My Photo

Lijit--Search Everything Here

Recent Posts

July 17, 2017, 09:20:05 AM

The Uninvited Silent Partner That Haunts Every Success

Last week, I was invited to speak at Montreal’s seventh annual StartupFest, perhaps the continent’s most important gathering for emerging business ideas and those who want to invest in them.  

Like other events of its ilk, the mood at Startupfest covered the entire spectrum of optimism, from wide-eyed hope to bubbly euphoria, and this year’s event theme--Lucky 7th--served to top it off with an additional sprinkling of unicorn dust.

This is why I felt it necessary to turn the tables a bit, and deliver a somewhat contrary cautionary tale as my contribution.  Here it is verbatim:


So tell me...why are you here at this conference?

You probably all share the same reason--you’re chasing the dream, the big win, the home run.

And on this journey to your promised land, you’re learning so much.

How to pitch.  How to get funded.  How to scale. How to get acquired.  Those aren’t just concepts, but actual titles of sessions here.

But one lesson you’re not learning is the dirty little secret that as build, establish and grow, there’s a silent partner stalking your every move.  Yup, every move.  Every one of you.

Worst of all, he doesn’t rear his ugly head until you actually attain your dream.

His name?  The Devil.

This is not a joke, and shouldn't be taken lightly.

Trust me, when you close your big deal, when all the money’s tucked away in the bank, before you even take your first step, The Devil is there smiling, hand extended to shake yours...and demand his 10%.

Just when you think you’re invincible, invulnerable, that you finally made it big, The Devil will be there with a kick-in-the-gut reality check.   

Ask any successful entrepreneur.  I can name dozens of household names I discussed this with, most recently Shopify’s COO Harley Finkelstein. Like all of them, he just shook his head sadly in agreement.  On a personal note, the challenges I faced after bringing Airborne Mobile to a nine-figure exit were greater than those faced while building it. The Devil’s handiwork--bad luck at best; disaster at worst--awaits every big win.

Sometimes, it’s self-inflicted:

  • Hubris
  • Drugs
  • Alcohol
  • Gambling
  • Poor decisions
  • Wild egomania

Sometimes, it’s out of your hands:

  • Mental health problems
  • Sickness
  • Jealousy
  • Family breakups

But whether you suffer personally or observe as a weakened, wounded bystander, The Devil’s always by your side.

You may say: “Hold on, this isn’t unique. Sickness, addiction, jealousy...come on, that stuff happens everyday!”

True, but the difference to a winning entrepreneur is that they’re on such a high, they’re blindsided, they don’t see it coming.

But it does come.  And it will come.  It’s not a question of “if,” but “when.”

This "Devil as your deal’s silent partner" is an important cautionary tale. Everybody lives through it, but nobody talks about it.  Until now.

So be smart; put the Devil in your cap table.  Give him his own line: Satan--10%.  If nothing else at this point, it’ll at least make your investor pitches and board meetings more intriguing.

So as you grow your business, you may not need to make a deal with The Devil.

But if you get to the promised land, you will most definitely have to deal with The Devil.

Consider yourselves warned.

Godspeed to you all.