Now for the Hard Part by Bob Rosenberg

Now for the Hard Part

Marilyn Monroe had stage fright. Bad stage fright.

Before she’d go out to film a scene or face an audience, Marilyn repeated a mantra borrowed from a circus aerialist. She’d say to herself, ‘This next trick is impossible’, then go deliver one more extraordinary performance.  

It’s an entrepreneur’s trick, wholly different from ‘fake it ‘til you make it’.  A high-wire, daredevil move, but one grounded in experience, practice and the knowledge that preparation – and talent – trump fear.   One doesn’t fake it when there’s no net.

When you’re a start-up founder, you have to know – and respect – what you’re doing.  And be in constant learning mode.  

Because things change.

I talk a lot about risk – and how investors assess value by degrees of risk mitigation.  Is the technology proven?  Have customers bought the product?  Is the market large enough?  How are you going to sell/scale?  What are the likely competitive responses?  Are there potential acquirers?  How strong is the IP?  How good is the management team?

Good investors suss out all the holes – all the weaknesses, all the failure modes – in your business.  And if you’re not as aware of them as they are, and if you don’t have reasonable responses (even ‘we know we need to build a team of service representatives who speak multiple languages’ constitutes a reasonable response), investor confidence will wilt.  

Startups ARE impossible tricks, and you manage all aspects of the enterprise.  And because it’s a developmental process – and because humans are humans – the aspects change from day to day.  Key personnel leave.  Products have faults.  Deals fall through.  Employees screw up.  Cloud servers crash.  Customers are difficult, or welch when it comes to paying up.  Successful founders navigate an ever-changing set of circumstances.  Like an aerialist who must contend with unexpected winds, equipment failures, inexperienced gaffers.

All good, you say.  Nothing new here.  

Now here’s the real trick, the new, unpracticed trick.  Try to dance on the high wire when you have no idea of where you are and what’s coming next.  

Without a net.  That’s life this September as we return to reality.

Reality was more or less predictable a year ago.  Yes there were unexpected snafus and market surprises, but investors had stable models that allowed predictions.  And the market was a known quantity, evolving but reliable.  

We had confidence in our models, and our models gave us sufficient confidence.  

Welcome to a pandemic planet where the USA grows increasingly less reliable, neither partner nor protector, where Brexit looms and budget deficits have exploded, where the free flow of people and knowledge is under attack.

Where, as the economists say exogenous risk has gone through the roof.  

Talk about ‘this next trick is impossible’ – founders and investors alike wake up from summer slumber on the beach to a cold and forbidding September reckoning, a back-to-business that forces us all to be working without a net.  We need to be better prepared aerialists, more daring, more flexible.  

This September’s promises no performances for the faint of heart.

As always, let me know if you have questions or want to talk startup or most anything else.

Be safe out there.

Bob Rosenberg

Educator (Associate Professor) / Entrepreneur / Leader of angel communities / 
Entrepreneur in residence at PorterShed and BioExcel



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