After Growing Seven Companies Here’s a Harsh Reality Every Entrepreneur Should Know About Success


Talk to enough entrepreneurs over enough years, and some patterns get repeated over and over and over again.  One of the most prominent is the expectation of success.

Not just the expectation of overall success, but the expectation that the current plan is going to work as planned.

It’s not.

I grown seven startups of my own, helped 73 others through Fledge accelerator, have been following startup stories for over 25 years, and have built my whole career around understanding how to build companies.

What I’ve yet to see is any company that succeeded with their Plan A.

Your Plan is Wrong

If there is a trick to being a successful entrepreneur, it’s in understanding that your plan is wrong.  That even when you “fix” it, it’s still wrong.

Finding where it’s wrong is your first-and-foremost job.

This is true for your business plan in general, and it’s also true for most every small task you are working on this week.

That newsletter you just sent out… the subject line could have been better.

The last sales call that didn’t end in a sale… there’s a better way to explain your offering.

Your website needs another round of edits or a redesign.  That last management meeting wasted a lot of time.  Etc. etc. etc.

In the last few years I’ve repeated the same basic conversation with a dozen different entrepreneurs.  The pattern was identical.  Their business did not perform up to their projections and expectation.  Because of that, they slowed down or stopped their communications with me and their other advisors.

They were embarrassed for not meeting their own expectations.

The Same Advice

Each time I gave them the same advice:

“I’m an entrepreneur too.  But what I know that what you are now learning is that plans don’t always go as expected.  In fact they never go as expected.  I know that if you are only telling me good news, then you are not telling me the whole truth.  Your investors know this too.  Every early-stage investor knows that things go wrong.  So what you need to do is brush yourself off, stop expecting nothing but success, and going forward tell us both the good news and bad, and ask us for help to overcome that bad news.”

This is a hard lesson to learn.

No one wants to fail.

No one plans to fail.

Yet ever success is full of small failures.

The difference between overall success and overall failure is whether you have enough persistence and resources to overcome these small failures, and whether you have your eyes open looking to prevent any big, company-killing failures.

Stop expecting success.  Start expecting failures.

If you want more we recommend you check out Shark Tank’s Robert Herjavec’s One Key Rule For Success

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