If you tell the story of a startup, you’re describing how a small group of people with talent and insight and energy are making decisions in an environment that they cannot possibly understand.  This series follows the story of Vinny, the founder of early software startup, though his trials and difficult judgements.  It begins when is a new business leader in Detroit and ends in the brief period when he is king of all that he oversees.

Cast (in alphabetical order)

  • Sahara Ale                       Jessie
  • Margaux Amie               Violet
  • Zoe Anastassiou            Madison
  • Debbon Ayer                  Karen the Banker
  • Ron Bianchi                    San, Rick and Thomas
  • Geoffrey Grier               Vinny
  • Josh LaForce                   Carl, the VC
  • Noah Masur                    Curt & the other Rick
  •  Jake Minevich                Dennis & Julio
  •  Cariad O’Brien              Molly


Leaving Detroit (1)


An Ordinary Story.

Or It Should Be Ordinary.

A young African American entrepreneur, maturing business in bad times.  

  It’s not easy.  It’s not straightforward or as rational.  Over the next 7 episodes, we will look at our long term CTO, Vinny, make decisions about his original startup.  

Vinny is making these decisions under duress, which doesn’t help.  His wife died just as he was starting his company.  No one trusts him to make good decisions.  And he’s not sure that he can make them himself.

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Getting Funds, Losing Friends (2)


Finding investment.  

Accumulating Capital.

Never as easy as you think.   It’s not the technology.  It’s the business.  And the two are often far from the same thing.  

And when you go from technology to business, you often find decisions that are hard to make.    Our Podcast CTO, Vinny, is building his first successful startup.  In the process, he is offered the opportunity he has long desired but it comes with a decision that he wished he did not have to face.  
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Who Gets Represented (3)

hwms.coverartThey’re just a bunch of old guys, right?  The board.  The board that is supposedly guiding your company.  Who do they represent?  And why don’t employees get automatic representation on the board?  All are tough questions.

In theory, and the theory is fairly broad, board members represent no one.  They are supposed to put aside their individual needs and desires and decide what is best for the organization.

But broad theory and narrow practice can be quite different, or at least that is what Jessie believes.


Temptation, Technology & Easy Money (4)


What’s success?  A million a month? A million a month in revenue for a young software firm? (Remember, this story comes from the 1990s, Podcastland.) It’s not a bad start.

But what do you do with success? Throw a party? Lease a new office building? Build your technical staff? Listen to your board and take a stab at controlling the market?

Such is the problem faced by Vinny, the CEO of SidePocket. He doesn’t know what path to take even with the siren call of temptation sweeps through the air.


Against the Board  (5)

hwms.coverartSometimes talk doesn’t work.

You’ve argued your case again and again. They hear your points, concede your argument but don’t accept your conclusion.

What do you do? And when do you do it?

And perhaps most importantly, what do you tell yourself about the risk involved? A key moment in the development of SidePocket.


The Challenge (6)

hwms.coverartIt’s not a typical employee relationship – CEO and Board.

Sure, there’s an employee contract but it hardly covers all the circumstances of the job.

Vinny, the CEO of SidePocket, has concluded that his board is out of step with the software market and that he needs to take firm steps to show them a good strategy.  These steps will put him in conflict with the board, but it is an uncertain conflict.  He’s not directly disobedient.  Yet, he is not following the board strategy either.


Closing Shop (7)

hwms.coverartThe arc comes to a close, even though the issues remain open.   At some point, the board has to make a decision – Take the path to the right, Take the path to the left, or Stand in the middle of the road, (which is a decision unto itself.)
Vinny’s board has taken the “maximize immediate return on investment” path, which was the obvious choice once they understood the situation.  The decision brings the SidePocket story to a close because there is no more SidePocket to discuss.  However, it leaves at least on human open, unresolved and visible for all to see.


The Corporate Goddesses