woulda, coulda, shoulda

Do you ever look in the rear view mirror and re-litigate decisions in your head? The “woulda, coulda, shoulda” shtick. Most of the time it’s not a productive exercise, but it can be enlightening if you use it as a barometer to asses your tolerance for risk and openness to learn.

As you push the envelope you are going to make mistakes. Slip ups are part of being out of your depth and wading into new space. I’d argue that a life of zero defects probably means you aren’t experimenting enough.

Experimenting and trying new things means giving up some of the outcome control, but it also accelerates learning and exercises your risk muscle.

Look back and learn.

Keep showing up 

Persistence is the secret ingredient to long term growth. I’ll use writing as an example. Check out non celebrity writers on Twitter, Facebook, LinkedIn or WordPress. They write something most days (normally multiple things) and their followers start to expect a post on a daily basis. Some posts will be good, some brilliant and some forgettable – the point is that it’s dependable and persistent. Over time their readers see the musings and writings of the author as companion pieces to the day – like a morning coffee.

There’s the January gym crowd who start off with a bang and putter out around February, then there are the lifers who show up every morning and slowly get fit and stay fit. Lifers don’t have New Year’s resolutions because they have a standing daily exercise appointment that they don’t miss. It’s the same with writing. Never miss the appointment.

Persistence is underrated and underused because people think it’s obvious and table stakes for success. The reality is that most people give up early, so it normally does come down to the last person standing who gets the prize.

Show up every day. Persist

“Sometimes magic is just someone spending more time on something than anyone else might reasonably expect.” – Raymond Joseph Teller

Simple complexity 

Simple ➡️ Complex ➡️ Simple ➡️ Complex ➡️ Simple

Most things look simple from a distance. But until you understand the complexity, you can’t fully appreciate the simplicity. Go deep, get detailed and immerse yourself. There is simplicity and beauty on the other side of complexity.

Persistence and compassion are underrated

These lines in the NYT Michael Bloomberg interview resonated with me. It covers what I think is important. Persistence, compassion and hard work.

Who Gets the Job

What disturbs me is you talk to kids applying today and they invariably say, “I cured cancer, I brought peace to the Mideast.” Spare me. How about, “My father never existed, my mother is a convicted drug dealer. I worked three shifts at McDonald’s.” That’s the kind of kid I want — with an ethic of taking care of his family — because then he’ll take care of others. Some of us don’t have much prenatal intelligence, but nevertheless go out and try and have a decent chance of surviving. I’m not the smartest guy in the room, but nobody’s going to outwork me.

And he doesn’t look in the rear view mirror.

What I Would Have Done Differently

Given the way things turned out, nothing.

It’s a great interview. Read the rest here.

Shibui 

Shibui is a Japanese word that refers to a style that is simple, elegant, subtle, and unobtrusively beautiful.

I think that western culture is starting to appreciate the practice of shibui. In the way we live, in the things we buy, and how we spend our time. Just look at the elegant hardware coming out of Tesla and Apple, or Eichler designed homes in California with simple lines and natural light.

I love this trend.

Good Citizens and Mercenaries

Teddy Roosevelt said, “The first requisite of a good citizen in this Republic of ours is that he shall be able and willing to pull his weight.” A Good Citizen properly fulfills his or her role as a citizen. 

A mercenary takes part in a battle, but is not a national or a party to the conflict and is motivated to take part in the hostilities by the desire for private gain.

People, not product, will determine the success or failure of a company. You can have an excellent product and fail because you’ve assembled the wrong team. Building a business at scale is hard. It’s fraught with uncertainty, highs, lows, wins and losses. It’s an emotional roller coaster. Good citizens roll up their sleeves when there’s work to be done. They pitch up every day and are in service to each other. Mercenaries leave if it’s about anything but themselves.

The list of GC attributes I look for when building a team:

Compassionate

Collaborative

Curious

Comfortable with uncertainty and mystery. They feed off it and enjoy it

Cocky in a kind way

Gritty

Impatient

Kind

Loyal

Persistent

Pragmatic

Polite

Persuasive

Zen

Pointers for spotting a GC:

They use ‘we’ and “our” a lot when talking about solving problems

They laugh at themselves

Pedigree & degrees don’t matter. It’s about what you can offer now and in the future

They have a history of execution and getting things done

They listen more than they speak

They are self-aware

They are black belts in verbal judo. The best answer always wins the tussle

They ask for feedback, welcome it, and act on it

They have detractors. Probably a couple of bullies they’ve stood up to in the past

They respect the people they work with and are friends with them

They are rewarded and recognized by their peers

They offer up reference checks from peers and previous investors/partners

They treat interviews like a two-way street and ask questions about the team, motivations and product

They seek you out, vs. running away from their current role or company

They have hobbies outside of work

Ad hominem is not an option

They are comfortable making decisions with incomplete data

The understand the importance of luck, timing and preparedness

They are always learning, experimenting, tinkering & tweaking

Titles don’t matter

So what’s the opposite of a GC?

In my experience it’s the Mercenary. The are seductive, because they get things done, but don’t be fooled – when the going gets tough and it’s time to contribute to the greater good and sacrifice something…they leave.

Attributes that pop up time and time again:

Bully

Blamer

Bitter

Charming

“Lone wolf”

Poison dwarf

Rude

Short tenures and long stories

How to spot them:

They use “I” and “they” when describing their current role and company

They describe past and present colleagues as ninkanpoops/clueless/tone deaf/opaque/idiots/blind/wrong/lazy

They hold grudges

They “get things done” through coercion and intimidation

They stereotype people and roles

They don’t believe in luck and good timing. It’s all about talent & A players

They are “Remember whens” – “remember when” is the lowest form of conversation. They dwell on the past, live in the world of what was instead of understanding that things change and you need to move forward. (The Sopranos Season 6, Ep 15)

Listen for phrases like:

They don’t listen to me

It’s them not me

I don’t have the resources

It’s not my responsibility

You need me

I inherited that problem

My team wasn’t big enough

They wouldn’t promote me

I told them, but nobody listened

Give me people a chance to change

Everyone can change, and I’ve seen it happen many times. Sometimes Mercenaries become GCs and even inspiring presidents, but if it looks like a goat and sounds like a goat it normally is a goat.

Happy hiring!