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.

Playing The Field Vs. Sitting On The Sidelines

I had a few great conversations this morning and although they both happened independently there was a similar theme to the conversation.

I found myself thinking “I would rather be a player on the field than sitting on the sidelines.”

We were talking about how its such an awesome time in our society and such a great time to build a technology company, and the thought just hit me.   I don’t want to be 50 yrs old siting there reminiscing about how back when I was 20 people started walking around with these things called cell phones.

“Son, back in my day them people used to dial a number and actually talk to someone through that there handset” I imagine I would be saying to my kids.  “now look at all the things you kids do on those damn things.  If I would’ve just been a little smarter and started something of my own I would been a millionaire… “

NO.  I would rather tell my kids “…. and you know what, I chose to jump into the game and ride the wave of innovation rather than watch it go by.  And It’s the been the best decision I ever made!”





  The Player








The Fan





Being a player means actually getting your butt off the sidelines and into the game.  It takes a lot more energy for an athlete to play in the game than for a fan to sit a watch.  And you wonder why athletes are paid so much money?  Ever try to get out in front of millions of people and catch that touchdown pass before it flies by your head in a split second… its tougher than you think.

It also takes courage to put yourself out there and compete in the game of business.  Yes, you might fail.  Yes, you will probably screw up the play.

Yet, it’s 100 times better than being a monday morning quarterback like all media outlets tend to do.   And at least you are out there making something of yourself and hopefully adding value to the world.

It seems funny to me how crazy excited and into professional sports some fans get.  What do they actually gain when their team actually wins?  Besides beating the Vegas odds, not much.

Being a player is tough but it’s also way more exciting.  Have you ever thought about what happens if you actually succeed?  Who knows… but indeed it will be more than the satisfaction of your team beating the other team on any given Sunday.

Look at those two images and ask yourself which one you want to be.

The Start It Series: How To Build A #Winning Team

Start It is a documentary series on how Order SM, an early stage mobile commerce startup, is approaching the launch of their company.  It is intended as a helpful guide to anyone looking to build or grow a startup in today’s fast paced technology space. 

What you read may counter “generally accepted” startup practices in Silicon Valley or elsewhere but that’s what happens when you are a bit different. We are not Stanford Grads; we are not ex-Googlers; we are located in Seattle, not San Francisco; and we did not start off with a large network or initial funding sources. We are 21st century entrepreneurs and this is our story.  It’s a good bet most of you are none of those things either so we hope this may help you get off the ground.  Please feel free to reach out with comments or questions.  This is the second of many posts in the Start It Series.

In the previous post How To Establish A Vision Worth Pursuing we covered how important vision is to the  success of startup.  You really need to know where you are going before you start the journey.  But once you figured that out,  the next question to ask is Who will go with me?  Or more importantly, what do I actually need to get done and who are the right people to help make it come true?

The story of the 1980 U.S. Olympic Hockey team can teach us a lot about leadership and team building. The movie Miracle details how the coach Herb Brooks (played by Kurt Russell) led the 1980 U.S. Olympic hockey team to victory over the seemingly invincible Russian squad. For many reasons Miracle is one of my favorite movies and Herb Brooks has been a great example to me of how to approach building a team.  His leadership approach is astounding as he prepares the team to take on what seems to be an insurmountable odds.  One moment in the movie stopped me right in my tracks.  Herb picks his team by bringing together a bunch of random players – young players and no-names –  going against the wisdom of his assistant coaches and team advisors.  The conversation went something like this:

Herb’s assistant: This is the final roster?  You’re kidding me, right?  This is our first day, Herb. We’ve got a week of this. What about the advisory staff? Aren’t they supposed to have a say in this?  You’re missing some of the best players.”

Herb responds: I’m not looking for the best players, Craig. I’m looking for the right players.

The last sentence says it all:  I’m not looking for the best players, I am looking for the right players.  You get a sense Herb knows what he is doing and understands just who should be in each position.  He had spent countless hours studying the opposition and knowing EVERY player he might possibly have on his team before he actually knew he was to coach the team.  Once the opportunity came to him he knew exactly which players were going to be on the team and why.  Ultimately, his strategy proved correct and his story illustrates why building the TEAM is one of the most important tasks a leader must undergo.

Counter-intuition, we see it all the time in sports.  Very rarely do “dream teams” with massive payrolls win championships yet most organizations try to land the biggest names and highest paid players.  Another great lesson can be observed in the recent movie (and book by Michael Lewis) Moneyball.  In the early 2000’s the average payroll of a Major League Baseball franchise was growing like a weed.  Oakland A’s General Manager Billy Beane came to realize if they were going to compete with the Yankees of the world, they needed to play a different game.  So he re-wrote the rules.

With a little “number crunching” help from his assistant he discovered success in baseball was not a result of big bats, MVP’s and inflated contracts, but actually due to higher on-base percentage.  Quite frankly, the more each player got on base the more likely he was to score.  And  baseball games are won by scoring more runs than the other team.  T

His assistant said: “Your goal shouldn’t be to buy players. Your goal should be to buy wins. In order buy wins, you need to buys runs.”

He started looking at the concept TEAM in a whole new way.  Countering the opinions of others and risking his job, he gutted the team of high-cost players and found younger, cheaper and more teachable players who fit into his game plan.  Like Herb, he didn’t want the best players he wanted the right players.  He the found players who not only got more done, but got it done at a tenth of the cost.  The A’s went on to win a record 20 games in a row and were one of the winningest teams of the 2000’s.

So my question, what is required for your team to win?  And who can just get it done?  Is it an all-start team or is it a team who can JFDI?  The founder who takes responsibility for forming a young team needs to have as much conviction as Herb when they are “picking their team”.  It’s easy when starting off to fall into the trap of looking for the best “dev talent” or “hot shot serial entrepreneur” when in reality you need to find the right players and place them in their correct roles.  Success for a start-up means actually launching a product and experiencing growth in usage.  This requires with speed and efficiency, and the optimal team is one where everyone plays a specific part for a specific reason so they can ship a product and grow a business.  JFDI.

Ask yourself: “Why do I want this person on the team and what are they going to own?”

I not saying don’t look for the best people you can possibly get.  Who wouldn’t want to have a team comprised of the best people you can find tackling a big problem?  Of course look for greatness in your people. But there is something counterintuitive about finding the “best”.  Unfortunately some of the best people around the world (in anything) are the most difficult people to work with.  At best these people are great at what they do and can really make a team shine.  But at worst, these people can become a cancer within the group and bring down the entire team.  It is the founder (leader’s) responsibility to make sure their company stays afloat and successfully gets to market .  You must mitigate as many risks as possible and because people can be one of your biggest liabilities, this issue cannot be overlooked.

The Startup Triad

If you are looking to build a technology or web startup you will mostly likely fall into the general founding position of needing a techie, a designer and a business guy.  Important: You may officially have more or less than 3 founders on your legal documents, that is up to you.  Why three individuals?  Why can’t a single founder do it all?  Well, most technical startups require specific skills and numerous areas of expertise.  It’s safe to say no one is great at all three descriptions and anyone trying to start something alone is wasting their time.  Do yourself a favor and find some complimentary teammates.

Here’s an approach to forming a solid founding team for those who are just staring out:

Founder 1: The Technical Engineer – the one who writes code and builds the product.

Founder 2: The UX Designer –the one who makes the product usable and look good from the end users point of view.

Founder 3: The Business Developer – the one who develops the business strategy and finds the money.

These roles are required to build anything that resembles a tech startup.  You need someone to think of the strategy, someone to build the product and someone to make it usable.  The key is finding the sweet spot where all three overlap.

Note: Don’t make the fatal mistake and think you can cut corners here.   As the leader, if you haven’t found someone for each of those 3 roles, drop everything and go find them.

The Order SM Founding Team – We have taken the triad approach to forming the Order SM team.

Jacques Crocker: The Technical Engineer

Jacques is an amazing Rails Jedi who worked hours on end to piece together Order SM earlier this summer.  He owns the code and with his expertise he has single-handedly changed the game by creating this incredible product.  Every startup needs to have a Jedi.

Gary Windels: The UX Designer

A extensive background in design has given Gary an eye for simplicity and elegance and is a strong compliment to Jacques’s engineering skills.  He always centers his designs on the end user’s perspective, and does so with well grounded reasons as to why design will make or break your product.   Every startup needs “end user eyes”.

Nick Hughes: The Business Developer

As the business developer I focus Order SM on value creation.  I answer questions such as “how and where does our technology add value to the current business ecosystem?”  “Who are our customers?”  Where are we going to find them?”  “How much does it cost to operate our product and can we create enough value to charge more than our cost?”  Every startup needs someone laser focused on the how, where and when of value creation.

Look for to the next post in the Start It Series, here is the previous post on vision in case you missed it.


Flickr image courtesy of chipgriffin