Previous month:
January 2013
Next month:
March 2013

February 2013

Sailboat Racing and Building a Business: The Unexpected and Sleep (Part 5 of 5)

The Unexpected Happens Unexpected

In a long race, despite all the careful preparation, things will go wrong – equipment will break, crew will get sick/hurt, weather will change unexpectedly, and crew morale will start to sag.  Facing obstacles with a smile – and directness – is the way forward.  Face the obstacles, have a plan to work around or through them, get the crew involved with the solution, and keep working it with a smile and a sense of humor.  If the skipper’s emotions are “down” the whole crew feels it and conflict and disagreements are going to happen.  If the skipper is “up” and clearly in command, the crew feels that too – and works together as a team to address the unexpected.  This can get really hard in a race with a defined end when one finds oneself in a position where one cannot ever recover – such as breaking a mast or being too many miles behind to catch up.  That is the real test – keeping the crew motivated and positive when the die is cast. 

Business has no “end point” like a race so one can always look to the better future – though at times when the better future is too far off, it can feel like there is no light at the end of the tunnel.  Leadership is very much about showing and spreading hope and direction.  Leadership is rarely about working harder – and more frequently about getting the team to work smarter or when it’s tough, looking longer term (we took a third place in the 2012 PacCup… but will be back in the future pursuing that elusive first place).

Sleep is a Weapon

Crossing oceans is a long distance long term activity.  Winning races across oceans means pushing the boat hard for days on end – and making good decisions day after day for weeks. Tired worn out people (skipper or crew) cannot push the boat hard – and make poor decisions.  Poor decision’s leads to equipment damage and more lost sleep – which leads to more bad decision and more lost sleep – in an ever tighter death spiral.  Absolutely no fun.  It’s so important  to FORCE people to sleep when they are off Waking up refreshedwatch (we have three watches, two people per watch, each person is on deck working 2 hours and then gets 4 hours “off” to rest/sleep/eat).  Crew that doesn’t get their sleep makes mistakes in judgment, are in danger of crashing the boat, may hurt themselves or others mishandling lines – and are likely no fun to be around.

Work is very much the same.  People need to rest and recharge.  Tired and worn out staff make mistakes and are likely unhappy (which is infectious).  People cannot be expected to work 110% all the time.  Planning for people to work 100% all the time is a fool’s errand – as the unexpected happens and one needs planned “slack time” – both to recharge and to have some “extra” to give when the unexpected happens. 

 In sailboat racing the Kiwi’s (New Zealanders) are known for giving 110% day in and day out.  They win a lot of day races and short 2-3 day races – sprints – but rarely around the world.  The French are the perennial champs of sailing around the world (crewed and shorthanded).  They have learned the value of sleep and pacing oneself.  They understand to get around the world is a marathon and to win you need to finish.  To finish means pushing the boat and themselves only 90% much of the time so they have “something extra” when the going gets tough – like racing across the southern ocean in 40 knots of wind and 30 foot seas for weeks on end. 

Business is a marathon.  Winning at business this month, this quarter or this year is not nearly as important as winning over a long period of time – such as 3 to 5 years.  So pace yourself.  Save something extra for when you really need it.

On the lighter side…

After the race, sailing the boat home is a great way to recharge from two weeks of 24x7 racing and a week of rushed boat preparation for the voyage home.  I always choose “new” or “inexperienced” crew for the trip home.  The 17 day passage is a great time to relax and really get to know people in a deep way – like the way you know your neighborhood and school friends when you were younger – but as adults we rarely if ever have the opportunity to do. This doesn’t have a direct corollary to business – except maybe the value of occasionally taking the time to get to know your fellow team members – and partners – better (one of the reasons I like to put up team members, partners and staff in my mother-in-law apartment for a few days from time to time).  

Sailboat Racing and Building a Business: Crew (Part 4 of 5)


When the going gets tough the tough get going.  It’s easy to crew on a boat on a sunny day with small waves and little wind.  It’s hard when its 3am in the morning, the waves are big, the wind is blowing hard – and you are just on the edge of “crashing”.  One needs to develop a crew one can understand and trust when the going is hard – and this takes time on the water and time in tough conditions.  Everyone starts out with different skills – and everyone has different learning needs.  Prior to the race, several other races are needed to evaluate the crew’s strengths and weaknesses , place crew in positions that leverage their strengths, and teach people new skills that make them a more effective and flexible crewperson.  This is also very much about a crew that when they going gets tough, they are more supportive and sensitive to the strengths, weaknesses and feelings of their fellow crew members.  Everyone is different and have a crew that really knows each other deeply is an important success factor.  It’s also important to insuring people are enjoying the race.  If you don’t trust your fellow crew, you are not having fun and the rest of the crew can feel it (all these people in a small uncomfortable space for near two weeks). Last, it only takes one “insensitive I know better” crewperson to make the whole crew miserable and turn what should be fun into a not fun experience – not something you want to discover 2 days out with 11 days (locked in a small uncomfortable room) in front of you. 

Crew rowingAs in business you need to know your team strengths and weaknesses, develop your team through time working together and training, and build up a deep trust in other team members to do their job well (enabling you to focus on your job and do it well too).  Sailing very much teaches you everyone needs to focus on their job – and not someone else’s job.  On a sailboat, it only takes a few minutes to recognize crew that are spending more time focusing on someone else’s position – invariably leading to both their playing their position poorly and the person in the position they are trying to get involved in getting seriously annoyed with them.  One needs to play one’s own position first and foremost and it’s the skipper’s job to step in and provide direction if someone is not doing their job right (not one of the crews job).  That said, if you are a very emotionally skilled crewperson with deep sailing skills, you might be able to get another crewperson’s permission to give them advice.  If you see a problem with one of the crew, you talk to the skipper about it on the side.  Most times the skipper is already aware and doing something – but if not your feedback will help determine if the skipper needs to do something or your view needs re-alignment.  As on a boat, the same goes at work. See the happy crew at the finish – a sure sign of success!

Sailboat Racing and Building a Business: Weather (Part 3 of 5)


60% of winning a long race like the Pacific Cup is routing strategy based on the weather.  Preparation and crew are just 40% of the winning combination.  This means one spends a lot of time tracking weather patterns, reviewing weather forecasts and doing “routing analysis” during the month following up to the race start – and during the race.  The hard part is weather forecasts are only accurate for 3-4 days.  Though you can get 15 day forecasts, only the first 3-4 days are reliable, a few more days are “iffy” and beyond 5 days are highly unreliable and not to be counted on.  So if you are going to take 13 days to get to Hawaii but only have a reliable weather forecast for the first 3-4 days, what do you do?  You assume the weather forecast are correct all 15 days and plan accordingly.  You then get and analyze weather updates twice per day and adjust your routing strategy based on these weather updates.  What one learns over time, what doesn’t work is “guessing”, thinking you know more than the professional weather forecaster with a room full of super computers, or using some non-scientific “someone else told me” approach.  One also has to recognize even using the best fact/science based approach; one gets it wrong at times.  The weather defies long term prediction.  The “best” navigators identify changes in the weather forecast “early” and make the needed changes in boat direction at this early time – while others wait for clearer and more certain changes in the weather forecast – putting them behind.  This said, a lot depends on the number of competitors on the race course.  Weathermap If there are just a few competitors, one can wait a bit longer to make a decision as the chance one of them is already “in the right place for the new weather pattern” is slight.  If there are lots of competitors all over the ocean, one of them will be in the perfect place going the right direction purely by accident – so you need to see this early so you can stay within reach of the competitor who was lucky. 

This very much applies to our business.  Some folks are smart and some are lucky.   Being “ahead” doesn’t tell you if one has been lucky or smart.  Over time, after several key strategic decisions, one starts to see who was lucky and who was smart.  Who makes good early decisions time after time – and who gets lucky a few times and then falls back after a few bad decisions.  So have a science/fact based strategy and be quick to change it as the environment around you changes.  Don’t get discouraged if you are a bit behind as there will be opportunities in the future for you to make a good decision and the competition to make a bad decision.  Though you want to be quick to change strategy if the environment changes – if the environment doesn’t change and you have solid fact based strategy, be patient and stick with it.  In the PacCup, it can take several days for one’s routing strategy to play out and those who win almost always look behind early in the race – as they pursue a strategy based on what the weather will be like in a few days’ time.  When the competition is “close” be patient following one’s strategy – waiting for the competitor to make the first or more mistakes.  Business is very much the same.  One needs to spot changes in the market/environment early and change strategy to match this changed market – before competitors do – while at the same time following one’s long term strategy and not changing direction based on non-environmental changes (like what a competitor did or said last quarter).

Sailboat Racing and Building a Business: Post Mortems (Part 2 of 5)

Post Mortems Postmortem

Every race – of which there are 10-12 per year - is an opportunity to learn more about the boat, the crew, the equipment, the layout, sail trim, etc.  After 6 years and 70-80 races one learns a lot about the boat and crew (only last year, after 5 years, after losing several races to identical boats, did I learn how to set-up the boat’s mast rake properly).  One also learns the most when racing with the most closely matched boats – and it’s harder to learn when racing against boats that are less competitive or very different in form.  Winning means dissecting one’s losses to understand what went wrong.  If you don’t know why you lost – you are going to make the same mistake and lose again. 

This applies to work too – whether one’s team within the larger corporation or as an entrepreneur building a new business.  When one has a loss or failure at work, one has to go through the painful and frequently introspective process of figuring out “why”.  Often one doesn’t know exactly why one “lost” but has “suspicions” that need to be reviewed over time during other races to narrow down the source of failure.  Ignoring, denying or not inspecting failures means improvements will be slow or not at all.  “Those who don’t study history are doomed to repeat it.”  With my race crew or at work, it takes time – face time – to build the personal trust needed for people to be open and honest – to be able to criticize their own performance in front of the team – and take criticism from other team members – without being defensive.  I have taken to using Autodesk’s “Mature Directness” tenant with my race crew too!  

Sailboat Racing and Building a Business: Intro and Prep (Part 1 of 5)

Some of you know I am an avid sailor – and more specifically love long distance sailboat racing in the ocean.  Having been racing sailboats for 40 years, I have learned a number of lessons and rules of thumb that I see many successful entrepreneurs also using.  At risk of this coming off as hubris, I’ll be sharing these lessons with you over the next few posts – using lessons from successful sailboat racing as applied to successful business. 


The Pacific Cup is held every two years – even numbered years.  From 45-70 sail boats in several divisions (7-10 boats per division) race the 2070 nautical miles (1 nautical mile = 1.12 statute miles) from San Francisco to Kaneohe Bay (Oahu, Hawaii).  I have done this race 12 times on a wide variety of boats from 24 to 73 feet in length and with crew sizes that varied from two people (“double handed”) to fourteen people.  It is typically a 10-13 day passage that starts with a few days of “big wind and waves” and then a week plus of “running” downwind with the spinnaker up.  Envision several people locked in a small room with a great view for almost two weeks - with the stereo blasting 24 hours per day – and a bucket of water thrown across the room every few hours. And the room is moving like in a strong earthquake.   After close to two weeks of this, one gets a week on land spent mostly preparing the boat for the return trip, and then one gets back on the boat for the 16-19 day mostly upwind “beat” home. Sailboat


You don’t win races if you are not prepared – more prepared then your competition – preparation as a source of competitive advantage.  For the race to Hawaii, I am almost continuously preparing – since first acquiring Green Buffalo.  I bought the boat knowing I wanted to be competitive (starting with a solid competitive foundation) and then restored and continually upgrade and fine tune to make it ever faster.  In this year’s PacCup, I spent the last few months sailing with the crew, analyzing weather patterns, and fine tuning equipment – while most of the competition was scrambling to get the “basics” ready for the race. 

As with sailboat racing, you need to be thoroughly prepared - the “basics” must be a given - so you can focus on how to improve.  Once in a while someone unprepared gets lucky and wins a race – but over time the best prepared win consistently.