Make Every Decision Easy…Even Who to Marry

How do you turn life’s great questions into easy decisions?

A clear strategy.

I’ve changed a lot of my thinking on business and relationships due to my study of strategy.

A lot of business strategy and finding the right person is centered around commonalities.  These companies all did X, Y, and Z.  Look at their growth.  She likes Star Wars, and drinking beer (Jim Jefferies anyone)?  When are we getting married?

That’s not what a good strategy or relationship are built on.  The question to ask is:

What are you willing to give up?

It’s much easier to find positive traits of said market or prospective mate, if, in fact, that’s what you’re trying to find.

I’m pretty much done staying out and getting drunk at the bar.  Don’t get me wrong I love dive bars.  I’ve spent more time in dive bars than most people should, and even fewer will admit to.

So when we meet for a cup of coffee, she’ll ask if I like to drink.  Yes, I do.  I like it for an hour or so.  Then it’s time to go do something else.

The question is are you willing to give up drinking all night to hang out with me?  If not, great.  Let’s see if we can find each other a sweet job or introduce us to someone else.

The question is are you willing to give up the fandangle portion of the market because the customer acquisition cost will be too high?

I love strategy.  It might come from the fact that I like learning and thinking…but executing?  See my previous post about Fearing Execution.

I heard Seth Godin describe strategy consultants.  It basically came down to this:  You pay them so you can name drop to justify a decision.

“McKinsey said we could…”

Most of the time it was a foregone conclusion.

Ask 10 people the difference between strategy and tactics and you’re likely to get 10 different answers.

I like the one Bob Bloom gives in his book The Inside Advantage, “A strategy says how you intend to achieve your goal; a tactic is the way you intend to implement your strategy.”

In the recent UFC 202 rematch of McGregor vs Diaz, McGregor’s strategy was to get Diaz off-balance and leaning back.  The tactic was leg kicks to Diaz’s front leg.  It worked….barely.

Blitzmetrics uses the Sierpinski triangle as a blueprint for business and personal development.

One of these triangles within a triangle is Business Strategy.  Each corner (starting at the top and moving clockwise) is labeled:  Goals, Content, Targeting.  Together they make up Business Strategy.

I like the idea because it’s practical, especially for something called a strategy.  Goals influence the content you create, which influence who you target.

You can’t win the game if you lack any of these.

If we revisit the Bloom definition we see that this clearly explains “how” we are going to reach our goal; by using targeting and content.  Practical?  Check.

I like to think of strategy as the minimum amount of how that must be present to achieve your goal.

What are you willing to give up so that your decisions in business and relationships are easier?


7 Things I Learned while Leading Skiing Expeditions

There is only one way to become a leader, and it isn’t taught at Harvard Business School or Wharton.

Before we go any further let me say that I am one of those people who try to talk people out of going to school.  That is unless it’s on the school’s dime.

You only become a leader by saying yes to an uncertain situation.

Being a leader involves only one thing.

napoleon bonaparte leader  quote


That’s it.  A leader doesn’t put people in a position to succeed.  That’s managing.  A leader does this:


I led ski expeditions into the most glaciated region in the world outside the polar circles.  The expeditions were 24 days long.  The weather in Southeast (that’s how Alaskans refer to the panhandle) is notoriously fickle.  It made it tough for helicopters or planes to fly.   This meant that if or when things go south, you’ll probably be on your own.

I’m not being dramatic when I say I made life and death decisions on a regular basis.

Here’s the list:

1.  It’s Okay to be Afraid – I can’t tell you how many times before a big climb or ski I wouldn’t sleep.  I was scared.  Could I get us to the top?  Could I mitigate the risk?    It’s healthy to be afraid when doing things that have real consequences.

2.  Use Another Emotion to Replace Fear – You don’t conquer fear or any emotion for that matter.  You replace it.  Embrace this.  Out in the mountains, you can’t rely on music, movies or YouTube to pump you up.  Get creative.  In town I listen to 2pac’s, You Can’t C Me or Mel Gibson’s freedom speech from Braveheart.

3.  Risk = Likelihood X Consequences – The real trick to risk is controlling likelihood.  If the likelihood is almost 0 then it doesn’t matter what the consequences are.  If you’re doing something worth doing the consequences are likely high.

4.  Treat Your Second like he’s a First – It will pay off when the shit hits the fan.  Trust me.

5.  Plan – Some people that I trust are against planning. That’s dumb.   One time I had to get a woman out of the mountains and the weather was so bad that you couldn’t see 5 feet in front of your face.  I planned a route through 2 mountain passes using a compass and a map.  We later went to South America and learned to tango and ski.  But that’s another story.  Planning pays.

6.  Go Farther Than You Think You Should –  When navigating in a whiteout, or uncertain circumstances, your brain is working so fast that it feels like you should’ve gotten their already.  Before going set a boundary.  Add 20%.  That’s your new boundary.

This doesn’t apply to things like turn around times when climbing or pursuing goals that have already been done.  The uncertainty doesn’t come from the route, or the unknown, the uncertainty comes from your ability.   Very different.

7.  Bring Good Chocolate and Coffee –  It’s impossible to bring too much of either.  Make it a surprise.  When faced with a low point, a luxurious surprise goes a long way to keeping morale up.

8. (Bonus) Don’t Read about the Thing You’re Doing – When I first started leading these expeditions I used to bring books about other mountain climbers.  The circumstance would come up where I was stuck in my tent due to weather, reading about a climber who was stuck in his tent due to weather.  It was mildly amusing at first, then I started to feel like Jack in The Shining.

Fearing Execution

Is that such an unreasonable thing? That is, fearing execution.  And who wants to be an executioner anyway?

I’ve spent most of my life not executing.  It’s much easier over there.  The sun is always shining and water is warm.  The problem is that it’s never your sun that is heating the water, and it only feels that way cause your drunk.

My issue with execution is that it’s final.  I like, nay, irrationally  love having options.  This makes it rather hard to execute, now doesn’t it.

They say execution is everything.  I don’t necessarily believe that either.  I have some friends who are amazing at executing.  They also tend to repeat tasks or chase their tail because they executed a circle.   No thanks.

What works for me is the ‘death’s ground’ strategy from Sun-Tzu’s Art of War.  It is the only strategy that I’m aware of that forces execution.  It’s easy; give yourself no other way out.  Watch the magic happen.

I’ve implemented this strategy many times in the past few years.  I moved to Alaska with no job, contacts, house or prospects.  It worked out fantastically.

I recently pulled a similar maneuver by moving to San Francisco.  No job, contacts, house or prospects.  I camped the first days in a tent before I found a place.

Power of Broke
Power of Broke

This strategy isn’t for the faint of heart.  You have to be a minimalist and deal well with uncertainty.  Also it’s not a viable long term strategy.

The challenge I face is recreating the sense of urgency without having to hit the ctrl+alt+delete keys every time.  One of the best ways to do this is found in Robert Greene’s 33 Strategies of War  Go before you are ready, and you will find yourself motivated.

If I’m being honest, I don’t have the track record that I wish I had.  I haven’t executed at a level that I wish I had.  I haven’t failed as often as I wish I had.

But that’s all changing.

If you could only be known for one thing would it be strategy or execution?

The Coming DiSaaSter

Predictable Revenue

The holy grail. Hell, there’s even a best-selling book that carries it as its title.

This is what every investor, start-up founder, and Fortune 500 CEO is after.

I haven’t lived in San Francisco that long, but I have yet to meet one person who isn’t working, selling, or founding a SaaS business. That’s an exaggeration, but not by much.

The $202 Billion Question:

What happens when predictable becomes volatile? DiSaaSter.

It calls to mind traders who sell options on stocks.  These options expire worthless 95% (debatable) of the time.  What happens the other 5%?  They lose their bankroll, house, and shirt.

Now I know the economics that drives an option writer to go broke aren’t the same as a SaaS business. But is it really?

It’s the lure of smooth cash flow. These ideas are not exactly what Nassim Taleb would call  Antifragile.

Not all SaaS businesses are going to go belly-up when volatility comes, but I do predict a particularly fast thinning of the crowd. Warren Buffet refers to these people as “swimming naked”. The tide is going to fall like someone pulled the plug on the bathtub drain.

So what?

So the point is that if you run, work, or are thinking of founding a SaaS business, maybe it’s time to start thinking about zigging while everyone else is zagging. The customer might only buy from you once, but you already have all your profit. It takes the average SaaS business 18 months to recoup the customer acquisition cost.

What is the customer going to think about maintaining your cash flow at the expense of his?


How to Avoid “Living in the Moment”

“High side!” I yelled.

My boss’s truck teetered over the edge of an embankment.

It was January in Montana, in the mountains.  It was -20 degrees that day on the ski hill.   Down below was a river that was half frozen.  Maybe this was when my vertigo first appeared?

It’s amazing what thoughts pass through your mind in a situation like this.

My first was that if we go into the drink I’ve got about 90 seconds to get out of the water.

Get your hand on the seatbelt buckle.

I wondered how swimming with ski boots was going to go?

Reliving this moment isn’t entirely unlike this scene from True Lies.

“Live in the moment”, is a piece of advice that you hear at weddings, graduations, and TED-type talks.

Good advice.  No one ever tells you how to do it.

Why is this?  How do they do it?  How do I know when I’m doing it?

95% of those people are just repeating what someone else “smart” said.

I know this because I repeat stuff that smart people have said all the time.  In this case, I have actually done it.

Here’s how to do it:



“Where the magic happens” is when you are living in the moment.

This moment can be designed or it can be forced upon you.  See my predicament above.

Ask yourself:  When was the last time I did something for the first time?  If the answer is greater than a week.  You’re avoiding living in the moment.

At first, you won’t realize your living in the moment until after the fact.  But, if you keep pushing yourself out of your comfort zone you’ll start to recognize the tell-tale signs before hand.  Anxiety. Excitement.  A feeling of pressure.

This isn’t a post about how to deal with these emotions.  Maybe next time.

The good news is that the “magic zone” is auto-regulated.

People thought I was crazy because I was a professional ski patroller, ski mountaineering guide, and helicopter ski guide.

They should’ve hung out with my friends.  They regularly did things that would make my head spin.

I needed them to keep pushing me into the “magic zone”.  I’d like to think that they were thinking the same thing about me, but who knows.

How do you start to do this?

Ask for a discount at Starbucks.  Chat up the stranger in line at the train station.  I haven’t done this one yet, but try selling someone a $5 bill for $1.  I hear it’s impossible to do.

Slowly raise the stakes.

Public speaking is my next “magic zone” target.  Or swing dancing.  I don’t know.

The point is that the comfort zone is always and forever acting like Mary Swanson from Dumb and Dumber.  This isn’t a knock on Mary, she looked good, but more a call to start noticing when people (especially beautiful women), events, and mysterious forces are limiting your time in the “magic zone”.

“High Side!”

Luckily everyone in the truck was either a professional river rat (whitewater guide) or had been on enough whitewater trips to know what it meant.

Everyone dove to the driver side to try and counter balance the truck.

The truck stopped teetering.

Slowly, starting with me because I was on the lowest corner hanging out over the edge, we climbed over each other to get out.

My boss was the last one in the truck.

I put all my weight into pulling down on the open driver’s side door to act as an anchor.  My friend grabbed my jacket to hold me.  The rest followed suit forming a line.

This moment had my full my attention.  This moment was real.  The moments that you are most alive, are the moments with real consequences.

My boss looked me in the eyes.

“If this thing starts moving…let go.”

As he shifted his weight, the truck started moving….

True story.