Give Yourself Permission To Fail

Giving myself permission to fail has been a reoccurring thought as of late, and reading a recent post from CEO Michelle Wetzler really solidified it for me.

After a few years in the back seat helping others in the building process I am back in the founding position. As I get back into the drivers seat I am reminded that my mental approach to this next journey determines so much of my trajectory and overall success.

If I am scared to fail, I most likely will fail. If I am worried we’ll go broke, we most likely will go broke. If I think I am not good enough to be CEO and not fit to lead a successful company, I most definitely will be those things.

BUT if I reverse that thinking I can reverse the psychology as well.  If I believe I’ll be successful, I most likely will. If I am confident in our finances, we most likely will stay afloat. If I think I am good enough to be CEO and fit to lead a successful company, I most definitely will be those things. And if I open myself up to possibility of failure I see that it is not that bad.

Michelle sums it up perfectly.

Giving myself permission to fail has been one of the most liberating, stress-relieving, and rewarding things I’ve done in last year.

The only way we can become a truly great company is if we open ourselves to the possibility that we might not be.

And you know what? It’s okay if we’re not. If Keen busts, we’ll all find new grand adventures. Some us could start a new company together, or get boring jobs at big co’s, or sail around the world, who knows, the world is full of lots of amazing opportunities.

…To give yourself permission to fail, you have to untangle your ego from your work. Having your ego tied up in your work is a handicap. You can’t think strategically or take risks when you and your personal well-being are on the line.

Basically, embracing reality frees you up to be everything you were meant to be. By not being paralyzed by what could happen, you are free to create what should happen.

This is an important lesson for founders, especially first timers who fall victim to impostor syndrome. Wikipedia defines it as “a term coined in the 1970s by psychologists and researchers to informally describe people who are unable to internalize their accomplishments. Despite external evidence of their competence, those exhibiting the syndrome remain convinced that they are frauds and do not deserve the success they have achieved.”

Another way to think of impostor syndrome is to be so frightened by your future (be it positive or negative) that you simply don’t believe you are doing the right things or are the right person for the job. You question every little decision you should make, you aren’t sure if you should go left or right. You think your peers see a different version of you, a lesser qualified person sitting in the front seat pretending they know what they are doing.  You start believing you are an impostor and thus end up failing in the end.

This is all wrong and can be mitigated by giving yourself permission to fail before you even start. That way you are free to make the correct decisions, knowing failure is just part of the process. It sounds crazy but a simple change in perspective makes all the difference. I have found the best perspective is that the world is full of lots of amazing opportunities, and if you fail at this one there’s always the next one.

That, my friends, is why I am back in the drivers seat.

Coasting To Perfection

Am I doing all I can each day to reach my own pinnacle in life? Have I done everything possible to become the person I was created to be or am I just coasting along the highway…?

A post today piqued my interest and spurred this intense inner monologue. MG Siegler writes about a recent SI article on Michael Phelps which details his comeback and rehabilitation from alcohol related incidents.  The article touches on a variety of events in his career but what jumped out to me was a very interesting and possibly troubling assessment by Phelps himself, where he simply admits he has never given it his all. Ever. Even after numerous Olympics and all the medal records he feels he under-performed and still has his best inside him. Siegler ties that thought back to all of us:

“we don’t often hear about someone at the pinnacle of what they’re doing also failing to give their all — and yet, that’s clearly the case with Phelps….. And so in a way, I think that’s a more interesting point from which to look inward. If you’re really fucking up and squandering your talents, it’s pretty obvious for everyone to see. But what if you’re only not “giving it your all” and coasting on doing the minimum to still be successful — even very successful? Or maybe not even the minimum, but something less than all you’ve got. I think a lot of people are guilty of this. Maybe even most people. Certainly I am, in some regard.”

So I ask you, are you just coasting through your life?

It’s a troubling thought if you really consider the question when its asked another way: will you ever reach your full potential with your current output of energy, focus and determination?


I ponder this question quite a bit and maybe it’s the reason I have a number of current projects/companies ongoing in my life. It’s almost as if I can’t not do them. I don’t want to ever look back and realize I could have done more, that I should have applied myself more fully to the things and people in my life, and that I coasted lazily while others looked upon me with slight disappointment knowing I was fully talented and capable of greatness but in the end never doing anything worthwhile.

Wasted talent they’d say.

This is why I push myself to write even on days when I don’t want to or don’t feel like it. I want to follow my writing talent as far as it will possibly take me.

This is why I get in front of the camera and shoot more Founders RAW conversations.  Setting aside the enjoyment I get from doing them it’s not easy being comfortable in front of a camera and I believe people need to hear the messages we are putting out. I also want to follow my talent in media creation as far as it will possibly take me.

This is why I get on stage in front of hundreds of people each month and host Feature Friday events in Seattle – a monthly event which highlights 5 new up-and-coming area startups. This pushes me to become very comfortable on stage in front of crowds and calms the public speaking nerves, a wise move given public speaking is the #1 fear in the world.

This is why I push myself to build new apps and create whole new companies. I don’t ever want to find myself out of the loop on the latest trends, as well as sometimes it just takes a few cycles before the big idea takes hold.

This is not rocket science but I do these things so that I get better at them until a time comes where they are second nature to me. This is the 10,000 hours stuff Malcolm Gladwell talks about. It is said by the time the Beattles led the “British Invasion” with Beattlemania and brought their music into America they had already played together as a band live so many times they had eclipsed their 10,000 hours threshold and were very very tight as a band. That’s why they were so damn good so early on.

But it didn’t come overnight.

The Beattles believed – as I am starting to now – you are only as good as you choose to be. And “to choose” means you determine to do whatever it takes, however long it takes, with whatever means you have at your disposal to achieve you potential. Anything less is just cheating yourself and the greater world in the process.

Some have it easy you might say. They are naturally talented and without doing EVERYTHING THEY CAN they turn out to be Olympic champions and record setters. LeBron James, Michael Phelps, ect.. Simply more talented than anyone else. I say good for them.

But I am more impressed with the one who wasn’t God gifted with the most talent in the world yet works so diligently at their craft they become one with it, they become the legends we read about. The Wright Brothers. Steve Jobs, etc. The ones who came from nowhere, with no money and no connections, no Ivy League schooling, no Silver Spoon or lucky sperm club card to show off.

These people will it into existence. They are the ones we love to read about and crave to hear speak in public.

My guess is you fit that bill just as I do. So do yourself a favor each day and ask yourself if you are giving it your all – and be honest with your answer. My guess is you’ll be surprised at how much farther within yourself you can dig.


I am in the middle of a massive mental overhaul and it feels great.

Not that I really felt I needed it or was in danger going off the cliff, but I understand continual refinement is one of the secrets to life so recently I pushed into hitting a greater mental/emotional/professional learning curve.  With that I will say I think it’s time we start taking back our minds and not walking around the world like brainless mummies.

You are in charge of what goes into your mind and what you think about. It starts with what you choose to pay attention to and let into your conscious – subconscious even. If the brainless mummy comment was a bit harsh… well that is exactly what the media thinks of you.

I am talking about the news (industry in general) and how much of a bullshit clickbait crockshow it has become. Just look at a quick screenshot of today.

Screenshot 2015-11-17 at 2.03.07 PM

It’s as if CNN just reported on the end of the world.








That’s what’s going on and I am done with it. So should you.

News and media outlets have long left you in the dust and pretty much focus only on what will bring the most revenue in the bank. They show shock, terror and scare over anything else. It’s all about money and you are being poisoned in the process.

No wonder there are so many shootings and terrorist attacks around the world now. If media stopped reporting it maybe they would stop bombing buildings and killing innocent people since their names wouldn’t be plastered everywhere.

Maybe confused teenage kids who want their 15 minutes of fame on TV and social media would choose another path other than to walk into school and start shooting. But how did they get that idea in the first place??

Oh wait… right.

It’s a challenging topic especially now due to weekly terrorist threats and the latest Paris bombings leading to an unfortunate death toll numbered in the hundreds. My heart goes out to any affected. But it pains me to see this happening and only frustrates me when I see and hear about it.

It actually makes me mad. To the point where I might act on that anger. And that’s why I don’t do it anymore and for the sake of society I hope others do the same.

For an even worse stroll down scaryville-our-society-is-going-to-hell-in-a-hand-basket lane just turn on your local news. Murders. Rapes. Kidnappings. Robberies. Fires. OMG. We have a responsibility to take control of our thoughts and emotions, and never-ending scare tactics meant to keep us glued to the TV or computer screen do not help us achieve peace of mind.

You know what does achieve peace of mind?

Reading positive things.

Meditating each day on the good you will do in the world.

Spending quality time with loved ones and friends.

Putting the newspaper down, shutting the TV off, clicking off the website and then going out to do good in the world.

Go to work and do your part to move the world forward, no matter how big or small your impact may be. Don’t worry about missing out on events in the world – the important stuff happening around the world and in your own city will find you. Until it does, protect your own mind and spirit with all you have since that is all you have.

This I know for sure: Making your own world as positive and generous as possible starts with shutting out the negative messages of the media, which starts in your mind and that is 100% under your control.


The Tales We Tell Ourself About Failure

One thing we humans do really well is self doubt.

In the last week I have had two separate conversations with fellow founders about the grave situations their companies are in, how they are staring “defeat” right in the face and don’t really see any other option than to move on.

Both people are down and out right now.  And rightfully so… They have put years of blood, sweat, tears and money in pursuit of their dreams. They feel troubled with the fact that they didn’t succeed in the way they felt they could, didn’t build a meaningful and growing company. I know what they are going through, I have was there a few years ago and had a hard time knowing when it was time to pull the plug.

My advice to them is this:

It’s okay. You think the company (and you) are a failure because you have to move on and go do something else. You may have put your self worth into the company so much so that as the company faces a failure in operation you are feeling like a failure in life. You might be feeling a bit embarrassed because of all the things you said to your friends, family, coworkers, and industry partners now make you look at best untrustworthy, and at worst fraudulent.

These are all normal fears and feelings. They are all accurate and a normal part of the grieving process of a failed attempt at a startup company. But these are all fairy tales we repeat internally.


The reality is the very fact you set out and tried something unique and different is the success in this story. The very fact that you had the courage to attempt something most people would be afraid to do is the success. The fact that you were looking to be part of the solution rather than part of the problem is the success. Most likely your entrepreneurial decisions inspired at least one other person to jump up and start their own entrepreneurial journey. And further, maybe that person and their project turns out to be a massive success, impacting millions of people around the world, lots of that due to you. You may never know… but it’s a possibility isn’t it?

Many people lean on the stat that something like 75-90% of all startups fail, they don’t reach a point of self sustaining profits. I feel this stat is misleading since it only measures financial outcomes of each entity. Is the company alive, or dead? Red or black? Running or shuttered? Successful or not?

A better measure – albeit much more difficult – is to evaluate the impact each person and their endeavors have on the people around them. I guarantee if we were to measure the impact and success of each founder who ventures out on their own by looking at how they affected, influenced and inspired others we’d be talking about a whole different number. I bet it would possibly be the inverse, which would be quite inspirational. We’d be saying something like “Only 10-15% of startups really fail to impact the world so you must go and do it!”

To all those who are currently struggling with what to do and which decision to make for your company right now, heed this advice. The only failure in your situation would have been not choosing to attempt the impossible, since that is the only reason you are able to sit in the chair you are sitting in right now, reading this on your device you are holding in your hand, sipping the drink you are tasting right now, and driving in the car you just drove in.

Success is simply choosing to attempt the impossible and inspiring others to do the same.

Chop Wood; Carry Water

I recently sat down for a great lunch conversation with Nick Soman, a founder friend of mine here in Seattle.  Nick is the founder and CEO of LikeBright and a TechStars graduate.

As we were reminiscing about the founder life he said something quite profound.

Chop Wood; Carry Water.

It’s obviously a nod to early times in society where life depended on staying warm and keeping hydrated.  People couldn’t just hide in their cave if something went wrong, they would eventually die.  Or if successful, they couldn’t just rest on their laurels when something went right.  Simply put, life goes on. They needed to keep chopping wood and carrying water no matter what.


I believe that thinking applies today.  Actually, the principle applies even more today than ever since we have so many distractions in the palm of our hands and right in front of our faces.

If you have experienced something exhilarating, exciting and greatly advantageous for you or your business, the question is what do you do next?

You need to chop wood; carry water.

If you are down and out, struggling with life and fighting the feelings of disappointment the question is what are you going to do tomorrow?

You need to chop wood; carry water.

The point is you need to stay alive.  You need to keep working.  You need to keep doing what got you that advantageous opportunity in the first place.  And if you have hit a negative streak you need to just keep going, things will come back if you get back into the game and work on the basics.

Successful people make it a habit to be steadfast in their ways – they don’t get too high when things go well and they don’t get too low when things get challenging.  They stay even keel.

They keep chopping their wood and carrying their water no matter what happens to them.

I like that.  And it’s what I have been telling myself lately as I have been enduring some exciting times.

I hope you do as well.

Pedigree Is BS, You Must Work Harder And Smarter

I read an interesting article about Silicon Valley and its everlasting issue with founder bloodline/pedigree and their increased likelihood of success.

Indeed, the notion that anyone with smarts, drive and a great idea can raise money and start a company is a central tenet of the Valley’s ethos.

Yet on close inspection, the evidence suggests that the keys to success in the start-up world are not much different than those of many other elite professions. A prestigious degree, a proven track record and personal connections to power-brokers are at least as important as a great idea. Scrappy unknowns with a suitcase and a dream are the exceptions, not the rule.

Do I disagree with the general theme of the article?  NOPE.  Actually, it’s pretty much what I have been saying for quite some time now.  In fact, one could point to my clear lack of “pedigree” as a reason why I wasn’t able to secure seed capital for my startup Seconds, leading to Startup Death Valley.

But that is not what want to cover here.  There’s no reason to complain about the pedigree issue at hand – it makes logical sense just as breeders/gamblers look for strong bloodlines in horse racing.   Venture Capitalists are basically gamblers, and they will indeed bet on the person who has a leg up on the competition.  “He comes from money so he can support himself during the early times while they are working on the product.”  “He’s more connected so he’ll have an easier time attracting talent.”   He worked at Google!”

It all just makes sense.

Today I want to talk about what the other 95% of us out there need to do in the face of these realities.

Pedigree is BS.  If you are sitting here today with a less-than-steller history,  you cannot do anything about it now.  What’s done is done and you drew the short end of the lucky sperm club stick (whatever that may be…)

So forget about it.  Life is not fair and we all need to get used to it.

Yes, the pretty girls get asked out more often.  The good looking guy with nice hair and muscles gets the girls.  AND the Stanford grad that happened to get hired at Google has a better chance at raising money and attracting talented developers than you or me.


So what to do?

You need to get to work.  You need to work harder than others.  You need to work smarter than others.  You need to GO AND DO SOMETHING so that you IMPROVE your pedigree.

The thing about “pedigree” is it’s fluid.  It can change based on your performance in life.  You are not a predetermined soul in this world, destined to one outcome or another.  Existential and uber-religious arguments notwithstanding, you are free to make your own decisions and completely change your “pedigree” in life.  You can climb up into other classes/pedigrees.

I am sure you think pretty highly of someone like  JK Rowling, who is responsible for the Harry Potter series and now worth almost a $1 billion.  But, you may or may not know she came from modest means and actually struggled mightily in adulthood.  From wikipedia:

Seven years after graduating from university, Rowling saw herself as “the biggest failure I knew”.  Her marriage had failed, she was jobless with a dependent child, but she described her failure as liberating:
Failure meant a stripping away of the inessential. I stopped pretending to myself that I was anything other than what I was, and began to direct all my energy to finishing the only work that mattered to me. Had I really succeeded at anything else, I might never have found the determination to succeed in the one area where I truly belonged. I was set free, because my greatest fear had been realized, and I was still alive, and I still had a daughter whom I adored, and I had an old typewriter, and a big idea. And so rock bottom became a solid foundation on which I rebuilt my life.

During this period Rowling was diagnosed with clinical depression, and contemplated suicide.  It was the feeling of her illness which brought her the idea of Dementors, soul-sucking creatures introduced in the third book.  Rowling signed up for welfare benefits, describing her economic status as being “poor as it is possible to be in modern Britain, without being homeless”

Surely you know the rest of her story.

Pedigree is BS.  You simply must work harder and smarter than others if you want respect and the attention from important people.  You need to be willing to do what others aren’t will to do or haven’t even thought of yet.

1) If you don’t know anyone, make it a habit to get out and meet people.  Go to events, shake hands, book meetings often, and generally do good things for people.  They will start to know you better.

2) If you aren’t known for anything, START SOMETHING.  Also, start writing or creating media of some sort and start pushing it out on social platforms.  Trust me, if it’s unique and good in any way people will pay attention and start recognizing you.

3) If you aren’t from family money, BE GLAD.  The bulls-eye is not on your back.  Use this to your advantage and be stealthy in what you do.  And when YOU DO SOMETHING, you will come out of nowhere and surprise people.  Then they will start looking you up on LinkedIn and want to connect with you.  You will be the next “up and comer”.

4) Embrace a work ethic.  Since you don’t have a solid “pedigree” behind you, you will need to instill a strong work ethic into your life which will pay dividends later in life.   A strong work ethic is one of the best attributes you can have in life, and not being born into silver spoons allows you to develop it and take ownership of it as you mature into adulthood.

I recently read where Naval Ravikant, founder of AngelList, said something to the extent of “build for the longterm, no one really understands what the compounding effects of 10-20-30 years will do to a business and a career.”  Well said. I believe NOT coming from means plays into ones advantage because they are not part of the  “rich and lazy” bunch and thus will continue to work hard once they summit the first big mountain of success in their life.

Now put your boots back on, grab your ice pick and keep working.

Image courtesy of Flick chriscom.

The Value of Youth Sports In Startup Founder Success

A few recent conversations have turned towards youth sports participation and the valuable life lessons they provide.  One in particular stood out to me – youth sports participation is one of the best training grounds for a startup founder.

How would I know?  I was a competitive athlete pretty much since the time I could run, competed up until college and still remain athletic and competitive today.

soccer1Although I didn’t necessarily know it at the time, as I was playing youth soccer, basketball and baseball I was adequately preparing myself for a life long battle in the business world.  Learning to cope with immense challenge and competition is paramount to a person’s ability to achieve success.

I am so grateful for the experience and for my parents not forcing me into any specific activity, but rather allowing me to participate in a number of sports so that I could further develop my athletic ability, maximize my leadership skills and mature enough to determine which sport I more fully wanted to pursue.

It turned out it was Soccer, and it’s crazy to think back and imagine me as an 8 year old running around in a grassy field on an early Saturday morning thinking I’m just having fun when in actuality I was taking in and absorbing lessons which would help me in my life 20, 30 and 40 years down the line.

Below are just a few ways youth sports help develop a young energetic child into a strong willed startup founder.  I thank John Cook of GeekWire for the conversation that sparked these thoughts.


One of the first things you learn as a young athlete is how to play as a team and how to become the best teammate possible.  No soccer team can win with one person trying to play alone – teams must be able to depend on their offensive players, their defensive players and ultimately their goalie to perform to their best ability.  Players must be willing to step up and take the shot, yet at the same time be able to support and assist their other teammates if the organization is going to function properly.  This requires youth to understand which is which, and the appropriate timing of each decision.

Companies are the same way, they aren’t built by one person. Startup teams must be well rounded, supportive and willing to do whatever it takes to achieve success – for all members of the team.  That, or the team won’t exist.


Even at the earliest of ages sports teams will vote on a player to become captain, basically naming the leader of the team.  I believe this is the single best thing we (should continue to) do for our youth.  Captains are usually the more talented of players, have wide ranging experience and are outgoing and not shy in their ways with others.  But most importantly they are willing to take on responsibility.  They must lead the team, delegate when appropriate and stand up for a teammate if something goes wrong.

I believe giving responsibility as early as possible is one of the best ways to develop great leaders.

Imagine the lessons a 10 year old is learning as they lead their team during youth competition.  He/she is learning the basic tenants of team leadership, things they can apply to almost any endeavor.  In short, they are the on-field CEO and the success or failure of the team will rest (at least somewhat) on their young shoulders.

I cover startup leadership quite a bit so if you are a regular reader you will know my basic thoughts on the subject.  Simply put, startup CEO’s need to take full responsibility for their organization from day one.  They must wear the captain’s band on their sleeve in plain view so everyone knows where the buck stops.  This is not for their ego; it’s for efficient and effective organizational structure.  Why should an employee ask 3 people a question when really they should go directly to the decision maker to get the best and quickest response?  If employees in a startup don’t know who the decision maker actually is, whatever startup they are a part of ain’t gonna be around very long.


I get it, losing is not why we play the game.   Go visit a sports park on a weekend and watch how kids react to losing nowadays.  Yet losing in sports – just as in life – happens.  It actually happens a lot.  Learning to fail gracefully is a huge lesson any person, especially for someone thinking about starting their own company.

Why am I telling you failing is good for children?  Failing, maybe even getting injured  in the process, and then getting back up and trying again shows young athletes that if you do not quit then each new day is a new opportunity to win.  Losing teaches children not everything in life is guaranteed.  In fact, it teaches us more often than not things will not go as originally planned.  Sometimes shit hits the fan and you need to retreat and regroup to determine your next move.  There’s your basic “strategic thinking” lesson in action, a skill founders must employ A LOT.  Losing teaches youth hard work is required to experience success against your competitors.

This is essentially the experience of any early stage founder.  Startups fail most of the time.  Using lessons from our youth we can realize we just need to get back up and try it again, and hopefully we learn something in the process.

Enduring Hard Work

Finally, part of learning from failing is gaining the endurance to last long enough so we can experience success.  I distinctly remember our training sessions during soccer season.  They sucked.  Even if we weren’t going to be the best in the state of Washington (which we were 3 out of 4 years) we were definitely going to be the most in shape.  Coach made it very clear we would be the team with the best endurance around.

So we ran.  A lot.  We ran until we dropped, and then we ran some more.  We learned to embrace hard work and earn our success.  We learned anything worth winning was worth enduring tough challenges and the hardest of practices.  It was our standard and we embraced it wholeheartedly.  We spoke it.  We lived it.  We practiced it and we played it.  No wonder we won the state championship 3 out of 4 years I was on the team.  It was in our our DNA and our blood.

Startup founders need to take ownership of their future.  They simply need to determine where they are going, commit to a standard and uphold it no matter the cost.  They need to bleed confidence to the point where their success is inevitable.  They need to work harder than their competition.  This doesn’t mean work the most hours as humanly possible, that would be as dumb as our soccer coach running us until we all pulled hamstrings, eliminating us from competition completely.  Startups must figure out how to work harder but also work smarter.   Determining and following quality performance standards will do wonders to founders and their startup teams.

Youth sports are fun but they are also incredibly valuable to our society.  If you are a parent I would encourage you to place your children in a positive environment where they can develop leadership and success skills as early as possible.

Just like you.

The Real Killer App For Founders – Connecting With People

During my latest Founders RAW conversation I was talking with Patrick Henley, founder and CEO of Amp Tab when he mentioned something quite profound.

Connecting with people – truly connecting with someone – is the key to business success.

It was a great moment in the conversation (will post the conversation when it goes live) but I want to riff on the concept of connecting with people and why it can have a huge impact on your success.

Some may view networking as cheesy, uncomfortable and a waste of time.  I don’t.  And neither did Patrick.  Networking is not an activity, it’s an purposeful energy.  Patrick says connecting with people has been the difference maker for him and his success in sales and business in general.  He pointed to how connecting with someone on a deeper level, figuring out how he could help them in their pursuits tightens the relationship between him and the other person.  Once tightened, those people will break down walls to help you.

So how do you really connect with people?

Shaking their hand.   Looking them in the eye when they are talking to you.  Remembering their name.  Making them feel like they are the most important person in that room at that specific moment. Asking what you can do to help them.  Asking if you can introduce them to someone they are looking to meet.  Following up with them via email the next day to book a meeting or re-confirm what was talked about. These things show the other person you have their best intentions in mind, rather then trying to get something out of them.

Remember, people care more about themselves than others…  take advantage of that and let them know you too care about what’s important to them.

All too often people go about their days and nights looking to get something out of others.  This is a terrible mistake, just as it is for the guy at the bar who obviously is trying too hard to take any girl home.

Once people feel you have their best intentions in mind, they let their guard down and feel safe to further communicate using all the different means we have available.  They will then be willing to add you on LinkedIn, twitter, Facebook and others.

Do that year in and year out and before you know it you have a large network of people who not only feel comfortable with you but would be there when you need a favor (and you know that time will come sooner than you think) and willing to bust down walls to see you succeed.

This is the killer app for founders, creating a network of people you are truly connected with on a deeper level than just a digital click on a social network.  If more and more people can hear your name in public and think “man, that person is great and I would do whatever I can to see them succeed” you are golden.

It means you are truly wealthy in the relationships you have built.  And since success in business is based on the relationships we have created you will have no other option than to continue on your path towards success.

Blood + Sweat + Tears + Code + Polish + Sales + Luck = Startup

Startups are tough…..  Here’s a simple equation to get you headed in the right direction.

Blood + Sweat + Tears + Code + Polish + Sales + Luck = Startup


Blood – Like an initiation to a gang, founders basically cut their hand and make their pledge to build a successful company.  No Blood, No Commitment.

Sweat – A massive work ethic and a JFDI attitude  will be required to break down all barriers and knock down all doors along the way.  Better bring your gloves, water bottle and a sweat towel.

Tears – You will feel pain.  You will cry.  It’s ok.  A better way to think about it is if you haven’t cried because of your startup experience you are on the road to nowhere.  Comfort doesn’t equal success.

Code – Something needs to be built and someone needs to code it.  Piecing together other services or just pulling API’s is not defensible long term.  Figure out what you – and only you – can create and then protect the IP.  Once you build the secret sauce you can outsource all other technical needs of the product.

Polish – Design is quickly becoming the great differentiator between the good, the bad and the ugly of technology.  User experience, or how the end user interfaces and understands your product, should be your number one focus.  If a user doesn’t enjoy using your product why should they tell their friend to use it?

Sales -Plain and simple, customers pay the bills.  A startup’s need for sales and marketing talent is still undervalued in today’s technical heavy Silicon Valley.  Minus a large investment, your startup will wither on the vine if no revenue is ever generated.  And if VC’s ever do invest they will want to see revenues, so either way sales and marketing are a core function of startup success.

Luck – Perhaps the most important of all is luck, which unfortunately is out of the hands of the founders.   But the saying goes “you make your own luck” so being in the right place, at the right time, in the right market, talking to the right people and releasing the right product all can be influenced by the founders.  The more chances you take the more lucky you get so get out there and get discovered.

Pretty simple stuff.

Startup Growth Requires Making Your Own Luck

Great things don’t just appear out of thin air.   You have to nurture and cultivate them over time into what you envision as your dream company.

That, my friends, is the secret to startup success.

Yes, you have to build a solid product.  You will need to attract great technical talent.  You also need to have enough user engagement and financial capital so you don’t end up in Startup Death Valley.  But even if you have all that in your favor, luck is still required if you want to succeed.

Luck gives you the breaks you desperately need to go from a no-name into household name.

Seconds has been given an amazing opportunity to drive payments for a nationwide holiday event.  I will provide more detail as the event nears but suffice it to say this lucky opportunity is only possible because of what we have done over the past year.

It definitely didn’t appear out of thin air.  Day by day over the past year we made it happen.

Launch early

We launched the earliest version of Seconds about a year ago, under a different name and clearly aimed at a different customer segment.  The product was buggy as hell and to be honest, a bit embarrassing.  But that’s the point of an early release, isn’t it?  It does you no good to have an idea without a product others can touch, taste and see.  We knew we needed to get something into end-customers hands ASAP if we were going to receive any feedback – feedback that actually led to our next iteration.  I consider it lucky we were able to have a team willing to quickly put out a buggy product and gain much needed feedback.  In fact, we created that luck by committing to releasing immediately and listen to the feedback.

Speak loudly

Not surprising, I like to write.   Also not surprising, I like to write about Seconds and payments in general, on this blog as well as others more well known.   For a number of reasons, I believe this is why we are in the position we are in now given we have only been around 12 months.

If you search Seconds, we come up fourth, above the fold, right below a Wikipedia entry for the time interval and a few links to a movie also titled Seconds.   This is huge, as early feedback on the name was something akin to “great name, but how are you going to be found in Search?  Pretty tough huh?”  Well, that’s where writing comes in…. the more links to a website the more “relevant and valuable” it is in the search index algorithm.   I have no idea how many links are pointing to Seconds but it’s quite a few, based on how many articles I have written as well as how many others have written about Seconds.  This tactic also has helped Seconds gain media attention a lot earlier than other startups in the same situation.  At least we had something written about us and our vision the media could go off of, even if it’s from the founding team.

Founders need to speak loudly about what they are doing.  If you don’t, why should the media?  Getting your word out and better positioning your product are a few ways to create your own luck.

Spray widely

Discovering product market fit is probably the most challenging task for an early stage startup.  It’s one thing to sit at the white board and determine your products are meant for __(whatever)___ market; it’s a whole other ballgame once you get outside the office and try to grow a customer base in that market.  Not so easy…

Seconds is a payments system, a mobile focused one at that.  Amazingly, almost every industry and market vertical handles payments in one way or anther.  This poses both a great opportunity and a large problem.  The fact that our larger market is HUGE is quite the opportunity.  The challenge is trying to serve everyone right out of the gate, which is pretty much impossible.  So we spent the last 8 or 9 months spraying our message quite wide, gaining attention from a number of customer bases.  Some turned out well.  Some did not.  But the incredible thing is we have continued to learn from each and every customer discovery conversation, resulting in refinement of our pitch, company positioning and – at times – the very essence of our product.  Ultimately, this practice led to a few very promising markets ready and willing to run with Seconds.

We refused to be boxed too narrow in the beginning, and it has paid off tremendously.  A year ago, we were a text ordering system for local restaurants, struggling to fit our solution to their non-obvious problems.  This winter, possibly millions of people will be using Seconds to make donations to an important cause with a few quick swipes of their finger.  Everyone wants their payment experience be easier and more enjoyable, especially when making a quick donation.

Are we lucky?  I would say yes.  Did we create this luck?  You bet. You can’t sit on your butt and think the world will come to you.  If you want the world, you need to go out and get it.

What I Learned At DEMO 2012

The DEMO conference, held each year in Silicon Valley, has been home to many successful product launches over the last decade.  I was honored to be in attendance this last week in Santa Clara and it did not disappoint.  For those who aren’t familiar with DEMO, it’s an event where scores of startups have 6 minutes to present their product on stage.  At the end, a few awards are given to winners voted by a panel of investors and journalists.  The trip was actually the winning prize from the SURF Incubator pitch competition we won in June.  Before I go any further I want to publicly thank SURF Incubator for the opportunity and I hope we represented you well.

Although we didn’t present or pitch on stage I definitely had a great time.  Here’s Ray Kurzweil speaking on what he see’s as the future of technology.  Things are about the get crazy cool and I’m very glad I was sitting there that day!

The event – one I won’t forget for a number of reasons – was notable, tiresome, and educational.  We spoke with a number of other startups and were shocked at how strong our pitch has become, even to other entrepreneurs.  It’s pretty cool to see others grasping your concept and actually wanting to use it themselves and integrate within their offering.  The trip in itself was very travel intensive, which takes its toll on you mentally and physically.   We spent way too many hours on public transportation, that’s for sure.  But the biggest thing that stuck with me was how much you can learn by just observing people.  As I closely watched the presenters, I noticed a few things that I feel are not covered enough in the media, lessons us “early stage” founders desperately need.   I realized by following a few simple principles any founder can successfully demo their product and impress an audience.


The truth is, as an attendee watching all the DEMO’s you get quite restless and bored.  This is natural when you are indoors seeing 75 companies parading across the stage throughout the two-day event.  As a presenter, you must understand people are drawn into passionate communicators and distaste anything boring or monotone.  I watched most of the presentations during the event, and I was struck with how many presenters lacked expressive passion for their concept and cause.  They might have had some really cool tech but I wouldn’t have know it by how little they expressed their excitement.  Maybe they were nervous or something, but for whatever reason they did not positively influence me on what they were trying to DEMO.

To me, as an attendee, if the presenter did not elicit belief and passion as they spoke about their product, I tuned out.  It became background noise and monotone distraction to me and my iphone.  You think I am alone?  Occasionally I would glance around to the crowd only to see most attendees face lit up with some sort of device in front of them.  This is something all presenters should not overlook.  Today, you need to give people a reason NOT to grab their phone and play with it.  The best presenters were passionate in the right way, and helped me become passionate about their concept, albeit even for just a few minutes.  It’s notable to mention EVERY award winner passed my passion test.


In addition to passion, presenters must employ a great deal of poise when on stage in front of hundreds of people.  This is challenging yet probably the most important aspect of public speaking.  Face it, people are very superficial and if a presenter doesn’t come across comfortable, collected and confident the audience will immediately judge negatively.

The presenters that most impressed me were the ones that came across the most comfortable, confident and collected.  In a word, they were very poised onstage.  They told me, through their non-verbal cues, “I am the expert on this subject at the moment one the one you should be listening to.  Our market leading product is one you definitely need to check out.

Unfortunately, a few of the presenters actually froze on stage and forgot what they were going to say.  This is not a good outcome, especially when being onstage in front of investors and media could result in great fortunes for you and your company.  The result, for me as an attendee, was I didn’t really understand what they were doing (in addition to feeling really uncomfortable).  The result for them, probably very little investment leads.  Whatever it takes, speakers must get prepared!


Great product demo’s lead the audience on a journey of discovery into insights and personally useful information.  If not, it’s a waste of six minutes of a person’s time and attention (yes, this is what we all are thinking).   The successful demos all encorporated concepts or illustrations that instantly became relevant to me and others in the room.  One of the startups, StressFriend, has released an app plus wristwatch called Bandu that monitors your current level of stress and displays it in real time on the smartphone app.  Not only that, it maps my stress areas on an interactive map so I can see where I am stressed and where I’m calm.   It’s awesome, and something our society really needs so we can all just chill out!  During their demo, they actually had a drill sergeant come out from behind the stage, yelling and screaming in the face of one of their team members in the audience.  On the big screen, they showed his stress levels changing in real time.  Indeed, they were one of the award winners.  The relevance here is obvious; we all are stressed, we all hate raging people and we all felt it at that moment.  They brought it home!  You gotta believe very few people in the room were messing around on their phone or tablet during their presentation.

Winning pitch competitions can be the difference between gaining media attention and millions of investment dollars… or not.  It doesn’t have to be that difficult, you just need to follow a few major principles.  First be a passionate communicator so the audience feels you and your cause.  Second, be confident and have poise on stage in front of the crowd.  Lastly, no matter your product you need to present a story in which everyone can relate.  These three simple things will go a long way to help with your next demo and hopefully launch your startup successfully.

The Lonely Man On The Corner Vs. The Lonely Man On The Hot Seat

This is a re-post from something I wrote more than a year ago… 

See the lonely man there on the corner,
What he’s waiting for, I don’t know,
But he waits everyday now.
He’s just waiting for something to show.

Genesis – Man on the Corner

Disclaimer: What I am about to write is controversial.  As you read please remember this does not insinuate I lack caring in my heart for human beings of all levels of society.  It is merely my opinion of how a person chooses to live their life and what opportunities a person chooses to act upon.  There are no right or wrongs here, just observations and thoughts.  Also, it is important to note the thoughts below regard what people are choosing to do in the moment of poverty, not how they got into poverty in the first place.  I anticipate differing perspectives and opinions to be shared in comments.


You’ve seen him.  He’s the lonely man over there on the corner.  What he is waiting for nobody knows.  But he waits everyday, and he’s just waiting for something to show.  The quotes throughout this article are lyrics from a song Man on the Corner by Genesis. The video is below and it’s a must listen.   I recently listened to it and was shook by the emotions I felt during the song.  And so I started to think deeper on the concept of poverty.  I started to think about why some are rich; why some are poor; why I drive a nice car and some are stuck wearing the same clothes every day.  I asked myself, “what could possibly be the difference?”  And why some people find themselves on a street corner just waiting for ‘something to show’.  You may differ in your perspective on poverty in this country, but I believe poverty and entrepreneurship are distant cousins.

This man chooses to sit on a corner and hold a sign.  He has nothing (at least from what we know) and feels his best option is to do nothing, look desperate, and ask for money.  His value proposition rests on the morality of another person feeling remorse when they pass him, forcing themselves to face their inner soul and ask “am I a bad person if I turn my head and don’t give him money?”  He wants to be given something for nothing.  He takes from the world, but does not give in return.  He offers no product in which a dollar value can be placed on it and he has no service to offer another.  He just sits and asks for help.  He has chosen to do nothing.

And nobody knows him,
And nobody cares,
‘Cos there’s no hiding place,
There’s no hiding place – for you.

Genesis – Man on the Corner

I will juxtapose the man on the corner with the man in the hot seat.  What is the difference between the man in the image above and the man in the image to the left?  The man in the hot seat has, in theory, the same intentions as the man on the corner.  He is asking for money and he is looking for help.  He believes he cannot make his dreams come true unless he receives a gift from someone else.  His future, indeed, depends on another persons good faith.  But that is about where the similarities end.

For those have not picked up on it, the man in the image at left is a person pitching Paul Graham (an investor in the red shirt) on a business idea in hopes he will invest money towards his vision.  But in contrast to the man on the corner, the man on the hot seat does not believe in handouts or in receiving something for nothing.  He believes in creating value through enterprise.  He knows that if you have something, anything – a product, a service, a distribution channel, knowledge, land, a water source, natural elements, really anything – you can offer it to another for a profit.  He chooses to live his life working hard to add value to society, not take away from it.  He has taken ownership and responsibility for his life, understanding he can choose to do anything he wants with it.  But with that decision he knows it is up to him, and only him to make it happen .  The man in the hot seat is an entrepreneur.

Looking everywhere at no one,
He sees everything and nothing at all – oh.
When he shouts, nobody listens,
Where he leads no one will go – oh.

Genesis – Man on the Corner

At times entrepreneurs find themselves looking poverty straight in the face.  It might be in a situation where their income (or lack thereof) cannot fulfill the demands of their debts, whether it is a roof for shelter, food for sustenance or gas for their travel.  They choose to risk their current stability for the return of a better life.  There is an eerie aspect of entrepreneurship and I think it’s due to its distant cousin of poverty.  The mere thought of poverty can be the biggest moving force an entrepreneur receives.   It is incredibly scary and immensely motivating at the same time.  Only in risk one really experiences reward.  So we endure the possibility of poverty for the reward of wealth.

For the record, I am quite privileged to have a roof over my head, food to sustain my health and a nice car to drive each day.  I am doing fine but at this point in my life I hover right above to line, choosing to forgo a stable job for a chance to determine my own destiny.  Also for the record I have stared poverty in the eye and experienced what it could be like.  I have had my electricity turned off and creditors calling my phone for not paying bills on time.  I have had to dig change out of my car to buy a $.99 hamburger.   As a late-twenties ambitious entrepreneur who hadn’t “made it” yet – old enough to be established on my own but young enough to have not built sustainable wealth for myself – it’s was a tough slog.   I’m a tweener as they call them.

When you leave a stable financial situation and leap towards your dream, you risk falling into poverty.  Or should I say you learn how to operate with poverty as a strong possibility in your life.  You learn how to acknowledge where your responsibilities lay in the equation of life.  You start to realize your decisions will make or break you.  It is through this experience I start to think about poverty in a new way.   Whenever I drive by the man on the corner, I cannot help but think: “I could be out there right now.  That could be me.  As I am sitting here in my car it is unbeknownst to me how I will pay rent next month since I just took the leap and started my life as a full time entrepreneur.  But I will find a way.  I will find a way to not only pay rent but to grow my business as well.  I will choose to do something, not sit and do nothing. ”  I argue it is at this point of realization you really become an entrepreneur.

So Here’s the difference between poverty and success:

Man on Corner waits; man in hot seat acts

The man on the corner waits for something to fall into his lap, hands or box.  He takes no responsibility for his actions and believes by just waiting, help will find it’s way to him.  The man in the hot seat acts, on everything.  He believes it is through doing something, anything really, value can be created.  And when he creates value, wealth will find it’s way to him.  It is by doing and acting we entrepreneurs find success.

Man on corner values nothing; man in hot seat values everything

The man on the corner values nothing, not even himself.  If he did value himself, he would be doing something other than sitting desperately on a corner asking for a handout.  He has lost the ability to place value on anything in his life, thus has nothing.  The man in the hot seat values everything, especially himself.  He has such a belief himself he is asking others to invest large sums of money into his enterprise.  And he believes so strongly in himself he knows he can bring the investment amount times X back to the investor.  It is through immense value in self an entrepreneur will be successful.

Man on corner plays victim; man in hot seat plays hero

The man on the corner has ultimately bought into the victim mentality, meaning their outer circumstances determine their inner self worth.  A victim does not take responsibility for actions and outcomes, therefore they do nothing to change their circumstances.  The man on the hot seat understands it is he who determines his destiny and thus plays the hero.  A hero understands they are unique and hold power to orchestrate a positive outcome for all involved.  By believing you as an entrepreneur are the hero, your self worth has nothing to do with outer circumstances.  This frees you up to act according to your vision and experience success.

I am not sure Phil Collins would agree with my interpretation of Man on the Corner but I am curious if you do.

How Those Of Us Not Named Mark Zuckerberg Can Still Be Successful

A recent post on Business Insider by Rishi Chowdhury titled “Being a Young Entrepreneur” got me thinking about being young, being entrepreneurial and the affect it has on how others view us.

Chowdhury maintains since it is much easier to start companies today, we are seeing many more founders in their late teens and early twenties emerge with significant web products.  This has happened because they 1) come to coding and technology more naturally, 2) have the free time and 3) have less in their life weighing them down.  He notes:

It is also more common place to see teens who have taught themselves code and are able to create innovative web apps due to the freedom they possess. As this generation has grown up along with social networks, they know how to leverage these. What may start out as hobby/after school project can turn into a real business.

That’ s the upside, easily being able to start a company.  He then goes on to illustrate the difficulties in being taken seriously and actually building a company at such a young age.  I fully agree with Rishi and whatever the challenges he sees ahead, based on his writing I believe he has a great future ahead of him.

But what about those of us who aren’t Mark Zuckerberg, who didn’t trip onto a great idea in their late teens and now have more wealth than we ever imagined?  What about the guy in his mid-late twenties, who isn’t seen as the next “wonderkid” but cannot seem to shake the entrepreneurial bug that chases him everywhere he goes?  How about the people out there who don’t know how to code, have never actually created a web app but still dream of building a great business?

I believe sometimes we can be too hard on ourselves.  I think we look at the lucky few and think “geez, that guy is like 5 years younger than I but he is one of the richest people in the world!  How did he get so lucky?”  This is not the right perspective.  Mark Zuckerberg is an exception, and an outlier who has skewed the tech founder perspective

It is still harder than ever to create a breakout business.  Actually, it’s quite a bit harder than it was 10 or 20 years ago.  Why?  Because when it’s extremely easy and cheap to create a new web/mobile app, thousands and thousands of people do.  And when so many more people get involved, the market gets overcrowded.  When the market gets too crowded it becomes incredibly difficult to stand out and be discovered by enough people to achieve a critical mass of users.  Today, you must be very good at what you do to make it big.  Quality now matters more than ever – quality in product as well as quality in person.

So how does one go from a non-technical industry to becoming a tech executive?  Or put another way by Rishi: “A big consideration when starting your company while still very young, is how are you supposed to be taken seriously as a young entrepreneur?”

Well, my advice to Rishi as well as all other entrepreneurs: Be an exceptional person.

1) Build yourself as you build your company

From this day forward and for the rest of your life, you will be interacting with older, more educated and much wealthier individuals.  Sorry to tell you, but they usually will decide if they want to work with you within 5 minutes.  The trick is to quickly impress on them your strengths and abilities, usually within the time it takes to finish your elevator pitch.

This can be the biggest obstacle of all – your personal presentation – especially if you don’t have the luxury of saying “oh, and I’m a Harvard (or Stanford) grad.”  How much time you devote to development of your wisdom, knowledge, wit, personality and social skills will be obvious to businessmen, CEO’s and investors the moment they meet you.   I am a firm believer you can really move forward in life by polishing yourself each day.  No one should ever leave the student mentality.

A few ideas:

  •  Audio learning whenever possible- I listen to Stanford ecorner podcasts each week and it’s like I am in the class.  I also listen to ITconversations when I am driving.
  • Read books like it’s going out of style – business, tech, personal development, fiction, etc…
  • Get uncomfortable and reach out to people whenever possible; learn from each interaction

2) Build your network as you build your company

I cannot tell you how valuable “the network” is, and I am referring to the professional networks like LinkedIn.  Whatever you choose to go with, reaching out and connecting with well established people validates you as a professional.  Once you get connected (via email, phone call, mutual friend into, etc…) immediately book an in-person meeting.  Overlooking a personal meeting is the biggest mistake most young (or less connected) people make today.  Put bluntly: virtual connection does nothing but link you with someone else.  To leverage the connection, you must sit eye-to-eye, open yourself up and let the other person get to know you so they actually understand how to best help you.  This can only happen through in-person meetings.

A few ideas:

  • Reach out to your local tech network and introduce yourself to others in the community
  • Ask to have coffee and meet them in person.  Interview them and write about it!
  • Build out your LinkedIn connections, more people validate you with it than you might think

3) Build your vision as you build your company

There is something magical about hearing someone describe a vision of how they intend to change the world, especially if they are younger in age.  Doing this separates you from the crowd so when you do connect with others they will remember you and your unique vision.  Who wants to listen to someone says “oh, we’re the guys doing daily deals for X industry”?   They most likely won’t remember you or what you are doing with a vision so undifferentiated.  Get passionate, creative, and innovative around something new and start talking about it.

A few ideas:

  • Look at industries which haven’t been fully transformed by the web and search for pain points
  • Take the long view and have courage to paint a unique vision, tell the people you meet about it
  • Use “the network” to find others who share your vision, they might just turn out to be future partners

I understand it’s difficult to be taken seriously as a younger founder because it’s the same as a (relative) newbie to the tech scene, and I’m just barely out of my twenties myself.  We are not Mark Zuckerbergs, who seemed destined to create the next big thing.  But it also doesn’t mean you are any less qualified to lead a great organization.  It just means you have some extra work ahead of you.  And as an entrepreneur, that shouldn’t come as a surprise.