Startup Thoughts > A Entrepreneurs Submission in Defence of Vulnerability and Insanity

Vulnerability sounds like truth and feels like courage. Truth and courage aren’t always comfortable, but they’re never weakness — Brene Brown

But then here’s the thing:  You have to push through discomfort to achieve any kind of personal growth.  You have to pass through the discomfort zone to achieve any change of significance. Here is a nutty yogi that’s turned a bed of nails into an environment for relaxation and meditation…who knows  what immense enlightenment he is achieving as a result…

Here is my general thesis:

Embracing vulnerability is key to great leadership.

Today I have been consumed with thoughts of vulnerability – not only how it applies to the very nature of being an entrepreneur and the fears we have to face on a daily basis.

So see this post as a bit of an adventure…you’ll be going down the rabbit hole that is my mind, which may at times be a little discombobulating!  But then my mission is to make you smile like Cheshire Cat, and as the Cheshire Cat wisely says:  “We’re all mad here!”…

So, where to start?

Would you tell me, please, which way I ought to go from here?”

“That depends a good deal on where you want to get to,” said the Cat.

“I don’t much care where –” said Alice.

“Then it doesn’t matter which way you go,” said the Cat

That being the case, and given we are both entrepreneurs at heart, I suggest we take the road less travelled.  It’s what we do, is it not?

My desire today to learn about vulnerability led me, rather randomly, to the late Oscar Levant – an American pianist, composer, actor, hypochondriac and world-class neurotic.

Yep, that’s him.  Not the prettiest of men, but talented in many other ways.  Look at that Cheshire Cat grin… (we’re all mad here…). Anyway, Levant once famously said:  “There is a thin line between genius and insanity. I have erased that line.”

As Levant saw it, this blur gave him creative impetus. But residing within such a blurred environment must have left him pretty vulnerable, no? But then I suspect it was his very vulnerability that gave rise to such beautiful art.  Vulnerability is the birthplace of creativity, innovation and change.

Could it be said that entrepreneurs, to a degree, share the same phenomenon?  To be fair, we have to be practically deluded to hold on to our dreams and vision despite daily setbacks, rejections and criticism… Is it courage, vulnerability, insanity or all of the above?

Imagine Walt Disney at the age of nineteen. His uncle asks him what he plans to do with his life, and he pulls out a drawing of a mouse and says, “I think this has a lot of potential.”

Or Springsteen. Apparently, he once told a story at one of his concerts about how he and his dad used to go at it — how his father hated his guitar. Late one night, Springsteen came home to find his father waiting up for him in the kitchen. His father asked him what he thought he was doing with himself. How does he tell his father, “I’m going to be Bruce Springsteen?”

Vulnerability comes from engaging in a contemplated risk that considers and hopes for the payoff, financial or otherwise will be worth the effort. Active vulnerability is in essence proactive and informed risk-taking.  And that’s what entrepreneurs do, right?

The willingness to be vulnerable isn’t driven by the desire for exposure, but by the possibility of what that exposure might lead to — be it a meaningful role, the possibility to affect change, and, or, greater financial gain.

Most people don’t like change.  Seeing the usual things happen for the usual reasons means there are no nasty surprises….Routine is comfortable, even if part of the routine is getting around the coffee machine and moaning about how terrible everything always is…

So when you dare to be different .i.e. to stop spectating and step onto that track and to start running…it’s not unusual to suddenly find yourself faced by a whole load of critics…


Who are we to challenge the status quo?  It puts others in the uncomfortable position of having to question why they are not following their own dreams…

Entrepreneurs make the deliberate choice to suck up the criticism and to plough on anyway.

True entrepreneurs are those who have decided to have the courage to do their “thing”, whatever that might be.  And yes, they do that despite being scared. It’s having the courage to quit stable jobs, and to face up to the naysayers who tell us we’re crazy or irresponsible or selfish.

It’s what Londoners call “BOTTLE”.

I don’t know about you, but I was totally blown away and obsessed with the London Olympics. As was the rest of the country…after years of moaning about the cost and inconvenience of it all, the Olympics captured everybody’s imaginations and left us all feeling proud of being Londoners.  We all cheered on our brave athletes and felt part of their success.

See the picture above?  It’s there to prove a specific point (other than that Jessica Ennis is hot!).  On the track, these athletes are fighting for their dreams. And around the track there are thousands of people watching other people fight for their dreams.

The point?

You don’t want to be an anonymous face in the crowd. You’ve got to face your fears, climb onto that track and start running.

Vulnerability is the birthplace of love, belonging, joy, courage, empathy, and creativity. It is the source of hope, empathy, accountability, and authenticity. If we want greater clarity in our purpose or deeper and more meaningful spiritual lives, vulnerability is the path.”

It may be less certain or well chartered, but guess what – by taking it, we will likely end up somewhere we have never ended up before.  Somewhere pretty amazing.

Perhaps we’re not so crazy after all.

Cheshire cat would be proud.

So I will once again leave you with one of my favourite poems – Invictus.  I won’t cherry pick lines, the poem is too good for that.  It merits coverage in full:


Out of the night that covers me,

Black as the pit from pole to pole,

I thank whatever gods may be

For my unconquerable soul.

In the fell clutch of circumstance

I have not winced nor cried aloud.

Under the bludgeonings of chance

My head is bloody, but unbowed.

Beyond this place of wrath and tears

Looms but the Horror of the shade,

And yet the menace of the years

Finds and shall find me unafraid.

It matters not how strait the gate,

How charged with punishments the scroll,

I am the master of my fate:

I am the captain of my soul.

Did you know that William Ernest Henley, the author of Invictus, was the inspiration for the character of Long John Silver in Robert Louis Stephenson’s Treasure Island, a Captain indeed?  Mad little fact…got to love the coincidence.  We entrepreneurs are fearless pirates, right?


Fifteen men on the dead man’s chest—

Yo-ho-ho, and a bottle of rum!

Drink and the devil had done for the rest—

Yo-ho-ho, and a bottle of rum!


Treasure Island is, of course, an adventure tale.  And you and I are on an adventure together.  One parallel I’d like to draw is that the story is also the story of one boy’s coming of age. At the outset of the novel, Jim is a timid child, but by the end he has matured incredibly. He has outwitted pirates, taken over a ship, and saved innumerable lives. Jim has become an adult in character if not in age.

Like any maturing boy, Jim must try out various role models. Jim’s father does not appear to be a significant role model: he passes away early in the novel.  Turns out Long John Silver was a pretty good role model.

Which leads me on to one of my favourite quotes of all time (and yes, the sailing references will continue…):

Twenty years from now you will be more disappointed by the things that you didn’t do than by ones you did do.  So throw off the bowlines.  Sail away from the safe harbor.  Catch the trade winds in your sails.  Explore. Dream.  Discover.” – Mark Twain.

The year Mark Twain died (1910), Theodore Roosevelt’s delivered his famous speech sometimes referred to as “The Man in the Arena”, was delivered at the Sorbonne in Paris, France, on April 23, 1910.

This is the passage that made the speech famous:

“It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better.

The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, who comes short again and again,

because there is no effort without error and shortcoming; but who does actually strive to do the deeds; who knows great enthusiasms, the great devotions; who spends himself in a worthy cause;

who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly.”

Vulnerability is not weakness, and the uncertainty, risk and emotional exposure we face every day is not optional.  Our only choice is a question of engagement.  Our willingness to own and engage with vulnerability determines the depth of our courage and the clarity of our purpose; the level to which we protect ourselves from being vulnerable is a measure of our fear and disconnection.

Rather than sitting on the side-lines and hurling judgement and advice, we must dare to show up and let ourselves be seen.  This is vulnerability.  This is daring greatly.

And when it comes to trolls and other naysayers, if they are not in the arena getting your ass kicked too, who cares about what they say.

You’re probably wondering where the sailor reference is with our friend Theodore…  Well first off Roosevelt was a sickly child who suffered from asthma. To overcome his physical weakness, he embraced a strenuous life. He attended Harvard University, where he studied biology, boxed, and developed an interest in… drum roll… naval affairs.

On the world stage, Roosevelt’s policies were characterised by his slogan, “Speak softly and carry a big stick”. A proverb advising the tactic of caution and non-aggression, backed up by the ability to do violence if required.  The term ‘Benevolent Dictator’ comes to mind…

The idea of negotiating peacefully, simultaneously threatening with the “big stick”, or the military, ties in heavily with the idea of Realpolitik, which implies a pursuit of political power that resembles Machiavellian ideals…oh that lovely topic of politics again.

Theodore happened to be the uncle of Eleanor Roosevelt, one of my female heroes.


Though widely respected in her later years, Roosevelt was a controversial First Lady for her outspokenness (a woman off my own heart).

She also said some smart things…which funnily enough tie in to everything I’ve been saying in this post:

People grow through experience if they meet life honestly and courageously. This is how character is built.

We gain strength, and courage, and confidence by each experience in which we really stop to look fear in the face… we must do that which we think we cannot.

Honesty…courage…hmm I’m sensing a theme. Oh and she also said this, which just made me laugh:

I once had a rose named after me and I was very flattered. But I was not pleased to read the description in the catalogue: no good in a bed, but fine up against a wall.

I will sign off now but will leave you with one last story.  Odysseus, the mythological adventurer, wanted to hear the mesmerising song of the Sirens, the evil bird-women who happened to have achingly beautiful voices.

But this was surely a suicide wish because the song of the Sirens was infamously irresistible and had lured countless sailors to their deaths on the rocky shores of the islands where they lived.

But you don’t get to sack the city of Troy without being a plucky and ingenious chap.  And Odysseus was determined to hear the Siren song without meeting his maker.  So, he had all of the men on his boat block their ears (but not his) with beeswax so they couldn’t hear the song.

Then he ordered them to tie him to the mast and not to untie him until they had passed by the islands.

And once in range he begged the men to untie him to he could get closer to the islands and the music.  The men steadfastly refused until they had long sailed away from the Sirens.  And thus, he was able to survive the temptations.  And go on to do more heroic derring-do.


Tie yourself to the mast like Odysseus and fix your aim on DOING.