When Losing is Winning

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.

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Being a Founder is easy…

it’s actually properly executing and growing the vision (being a Finisher) which is extremely hard.

To every dreamer I have known
May Lady Luck take you home
I pray for every wannabe
Dreamin’ big and livin’ free like me

Kenny Chesney “Like Me”


As an entrepreneur and founder, I can relate to Kenny Chesney’s words in his song Like Me, from the album The Road and the Radio.   Along the road of being a Founder you meet a lot of wannabees, dreamin big and livin free.  Being a Founder, by definition, means all you have done is starting something.   You are a dreamer, thinking of all the ways the world could be better with your new  idea, software, device, app, project or team.  Founders are great and we will always need Founders.  In fact, every company ever started has had founders.  Apple.  Google.  Microsoft.  Facebook.  They all started with an idea from the mind of one or two people.

Founder –noun

a person who founds or establishes.


Finisher – noun
a person who brings (something) to an end or to completion; complete:


But what about being a Finisher?  Take a look at those simple definitions once again.   Founder starts – Finisher completes.  Seems to me Finisher’s are a lot less celebrated in our society, yet they are equally if not more important than a Founder to the success of an enterprise.   A finisher enables the project to be completed.  They lead the team which launches a new product or service and makes sure it gets into the right hands for success.  They are the one who establishes the appropriate processes so the system can function properly.  They line up investors for future growth or acquirers to fulfill the liquidation process for early stakeholders.  In short, Finisher’s complete what a Founder has started.  And in the end isn’t that what matters?  It is interesting that a Founder can hold a majority equity stake in company, but only earn his wealth if a finisher is present to help bring things to fruition.   Let it be known, some Founders are also Finishers, but it is extremely rare and it takes a lot of resiliency.  I would venture to say this is the main reason why the majority of startups fail to make it to “completion” – they in fact had a Founder, but no Finisher.

There are a lot of Founders in this world, for which I are thankful for since innovation starts with a vision.  But I think the world needs a heck of a lot more Finishers.  Which one are you?