with the morning surfers on Echo Beach, Bali, hyper-caffeinated as our bodies adjusted to strong Bali coffee, with pens and notebooks out to blueprint the agenda for the trip and our year.

The first night of jet lag back in New York City, I had a staring contest with the ceiling and thought specifically how the workcation was worth company time. It was more than the rejuvenation and renewed motivation — we somehow met the vague purposes that let us BS our way into the trip in the first place…

To other company founders and entrepreneurs thinking about doing something like this, the takeaways that I would like to share are as follows.

1. Company Culture Can’t Be Growth-Hacked.

One of our major goals for our workcation was to align thoughts on company culture between the founders (more on this on another blog post). We had a roadmap for product and sales, and are well-versed in SaaS ABC’s, but there was a realization that to compete in our category, we have to be able to evolve at scale, and to do that, we have to formalize our company DNA into something that everyone understands and owns.

Writing down the objective in all caps always helps.

In New York, we spent what we thought was a lot of time bonding and “creating culture.” Like a lot of startups, we often have beers together, pull long nights, work weekends, and discuss and agree/ disagree about many different ideas. Yet at the end of each of these sessions, or the next day, we typically get distracted again on other tasks. Taking that offsite helped us to really focus on that for days on end.

2. Be Authentic: Running a Start-Up Is Not An Excuse Put Your Life On Hold.

As different as we are, all three of us can be described as wanderers of sorts; naturally curious people who like to explore, looking for unfamiliarity. In the office, that affects how we build our product or how we approach solving customer problems. Yet, curiosity about product and business is fundamentally rooted in life experiences, and this workcation, about as far away from New York as we could have gone, fed and rejuvenated that curiosity. We found it in eating unrecognizable food from street stalls, from deep conversations with expat entrepreneurs about start-up life in foreign countries, and in philosophical leadership questions to our trek guide.

Matt already seemed to know that only one of us would catch a stomach bug.

These new moments and experiences stimulate us. As Matt always says, “Let’s be who we are,” and the trip was a natural product of that curious spirit. I think all three of us gained a lot — both as people and as business operators. And though the benefits are intangible, being authentic feels right and will pay off in the end.

The emails can sometimes wait.

3. To Make a Massive Change in the Conversation, Make a Massive Change to Your Environment.

Conversations that we wouldn’t have had in New York came quickly in Bali. Nursing beers in our villa pool easily spurred talks on topics ranging from how altruisim can make sense with our business strategy to how we can hold on to our moral courage throughout the chaos of start-up life. And by the end of the trip, we were able to package these convictions into a mission and value statement.

We traded in yellow taxis driven by crazy cabbies for motorbikes driven by crazy children.

Sometimes the big picture stuff gets lost when so focused on tangible wins. But our marketing strategy became much more refined as we further detailed its sequence throughout different phases. Our HR conversations became more than just number of hires and needed skill-sets, but figuring out the types of personalities that would give us ongoing momentum. For us, it was just simpler yakking about this stuff sipping Luwak coffee while overlooking cascading rice terraces views.

4. Take All Night Volcano Treks without Sleep

Probably the most important thing that we took back from the workcation was the enhanced bond formed between the founders — we went through some things together that showed us who we are, individually and collectively.

We wandered the streets of Ubud in the middle of the night trying to find our trekking guide for an all night hike up Mt. Agung, Bali’s tallest volcano. We told dumb jokes while watching Bali sunsets and traded fun stories from the day while the locals (who already knew everything we did) grinned at our foolishness.

I observed Gary’s determination when he refused to complain while clawing down the volcano and saw Matt’s patience and competitiveness while learning to surf as he got battered by massive waves and kept going back (though the 10-year old Balinese kids seemed to have no problem). We danced on top of Mount Agung as day broke after climbing all night. As traveling always tends to bring out, there is a deeper honesty that emerges as you learn more about their personal backgrounds, what motivates them, their integrity, and their communication styles.

Good team vibes watching the sunrise

5. Yes, there’s Internet at the Beach.

One of the biggest surprises for me was, while focusing on bigger picture strategy and culture, we were probably just as productive with small tasks as we would have been sitting back in our office in New York.

Making friends with the bar owner with the fastest internet in Canggu helped us out quite a bit. That bar turned into our daily office. So despite the ultra-relaxed culture of Bali, we didn’t miss much of a beat. And sometimes you have to be resourceful — when the town shut down and the village of Canggu was whooping it up to a local cover band at the“office” bar, I found a quiet spot (Matt and Gary got their jam on) at the skateboard ramp next door and worked out the kinks of our financial model. I marvel at how connected the world is…

The only thing better than the view was the fiberoptic internet.

“Cause you can’t knock the hustle” -Brooklyn’s Finest

So sure, going to a place like Bali can help accelerate these processes mentioned. But the real reason why it worked so well for us is that we made the most of the experience. We are determined to be doing it our way. We are determined to make Oz into what we are and believe.

And along with an absurd farmer’s tan, the workcation gave us the backdrop needed to push us on our path. We’re not going to put our lives on hold while we build this.

Interested in workspace? Get in touch.