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.

Founders RAW is BACK!

After a year long break, I am excited to announce we are back to filming more Founders RAW conversations.  We filled our need for a new film crew with the addition of Shinebox Films and quickly got to work to complete two new conversations.

For the uninitiated, here’s why I started Founders RAW:

“Founders RAW is actually an experiment.  As founders of an early stage startup we quickly realized how difficult starting a company can be.  And being part of the larger startup community in Seattle we discovered we weren’t alone in our crazy, mind-blowing experiences – apparently others have them too.  The idea started to form once we noticed the frequency of finding ourselves 30 minutes deep in truth sharing and wisdom dropping conversations with founder friends.  We wondered if others would be interested in what we have learned, so we figured why not to bring a camera.  I guess we’ll see what happens.

Founders RAW is a video blog with conversation style interviews focused on bringing out raw stories early stage founders experience in their challenging entrepreneurial journeys.  We invite founders to talk openly over a beer or a coffee about the “truth” of how they survive and grow their companies.  We post the full conversations on the blog but really, who has time to watch 45 minutes of video?  So we slice up the conversations and post nuggets each day as well as send out daily videos no more than 3 or 4 minutes long to blog subscribers.    Now we all can receive daily nuggets of the entrepreneurial truth.”

This year’s guest’s will include founders from Ghostruck, Unikrn as well as a prominent Seattle Angel Investor along with others to follow. You will see more on those when we complete the editorial process, but I wanted to highlight a handful of conversations we had over the last few years to get you back in the mood.

Brewster Stanislaw, cofounder of Inside Social

Marc Weiser, Founder of RPM Ventures

Simon Crosby, Founder of Bromium

Adam Lieb, Founder of Duxter

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.

Some Awesome New Resources For An Entrepreneur’s Daily Learning

No one knows it all.  When it comes to startups and entrepreneurship things seem to change so quickly generally accepted conventional wisdom is actually becoming obsolete before our very eyes.

For that reason I strive to stay up to date with the industry, what’s taught at the major universities like Stanford, and what young founders are learning in accelerators like YCombinator.

Here are some resources I have been using recently to gain more insight as a founder and entrepreneur in the tech industry.

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The Stanford ecorner is something I have been listening to for almost 6 years now.  They record one speaker each week addressing the class and then post it to the site the next week. Topics range from Creativity & Innovation, Opportunity Recognition, Product Development, Marketing & Sales, Finance & Venture Capital, Leadership & Adversity, Team & Culture, Globalization, Social Entrepreneurship and Career & Life Balance.  Stanford University’s Entrepreneurship Corner offers 3000 free videos and podcasts, featuring entrepreneurship and innovation thought leaders. I highly recommend it!

downloadStartup Class – Stanford CS183B, taught by Sam Altman of YCombinator.  CS183B is another class taught at Stanford. It’s designed to be a sort of one-class business course for people who want to start startups.

Videos of the lectures, associated reading materials, and assignments will all be available here. There will be 20 videos, some with a speaker or two and some with a small panel. It’ll be 1,000 minutes of content if you watch it all.

Screen Shot 2015-01-16 at 2.51.05 PM (podcasts) is a new resource put together by Jerry Colonna and his business partners.  Jerry Colonna is an executive coach who uses the skills he learned as a venture capitalist to help entrepreneurs. He draws on his wide variety of experiences to help clients design a more conscious life and make needed changes to their career to improve their performance and satisfaction.   The Reboot podcast will showcase the heart and soul, the wins and losses, the ups and downs of startup leadership. On the show, Entrepreneurs, CEO’s, and Startup Leaders will discuss with Jerry Colonna the emotional and psychological challenges they face daily as leaders.

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The A16Z blog and podcasts are one of the best new daily resources an entrepreneur can read.  As previous entrepreneurs and now some of the most popular venture capitalists, they provide their unique views of the technology market that will help any founder gain valuable insights on trends, investment thesis’ and the newest startups that are raising money and making a dent in the world.


The Secret To Launching A Successful Startup

What’s your secret?

In his book Zero To One, Peter Thiel asks the question “What one thing do you know that no one else in the world knows?  What’s your secret?”

The answer to that question is the secret to starting a successful company.

downloadWhat Thiel is suggesting is there are things in this world you observe, intuitively know and understand more than anyone else.  By peeling apart those layers and understanding where there could be value creation you will find the golden nugget.  Then it’s as simple as creating a new company, building the product and releasing it to the world.

What he is also illustrating here is that success comes from ingenuity and uniqueness, not copying others.  The world doesn’t need another anonymous messaging app or social network.

It needs your secret.

Do you realize there are things only you know about the world?  Most likely there things you continually notice about your everyday life, the city you live in or the technology you use that keep bugging you.  There are problems you continually encounter where you might be wishing someone fixes them.  Do you maybe see a better way to do them?  Do you keep getting frustrated at the same places and times each day?  There might be something you can do about it…

Once we come to grips with the magnitude of this reality starting a company becomes a lot different.  You now realize each and every one of us have the ability to create successful companies.  All it takes is a little focus and observation of the world around you, and then having the fortitude to create a scalable solution.

Today, think about what might not ever be created if you don’t build it?

Finally Emerging From A Founder Depression

At times we can be our own worst enemy.  The challenge is to minimize those times.

We often hear choosing to become an entrepreneur – and the life that accompanies it – is not for the faint of heart.  This is absolutely true.  But for the longest time I didn’t really understand what it meant.  Or moreover, I didn’t fully respect the ramifications of the simple choice of taking my entrepreneurial leap.

Yet now being on the other side of this experience, I understand on a deeper level what entrepreneurship all about, and how to best navigate through it the rest of my life.  As I describe some of my thoughts and observations, I hope they might resonate with you as well and help you through whatever your situation you might be in currently.

Entrepreneurs, by default, are high performers.  And high performers, by default, are hard on themselves when times get tough.  Combine those two and you could get a deadly combination.

Entrepreneurs hold themselves to higher standards than others and often are disappointed when things don’t necessarily end up as great as they had thought when they initially set out.  But you know what?   Entrepreneurship never ends up like you initially thought.  It’s messier than anyone ever imagines and more extreme than anyone ever describes.

After I experienced a failed startup I dropped into what I now can identify as a depression.  I was not – and am not – depressed as in the clinical sense, but it was more like what you would think when people refer to the last economic depression we recently survived.  It was temporary and externally triggered.  Things weren’t right and I was responding to them certainly in a negative and self deprecating way.

It was painful.  It felt troubling.  It sucked because I wasn’t supposed to be there.  Or so I thought.

What I discovered was I denied myself some truths I should have admitted at the time.  I wasn’t admitting things like: 1) I really didn’t know what I was doing, and neither does anyone else.  2) The business was not working the way we had positioned it.  2) Startups actually do fail!  3) It’s okay to walk away rather than being so committed to a project you drive yourself into the ground.  4) Your personal value is more than just your company’s success.

I did not admit those things and the result was just that – nose dive right into the ground.  Being a friend or family member you probably wouldn’t have known it by being around me.  I am a damn good actor.  I do a great job of burying the issue and grabbing another beer to selflessly talk about your challenges and issues.

Yet deep down inside was some of the worst self talk anyone could imagine.  I was not my biggest cheerleader, supporter, believer and best friend.  If you are wondering, negative self talk is not the path to success.

It took a few years to pull myself out of it.  It took me accepting the fact that although I knew I could be a great founder at some point in my life, now was not the time.  It took me putting my ego aside and accepting positions with other startups and companies where I could add value and learn more about building companies.

It seems elementary now, but letting go of the founder dream and using my skills in an another company was the farthest thing from my mind at the time.  It took me admitting I did not know it all and I need to place myself somewhere to both earn a living and learn more about the world of technology and growing a business around it.

This type of wisdom and perspective is almost impossible when you think you are worthless.  And that is exactly what people think when their startup fails.  They think since they could not make their own company work – one where they pretty much put every ounce of effort they possibly could into making it work – what’s their value anywhere else?  This and other similar thinking is obviously incorrect and ill applied.  Yet, I am telling you this is exactly what I and other founders find themselves thinking.

I have since pulled myself back together, landed a great position with another company here in Seattle and on the path to learning and earning!

The resulting mental and emotional clarity is refreshing. It has allowed me to stabilize my life and opened up space for other projects like Founders RAW, Coinme, and getting back to writing.  It has allowed me to establish myself as a mentor and advisor to other entrepreneurs, here and elsewhere in the world. It has allowed me to embrace and fully enjoy a meaningful relationship for the first time in a long time.

The lesson here is not that you can do things to avoid the founder depression.  More than likely it’s inevitable for you, me and every other entrepreneur.  The lesson is in identifying the oncoming founder depression, quickly observing its symptoms, and then finding mitigation strategies you can deploy to keep you afloat – and happy.

Entrepreneurship is not for the faint of heart.  But it is for the wise and honest.

3 Startup Principles Every Early Stage Founder Needs To Know

I recently gave a talk to early stage entrepreneurs at a weekend hackathon in Bellingham, WA.  It was fun, challenging and educational for all.

Given these individuals were just starting on their journey, I chose to focus on things they should be considering coming right out of the gate.  Below are the three things I addressed with them and what I feel every founder needs to think about as they hack together their team and build out a first version of their product or service.



The very first thing you must think about is your team – whom should be on it and whom shouldn’t.  Get it right or pay the price later.

Especially when you are starting something at a weekend event like a hackathon or Startup Weekend, it’s tempting to just grab abled bodies from anywhere so you so you can fill empty seats.  This is not advised, since the wrong person on a can bring down the entire ship.  It’s very important to fill specified roles within the team to put your company in the best position to succeed.

Here are the three positions I feel need to be filled if you are considering forming a team to build a software/app based startup:

The Developer.  First – and especially if you are starting something in tech – you’ll need a technical person.  This individual is the one who architects the product and who writes the code. Great engineers are able to balance pragmatism and perfectionism, are not averse to debugging and bugfixing, and employ a healthy skepticism of their code and the world around them. This is the engineer.

The Designer.  Second, you’ll need someone who makes the code look pretty, readable to the layman allowing for a great user experience.  Great designers understand that 90% of good design is not about the pixels, they understand basic coding and have a well rounded view of other sciences of the world.  This is the designer.

The Hustler.  Lastly you’ll need someone who can sell your product, or the one who understands how to get it in the market and found by people.  This is generally the business person, the CEO, and the Hustler.  To quote Fred Wilson, CEO’s really need to just focus on 3 things.  They set the overall vision and strategy of the company and communicate it to all stakeholders. Recruit, hire, and retain the very best talent for the company. And lastly, make sure there is always enough cash in the bank.  That’s the Hustler.

Fill those roles first, or deal with the consequences later.

Customer and User Validation


The second thing early stage founding teams need to think about is finding out who will actually use the product by doing customer discovery and validation.  The knee jerk reaction of most founders is to believe they are so genius they can think up an idea in the shower, grab a few developers to build the app and then sit back and enjoy millions of downloads from all over the world.


It’s imperative to get out of the door and talk to actual people who YOU THINK would be your end users.  You need to interview them, asking questions about what problems they are encountering, why they are having those problems and how are they trying to solve them today (they usually just piece together a few random tools to solve it until something better arrives.)  Figure out how they are doing it now so you can offer a solution 10x what is available on the market today.

And rather than trying to plan the entire thing out before talking to customers – like sitting in an office and writing a 30 page business – just start with a hypothesis, do some interviewing and testing on a few good ideas on how to solve it, and then adjust and pivot with the results you observe.  You will learn more in a week or two of testing hypotheses than months/years of preparing a well written business plan full of (mostly) wrong assumptions.

Do your customer interviews now or learn later no one wants what you just built.

Product Simplicity


The last one is a biggie!  It’s paramount a founding team understands their vision, know what they are trying to change in the world and then break it down into approachable pieces to start with.

As a founder you need to think about your entire vision as a large iceberg. The challenge is to find the tip of the iceberg and only release that as the first version. The rest of the iceberg is under water and very large, just as your entire vision is in your head and not visible to the rest of the world. Some think of this as an MVP (minimum viable product) and I concur, I just like the illustration better.

Most founders make the mistake of not finding (or determining) the tip of the iceberg and thus end up building the whole iceberg, resulting in lost time, a bloated product and a lost value proposition.

For every Uber – a very simple and easy to use app – there’s thousands of apps that get it wrong and initially build a too complex product. They end up confusing users and not even getting to the point of an exponential user growth curve.

Twitter was simply a status update and following what others were updating. That’s it and people could easily talk about it and share it with their friends. Snapchat was pictures you could send to friends that disappeared after 10 seconds.  YO was absurdly simple, yet at least it was simple enough where millions of people got it and downloaded the app to mess with friends.

The key is to break down your complex problem into its essence. Know the end game and the large vision but find the simple starting point where millions of people will understand what to do with the app. Find the least amount of features and code possible to solve your initial problem.

These three principles are essential to a successful product launch.  If not paid attention to they will hinder a startup team from building a product, launching it successfully and achieving any traction in the market.

The #2 Founder Sin is Getting Married On The First Date

Would you ever consider marrying someone after the first date?

Thought so.

Since we are on the topic of Founder Sins (you can read my first one here) let’s talk about the second one real quick.  Another very common thread I see fraying from the rookie founder sweater is how quickly they are considering whom to choose as their cofounders.

“I met this developer at a networking event and I think we’re going to build something together.”

“Do you know anyone who codes?  Do you think they could help me with my idea?”

“The six of us started a company at a Startup Weekend!”

I hear these all the time.  It’s not a bad idea that people are “hustlin” and looking for skilled people to build out their team.  It’s just that it ain’t easy.

Just as dating the right person takes time for the relationship to develop into a marriage, so does a business partnership.  I am not saying you need to “court” the person for years on end, but I am saying it takes more than one event, one week or a few short meetings to grant a random person a large stake in your future company, basically legally binding the both of you.

Las Vegas Welcome Sign 3/30/11

Here’s why I know.  I have lost a cofounder myself.

In the fall of 2011 I was approached by an awesome developer – whom I didn’t know at the time – about joining the founding team of his newly forming startup.  He read an article I had written, emailed me and said we should meet.  When we met for coffee he showed me the prototype of the mobile ordering/payment stystem he was building and said he was looking for a CEO.  I was impressed and intrigued.  We booked another meeting or two and within 2 weeks we were talking “marriage”, better known as personal responsibilities, founder equity and company formation.  Before I knew it I was CEO of a tech startup (Seconds) and diving into leading a founding team I did not know two weeks ago.

But unfortunately, 6 months after that initial meeting he was on a plane moving down to SF to do contract work, leaving me to find another CTO.

What happened?

I am forever grateful for Jacques to have sought me out and single-handedly placing me on this path I am today.  Yet, in hindsight it’s clear we jumped in too quickly.  We were excited, thought time was of the essence and needed to get to work today!  Within a week or two of knowing each other we were having the “how much percentage of the company do you get and how much do I get” conversation.  I was immediately in charge of estimating product timelines, leading a team of developers, laying out our fundraising strategy, talking with the media and figuring out how we’ll make it to the next phase of the company.

All this and I didn’t even know who these people were!

I didn’t know how they handled stress (although I found out pretty quickly!)  I didn’t know how they had performed in the past on other teams and projects.  Did they run from challenges quickly or where they the ones to stick it out and find a solution?  I was not aware of their tell-tale signs of when things weren’t going right.  And I hadn’t learned how to best approach them to talk over difficult situations and touchy subjects.

In the end, I didn’t know them at all.

And now I know why investors ask about the backgrounds of the founders and how long they have known each other.  It’s very important you take the time to get to know people you want to work with in the future.  If you have a long view on your career – your entrepreneurial journey – you will see there’s decades of time for you to work on various projects and many different people you will work well with.

The thing is it’s very hard to determine that after one or two meetings.

Take it from me, it’s best to start laying the foundation for your future cofounder relationships now so that when the time comes for you to form your dream team you will already know who you will pick.

That, or get used to signing divorce papers…

The # 1 Founder Sin Is So Damn Easy To Avoid

I have noticed a trend recently as I help founders wrap their arms around their ideas and how to best get started.

They come to me with an idea – a problem they have observed in the world – and are devising a unique solution and hopefully in the process attach a kick ass growing business to it.  The problem starts when they try to get too tricky – maybe even too complex – and add all these extra functions and features to their solution.

They create Product Bloat.

This is not good.  It’s the number #1 founder sin.  Yet it’s so easily avoidable.


It’s the number 1 sin because people think too deeply about what they are trying to do.   Thinking too deeply is not actually the problem; implementing too much and attacking the entire vision right out of gate is.  They also want to be different than others in the market, so they think “well, what if we put this into the app?”  Or “such and such is doing X so we’ll just do Y so we can be different.”

The issue with that type of thinking is it takes you farther and farther away from “problem solving” thinking and puts you closer to “creating something new” thinking.  This is wrong because trying to launch a successful product without solving a clear problem in the world is very difficult, if not impossible.


But back to simplicity.  As a founder you need to think about your entire vision as a large iceberg.  The challenge is to find the tip of the iceberg and only release that as the first version.  The rest of the iceberg is under water and very large, just as your entire vision is in your head and not visible to the rest of the world.  Some think of this as an MVP (minimum viable product) and I concur, I just like the illustration better.

Most founders make the mistake of not finding (or determining) the tip of the iceberg and thus end up building the whole iceberg, resulting in lost time, a bloated product and a lost value proposition.

For every Uber – a very simple and easy to use app – there’s thousands of apps that get it wrong and initially build a too complex product.   They end up confusing users and not even getting to the point of an exponential user growth curve.

Twitter was simply a status update and following what others were updating.  That’s it and people could easily talk about it and share it with their friends. YO was absurdly simple, yet at least it was simple enough where millions of people got it and downloaded the app to mess with friends.

The key is to break down your complex problem into its essence.  Know the end game and the large vision but find the simple starting point where millions of people will understand what to do with the app.  Find the least amount of features and code possible to solve your initial problem.

And then release it and gain users.

Once you have your users you can then figure out the next few things to place in the app experience.  But take it from me, don’t commit the number 1 founder sin right out of the gate.

What To Do When You Don’t Know What To Do

I remember it was a rainy, cold and downright depressing winter day in Seattle. The gray skies, piecing wind and nasty looks on people’s faces didn’t help what I was dealing with at all.

That was the day I realized I didn’t know what to do.

I had worked my ass off for almost 2 years on my mobile payment startup Seconds, but too no avail.   The writing was on the wall.  Yes, we had customers and yes we even had revenue.  But no, we weren’t growing and no we weren’t able to raise money to continue forward as a team.

The thing was I didn’t know what to do.

Do I simply shut it down completely?  Quit cold-Turkey?  What about our existing customers?  What about our reputations?  What would others think if we “failed” at our startup?

I was also broke.

I had gone 15 months without pay, barely living off credit cards and other things I scrambled together.  It was terrible.  Some days I didn’t have enough money to eat.  Some days I struggled to buy a ferry ticket home and so I slept on a floor in the office.  I was riding the ferry to and from the office each day because I had no way to pay rent,  so I chose to stay with my sister and her family – an hour and half away across the sound from Seattle.   Graciously, my family and friends helped out when they could which to this day I am ever grateful.

I was definitely worried for myself, not “OMG will I ever be successful” worry but more like “holy crap, I am really on a sinking ship here.”

I didn’t want to admit I needed to jump ship before it sank, I wanted to ignore the holes and guide it to smooth waters.  Why?  Because that’s what “winners” do, right?  But I knew the holes needed patching, and meant getting another job.   I just couldn’t admit to myself the dream was over.

But I just didn’t know what to do.   Then it finally hit me.

It all changed when I re-thought what the dream actually was.  I realized my dream wasn’t about what I was working on at the time, but more about the person I was becoming in the process.  The dream is about being an entrepreneur – the adjective – not the noun.

Entrepreneur – noun.  A proprietor who owns their own business.  A title.

Entrepreneur – adjective.  A person who embodies the qualities of being Courageous. Innovative.  Persistent.  Agile.  Intelligent.  Savvy. Strong.  Personable.  Creative.  Excellent. Fighter.  Winner. 

Once I realized all I needed to do is change the horizon I was gazing towards, everything changed.  I removed myself from the echo-chamber of my head and finally understood, “YIKES, YES THIS BOAT IS SINKING AND I NEED TO GET OFF!”

So I jumped out, found something part time that would plug the hole (support me finically) and was able to live another day.  I started to understand entrepreneurship is a life-long game and to win you need to embody the adjectives, not the nouns.  Once I took that heavy financial burden off my shoulders everything started to get better, my head got clearer and my smile got wider.

I got my mojo back.

Being an entrepreneur is not a title, it’s a person.  Or a persona.   Or a set of characteristics that allow you to dig out of any shitty situation you’ll inevitably find yourself in.

When I found myself in a situation where I didn’t know what to do I simply changed my mindset, which allowed me to see the world in new ways.   Sometimes simply looking at things from a different perspective is all it takes to change your own world.

Founders RAW – Incredible Wisdom From Amp Tab Founder Patrick Henley

Another great Founders RAW conversation, this time with Patrick Henley, founder of Amp Tab.  Patrick lays down some solid wisdom as someone who has been successful in a number of different industries – selling Mount St. Helens ash at 6 yrs old to building houses and now building a software startup to help streamline sales processes.

Listen closely, there’s nuggets of wisdom you don’t want to miss.

Going Deep Inside The Mind Of An Entrepreneur Can Be Scary

The more I live this entrepreneurial life the more I realize how much of a psychological game it is.

I was reminded of it the other day as I watched this interview between Jason Calacanis and Jerry Colonna, a very well known CEO coach in the technology industry.  The 90 minute interview is incredible, they  cover many aspects of how he works with CEO’s and the issues they (we) deal with during the entrepreneurial journey.

There are so many things in this interview I want write about but one of the biggest things that stuck out to me was the idea of “chasing demons” with entrepreneurship.  Jerry and Jason both reveal how their Dad’s lost their jobs when they were young, and how greatly it impacted them, and still does to this day.   For both of them, they committed to never be dependent on a large company, since it could all be gone one day if you are fired.  Deeper, it was the feelings of inadequacy (or the fear of) which drove both to become successful in their pursuits.  It’s amazing and touching to hear them talk about their fears and doubts, and how they are rooted simply from watching their father’s struggles as they were young men.

I think this is something very important to understand.

Why are you so driven?

What demons are you chasing?

Jerry bravely mentions chasing demons is not necessarily bad – not knowing you are chasing demons is.  Not fully understanding who you are and why you are doing things is a scary place to be.

Another thing he points to is how ALL of us feel inadequate, regardless of financial stature and prominence.  He works with over 60 clients (many billionaires) and without fail he see’s highly successful individuals tearing themselves apart, comparing themselves to other founders who – quite frankly – got incredibly lucky with their outcomes.

He emphasizes how much random luck has to do with success in business.

His point: figure yourself out.  Determine who you are outside of your company, your family, and your city.  Once you get to the core of who you are you can fully embrace the life of entrepreneurship without the feeling of insecurity and doubt.

The lesson to take here is although it might be scary to face these demons, once you do you will open yourself up to a much happier entrepreneurial journey.

Don’t Just Break The Rules, Make The Rules

I think about this a lot – If you aren’t breaking rules everyday you aren’t an entrepreneur.

People have many different definitions for the word Entrepreneur, but one of mine circles around rule breaking.  Entrepreneurs believe there are numerous ways to live and get things done.  And typically their creative way is much better than the standard practice.  Entrepreneurs often break the rules so they can see or do something from a different perspective.  Only by breaking the rules can you grab a different view of the world, possibly opening up a new market, product or business model.

To take it a little farther, not only should you break the rules but you need to re-write the rules.  If you are a true leader, the rules you write then become the rules others start to play by.  That’s how you end up owning the market.  Look at Gates, Jobs, Zuckerberg, Musk and many other highly influential and successful entrepreneurs.

All were rule breakers.

And more importantly, all were rule makers.

I read a recent GeekWire recent post on Tim cook, where he essentially said the same thing on breaking the rules:

“I think you should rarely follow the rules. I think you should write the rules. I think if you do follow things in a formulaic manner, you will wind up at best being the same as everybody else, maybe you miss something and you’re a little worse. If you want to excel, you can’t do that.”

Call ’em crazy.  I call ’em entrepreneurs.

5 Crazy But Life Changing Reflections

Life moves pretty fast….. sometimes it’s best to sit back and reflect on your priorities.

The unintended consequence of a startup can be acceleration of everything around you.  It happens so fast, in fact, you end up losing perspective on more important aspects of life.  It’s easy to get out of bed each day, focus on what’s in front of you, go to bed only to get back up the next day to do it all again.  If you are not careful you will find yourself sprinting and spinning in place, making no forward progress at all.

Problems arise when you lose perspective, focusing only on what’s in front of you, becoming all too consumed on accomplishing your immediate goals and not what lies on your life’s horizon.  Soon enough you will reach your “destination” without taking certain aspects of life into consideration – like family, health and the afterlife – leaving you empty and unfulfilled at the end of your journey.

Here are 5 areas I am currently reflecting on to help gain a perspective on life with hopes to figure out a way to better align with what I am doing right now.  (Pardon the existential tone, just one of those days I guess…)


Do I actually enjoy how I spend my days?

Though it’s quite elementary it might help to evaluate if you are actually enjoying where you go and how you spend each day once you get out of bed and leave your house.  Honestly take into account the fun factor, or lack thereof.  Do you feel like a kid?  Or a boring adult?  Do the hours pass with ease and are you fulfilled once the day is over?  Yes, we have to make a wage, earn a paycheck and support our family but we don’t have to dislike it.  We should be enjoying each passing day and the process within.

I quit my full time job a while ago because I didn’t enjoy working for someone else and simply earning dollars for the hours I worked.  I decided to start a company – knowing it was going to be tough – because I value exploration and journey more than maintaining a status quo.  I more value creation than maintenance.

But even now as a free entrepreneur I am not exactly living the charmed life and if I am really honest with myself I remain unfulfilled.  The eyes burn and the legs strain as I make the climb.  I am still searching for the right environment, right cause and right team to help me execute on a worthy mission.  Most important to me is reaching a time in my life where I am able to say “if this is the last day of my life I am extremely excited and happy to do exactly what I plan to do today.”

We’ll get there.

What do I want my grandchildren to say about me?

Gazing towards the horizon, I am pondering how my family and friends will think of me when I am gone.   I hope I am following through and planting the right seeds.  How about you?  How will your friends and family describe you to their friends and others?  What will they talk about and what type of person will they describe?  Will they be proud to be your grandchild?  How did you treat them and what types of memories do you want to leave with them?

I am not even married so I am not even sure why I am thinking about my grandchildren.  Maybe it’s better to understand this concept in terms of legacy.  I want to leave a positive legacy for my family to be proud of.  It’s safe to say I haven’t gotten very far on this one but it is never too early to ponder what it should involve.  I want to be known as someone who never gave up, regardless of how difficult things became.  I want to be known as someone who treated everyone fair and well, regardless of who they were or their circumstances.  I also want to influence change in the world and encourage others to do the same.

I want to be proud of the person my grandchildren hopefully talk about.

If I die today, what will I say to my creator about how I lived my life?

Heavy stuff to think about but just imagine this for a minute:  you die, you go onto to the afterlife and you approach someone (something) who is there to take account of your life.

Yep. Each. And. Every. Minute. Of. Your. Life.

They look at you and proceed to ask you questions about it.  Why did you say that word to that person?  Why didn’t you offer a hand to that  helpless woman?  I gave you millions of dollars to help others, why did you spend it all on your self?

Now imagine them showing you how they hoped you had lived your life.  All the possibilities and potentials of your life start flooding right in front of you, but you cannot speak.  Your face goes white with regret as you realize you squandered all your strengths and talents, not using them as they could have been used to help your fellow man.

I know… crazy stuff.

Who, if anyone in my life, can I share my deepest and darkest fears with?

Do you have a confidant?  Is there someone you can talk to who will understand and hold no judgement, no matter what you tell them?  I have noticed thoughts, feelings, and emotions building up within me at the same time I can’t find an outlet in sight.  It can be frustrating and claustrophobic to identify struggles and challenges within us but lack any outlet or confidant.

Our biggest fears are the only thing holding us back from reaching our greatest potential.  What if you were able to talk them out and allow someone to help you work through them sans any judgment or embarrassment?

I know I am starting to look for people and ways to come to grips with the fears I have in my life.  In fact, writing has become one of them.

If Superman were to look at the world today, what wrongs would he want to make right?

There’s way too much uncertainty and unrest in the world today.  I have to assume even Superman would be overwhelmed with all there is to fix in the world.  But it seems to me an interesting exercise to ponder what Superman would want to fix if he/she were actually real.

Billions of people around the world still don’t have clean drinking water and live on $1 a day.  There are millions of people in the U.S. who are searching for employment opportunities, maybe Superman could think of ways to solve both third world and first world employment problems.  In fact, right down the street in Silicon Valley there are people starving and homeless, yet young startup founders are asking investors to give them millions of dollars so they can build yet another way to share photos and send a short message to someone else – all requiring people own the latest expensive smartphones.

How about terrorism?  How could he create something to curb the urge and the need for people to inflict pain and suffering on others?  And what about the financial challenges every country seems to be under now?  Don’t you think he could get creative enough to help out?  I bet there’s a lot more for Superman to fix, right?

Your unique reflections on the above will indeed bring out the entrepreneur in you.  I guarantee it.

The Best Thing About Falling Is You Can’t Tell Which Way Is Down


Keeping with my recent trend of metaphors, a typical comment you hear from the startup community is “I just took the leap”, meaning someone just left their cushy job and took a huge risk to start a company.

Starting a company can be one of the most exciting times in life, just like the first time you strap a chute on your back and jump from a plane 10,000 feet above the ground.

It can also be one of the scariest.

When you jump to start something new you have no idea how far/close rock bottom actually is and most of the time you are spinning around trying to find equilibrium.  In fact, I used the metaphor almost 2 years ago when I jumped from my job (without a chute nonetheless) and went full time into life as a founder.  And boy has it been a ride worthy of the skydive analogy.  Although I have never jumped from a plane, I can understand what it’s like and why it’s so crazy/awesome/scary.

An interesting phenomenon happens after you jump from your job to a life of entrepreneurship.   You find yourself free falling towards the ground with an awkward, uneasy feeling mixed with both excitement and fright.  Deep down in the pit of your stomach you know it was the right decision but right at the moment your conscious mind is telling you otherwise.

In fact, it’s not telling you.   It’s shouting at you!  Consequently, you don’t actually know which way is down.

This happens for many reasons but mainly because you get so used to the stressful up and down feelings of “falling” it starts to feel like you are floating, just as a skydiver is basically trying to float by balancing an equilibrium in the air.

Your daily routine gets flipped on its head. Your finances start doing weird things and you are wondering if and when the “ground” will actually be hit.  Your personal life is either non-existant or very much challenged.  You find yourself second-guessing your current pursuit for happiness and wondering if you are on the right path.  You find yourself in situations you would have never thought possible, such as talking to investors about millions of dollars and internally saying to yourself “holy crap I have never seen that much money before, what the hell am I thinking!”  It becomes normal to work until 2am and then sleep in, only to have to reschedule the phone calls you were supposed to have in the morning.


You are running your own show.  You can find, recruit and hire anyone you want to join your team.  You determine when and where your meetings will be held, and what time they will start.  You start reading articles with you and your company’s name mentioned in it.  You field emails and calls from multinational companies interested in your product.  You are asked to speak at industry events and local meetups.  You start to see increased interest and engagement with your product, and find yourself quietly saying “it actually works! ” And finally, with an increase in usage comes an increase in revenue so you can start to pay your bills and float your company operations.

Ahhh… the visceral feeling of weightlessness takes over your body.

You now see why the analogy of not knowing which way is down is a damn good one for the startup founder.   The song When You’re Falling by Afro Celt Sound System best sums up “the leap” and is a favorite of mine.

I have always been fascinated with skydiving so it was great to recently connect with Melanie Curtis, founder of, and a professional skydiver.  No doubt, she has a life you wish you had whether you are an extreme athlete or someone who has a passion for life and loves helping the people. She is also an entrepreneur.  I thought it would be great to take a dive with her to get her story, her perspectives on life as a leaper and how she came to entrepreneurship.

Melanie began her career  in NYC and LA working at a major investment bank for 5 years.  She enjoyed it yet found herself spending all her money on skydiving (her first love) so much so that she got good enough to quit the big-time job and go full-time in the sport. As for me, I’m definitely a freedom seeker with my first passion in life being skydiving.  Theres nothing more free than jumping out of an airplane, flying…  yeah, it’s not for the faint of heart, but it’s also a true gateway to the good stuff in life, both literally and figuratively.”

Over the subsequent 9 years, she inadvertently made quite a name for herself in the sport, which was something she didn’t even know was possible going in to it.   She has traveled the world going to drop zones, connecting with their local communities and teaching them how to fly well, stay safe, and have as much fun as possible in the sky. She says diving brings joy, fun, and freedom to the world at large through connected and transformative personal experiences.

“All of my skydiving success has been absolutely, positively, 100% rooted in my passion and love for the sport and community. In that gratuitous, authentic love and joy.  I simply lucked out that my parents instilled me with an over-the-top work ethic and ridiculous personality, two things essential for success in skydiving it seems. haha”


After a couple years of introspection knowing that full-time skydiving wouldn’t make her deeply happy forever, she discovered life coaching, went through a very intense and awesome program and began to build her way up to her next major leap.

“Even though I had the best job in skydiving (I got paid a salary to jump with my friends and organize cool events and theme parties), at the end of 2010 I took the second major leap in my professional life, quit that job and went into business for myself, founding”

What is I wondered?  Their Mission Statement states: “We strive to change the world one person at a time through transformative personal relationships that help people identify and authentically live their core values. (ie. Live the dream. LTD. Word.)”

Melanie notes that yes, what’s in parentheses is actually part of the mission statement.  “ is my coaching business.. both skydive coaching and life coaching… it’s me… my approach to life, what I’ve learned finding the path to this completely free, mobile, and balanced lifestyle I now lead, and how I now can help others find and live their version of ‘the dream’ too.”

The name “highcomms” comes from past conversations with one of her best friends back in the day.  Anytime they hadn’t talked for a while they would text each other “comms.” As in communication.  Like, “hey, we haven’t talked in a while, it’s time, let’s do this…”   One day we’re talking and I get all fired up and say something along the lines of this, “I’m not just about comms… I’m about HIGH comms… full-on, meat-and-potatoes conversations, fully putting yourself out there, unabashed authenticity…” and whatever else I said. ”

And so it began.

It’s obvious Melanie excels in the type of conversation that helps people get to important answers, and see them through to actual life change.   She helps people see the pathways to their own leaps, helps them see ways through whatever might be holding them back.  Also, she helps them figure out and uncover what they really want to do with their lives by setting action goals and  holding them accountable to doing it, every single week.

She typically works with one-on-one clients in the US and abroad over the phone and Skype, and this past year they have finally got their website set up to continue to offer online classes/education/webinars to help bring coaching tools to people who may not be able to afford the more expensive 1-on-1 service.

“This has been the natural evolution of my life-coaching business, given all my experience teaching with my skydive coaching for so many years. I even brought on my best friend and educational consultant, Carolyn Chow, as a partner to help me grow this side of the business and ensure the class content is structured in the best possible way for clients/customers.”

As I gathered information a few lessons popped out from the back and forth I had with Melanie.

The impossible is possible.

I know that sounds super cliche, but think about it as someone who’s never jumped out of an airplane before.   We tend to think about doing it, and it seems totally impossible, like we’ll surely die.  And then we do it and not only do we LIVE, but we have the most fun of our lives, enter a community that thrives on that same freedom and fun, and that cracks our mind wide open.  Skydiving teaches you the impossible is possible, something I’ve had internalized inside me from a very young age.

The belief that I really can do anything has given me the courage every time I’ve come to a bigger precipice in life.  It’s the same thing with entrepreneurship.   As soon as I actually had the conscious thought that I could go into business for myself, be my OWN boss, it wasn’t instantaneous by any means, but the idea was all it took.  Here’s an article Melanie wrote on this very thing topic.

We all need help from others.

I most definitely stay fully immersed in my life coaching work, and have a life coach myself.  Just because I’m an “expert” doesn’t mean I’m not human..  I’m such a believer in life coaching as something that truly helps anyone no matter their situation.  I use all the skills I’ve learned in my coaching, experience, education, and I see all of the stuff that I go through as opportunity to learn more, share more, and connect more with my customers and clients.  Here’s another article Melanie wrote that speaks to entrepreneurial stress.

There’s lots of opportunity in helping people

Where I think can go in the future is expanding into more of the self-help aspects of business. Carolyn and I are working to expand the online education portion of the business, currently recording new classes that will go up for sale ongoing. 

I’m writing my first book as we speak and plan to have it published by the end of this year, with the goal of increased reach, credibility, and presence in the industry. We know we could expand into workshops and stuff like that, but we’re all about keeping our lifestyle free and mobile, we really love the online stuff.  So perhaps maybe one big workshop a year, maybe two, so it’s not a huge time constraint on our lives.

Next time you feel yourself free falling – whether jumping from a plane or off a cliff towards your next venture – just remember anything is possible.  Or better yet… just remember to pull the chute early so you can fully enjoy the ride.

*If you are interested in your story being told here, feel free to reach out to me.

Marley Said It Best: Tears In Our Eyes Burn While We Wait For Our Turn

One of my favorite songs is Waiting In Vain by Bob Marley.  I cannot put my finger on why I like it so much but smooth rhythms coupled with intriguing lyrics make for a timeless classic.

I heard it today on the way into the office and it got me thinking about one of the strongest lines in the song, “tears in my eyes burn while I’m waiting for my turn.”   Although one could see many different angles on Marley’s claim, I sense he is in pain from a past lover he hopes to reconnect with once again.  And before you pass it off as just another heartbroken lyric I should point out another way to think about.  He’s waiting around, frustrated, waiting on someone or something to happen and not living the life right in front of him.  He’s so distraught he can’t do anything else.

I think entrepreneurs can identify with that, can’t we.

Deep down in the song I see some interesting lessons from Bob Marley.  Entrepreneurs are very strong individuals but they are also very impatient animals.  We want (and even believe) good things will happen to us quickly and with the least amount of effort.  This is simply not true and fatal to the entrepreneur if not fully understood.  Good things take time to develop.

We also tend to get very emotionally wrapped up in what we are doing and when things don’t go our way it can be devastating.  So, the usual result is we pound away against the brick wall as we complain about our circumstances to anyone who will listen.

That’s no good for anyone.

It’s pretty easy to find yourself waiting in vain for your turn.  Your startup or career might not be on the growth trajectory you had initially hoped for and now you find yourself frustrated with each passing day.  You may find yourself – more or less – waiting for the big thing to happen to your rather than going out and actually making it happen.

“Why didn’t he invest in our company?  Can’t he see we’ll be the next Facebook?!”

“No one wants to use our product… what am I doing wrong?”

Notice these are coming from a negative direction… Unfortunately, if you are asking questions in vain you are heading down the wrong path.  These are simply the wrong questions and the wrong perspective to build your company with.

The questions you should be asking include:

“why were users attracted to this idea in the first place?  What problem or issue is still there we need to solve?  Is it maybe we just haven’t found the fully baked solution?  How can we take a slightly different view of the problem we are trying to solve?”

As you can see, these questions lead to positive outcomes, breakthroughs or new discoveries and will help any entrepreneur or startup get better aligned.

Yes, I even felt myself in this mentality lately and have made a commitment to stop at the moment notice I am going that direction.

Don’t wait in vain.  Just go out and make it happen.

Should He Stay In Grad School Or Start His Own Company?

Below is my response to a recent email I received from a follower asking some very important questions as he ponders his own entrepreneurial journey.   While I was responding to him it occurred to me you too might be grinding over the same issues.  So here’s my answers to his questions.

His questions are in bold.

I am curious if you are having the same thoughts and if you agree with my positions.


Hey ______,

Great to meet you and thanks for reaching out with your questions. Glad you are a fan of Seconds!  First off I commend you for considering a direction as a founder. It’s one of the most exciting experiences of your life, but also will probably be the most scary and challenging. Just know I wouldn’t second guess myself for the world!

1. I’m toying with the idea of quitting grad-school and going full-time on my 4 month old startup..what is your philosophy on the value of education in school vs education via building a business?

If you are serious about your startup, quit school now. In my opinion, grad school will always be there – but your window of opportunity in tech/business will not always be there. Business climates change, technology moves forward, your solution (the idea) will probably not be applicable in its current state a few years from now so if you see something right now – go for it. You will also learn a hell of a lot more about the real world and how to live a successful life when you fully commit to building your startup. The ability to build a product, how to evaluate the market, figure out your product positioning, learning the ins and outs of VC’s and raising capital to fund your business, talking with larger companies when doing business development deals, hiring, firing, leading a team of people, conflict management, doing reviews and salary negotiations, budgeting, cap table/equity allocations, etc…

Do you think grad school will actually give you those experiences in a hards on, real life environment?

2. Do you think it’s possible to build a meaningful business in this modern age of automation without hiring anyone?

It is possible to build a profitable, cash flow business without hiring anyone. If you are technical and can build out the tech side of things, than yes you might be able to go at it alone. And this is probably what you should do until you can affordably bring on others to help you.

In terms of meaningful business and company, I would have to say it will require others to fill in the gaps and help you create the right culture for your company. In my opinion, meaning comes from purpose, passion and culture. It’s the “why” of the organization. “why does your company exist?” is the question you will need to answer. Even in today’s high-tech automated world, there are things only us humans can do, and do well. I would suggest finding others to help you fill those gaps.

Plus, life is more fulfilling when you have others there to experience it with.

3. What’s the hardest thing you’ve ever done as an entrepreneur?

Ironically, the hardest thing I have done as an entrepreneur is quit my job and going out on my own to build a sustainable company. It’s like being a trapeze artist without the safety net, and it can be really scary. Truth be told, Seconds is not all the way there yet and I am still fighting in the trenches of entrepreneurship, trying to build my company as well as survive through life. It’s a full contact sport. You have to be ready to do more than you ever thought you could with less money than you ever thought was possible and with it taking longer than you ever thought it would.

But to me, that is the most fulfilling aspect of being a founder. You get to overcome insurmountable odds and do things most people are too afraid to do. You get to live your own “Rudy” story. I don’t look at entrepreneurship as a way to get rich or famous, which happens from time to time. I look at it as a duty to move our society forward; a positive contribution to our world. And in the end, that is one of the most rewarding feelings anyone can be given.

Hope that helps!