I recently sat down with serial entrepreneur Jordan Weisman for a Founders RAW conversation and walked away a changed founder.  As we cracked our beers and adjusted our mics – we hadn’t even yet turned on the cameras – I asked him to give me a brief overview of his entrepreneurial journey.  Here’s a rough summary of what followed:

So I started out trying solve problem X…. that didn’t work.  So we tried something else…

Next, we founded a game company.  That was bought by company Y.   Boy was that crazy..

After that, I started a few more, one was sold to Disney.  Another I sold to….and  so on and  so on.

In total, Jordan has founded 14 companies over the course of his entrepreneurial life.  Many failed.  Some very much succeeded and you could sense he was very content with his journey.

I really wish we had captured those few precious minutes on camera!  I wish you could have heard it – and seen my face – during the conversation because my jaw was dropping lower and lower each time he said the words “…and then I started” and followed them up with “and that was sold to...”

It was during that specific moment I was struck by something very powerful, I realized I was grasping a strong lesson right then and there.  Of course you are going to feel like a failure if you start one company and it doesn’t work out.  But the truth of entrepreneurship is it’s a numbers game.  Or said differently, if you take just one crack at it most likely you are going to fall flat on your face.  But by simply getting back up and trying again you greatly increase your odds of succeeding.

At risk of sounding naive, pollyanna and cheerleaderish, I want to bring up a really important point.  The irony is the most successful people in our world have failed more than many of us, sometimes more than many of us – combined.  We all have seen the old Nike commercial where Jordan describes how many times he failed, yet he still is arguably the most successful athlete we’ve ever seen.  He says: “I have failed over and over and over in my life, and that is why I succeed.”  

Look at any billionaire founder (outside of Mark Zuckerberg) and you will see someone who did not make it on their first try at business.  Or second try.  It might have even taken them 3, 4, or 5 starts before the big one hit.

This is not a “let’s all grab hands, sing kumbaya and make each other feel better for failing” type of post.  This is about absolute truths of the world, and ones which are hard to truly understand when you find yourself in challenging moments.

The lesson here is all of us founders must understand the first few times are the most challenging.  If you didn’t achieve what you set out to achieve in your current startup, statistics tell you to try again.

Does a gambler in Vegas take just one shot at the craps table?

Was your your first job the best and highest paying you have ever had?

I am guessing no.  So don’t think your first startup is going to be your best.

During another recent FR conversation, Matt Schobe told me it took starting 2 other companies before starting Feedburner, which in the end sold to Google for $100 million.   Would you grind away at two tough startups before a third one gets acquired for nine figures?

I sure hope so.

And a subtle but important footnote in that story is Dick Costolo.  He was part of all of those attempts – there during the tough times and challenging days – which in the end led him to Google, and then on to Twitter where he is now CEO.

Oh and he recently took Twitter public, minting him many more millions in the process.  I am wondering if he would be there today if he quit after the 2nd failed startup?

Here’s Jordan’s advice to first time founders.