SidePocket

It’s an ordinary story.

And perhaps a bit of a fantasy.

But perhaps our time  could benefit from an ordinary story.

A young African-American leaves Detroit in the mid-1980s to see what he might do in Silicon Valley and in the process, learns something about investment, governance and decisions (both good and bad).  Revisiting the audio drama of Vinny and SidePocket

Things sometimes go well.

Or so we hope.

Our new tech entrepreneur is in a new city with a new company, a new investment and a new start.

Maybe.

Or maybe not.

Vinny and SidePocket start operations in Silicon Valley.  The second episode in the audio drama.

Blame the bosses.

A tried and effective strategy.

And some times, it is actually true.

But grudges can blind our eyes, leaving us with a moment of self satisfaction and not much more.

Jessie misplays her hand

Third in our re-release of the audio drama: SidePocket

They make you work.

They take your money.

They expect you to like it.

But sometimes.  Sometimes.  There is another option.

A chaotic trip through San Jose suggests a new strategy.

Fourth in our re-release of the audio drama: SidePocket

Your face on the cover of a magazine.

What does it matter?  (Who knows what a magazine even is, anymore?)

Success has come to Vinny but how long will it stay?

Fifth in our re-release of the AudioDrama: SidePocket

Things are never as clear as they seem.  Never as obvious.  Never as straightforward as you would like.

It should be simple.  You get an idea.  You make a product.  You take it to the market.  Let your customers decide for good or for ill.

But that simplicity masks the fundamental conflict.  A conflict over goals.  A conflict that is often deeply hidden in the acts and decisions of daily life.

Cast members Caraid O’Brien and Josh LaForce talk about the current series of the podcast and the challenges of preparing a podcast while driving through the streets of San Jose, California.

You see the need.

You found a way to get the money.

You make the move.

You’re board doesn’t like it.

But you’re ok, right?  I mean, you did the right thing?  And your board will come along, don’t you think?  Afterall, you are innovating.  But then comes the break.

Sixth in our re-release of the AudioDrama: SidePocket

You must take the tide at its flood.

That is the sad lesson of organizational leadership.

You may like your colleagues.  You may like where you work.  You may even like what you do.

But there are times when you must loose the ropes that bind you to shore and start the journey afresh.

Vinny at the end of SidePocket

Seventh in our re-release of the AudioDrama: SidePocket

A young entrepreneur.

A new technology.

All the temptations to make bad decisions.

In the series of on the startup SidePocket, we explored the challenges posed by organizational governance, the authority wielded by investors. Our central character, Vinny, walks away from a company that was unable to make a decision and forms a new company, SidePocket, that will be under his leadership. He guides it to success but in the process has to face choices that have no obvious or unequivocally good answers. He builds a profitable firm but in the process, alienates his closest friend, reluctantly accepts guidance he would prefer to ignore and decides to sell the firm against the wishes of his board.

A series that makes you feel the problems of organization governance and appreciate the issues at stake.