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Board Meeting: Barbados 2014

We built this business to be a ‘lifestyle’ business. While we certainly work hard, we play hard too. That’s why we transform our team meetings and management retreats into full blown adventures.


This year, Shane decided to preempt the birth of his second child by taking his family to Barbados for a month. Reid and I were more than happy to tag along at the end and call it our quarterly management retreat. Unfortunately, we were not able to find direct flights to Barbados, but that’s ok. The destination was well worth the journey.

Barbados 2014 Stairway to Heaven

St. Nicolas Abbey

In case you haven’t picked up on it, Shane essentially lives in the future. He treats what will come to pass as if it is happening today. This makes him an outstanding planner. So it’s not surprising that we kicked off our retreat in style with advanced reservations to a private high end moonlight dinner at the St. Nicolas Abbey – a gorgeous oasis in the otherwise desert island featuring a distillery with roots going back to 1660.

St Nicholas Abbey Barbados 2014

We generally start these retreats by checking in personally and evaluating our life goals. I can honestly say, there is no better environment for weaving optimism into introspection than at a moonlight dinner at the Abbey on a warm Thursday evening with a glass of 15 year aged rum on the rocks.

Surfing Freights

Over the years we have sought out many surf breaks. Costa Rica, Nicaragua, El Salvador, Mexico, Hawaii,… In all the time that we’ve explored world famous breaks, I’ve never had such a delightful experience as I had surfing Freights.

Shane Surfs Barbados

First of all, it’s as easy as can be to get to the wave and the water is always comfortable. In fact, I talked to a Swiss surfer who pointed out the convenience of flying in from London and within 20 minutes of touchdown, being in the water riding a wave. In our case, Shane managed to get a house that had a perfect view of the wave so we could peek at the crowd and conditions all day and as soon as it looked optimal, we’d stop our conversations and run out and catch some waves.

Beyond that, the locals are incredibly friendly. Personally, as an avid stand up paddle board surfer, I often find that my surf sessions are met with aggression. Not so on Freights! Not only were people friendly and welcoming, but there were a number of very talented stand up surfers frequenting the wave. One of them informed me that not 3 months ago, the Bajan surf association added stand up paddle boarding to all their surf competitions and started a campaign of proactively getting young surfers to ride SUPs.

This cheerful crowd and moderate swell also heralded Reid’s first real surfing experience. He not only caught a wave on a stand up paddle board, he rode it masterfully and then proceeded to catch 3 more! I think we may have finally converted him!

Oistins Fish Fry

There is travel for relaxation and then there is travel for adventure. I consider Oistins fish fry to be more on the adventure side of the equation. As luck would have it, a merry band of Automatticians had simultaneously descended upon this adventure and met us at the Oistins fish festival for a dark and fishy dinner.



Let’s start by pointing out that there are dozens of virtually identical fish fry shacks where the primary differentiator is who’s got the best hawker. So as we wandered through Oistins amidst the fry shacks, we were constantly inundated with people interrupting our conversations trying to get us to sit down at their shack.

When we met up with the Automattic crew and finally picked a shack to patronize, the waitress seated us behind the kitchen out back where there were no lights and promptly brought us greasy slimy menus (seriously, my menu was a thin cardboard sheet that appeared to have been entirely soaked in oil so that when i tried to open it, the page ripped off like a sheet of thin dough).

No sooner than 40 minutes after taking our orders, our meals started to appear in small batches. Eventually, after most people finished their filleted flying fish dinner plates, and just about when I noticed the 3 inch long cockroach running around in the kitchen screen, my whole bass plate showed up – in the dark – head, skin, tail, fins and all. It was a little terrifying and delicious – as any adventure worth it’s salt is.

Captain America, Mon

We often work and play so hard on these trips that by the end our brains become a bit mushy. That’s why we have a tradition of going to the cinema in foreign countries. Last year, in Nicaragua, that entailed watching Star Trek with Spanish subtitles and having the rowdy locals laugh 30 seconds after every joke. The big take away from that one was Zoe Saldana announcing “Yo hablo Klingon”.

This year we had the pleasure of seeing Captain America in Barbados. The adventure started when we stumbled into the VIP theatre. A small lobby with elevator music and some, mostly older, white folks sitting on the couches reading. We asked the well dressed black staff what the difference is between VIP and normal movies. They chuckled and then, realizing that we were sincere, got uncomfortable.

“VIP movies are more expensive… oh… and there aren’t as many of them.”

Not seeing a value add, we decided to go back to our search for the non-VIP movies. When we arrived upon a long line of black people we realized that the VIP movies are probably targeted to wealthier white people. So it appears the VIP tickets are basically a tax on racism.

Needless to say, we charged ahead in the non-VIP movies. Somewhere between the paralyzing inefficiency of the concessions system, my accidental purchase of 3 large popcorns and the surprise of walking into an enormous theatre with only 3 other people attending the movie, I managed to start the show by dumping an entire bag of popcorn on Shane and Reid. Apparently, the people of Barbados, whose roots are British and Canadian, don’t have a lot of interest in Captain America. And it’s too bad, because I can only imagine how much more fun it would have been if the theatre were full of people like the 3 sitting behind us. They hollered at the screen with thick Caribbean accents at every conflict.

“Kick ees ass mon!”

Of course, whenever Samuel Jackson or Anthony Mackie came on, then the shouting would really pick up. Too bad they weren’t showing Captain Canada. That might have really packed the joint!

Perception vs. Reality

Whenever I talk about our retreats, it seems that people always leap right to the conclusion that it’s a faux vacation. As though the photos we send of surfing and sipping on piña coladas depicts the majority of our time spent. The honest truth is that most of our time is spent generating financial reports, spreadsheets, updating wikis and then entering into vigorous debates about what it all means and what we should do with all that information. Unfortunately, spreadsheeting and financial reporting are simply not the most photogenic activities. It’s definitely true that we have a lot of fun on these trips, but it’s not without the adjoining 10 – 14 hour per day work sessions.

Barbados 2014 Meeting

So what do we spend all day doing? Here’s our rough agenda from this trip:

Friends, Family, Finance, Fitness, Faith & Fun

We start every retreat by checking in on the 6 Fs. This usually takes the better part of our arrival day and gives the rest of the retreat personal context.

Corporate Financial Review & Valuation

Barbados 2014 Ocean Dive

Then the fun picks up when we crack open our ‘pipeline doc’, an increasingly sophisticated multi-page spreadsheet that essentially gives us a snapshot and forecast of our company’s health. In a nutshell we look at our books, sales pipeline, product sales, cash assets, and our reserve funding and poke at all our assumptions. When we’re all done tweaking numbers, the spreadsheet either says “Go Surf!” and tells us that Reid can afford his new kitchen, or it tells us how far short we are on our sales. This year, the crystal ball told us that Reid should get cooking on building his new kitchen. Yay!

Opportunity Cost of Service projects vs Products

One of the things that we often struggle with is deciding which opportunities should take priority. It’s a wonderful problem to have. But it’s a challenge none-the-less. For example, should we take on another service project or build another product? How much service revenue or what other service project scores make it worth sacrificing building a product? How long is the return on investment on a product and what can we afford?

After the better part of a day spreadsheeting some projections we concluded that there are too many variables and that we really still don’t know how to best make that decision (If you have any suggestions, feel free to let us know).

Project Manager

During our last team retreat in Costa Rica, we asked everyone if they had any feedback for us. The single most common recurring theme was that the three of us are personally owning too many things to be exceptional at project management. Especially me. So we set about growing our business to afford project managers. We now have 2 PMs and are interviewing more. A lot of time went into defining success for PMs, thinking about reporting and how to set them up to win. Upon reflection, I’m not sure how we managed to get this far along without dedicated PMs.

Staffing & Recruiting

We love our team! Seriously! We talk about it all the time. Another nice problem to have is that we have more work right now than the team has time. And since we keep finding ourselves short on time to review applications and do recruiting, we’ve decided that we need help from a professional independent contact recruiter.


We’ve often talked about things we’d like to report on and we’ve built a few reports here and there. However, our business is growing such that Shane, Reid and I can’t actually effectively keep track of it. As we delegate more responsibilities, reporting is going to become increasingly important. Rob and our project management team also kicked us off with some specific requests. So we spent a bunch of time working out what reports we’d like to generate so that we can try and better understand how well our projects are moving along and how best to focus our resources.

What’s Next

We have some babies on the way. We have some really amazing projects in the hopper. And we have some substantial product offerings brewing. This is going to be an exciting year and we look forward to sharing our adventures with you.


Barbados 2014 Reid's Dusk Swim